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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5)transporters (2) Show 7 proteins XML

enzymes (5)transporters (2) Show 7 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:40 UTC

HMDB ID

HMDB0014587

Secondary Accession Numbers

HMDB14587

Metabolite Identification

Common Name

Teniposide

Description

Teniposide, also known as HSDB 6546 or NSC 122819, belongs to the class of inorganic compounds known as metalloid oxides. These are inorganic compounds containing an oxygen atom of an oxidation state of -2, in which the heaviest atom bonded to the oxygen is a metalloid. Teniposide is an extremely weak basic (essentially neutral) compound (based on its pKa). teniposide can be converted into teniposide catechol derivative and formaldehyde; which is mediated by the enzymes cytochrome P450 3A4 and cytochrome P450 3A5. A semisynthetic derivative of podophyllotoxin that exhibits antitumor activity. In humans, teniposide is involved in teniposide metabolism pathway. Teniposide is formally rated as a probable carcinogen (by IARC 2A) and is also a potentially toxic compound. Fecal excretion of radioactivity within 72 hours after dosing accounted for 0% to 10% of the dose. Accumulated breaks in DNA prevent cells from entering into the mitotic phase of the cell cycle, and lead to cell death. This complex induces breaks in double stranded DNA and prevents repair by topoisomerase II binding. The cytotoxic effects of teniposide are related to the relative number of double-stranded DNA breaks produced in cells, which are a reflection of the stabilization of a topoisomerase II-DNA intermediate. Teniposide acts primarily in the G2 and S phases of the cycle.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

444
  Mrv0541 02231214412D          

 50 57  0  0  1  0            999 V2000
    3.5771    4.2067    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.8704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9393    0.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.3671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5087    2.4639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0808   -0.9027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -0.0454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9938    2.4696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    1.6047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8457   -3.9587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0435   -4.6502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944   -4.5830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5234   -2.1079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5234   -3.7580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -0.8704    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6655   -1.2829    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2365   -1.2829    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6655   -2.1079    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2365   -2.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -2.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1235   -0.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2735   -0.7325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.0454    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3799   -2.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    0.3671    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5220    1.6047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8075    1.1922    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2365    1.1922    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4857   -2.5261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9642   -3.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4791   -3.3855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2234   -3.8151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9872    1.6103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944   -2.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799   -3.3454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2497    2.8994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944   -3.7580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8089   -2.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1939   -4.7388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8089   -3.3454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2465    3.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9121    4.2118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6541    4.9955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8291    4.9923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799   -4.9955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2379   -2.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4175   -0.4817    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2687   -1.5505    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9479    1.9302    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8055    0.8578    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 41  1  0  0  0  0
  1 44  1  0  0  0  0
 17  2  1  1  0  0  0
 23  2  1  1  0  0  0
  3 21  1  0  0  0  0
  3 22  1  0  0  0  0
  4 23  1  0  0  0  0
  4 28  1  0  0  0  0
  5 26  1  0  0  0  0
  5 36  1  0  0  0  0
  6 22  2  0  0  0  0
 25  7  1  6  0  0  0
  8 33  1  0  0  0  0
  8 36  1  0  0  0  0
 27  9  1  1  0  0  0
 10 31  1  0  0  0  0
 10 39  1  0  0  0  0
 11 32  1  0  0  0  0
 11 39  1  0  0  0  0
 12 37  1  0  0  0  0
 12 45  1  0  0  0  0
 13 38  1  0  0  0  0
 13 46  1  0  0  0  0
 14 40  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 21  1  0  0  0  0
 15 47  1  6  0  0  0
 16 18  1  0  0  0  0
 16 22  1  0  0  0  0
 16 48  1  1  0  0  0
 17 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 24  1  6  0  0  0
 19 20  1  0  0  0  0
 19 29  2  0  0  0  0
 20 30  2  0  0  0  0
 23 25  1  0  0  0  0
 24 34  2  0  0  0  0
 24 35  1  0  0  0  0
 25 27  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 49  1  1  0  0  0
 28 33  1  0  0  0  0
 28 50  1  6  0  0  0
 29 31  1  0  0  0  0
 30 32  1  0  0  0  0
 31 32  2  0  0  0  0
 34 38  1  0  0  0  0
 35 37  2  0  0  0  0
 36 41  1  0  0  0  0
 37 40  1  0  0  0  0
 38 40  2  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
M  END

HMDB0014587
     RDKit          3D
Teniposide
 78 85  0  0  0  0  0  0  0  0999 V2000
   -4.2605    2.2376    2.7204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3865    2.1250    1.8749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3131    1.3086    0.7598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1539    0.6194    0.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9992   -0.2178   -0.6167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7296   -0.8966   -0.8463 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1431   -1.4762    0.3954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7796   -2.6042    0.9122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3279   -3.2192    2.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2247   -2.6875    2.6954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5994   -1.5713    2.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0440   -0.9355    1.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2909    0.2477    0.5616 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0251    0.0026    0.2158 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9473    0.7354    0.9528 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5850    1.7082    0.2305 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6252    1.2807   -0.4787 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4657    1.1700   -1.9839 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7596    1.0255   -2.4610 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5567    0.1167   -1.8676 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9350    0.7133   -1.6576 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1485    0.1332   -1.9031 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2423    0.8547   -1.6405 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0602    2.1187   -1.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3652    2.2569   -1.0648 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.2091   -0.5057   -0.7310 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0959   -0.0790   -0.0622 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2305   -0.0331    1.4419 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8581   -1.1627    1.9063 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7681   -0.0429    1.9193 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7821    0.5505    3.1534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9891    0.8755   -0.5888 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0890    1.5235   -1.6225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0597    1.7515   -2.6619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0117    0.7114   -2.6412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9601    0.5763   -3.4475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6584   -0.1390   -1.5158 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9524   -3.4715    3.8342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6139   -4.7325    3.6405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7183   -4.3214    2.8205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1096   -0.3362   -1.4530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2903    0.3275   -1.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3563    0.1845   -2.0689 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2284   -0.6592   -3.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3675    1.1414   -0.1136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5353    1.8543    0.1942 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0184    1.2377    3.1900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3366    2.5267    2.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4079    2.9804    3.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3270    0.7537    1.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9717   -1.7765   -1.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6399   -3.0173    0.4187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2597   -1.2056    2.7261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3741    0.9841    1.4005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2499    1.3554    1.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4699    2.0424   -0.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8937    0.2689   -2.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0332    2.0824   -2.4049 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7388   -0.6950   -2.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1894   -0.8989   -2.3056 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2848    0.4882   -1.7996 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8563    2.8409   -0.8775 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2838   -0.8019   -0.2921 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7223    0.9103    1.7556 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2430   -1.0593    2.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5120   -1.1277    1.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2845    1.3886    3.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6902    1.6742   -0.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5984    0.7630   -2.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3510    2.4428   -1.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8410   -0.8177   -1.8527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9904   -5.3961    2.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9240   -5.1914    4.5786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0242   -0.9814   -2.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4600   -0.2597   -3.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9164   -1.6566   -2.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1937   -0.6767   -3.7430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3228    1.7634   -0.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
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 12 13  1  0
 13 14  1  0
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 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
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 20 26  1  0
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 28 30  1  0
 30 31  1  0
 13 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  2  0
 35 37  1  0
 10 38  1  0
 38 39  1  0
 39 40  1  0
  5 41  2  0
 41 42  1  0
 42 43  1  0
 43 44  1  0
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 37  6  1  0
 12  7  1  0
 30 15  1  0
 37 32  1  0
 40  9  1  0
 27 17  1  0
 25 21  1  0
  1 47  1  0
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  4 50  1  0
  6 51  1  6
  8 52  1  0
 11 53  1  0
 13 54  1  1
 15 55  1  1
 17 56  1  6
 18 57  1  0
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 22 60  1  0
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 24 62  1  0
 27 63  1  1
 28 64  1  6
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 30 66  1  1
 31 67  1  0
 32 68  1  1
 33 69  1  0
 33 70  1  0
 37 71  1  6
 39 72  1  0
 39 73  1  0
 41 74  1  0
 44 75  1  0
 44 76  1  0
 44 77  1  0
 46 78  1  0
M  END

444
  Mrv0541 02231214412D          

 50 57  0  0  1  0            999 V2000
    3.5771    4.2067    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.8704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9393    0.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.3671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5087    2.4639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0808   -0.9027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -0.0454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9938    2.4696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    1.6047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8457   -3.9587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0435   -4.6502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944   -4.5830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5234   -2.1079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5234   -3.7580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6655   -1.2829    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2365   -1.2829    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6655   -2.1079    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2365   -2.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -2.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1235   -0.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2735   -0.7325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.0454    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3799   -2.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    0.3671    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5220    1.6047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8075    1.1922    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2365    1.1922    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4857   -2.5261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9642   -3.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4791   -3.3855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2234   -3.8151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9872    1.6103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944   -2.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.0944   -3.7580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8089   -2.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1939   -4.7388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8089   -3.3454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2465    3.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9121    4.2118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6541    4.9955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8291    4.9923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799   -4.9955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2379   -2.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4175   -0.4817    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2687   -1.5505    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9479    1.9302    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8055    0.8578    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 41  1  0  0  0  0
  1 44  1  0  0  0  0
 17  2  1  1  0  0  0
 23  2  1  1  0  0  0
  3 21  1  0  0  0  0
  3 22  1  0  0  0  0
  4 23  1  0  0  0  0
  4 28  1  0  0  0  0
  5 26  1  0  0  0  0
  5 36  1  0  0  0  0
  6 22  2  0  0  0  0
 25  7  1  6  0  0  0
  8 33  1  0  0  0  0
  8 36  1  0  0  0  0
 27  9  1  1  0  0  0
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 25 27  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 49  1  1  0  0  0
 28 33  1  0  0  0  0
 28 50  1  6  0  0  0
 29 31  1  0  0  0  0
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 31 32  2  0  0  0  0
 34 38  1  0  0  0  0
 35 37  2  0  0  0  0
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 38 40  2  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014587

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12COC(=O)[C@]1([H])[C@H](C1=CC(OC)=C(O)C(OC)=C1)C1=CC3=C(OCO3)C=C1[C@H]2O[C@@H]1O[C@]2([H])COC(O[C@@]2([H])[C@H](O)[C@H]1O)C1=CC=CS1

> <INCHI_IDENTIFIER>
InChI=1S/C32H32O13S/c1-37-19-6-13(7-20(38-2)25(19)33)23-14-8-17-18(42-12-41-17)9-15(14)28(16-10-39-30(36)24(16)23)44-32-27(35)26(34)29-21(43-32)11-40-31(45-29)22-4-3-5-46-22/h3-9,16,21,23-24,26-29,31-35H,10-12H2,1-2H3/t16-,21+,23+,24-,26+,27+,28+,29+,31?,32-/m0/s1

> <INCHI_KEY>
NRUKOCRGYNPUPR-PSZSYXFXSA-N

> <FORMULA>
C32H32O13S

> <MOLECULAR_WEIGHT>
656.654

> <EXACT_MASS>
656.1563618

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
65.79977288265849

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(10R,11R,15R,16S)-16-{[(4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-(thiophen-2-yl)-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one

> <ALOGPS_LOGP>
2.78

> <JCHEM_LOGP>
2.784029192333334

> <ALOGPS_LOGS>
-4.04

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.275460152375853

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.329948671524686

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6857288563510577

> <JCHEM_POLAR_SURFACE_AREA>
160.82999999999998

> <JCHEM_REFRACTIVITY>
155.6094999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.98e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
teniposide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014587
     RDKit          3D
Teniposide
 78 85  0  0  0  0  0  0  0  0999 V2000
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   -5.3131    1.3086    0.7598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1539    0.6194    0.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9992   -0.2178   -0.6167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7296   -0.8966   -0.8463 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1431   -1.4762    0.3954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7796   -2.6042    0.9122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3279   -3.2192    2.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
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 46 78  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 444                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       6.677   7.853   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       6.574  -1.625   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      11.087   0.031   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       7.908   0.685   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       6.550   4.599   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      13.217  -1.685   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       3.907  -0.085   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       9.322   4.610   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       3.907   2.995   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       5.312  -7.390   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       7.548  -8.680   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      13.243  -8.555   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      15.910  -3.935   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      15.910  -7.015   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.242  -1.625   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.576  -2.395   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.908  -2.395   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.576  -3.935   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.908  -3.935   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.242  -4.705   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.564  -0.128   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.711  -1.367   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.574  -0.085   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.909  -4.705   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.241   0.685   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.574   2.995   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.241   2.225   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.908   2.225   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.507  -4.715   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.267  -6.309   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.494  -6.320   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.884  -7.122   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.309   3.006   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      13.243  -3.935   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.909  -6.245   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.933   5.412   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      13.243  -7.015   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      14.577  -4.705   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.962  -8.846   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      14.577  -6.245   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       7.927   6.952   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       9.169   7.862   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       8.688   9.325   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       7.148   9.319   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      11.909  -9.325   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      17.244  -4.705   0.000  0.00  0.00           C+0
HETATM   47  H   UNK     0       8.246  -0.899   0.000  0.00  0.00           H+0
HETATM   48  H   UNK     0      11.702  -2.894   0.000  0.00  0.00           H+0
HETATM   49  H   UNK     0       5.503   3.603   0.000  0.00  0.00           H+0
HETATM   50  H   UNK     0       8.970   1.601   0.000  0.00  0.00           H+0
CONECT    1   41   44                                                       
CONECT    2   17   23                                                       
CONECT    3   21   22                                                       
CONECT    4   23   28                                                       
CONECT    5   26   36                                                       
CONECT    6   22                                                            
CONECT    7   25                                                            
CONECT    8   33   36                                                       
CONECT    9   27                                                            
CONECT   10   31   39                                                       
CONECT   11   32   39                                                       
CONECT   12   37   45                                                       
CONECT   13   38   46                                                       
CONECT   14   40                                                            
CONECT   15   16   17   21   47                                             
CONECT   16   15   18   22   48                                             
CONECT   17    2   15   19                                                  
CONECT   18   16   20   24                                                  
CONECT   19   17   20   29                                                  
CONECT   20   18   19   30                                                  
CONECT   21    3   15                                                       
CONECT   22    3    6   16                                                  
CONECT   23    2    4   25                                                  
CONECT   24   18   34   35                                                  
CONECT   25    7   23   27                                                  
CONECT   26    5   27   28   49                                             
CONECT   27    9   25   26                                                  
CONECT   28    4   26   33   50                                             
CONECT   29   19   31                                                       
CONECT   30   20   32                                                       
CONECT   31   10   29   32                                                  
CONECT   32   11   30   31                                                  
CONECT   33    8   28                                                       
CONECT   34   24   38                                                       
CONECT   35   24   37                                                       
CONECT   36    5    8   41                                                  
CONECT   37   12   35   40                                                  
CONECT   38   13   34   40                                                  
CONECT   39   10   11                                                       
CONECT   40   14   37   38                                                  
CONECT   41    1   36   42                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44    1   43                                                       
CONECT   45   12                                                            
CONECT   46   13                                                            
CONECT   47   15                                                            
CONECT   48   16                                                            
CONECT   49   26                                                            
CONECT   50   28                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  114    0
END

COMPND    HMDB0014587
HETATM    1  C1  UNL     1      -4.261   2.238   2.720  1.00  0.00           C  
HETATM    2  O1  UNL     1      -5.387   2.125   1.875  1.00  0.00           O  
HETATM    3  C2  UNL     1      -5.313   1.309   0.760  1.00  0.00           C  
HETATM    4  C3  UNL     1      -4.154   0.619   0.479  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.999  -0.218  -0.617  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.730  -0.897  -0.846  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.143  -1.476   0.395  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.780  -2.604   0.912  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.328  -3.219   2.063  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.225  -2.688   2.695  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.599  -1.571   2.178  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.044  -0.935   1.011  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.291   0.248   0.562  1.00  0.00           C  
HETATM   14  O2  UNL     1       1.025   0.003   0.216  1.00  0.00           O  
HETATM   15  C13 UNL     1       1.947   0.735   0.953  1.00  0.00           C  
HETATM   16  O3  UNL     1       2.585   1.708   0.230  1.00  0.00           O  
HETATM   17  C14 UNL     1       3.625   1.281  -0.479  1.00  0.00           C  
HETATM   18  C15 UNL     1       3.466   1.170  -1.984  1.00  0.00           C  
HETATM   19  O4  UNL     1       4.760   1.025  -2.461  1.00  0.00           O  
HETATM   20  C16 UNL     1       5.557   0.117  -1.868  1.00  0.00           C  
HETATM   21  C17 UNL     1       6.935   0.713  -1.658  1.00  0.00           C  
HETATM   22  C18 UNL     1       8.149   0.133  -1.903  1.00  0.00           C  
HETATM   23  C19 UNL     1       9.242   0.855  -1.640  1.00  0.00           C  
HETATM   24  C20 UNL     1       9.060   2.119  -1.145  1.00  0.00           C  
HETATM   25  S1  UNL     1       7.365   2.257  -1.065  1.00  0.00           S  
HETATM   26  O5  UNL     1       5.209  -0.506  -0.731  1.00  0.00           O  
HETATM   27  C21 UNL     1       4.096  -0.079  -0.062  1.00  0.00           C  
HETATM   28  C22 UNL     1       4.230  -0.033   1.442  1.00  0.00           C  
HETATM   29  O6  UNL     1       4.858  -1.163   1.906  1.00  0.00           O  
HETATM   30  C23 UNL     1       2.768  -0.043   1.919  1.00  0.00           C  
HETATM   31  O7  UNL     1       2.782   0.551   3.153  1.00  0.00           O  
HETATM   32  C24 UNL     1      -0.989   0.876  -0.589  1.00  0.00           C  
HETATM   33  C25 UNL     1      -0.089   1.524  -1.623  1.00  0.00           C  
HETATM   34  O8  UNL     1      -1.060   1.752  -2.662  1.00  0.00           O  
HETATM   35  C26 UNL     1      -2.012   0.711  -2.641  1.00  0.00           C  
HETATM   36  O9  UNL     1      -2.960   0.576  -3.448  1.00  0.00           O  
HETATM   37  C27 UNL     1      -1.658  -0.139  -1.516  1.00  0.00           C  
HETATM   38  O10 UNL     1      -0.952  -3.472   3.834  1.00  0.00           O  
HETATM   39  C28 UNL     1      -1.614  -4.733   3.640  1.00  0.00           C  
HETATM   40  O11 UNL     1      -2.718  -4.321   2.821  1.00  0.00           O  
HETATM   41  C29 UNL     1      -5.110  -0.336  -1.453  1.00  0.00           C  
HETATM   42  C30 UNL     1      -6.290   0.327  -1.222  1.00  0.00           C  
HETATM   43  O12 UNL     1      -7.356   0.185  -2.069  1.00  0.00           O  
HETATM   44  C31 UNL     1      -7.228  -0.659  -3.197  1.00  0.00           C  
HETATM   45  C32 UNL     1      -6.367   1.141  -0.114  1.00  0.00           C  
HETATM   46  O13 UNL     1      -7.535   1.854   0.194  1.00  0.00           O  
HETATM   47  H1  UNL     1      -4.018   1.238   3.190  1.00  0.00           H  
HETATM   48  H2  UNL     1      -3.337   2.527   2.178  1.00  0.00           H  
HETATM   49  H3  UNL     1      -4.408   2.980   3.525  1.00  0.00           H  
HETATM   50  H4  UNL     1      -3.327   0.754   1.174  1.00  0.00           H  
HETATM   51  H5  UNL     1      -2.972  -1.777  -1.524  1.00  0.00           H  
HETATM   52  H6  UNL     1      -3.640  -3.017   0.419  1.00  0.00           H  
HETATM   53  H7  UNL     1       0.260  -1.206   2.726  1.00  0.00           H  
HETATM   54  H8  UNL     1      -0.374   0.984   1.401  1.00  0.00           H  
HETATM   55  H9  UNL     1       1.250   1.355   1.642  1.00  0.00           H  
HETATM   56  H10 UNL     1       4.470   2.042  -0.351  1.00  0.00           H  
HETATM   57  H11 UNL     1       2.894   0.269  -2.258  1.00  0.00           H  
HETATM   58  H12 UNL     1       3.033   2.082  -2.405  1.00  0.00           H  
HETATM   59  H13 UNL     1       5.739  -0.695  -2.638  1.00  0.00           H  
HETATM   60  H14 UNL     1       8.189  -0.899  -2.306  1.00  0.00           H  
HETATM   61  H15 UNL     1      10.285   0.488  -1.800  1.00  0.00           H  
HETATM   62  H16 UNL     1       9.856   2.841  -0.877  1.00  0.00           H  
HETATM   63  H17 UNL     1       3.284  -0.802  -0.292  1.00  0.00           H  
HETATM   64  H18 UNL     1       4.722   0.910   1.756  1.00  0.00           H  
HETATM   65  H19 UNL     1       5.243  -1.059   2.809  1.00  0.00           H  
HETATM   66  H20 UNL     1       2.512  -1.128   1.947  1.00  0.00           H  
HETATM   67  H21 UNL     1       2.284   1.389   3.124  1.00  0.00           H  
HETATM   68  H22 UNL     1      -1.690   1.674  -0.278  1.00  0.00           H  
HETATM   69  H23 UNL     1       0.598   0.763  -2.004  1.00  0.00           H  
HETATM   70  H24 UNL     1       0.351   2.443  -1.248  1.00  0.00           H  
HETATM   71  H25 UNL     1      -0.841  -0.818  -1.853  1.00  0.00           H  
HETATM   72  H26 UNL     1      -0.990  -5.396   2.994  1.00  0.00           H  
HETATM   73  H27 UNL     1      -1.924  -5.191   4.579  1.00  0.00           H  
HETATM   74  H28 UNL     1      -5.024  -0.981  -2.321  1.00  0.00           H  
HETATM   75  H29 UNL     1      -6.460  -0.260  -3.907  1.00  0.00           H  
HETATM   76  H30 UNL     1      -6.916  -1.657  -2.830  1.00  0.00           H  
HETATM   77  H31 UNL     1      -8.194  -0.677  -3.743  1.00  0.00           H  
HETATM   78  H32 UNL     1      -8.323   1.763  -0.409  1.00  0.00           H  
CONECT    1    2   47   48   49
CONECT    2    3
CONECT    3    4    4   45
CONECT    4    5   50
CONECT    5    6   41   41
CONECT    6    7   37   51
CONECT    7    8    8   12
CONECT    8    9   52
CONECT    9   10   10   40
CONECT   10   11   38
CONECT   11   12   12   53
CONECT   12   13
CONECT   13   14   32   54
CONECT   14   15
CONECT   15   16   30   55
CONECT   16   17
CONECT   17   18   27   56
CONECT   18   19   57   58
CONECT   19   20
CONECT   20   21   26   59
CONECT   21   22   22   25
CONECT   22   23   60
CONECT   23   24   24   61
CONECT   24   25   62
CONECT   26   27
CONECT   27   28   63
CONECT   28   29   30   64
CONECT   29   65
CONECT   30   31   66
CONECT   31   67
CONECT   32   33   37   68
CONECT   33   34   69   70
CONECT   34   35
CONECT   35   36   36   37
CONECT   37   71
CONECT   38   39
CONECT   39   40   72   73
CONECT   41   42   74
CONECT   42   43   45   45
CONECT   43   44
CONECT   44   75   76   77
CONECT   45   46
CONECT   46   78
END

HMDB0014587
     RDKit          3D
Teniposide
 78 85  0  0  0  0  0  0  0  0999 V2000
   -4.2605    2.2376    2.7204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3865    2.1250    1.8749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3131    1.3086    0.7598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1539    0.6194    0.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9992   -0.2178   -0.6167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7296   -0.8966   -0.8463 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1431   -1.4762    0.3954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7796   -2.6042    0.9122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3279   -3.2192    2.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2247   -2.6875    2.6954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5994   -1.5713    2.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0440   -0.9355    1.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2909    0.2477    0.5616 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0251    0.0026    0.2158 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9473    0.7354    0.9528 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5850    1.7082    0.2305 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6252    1.2807   -0.4787 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4657    1.1700   -1.9839 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7596    1.0255   -2.4610 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5567    0.1167   -1.8676 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9350    0.7133   -1.6576 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1485    0.1332   -1.9031 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2423    0.8547   -1.6405 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0602    2.1187   -1.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3652    2.2569   -1.0648 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.2091   -0.5057   -0.7310 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0959   -0.0790   -0.0622 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2305   -0.0331    1.4419 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8581   -1.1627    1.9063 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7681   -0.0429    1.9193 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7821    0.5505    3.1534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9891    0.8755   -0.5888 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0890    1.5235   -1.6225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0597    1.7515   -2.6619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0117    0.7114   -2.6412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9601    0.5763   -3.4475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6584   -0.1390   -1.5158 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9524   -3.4715    3.8342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6139   -4.7325    3.6405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7183   -4.3214    2.8205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1096   -0.3362   -1.4530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2903    0.3275   -1.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3563    0.1845   -2.0689 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2284   -0.6592   -3.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3675    1.1414   -0.1136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5353    1.8543    0.1942 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0184    1.2377    3.1900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3366    2.5267    2.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4079    2.9804    3.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3270    0.7537    1.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9717   -1.7765   -1.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6399   -3.0173    0.4187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2597   -1.2056    2.7261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3741    0.9841    1.4005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2499    1.3554    1.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4699    2.0424   -0.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8937    0.2689   -2.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0332    2.0824   -2.4049 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7388   -0.6950   -2.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1894   -0.8989   -2.3056 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2848    0.4882   -1.7996 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8563    2.8409   -0.8775 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2838   -0.8019   -0.2921 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7223    0.9103    1.7556 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2430   -1.0593    2.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5120   -1.1277    1.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2845    1.3886    3.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6902    1.6742   -0.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5984    0.7630   -2.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3510    2.4428   -1.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8410   -0.8177   -1.8527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9904   -5.3961    2.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9240   -5.1914    4.5786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0242   -0.9814   -2.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4600   -0.2597   -3.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9164   -1.6566   -2.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1937   -0.6767   -3.7430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3228    1.7634   -0.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 20 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 13 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  2  0
 35 37  1  0
 10 38  1  0
 38 39  1  0
 39 40  1  0
  5 41  2  0
 41 42  1  0
 42 43  1  0
 43 44  1  0
 42 45  2  0
 45 46  1  0
 45  3  1  0
 37  6  1  0
 12  7  1  0
 30 15  1  0
 37 32  1  0
 40  9  1  0
 27 17  1  0
 25 21  1  0
  1 47  1  0
  1 48  1  0
  1 49  1  0
  4 50  1  0
  6 51  1  6
  8 52  1  0
 11 53  1  0
 13 54  1  1
 15 55  1  1
 17 56  1  6
 18 57  1  0
 18 58  1  0
 20 59  1  0
 22 60  1  0
 23 61  1  0
 24 62  1  0
 27 63  1  1
 28 64  1  6
 29 65  1  0
 30 66  1  1
 31 67  1  0
 32 68  1  1
 33 69  1  0
 33 70  1  0
 37 71  1  6
 39 72  1  0
 39 73  1  0
 41 74  1  0
 44 75  1  0
 44 76  1  0
 44 77  1  0
 46 78  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4'-Demethylepipodophyllotoxin 9-(4,6-O-2-thenylidene-beta-D-glucopyranoside)	ChEBI
4'-Demethylepipodophyllotoxin-beta-D-thenylidene glucoside	ChEBI
HSDB 6546	ChEBI
NSC 122819	ChEBI
NSC-122819	ChEBI
Teniposido	ChEBI
Teniposidum	ChEBI
VM-26	ChEBI
Vumon	ChEBI
4'-Demethylepipodophyllotoxin 9-(4,6-O-2-thenylidene-b-D-glucopyranoside)	Generator
4'-Demethylepipodophyllotoxin 9-(4,6-O-2-thenylidene-β-D-glucopyranoside)	Generator
4'-Demethylepipodophyllotoxin-b-D-thenylidene glucoside	Generator
4'-Demethylepipodophyllotoxin-β-D-thenylidene glucoside	Generator
Bristol myers brand OF teniposide	HMDB
Bristol myers squibb brand OF teniposide	HMDB
Bristol-myers brand OF teniposide	HMDB
Bristol-myers squibb brand OF teniposide	HMDB
Demethyl epipodophyllotoxin thenylidine glucoside	HMDB
Teniposide, (5a alpha,9 alpha(s*))-isomer	HMDB
VM 26	HMDB

Chemical Formula

C₃₂H₃₂O₁₃S

Average Molecular Weight

656.654

Monoisotopic Molecular Weight

656.1563618

IUPAC Name

(10R,11R,15R,16S)-16-{[(4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-(thiophen-2-yl)-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one

Traditional Name

teniposide

CAS Registry Number

29767-20-2

SMILES

[H][C@]12COC(=O)[C@]1([H])[C@H](C1=CC(OC)=C(O)C(OC)=C1)C1=CC3=C(OCO3)C=C1[C@H]2O[C@@H]1O[C@]2([H])COC(O[C@@]2([H])[C@H](O)[C@H]1O)C1=CC=CS1

InChI Identifier

InChI=1S/C32H32O13S/c1-37-19-6-13(7-20(38-2)25(19)33)23-14-8-17-18(42-12-41-17)9-15(14)28(16-10-39-30(36)24(16)23)44-32-27(35)26(34)29-21(43-32)11-40-31(45-29)22-4-3-5-46-22/h3-9,16,21,23-24,26-29,31-35H,10-12H2,1-2H3/t16-,21+,23+,24-,26+,27+,28+,29+,31?,32-/m0/s1

InChI Key

NRUKOCRGYNPUPR-PSZSYXFXSA-N

Chemical Taxonomy

Description

Belongs to the class of inorganic compounds known as metalloid oxides. These are inorganic compounds containing an oxygen atom of an oxidation state of -2, in which the heaviest atom bonded to the oxygen is a metalloid.

Kingdom

Inorganic compounds

Super Class

Mixed metal/non-metal compounds

Class

Metalloid organides

Sub Class

Metalloid oxides

Direct Parent

Metalloid oxides

Alternative Parents

Substituents

Metalloid oxide
Inorganic oxide
Inorganic salt
Inorganic metalloid salt

Molecular Framework

Not Available

External Descriptors

silicon oxide (CHEBI:30563 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.06 g/L	Not Available
LogP	1.5	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.06 g/L	ALOGPS
logP	2.78	ALOGPS
logP	2.78	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	9.33	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	160.83 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	155.61 m³·mol⁻¹	ChemAxon
Polarizability	65.8 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	263.669	30932474
DeepCCS	[M+Na]+	237.688	30932474
AllCCS	[M+H]+	241.3	32859911
AllCCS	[M+H-H2O]+	240.5	32859911
AllCCS	[M+NH4]+	242.0	32859911
AllCCS	[M+Na]+	242.2	32859911
AllCCS	[M-H]-	226.7	32859911
AllCCS	[M+Na-2H]-	228.8	32859911
AllCCS	[M+HCOO]-	231.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.81 minutes	32390414
Predicted by Siyang on May 30, 2022	12.9983 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.6 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	75.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2747.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	194.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	197.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	182.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	98.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	410.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	537.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	424.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1135.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	509.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1523.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	384.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	338.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	285.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	148.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	73.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Teniposide	[H][C@]12COC(=O)[C@]1([H])[C@H](C1=CC(OC)=C(O)C(OC)=C1)C1=CC3=C(OCO3)C=C1[C@H]2O[C@@H]1O[C@]2([H])COC(O[C@@]2([H])[C@H](O)[C@H]1O)C1=CC=CS1	6439.8	Standard polar	33892256
Teniposide	[H][C@]12COC(=O)[C@]1([H])[C@H](C1=CC(OC)=C(O)C(OC)=C1)C1=CC3=C(OCO3)C=C1[C@H]2O[C@@H]1O[C@]2([H])COC(O[C@@]2([H])[C@H](O)[C@H]1O)C1=CC=CS1	4983.6	Standard non polar	33892256
Teniposide	[H][C@]12COC(=O)[C@]1([H])[C@H](C1=CC(OC)=C(O)C(OC)=C1)C1=CC3=C(OCO3)C=C1[C@H]2O[C@@H]1O[C@]2([H])COC(O[C@@]2([H])[C@H](O)[C@H]1O)C1=CC=CS1	5419.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Teniposide,1TMS,isomer #1	COC1=CC([C@@H]2C3=CC4=C(C=C3[C@@H](O[C@@H]3O[C@@H]5COC(C6=CC=CS6)O[C@H]5[C@H](O)[C@H]3O)[C@H]3COC(=O)[C@H]23)OCO4)=CC(OC)=C1O[Si](C)(C)C	5152.9	Semi standard non polar	33892256
Teniposide,1TMS,isomer #2	COC1=CC([C@@H]2C3=CC4=C(C=C3[C@@H](O[C@@H]3O[C@@H]5COC(C6=CC=CS6)O[C@H]5[C@H](O[Si](C)(C)C)[C@H]3O)[C@H]3COC(=O)[C@H]23)OCO4)=CC(OC)=C1O	5132.0	Semi standard non polar	33892256
Teniposide,1TMS,isomer #3	COC1=CC([C@@H]2C3=CC4=C(C=C3[C@@H](O[C@@H]3O[C@@H]5COC(C6=CC=CS6)O[C@H]5[C@H](O)[C@H]3O[Si](C)(C)C)[C@H]3COC(=O)[C@H]23)OCO4)=CC(OC)=C1O	5144.9	Semi standard non polar	33892256
Teniposide,2TMS,isomer #1	COC1=CC([C@@H]2C3=CC4=C(C=C3[C@@H](O[C@@H]3O[C@@H]5COC(C6=CC=CS6)O[C@H]5[C@H](O[Si](C)(C)C)[C@H]3O)[C@H]3COC(=O)[C@H]23)OCO4)=CC(OC)=C1O[Si](C)(C)C	5040.3	Semi standard non polar	33892256
Teniposide,2TMS,isomer #2	COC1=CC([C@@H]2C3=CC4=C(C=C3[C@@H](O[C@@H]3O[C@@H]5COC(C6=CC=CS6)O[C@H]5[C@H](O)[C@H]3O[Si](C)(C)C)[C@H]3COC(=O)[C@H]23)OCO4)=CC(OC)=C1O[Si](C)(C)C	5067.6	Semi standard non polar	33892256
Teniposide,2TMS,isomer #3	COC1=CC([C@@H]2C3=CC4=C(C=C3[C@@H](O[C@@H]3O[C@@H]5COC(C6=CC=CS6)O[C@H]5[C@H](O[Si](C)(C)C)[C@H]3O[Si](C)(C)C)[C@H]3COC(=O)[C@H]23)OCO4)=CC(OC)=C1O	5064.0	Semi standard non polar	33892256
Teniposide,3TMS,isomer #1	COC1=CC([C@@H]2C3=CC4=C(C=C3[C@@H](O[C@@H]3O[C@@H]5COC(C6=CC=CS6)O[C@H]5[C@H](O[Si](C)(C)C)[C@H]3O[Si](C)(C)C)[C@H]3COC(=O)[C@H]23)OCO4)=CC(OC)=C1O[Si](C)(C)C	5006.9	Semi standard non polar	33892256
Teniposide,1TBDMS,isomer #1	COC1=CC([C@@H]2C3=CC4=C(C=C3[C@@H](O[C@@H]3O[C@@H]5COC(C6=CC=CS6)O[C@H]5[C@H](O)[C@H]3O)[C@H]3COC(=O)[C@H]23)OCO4)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	5346.0	Semi standard non polar	33892256
Teniposide,1TBDMS,isomer #2	COC1=CC([C@@H]2C3=CC4=C(C=C3[C@@H](O[C@@H]3O[C@@H]5COC(C6=CC=CS6)O[C@H]5[C@H](O[Si](C)(C)C(C)(C)C)[C@H]3O)[C@H]3COC(=O)[C@H]23)OCO4)=CC(OC)=C1O	5311.8	Semi standard non polar	33892256
Teniposide,1TBDMS,isomer #3	COC1=CC([C@@H]2C3=CC4=C(C=C3[C@@H](O[C@@H]3O[C@@H]5COC(C6=CC=CS6)O[C@H]5[C@H](O)[C@H]3O[Si](C)(C)C(C)(C)C)[C@H]3COC(=O)[C@H]23)OCO4)=CC(OC)=C1O	5322.5	Semi standard non polar	33892256
Teniposide,2TBDMS,isomer #1	COC1=CC([C@@H]2C3=CC4=C(C=C3[C@@H](O[C@@H]3O[C@@H]5COC(C6=CC=CS6)O[C@H]5[C@H](O[Si](C)(C)C(C)(C)C)[C@H]3O)[C@H]3COC(=O)[C@H]23)OCO4)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	5396.1	Semi standard non polar	33892256
Teniposide,2TBDMS,isomer #2	COC1=CC([C@@H]2C3=CC4=C(C=C3[C@@H](O[C@@H]3O[C@@H]5COC(C6=CC=CS6)O[C@H]5[C@H](O)[C@H]3O[Si](C)(C)C(C)(C)C)[C@H]3COC(=O)[C@H]23)OCO4)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	5426.5	Semi standard non polar	33892256
Teniposide,2TBDMS,isomer #3	COC1=CC([C@@H]2C3=CC4=C(C=C3[C@@H](O[C@@H]3O[C@@H]5COC(C6=CC=CS6)O[C@H]5[C@H](O[Si](C)(C)C(C)(C)C)[C@H]3O[Si](C)(C)C(C)(C)C)[C@H]3COC(=O)[C@H]23)OCO4)=CC(OC)=C1O	5413.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Teniposide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a71-5785097000-98bde989946936a415b9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Teniposide GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Teniposide GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Teniposide GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Teniposide GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Teniposide GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Teniposide GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Teniposide GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Teniposide GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Teniposide GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Teniposide GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Teniposide GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Teniposide GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Teniposide GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Teniposide GC-MS ("Teniposide,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-11-02	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Teniposide 10V, Positive-QTOF	splash10-0zgi-0028609000-2103fbbc9230d944f190	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Teniposide 20V, Positive-QTOF	splash10-0ue9-0119500000-822a8a5e0ce6ead99756	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Teniposide 40V, Positive-QTOF	splash10-0ue9-2219200000-70925247141bc507a296	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Teniposide 10V, Negative-QTOF	splash10-0a5a-0518009000-b551c2cfb3b192aa0c97	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Teniposide 20V, Negative-QTOF	splash10-01ot-1409121000-a632ab719b28e6760ca1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Teniposide 40V, Negative-QTOF	splash10-0532-3009000000-a2fcbe218ec09c074476	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Teniposide 10V, Positive-QTOF	splash10-0kai-0069518000-4ca4220ba0f0b87931d5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Teniposide 20V, Positive-QTOF	splash10-001i-0029001000-8525d63245524aa711d7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Teniposide 40V, Positive-QTOF	splash10-0f80-0129000000-340326fd8e647fd49e25	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Teniposide 10V, Negative-QTOF	splash10-0a4i-0000009000-60dafc658503bb6aca9e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Teniposide 20V, Negative-QTOF	splash10-0a59-1002019000-4cb4998458f9b7c40d68	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Teniposide 40V, Negative-QTOF	splash10-001i-9103042000-d52ca9fb9e8848a4e5d7	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Teniposide Action Pathway		Not Available
Teniposide Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00444	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00444	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

31930

KEGG Compound ID

C11153

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Teniposide

METLIN ID

Not Available

PubChem Compound

34698

PDB ID

Not Available

ChEBI ID

75988

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

Enzyme Details

4. Cytochrome P450 3A5

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

5. DNA topoisomerase 2-alpha

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks
Gene Name:: TOP2A
Uniprot ID:: P11388
Molecular weight:: 174383.9

References

de Lucio B, Manuel V, Barrera-Rodriguez R: Characterization of human NSCLC cell line with innate etoposide-resistance mediated by cytoplasmic localization of topoisomerase II alpha. Cancer Sci. 2005 Nov;96(11):774-83. [PubMed:16271071 ]
Uesaka T, Shono T, Kuga D, Suzuki SO, Niiro H, Miyamoto K, Matsumoto K, Mizoguchi M, Ohta M, Iwaki T, Sasaki T: Enhanced expression of DNA topoisomerase II genes in human medulloblastoma and its possible association with etoposide sensitivity. J Neurooncol. 2007 Sep;84(2):119-29. Epub 2007 Mar 15. [PubMed:17361331 ]
Winnicka K, Bielawski K, Bielawska A: Cardiac glycosides in cancer research and cancer therapy. Acta Pol Pharm. 2006 Mar-Apr;63(2):109-15. [PubMed:17514873 ]
Faure P, Madelaine I: [Topoisomerases: therapeutic value]. Ann Pharm Fr. 1996;54(1):40-4. [PubMed:8702194 ]
Umanskaya ON, Ioudinkova ES, Razin SV, Bystritskiy AA: Inhibition of DNA topoisomerase II in living cells stimulates illegitimate recombination. Dokl Biochem Biophys. 2005 Nov-Dec;405:423-5. [PubMed:16480143 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Transporters

Enzyme Details

1. Multidrug resistance-associated protein 6

General function:: Involved in ATP binding
Specific function:: May participate directly in the active transport of drugs into subcellular organelles or influence drug distribution indirectly. Transports glutathione conjugates as leukotriene-c4 (LTC4) and N-ethylmaleimide S-glutathione (NEM-GS)
Gene Name:: ABCC6
Uniprot ID:: O95255
Molecular weight:: 164904.8

References

Belinsky MG, Chen ZS, Shchaveleva I, Zeng H, Kruh GD: Characterization of the drug resistance and transport properties of multidrug resistance protein 6 (MRP6, ABCC6). Cancer Res. 2002 Nov 1;62(21):6172-7. [PubMed:12414644 ]

Enzyme Details

2. ATP-binding cassette sub-family G member 2

General function:: Involved in ATP binding
Specific function:: Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from the brain. May be involved in brain-to-blood efflux. Appears to play a major role in the multidrug resistance phenotype of several cancer cell lines. When overexpressed, the transfected cells become resistant to mitoxantrone, daunorubicin and doxorubicin, display diminished intracellular accumulation of daunorubicin, and manifest an ATP- dependent increase in the efflux of rhodamine 123
Gene Name:: ABCG2
Uniprot ID:: Q9UNQ0
Molecular weight:: 72313.5

References

Allen JD, Van Dort SC, Buitelaar M, van Tellingen O, Schinkel AH: Mouse breast cancer resistance protein (Bcrp1/Abcg2) mediates etoposide resistance and transport, but etoposide oral availability is limited primarily by P-glycoprotein. Cancer Res. 2003 Mar 15;63(6):1339-44. [PubMed:12649196 ]

Showing metabocard for Teniposide (HMDB0014587)

MOL for HMDB0014587 (Teniposide)

3D MOL for HMDB0014587 (Teniposide)

3D SDF for HMDB0014587 (Teniposide)

3D-SDF for HMDB0014587 (Teniposide)

PDB for HMDB0014587 (Teniposide)

3D PDB for HMDB0014587 (Teniposide)

SMILES for HMDB0014587 (Teniposide)

INCHI for HMDB0014587 (Teniposide)

Structure for HMDB0014587 (Teniposide)

3D Structure for HMDB0014587 (Teniposide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

Transporters

References

References