NP-MRD: Showing NP-Card for Etiocholanolone (NP0000565)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2020-11-24 22:16:30 UTC

NP-MRD ID

NP0000565

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Etiocholanolone

Description

Etiocholanolone is the 5-beta-reduced isomer of androsterone. Etiocholanolone is a major metabolite of testosterone and androstenedione in many mammalian species including humans. It is excreted in the urine and is androgenically inactive. Classified a ketosteroid, it causes fever (it is a pyrogen), immunostimulation and leukocytosis. The pyrogenic effect of Etiocholanolone has been shown to be due to the release of interleukin-1 (IL-1) from the leukocytes that are mobilized in response to its production or injection. Etiocholanolone has anticonvulsant activity and may be an endogenous modulator of seizure susceptibility. Significantly increased values of etiocholanolone (along with testoterone and androsterone) an be detected in the urine of men with androgenic alopecia (male pattern baldness).

Structure

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

AE2
  Mrv1652305271900122D          

 26 29  0  0  0  0            999 V2000
    1.3350   -0.7296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1471   -0.5844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4274    0.1916    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2395    0.3368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8956    0.8223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0834    0.6771    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5516    1.3078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2605    1.1626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5408    0.3866    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0090   -0.2441    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8031   -0.0989    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2893   -1.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1014   -1.1652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6332   -0.5345    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3529    0.2414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0042    0.7478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6871    0.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4578   -0.5077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9641   -1.1590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9931   -1.2769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5228   -0.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8038   -0.2548    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2818    1.2263    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9172    0.8330    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1921   -0.7923    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2130    0.8083    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 11  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  3 22  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  6 23  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 15  1  0  0  0  0
  9 24  1  1  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 25  1  6  0  0  0
 11 21  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 18  1  0  0  0  0
 14 20  1  1  0  0  0
 15 16  1  0  0  0  0
 15 26  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
M  END

HMDB0000490
     RDKit          3D
Etiocholanolone
 51 54  0  0  0  0  0  0  0  0999 V2000
    2.9843    0.3630   -1.5097 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8609   -0.5246   -0.3095 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1273   -1.7936   -0.5654 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.4387   -0.9808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0078   -0.6234    0.0366 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7747    0.5644    0.5440 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1085    0.9774    1.8632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3227    0.5512    1.9153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9677    0.7568    0.5459 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4361    0.5473    0.7086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1569    0.2986   -0.5816 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5142    0.0868   -0.2541 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5674   -0.8987   -1.2528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2605   -1.3486   -0.6400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3228   -0.1614   -0.4502 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1824    0.6111   -1.7578 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1598    0.1635    0.8507 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1177    1.2396    1.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4863    0.6000    0.9735 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2095   -0.6947    0.2785 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9222   -1.6779    0.2036 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5635    1.3752   -1.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0572    0.4887   -1.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4820   -0.0907   -2.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0381   -2.3361    0.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6260   -2.4075   -1.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1697   -2.4231   -1.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6783   -1.0167   -2.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1806   -1.2862    0.9298 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7004    1.4387   -0.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2271    2.0749    2.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6356    0.4545    2.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4739   -0.4700    2.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8716    1.2234    2.6343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7812    1.8402    0.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8525    1.4372    1.2399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6582   -0.3259    1.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1380    1.1598   -1.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7272    0.4184    0.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4577   -0.7727   -2.3464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2859   -1.7500   -1.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4151   -1.7785    0.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212   -2.0904   -1.3527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1345    0.9216   -1.9292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5669    0.0006   -2.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8064    1.5382   -1.7392 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1460   -0.5750    1.6803 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0174    2.1547    0.5783 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9719    1.5204    2.2594 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0982    1.2126    0.2502 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0163    0.4658    1.9291 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  6
 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  1
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
M  END

AE2
  Mrv1652305271900122D          

 26 29  0  0  0  0            999 V2000
    1.3350   -0.7296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1471   -0.5844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4274    0.1916    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2395    0.3368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8956    0.8223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0834    0.6771    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5516    1.3078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2605    1.1626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5408    0.3866    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0090   -0.2441    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8031   -0.0989    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2893   -1.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1014   -1.1652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6332   -0.5345    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3529    0.2414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0042    0.7478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6871    0.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4578   -0.5077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9641   -1.1590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9931   -1.2769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5228   -0.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8038   -0.2548    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2818    1.2263    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9172    0.8330    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1921   -0.7923    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2130    0.8083    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 11  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  3 22  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  6 23  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 15  1  0  0  0  0
  9 24  1  1  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 25  1  6  0  0  0
 11 21  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 18  1  0  0  0  0
 14 20  1  1  0  0  0
 15 16  1  0  0  0  0
 15 26  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0000565

> <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-BNSUEQOYSA-N

> <FORMULA>
C19H30O2

> <MOLECULAR_WEIGHT>
290.4403

> <EXACT_MASS>
290.224580204

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
34.35919168008975

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,5R,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>
83.8089

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.37e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5R,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

$$$$

HMDB0000490
     RDKit          3D
Etiocholanolone
 51 54  0  0  0  0  0  0  0  0999 V2000
    2.9843    0.3630   -1.5097 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8609   -0.5246   -0.3095 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1273   -1.7936   -0.5654 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.4387   -0.9808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0078   -0.6234    0.0366 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7747    0.5644    0.5440 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1085    0.9774    1.8632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3227    0.5512    1.9153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9677    0.7568    0.5459 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4361    0.5473    0.7086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1569    0.2986   -0.5816 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5142    0.0868   -0.2541 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5674   -0.8987   -1.2528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2605   -1.3486   -0.6400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3228   -0.1614   -0.4502 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1824    0.6111   -1.7578 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1598    0.1635    0.8507 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1177    1.2396    1.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4863    0.6000    0.9735 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2095   -0.6947    0.2785 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9222   -1.6779    0.2036 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5635    1.3752   -1.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0572    0.4887   -1.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4820   -0.0907   -2.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0381   -2.3361    0.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6260   -2.4075   -1.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1697   -2.4231   -1.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6783   -1.0167   -2.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1806   -1.2862    0.9298 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7004    1.4387   -0.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2271    2.0749    2.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6356    0.4545    2.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4739   -0.4700    2.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8716    1.2234    2.6343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7812    1.8402    0.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8525    1.4372    1.2399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6582   -0.3259    1.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1380    1.1598   -1.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7272    0.4184    0.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4577   -0.7727   -2.3464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2859   -1.7500   -1.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4151   -1.7785    0.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212   -2.0904   -1.3527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1345    0.9216   -1.9292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5669    0.0006   -2.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8064    1.5382   -1.7392 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1460   -0.5750    1.6803 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0174    2.1547    0.5783 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9719    1.5204    2.2594 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0982    1.2126    0.2502 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0163    0.4658    1.9291 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  6
 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  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: AE2                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       2.492  -1.362   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.008  -1.091   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.531   0.358   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.047   0.629   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.538   1.535   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.022   1.264   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.030   2.441   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.486   2.170   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.009   0.722   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.017  -0.456   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.499  -0.185   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.540  -1.904   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.056  -2.175   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.049  -0.998   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.525   0.451   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.741   1.396   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.016   0.532   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.588  -0.948   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -5.533  -2.163   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -3.720  -2.384   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.976  -1.633   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0       5.234  -0.476   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       2.393   2.289   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      -1.712   1.555   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.359  -1.479   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.264   1.509   0.000  0.00  0.00           H+0
CONECT    1    2   11                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5   22                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   11   23                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   15   24                                             
CONECT   10    9   11   12   25                                             
CONECT   11    1    6   10   21                                             
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   18   20                                             
CONECT   15    9   14   16   26                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   14   17   19                                                  
CONECT   19   18                                                            
CONECT   20   14                                                            
CONECT   21   11                                                            
CONECT   22    3                                                            
CONECT   23    6                                                            
CONECT   24    9                                                            
CONECT   25   10                                                            
CONECT   26   15                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

COMPND    HMDB0000490
HETATM    1  C1  UNL     1       2.984   0.363  -1.510  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.861  -0.525  -0.310  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.127  -1.794  -0.565  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.714  -1.439  -0.981  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.008  -0.623   0.037  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.775   0.564   0.544  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.108   0.977   1.863  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.323   0.551   1.915  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.968   0.757   0.546  1.00  0.00           C  
HETATM   10  C10 UNL     1      -3.436   0.547   0.709  1.00  0.00           C  
HETATM   11  C11 UNL     1      -4.157   0.299  -0.582  1.00  0.00           C  
HETATM   12  O1  UNL     1      -5.514   0.087  -0.254  1.00  0.00           O  
HETATM   13  C12 UNL     1      -3.567  -0.899  -1.253  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.261  -1.349  -0.640  1.00  0.00           C  
HETATM   15  C14 UNL     1      -1.323  -0.161  -0.450  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.182   0.611  -1.758  1.00  0.00           C  
HETATM   17  C16 UNL     1       2.160   0.164   0.851  1.00  0.00           C  
HETATM   18  C17 UNL     1       3.118   1.240   1.195  1.00  0.00           C  
HETATM   19  C18 UNL     1       4.486   0.600   0.973  1.00  0.00           C  
HETATM   20  C19 UNL     1       4.209  -0.695   0.279  1.00  0.00           C  
HETATM   21  O2  UNL     1       4.922  -1.678   0.204  1.00  0.00           O  
HETATM   22  H1  UNL     1       2.564   1.375  -1.354  1.00  0.00           H  
HETATM   23  H2  UNL     1       4.057   0.489  -1.823  1.00  0.00           H  
HETATM   24  H3  UNL     1       2.482  -0.091  -2.399  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.038  -2.336   0.403  1.00  0.00           H  
HETATM   26  H5  UNL     1       2.626  -2.408  -1.310  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.170  -2.423  -1.056  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.678  -1.017  -2.006  1.00  0.00           H  
HETATM   29  H8  UNL     1      -0.181  -1.286   0.930  1.00  0.00           H  
HETATM   30  H9  UNL     1       0.700   1.439  -0.141  1.00  0.00           H  
HETATM   31  H10 UNL     1       0.227   2.075   2.016  1.00  0.00           H  
HETATM   32  H11 UNL     1       0.636   0.454   2.708  1.00  0.00           H  
HETATM   33  H12 UNL     1      -1.474  -0.470   2.293  1.00  0.00           H  
HETATM   34  H13 UNL     1      -1.872   1.223   2.634  1.00  0.00           H  
HETATM   35  H14 UNL     1      -1.781   1.840   0.293  1.00  0.00           H  
HETATM   36  H15 UNL     1      -3.852   1.437   1.240  1.00  0.00           H  
HETATM   37  H16 UNL     1      -3.658  -0.326   1.378  1.00  0.00           H  
HETATM   38  H17 UNL     1      -4.138   1.160  -1.269  1.00  0.00           H  
HETATM   39  H18 UNL     1      -5.727   0.418   0.641  1.00  0.00           H  
HETATM   40  H19 UNL     1      -3.458  -0.773  -2.346  1.00  0.00           H  
HETATM   41  H20 UNL     1      -4.286  -1.750  -1.099  1.00  0.00           H  
HETATM   42  H21 UNL     1      -2.415  -1.779   0.366  1.00  0.00           H  
HETATM   43  H22 UNL     1      -1.821  -2.090  -1.353  1.00  0.00           H  
HETATM   44  H23 UNL     1      -0.134   0.922  -1.929  1.00  0.00           H  
HETATM   45  H24 UNL     1      -1.567   0.001  -2.587  1.00  0.00           H  
HETATM   46  H25 UNL     1      -1.806   1.538  -1.739  1.00  0.00           H  
HETATM   47  H26 UNL     1       2.146  -0.575   1.680  1.00  0.00           H  
HETATM   48  H27 UNL     1       3.017   2.155   0.578  1.00  0.00           H  
HETATM   49  H28 UNL     1       2.972   1.520   2.259  1.00  0.00           H  
HETATM   50  H29 UNL     1       5.098   1.213   0.250  1.00  0.00           H  
HETATM   51  H30 UNL     1       5.016   0.466   1.929  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

HMDB0000490
     RDKit          3D
Etiocholanolone
 51 54  0  0  0  0  0  0  0  0999 V2000
    2.9843    0.3630   -1.5097 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8609   -0.5246   -0.3095 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1273   -1.7936   -0.5654 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.4387   -0.9808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0078   -0.6234    0.0366 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7747    0.5644    0.5440 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1085    0.9774    1.8632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3227    0.5512    1.9153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9677    0.7568    0.5459 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4361    0.5473    0.7086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1569    0.2986   -0.5816 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5142    0.0868   -0.2541 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5674   -0.8987   -1.2528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2605   -1.3486   -0.6400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3228   -0.1614   -0.4502 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1824    0.6111   -1.7578 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1598    0.1635    0.8507 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1177    1.2396    1.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4863    0.6000    0.9735 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2095   -0.6947    0.2785 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9222   -1.6779    0.2036 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5635    1.3752   -1.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0572    0.4887   -1.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4820   -0.0907   -2.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0381   -2.3361    0.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6260   -2.4075   -1.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1697   -2.4231   -1.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6783   -1.0167   -2.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1806   -1.2862    0.9298 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7004    1.4387   -0.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2271    2.0749    2.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6356    0.4545    2.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4739   -0.4700    2.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8716    1.2234    2.6343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7812    1.8402    0.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8525    1.4372    1.2399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6582   -0.3259    1.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1380    1.1598   -1.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7272    0.4184    0.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4577   -0.7727   -2.3464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2859   -1.7500   -1.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4151   -1.7785    0.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212   -2.0904   -1.3527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1345    0.9216   -1.9292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5669    0.0006   -2.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8064    1.5382   -1.7392 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1460   -0.5750    1.6803 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0174    2.1547    0.5783 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9719    1.5204    2.2594 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0982    1.2126    0.2502 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0163    0.4658    1.9291 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  6
 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  1
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(3alpha,5beta)-3-Hydroxyandrostan-17-one	ChEBI
3alpha-Etiocholanolone	ChEBI
3alpha-Hydroxyetiocholan-17-one	ChEBI
5-Isoandrosterone	ChEBI
5beta-Androstan-3alpha-ol-17-one	ChEBI
5beta-Androsterone	ChEBI
AETIOCHOLANOLONE	ChEBI
Etiocholan-3alpha-ol-17-one	ChEBI
3alpha-Hydroxy-5beta-androstan-17-one	Kegg
(3a,5b)-3-Hydroxyandrostan-17-one	Generator
(3Α,5β)-3-hydroxyandrostan-17-one	Generator
3a-Etiocholanolone	Generator
3Α-etiocholanolone	Generator
3a-Hydroxyetiocholan-17-one	Generator
3Α-hydroxyetiocholan-17-one	Generator
5b-Androstan-3a-ol-17-one	Generator
5Β-androstan-3α-ol-17-one	Generator
5b-Androsterone	Generator
5Β-androsterone	Generator
Etiocholan-3a-ol-17-one	Generator
Etiocholan-3α-ol-17-one	Generator
3a-Hydroxy-5b-androstan-17-one	Generator
3Α-hydroxy-5β-androstan-17-one	Generator
3a-Hydroxy-5b-androstane-17-one	HMDB
5 beta Androsterone	HMDB
5b-Androstane-3a-ol-17-one	HMDB
a-Etiocholanolone	HMDB
alpha-Etiocholanolone	HMDB
3-alpha-Hydroxy-5-beta-androstan-17-one	HMDB
5-beta-Androsterone	HMDB
3 alpha Hydroxy 5 beta androstan 17 one	HMDB

Chemical Formula

C₁₉H₃₀O₂

Average Mass

290.4403 Da

Monoisotopic Mass

290.22458 Da

IUPAC Name

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

CAS Registry Number

53-42-9

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-BNSUEQOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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
Homo sapiens	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Mus musculus	LOTUS Database	35616633
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

Species Where Detected

Species Name	Source	Reference
Apiocrea chrysosperma Ap101	KNApSAcK Database	22123792

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-alpha-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

3alpha-hydroxy steroid (CHEBI:28195 )
17-oxo steroid (CHEBI:28195 )
androstanoid (CHEBI:28195 )
C19 steroids (androgens) and derivatives (C04373 )
Androstane and derivatives (C04373 )
C19 steroids (androgens) and derivatives (LMST02020059 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	152 - 154 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0063 g/L	ALOGPS
logP	3.71	ALOGPS
logP	3.77	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	18.3	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	83.81 m³·mol⁻¹	ChemAxon
Polarizability	34.36 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

HMDB0000490

DrugBank ID

DB02854

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

28195

Good Scents ID

Not Available

References

General References

Kaminski RM, Marini H, Kim WJ, Rogawski MA: Anticonvulsant activity of androsterone and etiocholanolone. Epilepsia. 2005 Jun;46(6):819-27. [PubMed:15946323 ]
Hampl R, Starka L, Jansky L: Steroids and thermogenesis. Physiol Res. 2006;55(2):123-31. Epub 2005 May 24. [PubMed:15910167 ]
Poor V, Juricskay S, Telegdy E: Urinary steroids in men with male-pattern alopecia. J Biochem Biophys Methods. 2002 Oct-Nov;53(1-3):123-30. [PubMed:12406594 ]
George JM, Wolff SM, Diller E, Bartter FC: Recurrent fever of unknown etiology: failure to demonstrate association between fever and plasma unconjugated etiocholanolone. J Clin Invest. 1969 Mar;48(3):558-63. [PubMed:4886315 ]
Kecskes L, Juricskay Z: Steroid spectrum in human urine as revealed by gas chromatography. I. Qualitative analysis of C19--C2102-3 steroids. Acta Biochim Biophys Acad Sci Hung. 1975;10(1-2):37-49. [PubMed:1146492 ]

Showing NP-Card for Etiocholanolone (NP0000565)

MOL for NP0000565 (Etiocholanolone)

3D MOL for NP0000565 (Etiocholanolone)

3D SDF for NP0000565 (Etiocholanolone)

3D-SDF for NP0000565 (Etiocholanolone)

PDB for NP0000565 (Etiocholanolone)

3D PDB for NP0000565 (Etiocholanolone)

SMILES for NP0000565 (Etiocholanolone)

INCHI for NP0000565 (Etiocholanolone)

Structure for NP0000565 (Etiocholanolone)

3D Structure for NP0000565 (Etiocholanolone)