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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:02 UTC

HMDB ID

HMDB0015587

Secondary Accession Numbers

HMDB15587

Metabolite Identification

Common Name

Cyproterone

Description

Cyproterone, also known as ciproterona or novo-cyproterone, belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. Cyproterone is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

4839
  Mrv0541 09041214512D          

 31 35  0  0  1  0            999 V2000
    7.0790    0.9766    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4286    0.5660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8121   -1.8482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5936    1.0218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6989   -0.6170    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0089   -0.2187    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6862   -1.4469    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5747    0.5947    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2967    1.0042    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0089    0.5782    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4017   -1.8674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6796   -2.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2967   -0.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5747   -0.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9674    1.1531    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1293    1.8120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3890   -0.2187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3094    1.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0089   -1.0154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6989    0.9766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8817    0.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1205   -1.4524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3890    0.5782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1141   -0.6224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2425    1.4840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1668    2.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0139   -0.8560    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0488   -1.4394    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8162    1.3734    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5610    0.2594    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7184   -2.4206    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 23  1  0  0  0  0
 15  2  1  6  0  0  0
  3 22  2  0  0  0  0
  4 25  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5 17  1  0  0  0  0
  5 19  1  1  0  0  0
  6 10  1  0  0  0  0
  6 13  1  0  0  0  0
  6 27  1  6  0  0  0
  7 11  1  0  0  0  0
  7 12  1  0  0  0  0
  7 28  1  1  0  0  0
  8  9  1  0  0  0  0
  8 14  1  0  0  0  0
  8 15  1  0  0  0  0
  8 21  1  1  0  0  0
  9 10  1  0  0  0  0
  9 16  1  0  0  0  0
  9 29  1  6  0  0  0
 10 20  1  0  0  0  0
 10 30  1  1  0  0  0
 11 12  1  0  0  0  0
 11 22  1  0  0  0  0
 11 31  1  1  0  0  0
 13 14  1  0  0  0  0
 15 18  1  0  0  0  0
 15 25  1  0  0  0  0
 16 18  1  0  0  0  0
 17 23  1  0  0  0  0
 17 24  2  0  0  0  0
 20 23  2  0  0  0  0
 22 24  1  0  0  0  0
 25 26  1  0  0  0  0
M  END

HMDB0015587
     RDKit          3D
Cyproterone
 53 57  0  0  0  0  0  0  0  0999 V2000
   -5.2425    0.8191    1.2552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2433    0.6594    0.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3382    1.4399   -0.7789 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2130   -0.4085    0.2275 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4077   -1.1555    1.3939 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4140   -1.2744   -1.0243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1305   -1.0466   -1.8397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1460   -0.8495   -0.7640 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1782   -0.2616   -1.1385 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8692   -1.0146   -2.1947 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1656   -1.0613   -2.2790 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0074   -1.9649   -3.5486 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0068   -0.3503   -1.2876 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3101   -0.2543   -1.4565 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1156    0.4549   -0.4503 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0753    1.1317   -0.8323 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6771    0.2765    0.9603 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0732   -1.0879    1.3603 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2159    0.0873    1.1159 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3878    0.2839   -0.1015 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2524    1.7922   -0.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0013   -0.2851    0.1247 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3552    0.3260    1.3106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0801   -0.0267    1.4989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8189    0.1077    0.1909 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7735    1.5278   -0.2389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7751    0.5297    2.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1049    0.1408    1.0216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6435    1.8445    1.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3942   -1.3206    1.4557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4659   -2.3283   -0.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2739   -0.9720   -1.6169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2473   -0.2280   -2.5497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9583   -2.0147   -2.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9757   -1.7902   -0.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0038    0.7695   -1.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2890   -1.5684   -2.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7490   -0.7000   -2.3534 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3012    0.7493    1.7246 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2724   -1.4729    2.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0769   -1.8522    0.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8271    0.5516    2.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1941    2.2402    0.6984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4629    2.0731   -0.9970 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2082    2.1988   -0.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1663   -1.3781    0.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4682    1.4225    1.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8966   -0.0819    2.2179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1187   -1.1202    1.7763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5009    0.6125    2.2984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7795    2.0080   -0.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4626    2.1098    0.4080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0908    1.7119   -1.2871 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  1
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  6
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  6
 25  4  1  0
 25  8  1  0
 22  9  1  0
 20 13  1  0
 19 17  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  1
  9 36  1  6
 10 37  1  0
 14 38  1  0
 17 39  1  1
 18 40  1  0
 18 41  1  0
 19 42  1  1
 21 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  1
 23 47  1  0
 23 48  1  0
 24 49  1  0
 24 50  1  0
 26 51  1  0
 26 52  1  0
 26 53  1  0
M  END

4839
  Mrv0541 09041214512D          

 31 35  0  0  1  0            999 V2000
    7.0790    0.9766    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4286    0.5660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8121   -1.8482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5936    1.0218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6989   -0.6170    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0089   -0.2187    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6862   -1.4469    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5747    0.5947    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2967    1.0042    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0089    0.5782    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4017   -1.8674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6796   -2.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2967   -0.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5747   -0.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9674    1.1531    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1293    1.8120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3890   -0.2187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3094    1.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0089   -1.0154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6989    0.9766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8817    0.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1205   -1.4524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3890    0.5782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1141   -0.6224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2425    1.4840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1668    2.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0139   -0.8560    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0488   -1.4394    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8162    1.3734    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5610    0.2594    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7184   -2.4206    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 23  1  0  0  0  0
 15  2  1  6  0  0  0
  3 22  2  0  0  0  0
  4 25  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5 17  1  0  0  0  0
  5 19  1  1  0  0  0
  6 10  1  0  0  0  0
  6 13  1  0  0  0  0
  6 27  1  6  0  0  0
  7 11  1  0  0  0  0
  7 12  1  0  0  0  0
  7 28  1  1  0  0  0
  8  9  1  0  0  0  0
  8 14  1  0  0  0  0
  8 15  1  0  0  0  0
  8 21  1  1  0  0  0
  9 10  1  0  0  0  0
  9 16  1  0  0  0  0
  9 29  1  6  0  0  0
 10 20  1  0  0  0  0
 10 30  1  1  0  0  0
 11 12  1  0  0  0  0
 11 22  1  0  0  0  0
 11 31  1  1  0  0  0
 13 14  1  0  0  0  0
 15 18  1  0  0  0  0
 15 25  1  0  0  0  0
 16 18  1  0  0  0  0
 17 23  1  0  0  0  0
 17 24  2  0  0  0  0
 20 23  2  0  0  0  0
 22 24  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015587

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12C[C@]1([H])[C@@]1(C)C(=CC2=O)C(Cl)=C[C@@]2([H])[C@]3([H])CC[C@](O)(C(C)=O)[C@@]3(C)CC[C@]12[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H27ClO3/c1-11(24)22(26)7-5-14-12-9-18(23)17-10-19(25)13-8-16(13)21(17,3)15(12)4-6-20(14,22)2/h9-10,12-16,26H,4-8H2,1-3H3/t12-,13+,14-,15-,16-,20-,21-,22-/m0/s1

> <INCHI_KEY>
DUSHUSLJJMDGTE-ZJPMUUANSA-N

> <FORMULA>
C22H27ClO3

> <MOLECULAR_WEIGHT>
374.901

> <EXACT_MASS>
374.164872437

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
40.66923911970898

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,3S,5R,11R,12S,15R,16S)-15-acetyl-9-chloro-15-hydroxy-2,16-dimethylpentacyclo[9.7.0.0²,⁸.0³,⁵.0¹²,¹⁶]octadeca-7,9-dien-6-one

> <ALOGPS_LOGP>
3.37

> <JCHEM_LOGP>
3.197731527

> <ALOGPS_LOGS>
-4.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.613097039979067

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.699100061469213

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8052043581291803

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
102.65799999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.65e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cyproterone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015587
     RDKit          3D
Cyproterone
 53 57  0  0  0  0  0  0  0  0999 V2000
   -5.2425    0.8191    1.2552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2433    0.6594    0.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3382    1.4399   -0.7789 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2130   -0.4085    0.2275 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4077   -1.1555    1.3939 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4140   -1.2744   -1.0243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1305   -1.0466   -1.8397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1460   -0.8495   -0.7640 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1782   -0.2616   -1.1385 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8692   -1.0146   -2.1947 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1656   -1.0613   -2.2790 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0074   -1.9649   -3.5486 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0068   -0.3503   -1.2876 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3101   -0.2543   -1.4565 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1156    0.4549   -0.4503 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0753    1.1317   -0.8323 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6771    0.2765    0.9603 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0732   -1.0879    1.3603 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2159    0.0873    1.1159 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3878    0.2839   -0.1015 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2524    1.7922   -0.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0013   -0.2851    0.1247 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3552    0.3260    1.3106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0801   -0.0267    1.4989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8189    0.1077    0.1909 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7735    1.5278   -0.2389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7751    0.5297    2.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1049    0.1408    1.0216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6435    1.8445    1.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3942   -1.3206    1.4557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4659   -2.3283   -0.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2739   -0.9720   -1.6169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2473   -0.2280   -2.5497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9583   -2.0147   -2.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9757   -1.7902   -0.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0038    0.7695   -1.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2890   -1.5684   -2.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7490   -0.7000   -2.3534 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3012    0.7493    1.7246 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2724   -1.4729    2.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0769   -1.8522    0.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8271    0.5516    2.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1941    2.2402    0.6984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4629    2.0731   -0.9970 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2082    2.1988   -0.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1663   -1.3781    0.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4682    1.4225    1.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8966   -0.0819    2.2179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1187   -1.1202    1.7763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5009    0.6125    2.2984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7795    2.0080   -0.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4626    2.1098    0.4080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0908    1.7119   -1.2871 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  1
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  6
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  6
 25  4  1  0
 25  8  1  0
 22  9  1  0
 20 13  1  0
 19 17  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  1
  9 36  1  6
 10 37  1  0
 14 38  1  0
 17 39  1  1
 18 40  1  0
 18 41  1  0
 19 42  1  1
 21 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  1
 23 47  1  0
 23 48  1  0
 24 49  1  0
 24 50  1  0
 26 51  1  0
 26 52  1  0
 26 53  1  0
M  END

HEADER    PROTEIN                                 04-SEP-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 4839                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-12         0                                  
HETATM    1 Cl   UNK     0      13.214   1.823   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0       4.533   1.057   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      14.583  -3.450   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.975   1.907   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.638  -1.152   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.350  -0.408   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.614  -2.701   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.673   1.110   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.021   1.875   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.350   1.079   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.950  -3.486   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.602  -4.251   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.021  -1.203   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.673  -0.439   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.539   2.152   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.708   3.382   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.926  -0.408   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.178   3.554   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.350  -1.895   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.638   1.823   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.379   0.377   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.292  -2.711   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.926   1.079   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.280  -1.162   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.186   2.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.045   4.251   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0       9.359  -1.598   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       9.424  -2.687   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       8.990   2.564   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      10.381   0.484   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0      12.541  -4.518   0.000  0.00  0.00           H+0
CONECT    1   23                                                            
CONECT    2   15                                                            
CONECT    3   22                                                            
CONECT    4   25                                                            
CONECT    5    6    7   17   19                                             
CONECT    6    5   10   13   27                                             
CONECT    7    5   11   12   28                                             
CONECT    8    9   14   15   21                                             
CONECT    9    8   10   16   29                                             
CONECT   10    6    9   20   30                                             
CONECT   11    7   12   22   31                                             
CONECT   12    7   11                                                       
CONECT   13    6   14                                                       
CONECT   14    8   13                                                       
CONECT   15    2    8   18   25                                             
CONECT   16    9   18                                                       
CONECT   17    5   23   24                                                  
CONECT   18   15   16                                                       
CONECT   19    5                                                            
CONECT   20   10   23                                                       
CONECT   21    8                                                            
CONECT   22    3   11   24                                                  
CONECT   23    1   17   20                                                  
CONECT   24   17   22                                                       
CONECT   25    4   15   26                                                  
CONECT   26   25                                                            
CONECT   27    6                                                            
CONECT   28    7                                                            
CONECT   29    9                                                            
CONECT   30   10                                                            
CONECT   31   11                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

COMPND    HMDB0015587
HETATM    1  C1  UNL     1      -5.243   0.819   1.255  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.243   0.659   0.149  1.00  0.00           C  
HETATM    3  O1  UNL     1      -4.338   1.440  -0.779  1.00  0.00           O  
HETATM    4  C3  UNL     1      -3.213  -0.409   0.227  1.00  0.00           C  
HETATM    5  O2  UNL     1      -3.408  -1.155   1.394  1.00  0.00           O  
HETATM    6  C4  UNL     1      -3.414  -1.274  -1.024  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.130  -1.047  -1.840  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.146  -0.850  -0.764  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.178  -0.262  -1.139  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.869  -1.015  -2.195  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.166  -1.061  -2.279  1.00  0.00           C  
HETATM   12 CL1  UNL     1       3.007  -1.965  -3.549  1.00  0.00          CL  
HETATM   13  C10 UNL     1       3.007  -0.350  -1.288  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.310  -0.254  -1.456  1.00  0.00           C  
HETATM   15  C12 UNL     1       5.116   0.455  -0.450  1.00  0.00           C  
HETATM   16  O3  UNL     1       6.075   1.132  -0.832  1.00  0.00           O  
HETATM   17  C13 UNL     1       4.677   0.277   0.960  1.00  0.00           C  
HETATM   18  C14 UNL     1       4.073  -1.088   1.360  1.00  0.00           C  
HETATM   19  C15 UNL     1       3.216   0.087   1.116  1.00  0.00           C  
HETATM   20  C16 UNL     1       2.388   0.284  -0.102  1.00  0.00           C  
HETATM   21  C17 UNL     1       2.252   1.792  -0.304  1.00  0.00           C  
HETATM   22  C18 UNL     1       1.001  -0.285   0.125  1.00  0.00           C  
HETATM   23  C19 UNL     1       0.355   0.326   1.311  1.00  0.00           C  
HETATM   24  C20 UNL     1      -1.080  -0.027   1.499  1.00  0.00           C  
HETATM   25  C21 UNL     1      -1.819   0.108   0.191  1.00  0.00           C  
HETATM   26  C22 UNL     1      -1.773   1.528  -0.239  1.00  0.00           C  
HETATM   27  H1  UNL     1      -4.775   0.530   2.230  1.00  0.00           H  
HETATM   28  H2  UNL     1      -6.105   0.141   1.022  1.00  0.00           H  
HETATM   29  H3  UNL     1      -5.644   1.845   1.277  1.00  0.00           H  
HETATM   30  H4  UNL     1      -4.394  -1.321   1.456  1.00  0.00           H  
HETATM   31  H5  UNL     1      -3.466  -2.328  -0.665  1.00  0.00           H  
HETATM   32  H6  UNL     1      -4.274  -0.972  -1.617  1.00  0.00           H  
HETATM   33  H7  UNL     1      -2.247  -0.228  -2.550  1.00  0.00           H  
HETATM   34  H8  UNL     1      -1.958  -2.015  -2.389  1.00  0.00           H  
HETATM   35  H9  UNL     1      -0.976  -1.790  -0.229  1.00  0.00           H  
HETATM   36  H10 UNL     1      -0.004   0.770  -1.504  1.00  0.00           H  
HETATM   37  H11 UNL     1       0.289  -1.568  -2.955  1.00  0.00           H  
HETATM   38  H12 UNL     1       4.749  -0.700  -2.353  1.00  0.00           H  
HETATM   39  H13 UNL     1       5.301   0.749   1.725  1.00  0.00           H  
HETATM   40  H14 UNL     1       4.272  -1.473   2.361  1.00  0.00           H  
HETATM   41  H15 UNL     1       4.077  -1.852   0.533  1.00  0.00           H  
HETATM   42  H16 UNL     1       2.827   0.552   2.080  1.00  0.00           H  
HETATM   43  H17 UNL     1       2.194   2.240   0.698  1.00  0.00           H  
HETATM   44  H18 UNL     1       1.463   2.073  -0.997  1.00  0.00           H  
HETATM   45  H19 UNL     1       3.208   2.199  -0.749  1.00  0.00           H  
HETATM   46  H20 UNL     1       1.166  -1.378   0.359  1.00  0.00           H  
HETATM   47  H21 UNL     1       0.468   1.423   1.405  1.00  0.00           H  
HETATM   48  H22 UNL     1       0.897  -0.082   2.218  1.00  0.00           H  
HETATM   49  H23 UNL     1      -1.119  -1.120   1.776  1.00  0.00           H  
HETATM   50  H24 UNL     1      -1.501   0.613   2.298  1.00  0.00           H  
HETATM   51  H25 UNL     1      -0.780   2.008  -0.089  1.00  0.00           H  
HETATM   52  H26 UNL     1      -2.463   2.110   0.408  1.00  0.00           H  
HETATM   53  H27 UNL     1      -2.091   1.712  -1.287  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3    3    4
CONECT    4    5    6   25
CONECT    5   30
CONECT    6    7   31   32
CONECT    7    8   33   34
CONECT    8    9   25   35
CONECT    9   10   22   36
CONECT   10   11   11   37
CONECT   11   12   13
CONECT   13   14   14   20
CONECT   14   15   38
CONECT   15   16   16   17
CONECT   17   18   19   39
CONECT   18   19   40   41
CONECT   19   20   42
CONECT   20   21   22
CONECT   21   43   44   45
CONECT   22   23   46
CONECT   23   24   47   48
CONECT   24   25   49   50
CONECT   25   26
CONECT   26   51   52   53
END

HMDB0015587
     RDKit          3D
Cyproterone
 53 57  0  0  0  0  0  0  0  0999 V2000
   -5.2425    0.8191    1.2552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2433    0.6594    0.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3382    1.4399   -0.7789 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2130   -0.4085    0.2275 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4077   -1.1555    1.3939 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4140   -1.2744   -1.0243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1305   -1.0466   -1.8397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1460   -0.8495   -0.7640 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1782   -0.2616   -1.1385 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8692   -1.0146   -2.1947 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1656   -1.0613   -2.2790 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0074   -1.9649   -3.5486 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0068   -0.3503   -1.2876 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3101   -0.2543   -1.4565 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1156    0.4549   -0.4503 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0753    1.1317   -0.8323 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6771    0.2765    0.9603 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0732   -1.0879    1.3603 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2159    0.0873    1.1159 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3878    0.2839   -0.1015 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2524    1.7922   -0.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0013   -0.2851    0.1247 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3552    0.3260    1.3106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0801   -0.0267    1.4989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8189    0.1077    0.1909 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7735    1.5278   -0.2389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7751    0.5297    2.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1049    0.1408    1.0216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6435    1.8445    1.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3942   -1.3206    1.4557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4659   -2.3283   -0.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2739   -0.9720   -1.6169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2473   -0.2280   -2.5497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9583   -2.0147   -2.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9757   -1.7902   -0.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0038    0.7695   -1.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2890   -1.5684   -2.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7490   -0.7000   -2.3534 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3012    0.7493    1.7246 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2724   -1.4729    2.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0769   -1.8522    0.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8271    0.5516    2.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1941    2.2402    0.6984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4629    2.0731   -0.9970 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2082    2.1988   -0.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1663   -1.3781    0.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4682    1.4225    1.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8966   -0.0819    2.2179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1187   -1.1202    1.7763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5009    0.6125    2.2984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7795    2.0080   -0.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4626    2.1098    0.4080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0908    1.7119   -1.2871 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  1
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  6
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  6
 25  4  1  0
 25  8  1  0
 22  9  1  0
 20 13  1  0
 19 17  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  1
  9 36  1  6
 10 37  1  0
 14 38  1  0
 17 39  1  1
 18 40  1  0
 18 41  1  0
 19 42  1  1
 21 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  1
 23 47  1  0
 23 48  1  0
 24 49  1  0
 24 50  1  0
 26 51  1  0
 26 52  1  0
 26 53  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6-Chlor-delta(6)-1,2-alpha-methylen-17-alpha-hydroxyprogesteron	ChEBI
Apo-cyproterone	ChEBI
Ciproterona	ChEBI
Ciproterone	ChEBI
Cyproteronum	ChEBI
Novo-cyproterone	ChEBI
Ciproterona servycal	Kegg
6-Chlor-delta(6)-1,2-a-methylen-17-a-hydroxyprogesteron	Generator
6-Chlor-δ(6)-1,2-α-methylen-17-α-hydroxyprogesteron	Generator
6-Chlor-δ(6)-1,2-a-methylen-17-a-hydroxyprogesteron	HMDB
Cyproterone acetate	HMDB
Cyproterone, 1alpha,2 alpha,9 beta,10 alpha-isomer	HMDB

Chemical Formula

C₂₂H₂₇ClO₃

Average Molecular Weight

374.901

Monoisotopic Molecular Weight

374.164872437

IUPAC Name

(1S,2S,3S,5R,11R,12S,15R,16S)-15-acetyl-9-chloro-15-hydroxy-2,16-dimethylpentacyclo[9.7.0.0²,⁸.0³,⁵.0¹²,¹⁶]octadeca-7,9-dien-6-one

Traditional Name

cyproterone

CAS Registry Number

2098-66-0

SMILES

[H][C@@]12C[C@]1([H])[C@@]1(C)C(=CC2=O)C(Cl)=C[C@@]2([H])[C@]3([H])CC[C@](O)(C(C)=O)[C@@]3(C)CC[C@]12[H]

InChI Identifier

InChI=1S/C22H27ClO3/c1-11(24)22(26)7-5-14-12-9-18(23)17-10-19(25)13-8-16(13)21(17,3)15(12)4-6-20(14,22)2/h9-10,12-16,26H,4-8H2,1-3H3/t12-,13+,14-,15-,16-,20-,21-,22-/m0/s1

InChI Key

DUSHUSLJJMDGTE-ZJPMUUANSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Pregnane steroids

Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives

Alternative Parents

Substituents

Progestogin-skeleton
20-oxosteroid
3-oxosteroid
6-halo-steroid
Halo-steroid
Hydroxysteroid
Oxosteroid
17-hydroxysteroid
Cyclohexenone
Cyclic alcohol
Alpha-hydroxy ketone
Tertiary alcohol
Ketone
Vinyl halide
Vinyl chloride
Haloalkene
Chloroalkene
Organooxygen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organic oxide
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

17alpha-hydroxy steroid (CHEBI:50742 )
3-oxo Delta(4)-steroid (CHEBI:50742 )
20-oxo steroid (CHEBI:50742 )
chlorinated steroid (CHEBI:50742 )

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

Source

Exogenous

Exogenous (HMDB: HMDB0015587)

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	0.0066 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0066 g/L	ALOGPS
logP	3.37	ALOGPS
logP	3.2	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	12.7	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	102.66 m³·mol⁻¹	ChemAxon
Polarizability	40.67 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	223.085	30932474
DeepCCS	[M+Na]+	197.321	30932474
AllCCS	[M+H]+	188.1	32859911
AllCCS	[M+H-H2O]+	185.6	32859911
AllCCS	[M+NH4]+	190.4	32859911
AllCCS	[M+Na]+	191.1	32859911
AllCCS	[M-H]-	195.7	32859911
AllCCS	[M+Na-2H]-	196.0	32859911
AllCCS	[M+HCOO]-	196.5	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.	6.25 minutes	32390414
Predicted by Siyang on May 30, 2022	15.9662 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.87 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2779.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	358.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	206.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	185.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	262.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	684.9 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	696.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	82.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1278.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	491.4 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	1608.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	413.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	479.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	277.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	423.0 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	17.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cyproterone	[H][C@@]12C[C@]1([H])[C@@]1(C)C(=CC2=O)C(Cl)=C[C@@]2([H])[C@]3([H])CC[C@](O)(C(C)=O)[C@@]3(C)CC[C@]12[H]	4065.1	Standard polar	33892256
Cyproterone	[H][C@@]12C[C@]1([H])[C@@]1(C)C(=CC2=O)C(Cl)=C[C@@]2([H])[C@]3([H])CC[C@](O)(C(C)=O)[C@@]3(C)CC[C@]12[H]	2902.7	Standard non polar	33892256
Cyproterone	[H][C@@]12C[C@]1([H])[C@@]1(C)C(=CC2=O)C(Cl)=C[C@@]2([H])[C@]3([H])CC[C@](O)(C(C)=O)[C@@]3(C)CC[C@]12[H]	3328.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cyproterone,1TMS,isomer #1	CC(=O)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)[C@@H]5C[C@@H]5[C@]4(C)[C@H]3CC[C@@]21C	3182.1	Semi standard non polar	33892256
Cyproterone,1TMS,isomer #2	CC(=O)[C@@]1(O)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C)=C5C[C@@H]5[C@]4(C)[C@H]3CC[C@@]21C	3181.8	Semi standard non polar	33892256
Cyproterone,1TMS,isomer #3	C=C(O[Si](C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)[C@@H]5C[C@@H]5[C@]4(C)[C@H]3CC[C@@]21C	3076.2	Semi standard non polar	33892256
Cyproterone,2TMS,isomer #1	CC(=O)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C)=C5C[C@@H]5[C@]4(C)[C@H]3CC[C@@]21C	3147.0	Semi standard non polar	33892256
Cyproterone,2TMS,isomer #1	CC(=O)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C)=C5C[C@@H]5[C@]4(C)[C@H]3CC[C@@]21C	3118.7	Standard non polar	33892256
Cyproterone,2TMS,isomer #1	CC(=O)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C)=C5C[C@@H]5[C@]4(C)[C@H]3CC[C@@]21C	3406.2	Standard polar	33892256
Cyproterone,2TMS,isomer #2	C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)[C@@H]5C[C@@H]5[C@]4(C)[C@H]3CC[C@@]21C	3078.0	Semi standard non polar	33892256
Cyproterone,2TMS,isomer #2	C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)[C@@H]5C[C@@H]5[C@]4(C)[C@H]3CC[C@@]21C	3062.4	Standard non polar	33892256
Cyproterone,2TMS,isomer #2	C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)[C@@H]5C[C@@H]5[C@]4(C)[C@H]3CC[C@@]21C	3498.1	Standard polar	33892256
Cyproterone,2TMS,isomer #3	C=C(O[Si](C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C)=C5C[C@@H]5[C@]4(C)[C@H]3CC[C@@]21C	3021.8	Semi standard non polar	33892256
Cyproterone,2TMS,isomer #3	C=C(O[Si](C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C)=C5C[C@@H]5[C@]4(C)[C@H]3CC[C@@]21C	3065.7	Standard non polar	33892256
Cyproterone,2TMS,isomer #3	C=C(O[Si](C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C)=C5C[C@@H]5[C@]4(C)[C@H]3CC[C@@]21C	3545.0	Standard polar	33892256
Cyproterone,3TMS,isomer #1	C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C)=C5C[C@@H]5[C@]4(C)[C@H]3CC[C@@]21C	3027.1	Semi standard non polar	33892256
Cyproterone,3TMS,isomer #1	C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C)=C5C[C@@H]5[C@]4(C)[C@H]3CC[C@@]21C	3121.9	Standard non polar	33892256
Cyproterone,3TMS,isomer #1	C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C)=C5C[C@@H]5[C@]4(C)[C@H]3CC[C@@]21C	3470.0	Standard polar	33892256
Cyproterone,1TBDMS,isomer #1	CC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)[C@@H]5C[C@@H]5[C@]4(C)[C@H]3CC[C@@]21C	3448.9	Semi standard non polar	33892256
Cyproterone,1TBDMS,isomer #2	CC(=O)[C@@]1(O)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C(C)(C)C)=C5C[C@@H]5[C@]4(C)[C@H]3CC[C@@]21C	3420.6	Semi standard non polar	33892256
Cyproterone,1TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)[C@@H]5C[C@@H]5[C@]4(C)[C@H]3CC[C@@]21C	3328.4	Semi standard non polar	33892256
Cyproterone,2TBDMS,isomer #1	CC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C(C)(C)C)=C5C[C@@H]5[C@]4(C)[C@H]3CC[C@@]21C	3634.0	Semi standard non polar	33892256
Cyproterone,2TBDMS,isomer #1	CC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C(C)(C)C)=C5C[C@@H]5[C@]4(C)[C@H]3CC[C@@]21C	3593.2	Standard non polar	33892256
Cyproterone,2TBDMS,isomer #1	CC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C(C)(C)C)=C5C[C@@H]5[C@]4(C)[C@H]3CC[C@@]21C	3619.4	Standard polar	33892256
Cyproterone,2TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)[C@@H]5C[C@@H]5[C@]4(C)[C@H]3CC[C@@]21C	3591.0	Semi standard non polar	33892256
Cyproterone,2TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)[C@@H]5C[C@@H]5[C@]4(C)[C@H]3CC[C@@]21C	3544.8	Standard non polar	33892256
Cyproterone,2TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)[C@@H]5C[C@@H]5[C@]4(C)[C@H]3CC[C@@]21C	3690.4	Standard polar	33892256
Cyproterone,2TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C(C)(C)C)=C5C[C@@H]5[C@]4(C)[C@H]3CC[C@@]21C	3493.3	Semi standard non polar	33892256
Cyproterone,2TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C(C)(C)C)=C5C[C@@H]5[C@]4(C)[C@H]3CC[C@@]21C	3517.1	Standard non polar	33892256
Cyproterone,2TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C(C)(C)C)=C5C[C@@H]5[C@]4(C)[C@H]3CC[C@@]21C	3757.5	Standard polar	33892256
Cyproterone,3TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C(C)(C)C)=C5C[C@@H]5[C@]4(C)[C@H]3CC[C@@]21C	3732.1	Semi standard non polar	33892256
Cyproterone,3TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C(C)(C)C)=C5C[C@@H]5[C@]4(C)[C@H]3CC[C@@]21C	3730.5	Standard non polar	33892256
Cyproterone,3TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C(C)(C)C)=C5C[C@@H]5[C@]4(C)[C@H]3CC[C@@]21C	3716.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cyproterone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-8169000000-e02863f674ce9b2cd8af	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyproterone GC-MS (1 TMS) - 70eV, Positive	splash10-000x-8206900000-f9ad399212ec8f93d7a6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyproterone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyproterone 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyproterone 10V, Positive-QTOF	splash10-004i-0009000000-5c9997dd704debdab5ca	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyproterone 20V, Positive-QTOF	splash10-004i-0009000000-e47fd3a55c3a12221dd5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyproterone 40V, Positive-QTOF	splash10-01t9-0791000000-039d99fb2a68dd3679cd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyproterone 30V, Positive-QTOF	splash10-004i-0597000000-a25d388400f2d217a3fd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyproterone 20V, Negative-QTOF	splash10-00dj-0009000000-537af4c0d2592f4389fd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyproterone 10V, Negative-QTOF	splash10-00di-0009000000-bb0aa272579ae3c1410f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyproterone 50V, Positive-QTOF	splash10-01sl-0960000000-1c9079a8f9c425570114	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyproterone 50V, Positive-QTOF	splash10-01sl-0960000000-cfffb9275cd265ceda38	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyproterone 20V, Positive-QTOF	splash10-004i-0009000000-def96e1d98e700f1f8e5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyproterone 30V, Positive-QTOF	splash10-004i-0497000000-0fc287e4bba295d3133f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyproterone 40V, Positive-QTOF	splash10-01t9-0791000000-3adc56165c0ed068e6d4	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyproterone 10V, Positive-QTOF	splash10-004i-0009000000-db09659a5c3f6e2f3fe2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyproterone 20V, Positive-QTOF	splash10-0570-0149000000-c48ae0dca71891c801fe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyproterone 40V, Positive-QTOF	splash10-00ku-5190000000-499aae6f81444f0a43b8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyproterone 10V, Negative-QTOF	splash10-00di-0009000000-e97a51829845bb3ec8ba	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyproterone 20V, Negative-QTOF	splash10-00e9-0009000000-f19f24879c0b4fb2bfb4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyproterone 40V, Negative-QTOF	splash10-0aos-0159000000-749c9046181d23da6e9e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyproterone 10V, Positive-QTOF	splash10-056r-0009000000-473b61a34f936d1e6597	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyproterone 20V, Positive-QTOF	splash10-0550-0149000000-d743c7bd774552b0fafd	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyproterone 40V, Positive-QTOF	splash10-0080-5291000000-e21e7e39ebcfd99de937	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyproterone 10V, Negative-QTOF	splash10-00di-0009000000-3fb88b233fdbbb8c9838	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyproterone 20V, Negative-QTOF	splash10-00di-0009000000-5a882a4f198cfad8fba9	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyproterone 40V, Negative-QTOF	splash10-00ai-3009000000-e1e5a78c72aa7b9a9504	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
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 DB04839	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB04839	21059682	details

Abnormal Concentrations

Not Available

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

4447594

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cyproterone

METLIN ID

Not Available

PubChem Compound

5284537

PDB ID

Not Available

ChEBI ID

50742

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

Stadtler FA, Langner V: The effect of cyproterone and gonadotrophins on the adrenal gland of juvenile and adult rats. A morphological and morphometrical study. Pathol Res Pract. 1985 Mar;179(4-5):493-8. [PubMed:4001026 ]
Giorgi EP, Shirley IM, Grant JK, Stewart JC: Androgen dynamics in vitro in the human prostate gland. Effect of cyproterone and cyproterone acetate. Biochem J. 1973 Mar;132(3):465-74. [PubMed:4125095 ]
Holdaway IM, Croxson MS, Evans MC, France J, Sheehan A, Wilson T, Ibbertson HK: Effect of cyproterone acetate on glucocorticoid secretion in patients treated for hirsutism. Acta Endocrinol (Copenh). 1983 Oct;104(2):222-6. [PubMed:6227191 ]
Pham-Huu-Trung MT, de Smitter N, Bogyo A, Girard F: Effects of cyproterone acetate on adrenal steroidogenesis in vitro. Horm Res. 1984;20(2):108-15. [PubMed:6237971 ]
Honer C, Nam K, Fink C, Marshall P, Ksander G, Chatelain RE, Cornell W, Steele R, Schweitzer R, Schumacher C: Glucocorticoid receptor antagonism by cyproterone acetate and RU486. Mol Pharmacol. 2003 May;63(5):1012-20. [PubMed:12695529 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

Enzyme Details

1. Cytochrome P450 19A1

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:: CYP19A1
Uniprot ID:: P11511
Molecular weight:: 57882.48

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. Androgen receptor

General function:: Involved in DNA binding
Specific function:: Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3
Gene Name:: AR
Uniprot ID:: P10275
Molecular weight:: 98987.9

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 ]
Agoulnik IU, Weigel NL: Coactivator selective regulation of androgen receptor activity. Steroids. 2009 Aug;74(8):669-74. doi: 10.1016/j.steroids.2009.02.007. Epub 2009 Mar 9. [PubMed:19463689 ]
Cabeza M, Flores M, Bratoeff E, de la Pena A, Mendez E, Ceballos G: Intracellular Ca2+ stimulates the binding to androgen receptors in platelets. Steroids. 2004 Oct-Nov;69(11-12):767-72. [PubMed:15579329 ]
Sonneveld E, Jansen HJ, Riteco JA, Brouwer A, van der Burg B: Development of androgen- and estrogen-responsive bioassays, members of a panel of human cell line-based highly selective steroid-responsive bioassays. Toxicol Sci. 2005 Jan;83(1):136-48. Epub 2004 Oct 13. [PubMed:15483189 ]

Showing metabocard for Cyproterone (HMDB0015587)

MOL for HMDB0015587 (Cyproterone)

3D MOL for HMDB0015587 (Cyproterone)

3D SDF for HMDB0015587 (Cyproterone)

3D-SDF for HMDB0015587 (Cyproterone)

PDB for HMDB0015587 (Cyproterone)

3D PDB for HMDB0015587 (Cyproterone)

SMILES for HMDB0015587 (Cyproterone)

INCHI for HMDB0015587 (Cyproterone)

Structure for HMDB0015587 (Cyproterone)

3D Structure for HMDB0015587 (Cyproterone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References