NP-MRD: Showing NP-Card for Epiandrosterone (NP0001298)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2020-11-24 22:22:20 UTC

NP-MRD ID

NP0001298

Secondary Accession Numbers

None

Natural Product 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>
NP0001298

> <DATABASE_NAME>
NP-MRD

> <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

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 Mass

290.4403 Da

Monoisotopic Mass

290.22458 Da

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

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

Not Available

Physical Properties

State

Solid

Experimental 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

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	34.7 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

External Links

HMDB ID

HMDB0000365

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

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 ]

Showing NP-Card for Epiandrosterone (NP0001298)

MOL for NP0001298 (Epiandrosterone)

3D MOL for NP0001298 (Epiandrosterone)

3D SDF for NP0001298 (Epiandrosterone)

3D-SDF for NP0001298 (Epiandrosterone)

PDB for NP0001298 (Epiandrosterone)

3D PDB for NP0001298 (Epiandrosterone)

SMILES for NP0001298 (Epiandrosterone)

INCHI for NP0001298 (Epiandrosterone)

Structure for NP0001298 (Epiandrosterone)

3D Structure for NP0001298 (Epiandrosterone)