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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:01 UTC

HMDB ID

HMDB0000365

Secondary Accession Numbers

HMDB00365

Metabolite Identification

Common Name

Epiandrosterone

Description

Epiandrosterone is a naturally occurring steroid synthesized in the adrenal cortex, gonads, brain, and gastrointestinal tract. It is less active than androsterone and excreted in small amounts in normal human urine. Epiandrosterone is a metabolite of the most abundant adrenal androgenic steroid dehydroepiandrosterone (DHEA) in young adult humans, but is not completely inactive and is considered an effector as well. Epiandrosterone is a precursor or substrate for cytochrome P450 species and enzymes (EC 1.14.13.100, 25-hydroxycholesterol 7alpha-hydroxylase) that produce 7alpha- and 7beta-hydroxylated metabolites in the human brain and other organs. These 7-hydroxylated derivatives exert anti-glucocorticoid and neuroprotective effects (PMID: 17017935 , 12475725 , 15650074 , 15784286 ).

Structure

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

HMDB0000365
     RDKit          3D
Epiandrosterone
 51 54  0  0  0  0  0  0  0  0999 V2000
   -3.0501   -0.8800   -0.8907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9500    0.3002    0.0426 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3393    1.4591   -0.6703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9211    1.1914   -1.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0630    0.6270    0.0219 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7723   -0.5656    0.6774 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0406   -1.1567    1.7892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5209   -0.9082    1.6350 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8329   -0.9554    0.1572 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2822   -1.1865   -0.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1325    0.0373    0.0327 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4089   -0.2419   -0.4526 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5914    1.2066   -0.7589 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1915    1.4835   -0.2904 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2801    0.2771   -0.5046 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2770    0.0150   -2.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0329   -0.0148    1.2298 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8628   -0.9038    2.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2370   -0.2170    1.9912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2110    0.5657    0.7271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1082    1.2912    0.3632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8841   -1.8451   -0.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3919   -0.8008   -1.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1088   -0.8881   -1.2714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4013    2.3864   -0.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9156    1.6050   -1.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8984    0.5715   -1.9877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4725    2.1862   -1.3463 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0210    1.3997    0.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9380   -1.2899   -0.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0904   -2.2763    1.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3462   -0.8805    2.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7614    0.0773    2.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0649   -1.7468    2.1170 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2733   -1.8283   -0.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6426   -1.9136    0.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4961   -1.6964   -1.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2569    0.3706    1.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7886    0.5714   -0.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6763    1.0670   -1.8514 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2082    2.0824   -0.5003 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2406    1.6770    0.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7243    2.3572   -0.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5812   -0.8061   -2.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3032   -0.3894   -2.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0680    0.9629   -2.5122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8436    0.9403    1.7524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5121   -0.9784    3.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9969   -1.9094    1.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2597    0.5092    2.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0576   -0.9393    2.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  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  6
  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  1
  6 30  1  6
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  1
 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  1
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
M  END

3b-Androsterone.mol
  Mrv1652305271900102D          

 24 27  0  0  0  0            999 V2000
   -1.3492   -0.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0637   -0.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0637   -1.3448    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7782   -1.7573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3492   -1.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348   -1.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797   -1.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942   -1.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942   -0.5198    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5086   -0.1073    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2933   -0.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7782    0.3052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2933    0.9727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5482    1.7573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5086    0.7177    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5086    1.5427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942    1.1302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797    0.7177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797   -0.1073    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6348   -0.5198    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6348    0.3052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797   -0.9323    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942    0.3052    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5086   -0.9323    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
  3  4  1  1  0  0  0
  3  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
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  9 19  1  0  0  0  0
 19 20  1  0  0  0  0
  1 20  1  0  0  0  0
  6 20  1  0  0  0  0
 20 21  1  1  0  0  0
 19 22  1  6  0  0  0
  9 23  1  1  0  0  0
 10 24  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0000365

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2C[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-/m0/s1

> <INCHI_KEY>
QGXBDMJGAMFCBF-QRIARFFBSA-N

> <FORMULA>
C19H30O2

> <MOLECULAR_WEIGHT>
290.4403

> <EXACT_MASS>
290.224580204

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
34.70085686732426

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,5S,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>
83.80890000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.37e-03 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0000365
     RDKit          3D
Epiandrosterone
 51 54  0  0  0  0  0  0  0  0999 V2000
   -3.0501   -0.8800   -0.8907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9500    0.3002    0.0426 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3393    1.4591   -0.6703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9211    1.1914   -1.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0630    0.6270    0.0219 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7723   -0.5656    0.6774 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0406   -1.1567    1.7892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5209   -0.9082    1.6350 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8329   -0.9554    0.1572 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2822   -1.1865   -0.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1325    0.0373    0.0327 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4089   -0.2419   -0.4526 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5914    1.2066   -0.7589 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1915    1.4835   -0.2904 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2801    0.2771   -0.5046 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2770    0.0150   -2.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0329   -0.0148    1.2298 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8628   -0.9038    2.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2370   -0.2170    1.9912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2110    0.5657    0.7271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1082    1.2912    0.3632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8841   -1.8451   -0.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3919   -0.8008   -1.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1088   -0.8881   -1.2714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4013    2.3864   -0.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9156    1.6050   -1.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8984    0.5715   -1.9877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4725    2.1862   -1.3463 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0210    1.3997    0.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9380   -1.2899   -0.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0904   -2.2763    1.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3462   -0.8805    2.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7614    0.0773    2.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0649   -1.7468    2.1170 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2733   -1.8283   -0.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6426   -1.9136    0.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4961   -1.6964   -1.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2569    0.3706    1.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7886    0.5714   -0.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6763    1.0670   -1.8514 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2082    2.0824   -0.5003 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2406    1.6770    0.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7243    2.3572   -0.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5812   -0.8061   -2.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3032   -0.3894   -2.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0680    0.9629   -2.5122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8436    0.9403    1.7524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5121   -0.9784    3.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9969   -1.9094    1.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2597    0.5092    2.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0576   -0.9393    2.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  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  6
  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  1
  6 30  1  6
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  1
 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  1
 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: 3b-Androsterone.mol                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -2.519  -0.200   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.852  -0.970   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.852  -2.510   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -5.186  -3.280   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.519  -3.280   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.185  -2.510   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.149  -3.280   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.483  -2.510   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.483  -0.970   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.816  -0.200   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.281  -0.676   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.186   0.570   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.281   1.816   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.757   3.280   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.816   1.340   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.816   2.880   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.483   2.110   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.149   1.340   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.149  -0.200   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.185  -0.970   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.185   0.570   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0       0.149  -1.740   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       1.483   0.570   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       2.816  -1.740   0.000  0.00  0.00           H+0
CONECT    1    2   20                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   20                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   19   23                                             
CONECT   10    9   11   15   24                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   10   16   17                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    9   20   22                                             
CONECT   20   19    1    6   21                                             
CONECT   21   20                                                            
CONECT   22   19                                                            
CONECT   23    9                                                            
CONECT   24   10                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0000365
HETATM    1  C1  UNL     1      -3.050  -0.880  -0.891  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.950   0.300   0.043  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.339   1.459  -0.670  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.921   1.191  -1.054  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.063   0.627   0.022  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.772  -0.566   0.677  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.041  -1.157   1.789  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.521  -0.908   1.635  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.833  -0.955   0.157  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.282  -1.187  -0.098  1.00  0.00           C  
HETATM   11  C11 UNL     1       4.132   0.037   0.033  1.00  0.00           C  
HETATM   12  O1  UNL     1       5.409  -0.242  -0.453  1.00  0.00           O  
HETATM   13  C12 UNL     1       3.591   1.207  -0.759  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.192   1.484  -0.290  1.00  0.00           C  
HETATM   15  C14 UNL     1       1.280   0.277  -0.505  1.00  0.00           C  
HETATM   16  C15 UNL     1       1.277   0.015  -2.003  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.033  -0.015   1.230  1.00  0.00           C  
HETATM   18  C17 UNL     1      -2.863  -0.904   2.058  1.00  0.00           C  
HETATM   19  C18 UNL     1      -4.237  -0.217   1.991  1.00  0.00           C  
HETATM   20  C19 UNL     1      -4.211   0.566   0.727  1.00  0.00           C  
HETATM   21  O2  UNL     1      -5.108   1.291   0.363  1.00  0.00           O  
HETATM   22  H1  UNL     1      -2.884  -1.845  -0.418  1.00  0.00           H  
HETATM   23  H2  UNL     1      -2.392  -0.801  -1.773  1.00  0.00           H  
HETATM   24  H3  UNL     1      -4.109  -0.888  -1.271  1.00  0.00           H  
HETATM   25  H4  UNL     1      -2.401   2.386  -0.061  1.00  0.00           H  
HETATM   26  H5  UNL     1      -2.916   1.605  -1.623  1.00  0.00           H  
HETATM   27  H6  UNL     1      -0.898   0.572  -1.988  1.00  0.00           H  
HETATM   28  H7  UNL     1      -0.472   2.186  -1.346  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.021   1.400   0.828  1.00  0.00           H  
HETATM   30  H9  UNL     1      -0.938  -1.290  -0.160  1.00  0.00           H  
HETATM   31  H10 UNL     1      -0.090  -2.276   1.717  1.00  0.00           H  
HETATM   32  H11 UNL     1      -0.346  -0.880   2.785  1.00  0.00           H  
HETATM   33  H12 UNL     1       1.761   0.077   2.078  1.00  0.00           H  
HETATM   34  H13 UNL     1       2.065  -1.747   2.117  1.00  0.00           H  
HETATM   35  H14 UNL     1       1.273  -1.828  -0.268  1.00  0.00           H  
HETATM   36  H15 UNL     1       3.643  -1.914   0.686  1.00  0.00           H  
HETATM   37  H16 UNL     1       3.496  -1.696  -1.066  1.00  0.00           H  
HETATM   38  H17 UNL     1       4.257   0.371   1.079  1.00  0.00           H  
HETATM   39  H18 UNL     1       5.789   0.571  -0.909  1.00  0.00           H  
HETATM   40  H19 UNL     1       3.676   1.067  -1.851  1.00  0.00           H  
HETATM   41  H20 UNL     1       4.208   2.082  -0.500  1.00  0.00           H  
HETATM   42  H21 UNL     1       2.241   1.677   0.799  1.00  0.00           H  
HETATM   43  H22 UNL     1       1.724   2.357  -0.758  1.00  0.00           H  
HETATM   44  H23 UNL     1       0.581  -0.806  -2.260  1.00  0.00           H  
HETATM   45  H24 UNL     1       2.303  -0.389  -2.244  1.00  0.00           H  
HETATM   46  H25 UNL     1       1.068   0.963  -2.512  1.00  0.00           H  
HETATM   47  H26 UNL     1      -1.844   0.940   1.752  1.00  0.00           H  
HETATM   48  H27 UNL     1      -2.512  -0.978   3.111  1.00  0.00           H  
HETATM   49  H28 UNL     1      -2.997  -1.909   1.666  1.00  0.00           H  
HETATM   50  H29 UNL     1      -4.260   0.509   2.853  1.00  0.00           H  
HETATM   51  H30 UNL     1      -5.058  -0.939   2.039  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

HMDB0000365
     RDKit          3D
Epiandrosterone
 51 54  0  0  0  0  0  0  0  0999 V2000
   -3.0501   -0.8800   -0.8907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9500    0.3002    0.0426 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3393    1.4591   -0.6703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9211    1.1914   -1.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0630    0.6270    0.0219 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7723   -0.5656    0.6774 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0406   -1.1567    1.7892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5209   -0.9082    1.6350 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8329   -0.9554    0.1572 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2822   -1.1865   -0.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1325    0.0373    0.0327 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4089   -0.2419   -0.4526 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5914    1.2066   -0.7589 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1915    1.4835   -0.2904 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2801    0.2771   -0.5046 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2770    0.0150   -2.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0329   -0.0148    1.2298 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8628   -0.9038    2.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2370   -0.2170    1.9912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2110    0.5657    0.7271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1082    1.2912    0.3632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8841   -1.8451   -0.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3919   -0.8008   -1.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1088   -0.8881   -1.2714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4013    2.3864   -0.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9156    1.6050   -1.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8984    0.5715   -1.9877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4725    2.1862   -1.3463 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0210    1.3997    0.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9380   -1.2899   -0.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0904   -2.2763    1.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3462   -0.8805    2.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7614    0.0773    2.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0649   -1.7468    2.1170 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2733   -1.8283   -0.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6426   -1.9136    0.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4961   -1.6964   -1.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2569    0.3706    1.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7886    0.5714   -0.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6763    1.0670   -1.8514 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2082    2.0824   -0.5003 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2406    1.6770    0.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7243    2.3572   -0.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5812   -0.8061   -2.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3032   -0.3894   -2.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0680    0.9629   -2.5122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8436    0.9403    1.7524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5121   -0.9784    3.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9969   -1.9094    1.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2597    0.5092    2.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0576   -0.9393    2.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  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  6
  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  1
  6 30  1  6
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  1
 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  1
 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
3-Epiandrosterone	HMDB
3b-Androsterone	HMDB
3b-Hydroxy-17-oxo-5a-androstane	HMDB
3b-Hydroxy-5a-androstan-17-one	HMDB
3b-Hydroxy-5a-androstane-17-one	HMDB
3b-Hydroxyandrostan-17-one	HMDB
3b-Hydroxyetioallocholan-17-one	HMDB
3b-OH-5a-Androstane-17-one	HMDB
5a-Androstan-3b-ol-17-one	HMDB
5a-Androstane-3b-ol-17-one	HMDB
D-Epiandrosterone	HMDB
Epi-andosterone	HMDB
Epi-androsterone	HMDB
Iso-androsterone	HMDB
Isoandrosterone	HMDB
trans-Androsterone	HMDB
(3Β,5α)-3-hydroxyandrostan-17-one	HMDB
3Β-androsterone	HMDB
3Β-hydroxy-17-oxo-5α-androstane	HMDB
3Β-hydroxy-5α-androstan-17-one	HMDB
3Β-hydroxy-5α-androstane-17-one	HMDB
3Β-hydroxyandrostan-17-one	HMDB
3Β-hydroxyetioallocholan-17-one	HMDB
3Β-OH-5α-androstane-17-one	HMDB
5Α-androstan-17-one-3β-ol	HMDB
5Α-androstan-3β-ol-17-one	HMDB
5Α-androstane-3β-ol-17-one	HMDB
(3beta,5alpha)-3-Hydroxyandrostan-17-one	HMDB
3beta-Androsterone	HMDB
3beta-Hydroxy-17-oxo-5alpha-androstane	HMDB
3beta-Hydroxy-5alpha-androstan-17-one	HMDB
3beta-Hydroxy-5alpha-androstane-17-one	HMDB
3beta-Hydroxyandrostan-17-one	HMDB
3beta-Hydroxyetioallocholan-17-one	HMDB
3beta-OH-5alpha-Androstane-17-one	HMDB
5alpha-Androstan-17-one-3beta-ol	HMDB
5alpha-Androstan-3beta-ol-17-one	HMDB
5alpha-Androstane-3beta-ol-17-one	HMDB

Chemical Formula

C₁₉H₃₀O₂

Average Molecular Weight

290.4403

Monoisotopic Molecular Weight

290.224580204

IUPAC Name

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

CAS Registry Number

481-29-8

SMILES

[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2C[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-/m0/s1

InChI Key

QGXBDMJGAMFCBF-QRIARFFBSA-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

Not Available

Ontology

Physiological effect

Health effect

Nervous system disorder

Central nervous system disorder

Psychiatric disorder

Schizophrenia (HMDB: HMDB0000365)

Adipose tissue (HMDB: HMDB0000365)
Adipose tissue (HMDB: HMDB0000365)

Nervous tissue

Hepatic tissue (HMDB: HMDB0000365)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 17716701)

Cellular substructure

Organelle

Endoplasmic reticulum (HMDB: HMDB0000365)

Organ

Gland

Adrenal Gland (HMDB: HMDB0000365)
Adrenal Gland (HMDB: HMDB0000365)

Excreta

Biofluid or Excreta

Feces (PMID: 27275383)
Urine (HMDB: HMDB0000365)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000365)

Source

Endogenous

Endogenous (HMDB: HMDB0000365)

Animal

Animal (HMDB: HMDB0000365)

Exogenous

Food

Food (HMDB: HMDB0000365)

Animal origin

Poultry

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)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

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)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0000365)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0000365)

Molecular messenger

Hormone (HMDB: HMDB0000365)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000365)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	178 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.02 mg/mL at 23 °C	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	34.7 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]+	167.235	31661259
DarkChem	[M-H]-	162.807	31661259
AllCCS	[M+H]+	175.466	32859911
AllCCS	[M-H]-	178.968	32859911
DeepCCS	[M-2H]-	205.134	30932474
DeepCCS	[M+Na]+	179.65	30932474
AllCCS	[M+H]+	175.5	32859911
AllCCS	[M+H-H2O]+	172.5	32859911
AllCCS	[M+NH4]+	178.3	32859911
AllCCS	[M+Na]+	179.1	32859911
AllCCS	[M-H]-	179.0	32859911
AllCCS	[M+Na-2H]-	179.2	32859911
AllCCS	[M+HCOO]-	179.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.74 minutes	32390414
Predicted by Siyang on May 30, 2022	15.9518 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.51 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2548.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	411.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	206.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	189.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	494.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	642.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	656.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	106.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1266.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	454.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1493.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	368.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	428.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	294.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	415.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	23.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Epiandrosterone	[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2C[C@@H](O)CC[C@]12C	2280.7	Standard polar	33892256
Epiandrosterone	[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2C[C@@H](O)CC[C@]12C	2441.5	Standard non polar	33892256
Epiandrosterone	[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2C[C@@H](O)CC[C@]12C	2637.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Epiandrosterone,1TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CCC4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CCC2=O	2578.5	Semi standard non polar	33892256
Epiandrosterone,1TMS,isomer #2	C[C@]12CC[C@H]3[C@@H](CCC4C[C@@H](O)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C	2579.0	Semi standard non polar	33892256
Epiandrosterone,2TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CCC4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C	2602.6	Semi standard non polar	33892256
Epiandrosterone,2TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CCC4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C	2511.5	Standard non polar	33892256
Epiandrosterone,2TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CCC4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C	2920.4	Standard polar	33892256
Epiandrosterone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(C)C(CC[C@H]3[C@@H]4CCC(=O)[C@@]4(C)CC[C@@H]32)C1	2818.4	Semi standard non polar	33892256
Epiandrosterone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CCC4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C	2849.6	Semi standard non polar	33892256
Epiandrosterone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CCC4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3134.5	Semi standard non polar	33892256
Epiandrosterone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CCC4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	2771.5	Standard non polar	33892256
Epiandrosterone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CCC4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3167.0	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)
Endoplasmic reticulum

Biospecimen Locations

Blood
Feces

Tissue Locations

Adipose Tissue
Adrenal Gland

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	2.9 (2.65-4.19) uM	Adult (>18 years old)	Male	Normal	17716701	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22944140	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
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	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 ]
Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]

Associated OMIM IDs

181500 (Schizophrenia)
114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021984

KNApSAcK ID

Not Available

Chemspider ID

9230560

KEGG Compound ID

C07635

BioCyc ID

Not Available

BiGG ID

45201

Wikipedia Link

Epiandrosterone

METLIN ID

Not Available

PubChem Compound

11055399

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

Johnson, Wm. S.; Bannister, Brian; Pappo, Raphael. Steroid total synthesis-hydrochrysene approach. VII. Metal-in-ammonia reduction of the aromatic nucleus. dl-Epiandrosterone and the lumi epimer. Journal of the American Chemical Society (1956), 78 6331-9.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Mitamura K, Setaka M, Shimada K, Honma S, Namiki M, Koh E, Mizokami A: Determination of sulfates of androsterone and epiandrosterone in human serum using isotope diluted liquid chromatography-electrospray ionization-mass spectrometry. Biomed Chromatogr. 2005 Dec;19(10):796-801. [PubMed:15954157 ]
Chalbot S, Morfin R: Human liver S9 fractions: metabolism of dehydroepiandrosterone, epiandrosterone, and related 7-hydroxylated derivatives. Drug Metab Dispos. 2005 Apr;33(4):563-9. Epub 2005 Jan 13. [PubMed:15650074 ]
Johnson MD, Bebb RA, Sirrs SM: Uses of DHEA in aging and other disease states. Ageing Res Rev. 2002 Feb;1(1):29-41. [PubMed:12039447 ]
Norman RJ, Maharaj C, Adhikari M, Joubert SM: Adrenal sensitivity to adrenocorticotrophin in twin neonates--effect of birth order and growth retardation. S Afr Med J. 1984 Jul 21;66(3):90-2. [PubMed:6330917 ]
Hungerford NL, Sortais B, Smart CG, McKinney AR, Ridley DD, Stenhouse AM, Suann CJ, Munn KJ, Sillence MN, McLeod MD: Analysis of anabolic steroids in the horse: development of a generic ELISA for the screening of 17alpha-alkyl anabolic steroid metabolites. J Steroid Biochem Mol Biol. 2005 Aug;96(3-4):317-34. [PubMed:16040239 ]
Thijssen JH, Daroszewski J, Milewicz A, Blankenstein MA: Local aromatase activity in human breast tissues. J Steroid Biochem Mol Biol. 1993 Mar;44(4-6):577-82. [PubMed:8476769 ]
Matsuzaki Y, Honda A: Dehydroepiandrosterone and its derivatives: potentially novel anti-proliferative and chemopreventive agents. Curr Pharm Des. 2006;12(26):3411-21. [PubMed:17017935 ]
Yoshida S, Honda A, Matsuzaki Y, Fukushima S, Tanaka N, Takagiwa A, Fujimoto Y, Miyazaki H, Salen G: Anti-proliferative action of endogenous dehydroepiandrosterone metabolites on human cancer cell lines. Steroids. 2003 Jan;68(1):73-83. [PubMed:12475725 ]
Chalbot S, Morfin R: Neurosteroids: metabolism in human intestine microsomes. Steroids. 2005 Apr;70(4):319-26. [PubMed:15784286 ]

Enzymes

Enzyme Details

1. 25-hydroxycholesterol 7-alpha-hydroxylase

General function:: Involved in monooxygenase activity
Specific function:: Not Available
Gene Name:: CYP7B1
Uniprot ID:: O75881
Molecular weight:: 58255.325

Showing metabocard for Epiandrosterone (HMDB0000365)

MOL for HMDB0000365 (Epiandrosterone)

3D MOL for HMDB0000365 (Epiandrosterone)

3D SDF for HMDB0000365 (Epiandrosterone)

3D-SDF for HMDB0000365 (Epiandrosterone)

PDB for HMDB0000365 (Epiandrosterone)

3D PDB for HMDB0000365 (Epiandrosterone)

SMILES for HMDB0000365 (Epiandrosterone)

INCHI for HMDB0000365 (Epiandrosterone)

Structure for HMDB0000365 (Epiandrosterone)

3D Structure for HMDB0000365 (Epiandrosterone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes