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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:00 UTC

HMDB ID

HMDB0000309

Secondary Accession Numbers

HMDB00309

Metabolite Identification

Common Name

3alpha,16beta-Dihydroxyandrostenone

Description

3alpha,16beta-Dihydroxyandrostenone belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favour the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. Thus, 3alpha,16beta-dihydroxyandrostenone is considered to be a steroid lipid molecule. 3alpha,16beta-Dihydroxyandrostenone is an unusual steroid found in the urinary excretion of a subject having a virilizing malignant adrenocortical tumor; apparent 21-steroid hydroxylase deficiency is discussed in the light of these results as well as the hormonogenesis enzymatic induction of the tumour biopsy (PMID: 198067 ).

Structure

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


  Mrv1652309172018302D          

 25 28  0  0  0  0            999 V2000
 9998.939310000.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7985 9998.1238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.081010001.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.366810000.1945    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6523 9998.9596    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10001.0810 9998.9596    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2264 9999.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5119 9999.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5119 9998.5410    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.2264 9998.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9388 9999.3661    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.9388 9998.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6533 9998.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3678 9998.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.367010001.0246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.652510000.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6525 9999.7870    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.3670 9999.3746    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.866210000.8671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.081510000.6121    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.0815 9999.7871    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.8661 9999.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.351010000.1996    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.121110001.6517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.176010000.1996    0.0000 O   0  0  0  0  0  0  0  0  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
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  9  2  1  6  0  0  0
 10 12  1  0  0  0  0
  7 11  1  0  0  0  0
 11  1  1  1  0  0  0
 17 11  1  0  0  0  0
 17  5  1  6  0  0  0
 14 18  1  0  0  0  0
 18  4  1  1  0  0  0
 19 20  1  0  0  0  0
 19 23  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 25  1  1  0  0  0
 18 21  1  0  0  0  0
 21  6  1  6  0  0  0
 15 20  1  0  0  0  0
 20  3  1  1  0  0  0
 19 24  2  0  0  0  0
M  END

HMDB0000309
     RDKit          3D
3alpha,16beta-Dihydroxyandrostenone
 50 53  0  0  0  0  0  0  0  0999 V2000
   -2.8143   -1.2831    0.8445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6125   -0.4663   -0.4114 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8415   -1.2022   -1.4232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4854   -0.7194   -1.7426 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2724   -0.0104   -0.6978 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5809    0.4302    0.5039 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1282    1.4438    1.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5492    1.0503    1.5334 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1596    0.0938    0.8506 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5838   -0.1969    1.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4050    0.2292   -0.0564 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9839    1.4767    0.2505 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5071    0.3883   -1.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5042   -0.7378   -1.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5231   -0.7220   -0.2174 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2434   -2.1030    0.2945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8619    0.8343   -0.0990 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8345    1.5587    0.7233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1236    1.3489   -0.0864 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2384    1.3464    0.7128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9140    0.0684   -0.8191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7240   -0.3894   -1.6013 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8927   -1.6079    0.9245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5812   -0.7544    1.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2199   -2.2024    0.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4667   -1.2533   -2.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7878   -2.2854   -1.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1321   -1.6123   -2.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5545   -0.1111   -2.6942 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6440    0.9685   -1.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6581   -0.5060    1.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3415    1.4333    2.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0164    2.4835    0.9695 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0962    1.5964    2.2984 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7037   -1.3066    1.3025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8990    0.3258    2.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1769   -0.5379   -0.2180 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3057    1.3824    1.1936 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1436    0.3792   -2.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0073    1.3828   -1.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1057   -1.6853   -1.3660 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9996   -0.6369   -2.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1840   -2.3688    0.3183 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6195   -2.2219    1.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8240   -2.8304   -0.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7396    1.3436   -1.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5741    2.6537    0.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9388    1.2535    1.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1179    2.1567   -0.8494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8139    2.1229    0.4578 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  2  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
 19 21  1  0
 21 22  2  0
 17  2  1  0
 21  2  1  0
 15  5  1  0
 15  9  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  6
  6 31  1  1
  7 32  1  0
  7 33  1  0
  8 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  6
 12 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  6
 18 47  1  0
 18 48  1  0
 19 49  1  6
 20 50  1  0
M  END


  Mrv1652309172018302D          

 25 28  0  0  0  0            999 V2000
 9998.939310000.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7985 9998.1238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.081010001.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.366810000.1945    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6523 9998.9596    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10001.0810 9998.9596    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2264 9999.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5119 9999.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5119 9998.5410    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.2264 9998.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9388 9999.3661    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.9388 9998.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6533 9998.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3678 9998.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.367010001.0246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.652510000.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6525 9999.7870    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.3670 9999.3746    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.866210000.8671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.081510000.6121    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.0815 9999.7871    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.8661 9999.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.351010000.1996    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.121110001.6517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.176010000.1996    0.0000 O   0  0  0  0  0  0  0  0  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
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  9  2  1  6  0  0  0
 10 12  1  0  0  0  0
  7 11  1  0  0  0  0
 11  1  1  1  0  0  0
 17 11  1  0  0  0  0
 17  5  1  6  0  0  0
 14 18  1  0  0  0  0
 18  4  1  1  0  0  0
 19 20  1  0  0  0  0
 19 23  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 25  1  1  0  0  0
 18 21  1  0  0  0  0
 21  6  1  6  0  0  0
 15 20  1  0  0  0  0
 20  3  1  1  0  0  0
 19 24  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000309

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12C[C@H](O)C(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@H](O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h3,12-16,20-21H,4-10H2,1-2H3/t12-,13-,14+,15+,16+,18+,19+/m1/s1

> <INCHI_KEY>
QQIVKFZWLZJXJT-BNSUEQOYSA-N

> <FORMULA>
C19H28O3

> <MOLECULAR_WEIGHT>
304.43

> <EXACT_MASS>
304.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
34.941532319079656

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,5R,10R,11S,13S,15S)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-one

> <ALOGPS_LOGP>
2.42

> <JCHEM_LOGP>
2.490639134666667

> <ALOGPS_LOGS>
-3.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.20428950550259

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.382196791349628

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3972436788559555

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
86.15109999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.20e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5R,10R,11S,13S,15S)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000309
     RDKit          3D
3alpha,16beta-Dihydroxyandrostenone
 50 53  0  0  0  0  0  0  0  0999 V2000
   -2.8143   -1.2831    0.8445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6125   -0.4663   -0.4114 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8415   -1.2022   -1.4232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4854   -0.7194   -1.7426 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2724   -0.0104   -0.6978 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5809    0.4302    0.5039 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1282    1.4438    1.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5492    1.0503    1.5334 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1596    0.0938    0.8506 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5838   -0.1969    1.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4050    0.2292   -0.0564 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9839    1.4767    0.2505 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5071    0.3883   -1.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5042   -0.7378   -1.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5231   -0.7220   -0.2174 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2434   -2.1030    0.2945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8619    0.8343   -0.0990 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8345    1.5587    0.7233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1236    1.3489   -0.0864 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2384    1.3464    0.7128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9140    0.0684   -0.8191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7240   -0.3894   -1.6013 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8927   -1.6079    0.9245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5812   -0.7544    1.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2199   -2.2024    0.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4667   -1.2533   -2.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7878   -2.2854   -1.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1321   -1.6123   -2.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5545   -0.1111   -2.6942 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6440    0.9685   -1.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6581   -0.5060    1.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3415    1.4333    2.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0164    2.4835    0.9695 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0962    1.5964    2.2984 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7037   -1.3066    1.3025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8990    0.3258    2.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1769   -0.5379   -0.2180 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3057    1.3824    1.1936 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1436    0.3792   -2.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0073    1.3828   -1.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1057   -1.6853   -1.3660 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9996   -0.6369   -2.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1840   -2.3688    0.3183 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6195   -2.2219    1.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8240   -2.8304   -0.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7396    1.3436   -1.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5741    2.6537    0.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9388    1.2535    1.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1179    2.1567   -0.8494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8139    2.1229    0.4578 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  2  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
 19 21  1  0
 21 22  2  0
 17  2  1  0
 21  2  1  0
 15  5  1  0
 15  9  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  6
  6 31  1  1
  7 32  1  0
  7 33  1  0
  8 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  6
 12 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  6
 18 47  1  0
 18 48  1  0
 19 49  1  6
 20 50  1  0
M  END

HEADER    PROTEIN                                 17-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-SEP-20         0                                  
HETATM    1  C   UNK     0    8664.6878667.030   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8660.6918663.164   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8668.6858669.361   0.000  0.00  0.00           C+0
HETATM    4  H   UNK     0    8667.3518667.030   0.000  0.00  0.00           H+0
HETATM    5  H   UNK     0    8666.0188664.725   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8668.6858664.725   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0    8663.3568666.253   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8662.0228665.483   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8662.0228663.943   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8663.3568663.173   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8664.6868665.483   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8664.6868663.943   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8666.0198663.173   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8667.3538663.943   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8667.3528668.579   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8666.0188667.809   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8666.0188666.269   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8667.3528665.499   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8670.1508668.285   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8668.6858667.809   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8668.6858666.269   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8670.1508665.793   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8671.0558667.039   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0    8670.6268669.750   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0    8672.5958667.039   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2    9                                                            
CONECT    3   20                                                            
CONECT    4   18                                                            
CONECT    5   17                                                            
CONECT    6   21                                                            
CONECT    7    8   11                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10    2                                                  
CONECT   10    9   12                                                       
CONECT   11   12    7    1   17                                             
CONECT   12   11   13   10                                                  
CONECT   13   12   14                                                       
CONECT   14   13   18                                                       
CONECT   15   16   20                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   11    5                                             
CONECT   18   17   14    4   21                                             
CONECT   19   20   23   24                                                  
CONECT   20   19   21   15    3                                             
CONECT   21   20   22   18    6                                             
CONECT   22   21   23                                                       
CONECT   23   19   22   25                                                  
CONECT   24   19                                                            
CONECT   25   23                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0000309
HETATM    1  C1  UNL     1      -2.814  -1.283   0.845  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.613  -0.466  -0.411  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.842  -1.202  -1.423  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.485  -0.719  -1.743  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.272  -0.010  -0.698  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.581   0.430   0.504  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.128   1.444   1.324  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.549   1.050   1.533  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.160   0.094   0.851  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.584  -0.197   1.162  1.00  0.00           C  
HETATM   11  C11 UNL     1       4.405   0.229  -0.056  1.00  0.00           C  
HETATM   12  O1  UNL     1       4.984   1.477   0.250  1.00  0.00           O  
HETATM   13  C12 UNL     1       3.507   0.388  -1.250  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.504  -0.738  -1.382  1.00  0.00           C  
HETATM   15  C14 UNL     1       1.523  -0.722  -0.217  1.00  0.00           C  
HETATM   16  C15 UNL     1       1.243  -2.103   0.294  1.00  0.00           C  
HETATM   17  C16 UNL     1      -1.862   0.834  -0.099  1.00  0.00           C  
HETATM   18  C17 UNL     1      -2.834   1.559   0.723  1.00  0.00           C  
HETATM   19  C18 UNL     1      -4.124   1.349  -0.086  1.00  0.00           C  
HETATM   20  O2  UNL     1      -5.238   1.346   0.713  1.00  0.00           O  
HETATM   21  C19 UNL     1      -3.914   0.068  -0.819  1.00  0.00           C  
HETATM   22  O3  UNL     1      -4.724  -0.389  -1.601  1.00  0.00           O  
HETATM   23  H1  UNL     1      -3.893  -1.608   0.924  1.00  0.00           H  
HETATM   24  H2  UNL     1      -2.581  -0.754   1.765  1.00  0.00           H  
HETATM   25  H3  UNL     1      -2.220  -2.202   0.749  1.00  0.00           H  
HETATM   26  H4  UNL     1      -2.467  -1.253  -2.365  1.00  0.00           H  
HETATM   27  H5  UNL     1      -1.788  -2.285  -1.101  1.00  0.00           H  
HETATM   28  H6  UNL     1       0.132  -1.612  -2.064  1.00  0.00           H  
HETATM   29  H7  UNL     1      -0.555  -0.111  -2.694  1.00  0.00           H  
HETATM   30  H8  UNL     1       0.644   0.968  -1.126  1.00  0.00           H  
HETATM   31  H9  UNL     1      -0.658  -0.506   1.132  1.00  0.00           H  
HETATM   32  H10 UNL     1      -0.341   1.433   2.351  1.00  0.00           H  
HETATM   33  H11 UNL     1       0.016   2.483   0.970  1.00  0.00           H  
HETATM   34  H12 UNL     1       2.096   1.596   2.298  1.00  0.00           H  
HETATM   35  H13 UNL     1       3.704  -1.307   1.303  1.00  0.00           H  
HETATM   36  H14 UNL     1       3.899   0.326   2.065  1.00  0.00           H  
HETATM   37  H15 UNL     1       5.177  -0.538  -0.218  1.00  0.00           H  
HETATM   38  H16 UNL     1       5.306   1.382   1.194  1.00  0.00           H  
HETATM   39  H17 UNL     1       4.144   0.379  -2.150  1.00  0.00           H  
HETATM   40  H18 UNL     1       3.007   1.383  -1.217  1.00  0.00           H  
HETATM   41  H19 UNL     1       3.106  -1.685  -1.366  1.00  0.00           H  
HETATM   42  H20 UNL     1       2.000  -0.637  -2.353  1.00  0.00           H  
HETATM   43  H21 UNL     1       0.184  -2.369   0.318  1.00  0.00           H  
HETATM   44  H22 UNL     1       1.620  -2.222   1.350  1.00  0.00           H  
HETATM   45  H23 UNL     1       1.824  -2.830  -0.312  1.00  0.00           H  
HETATM   46  H24 UNL     1      -1.740   1.344  -1.072  1.00  0.00           H  
HETATM   47  H25 UNL     1      -2.574   2.654   0.736  1.00  0.00           H  
HETATM   48  H26 UNL     1      -2.939   1.254   1.760  1.00  0.00           H  
HETATM   49  H27 UNL     1      -4.118   2.157  -0.849  1.00  0.00           H  
HETATM   50  H28 UNL     1      -5.814   2.123   0.458  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   17   21
CONECT    3    4   26   27
CONECT    4    5   28   29
CONECT    5    6   15   30
CONECT    6    7   17   31
CONECT    7    8   32   33
CONECT    8    9    9   34
CONECT    9   10   15
CONECT   10   11   35   36
CONECT   11   12   13   37
CONECT   12   38
CONECT   13   14   39   40
CONECT   14   15   41   42
CONECT   15   16
CONECT   16   43   44   45
CONECT   17   18   46
CONECT   18   19   47   48
CONECT   19   20   21   49
CONECT   20   50
CONECT   21   22   22
END

HMDB0000309
     RDKit          3D
3alpha,16beta-Dihydroxyandrostenone
 50 53  0  0  0  0  0  0  0  0999 V2000
   -2.8143   -1.2831    0.8445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6125   -0.4663   -0.4114 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8415   -1.2022   -1.4232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4854   -0.7194   -1.7426 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2724   -0.0104   -0.6978 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5809    0.4302    0.5039 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1282    1.4438    1.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5492    1.0503    1.5334 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1596    0.0938    0.8506 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5838   -0.1969    1.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4050    0.2292   -0.0564 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9839    1.4767    0.2505 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5071    0.3883   -1.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5042   -0.7378   -1.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5231   -0.7220   -0.2174 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2434   -2.1030    0.2945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8619    0.8343   -0.0990 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8345    1.5587    0.7233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1236    1.3489   -0.0864 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2384    1.3464    0.7128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9140    0.0684   -0.8191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7240   -0.3894   -1.6013 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8927   -1.6079    0.9245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5812   -0.7544    1.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2199   -2.2024    0.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4667   -1.2533   -2.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7878   -2.2854   -1.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1321   -1.6123   -2.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5545   -0.1111   -2.6942 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6440    0.9685   -1.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6581   -0.5060    1.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3415    1.4333    2.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0164    2.4835    0.9695 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0962    1.5964    2.2984 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7037   -1.3066    1.3025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8990    0.3258    2.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1769   -0.5379   -0.2180 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3057    1.3824    1.1936 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1436    0.3792   -2.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0073    1.3828   -1.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1057   -1.6853   -1.3660 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9996   -0.6369   -2.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1840   -2.3688    0.3183 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6195   -2.2219    1.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8240   -2.8304   -0.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7396    1.3436   -1.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5741    2.6537    0.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9388    1.2535    1.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1179    2.1567   -0.8494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8139    2.1229    0.4578 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  2  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
 19 21  1  0
 21 22  2  0
 17  2  1  0
 21  2  1  0
 15  5  1  0
 15  9  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  6
  6 31  1  1
  7 32  1  0
  7 33  1  0
  8 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  6
 12 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  6
 18 47  1  0
 18 48  1  0
 19 49  1  6
 20 50  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3a,16b-Dihydroxyandrostenone	Generator
3Α,16β-dihydroxyandrostenone	Generator
(3alpha,16beta)-3,16-Dihydroxyandrost-5-en-17-one	HMDB
(3Α,16β)-3,16-dihydroxyandrost-5-en-17-one	HMDB
3alpha,16beta-Dihydroxyandrost-5-en-17-one	HMDB
3Α,16β-dihydroxyandrost-5-en-17-one	HMDB
3alpha,16beta-Dihydroxyandrostenone	HMDB

Chemical Formula

C₁₉H₂₈O₃

Average Molecular Weight

304.43

Monoisotopic Molecular Weight

304.203844762

IUPAC Name

(1S,2R,5R,10R,11S,13S,15S)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-one

Traditional Name

(1S,2R,5R,10R,11S,13S,15S)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-one

CAS Registry Number

60828-06-0

SMILES

[H][C@@]12C[C@H](O)C(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@H](O)CC[C@]12C

InChI Identifier

InChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h3,12-16,20-21H,4-10H2,1-2H3/t12-,13-,14+,15+,16+,18+,19+/m1/s1

InChI Key

QQIVKFZWLZJXJT-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-hydroxy-delta-5-steroid
3-hydroxysteroid
3-alpha-hydroxysteroid
16-hydroxysteroid
16-beta-hydroxysteroid
Oxosteroid
17-oxosteroid
Hydroxysteroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Ketone
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

C19 steroids (androgens) and derivatives (LMST02020091 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0000309)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0000309)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000309)

Source

Endogenous

Endogenous (HMDB: HMDB0000309)

Animal

Animal (HMDB: HMDB0000309)

Exogenous

Food

Food (HMDB: HMDB0000309)

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: HMDB0000309)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0000309)

Molecular messenger

Hormone (HMDB: HMDB0000309)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000309)

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	0.079 g/L	ALOGPS
logP	2.42	ALOGPS
logP	2.49	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	13.38	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	86.15 m³·mol⁻¹	ChemAxon
Polarizability	34.94 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
DeepCCS	[M-2H]-	208.131	30932474
DeepCCS	[M+Na]+	182.452	30932474
AllCCS	[M+H]+	177.5	32859911
AllCCS	[M+H-H2O]+	174.5	32859911
AllCCS	[M+NH4]+	180.2	32859911
AllCCS	[M+Na]+	181.0	32859911
AllCCS	[M-H]-	180.5	32859911
AllCCS	[M+Na-2H]-	180.6	32859911
AllCCS	[M+HCOO]-	180.8	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.	5.72 minutes	32390414
Predicted by Siyang on May 30, 2022	12.762 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.09 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2384.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	248.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	180.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	173.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	267.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	521.1 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	576.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	100.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1019.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	413.5 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	1389.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	323.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	397.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	361.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	339.0 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	44.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3alpha,16beta-Dihydroxyandrostenone	[H][C@@]12C[C@H](O)C(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@H](O)CC[C@]12C	2709.5	Standard polar	33892256
3alpha,16beta-Dihydroxyandrostenone	[H][C@@]12C[C@H](O)C(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@H](O)CC[C@]12C	2602.5	Standard non polar	33892256
3alpha,16beta-Dihydroxyandrostenone	[H][C@@]12C[C@H](O)C(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@H](O)CC[C@]12C	2716.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3alpha,16beta-Dihydroxyandrostenone,1TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CC=C4C[C@H](O)CC[C@@]43C)[C@@H]1C[C@H](O[Si](C)(C)C)C2=O	2802.3	Semi standard non polar	33892256
3alpha,16beta-Dihydroxyandrostenone,1TMS,isomer #2	C[C@]12CC[C@H]3[C@@H](CC=C4C[C@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1C[C@H](O)C2=O	2769.5	Semi standard non polar	33892256
3alpha,16beta-Dihydroxyandrostenone,1TMS,isomer #3	C[C@]12CC[C@H]3[C@@H](CC=C4C[C@H](O)CC[C@@]43C)[C@@H]1CC(O)=C2O[Si](C)(C)C	2759.1	Semi standard non polar	33892256
3alpha,16beta-Dihydroxyandrostenone,2TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CC=C4C[C@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1C[C@H](O[Si](C)(C)C)C2=O	2828.4	Semi standard non polar	33892256
3alpha,16beta-Dihydroxyandrostenone,2TMS,isomer #2	C[C@]12CC[C@H]3[C@@H](CC=C4C[C@H](O)CC[C@@]43C)[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C	2833.8	Semi standard non polar	33892256
3alpha,16beta-Dihydroxyandrostenone,2TMS,isomer #3	C[C@]12CC[C@H]3[C@@H](CC=C4C[C@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC(O)=C2O[Si](C)(C)C	2765.2	Semi standard non polar	33892256
3alpha,16beta-Dihydroxyandrostenone,3TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CC=C4C[C@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C	2825.9	Semi standard non polar	33892256
3alpha,16beta-Dihydroxyandrostenone,3TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CC=C4C[C@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C	2812.9	Standard non polar	33892256
3alpha,16beta-Dihydroxyandrostenone,3TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CC=C4C[C@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C	3081.8	Standard polar	33892256
3alpha,16beta-Dihydroxyandrostenone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H]2[C@@H]3CC=C4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]2(C)C1=O	3073.1	Semi standard non polar	33892256
3alpha,16beta-Dihydroxyandrostenone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4C[C@H](O)C(=O)[C@@]4(C)CC[C@@H]32)C1	3042.6	Semi standard non polar	33892256
3alpha,16beta-Dihydroxyandrostenone,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=C(O)C[C@H]2[C@@H]3CC=C4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C	3042.9	Semi standard non polar	33892256
3alpha,16beta-Dihydroxyandrostenone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H]2[C@@H]3CC=C4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]2(C)C1=O	3340.0	Semi standard non polar	33892256
3alpha,16beta-Dihydroxyandrostenone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC[C@H]3[C@@H](CC=C4C[C@H](O)CC[C@@]43C)[C@@H]2C1	3384.5	Semi standard non polar	33892256
3alpha,16beta-Dihydroxyandrostenone,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=C(O)C[C@H]2[C@@H]3CC=C4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3308.8	Semi standard non polar	33892256
3alpha,16beta-Dihydroxyandrostenone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC[C@H]3[C@@H](CC=C4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@@]43C)[C@@H]2C1	3579.4	Semi standard non polar	33892256
3alpha,16beta-Dihydroxyandrostenone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC[C@H]3[C@@H](CC=C4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@@]43C)[C@@H]2C1	3382.3	Standard non polar	33892256
3alpha,16beta-Dihydroxyandrostenone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC[C@H]3[C@@H](CC=C4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@@]43C)[C@@H]2C1	3374.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha,16beta-Dihydroxyandrostenone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha,16beta-Dihydroxyandrostenone GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha,16beta-Dihydroxyandrostenone GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha,16beta-Dihydroxyandrostenone GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha,16beta-Dihydroxyandrostenone GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha,16beta-Dihydroxyandrostenone GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha,16beta-Dihydroxyandrostenone GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha,16beta-Dihydroxyandrostenone GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha,16beta-Dihydroxyandrostenone GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha,16beta-Dihydroxyandrostenone GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha,16beta-Dihydroxyandrostenone GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha,16beta-Dihydroxyandrostenone GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha,16beta-Dihydroxyandrostenone GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	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 - 3alpha,16beta-Dihydroxyandrostenone 10V, Negative-QTOF	splash10-0udi-0009000000-93986d59045cc7fce551	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,16beta-Dihydroxyandrostenone 20V, Negative-QTOF	splash10-0udi-0039000000-af52444aa96638a90cb7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,16beta-Dihydroxyandrostenone 40V, Negative-QTOF	splash10-0uk9-1094000000-48ce674daa94d6aea6fb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,16beta-Dihydroxyandrostenone 10V, Positive-QTOF	splash10-0a4r-0069000000-057040f4b3850a066367	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,16beta-Dihydroxyandrostenone 20V, Positive-QTOF	splash10-0670-0982000000-202e2a5dcedc0d7b97b1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,16beta-Dihydroxyandrostenone 40V, Positive-QTOF	splash10-0005-1910000000-6544390a129e44d96106	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

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

FDB021936

KNApSAcK ID

Not Available

Chemspider ID

24850099

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44263333

PDB ID

Not Available

ChEBI ID

Not Available

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

Dubost M, Begue RJ, Desgres J, Rifle C, Putelat R, Moriniere M, Padieu P: [Study of a virilizing adrenal cortical tumor. Analysis of urinary steroids by gas-liquid chromatography and mass spectrometry]. C R Seances Soc Biol Fil. 1977;171(1):67-72. [PubMed:198067 ]

Showing metabocard for 3alpha,16beta-Dihydroxyandrostenone (HMDB0000309)

MOL for HMDB0000309 (3alpha,16beta-Dihydroxyandrostenone)

3D MOL for HMDB0000309 (3alpha,16beta-Dihydroxyandrostenone)

3D SDF for HMDB0000309 (3alpha,16beta-Dihydroxyandrostenone)

3D-SDF for HMDB0000309 (3alpha,16beta-Dihydroxyandrostenone)

PDB for HMDB0000309 (3alpha,16beta-Dihydroxyandrostenone)

3D PDB for HMDB0000309 (3alpha,16beta-Dihydroxyandrostenone)

SMILES for HMDB0000309 (3alpha,16beta-Dihydroxyandrostenone)

INCHI for HMDB0000309 (3alpha,16beta-Dihydroxyandrostenone)

Structure for HMDB0000309 (3alpha,16beta-Dihydroxyandrostenone)

3D Structure for HMDB0000309 (3alpha,16beta-Dihydroxyandrostenone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra