Np mrd loader

Showing NP-Card for Epietiocholanolone (NP0000135)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2020-11-24 22:13:07 UTC
NP-MRD IDNP0000135
Secondary Accession NumbersNone
Natural Product Identification
Common NameEpietiocholanolone
DescriptionEpietiocholanolone is an anabolic steroid similar in structure to androstenedione. Used by body-builders to add muscle mass, but with unknown side effects.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000135 (Epietiocholanolone)

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
Download

3D MOL for NP0000135 (Epietiocholanolone)

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
Download

3D SDF for NP0000135 (Epietiocholanolone)

5b-Epiandrosterone.mol
  Mrv1652305271900102D          

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

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
QGXBDMJGAMFCBF-XRJZGPCZSA-N

> <FORMULA>
C19H30O2

> <MOLECULAR_WEIGHT>
290.4403

> <EXACT_MASS>
290.224580204

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
34.654086773768185

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.71

> <JCHEM_LOGP>
3.7672845366666667

> <ALOGPS_LOGS>
-4.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.96171995034024

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.296396321120497

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3569559187002107

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
83.80889999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.37e-03 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0000135 (Epietiocholanolone)

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
Download

PDB for NP0000135 (Epietiocholanolone)

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
Download

3D PDB for NP0000135 (Epietiocholanolone)

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
Download

SMILES for NP0000135 (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
Download

INCHI for NP0000135 (Epietiocholanolone)

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
Download
View in JSmol
Synonyms
ValueSource
3b-EtiocholanoloneHMDB
3b-Hydroxy-17-oxo-5b-androstaneHMDB
3b-Hydroxy-5b-androstan-17-oneHMDB
3b-Hydroxy-5b-androstane-17-oneHMDB
3b-Hydroxyetiocholan-17-oneHMDB
5b-Androstan-3b-ol-17-oneHMDB
5b-Androstane-3b-ol-17-oneHMDB
5b-EpiandrosteroneHMDB
b-EtiocholanoloneHMDB
beta-EtiocholanoloneHMDB
Epi-5b-androsteroneHMDB
EpiaetiocholanoloneHMDB
Etiocholan-3b-ol-17-oneHMDB
M1AHMDB
Methyl-1-alphaHMDB
Chemical FormulaC19H30O2
Average Mass290.4403 Da
Monoisotopic Mass290.22458 Da
IUPAC Name(1S,2S,5S,7R,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one
Traditional Name(1S,2S,5S,7R,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one
CAS Registry Number571-31-3
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 KeyQGXBDMJGAMFCBF-XRJZGPCZSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAndrostane steroids
Direct ParentAndrogens 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 FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point154 - 155 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0063 g/LALOGPS
logP3.71ALOGPS
logP3.77ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity83.81 m³·mol⁻¹ChemAxon
Polarizability34.65 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000546
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022109
KNApSAcK IDNot Available
Chemspider ID216866
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEpietiocholanolone
METLIN ID5531
PubChem Compound247732
PDB IDNot Available
ChEBI ID542034
Good Scents IDNot Available
References
General References
  1. 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 ]
  2. Eapen J, Ayoola R, Subramanian RM: 'The efficacy of extracorporeal liver support with molecular adsorbent recirculating system in severe drug-induced liver injury'. Oxf Med Case Reports. 2018 Jan 2;2018(1):omx077. doi: 10.1093/omcr/omx077. eCollection 2018 Jan. [PubMed:29308212 ]