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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 18:54:08 UTC

Update Date

2021-09-14 15:46:01 UTC

HMDB ID

HMDB0060708

Secondary Accession Numbers

HMDB60708

Metabolite Identification

Common Name

15beta-hydroxycyproterone acetate

Description

15beta-hydroxycyproterone acetate is a metabolite of cyproterone. Cyproterone is a steroidal antiandrogen which was never marketed. An acylated derivative, cyproterone acetate, is widely used clinically used as an antiandrogen and progestin. While cyproterone is sometimes used as a synonym for cyproterone acetate, what is almost always being referred to is actually cyproterone acetate and not cyproterone. (Wikipedia)

Structure

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


  Mrv0541 07041311542D          

 30 34  0  0  0  0            999 V2000
    6.2409    3.0340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4438    4.0608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7653    2.5143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4183    1.5225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1722    1.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9261    2.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9973    1.6728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.2686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4910   -0.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8124    1.1637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1542    2.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6983    3.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9106    0.8523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7526    0.5519    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0855    1.0372    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6645    1.1874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2449   -0.1183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9120   -0.6037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8238    0.0319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2600    0.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5065    0.8870    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5932    1.7074    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3316    0.7021    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4003    1.8784    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8253   -1.4241    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.8213    1.7282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5188    3.3617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0700   -0.3032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4310   -0.2561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1459    2.6632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
 11  1  1  0  0  0  0
 12  2  1  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  6  0  0  0
 15  5  1  1  0  0  0
 15 14  1  0  0  0  0
 16  7  1  0  0  0  0
 16 13  1  0  0  0  0
 17  9  2  0  0  0  0
 18  8  2  0  0  0  0
 18 17  1  0  0  0  0
 19  9  1  0  0  0  0
 19 13  1  0  0  0  0
 20 10  1  0  0  0  0
 21 14  1  0  0  0  0
 21 20  1  1  0  0  0
 22  3  1  1  0  0  0
 22  6  1  0  0  0  0
 22 21  1  0  0  0  0
 23  4  1  1  0  0  0
 23 15  1  0  0  0  0
 23 16  1  0  0  0  0
 23 17  1  0  0  0  0
 24 10  1  0  0  0  0
 24 11  1  1  0  0  0
 24 22  1  0  0  0  0
 25 18  1  0  0  0  0
 26 11  2  0  0  0  0
 27 12  2  0  0  0  0
 28 19  2  0  0  0  0
 29 20  1  0  0  0  0
 30 12  1  0  0  0  0
 24 30  1  6  0  0  0
M  END

HMDB0060708
     RDKit          3D
15beta-hydroxycyproterone acetate
 59 63  0  0  0  0  0  0  0  0999 V2000
   -3.7439   -3.2602    1.8804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8412   -2.1245    0.9286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9105   -1.9682    0.2853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8264   -1.2264    0.7057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8386   -0.1376   -0.1622 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8732    0.8727    0.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7688    0.7622    1.3250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0470    1.8604   -0.5612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9239   -0.5637   -1.6359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6078   -0.0830   -2.2689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7351    1.1147   -2.9109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7209   -0.1301   -1.1013 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6584    0.3941   -1.2082 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3187    0.0105   -2.4514 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6145   -0.1972   -2.4962 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4057   -0.6629   -4.0167 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4344   -0.0536   -1.2814 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7452   -0.1674   -1.3578 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5672   -0.0282   -0.1524 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6632    0.5318   -0.1566 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9791   -0.6140    1.0749 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3404    0.1640    2.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5049   -0.5302    1.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8269    0.2281    0.0343 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9656    1.7328    0.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3609   -0.1007    0.0504 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6558    0.4092    1.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8002    0.0963    1.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4755    0.5357   -0.0098 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5606    2.0140   -0.0571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7599   -3.5690    2.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2174   -4.1393    1.4362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2062   -2.9896    2.8120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3675    0.0319    2.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8122    0.4937    1.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8415    1.7574    1.8593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8940   -1.6720   -1.7129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7897   -0.1292   -2.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2513   -0.8402   -3.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9076    1.0345   -3.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6329   -1.2192   -0.8002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6360    1.5151   -1.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7702   -0.1221   -3.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2063   -0.3610   -2.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4525   -1.6171    1.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4564    1.2511    2.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3784   -0.3007    3.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9805   -1.4566    1.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7532    1.9893    1.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0374    2.0467    0.1315 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3846    2.3088   -0.4322 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2311   -1.2133    0.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7824    1.5013    1.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1141   -0.1432    2.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9653   -0.9921    1.4174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2736    0.6269    2.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8363    2.4595   -1.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5604    2.4430    0.2217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2348    2.4263    0.7511 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
  5  4  1  1
  5  6  1  0
  6  7  1  0
  6  8  2  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  1
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  6
 29  5  1  0
 29 12  1  0
 26 13  1  0
 24 17  1  0
 23 21  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  7 34  1  0
  7 35  1  0
  7 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 12 41  1  1
 13 42  1  1
 14 43  1  0
 18 44  1  0
 21 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 25 49  1  0
 25 50  1  0
 25 51  1  0
 26 52  1  1
 27 53  1  0
 27 54  1  0
 28 55  1  0
 28 56  1  0
 30 57  1  0
 30 58  1  0
 30 59  1  0
M  END


  Mrv0541 07041311542D          

 30 34  0  0  0  0            999 V2000
    6.2409    3.0340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4438    4.0608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7653    2.5143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4183    1.5225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1722    1.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9261    2.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9973    1.6728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.2686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4910   -0.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8124    1.1637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1542    2.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6983    3.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9106    0.8523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7526    0.5519    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0855    1.0372    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6645    1.1874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2449   -0.1183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9120   -0.6037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8238    0.0319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2600    0.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5065    0.8870    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5932    1.7074    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3316    0.7021    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4003    1.8784    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8253   -1.4241    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.8213    1.7282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5188    3.3617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0700   -0.3032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4310   -0.2561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1459    2.6632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
 11  1  1  0  0  0  0
 12  2  1  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  6  0  0  0
 15  5  1  1  0  0  0
 15 14  1  0  0  0  0
 16  7  1  0  0  0  0
 16 13  1  0  0  0  0
 17  9  2  0  0  0  0
 18  8  2  0  0  0  0
 18 17  1  0  0  0  0
 19  9  1  0  0  0  0
 19 13  1  0  0  0  0
 20 10  1  0  0  0  0
 21 14  1  0  0  0  0
 21 20  1  1  0  0  0
 22  3  1  1  0  0  0
 22  6  1  0  0  0  0
 22 21  1  0  0  0  0
 23  4  1  1  0  0  0
 23 15  1  0  0  0  0
 23 16  1  0  0  0  0
 23 17  1  0  0  0  0
 24 10  1  0  0  0  0
 24 11  1  1  0  0  0
 24 22  1  0  0  0  0
 25 18  1  0  0  0  0
 26 11  2  0  0  0  0
 27 12  2  0  0  0  0
 28 19  2  0  0  0  0
 29 20  1  0  0  0  0
 30 12  1  0  0  0  0
 24 30  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0060708

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)O[C@@]1(CC(O)[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)C5CC5[C@]4(C)[C@H]3CC[C@]12C)C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H29ClO5/c1-11(26)24(30-12(2)27)10-20(29)21-14-8-18(25)17-9-19(28)13-7-16(13)23(17,4)15(14)5-6-22(21,24)3/h8-9,13-16,20-21,29H,5-7,10H2,1-4H3/t13?,14-,15+,16?,20?,21-,22+,23+,24+/m1/s1

> <INCHI_KEY>
HRANPRDGABOKNQ-RXHWKJIASA-N

> <FORMULA>
C24H29ClO5

> <MOLECULAR_WEIGHT>
432.937

> <EXACT_MASS>
432.170351745

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
45.67070629204977

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,11R,12S,15R,16S)-15-acetyl-9-chloro-13-hydroxy-2,16-dimethyl-6-oxopentacyclo[9.7.0.0²,⁸.0³,⁵.0¹²,¹⁶]octadeca-7,9-dien-15-yl acetate

> <ALOGPS_LOGP>
3.02

> <JCHEM_LOGP>
2.2572981343333334

> <ALOGPS_LOGS>
-5.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.248787808742748

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.793402906877489

> <JCHEM_PKA_STRONGEST_BASIC>
-2.888429553624592

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
113.35839999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.17e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,11R,12S,15R,16S)-15-acetyl-9-chloro-13-hydroxy-2,16-dimethyl-6-oxopentacyclo[9.7.0.0²,⁸.0³,⁵.0¹²,¹⁶]octadeca-7,9-dien-15-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060708
     RDKit          3D
15beta-hydroxycyproterone acetate
 59 63  0  0  0  0  0  0  0  0999 V2000
   -3.7439   -3.2602    1.8804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8412   -2.1245    0.9286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9105   -1.9682    0.2853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8264   -1.2264    0.7057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8386   -0.1376   -0.1622 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8732    0.8727    0.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7688    0.7622    1.3250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0470    1.8604   -0.5612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9239   -0.5637   -1.6359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6078   -0.0830   -2.2689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7351    1.1147   -2.9109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7209   -0.1301   -1.1013 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6584    0.3941   -1.2082 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3187    0.0105   -2.4514 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6145   -0.1972   -2.4962 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4057   -0.6629   -4.0167 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4344   -0.0536   -1.2814 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7452   -0.1674   -1.3578 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5672   -0.0282   -0.1524 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6632    0.5318   -0.1566 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9791   -0.6140    1.0749 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3404    0.1640    2.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5049   -0.5302    1.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8269    0.2281    0.0343 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9656    1.7328    0.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3609   -0.1007    0.0504 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6558    0.4092    1.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8002    0.0963    1.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4755    0.5357   -0.0098 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5606    2.0140   -0.0571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7599   -3.5690    2.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2174   -4.1393    1.4362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2062   -2.9896    2.8120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3675    0.0319    2.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8122    0.4937    1.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8415    1.7574    1.8593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8940   -1.6720   -1.7129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7897   -0.1292   -2.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2513   -0.8402   -3.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9076    1.0345   -3.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6329   -1.2192   -0.8002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6360    1.5151   -1.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7702   -0.1221   -3.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2063   -0.3610   -2.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4525   -1.6171    1.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4564    1.2511    2.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3784   -0.3007    3.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9805   -1.4566    1.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7532    1.9893    1.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0374    2.0467    0.1315 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3846    2.3088   -0.4322 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2311   -1.2133    0.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7824    1.5013    1.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1141   -0.1432    2.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9653   -0.9921    1.4174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2736    0.6269    2.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8363    2.4595   -1.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5604    2.4430    0.2217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2348    2.4263    0.7511 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
  5  4  1  1
  5  6  1  0
  6  7  1  0
  6  8  2  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  1
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  6
 29  5  1  0
 29 12  1  0
 26 13  1  0
 24 17  1  0
 23 21  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  7 34  1  0
  7 35  1  0
  7 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 12 41  1  1
 13 42  1  1
 14 43  1  0
 18 44  1  0
 21 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 25 49  1  0
 25 50  1  0
 25 51  1  0
 26 52  1  1
 27 53  1  0
 27 54  1  0
 28 55  1  0
 28 56  1  0
 30 57  1  0
 30 58  1  0
 30 59  1  0
M  END

HEADER    PROTEIN                                 04-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUL-13         0                                  
HETATM    1  C   UNK     0      11.650   5.663   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.162   7.580   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.895   4.693   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.514   2.842   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.921   3.468   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.329   4.093   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.862   3.123   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.843  -0.501   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.783  -0.846   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.850   2.172   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.488   4.132   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.637   6.115   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.700   1.591   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.005   1.030   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.760   1.936   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.107   2.216   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.190  -0.221   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.436  -1.127   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.538   0.060   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.819   1.029   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.412   1.656   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.574   3.187   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.352   1.311   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.081   3.506   0.000  0.00  0.00           C+0
HETATM   25 Cl   UNK     0       5.274  -2.658   0.000  0.00  0.00          Cl+0
HETATM   26  O   UNK     0      12.733   3.226   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      12.168   6.275   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       0.131  -0.566   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      10.138  -0.478   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       9.606   4.971   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   12                                                            
CONECT    3   22                                                            
CONECT    4   23                                                            
CONECT    5    6   15                                                       
CONECT    6    5   22                                                       
CONECT    7   13   16                                                       
CONECT    8   14   18                                                       
CONECT    9   17   19                                                       
CONECT   10   20   24                                                       
CONECT   11    1   24   26                                                  
CONECT   12    2   27   30                                                  
CONECT   13    7   16   19                                                  
CONECT   14    8   15   21                                                  
CONECT   15    5   14   23                                                  
CONECT   16    7   13   23                                                  
CONECT   17    9   18   23                                                  
CONECT   18    8   17   25                                                  
CONECT   19    9   13   28                                                  
CONECT   20   10   21   29                                                  
CONECT   21   14   20   22                                                  
CONECT   22    3    6   21   24                                             
CONECT   23    4   15   16   17                                             
CONECT   24   10   11   22   30                                             
CONECT   25   18                                                            
CONECT   26   11                                                            
CONECT   27   12                                                            
CONECT   28   19                                                            
CONECT   29   20                                                            
CONECT   30   12   24                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

COMPND    HMDB0060708
HETATM    1  C1  UNL     1      -3.744  -3.260   1.880  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.841  -2.124   0.929  1.00  0.00           C  
HETATM    3  O1  UNL     1      -4.911  -1.968   0.285  1.00  0.00           O  
HETATM    4  O2  UNL     1      -2.826  -1.226   0.706  1.00  0.00           O  
HETATM    5  C3  UNL     1      -2.839  -0.138  -0.162  1.00  0.00           C  
HETATM    6  C4  UNL     1      -3.873   0.873   0.145  1.00  0.00           C  
HETATM    7  C5  UNL     1      -4.769   0.762   1.325  1.00  0.00           C  
HETATM    8  O3  UNL     1      -4.047   1.860  -0.561  1.00  0.00           O  
HETATM    9  C6  UNL     1      -2.924  -0.564  -1.636  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.608  -0.083  -2.269  1.00  0.00           C  
HETATM   11  O4  UNL     1      -1.735   1.115  -2.911  1.00  0.00           O  
HETATM   12  C8  UNL     1      -0.721  -0.130  -1.101  1.00  0.00           C  
HETATM   13  C9  UNL     1       0.658   0.394  -1.208  1.00  0.00           C  
HETATM   14  C10 UNL     1       1.319   0.011  -2.451  1.00  0.00           C  
HETATM   15  C11 UNL     1       2.615  -0.197  -2.496  1.00  0.00           C  
HETATM   16 CL1  UNL     1       3.406  -0.663  -4.017  1.00  0.00          CL  
HETATM   17  C12 UNL     1       3.434  -0.054  -1.281  1.00  0.00           C  
HETATM   18  C13 UNL     1       4.745  -0.167  -1.358  1.00  0.00           C  
HETATM   19  C14 UNL     1       5.567  -0.028  -0.152  1.00  0.00           C  
HETATM   20  O5  UNL     1       6.663   0.532  -0.157  1.00  0.00           O  
HETATM   21  C15 UNL     1       4.979  -0.614   1.075  1.00  0.00           C  
HETATM   22  C16 UNL     1       4.340   0.164   2.133  1.00  0.00           C  
HETATM   23  C17 UNL     1       3.505  -0.530   1.117  1.00  0.00           C  
HETATM   24  C18 UNL     1       2.827   0.228   0.034  1.00  0.00           C  
HETATM   25  C19 UNL     1       2.966   1.733   0.298  1.00  0.00           C  
HETATM   26  C20 UNL     1       1.361  -0.101   0.050  1.00  0.00           C  
HETATM   27  C21 UNL     1       0.656   0.409   1.267  1.00  0.00           C  
HETATM   28  C22 UNL     1      -0.800   0.096   1.294  1.00  0.00           C  
HETATM   29  C23 UNL     1      -1.475   0.536  -0.010  1.00  0.00           C  
HETATM   30  C24 UNL     1      -1.561   2.014  -0.057  1.00  0.00           C  
HETATM   31  H1  UNL     1      -4.760  -3.569   2.181  1.00  0.00           H  
HETATM   32  H2  UNL     1      -3.217  -4.139   1.436  1.00  0.00           H  
HETATM   33  H3  UNL     1      -3.206  -2.990   2.812  1.00  0.00           H  
HETATM   34  H4  UNL     1      -4.367   0.032   2.071  1.00  0.00           H  
HETATM   35  H5  UNL     1      -5.812   0.494   1.065  1.00  0.00           H  
HETATM   36  H6  UNL     1      -4.842   1.757   1.859  1.00  0.00           H  
HETATM   37  H7  UNL     1      -2.894  -1.672  -1.713  1.00  0.00           H  
HETATM   38  H8  UNL     1      -3.790  -0.129  -2.137  1.00  0.00           H  
HETATM   39  H9  UNL     1      -1.251  -0.840  -3.026  1.00  0.00           H  
HETATM   40  H10 UNL     1      -1.908   1.034  -3.888  1.00  0.00           H  
HETATM   41  H11 UNL     1      -0.633  -1.219  -0.800  1.00  0.00           H  
HETATM   42  H12 UNL     1       0.636   1.515  -1.101  1.00  0.00           H  
HETATM   43  H13 UNL     1       0.770  -0.122  -3.395  1.00  0.00           H  
HETATM   44  H14 UNL     1       5.206  -0.361  -2.333  1.00  0.00           H  
HETATM   45  H15 UNL     1       5.452  -1.617   1.301  1.00  0.00           H  
HETATM   46  H16 UNL     1       4.456   1.251   2.178  1.00  0.00           H  
HETATM   47  H17 UNL     1       4.378  -0.301   3.161  1.00  0.00           H  
HETATM   48  H18 UNL     1       2.981  -1.457   1.464  1.00  0.00           H  
HETATM   49  H19 UNL     1       2.753   1.989   1.342  1.00  0.00           H  
HETATM   50  H20 UNL     1       4.037   2.047   0.131  1.00  0.00           H  
HETATM   51  H21 UNL     1       2.385   2.309  -0.432  1.00  0.00           H  
HETATM   52  H22 UNL     1       1.231  -1.213   0.041  1.00  0.00           H  
HETATM   53  H23 UNL     1       0.782   1.501   1.419  1.00  0.00           H  
HETATM   54  H24 UNL     1       1.114  -0.143   2.143  1.00  0.00           H  
HETATM   55  H25 UNL     1      -0.965  -0.992   1.417  1.00  0.00           H  
HETATM   56  H26 UNL     1      -1.274   0.627   2.124  1.00  0.00           H  
HETATM   57  H27 UNL     1      -1.836   2.459  -1.005  1.00  0.00           H  
HETATM   58  H28 UNL     1      -0.560   2.443   0.222  1.00  0.00           H  
HETATM   59  H29 UNL     1      -2.235   2.426   0.751  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6    9   29
CONECT    6    7    8    8
CONECT    7   34   35   36
CONECT    9   10   37   38
CONECT   10   11   12   39
CONECT   11   40
CONECT   12   13   29   41
CONECT   13   14   26   42
CONECT   14   15   15   43
CONECT   15   16   17
CONECT   17   18   18   24
CONECT   18   19   44
CONECT   19   20   20   21
CONECT   21   22   23   45
CONECT   22   23   46   47
CONECT   23   24   48
CONECT   24   25   26
CONECT   25   49   50   51
CONECT   26   27   52
CONECT   27   28   53   54
CONECT   28   29   55   56
CONECT   29   30
CONECT   30   57   58   59
END

HMDB0060708
     RDKit          3D
15beta-hydroxycyproterone acetate
 59 63  0  0  0  0  0  0  0  0999 V2000
   -3.7439   -3.2602    1.8804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8412   -2.1245    0.9286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9105   -1.9682    0.2853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8264   -1.2264    0.7057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8386   -0.1376   -0.1622 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8732    0.8727    0.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7688    0.7622    1.3250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0470    1.8604   -0.5612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9239   -0.5637   -1.6359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6078   -0.0830   -2.2689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7351    1.1147   -2.9109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7209   -0.1301   -1.1013 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6584    0.3941   -1.2082 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3187    0.0105   -2.4514 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6145   -0.1972   -2.4962 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4057   -0.6629   -4.0167 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4344   -0.0536   -1.2814 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7452   -0.1674   -1.3578 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5672   -0.0282   -0.1524 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6632    0.5318   -0.1566 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9791   -0.6140    1.0749 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3404    0.1640    2.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5049   -0.5302    1.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8269    0.2281    0.0343 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9656    1.7328    0.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3609   -0.1007    0.0504 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6558    0.4092    1.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8002    0.0963    1.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4755    0.5357   -0.0098 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5606    2.0140   -0.0571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7599   -3.5690    2.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2174   -4.1393    1.4362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2062   -2.9896    2.8120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3675    0.0319    2.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8122    0.4937    1.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8415    1.7574    1.8593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8940   -1.6720   -1.7129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7897   -0.1292   -2.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2513   -0.8402   -3.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9076    1.0345   -3.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6329   -1.2192   -0.8002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6360    1.5151   -1.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7702   -0.1221   -3.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2063   -0.3610   -2.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4525   -1.6171    1.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4564    1.2511    2.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3784   -0.3007    3.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9805   -1.4566    1.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7532    1.9893    1.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0374    2.0467    0.1315 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3846    2.3088   -0.4322 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2311   -1.2133    0.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7824    1.5013    1.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1141   -0.1432    2.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9653   -0.9921    1.4174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2736    0.6269    2.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8363    2.4595   -1.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5604    2.4430    0.2217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2348    2.4263    0.7511 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
  5  4  1  1
  5  6  1  0
  6  7  1  0
  6  8  2  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  1
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  6
 29  5  1  0
 29 12  1  0
 26 13  1  0
 24 17  1  0
 23 21  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  7 34  1  0
  7 35  1  0
  7 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 12 41  1  1
 13 42  1  1
 14 43  1  0
 18 44  1  0
 21 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 25 49  1  0
 25 50  1  0
 25 51  1  0
 26 52  1  1
 27 53  1  0
 27 54  1  0
 28 55  1  0
 28 56  1  0
 30 57  1  0
 30 58  1  0
 30 59  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
15b-Hydroxycyproterone acetate	Generator
15b-Hydroxycyproterone acetic acid	Generator
15beta-Hydroxycyproterone acetic acid	Generator
15Β-hydroxycyproterone acetate	Generator
15Β-hydroxycyproterone acetic acid	Generator
15 beta-Hydroxycyproterone acetate	HMDB
15-OHCPA	HMDB
15-Hydroxycyproterone acetate	HMDB

Chemical Formula

C₂₄H₂₉ClO₅

Average Molecular Weight

432.937

Monoisotopic Molecular Weight

432.170351745

IUPAC Name

(1S,2S,11R,12S,15R,16S)-15-acetyl-9-chloro-13-hydroxy-2,16-dimethyl-6-oxopentacyclo[9.7.0.0²,⁸.0³,⁵.0¹²,¹⁶]octadeca-7,9-dien-15-yl acetate

Traditional Name

(1S,2S,11R,12S,15R,16S)-15-acetyl-9-chloro-13-hydroxy-2,16-dimethyl-6-oxopentacyclo[9.7.0.0²,⁸.0³,⁵.0¹²,¹⁶]octadeca-7,9-dien-15-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@]1(CC(O)[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)C5CC5[C@]4(C)[C@H]3CC[C@]12C)C(C)=O

InChI Identifier

InChI=1S/C24H29ClO5/c1-11(26)24(30-12(2)27)10-20(29)21-14-8-18(25)17-9-19(28)13-7-16(13)23(17,4)15(14)5-6-22(21,24)3/h8-9,13-16,20-21,29H,5-7,10H2,1-4H3/t13?,14-,15+,16?,20?,21-,22+,23+,24+/m1/s1

InChI Key

HRANPRDGABOKNQ-RXHWKJIASA-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
Steroid ester
20-oxosteroid
3-oxosteroid
6-halo-steroid
Halo-steroid
15-hydroxysteroid
Oxosteroid
Hydroxysteroid
Cyclohexenone
Alpha-acyloxy ketone
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Ketone
Carboxylic acid derivative
Chloroalkene
Haloalkene
Vinyl halide
Vinyl chloride
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organooxygen compound
Organochloride
Organic oxide
Organohalogen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060708)
Liver (HMDB: HMDB0060708)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060708)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060708)

Cellular substructure

Cytoplasm (HMDB: HMDB0060708)
Membrane (HMDB: HMDB0060708)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0042 g/L	ALOGPS
logP	3.02	ALOGPS
logP	2.26	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	14.79	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	113.36 m³·mol⁻¹	ChemAxon
Polarizability	45.67 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]-	226.095	30932474
DeepCCS	[M+Na]+	200.957	30932474
AllCCS	[M+H]+	199.9	32859911
AllCCS	[M+H-H2O]+	197.7	32859911
AllCCS	[M+NH4]+	201.8	32859911
AllCCS	[M+Na]+	202.4	32859911
AllCCS	[M-H]-	205.0	32859911
AllCCS	[M+Na-2H]-	205.8	32859911
AllCCS	[M+HCOO]-	206.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
15beta-hydroxycyproterone acetate	CC(=O)O[C@@]1(CC(O)[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)C5CC5[C@]4(C)[C@H]3CC[C@]12C)C(C)=O	4285.5	Standard polar	33892256
15beta-hydroxycyproterone acetate	CC(=O)O[C@@]1(CC(O)[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)C5CC5[C@]4(C)[C@H]3CC[C@]12C)C(C)=O	3007.1	Standard non polar	33892256
15beta-hydroxycyproterone acetate	CC(=O)O[C@@]1(CC(O)[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)C5CC5[C@]4(C)[C@H]3CC[C@]12C)C(C)=O	3481.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
15beta-hydroxycyproterone acetate,1TMS,isomer #1	CC(=O)O[C@]1(C(C)=O)CC(O[Si](C)(C)C)[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)C5CC5[C@]4(C)[C@H]3CC[C@@]21C	3306.0	Semi standard non polar	33892256
15beta-hydroxycyproterone acetate,1TMS,isomer #2	CC(=O)O[C@]1(C(C)=O)CC(O)[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C)=C5CC5[C@]4(C)[C@H]3CC[C@@]21C	3300.3	Semi standard non polar	33892256
15beta-hydroxycyproterone acetate,1TMS,isomer #3	C=C(O[Si](C)(C)C)[C@@]1(OC(C)=O)CC(O)[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)C5CC5[C@]4(C)[C@H]3CC[C@@]21C	3265.1	Semi standard non polar	33892256
15beta-hydroxycyproterone acetate,2TMS,isomer #1	CC(=O)O[C@]1(C(C)=O)CC(O[Si](C)(C)C)[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C)=C5CC5[C@]4(C)[C@H]3CC[C@@]21C	3265.8	Semi standard non polar	33892256
15beta-hydroxycyproterone acetate,2TMS,isomer #1	CC(=O)O[C@]1(C(C)=O)CC(O[Si](C)(C)C)[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C)=C5CC5[C@]4(C)[C@H]3CC[C@@]21C	3274.6	Standard non polar	33892256
15beta-hydroxycyproterone acetate,2TMS,isomer #1	CC(=O)O[C@]1(C(C)=O)CC(O[Si](C)(C)C)[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C)=C5CC5[C@]4(C)[C@H]3CC[C@@]21C	3768.9	Standard polar	33892256
15beta-hydroxycyproterone acetate,2TMS,isomer #2	C=C(O[Si](C)(C)C)[C@@]1(OC(C)=O)CC(O[Si](C)(C)C)[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)C5CC5[C@]4(C)[C@H]3CC[C@@]21C	3234.1	Semi standard non polar	33892256
15beta-hydroxycyproterone acetate,2TMS,isomer #2	C=C(O[Si](C)(C)C)[C@@]1(OC(C)=O)CC(O[Si](C)(C)C)[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)C5CC5[C@]4(C)[C@H]3CC[C@@]21C	3206.2	Standard non polar	33892256
15beta-hydroxycyproterone acetate,2TMS,isomer #2	C=C(O[Si](C)(C)C)[C@@]1(OC(C)=O)CC(O[Si](C)(C)C)[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)C5CC5[C@]4(C)[C@H]3CC[C@@]21C	3871.0	Standard polar	33892256
15beta-hydroxycyproterone acetate,2TMS,isomer #3	C=C(O[Si](C)(C)C)[C@@]1(OC(C)=O)CC(O)[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C)=C5CC5[C@]4(C)[C@H]3CC[C@@]21C	3222.7	Semi standard non polar	33892256
15beta-hydroxycyproterone acetate,2TMS,isomer #3	C=C(O[Si](C)(C)C)[C@@]1(OC(C)=O)CC(O)[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C)=C5CC5[C@]4(C)[C@H]3CC[C@@]21C	3296.0	Standard non polar	33892256
15beta-hydroxycyproterone acetate,2TMS,isomer #3	C=C(O[Si](C)(C)C)[C@@]1(OC(C)=O)CC(O)[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C)=C5CC5[C@]4(C)[C@H]3CC[C@@]21C	3908.3	Standard polar	33892256
15beta-hydroxycyproterone acetate,3TMS,isomer #1	C=C(O[Si](C)(C)C)[C@@]1(OC(C)=O)CC(O[Si](C)(C)C)[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C)=C5CC5[C@]4(C)[C@H]3CC[C@@]21C	3176.7	Semi standard non polar	33892256
15beta-hydroxycyproterone acetate,3TMS,isomer #1	C=C(O[Si](C)(C)C)[C@@]1(OC(C)=O)CC(O[Si](C)(C)C)[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C)=C5CC5[C@]4(C)[C@H]3CC[C@@]21C	3281.6	Standard non polar	33892256
15beta-hydroxycyproterone acetate,3TMS,isomer #1	C=C(O[Si](C)(C)C)[C@@]1(OC(C)=O)CC(O[Si](C)(C)C)[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C)=C5CC5[C@]4(C)[C@H]3CC[C@@]21C	3821.6	Standard polar	33892256
15beta-hydroxycyproterone acetate,1TBDMS,isomer #1	CC(=O)O[C@]1(C(C)=O)CC(O[Si](C)(C)C(C)(C)C)[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)C5CC5[C@]4(C)[C@H]3CC[C@@]21C	3563.0	Semi standard non polar	33892256
15beta-hydroxycyproterone acetate,1TBDMS,isomer #2	CC(=O)O[C@]1(C(C)=O)CC(O)[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C(C)(C)C)=C5CC5[C@]4(C)[C@H]3CC[C@@]21C	3543.4	Semi standard non polar	33892256
15beta-hydroxycyproterone acetate,1TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(OC(C)=O)CC(O)[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)C5CC5[C@]4(C)[C@H]3CC[C@@]21C	3514.0	Semi standard non polar	33892256
15beta-hydroxycyproterone acetate,2TBDMS,isomer #1	CC(=O)O[C@]1(C(C)=O)CC(O[Si](C)(C)C(C)(C)C)[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C(C)(C)C)=C5CC5[C@]4(C)[C@H]3CC[C@@]21C	3752.3	Semi standard non polar	33892256
15beta-hydroxycyproterone acetate,2TBDMS,isomer #1	CC(=O)O[C@]1(C(C)=O)CC(O[Si](C)(C)C(C)(C)C)[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C(C)(C)C)=C5CC5[C@]4(C)[C@H]3CC[C@@]21C	3726.4	Standard non polar	33892256
15beta-hydroxycyproterone acetate,2TBDMS,isomer #1	CC(=O)O[C@]1(C(C)=O)CC(O[Si](C)(C)C(C)(C)C)[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C(C)(C)C)=C5CC5[C@]4(C)[C@H]3CC[C@@]21C	3974.1	Standard polar	33892256
15beta-hydroxycyproterone acetate,2TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(OC(C)=O)CC(O[Si](C)(C)C(C)(C)C)[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)C5CC5[C@]4(C)[C@H]3CC[C@@]21C	3755.9	Semi standard non polar	33892256
15beta-hydroxycyproterone acetate,2TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(OC(C)=O)CC(O[Si](C)(C)C(C)(C)C)[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)C5CC5[C@]4(C)[C@H]3CC[C@@]21C	3638.2	Standard non polar	33892256
15beta-hydroxycyproterone acetate,2TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(OC(C)=O)CC(O[Si](C)(C)C(C)(C)C)[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)C5CC5[C@]4(C)[C@H]3CC[C@@]21C	4047.9	Standard polar	33892256
15beta-hydroxycyproterone acetate,2TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(OC(C)=O)CC(O)[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C(C)(C)C)=C5CC5[C@]4(C)[C@H]3CC[C@@]21C	3703.1	Semi standard non polar	33892256
15beta-hydroxycyproterone acetate,2TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(OC(C)=O)CC(O)[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C(C)(C)C)=C5CC5[C@]4(C)[C@H]3CC[C@@]21C	3727.4	Standard non polar	33892256
15beta-hydroxycyproterone acetate,2TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(OC(C)=O)CC(O)[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C(C)(C)C)=C5CC5[C@]4(C)[C@H]3CC[C@@]21C	4094.5	Standard polar	33892256
15beta-hydroxycyproterone acetate,3TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(OC(C)=O)CC(O[Si](C)(C)C(C)(C)C)[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C(C)(C)C)=C5CC5[C@]4(C)[C@H]3CC[C@@]21C	3866.3	Semi standard non polar	33892256
15beta-hydroxycyproterone acetate,3TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(OC(C)=O)CC(O[Si](C)(C)C(C)(C)C)[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C(C)(C)C)=C5CC5[C@]4(C)[C@H]3CC[C@@]21C	3855.6	Standard non polar	33892256
15beta-hydroxycyproterone acetate,3TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(OC(C)=O)CC(O[Si](C)(C)C(C)(C)C)[C@H]2[C@@H]3C=C(Cl)C4=CC(O[Si](C)(C)C(C)(C)C)=C5CC5[C@]4(C)[C@H]3CC[C@@]21C	4045.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 15beta-hydroxycyproterone acetate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-1039000000-d7c7f25fd9c59f9e962d	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 15beta-hydroxycyproterone acetate GC-MS (1 TMS) - 70eV, Positive	splash10-03kl-4019400000-5123798857097c516297	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 15beta-hydroxycyproterone acetate 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 - 15beta-hydroxycyproterone acetate 10V, Positive-QTOF	splash10-0159-0006900000-43df84ad576903ff5437	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15beta-hydroxycyproterone acetate 20V, Positive-QTOF	splash10-0603-0049400000-9423121feac4916fb86b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15beta-hydroxycyproterone acetate 40V, Positive-QTOF	splash10-00ec-2095000000-0da727b0a07d93677fb1	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15beta-hydroxycyproterone acetate 10V, Negative-QTOF	splash10-001i-2004900000-dd9bd1f8db1b8e9fd381	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15beta-hydroxycyproterone acetate 20V, Negative-QTOF	splash10-05a9-3009300000-cd9989e4f5cf854b909d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15beta-hydroxycyproterone acetate 40V, Negative-QTOF	splash10-0ab9-9027000000-6148c3b024c1123d3af9	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15beta-hydroxycyproterone acetate 10V, Positive-QTOF	splash10-001i-0004900000-c2f97d6ed26b4951f64a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15beta-hydroxycyproterone acetate 20V, Positive-QTOF	splash10-05yl-0039200000-0f873989d1098e665ba8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15beta-hydroxycyproterone acetate 40V, Positive-QTOF	splash10-003r-2492300000-f46dd4b1e9fce154110c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15beta-hydroxycyproterone acetate 10V, Negative-QTOF	splash10-0089-1009800000-92c12d4eebdc32777739	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15beta-hydroxycyproterone acetate 20V, Negative-QTOF	splash10-05fr-5009000000-29bfdb843483318f1579	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15beta-hydroxycyproterone acetate 40V, Negative-QTOF	splash10-052f-9000000000-8d78c4eda9cf80c8b539	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

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	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

196706

PDB ID

Not Available

ChEBI ID

Not Available

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

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.

Showing metabocard for 15beta-hydroxycyproterone acetate (HMDB0060708)

MOL for HMDB0060708 (15beta-hydroxycyproterone acetate)

3D MOL for HMDB0060708 (15beta-hydroxycyproterone acetate)

3D SDF for HMDB0060708 (15beta-hydroxycyproterone acetate)

3D-SDF for HMDB0060708 (15beta-hydroxycyproterone acetate)

PDB for HMDB0060708 (15beta-hydroxycyproterone acetate)

3D PDB for HMDB0060708 (15beta-hydroxycyproterone acetate)

SMILES for HMDB0060708 (15beta-hydroxycyproterone acetate)

INCHI for HMDB0060708 (15beta-hydroxycyproterone acetate)

Structure for HMDB0060708 (15beta-hydroxycyproterone acetate)

3D Structure for HMDB0060708 (15beta-hydroxycyproterone acetate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra