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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-13 04:33:58 UTC

Update Date

2022-03-07 02:49:19 UTC

HMDB ID

HMDB0003769

Secondary Accession Numbers

HMDB03769

Metabolite Identification

Common Name

Etiocholanedione

Description

Etiocholanedione is a 5-beta metabolite product of the catabolism of androgens. Etiocholanedione has been identified as a ketosteroid and isolated from the urine of healthy and diseased persons. Etiocholanedione has been identified as a metabolite of an altered androgen metabolism that eventually leads hepatocellular carcinoma to impaired hormone responsiveness in human. Etiocholanedione has been identified as a metabolite of 17alpha-hydroxyprogesterone in some patients affected by congenital adrenal hyperplasia, although it doesn't appear to account for the masculinization observed in congenital hyperplasia. Etiocholanedione can be the product of microbial contamination of urine since a few organisms are able to synthesize it using endogenous steroids as substrates. Human axillary bacteria are able to produce small amounts of etiocholanedione from testosterone. (PMID: 12161001 , 13795320 , 11161304 , 2026727 ). Etiocholanedione has been found to be a metabolite of Corynebacterium (PMID: 11161304 ).

Structure

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


  Mrv0541 02231219472D          

 25 28  0  0  1  0            999 V2000
   27.2404  -13.2832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0478  -16.4083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1206  -14.4213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2937  -13.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1143  -15.2462    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.2937  -14.0032    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.8649  -14.8281    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.5794  -15.2405    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   26.2937  -14.8281    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   24.1077  -16.1054    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.5794  -13.5908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8649  -14.0032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5926  -16.0996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8518  -16.5350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0742  -15.0795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3498  -14.7809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5557  -14.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3361  -16.5589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5678  -15.2164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0742  -13.7518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5609  -16.1113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4591  -14.4755    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   26.0632  -15.7464    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   26.6340  -15.5068    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.1102  -16.7653    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  2  0  0  0  0
  2 21  2  0  0  0  0
  5  3  1  1  0  0  0
  6  4  1  1  0  0  0
  5  7  1  0  0  0  0
  5 10  1  0  0  0  0
  5 16  1  0  0  0  0
  6  9  1  0  0  0  0
  6 11  1  0  0  0  0
  6 20  1  0  0  0  0
  7  8  1  0  0  0  0
  7 12  1  0  0  0  0
  7 22  1  6  0  0  0
  8  9  1  0  0  0  0
  8 13  1  0  0  0  0
  8 23  1  1  0  0  0
  9 15  1  0  0  0  0
  9 24  1  6  0  0  0
 10 14  1  0  0  0  0
 10 18  1  0  0  0  0
 10 25  1  1  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 15 17  1  0  0  0  0
 16 19  1  0  0  0  0
 17 20  1  0  0  0  0
 18 21  1  0  0  0  0
 19 21  1  0  0  0  0
M  END

HMDB0003769
     RDKit          3D
Etiocholanedione
 49 52  0  0  0  0  0  0  0  0999 V2000
    2.8168   -1.5028   -0.3146 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7243   -0.1326    0.3101 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1395   -0.2148    1.6686 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6961   -0.6067    1.5811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1073    0.2709    0.6622 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5545    0.1970   -0.7205 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3202    0.8318   -1.7677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6652    0.1641   -1.7748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8346   -0.8296   -0.6538 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2626   -1.3149   -0.6463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1920   -0.2373   -0.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3248   -0.2586   -0.7023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8351    0.8843    0.6425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3804    1.1342    0.7564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5353   -0.1293    0.6372 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9251   -0.9945    1.8425 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8881    0.8113   -0.5680 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7259    0.9427   -1.7678 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1387    1.0252   -1.1861 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0330    0.5101    0.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8845    0.6265    1.0434 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9671   -2.1629   -0.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9648   -1.4785   -1.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7280   -1.9884    0.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6627   -1.0580    2.2104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3025    0.6745    2.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2457   -0.4779    2.6069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5703   -1.6873    1.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0143    1.3216    1.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6723   -0.8742   -0.9589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3682    1.9305   -1.6588 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1521    0.6340   -2.7492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4546    0.9341   -1.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8917   -0.3607   -2.7220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1745   -1.7136   -0.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5131   -1.6177   -1.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3779   -2.2290   -0.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3620    0.7458    1.6154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3068    1.8066    0.1928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1822    1.5127    1.8027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0094    1.9428    0.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0387   -1.1429    1.7435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3879   -1.9399    1.8685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7887   -0.3560    2.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8284    1.7789   -0.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5461    1.9340   -2.2618 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6276    0.1853   -2.5377 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8455    0.4411   -1.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5095    2.0682   -1.1603 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  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 17  2  1  0
 20  2  1  0
 15  5  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  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
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  1
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
M  END


  Mrv0541 02231219472D          

 25 28  0  0  1  0            999 V2000
   27.2404  -13.2832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0478  -16.4083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1206  -14.4213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2937  -13.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1143  -15.2462    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.2937  -14.0032    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.8649  -14.8281    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.5794  -15.2405    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   26.2937  -14.8281    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   24.1077  -16.1054    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.5794  -13.5908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8649  -14.0032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5926  -16.0996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8518  -16.5350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0742  -15.0795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3498  -14.7809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5557  -14.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3361  -16.5589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5678  -15.2164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0742  -13.7518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5609  -16.1113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4591  -14.4755    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   26.0632  -15.7464    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   26.6340  -15.5068    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.1102  -16.7653    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  2  0  0  0  0
  2 21  2  0  0  0  0
  5  3  1  1  0  0  0
  6  4  1  1  0  0  0
  5  7  1  0  0  0  0
  5 10  1  0  0  0  0
  5 16  1  0  0  0  0
  6  9  1  0  0  0  0
  6 11  1  0  0  0  0
  6 20  1  0  0  0  0
  7  8  1  0  0  0  0
  7 12  1  0  0  0  0
  7 22  1  6  0  0  0
  8  9  1  0  0  0  0
  8 13  1  0  0  0  0
  8 23  1  1  0  0  0
  9 15  1  0  0  0  0
  9 24  1  6  0  0  0
 10 14  1  0  0  0  0
 10 18  1  0  0  0  0
 10 25  1  1  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 15 17  1  0  0  0  0
 16 19  1  0  0  0  0
 17 20  1  0  0  0  0
 18 21  1  0  0  0  0
 19 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003769

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H28O2/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/h12,14-16H,3-11H2,1-2H3/t12-,14+,15+,16+,18+,19+/m1/s1

> <INCHI_KEY>
RAJWOBJTTGJROA-QJISAEMRSA-N

> <FORMULA>
C19H28O2

> <MOLECULAR_WEIGHT>
288.4244

> <EXACT_MASS>
288.20893014

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
33.791660141159525

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,7R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-dione

> <ALOGPS_LOGP>
3.40

> <JCHEM_LOGP>
3.9747853383333336

> <ALOGPS_LOGS>
-4.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.776207883092308

> <JCHEM_PKA_STRONGEST_BASIC>
-7.108868634299542

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
82.78079999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.39e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-β-androstane-3,17-dione

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0003769
     RDKit          3D
Etiocholanedione
 49 52  0  0  0  0  0  0  0  0999 V2000
    2.8168   -1.5028   -0.3146 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7243   -0.1326    0.3101 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1395   -0.2148    1.6686 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6961   -0.6067    1.5811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1073    0.2709    0.6622 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5545    0.1970   -0.7205 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3202    0.8318   -1.7677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6652    0.1641   -1.7748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8346   -0.8296   -0.6538 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2626   -1.3149   -0.6463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1920   -0.2373   -0.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3248   -0.2586   -0.7023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8351    0.8843    0.6425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3804    1.1342    0.7564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5353   -0.1293    0.6372 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9251   -0.9945    1.8425 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8881    0.8113   -0.5680 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7259    0.9427   -1.7678 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1387    1.0252   -1.1861 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0330    0.5101    0.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8845    0.6265    1.0434 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9671   -2.1629   -0.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9648   -1.4785   -1.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7280   -1.9884    0.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6627   -1.0580    2.2104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3025    0.6745    2.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2457   -0.4779    2.6069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5703   -1.6873    1.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0143    1.3216    1.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6723   -0.8742   -0.9589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3682    1.9305   -1.6588 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1521    0.6340   -2.7492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4546    0.9341   -1.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8917   -0.3607   -2.7220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1745   -1.7136   -0.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5131   -1.6177   -1.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3779   -2.2290   -0.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3620    0.7458    1.6154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3068    1.8066    0.1928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1822    1.5127    1.8027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0094    1.9428    0.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0387   -1.1429    1.7435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3879   -1.9399    1.8685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7887   -0.3560    2.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8284    1.7789   -0.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5461    1.9340   -2.2618 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6276    0.1853   -2.5377 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8455    0.4411   -1.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5095    2.0682   -1.1603 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  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 17  2  1  0
 20  2  1  0
 15  5  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  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
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  1
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      50.849 -24.795   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      41.156 -30.629   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      45.025 -26.920   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      49.082 -24.599   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      45.013 -28.460   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      49.082 -26.139   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      46.414 -27.679   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      47.748 -28.449   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      49.082 -27.679   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      45.001 -30.063   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      47.748 -25.369   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      46.414 -26.139   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      47.773 -30.053   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      46.390 -30.865   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      50.539 -28.148   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      43.586 -27.591   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      51.437 -26.909   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      43.561 -30.910   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      42.127 -28.404   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      50.539 -25.670   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      42.114 -30.074   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0      47.524 -27.021   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0      48.651 -29.393   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      49.717 -28.946   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      45.006 -31.295   0.000  0.00  0.00           H+0
CONECT    1   20                                                            
CONECT    2   21                                                            
CONECT    3    5                                                            
CONECT    4    6                                                            
CONECT    5    3    7   10   16                                             
CONECT    6    4    9   11   20                                             
CONECT    7    5    8   12   22                                             
CONECT    8    7    9   13   23                                             
CONECT    9    6    8   15   24                                             
CONECT   10    5   14   18   25                                             
CONECT   11    6   12                                                       
CONECT   12    7   11                                                       
CONECT   13    8   14                                                       
CONECT   14   10   13                                                       
CONECT   15    9   17                                                       
CONECT   16    5   19                                                       
CONECT   17   15   20                                                       
CONECT   18   10   21                                                       
CONECT   19   16   21                                                       
CONECT   20    1    6   17                                                  
CONECT   21    2   18   19                                                  
CONECT   22    7                                                            
CONECT   23    8                                                            
CONECT   24    9                                                            
CONECT   25   10                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0003769
HETATM    1  C1  UNL     1       2.817  -1.503  -0.315  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.724  -0.133   0.310  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.140  -0.215   1.669  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.696  -0.607   1.581  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.107   0.271   0.662  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.555   0.197  -0.720  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.320   0.832  -1.768  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.665   0.164  -1.775  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.835  -0.830  -0.654  1.00  0.00           C  
HETATM   10  C10 UNL     1      -3.263  -1.315  -0.646  1.00  0.00           C  
HETATM   11  C11 UNL     1      -4.192  -0.237  -0.260  1.00  0.00           C  
HETATM   12  O1  UNL     1      -5.325  -0.259  -0.702  1.00  0.00           O  
HETATM   13  C12 UNL     1      -3.835   0.884   0.642  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.380   1.134   0.756  1.00  0.00           C  
HETATM   15  C14 UNL     1      -1.535  -0.129   0.637  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.925  -0.995   1.843  1.00  0.00           C  
HETATM   17  C16 UNL     1       1.888   0.811  -0.568  1.00  0.00           C  
HETATM   18  C17 UNL     1       2.726   0.943  -1.768  1.00  0.00           C  
HETATM   19  C18 UNL     1       4.139   1.025  -1.186  1.00  0.00           C  
HETATM   20  C19 UNL     1       4.033   0.510   0.207  1.00  0.00           C  
HETATM   21  O2  UNL     1       4.884   0.626   1.043  1.00  0.00           O  
HETATM   22  H1  UNL     1       1.967  -2.163  -0.051  1.00  0.00           H  
HETATM   23  H2  UNL     1       2.965  -1.479  -1.406  1.00  0.00           H  
HETATM   24  H3  UNL     1       3.728  -1.988   0.110  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.663  -1.058   2.210  1.00  0.00           H  
HETATM   26  H5  UNL     1       2.303   0.674   2.297  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.246  -0.478   2.607  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.570  -1.687   1.356  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.014   1.322   1.045  1.00  0.00           H  
HETATM   30  H9  UNL     1       0.672  -0.874  -0.959  1.00  0.00           H  
HETATM   31  H10 UNL     1      -0.368   1.931  -1.659  1.00  0.00           H  
HETATM   32  H11 UNL     1       0.152   0.634  -2.749  1.00  0.00           H  
HETATM   33  H12 UNL     1      -2.455   0.934  -1.649  1.00  0.00           H  
HETATM   34  H13 UNL     1      -1.892  -0.361  -2.722  1.00  0.00           H  
HETATM   35  H14 UNL     1      -1.175  -1.714  -0.749  1.00  0.00           H  
HETATM   36  H15 UNL     1      -3.513  -1.618  -1.686  1.00  0.00           H  
HETATM   37  H16 UNL     1      -3.378  -2.229  -0.018  1.00  0.00           H  
HETATM   38  H17 UNL     1      -4.362   0.746   1.615  1.00  0.00           H  
HETATM   39  H18 UNL     1      -4.307   1.807   0.193  1.00  0.00           H  
HETATM   40  H19 UNL     1      -2.182   1.513   1.803  1.00  0.00           H  
HETATM   41  H20 UNL     1      -2.009   1.943   0.092  1.00  0.00           H  
HETATM   42  H21 UNL     1      -3.039  -1.143   1.743  1.00  0.00           H  
HETATM   43  H22 UNL     1      -1.388  -1.940   1.869  1.00  0.00           H  
HETATM   44  H23 UNL     1      -1.789  -0.356   2.740  1.00  0.00           H  
HETATM   45  H24 UNL     1       1.828   1.779  -0.035  1.00  0.00           H  
HETATM   46  H25 UNL     1       2.546   1.934  -2.262  1.00  0.00           H  
HETATM   47  H26 UNL     1       2.628   0.185  -2.538  1.00  0.00           H  
HETATM   48  H27 UNL     1       4.845   0.441  -1.778  1.00  0.00           H  
HETATM   49  H28 UNL     1       4.510   2.068  -1.160  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   12   13
CONECT   13   14   38   39
CONECT   14   15   40   41
CONECT   15   16
CONECT   16   42   43   44
CONECT   17   18   45
CONECT   18   19   46   47
CONECT   19   20   48   49
CONECT   20   21   21
END

HMDB0003769
     RDKit          3D
Etiocholanedione
 49 52  0  0  0  0  0  0  0  0999 V2000
    2.8168   -1.5028   -0.3146 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7243   -0.1326    0.3101 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1395   -0.2148    1.6686 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6961   -0.6067    1.5811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1073    0.2709    0.6622 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5545    0.1970   -0.7205 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3202    0.8318   -1.7677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6652    0.1641   -1.7748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8346   -0.8296   -0.6538 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2626   -1.3149   -0.6463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1920   -0.2373   -0.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3248   -0.2586   -0.7023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8351    0.8843    0.6425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3804    1.1342    0.7564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5353   -0.1293    0.6372 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9251   -0.9945    1.8425 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8881    0.8113   -0.5680 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7259    0.9427   -1.7678 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1387    1.0252   -1.1861 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0330    0.5101    0.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8845    0.6265    1.0434 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9671   -2.1629   -0.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9648   -1.4785   -1.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7280   -1.9884    0.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6627   -1.0580    2.2104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3025    0.6745    2.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2457   -0.4779    2.6069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5703   -1.6873    1.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0143    1.3216    1.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6723   -0.8742   -0.9589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3682    1.9305   -1.6588 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1521    0.6340   -2.7492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4546    0.9341   -1.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8917   -0.3607   -2.7220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1745   -1.7136   -0.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5131   -1.6177   -1.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3779   -2.2290   -0.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3620    0.7458    1.6154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3068    1.8066    0.1928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1822    1.5127    1.8027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0094    1.9428    0.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0387   -1.1429    1.7435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3879   -1.9399    1.8685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7887   -0.3560    2.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8284    1.7789   -0.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5461    1.9340   -2.2618 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6276    0.1853   -2.5377 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8455    0.4411   -1.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5095    2.0682   -1.1603 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  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 17  2  1  0
 20  2  1  0
 15  5  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  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
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  1
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Etiocholane-3,17-dione	ChEBI
Etiocholanedione	ChEBI
(5b)-Androstane-3,17-dione	HMDB
5b-Androstane-3,17-dione	HMDB
5b-Androstanedione	HMDB
5beta-Androstane-3,17-dione	HMDB
Etiochola-3,17-dione	HMDB

Chemical Formula

C₁₉H₂₈O₂

Average Molecular Weight

288.4244

Monoisotopic Molecular Weight

288.20893014

IUPAC Name

(1S,2S,7R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-dione

Traditional Name

5-β-androstane-3,17-dione

CAS Registry Number

1229-12-5

SMILES

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

InChI Identifier

InChI=1S/C19H28O2/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/h12,14-16H,3-11H2,1-2H3/t12-,14+,15+,16+,18+,19+/m1/s1

InChI Key

RAJWOBJTTGJROA-QJISAEMRSA-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-oxo-5-beta-steroid
Oxosteroid
17-oxosteroid
3-oxosteroid
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

androstane-3,17-dione (CHEBI:16985 )
C19 steroids (androgens) and derivatives (C03772 )
Androstane and derivatives (C03772 )
C19 steroids (androgens) and derivatives (LMST02020058 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0003769)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0003769)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0003769)

Source

Exogenous

Exogenous (HMDB: HMDB0003769)

Food

Food (HMDB: HMDB0003769)

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)

Endogenous

Endogenous (HMDB: HMDB0003769)

Microbe

Microbe (HMDB: HMDB0003769)
Corynebacterium jekeium (HMDB: HMDB0003769)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0003769)

Molecular messenger

Hormone (HMDB: HMDB0003769)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0003769)

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0003769)

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	3.64	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0074 g/L	ALOGPS
logP	3.4	ALOGPS
logP	3.97	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	19.78	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	82.78 m³·mol⁻¹	ChemAxon
Polarizability	33.79 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]+	169.307	31661259
DarkChem	[M-H]-	165.597	31661259
DeepCCS	[M-2H]-	204.297	30932474
DeepCCS	[M+Na]+	179.406	30932474
AllCCS	[M+H]+	174.0	32859911
AllCCS	[M+H-H2O]+	170.8	32859911
AllCCS	[M+NH4]+	176.9	32859911
AllCCS	[M+Na]+	177.7	32859911
AllCCS	[M-H]-	178.8	32859911
AllCCS	[M+Na-2H]-	178.9	32859911
AllCCS	[M+HCOO]-	179.2	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.	7.2 minutes	32390414
Predicted by Siyang on May 30, 2022	17.8755 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.67 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2624.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	527.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	224.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	232.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	527.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	671.5 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	762.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	89.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1445.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	468.5 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	1513.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	415.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	446.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	322.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	476.0 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	15.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Etiocholanedione	[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])CC(=O)CC[C@]12C	2613.0	Standard polar	33892256
Etiocholanedione	[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])CC(=O)CC[C@]12C	2432.3	Standard non polar	33892256
Etiocholanedione	[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])CC(=O)CC[C@]12C	2629.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Etiocholanedione,1TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CC[C@@H]4CC(=O)CC[C@]34C)[C@@H]1CC=C2O[Si](C)(C)C	2620.6	Semi standard non polar	33892256
Etiocholanedione,1TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CC[C@@H]4CC(=O)CC[C@]34C)[C@@H]1CC=C2O[Si](C)(C)C	2459.1	Standard non polar	33892256
Etiocholanedione,1TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CC[C@@H]4CC(=O)CC[C@]34C)[C@@H]1CC=C2O[Si](C)(C)C	2889.7	Standard polar	33892256
Etiocholanedione,1TMS,isomer #2	C[C@]12CC[C@H]3[C@@H](CC[C@@H]4CC(O[Si](C)(C)C)=CC[C@]34C)[C@@H]1CCC2=O	2604.5	Semi standard non polar	33892256
Etiocholanedione,1TMS,isomer #2	C[C@]12CC[C@H]3[C@@H](CC[C@@H]4CC(O[Si](C)(C)C)=CC[C@]34C)[C@@H]1CCC2=O	2496.8	Standard non polar	33892256
Etiocholanedione,1TMS,isomer #2	C[C@]12CC[C@H]3[C@@H](CC[C@@H]4CC(O[Si](C)(C)C)=CC[C@]34C)[C@@H]1CCC2=O	2991.4	Standard polar	33892256
Etiocholanedione,1TMS,isomer #3	C[C@]12CC[C@H]3[C@@H](CC[C@@H]4C=C(O[Si](C)(C)C)CC[C@]34C)[C@@H]1CCC2=O	2583.4	Semi standard non polar	33892256
Etiocholanedione,1TMS,isomer #3	C[C@]12CC[C@H]3[C@@H](CC[C@@H]4C=C(O[Si](C)(C)C)CC[C@]34C)[C@@H]1CCC2=O	2503.5	Standard non polar	33892256
Etiocholanedione,1TMS,isomer #3	C[C@]12CC[C@H]3[C@@H](CC[C@@H]4C=C(O[Si](C)(C)C)CC[C@]34C)[C@@H]1CCC2=O	2988.7	Standard polar	33892256
Etiocholanedione,2TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CC[C@@H]4CC(O[Si](C)(C)C)=CC[C@]34C)[C@@H]1CC=C2O[Si](C)(C)C	2648.3	Semi standard non polar	33892256
Etiocholanedione,2TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CC[C@@H]4CC(O[Si](C)(C)C)=CC[C@]34C)[C@@H]1CC=C2O[Si](C)(C)C	2546.7	Standard non polar	33892256
Etiocholanedione,2TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CC[C@@H]4CC(O[Si](C)(C)C)=CC[C@]34C)[C@@H]1CC=C2O[Si](C)(C)C	2957.8	Standard polar	33892256
Etiocholanedione,2TMS,isomer #2	C[C@]12CC[C@H]3[C@@H](CC[C@@H]4C=C(O[Si](C)(C)C)CC[C@]34C)[C@@H]1CC=C2O[Si](C)(C)C	2656.3	Semi standard non polar	33892256
Etiocholanedione,2TMS,isomer #2	C[C@]12CC[C@H]3[C@@H](CC[C@@H]4C=C(O[Si](C)(C)C)CC[C@]34C)[C@@H]1CC=C2O[Si](C)(C)C	2569.7	Standard non polar	33892256
Etiocholanedione,2TMS,isomer #2	C[C@]12CC[C@H]3[C@@H](CC[C@@H]4C=C(O[Si](C)(C)C)CC[C@]34C)[C@@H]1CC=C2O[Si](C)(C)C	2956.9	Standard polar	33892256
Etiocholanedione,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C	2859.5	Semi standard non polar	33892256
Etiocholanedione,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C	2604.0	Standard non polar	33892256
Etiocholanedione,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C	3050.2	Standard polar	33892256
Etiocholanedione,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC[C@]2(C)[C@H]3CC[C@]4(C)C(=O)CC[C@H]4[C@@H]3CC[C@@H]2C1	2839.6	Semi standard non polar	33892256
Etiocholanedione,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC[C@]2(C)[C@H]3CC[C@]4(C)C(=O)CC[C@H]4[C@@H]3CC[C@@H]2C1	2711.8	Standard non polar	33892256
Etiocholanedione,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC[C@]2(C)[C@H]3CC[C@]4(C)C(=O)CC[C@H]4[C@@H]3CC[C@@H]2C1	3150.9	Standard polar	33892256
Etiocholanedione,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=C[C@H]2CC[C@H]3[C@@H]4CCC(=O)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC1	2804.1	Semi standard non polar	33892256
Etiocholanedione,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=C[C@H]2CC[C@H]3[C@@H]4CCC(=O)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC1	2728.5	Standard non polar	33892256
Etiocholanedione,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=C[C@H]2CC[C@H]3[C@@H]4CCC(=O)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC1	3149.1	Standard polar	33892256
Etiocholanedione,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@]2(C)[C@H]3CC[C@]4(C)C(O[Si](C)(C)C(C)(C)C)=CC[C@H]4[C@@H]3CC[C@@H]2C1	3174.0	Semi standard non polar	33892256
Etiocholanedione,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@]2(C)[C@H]3CC[C@]4(C)C(O[Si](C)(C)C(C)(C)C)=CC[C@H]4[C@@H]3CC[C@@H]2C1	2806.4	Standard non polar	33892256
Etiocholanedione,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@]2(C)[C@H]3CC[C@]4(C)C(O[Si](C)(C)C(C)(C)C)=CC[C@H]4[C@@H]3CC[C@@H]2C1	3199.0	Standard polar	33892256
Etiocholanedione,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=C[C@H]2CC[C@H]3[C@@H]4CC=C(O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC1	3171.0	Semi standard non polar	33892256
Etiocholanedione,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=C[C@H]2CC[C@H]3[C@@H]4CC=C(O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC1	2825.3	Standard non polar	33892256
Etiocholanedione,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=C[C@H]2CC[C@H]3[C@@H]4CC=C(O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC1	3199.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Etiocholanedione EI-B (Non-derivatized)	splash10-0079-2960000000-ea444704310ecd83d3ce	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Etiocholanedione GC-EI-TOF (Non-derivatized)	splash10-052f-3921000000-17fcd3fbf7ce3dec6b0b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Etiocholanedione EI-B (Non-derivatized)	splash10-0079-2960000000-ea444704310ecd83d3ce	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Etiocholanedione GC-EI-TOF (Non-derivatized)	splash10-052f-3921000000-17fcd3fbf7ce3dec6b0b	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etiocholanedione GC-MS (Non-derivatized) - 70eV, Positive	splash10-03ea-0490000000-e4819053bc47c4809a6c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etiocholanedione GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etiocholanedione 10V, Positive-QTOF	splash10-000i-0190000000-274e4abb4afd97e047bd	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etiocholanedione 20V, Positive-QTOF	splash10-05a9-0490000000-ea747ee7d3b074178ffe	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etiocholanedione 40V, Positive-QTOF	splash10-0h04-2790000000-f49dc8e9045f408d3658	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etiocholanedione 10V, Negative-QTOF	splash10-000i-0090000000-66fb88cf829fcdb74c4c	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etiocholanedione 20V, Negative-QTOF	splash10-000i-0090000000-dcc70e0ff918620e20dc	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etiocholanedione 40V, Negative-QTOF	splash10-052f-3190000000-eb4a160989f10eb86d96	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etiocholanedione 10V, Negative-QTOF	splash10-000i-0090000000-383f8ad782110ec64fbf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etiocholanedione 20V, Negative-QTOF	splash10-000i-0090000000-383f8ad782110ec64fbf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etiocholanedione 40V, Negative-QTOF	splash10-0f79-0090000000-0497207bd4a67a50d8d8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etiocholanedione 10V, Positive-QTOF	splash10-000i-0090000000-a3a5ee5e1cdb4d550aac	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etiocholanedione 20V, Positive-QTOF	splash10-0h90-0970000000-66d8653b98d2df4aa327	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etiocholanedione 40V, Positive-QTOF	splash10-0a4i-1900000000-2a46c86775b66edae018	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Androstenedione Metabolism		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB07375

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023225

KNApSAcK ID

Not Available

Chemspider ID

389114

KEGG Compound ID

C03772

BioCyc ID

5-BETA-ANDROSTANE-317-DIONE

BiGG ID

Not Available

Wikipedia Link

Etiocholanedione

METLIN ID

Not Available

PubChem Compound

440114

PDB ID

Not Available

ChEBI ID

16985

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

de la Torre R, de la Torre X, Alia C, Segura J, Baro T, Torres-Rodriguez JM: Changes in androgenic steroid profile due to urine contamination by microorganisms: a prospective study in the context of doping control. Anal Biochem. 2001 Feb 15;289(2):116-23. [PubMed:11161304 ]
Granata OM, Carruba G, Montalto G, Miele M, Bellavia V, Modica G, Blomquist CH, Castagnetta LA: Altered androgen metabolism eventually leads hepatocellular carcinoma to an impaired hormone responsiveness. Mol Cell Endocrinol. 2002 Jul 31;193(1-2):51-8. [PubMed:12161001 ]
AXELROD LR, GOLDZIEHER JW: The metabolism of 17alpha-hydroxyprogesterone and its relation to congenital adrenal hyperplasia. J Clin Endocrinol Metab. 1960 Feb;20:238-52. [PubMed:13795320 ]
Mallet AI, Holland KT, Rennie PJ, Watkins WJ, Gower DB: Applications of gas chromatography-mass spectrometry in the study of androgen and odorous 16-androstene metabolism by human axillary bacteria. J Chromatogr. 1991 Jan 2;562(1-2):647-58. [PubMed:2026727 ]

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. 3-oxo-5-beta-steroid 4-dehydrogenase

General function:: Involved in oxidoreductase activity
Specific function:: Efficiently catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone and testosterone to 5-beta-reduced metabolites. The bile acid intermediates 7-alpha,12-alpha-dihydroxy-4-cholesten-3-one and 7-alpha-hydroxy-4-cholesten-3-one can also act as substrates.
Gene Name:: AKR1D1
Uniprot ID:: P51857
Molecular weight:: 32889.38

Reactions

Etiocholanedione + NADP → Hydrogen Ion + NADPH + Androstenedione	details

Showing metabocard for Etiocholanedione (HMDB0003769)

MOL for HMDB0003769 (Etiocholanedione)

3D MOL for HMDB0003769 (Etiocholanedione)

3D SDF for HMDB0003769 (Etiocholanedione)

3D-SDF for HMDB0003769 (Etiocholanedione)

PDB for HMDB0003769 (Etiocholanedione)

3D PDB for HMDB0003769 (Etiocholanedione)

SMILES for HMDB0003769 (Etiocholanedione)

INCHI for HMDB0003769 (Etiocholanedione)

Structure for HMDB0003769 (Etiocholanedione)

3D Structure for HMDB0003769 (Etiocholanedione)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions