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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:39 UTC

HMDB ID

HMDB0014518

Secondary Accession Numbers

HMDB14518

Metabolite Identification

Common Name

Treprostinil

Description

Treprostinil is only found in individuals that have used or taken this drug. It is a synthetic analogue of prostacyclin, used to treat pulmonary hypertension. Treprostinil is marketed as Remodulin®. [Wikipedia ]The major pharmacological actions of treprostinil are direct vasodilation of pulmonary and systemic arterial vascular beds and inhibition of platelet aggregation. In addition to treprostinil's direct vasodilatory effects, it also inhibits inflammatory cytokine. As a synthetic analogue of prostacyclin, it binds to the prostacyclin receptor, which subsequently induces the aforementioned downstream effects.

Structure

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


  Mrv0541 04191212122D          

 30 32  0  0  0  0            999 V2000
    2.9836   -1.8063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7068   -2.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4123   -1.7757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3947   -0.9509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6715   -0.5538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9660   -0.9815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2429   -0.5844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5373   -1.0121    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5550   -1.8369    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2782   -2.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7760   -2.1085    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7474   -0.7740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2769   -1.4516    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6538    0.2710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3593    0.6987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0824    0.3016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7936   -2.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0882   -3.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6350   -2.9639    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3405   -3.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0636   -2.9944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7691   -3.4221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4922   -3.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1977   -3.4527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7879    0.7293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1001   -0.5232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5479   -1.4692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6526   -2.1391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5726   -2.6617    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5197   -0.1872    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  1 10  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  1  0  0  0  0
  8 12  1  0  0  0  0
  9  8  1  0  0  0  0
 11  9  1  0  0  0  0
 11 13  1  0  0  0  0
 12 13  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 11 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 16 25  1  0  0  0  0
 16 26  2  0  0  0  0
 13 27  1  6  0  0  0
 19 28  1  6  0  0  0
  9 29  1  1  0  0  0
  8 30  1  1  0  0  0
M  END

HMDB0014518
     RDKit          3D
Treprostinil
 62 64  0  0  0  0  0  0  0  0999 V2000
    6.0001    1.9103   -0.8504 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8798    1.0321    0.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1011    0.4274    1.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9642   -0.4192    0.6137 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2065   -1.0079    1.7472 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0556   -1.8663    1.4199 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3835   -2.9601    0.5983 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7177   -1.2698    1.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6925   -0.3099    0.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3286    0.2696   -0.2527 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6993   -0.7472   -0.6602 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4394   -1.3700    0.4463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9134   -1.2580    0.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7189   -2.2479    0.9921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0897   -2.1344    0.9934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6647   -1.0011    0.4230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8721   -0.0095   -0.1335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4476    1.1131   -0.7000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8222    1.3602   -0.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4407    1.4823    0.5846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8082    1.4313    1.6633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8164    1.6667    0.6788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4971   -0.1548   -0.1189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6079    0.8683   -0.7149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6104    0.0530   -1.5611 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7655    1.0664   -2.2748 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5371    1.0260   -1.5505 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0860    2.2860   -1.3351 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4715    2.6865   -0.2910 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6954    2.3997   -1.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2952    1.3194   -1.4692 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7081    1.6427    0.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2416    0.2087   -0.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7866   -0.1436    1.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7017    1.2850    1.7612 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4734   -1.2327    0.0353 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3724    0.2237   -0.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8581   -0.2023    2.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9399   -1.6202    2.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9069   -2.4721    2.4469 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2935   -2.7532   -0.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4284   -0.7601    2.1560 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9614   -2.0879    1.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1764   -0.5799   -0.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2527    0.6207    0.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0588    0.9193    0.5480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1824   -1.5197   -1.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2540   -2.4927    0.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1310   -0.9765    1.4545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2270   -3.1140    1.4256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7358   -2.8969    1.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7333   -0.9480    0.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3783    0.6036   -1.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9837    2.3389   -1.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3189    2.2381    0.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1270    1.5276   -1.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0068    1.4147    0.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1919   -0.5856   -2.2570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6806    0.7817   -3.3571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1879    2.0868   -2.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2229    0.3885   -2.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6718    2.4631   -2.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 17 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 10  1  0
 25 11  1  0
 23 13  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  1
  7 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  1
 11 47  1  6
 12 48  1  0
 12 49  1  0
 14 50  1  0
 15 51  1  0
 16 52  1  0
 19 53  1  0
 19 54  1  0
 22 55  1  0
 24 56  1  0
 24 57  1  0
 25 58  1  6
 26 59  1  0
 26 60  1  0
 27 61  1  6
 28 62  1  0
M  END


  Mrv0541 04191212122D          

 30 32  0  0  0  0            999 V2000
    2.9836   -1.8063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7068   -2.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4123   -1.7757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3947   -0.9509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6715   -0.5538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9660   -0.9815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2429   -0.5844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5373   -1.0121    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5550   -1.8369    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2782   -2.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7760   -2.1085    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7474   -0.7740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2769   -1.4516    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6538    0.2710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3593    0.6987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0824    0.3016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7936   -2.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0882   -3.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6350   -2.9639    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3405   -3.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0636   -2.9944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7691   -3.4221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4922   -3.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1977   -3.4527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7879    0.7293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1001   -0.5232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5479   -1.4692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6526   -2.1391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5726   -2.6617    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5197   -0.1872    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  1 10  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  1  0  0  0  0
  8 12  1  0  0  0  0
  9  8  1  0  0  0  0
 11  9  1  0  0  0  0
 11 13  1  0  0  0  0
 12 13  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 11 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 16 25  1  0  0  0  0
 16 26  2  0  0  0  0
 13 27  1  6  0  0  0
 19 28  1  6  0  0  0
  9 29  1  1  0  0  0
  8 30  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0014518

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12C[C@@H](O)[C@H](CC[C@@H](O)CCCCC)[C@@]1([H])CC1=C(C2)C(OCC(O)=O)=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H34O5/c1-2-3-4-7-17(24)9-10-18-19-11-15-6-5-8-22(28-14-23(26)27)20(15)12-16(19)13-21(18)25/h5-6,8,16-19,21,24-25H,2-4,7,9-14H2,1H3,(H,26,27)/t16-,17-,18+,19-,21+/m0/s1

> <INCHI_KEY>
PAJMKGZZBBTTOY-ZFORQUDYSA-N

> <FORMULA>
C23H34O5

> <MOLECULAR_WEIGHT>
390.5131

> <EXACT_MASS>
390.240624198

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
45.744447680648875

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{[(1R,2R,3aS,9aS)-2-hydroxy-1-[(3S)-3-hydroxyoctyl]-1H,2H,3H,3aH,4H,9H,9aH-cyclopenta[b]naphthalen-5-yl]oxy}acetic acid

> <ALOGPS_LOGP>
3.53

> <JCHEM_LOGP>
4.004209447

> <ALOGPS_LOGS>
-4.73

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.93113067764028

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7604360397133454

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2797448535177374

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
108.00159999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.31e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
treprostinil

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014518
     RDKit          3D
Treprostinil
 62 64  0  0  0  0  0  0  0  0999 V2000
    6.0001    1.9103   -0.8504 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8798    1.0321    0.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1011    0.4274    1.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9642   -0.4192    0.6137 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2065   -1.0079    1.7472 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0556   -1.8663    1.4199 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3835   -2.9601    0.5983 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7177   -1.2698    1.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6925   -0.3099    0.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3286    0.2696   -0.2527 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6993   -0.7472   -0.6602 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4394   -1.3700    0.4463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9134   -1.2580    0.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7189   -2.2479    0.9921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0897   -2.1344    0.9934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6647   -1.0011    0.4230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8721   -0.0095   -0.1335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4476    1.1131   -0.7000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8222    1.3602   -0.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4407    1.4823    0.5846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8082    1.4313    1.6633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8164    1.6667    0.6788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4971   -0.1548   -0.1189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6079    0.8683   -0.7149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6104    0.0530   -1.5611 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7655    1.0664   -2.2748 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5371    1.0260   -1.5505 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0860    2.2860   -1.3351 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4715    2.6865   -0.2910 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6954    2.3997   -1.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2952    1.3194   -1.4692 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7081    1.6427    0.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2416    0.2087   -0.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7866   -0.1436    1.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7017    1.2850    1.7612 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4734   -1.2327    0.0353 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3724    0.2237   -0.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8581   -0.2023    2.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9399   -1.6202    2.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9069   -2.4721    2.4469 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2935   -2.7532   -0.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4284   -0.7601    2.1560 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9614   -2.0879    1.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1764   -0.5799   -0.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2527    0.6207    0.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0588    0.9193    0.5480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1824   -1.5197   -1.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2540   -2.4927    0.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1310   -0.9765    1.4545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2270   -3.1140    1.4256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7358   -2.8969    1.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7333   -0.9480    0.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3783    0.6036   -1.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9837    2.3389   -1.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3189    2.2381    0.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1270    1.5276   -1.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0068    1.4147    0.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1919   -0.5856   -2.2570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6806    0.7817   -3.3571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1879    2.0868   -2.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2229    0.3885   -2.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6718    2.4631   -2.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 17 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 10  1  0
 25 11  1  0
 23 13  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  1
  7 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  1
 11 47  1  6
 12 48  1  0
 12 49  1  0
 14 50  1  0
 15 51  1  0
 16 52  1  0
 19 53  1  0
 19 54  1  0
 22 55  1  0
 24 56  1  0
 24 57  1  0
 25 58  1  6
 26 59  1  0
 26 60  1  0
 27 61  1  6
 28 62  1  0
M  END

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0       5.569  -3.372   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.919  -4.113   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.236  -3.315   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.203  -1.775   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.853  -1.034   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.537  -1.832   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.187  -1.091   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.870  -1.889   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.903  -3.429   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.253  -4.170   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.449  -3.936   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.395  -1.445   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.517  -2.710   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.820   0.506   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.137   1.304   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.487   0.563   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.481  -5.475   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.165  -6.274   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.185  -5.533   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.502  -6.331   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.852  -5.590   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.169  -6.388   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -6.519  -5.647   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -7.836  -6.445   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      10.804   1.361   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       9.520  -0.977   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -1.023  -2.743   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -1.218  -3.993   0.000  0.00  0.00           O+0
HETATM   29  H   UNK     0       2.936  -4.969   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.837  -0.349   0.000  0.00  0.00           H+0
CONECT    1    2    6   10                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    1    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7   12    9   30                                             
CONECT    9   10    8   11   29                                             
CONECT   10    1    9                                                       
CONECT   11    9   13   17                                                  
CONECT   12    8   13                                                       
CONECT   13   11   12   27                                                  
CONECT   14    5   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   25   26                                                  
CONECT   17   11   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   28                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   16                                                            
CONECT   26   16                                                            
CONECT   27   13                                                            
CONECT   28   19                                                            
CONECT   29    9                                                            
CONECT   30    8                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

COMPND    HMDB0014518
HETATM    1  C1  UNL     1       6.000   1.910  -0.850  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.880   1.032   0.012  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.101   0.427   1.164  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.964  -0.419   0.614  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.206  -1.008   1.747  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.056  -1.866   1.420  1.00  0.00           C  
HETATM    7  O1  UNL     1       3.384  -2.960   0.598  1.00  0.00           O  
HETATM    8  C7  UNL     1       1.718  -1.270   1.177  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.692  -0.310   0.075  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.329   0.270  -0.253  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.699  -0.747  -0.660  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.439  -1.370   0.446  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.913  -1.258   0.436  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.719  -2.248   0.992  1.00  0.00           C  
HETATM   15  C14 UNL     1      -5.090  -2.134   0.993  1.00  0.00           C  
HETATM   16  C15 UNL     1      -5.665  -1.001   0.423  1.00  0.00           C  
HETATM   17  C16 UNL     1      -4.872  -0.010  -0.134  1.00  0.00           C  
HETATM   18  O2  UNL     1      -5.448   1.113  -0.700  1.00  0.00           O  
HETATM   19  C17 UNL     1      -6.822   1.360  -0.753  1.00  0.00           C  
HETATM   20  C18 UNL     1      -7.441   1.482   0.585  1.00  0.00           C  
HETATM   21  O3  UNL     1      -6.808   1.431   1.663  1.00  0.00           O  
HETATM   22  O4  UNL     1      -8.816   1.667   0.679  1.00  0.00           O  
HETATM   23  C19 UNL     1      -3.497  -0.155  -0.119  1.00  0.00           C  
HETATM   24  C20 UNL     1      -2.608   0.868  -0.715  1.00  0.00           C  
HETATM   25  C21 UNL     1      -1.610   0.053  -1.561  1.00  0.00           C  
HETATM   26  C22 UNL     1      -0.765   1.066  -2.275  1.00  0.00           C  
HETATM   27  C23 UNL     1       0.537   1.026  -1.550  1.00  0.00           C  
HETATM   28  O5  UNL     1       1.086   2.286  -1.335  1.00  0.00           O  
HETATM   29  H1  UNL     1       5.471   2.687  -0.291  1.00  0.00           H  
HETATM   30  H2  UNL     1       6.695   2.400  -1.590  1.00  0.00           H  
HETATM   31  H3  UNL     1       5.295   1.319  -1.469  1.00  0.00           H  
HETATM   32  H4  UNL     1       7.708   1.643   0.399  1.00  0.00           H  
HETATM   33  H5  UNL     1       7.242   0.209  -0.662  1.00  0.00           H  
HETATM   34  H6  UNL     1       6.787  -0.144   1.794  1.00  0.00           H  
HETATM   35  H7  UNL     1       5.702   1.285   1.761  1.00  0.00           H  
HETATM   36  H8  UNL     1       5.473  -1.233   0.035  1.00  0.00           H  
HETATM   37  H9  UNL     1       4.372   0.224  -0.017  1.00  0.00           H  
HETATM   38  H10 UNL     1       3.858  -0.202   2.441  1.00  0.00           H  
HETATM   39  H11 UNL     1       4.940  -1.620   2.340  1.00  0.00           H  
HETATM   40  H12 UNL     1       2.907  -2.472   2.447  1.00  0.00           H  
HETATM   41  H13 UNL     1       3.293  -2.753  -0.347  1.00  0.00           H  
HETATM   42  H14 UNL     1       1.428  -0.760   2.156  1.00  0.00           H  
HETATM   43  H15 UNL     1       0.961  -2.088   1.110  1.00  0.00           H  
HETATM   44  H16 UNL     1       2.176  -0.580  -0.868  1.00  0.00           H  
HETATM   45  H17 UNL     1       2.253   0.621   0.447  1.00  0.00           H  
HETATM   46  H18 UNL     1      -0.059   0.919   0.548  1.00  0.00           H  
HETATM   47  H19 UNL     1      -0.182  -1.520  -1.273  1.00  0.00           H  
HETATM   48  H20 UNL     1      -1.254  -2.493   0.419  1.00  0.00           H  
HETATM   49  H21 UNL     1      -1.131  -0.976   1.455  1.00  0.00           H  
HETATM   50  H22 UNL     1      -3.227  -3.114   1.426  1.00  0.00           H  
HETATM   51  H23 UNL     1      -5.736  -2.897   1.423  1.00  0.00           H  
HETATM   52  H24 UNL     1      -6.733  -0.948   0.430  1.00  0.00           H  
HETATM   53  H25 UNL     1      -7.378   0.604  -1.347  1.00  0.00           H  
HETATM   54  H26 UNL     1      -6.984   2.339  -1.266  1.00  0.00           H  
HETATM   55  H27 UNL     1      -9.319   2.238   0.025  1.00  0.00           H  
HETATM   56  H28 UNL     1      -3.127   1.528  -1.433  1.00  0.00           H  
HETATM   57  H29 UNL     1      -2.007   1.415   0.023  1.00  0.00           H  
HETATM   58  H30 UNL     1      -2.192  -0.586  -2.257  1.00  0.00           H  
HETATM   59  H31 UNL     1      -0.681   0.782  -3.357  1.00  0.00           H  
HETATM   60  H32 UNL     1      -1.188   2.087  -2.260  1.00  0.00           H  
HETATM   61  H33 UNL     1       1.223   0.389  -2.174  1.00  0.00           H  
HETATM   62  H34 UNL     1       1.672   2.463  -2.131  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3   32   33
CONECT    3    4   34   35
CONECT    4    5   36   37
CONECT    5    6   38   39
CONECT    6    7    8   40
CONECT    7   41
CONECT    8    9   42   43
CONECT    9   10   44   45
CONECT   10   11   27   46
CONECT   11   12   25   47
CONECT   12   13   48   49
CONECT   13   14   14   23
CONECT   14   15   50
CONECT   15   16   16   51
CONECT   16   17   52
CONECT   17   18   23   23
CONECT   18   19
CONECT   19   20   53   54
CONECT   20   21   21   22
CONECT   22   55
CONECT   23   24
CONECT   24   25   56   57
CONECT   25   26   58
CONECT   26   27   59   60
CONECT   27   28   61
CONECT   28   62
END

HMDB0014518
     RDKit          3D
Treprostinil
 62 64  0  0  0  0  0  0  0  0999 V2000
    6.0001    1.9103   -0.8504 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8798    1.0321    0.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1011    0.4274    1.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9642   -0.4192    0.6137 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2065   -1.0079    1.7472 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0556   -1.8663    1.4199 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3835   -2.9601    0.5983 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7177   -1.2698    1.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6925   -0.3099    0.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3286    0.2696   -0.2527 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6993   -0.7472   -0.6602 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4394   -1.3700    0.4463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9134   -1.2580    0.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7189   -2.2479    0.9921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0897   -2.1344    0.9934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6647   -1.0011    0.4230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8721   -0.0095   -0.1335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4476    1.1131   -0.7000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8222    1.3602   -0.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4407    1.4823    0.5846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8082    1.4313    1.6633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8164    1.6667    0.6788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4971   -0.1548   -0.1189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6079    0.8683   -0.7149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6104    0.0530   -1.5611 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7655    1.0664   -2.2748 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5371    1.0260   -1.5505 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0860    2.2860   -1.3351 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4715    2.6865   -0.2910 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6954    2.3997   -1.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2952    1.3194   -1.4692 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7081    1.6427    0.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2416    0.2087   -0.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7866   -0.1436    1.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7017    1.2850    1.7612 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4734   -1.2327    0.0353 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3724    0.2237   -0.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8581   -0.2023    2.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9399   -1.6202    2.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9069   -2.4721    2.4469 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2935   -2.7532   -0.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4284   -0.7601    2.1560 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9614   -2.0879    1.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1764   -0.5799   -0.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2527    0.6207    0.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0588    0.9193    0.5480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1824   -1.5197   -1.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2540   -2.4927    0.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1310   -0.9765    1.4545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2270   -3.1140    1.4256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7358   -2.8969    1.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7333   -0.9480    0.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3783    0.6036   -1.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9837    2.3389   -1.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3189    2.2381    0.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1270    1.5276   -1.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0068    1.4147    0.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1919   -0.5856   -2.2570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6806    0.7817   -3.3571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1879    2.0868   -2.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2229    0.3885   -2.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6718    2.4631   -2.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 17 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 10  1  0
 25 11  1  0
 23 13  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  1
  7 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  1
 11 47  1  6
 12 48  1  0
 12 49  1  0
 14 50  1  0
 15 51  1  0
 16 52  1  0
 19 53  1  0
 19 54  1  0
 22 55  1  0
 24 56  1  0
 24 57  1  0
 25 58  1  6
 26 59  1  0
 26 60  1  0
 27 61  1  6
 28 62  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Treprostinilo	ChEBI
Treprostinilum	ChEBI
Remodulin	Kegg
Orenitram	HMDB
Trepostinil sodium	HMDB
Treprostinil diolamine	HMDB
Treprostinil sodium	HMDB
UT-15	HMDB
UT-15C	HMDB
((1R,2R,3AS,9as)-2-hydroxy-1-((3S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cylopent(b)naphthalen-5-yl)oxy)acetate	HMDB
Treprostinil diethanolamine	HMDB
Treprostinil diolamin	HMDB

Chemical Formula

C₂₃H₃₄O₅

Average Molecular Weight

390.5131

Monoisotopic Molecular Weight

390.240624198

IUPAC Name

2-{[(1R,2R,3aS,9aS)-2-hydroxy-1-[(3S)-3-hydroxyoctyl]-1H,2H,3H,3aH,4H,9H,9aH-cyclopenta[b]naphthalen-5-yl]oxy}acetic acid

Traditional Name

treprostinil

CAS Registry Number

81846-19-7

SMILES

[H][C@]12C[C@@H](O)[C@H](CC[C@@H](O)CCCCC)[C@@]1([H])CC1=C(C2)C(OCC(O)=O)=CC=C1

InChI Identifier

InChI=1S/C23H34O5/c1-2-3-4-7-17(24)9-10-18-19-11-15-6-5-8-22(28-14-23(26)27)20(15)12-16(19)13-21(18)25/h5-6,8,16-19,21,24-25H,2-4,7,9-14H2,1H3,(H,26,27)/t16-,17-,18+,19-,21+/m0/s1

InChI Key

PAJMKGZZBBTTOY-ZFORQUDYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenoxyacetic acid derivatives. Phenoxyacetic acid derivatives are compounds containing an anisole where the methane group is linked to an acetic acid or a derivative.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenoxyacetic acid derivatives

Direct Parent

Phenoxyacetic acid derivatives

Alternative Parents

Substituents

Phenoxyacetate
Tetralin
Fatty alcohol
Alkyl aryl ether
Fatty acyl
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

carboxylic acid (CHEBI:50861 )
carbotricyclic compound (CHEBI:50861 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014518)
Membrane (HMDB: HMDB0014518)

Source

Exogenous

Exogenous (HMDB: HMDB0014518)

Process

Not Available

Role

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	0.0073 g/L	Not Available
LogP	4.1	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0073 g/L	ALOGPS
logP	3.53	ALOGPS
logP	4	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	3.76	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	108 m³·mol⁻¹	ChemAxon
Polarizability	45.74 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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
DarkChem	[M+H]+	195.754	31661259
DarkChem	[M-H]-	193.48	31661259
DeepCCS	[M-2H]-	230.387	30932474
DeepCCS	[M+Na]+	205.649	30932474
AllCCS	[M+H]+	199.1	32859911
AllCCS	[M+H-H2O]+	196.8	32859911
AllCCS	[M+NH4]+	201.3	32859911
AllCCS	[M+Na]+	201.9	32859911
AllCCS	[M-H]-	198.9	32859911
AllCCS	[M+Na-2H]-	200.2	32859911
AllCCS	[M+HCOO]-	201.8	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.	7.45 minutes	32390414
Predicted by Siyang on May 30, 2022	15.5552 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.17 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	52.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2726.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	289.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	212.4 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	432.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	764.4 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	649.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	105.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1315.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	601.7 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	1699.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	401.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	429.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	273.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	183.5 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	19.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Treprostinil	[H][C@]12C[C@@H](O)[C@H](CC[C@@H](O)CCCCC)[C@@]1([H])CC1=C(C2)C(OCC(O)=O)=CC=C1	4984.1	Standard polar	33892256
Treprostinil	[H][C@]12C[C@@H](O)[C@H](CC[C@@H](O)CCCCC)[C@@]1([H])CC1=C(C2)C(OCC(O)=O)=CC=C1	3230.3	Standard non polar	33892256
Treprostinil	[H][C@]12C[C@@H](O)[C@H](CC[C@@H](O)CCCCC)[C@@]1([H])CC1=C(C2)C(OCC(O)=O)=CC=C1	3377.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Treprostinil,1TMS,isomer #1	CCCCC[C@H](O)CC[C@@H]1[C@H]2CC3=CC=CC(OCC(=O)O)=C3C[C@H]2C[C@H]1O[Si](C)(C)C	3206.2	Semi standard non polar	33892256
Treprostinil,1TMS,isomer #2	CCCCC[C@@H](CC[C@@H]1[C@H]2CC3=CC=CC(OCC(=O)O)=C3C[C@H]2C[C@H]1O)O[Si](C)(C)C	3239.1	Semi standard non polar	33892256
Treprostinil,1TMS,isomer #3	CCCCC[C@H](O)CC[C@@H]1[C@H]2CC3=CC=CC(OCC(=O)O[Si](C)(C)C)=C3C[C@H]2C[C@H]1O	3189.2	Semi standard non polar	33892256
Treprostinil,2TMS,isomer #1	CCCCC[C@@H](CC[C@@H]1[C@H]2CC3=CC=CC(OCC(=O)O)=C3C[C@H]2C[C@H]1O[Si](C)(C)C)O[Si](C)(C)C	3219.4	Semi standard non polar	33892256
Treprostinil,2TMS,isomer #2	CCCCC[C@H](O)CC[C@@H]1[C@H]2CC3=CC=CC(OCC(=O)O[Si](C)(C)C)=C3C[C@H]2C[C@H]1O[Si](C)(C)C	3183.4	Semi standard non polar	33892256
Treprostinil,2TMS,isomer #3	CCCCC[C@@H](CC[C@@H]1[C@H]2CC3=CC=CC(OCC(=O)O[Si](C)(C)C)=C3C[C@H]2C[C@H]1O)O[Si](C)(C)C	3241.5	Semi standard non polar	33892256
Treprostinil,3TMS,isomer #1	CCCCC[C@@H](CC[C@@H]1[C@H]2CC3=CC=CC(OCC(=O)O[Si](C)(C)C)=C3C[C@H]2C[C@H]1O[Si](C)(C)C)O[Si](C)(C)C	3234.8	Semi standard non polar	33892256
Treprostinil,1TBDMS,isomer #1	CCCCC[C@H](O)CC[C@@H]1[C@H]2CC3=CC=CC(OCC(=O)O)=C3C[C@H]2C[C@H]1O[Si](C)(C)C(C)(C)C	3414.2	Semi standard non polar	33892256
Treprostinil,1TBDMS,isomer #2	CCCCC[C@@H](CC[C@@H]1[C@H]2CC3=CC=CC(OCC(=O)O)=C3C[C@H]2C[C@H]1O)O[Si](C)(C)C(C)(C)C	3462.0	Semi standard non polar	33892256
Treprostinil,1TBDMS,isomer #3	CCCCC[C@H](O)CC[C@@H]1[C@H]2CC3=CC=CC(OCC(=O)O[Si](C)(C)C(C)(C)C)=C3C[C@H]2C[C@H]1O	3423.0	Semi standard non polar	33892256
Treprostinil,2TBDMS,isomer #1	CCCCC[C@@H](CC[C@@H]1[C@H]2CC3=CC=CC(OCC(=O)O)=C3C[C@H]2C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3657.2	Semi standard non polar	33892256
Treprostinil,2TBDMS,isomer #2	CCCCC[C@H](O)CC[C@@H]1[C@H]2CC3=CC=CC(OCC(=O)O[Si](C)(C)C(C)(C)C)=C3C[C@H]2C[C@H]1O[Si](C)(C)C(C)(C)C	3645.0	Semi standard non polar	33892256
Treprostinil,2TBDMS,isomer #3	CCCCC[C@@H](CC[C@@H]1[C@H]2CC3=CC=CC(OCC(=O)O[Si](C)(C)C(C)(C)C)=C3C[C@H]2C[C@H]1O)O[Si](C)(C)C(C)(C)C	3676.8	Semi standard non polar	33892256
Treprostinil,3TBDMS,isomer #1	CCCCC[C@@H](CC[C@@H]1[C@H]2CC3=CC=CC(OCC(=O)O[Si](C)(C)C(C)(C)C)=C3C[C@H]2C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3870.5	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 - Treprostinil GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fxw-4197000000-f2c1b87e66efdc91b50e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Treprostinil GC-MS (3 TMS) - 70eV, Positive	splash10-0076-7210190000-21ff7ee6208bb7b64a7d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Treprostinil GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - Treprostinil 10V, Positive-QTOF	splash10-05fu-0019000000-07524b6871c3cbeb6247	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Treprostinil 20V, Positive-QTOF	splash10-05fr-4259000000-db102057e93677a67e3f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Treprostinil 40V, Positive-QTOF	splash10-0abc-9384000000-69f5a3403f3e6092f791	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Treprostinil 10V, Negative-QTOF	splash10-000i-0009000000-69eb101db3001417d4da	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Treprostinil 20V, Negative-QTOF	splash10-009i-1009000000-b4d4f7ffb8b39aec097f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Treprostinil 40V, Negative-QTOF	splash10-00fs-7396000000-b9875923704c71aa676a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Treprostinil 10V, Negative-QTOF	splash10-000i-0029000000-23c56b7cb115f5b54c17	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Treprostinil 20V, Negative-QTOF	splash10-0079-3089000000-21aeb3a71382c50e5572	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Treprostinil 40V, Negative-QTOF	splash10-00b9-4092000000-14472fa2804e67f69f32	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Treprostinil 10V, Positive-QTOF	splash10-0abc-0019000000-b56cc01da374c6cef594	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Treprostinil 20V, Positive-QTOF	splash10-0a4i-2069000000-1c37a2baaf68029ce216	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Treprostinil 40V, Positive-QTOF	splash10-0002-4092000000-e68c8ee6cce6cffc29ab	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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 DB00374	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00374	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00374

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5293353

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Treprostinil

METLIN ID

Not Available

PubChem Compound

6918140

PDB ID

Not Available

ChEBI ID

50861

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. P2Y purinoceptor 12

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Receptor for ADP and ATP coupled to G-proteins that inhibit the adenylyl cyclase second messenger system. Not activated by UDP and UTP. Involved in platelets aggregation
Gene Name:: P2RY12
Uniprot ID:: Q9H244
Molecular weight:: 39438.4

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Enzyme Details

2. Peroxisome proliferator-activated receptor delta

General function:: Involved in DNA binding
Specific function:: Ligand-activated transcription factor. Receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Has a preference for poly-unsaturated fatty acids, such as gamma-linoleic acid and eicosapentanoic acid. Once activated by a ligand, the receptor binds to promoter elements of target genes. Regulates the peroxisomal beta-oxidation pathway of fatty acids. Functions as transcription activator for the acyl-CoA oxidase gene. Decreases expression of NPC1L1 once activated by a ligand
Gene Name:: PPARD
Uniprot ID:: Q03181
Molecular weight:: 49903.0

References

Ali FY, Egan K, FitzGerald GA, Desvergne B, Wahli W, Bishop-Bailey D, Warner TD, Mitchell JA: Role of prostacyclin versus peroxisome proliferator-activated receptor beta receptors in prostacyclin sensing by lung fibroblasts. Am J Respir Cell Mol Biol. 2006 Feb;34(2):242-6. Epub 2005 Oct 20. [PubMed:16239641 ]

Enzyme Details

3. Prostacyclin receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Receptor for prostacyclin (prostaglandin I2 or PGI2). The activity of this receptor is mediated by G(s) proteins which activate adenylate cyclase
Gene Name:: PTGIR
Uniprot ID:: P43119
Molecular weight:: 40955.5

References

Falcetti E, Hall SM, Phillips PG, Patel J, Morrell NW, Haworth SG, Clapp LH: Smooth muscle proliferation and role of the prostacyclin (IP) receptor in idiopathic pulmonary arterial hypertension. Am J Respir Crit Care Med. 2010 Nov 1;182(9):1161-70. doi: 10.1164/rccm.201001-0011OC. Epub 2010 Jul 9. [PubMed:20622039 ]
Sprague RS, Bowles EA, Hanson MS, DuFaux EA, Sridharan M, Adderley S, Ellsworth ML, Stephenson AH: Prostacyclin analogs stimulate receptor-mediated cAMP synthesis and ATP release from rabbit and human erythrocytes. Microcirculation. 2008 Jul;15(5):461-71. doi: 10.1080/10739680701833804. [PubMed:18574748 ]
Olschewski H, Rose F, Schermuly R, Ghofrani HA, Enke B, Olschewski A, Seeger W: Prostacyclin and its analogues in the treatment of pulmonary hypertension. Pharmacol Ther. 2004 May;102(2):139-53. [PubMed:15163595 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Treprostinil (HMDB0014518)

MOL for HMDB0014518 (Treprostinil)

3D MOL for HMDB0014518 (Treprostinil)

3D SDF for HMDB0014518 (Treprostinil)

3D-SDF for HMDB0014518 (Treprostinil)

PDB for HMDB0014518 (Treprostinil)

3D PDB for HMDB0014518 (Treprostinil)

SMILES for HMDB0014518 (Treprostinil)

INCHI for HMDB0014518 (Treprostinil)

Structure for HMDB0014518 (Treprostinil)

3D Structure for HMDB0014518 (Treprostinil)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References