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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-09-22 17:43:43 UTC

HMDB ID

HMDB0000551

Secondary Accession Numbers

HMDB00551

Metabolite Identification

Common Name

Etiocholanediol

Description

Etiocholanediol is one of the compounds tested to allow for the unequivocal identification of the presence of urinary anabolic steroids and metabolites banned for use in sport by athletes. In urine samples collected for anti-doping purposes with moderately elevated testosterone and epitestosterone ratio, or when a suspicion of manipulation of the sample occurs, Etiocholanediol is tested for further clarification. It is worth mentioning that the concentration parameters vary enormously according to the gender of the subjects, ethnic origin, the urine collection period (before or after effort, period of the day) and the hydration state of the athlete. Urinary steroid data using several methodologies are not appropriate for identification purposes and to an extent not unique to individuals. (PMID: 16337352 , 16338181 , 16337352 , 17260133 ).

Structure

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


  Mrv1652305231918042D          

 25 28  0  0  1  0            999 V2000
   10.4450  -10.4854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4450  -11.3104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1595  -11.7229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8739  -11.3104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.8739  -10.4854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1595  -10.0729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5884  -11.7229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3028  -11.3104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3028  -10.4854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.5884  -10.0729    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.0173  -10.0729    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.0173   -9.2479    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.3028   -8.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5884   -9.2479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8020  -10.3278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2869   -9.6604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8020   -8.9930    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.7305  -11.7229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1036   -8.4274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0569   -8.2084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5884  -10.8979    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8739   -9.6604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3028   -9.6604    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.1036  -10.8934    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8937  -12.1549    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
  2 18  1  6  0  0  0
 12 19  1  1  0  0  0
 17 20  1  1  0  0  0
 10 21  1  6  0  0  0
  5 22  1  1  0  0  0
  9 23  1  1  0  0  0
 11 24  1  6  0  0  0
  4 25  1  1  0  0  0
M  END

HMDB0000551
     RDKit          3D
Etiocholanediol
 53 56  0  0  0  0  0  0  0  0999 V2000
    2.7456    0.6524    1.6813 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7758    0.3140    0.2117 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2799    1.4348   -0.6169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8234    1.6608   -0.6256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0212    0.4196   -0.6436 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5337   -0.5901    0.3755 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3410   -1.8108    0.4465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7517   -1.4621    0.7840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9221    0.0599    0.8402 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3749    0.3154    1.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2305    0.3939   -0.1028 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4210   -0.3256    0.1675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6904   -0.0925   -1.3782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2309   -0.0972   -1.5614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4654    0.6781   -0.4794 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9068    2.0938   -0.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8980   -0.9013   -0.0974 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6211   -1.9918    0.5711 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0827   -1.6857    0.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1133   -0.2383   -0.2207 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1762    0.4556    0.3091 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5192   -0.2052    2.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7798    0.9967    1.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0714    1.4885    1.9268 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6755    1.3098   -1.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7778    2.3775   -0.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5909    2.2102   -1.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5500    2.2580    0.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1829   -0.0733   -1.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5930   -0.1499    1.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0581   -2.4232    1.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2378   -2.4759   -0.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4963   -1.9217    0.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0501   -1.8115    1.8166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3342    0.4368    1.6993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4461    1.2508    1.7222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7215   -0.4946    1.8005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5884    1.4607   -0.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1412   -0.0920   -0.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0710   -1.1347   -1.5955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1452    0.5235   -2.2113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8170   -1.1320   -1.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9168    0.4025   -2.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6643    2.2748   -1.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4621    2.4107    0.3664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1334    2.8436   -0.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9203   -1.0192   -1.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3733   -2.9576    0.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4356   -2.1225    1.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4319   -2.3080   -0.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7255   -1.8509    1.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1226   -0.1907   -1.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7237    0.8357   -0.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 17  2  1  0
 20  2  1  0
 15  5  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  6
  6 30  1  1
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  1
 10 36  1  0
 10 37  1  0
 11 38  1  6
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 16 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  6
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  6
 21 53  1  0
M  END


  Mrv1652305231918042D          

 25 28  0  0  1  0            999 V2000
   10.4450  -10.4854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4450  -11.3104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1595  -11.7229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8739  -11.3104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.8739  -10.4854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1595  -10.0729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5884  -11.7229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3028  -11.3104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3028  -10.4854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.5884  -10.0729    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.0173  -10.0729    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.0173   -9.2479    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.3028   -8.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5884   -9.2479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8020  -10.3278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2869   -9.6604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8020   -8.9930    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.7305  -11.7229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1036   -8.4274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0569   -8.2084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5884  -10.8979    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8739   -9.6604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3028   -9.6604    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.1036  -10.8934    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8937  -12.1549    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
  2 18  1  6  0  0  0
 12 19  1  1  0  0  0
 17 20  1  1  0  0  0
 10 21  1  6  0  0  0
  5 22  1  1  0  0  0
  9 23  1  1  0  0  0
 11 24  1  6  0  0  0
  4 25  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0000551

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC[C@H](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/C19H32O2/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/h12-17,20-21H,3-11H2,1-2H3/t12-,13-,14+,15+,16+,17+,18+,19+/m1/s1

> <INCHI_KEY>
CBMYJHIOYJEBSB-GCXXXECGSA-N

> <FORMULA>
C19H32O2

> <MOLECULAR_WEIGHT>
292.4562

> <EXACT_MASS>
292.240230268

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
35.19525567353625

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.56

> <JCHEM_LOGP>
3.2037568309999997

> <ALOGPS_LOGS>
-4.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.377705356554483

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.2963963211217

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7580100340749988

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
84.63119999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.93e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000551
     RDKit          3D
Etiocholanediol
 53 56  0  0  0  0  0  0  0  0999 V2000
    2.7456    0.6524    1.6813 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7758    0.3140    0.2117 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2799    1.4348   -0.6169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8234    1.6608   -0.6256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0212    0.4196   -0.6436 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5337   -0.5901    0.3755 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3410   -1.8108    0.4465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7517   -1.4621    0.7840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9221    0.0599    0.8402 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3749    0.3154    1.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2305    0.3939   -0.1028 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4210   -0.3256    0.1675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6904   -0.0925   -1.3782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2309   -0.0972   -1.5614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4654    0.6781   -0.4794 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9068    2.0938   -0.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8980   -0.9013   -0.0974 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6211   -1.9918    0.5711 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0827   -1.6857    0.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1133   -0.2383   -0.2207 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1762    0.4556    0.3091 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5192   -0.2052    2.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7798    0.9967    1.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0714    1.4885    1.9268 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6755    1.3098   -1.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7778    2.3775   -0.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5909    2.2102   -1.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5500    2.2580    0.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1829   -0.0733   -1.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5930   -0.1499    1.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0581   -2.4232    1.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2378   -2.4759   -0.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4963   -1.9217    0.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0501   -1.8115    1.8166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3342    0.4368    1.6993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4461    1.2508    1.7222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7215   -0.4946    1.8005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5884    1.4607   -0.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1412   -0.0920   -0.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0710   -1.1347   -1.5955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1452    0.5235   -2.2113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8170   -1.1320   -1.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9168    0.4025   -2.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6643    2.2748   -1.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4621    2.4107    0.3664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1334    2.8436   -0.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9203   -1.0192   -1.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3733   -2.9576    0.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4356   -2.1225    1.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4319   -2.3080   -0.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7255   -1.8509    1.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1226   -0.1907   -1.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7237    0.8357   -0.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 17  2  1  0
 20  2  1  0
 15  5  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  6
  6 30  1  1
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  1
 10 36  1  0
 10 37  1  0
 11 38  1  6
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 16 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  6
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  6
 21 53  1  0
M  END

HEADER    PROTEIN                                 23-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-MAY-19         0                                  
HETATM    1  C   UNK     0      19.497 -19.573   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      19.497 -21.113   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.831 -21.883   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      22.165 -21.113   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.165 -19.573   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      20.831 -18.803   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      23.498 -21.883   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.832 -21.113   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      24.832 -19.573   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.498 -18.803   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      26.166 -18.803   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      26.166 -17.263   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      24.832 -16.493   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      23.498 -17.263   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      27.630 -19.279   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.536 -18.033   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      27.630 -16.787   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      18.164 -21.883   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      26.327 -15.731   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      28.106 -15.322   0.000  0.00  0.00           O+0
HETATM   21  H   UNK     0      23.498 -20.343   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0      22.165 -18.033   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0      24.832 -18.033   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      26.327 -20.334   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      22.202 -22.689   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7   25                                             
CONECT    5    4    6   10   22                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   23                                             
CONECT   10    9    5   14   21                                             
CONECT   11    9   12   15   24                                             
CONECT   12   11   13   17   19                                             
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   20                                                  
CONECT   18    2                                                            
CONECT   19   12                                                            
CONECT   20   17                                                            
CONECT   21   10                                                            
CONECT   22    5                                                            
CONECT   23    9                                                            
CONECT   24   11                                                            
CONECT   25    4                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0000551
HETATM    1  C1  UNL     1       2.746   0.652   1.681  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.776   0.314   0.212  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.280   1.435  -0.617  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.823   1.661  -0.626  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.021   0.420  -0.644  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.534  -0.590   0.375  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.341  -1.811   0.447  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.752  -1.462   0.784  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.922   0.060   0.840  1.00  0.00           C  
HETATM   10  C10 UNL     1      -3.375   0.315   1.092  1.00  0.00           C  
HETATM   11  C11 UNL     1      -4.231   0.394  -0.103  1.00  0.00           C  
HETATM   12  O1  UNL     1      -5.421  -0.326   0.167  1.00  0.00           O  
HETATM   13  C12 UNL     1      -3.690  -0.092  -1.378  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.231  -0.097  -1.561  1.00  0.00           C  
HETATM   15  C14 UNL     1      -1.465   0.678  -0.479  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.907   2.094  -0.566  1.00  0.00           C  
HETATM   17  C16 UNL     1       1.898  -0.901  -0.097  1.00  0.00           C  
HETATM   18  C17 UNL     1       2.621  -1.992   0.571  1.00  0.00           C  
HETATM   19  C18 UNL     1       4.083  -1.686   0.249  1.00  0.00           C  
HETATM   20  C19 UNL     1       4.113  -0.238  -0.221  1.00  0.00           C  
HETATM   21  O2  UNL     1       5.176   0.456   0.309  1.00  0.00           O  
HETATM   22  H1  UNL     1       2.519  -0.205   2.325  1.00  0.00           H  
HETATM   23  H2  UNL     1       3.780   0.997   1.958  1.00  0.00           H  
HETATM   24  H3  UNL     1       2.071   1.488   1.927  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.676   1.310  -1.662  1.00  0.00           H  
HETATM   26  H5  UNL     1       2.778   2.378  -0.251  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.591   2.210  -1.587  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.550   2.258   0.268  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.183  -0.073  -1.642  1.00  0.00           H  
HETATM   30  H9  UNL     1       0.593  -0.150   1.386  1.00  0.00           H  
HETATM   31  H10 UNL     1       0.058  -2.423   1.303  1.00  0.00           H  
HETATM   32  H11 UNL     1      -0.238  -2.476  -0.442  1.00  0.00           H  
HETATM   33  H12 UNL     1      -2.496  -1.922   0.106  1.00  0.00           H  
HETATM   34  H13 UNL     1      -2.050  -1.811   1.817  1.00  0.00           H  
HETATM   35  H14 UNL     1      -1.334   0.437   1.699  1.00  0.00           H  
HETATM   36  H15 UNL     1      -3.446   1.251   1.722  1.00  0.00           H  
HETATM   37  H16 UNL     1      -3.722  -0.495   1.800  1.00  0.00           H  
HETATM   38  H17 UNL     1      -4.588   1.461  -0.210  1.00  0.00           H  
HETATM   39  H18 UNL     1      -6.141  -0.092  -0.440  1.00  0.00           H  
HETATM   40  H19 UNL     1      -4.071  -1.135  -1.595  1.00  0.00           H  
HETATM   41  H20 UNL     1      -4.145   0.524  -2.211  1.00  0.00           H  
HETATM   42  H21 UNL     1      -1.817  -1.132  -1.648  1.00  0.00           H  
HETATM   43  H22 UNL     1      -1.917   0.402  -2.526  1.00  0.00           H  
HETATM   44  H23 UNL     1      -2.664   2.275  -1.387  1.00  0.00           H  
HETATM   45  H24 UNL     1      -2.462   2.411   0.366  1.00  0.00           H  
HETATM   46  H25 UNL     1      -1.133   2.844  -0.714  1.00  0.00           H  
HETATM   47  H26 UNL     1       1.920  -1.019  -1.191  1.00  0.00           H  
HETATM   48  H27 UNL     1       2.373  -2.958   0.041  1.00  0.00           H  
HETATM   49  H28 UNL     1       2.436  -2.122   1.633  1.00  0.00           H  
HETATM   50  H29 UNL     1       4.432  -2.308  -0.624  1.00  0.00           H  
HETATM   51  H30 UNL     1       4.725  -1.851   1.137  1.00  0.00           H  
HETATM   52  H31 UNL     1       4.123  -0.191  -1.345  1.00  0.00           H  
HETATM   53  H32 UNL     1       5.724   0.836  -0.447  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   52
CONECT   21   53
END

HMDB0000551
     RDKit          3D
Etiocholanediol
 53 56  0  0  0  0  0  0  0  0999 V2000
    2.7456    0.6524    1.6813 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7758    0.3140    0.2117 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2799    1.4348   -0.6169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8234    1.6608   -0.6256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0212    0.4196   -0.6436 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5337   -0.5901    0.3755 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3410   -1.8108    0.4465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7517   -1.4621    0.7840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9221    0.0599    0.8402 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3749    0.3154    1.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2305    0.3939   -0.1028 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4210   -0.3256    0.1675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6904   -0.0925   -1.3782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2309   -0.0972   -1.5614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4654    0.6781   -0.4794 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9068    2.0938   -0.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8980   -0.9013   -0.0974 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6211   -1.9918    0.5711 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0827   -1.6857    0.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1133   -0.2383   -0.2207 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1762    0.4556    0.3091 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5192   -0.2052    2.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7798    0.9967    1.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0714    1.4885    1.9268 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6755    1.3098   -1.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7778    2.3775   -0.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5909    2.2102   -1.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5500    2.2580    0.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1829   -0.0733   -1.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5930   -0.1499    1.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0581   -2.4232    1.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2378   -2.4759   -0.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4963   -1.9217    0.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0501   -1.8115    1.8166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3342    0.4368    1.6993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4461    1.2508    1.7222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7215   -0.4946    1.8005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5884    1.4607   -0.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1412   -0.0920   -0.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0710   -1.1347   -1.5955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1452    0.5235   -2.2113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8170   -1.1320   -1.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9168    0.4025   -2.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6643    2.2748   -1.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4621    2.4107    0.3664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1334    2.8436   -0.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9203   -1.0192   -1.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3733   -2.9576    0.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4356   -2.1225    1.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4319   -2.3080   -0.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7255   -1.8509    1.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1226   -0.1907   -1.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7237    0.8357   -0.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 17  2  1  0
 20  2  1  0
 15  5  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  6
  6 30  1  1
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  1
 10 36  1  0
 10 37  1  0
 11 38  1  6
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 16 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  6
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  6
 21 53  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3alpha,5beta,17beta)-Androstane-3,17-diol	ChEBI
3alpha,17beta-Dihydroxyetiocholane	ChEBI
(3a,5b,17b)-Androstane-3,17-diol	Generator
(3Α,5β,17β)-androstane-3,17-diol	Generator
3a,17b-Dihydroxyetiocholane	Generator
3Α,17β-dihydroxyetiocholane	Generator
5b-Androstane-3a,17b-diol	HMDB
b-Androstane-3a,17b-diol	HMDB
beta-Androstane-3a,17b-diol	HMDB
5Β-androstane-3α,17β-diol	HMDB

Chemical Formula

C₁₉H₃₂O₂

Average Molecular Weight

292.4562

Monoisotopic Molecular Weight

292.240230268

IUPAC Name

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

Traditional Name

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

CAS Registry Number

1851-23-6

SMILES

[H][C@@]12CC[C@H](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/C19H32O2/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/h12-17,20-21H,3-11H2,1-2H3/t12-,13-,14+,15+,16+,17+,18+,19+/m1/s1

InChI Key

CBMYJHIOYJEBSB-GCXXXECGSA-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
17-hydroxysteroid
3-alpha-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

androstane-3alpha,17beta-diol (CHEBI:36714 )
C19 steroids (androgens) and derivatives (LMST02020077 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 17716701)

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0000551)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0000551)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000551)

Source

Endogenous

Endogenous (HMDB: HMDB0000551)

Animal

Animal (HMDB: HMDB0000551)

Exogenous

Food

Food (HMDB: HMDB0000551)

Animal origin

Poultry

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0000551)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0000551)

Molecular messenger

Hormone (HMDB: HMDB0000551)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000551)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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	0.019 g/L	ALOGPS
logP	3.56	ALOGPS
logP	3.2	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	18.3	ChemAxon
pKa (Strongest Basic)	-0.76	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	84.63 m³·mol⁻¹	ChemAxon
Polarizability	35.2 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	167.996	31661259
DarkChem	[M-H]-	165.684	31661259
AllCCS	[M+H]+	177.234	32859911
AllCCS	[M-H]-	179.136	32859911
DeepCCS	[M-2H]-	208.671	30932474
DeepCCS	[M+Na]+	183.305	30932474
AllCCS	[M+H]+	177.2	32859911
AllCCS	[M+H-H2O]+	174.3	32859911
AllCCS	[M+NH4]+	180.0	32859911
AllCCS	[M+Na]+	180.7	32859911
AllCCS	[M-H]-	179.1	32859911
AllCCS	[M+Na-2H]-	179.4	32859911
AllCCS	[M+HCOO]-	179.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.94 minutes	32390414
Predicted by Siyang on May 30, 2022	14.4283 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.24 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	68.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2466.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	317.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	195.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	175.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	472.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	623.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	599.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	116.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1114.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	449.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1497.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	355.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	415.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	312.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	375.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	43.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Etiocholanediol	[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12C	2433.3	Standard polar	33892256
Etiocholanediol	[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12C	2438.1	Standard non polar	33892256
Etiocholanediol	[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12C	2611.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Etiocholanediol,1TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CC[C@@H]4C[C@H](O)CC[C@]34C)[C@@H]1CC[C@@H]2O[Si](C)(C)C	2563.9	Semi standard non polar	33892256
Etiocholanediol,1TMS,isomer #2	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[C@@H]2O	2552.9	Semi standard non polar	33892256
Etiocholanediol,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[C@@H]2O[Si](C)(C)C	2573.3	Semi standard non polar	33892256
Etiocholanediol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C	2857.1	Semi standard non polar	33892256
Etiocholanediol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@]2(C)[C@H]3CC[C@]4(C)[C@@H](O)CC[C@H]4[C@@H]3CC[C@@H]2C1	2820.7	Semi standard non polar	33892256
Etiocholanediol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1CC[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	3133.6	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.000067 (0.000045-0.00012) uM	Adult (>18 years old)	Male	Normal	17716701	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022111

KNApSAcK ID

Not Available

Chemspider ID

118551

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Etiocholanediol

METLIN ID

5535

PubChem Compound

134494

PDB ID

Not Available

ChEBI ID

36714

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Baulieu, Etienne Emile; Robel, Paul. Androst-5-ene-3b,17b-diol-17a-H3 to testosterone-17a-H3 and 5a- and 5b-androstane-3a,17b-diol-17a-H3 in vivo. Steroids (1963), 2(1), 111-18.

Material Safety Data Sheet (MSDS)

Not Available

General References

Saudan C, Kamber M, Barbati G, Robinson N, Desmarchelier A, Mangin P, Saugy M: Longitudinal profiling of urinary steroids by gas chromatography/combustion/isotope ratio mass spectrometry: diet change may result in carbon isotopic variations. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Feb 2;831(1-2):324-7. Epub 2005 Dec 9. [PubMed:16338181 ]
Robinson N, Castella V, Saudan C, Sottas PE, Schweizer C, Dimo-Simonin N, Mangin P, Saugy M: Elevated and similar urinary testosterone/epitestosterone ratio in all samples of a competition testing: suspicion of a manipulation. Forensic Sci Int. 2006 Nov 10;163(1-2):148-51. Epub 2005 Dec 6. [PubMed:16337352 ]
Thevis M, Geyer H, Mareck U, Sigmund G, Henke J, Henke L, Schanzer W: Detection of manipulation in doping control urine sample collection: a multidisciplinary approach to determine identical urine samples. Anal Bioanal Chem. 2007 Aug;388(7):1539-43. Epub 2007 Jan 27. [PubMed:17260133 ]

Showing metabocard for Etiocholanediol (HMDB0000551)

MOL for HMDB0000551 (Etiocholanediol)

3D MOL for HMDB0000551 (Etiocholanediol)

3D SDF for HMDB0000551 (Etiocholanediol)

3D-SDF for HMDB0000551 (Etiocholanediol)

PDB for HMDB0000551 (Etiocholanediol)

3D PDB for HMDB0000551 (Etiocholanediol)

SMILES for HMDB0000551 (Etiocholanediol)

INCHI for HMDB0000551 (Etiocholanediol)

Structure for HMDB0000551 (Etiocholanediol)

3D Structure for HMDB0000551 (Etiocholanediol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized