NP-MRD: Showing NP-Card for Epietiocholanolone (NP0000135)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2020-11-24 22:13:07 UTC

NP-MRD ID

NP0000135

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Epietiocholanolone

Description

Epietiocholanolone is an anabolic steroid similar in structure to androstenedione. Used by body-builders to add muscle mass, but with unknown side effects.

Structure

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

5b-Epiandrosterone.mol
  Mrv1652305271900102D          

 25 28  0  0  0  0            999 V2000
   -2.0637   -1.1385    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0637   -0.3135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3492    0.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3492   -1.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348   -1.1385    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0797   -1.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942   -1.1385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942   -0.3135    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5086    0.0990    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2933   -0.1560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7782    0.5115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2933    1.1789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5086    0.9240    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5086    1.7490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942    1.3365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797    0.9240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797    0.0990    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6348   -0.3135    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6348    0.5115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5482    1.9635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7782   -1.5510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348   -1.9635    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797   -0.7260    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942    0.5115    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5086   -0.7260    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  0  0  0  0
  3 18  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  1  0  0  0
 12 20  2  0  0  0  0
  1 21  1  1  0  0  0
  5 22  1  1  0  0  0
 17 23  1  6  0  0  0
  8 24  1  1  0  0  0
  9 25  1  6  0  0  0
M  END

HMDB0000546
     RDKit          3D
Epietiocholanolone
 51 54  0  0  0  0  0  0  0  0999 V2000
    2.7805   -0.4679    1.5124 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8179    0.5893    0.4532 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1058    1.8485    0.8219 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6323    1.7166    0.8851 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0072    0.8912   -0.1805 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8198   -0.3710   -0.4961 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1362   -1.1943   -1.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1738   -1.6952   -0.9550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5468   -1.0085    0.3227 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9827   -1.3228    0.6489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9564   -0.8362   -0.3692 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2434   -0.9305    0.2094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7334    0.6066   -0.7567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2994    0.9505   -0.9469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3938    0.4914    0.1569 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8768    1.1244    1.4453 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1867    0.0971   -0.8591 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1407   -0.9611   -1.2718 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5084   -0.4362   -0.8168 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2034    0.7807    0.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0041    1.6545    0.2036 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7754   -1.5051    1.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7375   -0.3977    2.1031 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9742   -0.3100    2.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4665    2.1376    1.8514 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4590    2.6665    0.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2990    1.3765    1.9074 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1955    2.7549    0.7988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0527    1.4925   -1.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8980   -0.9462    0.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0003   -0.6174   -2.4648 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7974   -2.0464   -1.7859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0709   -2.7679   -0.7505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9558   -1.4704   -1.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9492   -1.3692    1.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0579   -2.4471    0.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1959   -0.9838    1.6838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9530   -1.5270   -1.2232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1273   -0.6108    1.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2863    1.2919   -0.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2399    0.7328   -1.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2288    2.0776   -0.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9886    0.6250   -1.9518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9814    1.0340    1.4683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6358    2.1942    1.5080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5139    0.5432    2.3317 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2000    0.9660   -1.5373 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9205   -1.9505   -0.8786 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1655   -1.0276   -2.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1690   -0.2181   -1.6542 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9383   -1.2245   -0.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 17  2  1  0
 20  2  1  0
 15  5  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  6
  6 30  1  1
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  1
 10 36  1  0
 10 37  1  0
 11 38  1  6
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 16 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  6
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
M  END

5b-Epiandrosterone.mol
  Mrv1652305271900102D          

 25 28  0  0  0  0            999 V2000
   -2.0637   -1.1385    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0637   -0.3135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3492    0.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3492   -1.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348   -1.1385    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0797   -1.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942   -1.1385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942   -0.3135    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5086    0.0990    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2933   -0.1560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7782    0.5115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2933    1.1789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5086    0.9240    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5086    1.7490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942    1.3365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797    0.9240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797    0.0990    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6348   -0.3135    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6348    0.5115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5482    1.9635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7782   -1.5510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348   -1.9635    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797   -0.7260    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942    0.5115    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5086   -0.7260    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  0  0  0  0
  3 18  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  1  0  0  0
 12 20  2  0  0  0  0
  1 21  1  1  0  0  0
  5 22  1  1  0  0  0
 17 23  1  6  0  0  0
  8 24  1  1  0  0  0
  9 25  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0000135

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12-,13+,14+,15+,16+,18+,19+/m1/s1

> <INCHI_KEY>
QGXBDMJGAMFCBF-XRJZGPCZSA-N

> <FORMULA>
C19H30O2

> <MOLECULAR_WEIGHT>
290.4403

> <EXACT_MASS>
290.224580204

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
34.654086773768185

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,5S,7R,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one

> <ALOGPS_LOGP>
3.71

> <JCHEM_LOGP>
3.7672845366666667

> <ALOGPS_LOGS>
-4.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.96171995034024

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.296396321120497

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3569559187002107

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
83.80889999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.37e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5S,7R,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0000546
     RDKit          3D
Epietiocholanolone
 51 54  0  0  0  0  0  0  0  0999 V2000
    2.7805   -0.4679    1.5124 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8179    0.5893    0.4532 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1058    1.8485    0.8219 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6323    1.7166    0.8851 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0072    0.8912   -0.1805 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8198   -0.3710   -0.4961 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1362   -1.1943   -1.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1738   -1.6952   -0.9550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5468   -1.0085    0.3227 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9827   -1.3228    0.6489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9564   -0.8362   -0.3692 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2434   -0.9305    0.2094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7334    0.6066   -0.7567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2994    0.9505   -0.9469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3938    0.4914    0.1569 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8768    1.1244    1.4453 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1867    0.0971   -0.8591 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1407   -0.9611   -1.2718 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5084   -0.4362   -0.8168 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2034    0.7807    0.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0041    1.6545    0.2036 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7754   -1.5051    1.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7375   -0.3977    2.1031 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9742   -0.3100    2.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4665    2.1376    1.8514 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4590    2.6665    0.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2990    1.3765    1.9074 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1955    2.7549    0.7988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0527    1.4925   -1.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8980   -0.9462    0.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0003   -0.6174   -2.4648 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7974   -2.0464   -1.7859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0709   -2.7679   -0.7505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9558   -1.4704   -1.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9492   -1.3692    1.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0579   -2.4471    0.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1959   -0.9838    1.6838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9530   -1.5270   -1.2232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1273   -0.6108    1.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2863    1.2919   -0.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2399    0.7328   -1.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2288    2.0776   -0.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9886    0.6250   -1.9518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9814    1.0340    1.4683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6358    2.1942    1.5080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5139    0.5432    2.3317 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2000    0.9660   -1.5373 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9205   -1.9505   -0.8786 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1655   -1.0276   -2.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1690   -0.2181   -1.6542 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9383   -1.2245   -0.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 17  2  1  0
 20  2  1  0
 15  5  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  6
  6 30  1  1
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  1
 10 36  1  0
 10 37  1  0
 11 38  1  6
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 16 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  6
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 5b-Epiandrosterone.mol                            
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -3.852  -2.125   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.852  -0.585   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.519   0.185   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.519  -2.895   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.185  -2.125   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.149  -2.895   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.483  -2.125   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.483  -0.585   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.816   0.185   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.281  -0.291   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.186   0.955   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.281   2.201   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.816   1.725   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.816   3.265   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.483   2.495   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.149   1.725   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.149   0.185   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.185  -0.585   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.185   0.955   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.757   3.665   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -5.186  -2.895   0.000  0.00  0.00           O+0
HETATM   22  H   UNK     0      -1.185  -3.665   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       0.149  -1.355   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       1.483   0.955   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       2.816  -1.355   0.000  0.00  0.00           H+0
CONECT    1    2    4   21                                                  
CONECT    2    1    3                                                       
CONECT    3    2   18                                                       
CONECT    4    1    5                                                       
CONECT    5    4    6   18   22                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   17   24                                             
CONECT    9    8   10   13   25                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12    9   14   15                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    8   18   23                                             
CONECT   18   17    3    5   19                                             
CONECT   19   18                                                            
CONECT   20   12                                                            
CONECT   21    1                                                            
CONECT   22    5                                                            
CONECT   23   17                                                            
CONECT   24    8                                                            
CONECT   25    9                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0000546
HETATM    1  C1  UNL     1       2.780  -0.468   1.512  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.818   0.589   0.453  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.106   1.848   0.822  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.632   1.717   0.885  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.007   0.891  -0.181  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.820  -0.371  -0.496  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.136  -1.194  -1.524  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.174  -1.695  -0.955  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.547  -1.008   0.323  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.983  -1.323   0.649  1.00  0.00           C  
HETATM   11  C11 UNL     1      -3.956  -0.836  -0.369  1.00  0.00           C  
HETATM   12  O1  UNL     1      -5.243  -0.931   0.209  1.00  0.00           O  
HETATM   13  C12 UNL     1      -3.733   0.607  -0.757  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.299   0.950  -0.947  1.00  0.00           C  
HETATM   15  C14 UNL     1      -1.394   0.491   0.157  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.877   1.124   1.445  1.00  0.00           C  
HETATM   17  C16 UNL     1       2.187   0.097  -0.859  1.00  0.00           C  
HETATM   18  C17 UNL     1       3.141  -0.961  -1.272  1.00  0.00           C  
HETATM   19  C18 UNL     1       4.508  -0.436  -0.817  1.00  0.00           C  
HETATM   20  C19 UNL     1       4.203   0.781   0.013  1.00  0.00           C  
HETATM   21  O2  UNL     1       5.004   1.654   0.204  1.00  0.00           O  
HETATM   22  H1  UNL     1       2.775  -1.505   1.108  1.00  0.00           H  
HETATM   23  H2  UNL     1       3.737  -0.398   2.103  1.00  0.00           H  
HETATM   24  H3  UNL     1       1.974  -0.310   2.259  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.467   2.138   1.851  1.00  0.00           H  
HETATM   26  H5  UNL     1       2.459   2.667   0.152  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.299   1.377   1.907  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.196   2.755   0.799  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.053   1.493  -1.136  1.00  0.00           H  
HETATM   30  H9  UNL     1       0.898  -0.946   0.452  1.00  0.00           H  
HETATM   31  H10 UNL     1      -0.000  -0.617  -2.465  1.00  0.00           H  
HETATM   32  H11 UNL     1       0.797  -2.046  -1.786  1.00  0.00           H  
HETATM   33  H12 UNL     1      -1.071  -2.768  -0.751  1.00  0.00           H  
HETATM   34  H13 UNL     1      -1.956  -1.470  -1.700  1.00  0.00           H  
HETATM   35  H14 UNL     1      -0.949  -1.369   1.204  1.00  0.00           H  
HETATM   36  H15 UNL     1      -3.058  -2.447   0.670  1.00  0.00           H  
HETATM   37  H16 UNL     1      -3.196  -0.984   1.684  1.00  0.00           H  
HETATM   38  H17 UNL     1      -3.953  -1.527  -1.223  1.00  0.00           H  
HETATM   39  H18 UNL     1      -5.127  -0.611   1.154  1.00  0.00           H  
HETATM   40  H19 UNL     1      -4.286   1.292  -0.078  1.00  0.00           H  
HETATM   41  H20 UNL     1      -4.240   0.733  -1.759  1.00  0.00           H  
HETATM   42  H21 UNL     1      -2.229   2.078  -0.966  1.00  0.00           H  
HETATM   43  H22 UNL     1      -1.989   0.625  -1.952  1.00  0.00           H  
HETATM   44  H23 UNL     1      -2.981   1.034   1.468  1.00  0.00           H  
HETATM   45  H24 UNL     1      -1.636   2.194   1.508  1.00  0.00           H  
HETATM   46  H25 UNL     1      -1.514   0.543   2.332  1.00  0.00           H  
HETATM   47  H26 UNL     1       2.200   0.966  -1.537  1.00  0.00           H  
HETATM   48  H27 UNL     1       2.920  -1.951  -0.879  1.00  0.00           H  
HETATM   49  H28 UNL     1       3.166  -1.028  -2.396  1.00  0.00           H  
HETATM   50  H29 UNL     1       5.169  -0.218  -1.654  1.00  0.00           H  
HETATM   51  H30 UNL     1       4.938  -1.225  -0.157  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   17   20
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6   15   29
CONECT    6    7   17   30
CONECT    7    8   31   32
CONECT    8    9   33   34
CONECT    9   10   15   35
CONECT   10   11   36   37
CONECT   11   12   13   38
CONECT   12   39
CONECT   13   14   40   41
CONECT   14   15   42   43
CONECT   15   16
CONECT   16   44   45   46
CONECT   17   18   47
CONECT   18   19   48   49
CONECT   19   20   50   51
CONECT   20   21   21
END

HMDB0000546
     RDKit          3D
Epietiocholanolone
 51 54  0  0  0  0  0  0  0  0999 V2000
    2.7805   -0.4679    1.5124 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8179    0.5893    0.4532 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1058    1.8485    0.8219 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6323    1.7166    0.8851 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0072    0.8912   -0.1805 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8198   -0.3710   -0.4961 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1362   -1.1943   -1.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1738   -1.6952   -0.9550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5468   -1.0085    0.3227 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9827   -1.3228    0.6489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9564   -0.8362   -0.3692 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2434   -0.9305    0.2094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7334    0.6066   -0.7567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2994    0.9505   -0.9469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3938    0.4914    0.1569 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8768    1.1244    1.4453 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1867    0.0971   -0.8591 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1407   -0.9611   -1.2718 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5084   -0.4362   -0.8168 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2034    0.7807    0.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0041    1.6545    0.2036 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7754   -1.5051    1.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7375   -0.3977    2.1031 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9742   -0.3100    2.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4665    2.1376    1.8514 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4590    2.6665    0.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2990    1.3765    1.9074 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1955    2.7549    0.7988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0527    1.4925   -1.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8980   -0.9462    0.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0003   -0.6174   -2.4648 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7974   -2.0464   -1.7859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0709   -2.7679   -0.7505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9558   -1.4704   -1.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9492   -1.3692    1.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0579   -2.4471    0.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1959   -0.9838    1.6838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9530   -1.5270   -1.2232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1273   -0.6108    1.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2863    1.2919   -0.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2399    0.7328   -1.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2288    2.0776   -0.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9886    0.6250   -1.9518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9814    1.0340    1.4683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6358    2.1942    1.5080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5139    0.5432    2.3317 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2000    0.9660   -1.5373 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9205   -1.9505   -0.8786 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1655   -1.0276   -2.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1690   -0.2181   -1.6542 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9383   -1.2245   -0.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 17  2  1  0
 20  2  1  0
 15  5  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  6
  6 30  1  1
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  1
 10 36  1  0
 10 37  1  0
 11 38  1  6
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 16 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  6
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
M  END

View in JSmol

Synonyms

Value	Source
3b-Etiocholanolone	HMDB
3b-Hydroxy-17-oxo-5b-androstane	HMDB
3b-Hydroxy-5b-androstan-17-one	HMDB
3b-Hydroxy-5b-androstane-17-one	HMDB
3b-Hydroxyetiocholan-17-one	HMDB
5b-Androstan-3b-ol-17-one	HMDB
5b-Androstane-3b-ol-17-one	HMDB
5b-Epiandrosterone	HMDB
b-Etiocholanolone	HMDB
beta-Etiocholanolone	HMDB
Epi-5b-androsterone	HMDB
Epiaetiocholanolone	HMDB
Etiocholan-3b-ol-17-one	HMDB
M1A	HMDB
Methyl-1-alpha	HMDB

Chemical Formula

C₁₉H₃₀O₂

Average Mass

290.4403 Da

Monoisotopic Mass

290.22458 Da

IUPAC Name

(1S,2S,5S,7R,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one

Traditional Name

(1S,2S,5S,7R,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one

CAS Registry Number

571-31-3

SMILES

[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@@H](O)CC[C@]12C

InChI Identifier

InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12-,13+,14+,15+,16+,18+,19+/m1/s1

InChI Key

QGXBDMJGAMFCBF-XRJZGPCZSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Androstane steroids

Direct Parent

Androgens and derivatives

Alternative Parents

Substituents

Androgen-skeleton
3-hydroxysteroid
3-beta-hydroxysteroid
Oxosteroid
17-oxosteroid
Hydroxysteroid
Cyclic alcohol
Secondary alcohol
Ketone
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

C19 steroids (androgens) and derivatives (LMST02020104 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	154 - 155 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0063 g/L	ALOGPS
logP	3.71	ALOGPS
logP	3.77	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	18.3	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	83.81 m³·mol⁻¹	ChemAxon
Polarizability	34.65 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000546

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022109

KNApSAcK ID

Not Available

Chemspider ID

216866

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Epietiocholanolone

METLIN ID

5531

PubChem Compound

247732

PDB ID

Not Available

ChEBI ID

542034

Good Scents ID

Not Available

References

General References

Eapen J, Ayoola R, Subramanian RM: 'The efficacy of extracorporeal liver support with molecular adsorbent recirculating system in severe drug-induced liver injury'. Oxf Med Case Reports. 2018 Jan 2;2018(1):omx077. doi: 10.1093/omcr/omx077. eCollection 2018 Jan. [PubMed:29308212 ]

Showing NP-Card for Epietiocholanolone (NP0000135)

MOL for NP0000135 (Epietiocholanolone)

3D MOL for NP0000135 (Epietiocholanolone)

3D SDF for NP0000135 (Epietiocholanolone)

3D-SDF for NP0000135 (Epietiocholanolone)

PDB for NP0000135 (Epietiocholanolone)

3D PDB for NP0000135 (Epietiocholanolone)

SMILES for NP0000135 (Epietiocholanolone)

INCHI for NP0000135 (Epietiocholanolone)

Structure for NP0000135 (Epietiocholanolone)

3D Structure for NP0000135 (Epietiocholanolone)