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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:03 UTC

HMDB ID

HMDB0000546

Secondary Accession Numbers

HMDB00546

Metabolite Identification

Common Name

Epietiocholanolone

Description

Epietiocholanolone, also known as 5b-epiandrosterone or M1A, 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. Thus, epietiocholanolone is considered to be a steroid. Based on a literature review very few articles have been published on Epietiocholanolone.

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>
HMDB0000546

> <DATABASE_NAME>
hmdb

> <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 View Stereo Labels

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 Molecular Weight

290.4403

Monoisotopic Molecular Weight

290.224580204

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

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 )

Ontology

Physiological effect

Health effect

Schizophrenia (HMDB: HMDB0000546)

Disposition

Biological location

Cell membrane (HMDB: HMDB0000546)

Biofluid or Excreta

Blood (HMDB: HMDB0000546)
Urine (HMDB: HMDB0000546)

Tissue substructure

Hepatic tissue (HMDB: HMDB0000546)

Organ

Kidney (HMDB: HMDB0000546)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 17716701)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000546)

Source

Endogenous

Endogenous (HMDB: HMDB0000546)

Exogenous

Food

Food (HMDB: HMDB0000546)

Animal origin

Poultry

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0000546)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0000546)

Cellular process

Cell signaling (HMDB: HMDB0000546)

System process

Reproduction (HMDB: HMDB0000546)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0000546)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0000546)

Molecular messenger

Hormone (HMDB: HMDB0000546)

Industrial application

Emulsifier (HMDB: HMDB0000546)

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000546)

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	170.593	31661259
DarkChem	[M-H]-	165.94	31661259
AllCCS	[M+H]+	175.345	32859911
AllCCS	[M-H]-	178.968	32859911
DeepCCS	[M-2H]-	203.457	30932474
DeepCCS	[M+Na]+	178.316	30932474
AllCCS	[M+H]+	175.3	32859911
AllCCS	[M+H-H2O]+	172.4	32859911
AllCCS	[M+NH4]+	178.1	32859911
AllCCS	[M+Na]+	178.9	32859911
AllCCS	[M-H]-	179.0	32859911
AllCCS	[M+Na-2H]-	179.2	32859911
AllCCS	[M+HCOO]-	179.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Epietiocholanolone	[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	2294.0	Standard polar	33892256
Epietiocholanolone	[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	2445.5	Standard non polar	33892256
Epietiocholanolone	[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	2635.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Epietiocholanolone,1TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CC[C@@H]4C[C@@H](O[Si](C)(C)C)CC[C@]34C)[C@@H]1CCC2=O	2570.6	Semi standard non polar	33892256
Epietiocholanolone,1TMS,isomer #2	C[C@]12CC[C@H]3[C@@H](CC[C@@H]4C[C@@H](O)CC[C@]34C)[C@@H]1CC=C2O[Si](C)(C)C	2576.5	Semi standard non polar	33892256
Epietiocholanolone,2TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CC[C@@H]4C[C@@H](O[Si](C)(C)C)CC[C@]34C)[C@@H]1CC=C2O[Si](C)(C)C	2600.9	Semi standard non polar	33892256
Epietiocholanolone,2TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CC[C@@H]4C[C@@H](O[Si](C)(C)C)CC[C@]34C)[C@@H]1CC=C2O[Si](C)(C)C	2517.3	Standard non polar	33892256
Epietiocholanolone,2TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CC[C@@H]4C[C@@H](O[Si](C)(C)C)CC[C@]34C)[C@@H]1CC=C2O[Si](C)(C)C	2936.0	Standard polar	33892256
Epietiocholanolone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1CC[C@]2(C)[C@H]3CC[C@]4(C)C(=O)CC[C@H]4[C@@H]3CC[C@@H]2C1	2814.7	Semi standard non polar	33892256
Epietiocholanolone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C	2849.6	Semi standard non polar	33892256
Epietiocholanolone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3133.8	Semi standard non polar	33892256
Epietiocholanolone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	2774.2	Standard non polar	33892256
Epietiocholanolone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3181.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Epietiocholanolone GC-MS (Non-derivatized) - 70eV, Positive	splash10-03ea-0390000000-17f2f9f14aa5e282a19a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epietiocholanolone GC-MS (1 TMS) - 70eV, Positive	splash10-001i-2169000000-bf71d6f9c1a2a4af0d20	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epietiocholanolone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epietiocholanolone GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epietiocholanolone GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epietiocholanolone GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epietiocholanolone Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0a4i-0690000000-3a0cb488894ffd730532	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epietiocholanolone Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0a5a-3910000000-0fea9c2b9985a4b5c4fc	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epietiocholanolone Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0uxu-6691000000-500e59c2f0eb04cba0d8	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epietiocholanolone LC-ESI-qTof , Positive-QTOF	splash10-0gx3-0953000000-85e6abfd3e71f7e303f9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epietiocholanolone , positive-QTOF	splash10-0a4j-0920100000-b9aa287b6300cd9902b6	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epietiocholanolone 10V, Positive-QTOF	splash10-00dl-0090000000-fb385ad40b5d4ae1a6d9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epietiocholanolone 20V, Positive-QTOF	splash10-00dm-0290000000-6287ec557af150ef07fe	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epietiocholanolone 40V, Positive-QTOF	splash10-000t-3690000000-da6f3211b1e397dcf1ae	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epietiocholanolone 10V, Negative-QTOF	splash10-000i-0090000000-03f14a475acfab5558d6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epietiocholanolone 20V, Negative-QTOF	splash10-000i-0090000000-5e4902f7af7820145954	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epietiocholanolone 40V, Negative-QTOF	splash10-06xx-2090000000-97cca29f0df7b3cc3714	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epietiocholanolone 10V, Positive-QTOF	splash10-0006-0090000000-afb176951034ef62419f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epietiocholanolone 20V, Positive-QTOF	splash10-052e-0930000000-1ed776267953f7acda8a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epietiocholanolone 40V, Positive-QTOF	splash10-0a4j-2900000000-1ba60805778f2942bfd7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epietiocholanolone 10V, Negative-QTOF	splash10-000i-0090000000-c8c452fd99c6bb4f3631	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epietiocholanolone 20V, Negative-QTOF	splash10-000i-0090000000-c8c452fd99c6bb4f3631	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epietiocholanolone 40V, Negative-QTOF	splash10-000i-0090000000-00c0e7de4e528b98df5c	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	2012-12-04	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood

Tissue Locations

Kidney

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22944140	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	22944140	details
Blood	Detected and Quantified	0.000017 (0.000011-0.000067) uM	Adult (>18 years old)	Male	Normal	17716701	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Schizophrenia	22944140	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Schizophrenia	22944140	details

Associated Disorders and Diseases

Disease References

Schizophrenia
Bicikova M, Hill M, Ripova D, Mohr P, Hampl R: Determination of steroid metabolome as a possible tool for laboratory diagnosis of schizophrenia. J Steroid Biochem Mol Biol. 2013 Jan;133:77-83. doi: 10.1016/j.jsbmb.2012.08.009. Epub 2012 Aug 24. [PubMed:22944140 ]

Associated OMIM IDs

181500 (Schizophrenia)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Fajkos, J.; Sanda, V. Steroids. LXVI. 16-Bromo derivatives in the 5b-androstane series. Collection of Czechoslovak Chemical Communications (1962), 27 355-61.

Material Safety Data Sheet (MSDS)

Not Available

General References

Huck JH, Struys EA, Verhoeven NM, Jakobs C, van der Knaap MS: Profiling of pentose phosphate pathway intermediates in blood spots by tandem mass spectrometry: application to transaldolase deficiency. Clin Chem. 2003 Aug;49(8):1375-80. [PubMed:12881455 ]

Showing metabocard for Epietiocholanolone (HMDB0000546)

MOL for HMDB0000546 (Epietiocholanolone)

3D MOL for HMDB0000546 (Epietiocholanolone)

3D SDF for HMDB0000546 (Epietiocholanolone)

3D-SDF for HMDB0000546 (Epietiocholanolone)

PDB for HMDB0000546 (Epietiocholanolone)

3D PDB for HMDB0000546 (Epietiocholanolone)

SMILES for HMDB0000546 (Epietiocholanolone)

INCHI for HMDB0000546 (Epietiocholanolone)

Structure for HMDB0000546 (Epietiocholanolone)

3D Structure for HMDB0000546 (Epietiocholanolone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra