Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (22) Show 22 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:02 UTC

HMDB ID

HMDB0000490

Secondary Accession Numbers

HMDB00490

Metabolite 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>
HMDB0000490

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
QGXBDMJGAMFCBF-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 Stereo Labels

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 Molecular Weight

290.4403

Monoisotopic Molecular Weight

290.224580204

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

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 )

Ontology

Physiological effect

Health effect

Schizophrenia (HMDB: HMDB0000490)
Familial mediterranean fever (HMDB: HMDB0000490)

Disposition

Biological location

Cytoplasm (HMDB: HMDB0000490)
Cell membrane (HMDB: HMDB0000490)

Biofluid or Excreta

Blood (HMDB: HMDB0000490)
Urine (HMDB: HMDB0000490)

Tissue substructure

Hepatic tissue (HMDB: HMDB0000490)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 4886315)

Excreta

Biofluid or Excreta

Urine (PMID: 8187312)

Cellular substructure

Membrane (HMDB: HMDB0000490)
Extracellular (HMDB: HMDB0000490)

Organelle

Endoplasmic reticulum (HMDB: HMDB0000490)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000490)

Source

Endogenous

Endogenous (HMDB: HMDB0000490)

Exogenous

Food

Food (HMDB: HMDB0000490)

Animal origin

Poultry

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

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Process

Role

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	168.172	31661259
DarkChem	[M-H]-	164.92	31661259
AllCCS	[M+H]+	175.902	32859911
AllCCS	[M-H]-	178.968	32859911
DeepCCS	[M-2H]-	198.707	30932474
DeepCCS	[M+Na]+	173.525	30932474
AllCCS	[M+H]+	175.9	32859911
AllCCS	[M+H-H2O]+	172.8	32859911
AllCCS	[M+NH4]+	178.8	32859911
AllCCS	[M+Na]+	179.6	32859911
AllCCS	[M-H]-	179.0	32859911
AllCCS	[M+Na-2H]-	179.2	32859911
AllCCS	[M+HCOO]-	179.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Etiocholanolone	[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@]([H])(O)CC[C@]12C	2294.0	Standard polar	33892256
Etiocholanolone	[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@]([H])(O)CC[C@]12C	2445.5	Standard non polar	33892256
Etiocholanolone	[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@]([H])(O)CC[C@]12C	2635.2	Semi standard non polar	33892256

Derivatized

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

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Etiocholanolone EI-B (Non-derivatized)	splash10-052f-1890000000-943a0458e0d4232522f5	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Etiocholanolone EI-B (Non-derivatized)	splash10-052f-1890000000-943a0458e0d4232522f5	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etiocholanolone GC-MS (Non-derivatized) - 70eV, Positive	splash10-03ea-0390000000-17f2f9f14aa5e282a19a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etiocholanolone GC-MS (1 TMS) - 70eV, Positive	splash10-0f7k-1139000000-2bff067a4137502d6ea7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etiocholanolone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etiocholanolone GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etiocholanolone GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etiocholanolone GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Etiocholanolone Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-052e-0090000000-976ebe75980115c6df37	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Etiocholanolone Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-052k-4920000000-cd0699d57cde00089d27	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Etiocholanolone Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-015c-6900000000-4cfdb3def9bc28b9a339	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Etiocholanolone EI-B (HITACHI M-80) , Positive-QTOF	splash10-052f-1890000000-7047f583d11b20a72f9b	2012-08-31	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etiocholanolone 10V, Positive-QTOF	splash10-00dl-0090000000-42eb8c941695a061666d	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etiocholanolone 20V, Positive-QTOF	splash10-00dl-0290000000-1a37c17eb6ea7be9211c	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etiocholanolone 40V, Positive-QTOF	splash10-06u7-2790000000-d6e7cebd4af538181f77	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etiocholanolone 10V, Negative-QTOF	splash10-000i-0090000000-9e9f9de3b33af0311acd	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etiocholanolone 20V, Negative-QTOF	splash10-000i-0090000000-5ba62f51f815ded16002	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etiocholanolone 40V, Negative-QTOF	splash10-0596-2190000000-513ad65531fff88b9f69	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etiocholanolone 10V, Negative-QTOF	splash10-000i-0090000000-c8c452fd99c6bb4f3631	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etiocholanolone 20V, Negative-QTOF	splash10-000i-0090000000-c8c452fd99c6bb4f3631	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etiocholanolone 40V, Negative-QTOF	splash10-000i-0090000000-00c0e7de4e528b98df5c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etiocholanolone 10V, Positive-QTOF	splash10-0006-0090000000-afb176951034ef62419f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etiocholanolone 20V, Positive-QTOF	splash10-052e-0930000000-1ed776267953f7acda8a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etiocholanolone 40V, Positive-QTOF	splash10-0a4j-2900000000-1ba60805778f2942bfd7	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)
Endoplasmic reticulum

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Androstenedione Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0012 +/- 0.00013 uM	Adult (>18 years old)	Male	Normal	4886315	details
Blood	Detected and Quantified	0.0013 +/- 0.00017 uM	Adult (>18 years old)	Both	Normal	4886315	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22944140	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	22944140	details
Urine	Detected and Quantified	0.27 (0.18-0.34) umol/mmol creatinine	Adult (>18 years old)	Male	Normal	11085621	details
Urine	Detected and Quantified	0.21 (0.13-0.28) umol/mmol creatinine	Adult (>18 years old)	Female	Normal	11085621	details
Urine	Detected and Quantified	0.36 (0.11-0.67) umol/mmol creatinine	Adult (>18 years old)	Female	Normal	8187312	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.004 +/- 0.0009 uM	Adult (>18 years old)	Both	Familial Mediterranean Fever	4886315	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Schizophrenia	22944140	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Schizophrenia	22944140	details
Urine	Detected and Quantified	0.59 +/- 0.05 umol/mmol creatinine	Adult (>18 years old)	Female	Hirsutism	8187312	details

Associated Disorders and Diseases

Disease References

Familial mediterranean fever
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 ]
Schizophrenia
Bicikova M, Hill M, Ripova D, Mohr P, Hampl R: Determination of steroid metabolome as a possible tool for laboratory diagnosis of schizophrenia. J Steroid Biochem Mol Biol. 2013 Jan;133:77-83. doi: 10.1016/j.jsbmb.2012.08.009. Epub 2012 Aug 24. [PubMed:22944140 ]
Hirsutism
Gilad S, Chayen R, Tordjman K, Kisch E, Stern N: Assessment of 5 alpha-reductase activity in hirsute women: comparison of serum androstanediol glucuronide with urinary androsterone and aetiocholanolone excretion. Clin Endocrinol (Oxf). 1994 Apr;40(4):459-64. [PubMed:8187312 ]

Associated OMIM IDs

181500 (Schizophrenia)

External Links

DrugBank ID

DB02854

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022072

KNApSAcK ID

Not Available

Chemspider ID

5669

KEGG Compound ID

C04373

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

28195

Food Biomarker Ontology

Not Available

VMH ID

AHANDROSTAN

MarkerDB ID

MDB00000174

Good Scents ID

Not Available

References

Synthesis Reference

Pelli, Beatrice; Traldi, Pietro; Gargano, Michele; Ravasio, Nicoletta; Rossi, Michele. Easy determination of epimeric androsterones by collision spectroscopy: the molar ratio of 5b-androstan-3a-ol-17-one and 5b-androstan-3b-ol-17-one obtained by hydrogenation of 5b-androstane-3,17-dione on copper/alumina. Organic Mass Spectrometry (1987), 22(3), 183-5.

Material Safety Data Sheet (MSDS)

Download (PDF)

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 ]

Only showing the first 10 proteins. There are 22 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Aldo-keto reductase family 1 member C4

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the transformation of the potent androgen dihydrotestosterone (DHT) into the less active form, 5-alpha-androstan-3-alpha,17-beta-diol (3-alpha-diol). Also has some 20-alpha-hydroxysteroid dehydrogenase activity. The biotransformation of the pesticide chlordecone (kepone) to its corresponding alcohol leads to increased biliary excretion of the pesticide and concomitant reduction of its neurotoxicity since bile is the major excretory route.
Gene Name:: AKR1C4
Uniprot ID:: P17516
Molecular weight:: 37094.57

Reactions

Etiocholanolone + NAD → Etiocholanedione + NADH + Hydrogen Ion	details
Etiocholanolone + NADP → Etiocholanedione + NADPH + Hydrogen Ion	details

Enzyme Details

2. UDP-glucuronosyltransferase 2B28

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.
Gene Name:: UGT2B28
Uniprot ID:: Q9BY64
Molecular weight:: 38742.9

Reactions

Etiocholanolone + Uridine diphosphate glucuronic acid → Etiocholanolone glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

3. UDP-glucuronosyltransferase 2B4

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
Gene Name:: UGT2B4
Uniprot ID:: P06133
Molecular weight:: 60512.035

Reactions

Etiocholanolone + Uridine diphosphate glucuronic acid → Etiocholanolone glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

4. UDP-glucuronosyltransferase 1-4

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
Gene Name:: UGT1A4
Uniprot ID:: P22310
Molecular weight:: 60024.535

Reactions

Etiocholanolone + Uridine diphosphate glucuronic acid → Etiocholanolone glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

5. UDP-glucuronosyltransferase 2B10

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:: UGT2B10
Uniprot ID:: P36537
Molecular weight:: 60773.485

Reactions

Etiocholanolone + Uridine diphosphate glucuronic acid → Etiocholanolone glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

6. UDP-glucuronosyltransferase 2B7

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:: UGT2B7
Uniprot ID:: P16662
Molecular weight:: 60720.15

Reactions

Etiocholanolone + Uridine diphosphate glucuronic acid → Etiocholanolone glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

7. UDP-glucuronosyltransferase 2B15

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xenobiotic substrates, including simple phenolic compounds, 7-hydroxylated coumarins, flavonoids, anthraquinones, and certain drugs and their hydroxylated metabolites. It also catalyzes the glucuronidation of endogenous estrogens and androgens.
Gene Name:: UGT2B15
Uniprot ID:: P54855
Molecular weight:: 61035.815

Reactions

Etiocholanolone + Uridine diphosphate glucuronic acid → Etiocholanolone glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

8. UDP-glucuronosyltransferase 2A1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Active on odorants and seems to be involved in olfaction; it could help clear lipophilic odorant molecules from the sensory epithelium.
Gene Name:: UGT2A1
Uniprot ID:: Q9Y4X1
Molecular weight:: 60771.605

Reactions

Etiocholanolone + Uridine diphosphate glucuronic acid → Etiocholanolone glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

9. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Etiocholanolone + Uridine diphosphate glucuronic acid → Etiocholanolone glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

10. UDP-glucuronosyltransferase 1-9

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:: UGT1A9
Uniprot ID:: O60656
Molecular weight:: 59940.495

Reactions

Etiocholanolone + Uridine diphosphate glucuronic acid → Etiocholanolone glucuronide + Uridine 5'-diphosphate	details

Only showing the first 10 proteins. There are 22 proteins in total.

Show all enzymes and transporters

Showing metabocard for Etiocholanolone (HMDB0000490)

MOL for HMDB0000490 (Etiocholanolone)

3D MOL for HMDB0000490 (Etiocholanolone)

3D SDF for HMDB0000490 (Etiocholanolone)

3D-SDF for HMDB0000490 (Etiocholanolone)

PDB for HMDB0000490 (Etiocholanolone)

3D PDB for HMDB0000490 (Etiocholanolone)

SMILES for HMDB0000490 (Etiocholanolone)

INCHI for HMDB0000490 (Etiocholanolone)

Structure for HMDB0000490 (Etiocholanolone)

3D Structure for HMDB0000490 (Etiocholanolone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions