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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

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:00 UTC

HMDB ID

HMDB0000352

Secondary Accession Numbers

HMDB00352

Metabolite Identification

Common Name

16a-Hydroxydehydroisoandrosterone

Description

16a-Hydroxydehydroisoandrosterone, also known as 3b,16a-dihydroxy-androst-5-en-17-one or 5-androstene-3beta,16alpha-diol-17-one, 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. Thus, 16a-hydroxydehydroisoandrosterone is considered to be a steroid lipid molecule. 16a-Hydroxydehydroisoandrosterone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

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

16a-Hydroxydehydroisoandrosterone.mol
  Mrv0541 02231218282D          

 25 28  0  0  0  0            999 V2000
   -2.4762   -1.3448    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4762   -0.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7617   -0.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7617   -1.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0473   -1.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3328   -1.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3817   -1.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3817   -0.5198    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0961   -0.1073    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8808   -0.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3657    0.3052    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8808    0.9727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0961    0.7177    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0961    1.5427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3817    1.1302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3328    0.7177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3328   -0.1073    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0473   -0.5198    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0473    0.3052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1357    1.7573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1907    0.3052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1907   -1.7573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3328   -0.9323    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3817    0.3052    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0961   -0.9323    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  0  0  0  0
  3 18  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  1  0  0  0
 12 20  2  0  0  0  0
 11 21  1  6  0  0  0
  1 22  1  1  0  0  0
 17 23  1  6  0  0  0
  8 24  1  1  0  0  0
  9 25  1  6  0  0  0
M  END

HMDB0000352
     RDKit          3D
16a-Hydroxydehydroisoandrosterone
 50 53  0  0  0  0  0  0  0  0999 V2000
   -2.8029   -1.6004   -0.3742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5214   -0.2714   -1.0034 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5785   -0.3449   -2.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.4229   -1.8144 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2887    0.1662   -0.5392 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7368    0.0809    0.5713 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2727    0.6667    1.8502 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1773    0.9862    1.8932 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0581    0.4975    1.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4765    0.8777    1.1702 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3261    0.5749   -0.0169 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6522    0.5087    0.3489 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9284   -0.7106   -0.7093 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5172   -0.5569   -1.1796 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5871   -0.4184   -0.0170 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3543   -1.8262    0.5344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9616    0.7365    0.0043 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0895    0.9238    0.9230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3198    0.8741    0.0147 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8975    2.1294   -0.1120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8152    0.3815   -1.3114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4088    0.5315   -2.3611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9561   -2.3161   -0.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1594   -1.5140    0.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6547   -2.0624   -0.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8446   -1.2789   -2.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8149    0.4903   -2.8530 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2258   -1.4905   -1.8528 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4340    0.0797   -2.6469 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4890    1.2646   -0.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8983   -1.0218    0.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5412    0.0017    2.7228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8302    1.6121    2.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5280    1.6614    2.6726 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5823    1.9742    1.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9129    0.3906    2.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2479    1.3875   -0.7911 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7942    1.0456    1.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0509   -1.5928   -0.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5825   -0.7703   -1.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4219    0.2695   -1.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2572   -1.5049   -1.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2417   -2.4477    0.3032 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5042   -2.2988   -0.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2188   -1.8191    1.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7123    1.6429   -0.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1665    0.2093    1.7518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0539    1.9448    1.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0470    0.1263    0.3768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6302    2.2330    0.5543 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  1
 20 50  1  0
M  END

16a-Hydroxydehydroisoandrosterone.mol
  Mrv0541 02231218282D          

 25 28  0  0  0  0            999 V2000
   -2.4762   -1.3448    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4762   -0.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7617   -0.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7617   -1.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0473   -1.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3328   -1.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3817   -1.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3817   -0.5198    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0961   -0.1073    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8808   -0.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3657    0.3052    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8808    0.9727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0961    0.7177    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0961    1.5427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3817    1.1302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3328    0.7177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3328   -0.1073    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0473   -0.5198    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0473    0.3052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1357    1.7573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1907    0.3052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1907   -1.7573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3328   -0.9323    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3817    0.3052    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0961   -0.9323    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  0  0  0  0
  3 18  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  1  0  0  0
 12 20  2  0  0  0  0
 11 21  1  6  0  0  0
  1 22  1  1  0  0  0
 17 23  1  6  0  0  0
  8 24  1  1  0  0  0
  9 25  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0000352

> <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-/m0/s1

> <INCHI_KEY>
QQIVKFZWLZJXJT-DNKQKWOHSA-N

> <FORMULA>
C19H28O3

> <MOLECULAR_WEIGHT>
304.4238

> <EXACT_MASS>
304.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
34.84882956250295

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,5S,10R,11S,13R,15S)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]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>
-1.3972436788559572

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
86.15109999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.20e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16a-Hydroxy-DHEA

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000352
     RDKit          3D
16a-Hydroxydehydroisoandrosterone
 50 53  0  0  0  0  0  0  0  0999 V2000
   -2.8029   -1.6004   -0.3742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5214   -0.2714   -1.0034 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5785   -0.3449   -2.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.4229   -1.8144 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2887    0.1662   -0.5392 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7368    0.0809    0.5713 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2727    0.6667    1.8502 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1773    0.9862    1.8932 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0581    0.4975    1.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4765    0.8777    1.1702 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3261    0.5749   -0.0169 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6522    0.5087    0.3489 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9284   -0.7106   -0.7093 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5172   -0.5569   -1.1796 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5871   -0.4184   -0.0170 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3543   -1.8262    0.5344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9616    0.7365    0.0043 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0895    0.9238    0.9230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3198    0.8741    0.0147 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8975    2.1294   -0.1120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8152    0.3815   -1.3114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4088    0.5315   -2.3611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9561   -2.3161   -0.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1594   -1.5140    0.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6547   -2.0624   -0.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8446   -1.2789   -2.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8149    0.4903   -2.8530 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2258   -1.4905   -1.8528 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4340    0.0797   -2.6469 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4890    1.2646   -0.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8983   -1.0218    0.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5412    0.0017    2.7228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8302    1.6121    2.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5280    1.6614    2.6726 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5823    1.9742    1.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9129    0.3906    2.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2479    1.3875   -0.7911 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7942    1.0456    1.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0509   -1.5928   -0.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5825   -0.7703   -1.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4219    0.2695   -1.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2572   -1.5049   -1.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2417   -2.4477    0.3032 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5042   -2.2988   -0.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2188   -1.8191    1.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7123    1.6429   -0.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1665    0.2093    1.7518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0539    1.9448    1.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0470    0.1263    0.3768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6302    2.2330    0.5543 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  1
 20 50  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 16a-Hydroxydehydroisoandrosterone.mol             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -4.622  -2.510   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.622  -0.970   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.289  -0.200   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.289  -3.280   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.955  -2.510   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.621  -3.280   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.713  -2.510   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.713  -0.970   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.046  -0.200   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.511  -0.676   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.416   0.570   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.511   1.816   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.046   1.340   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.046   2.880   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.713   2.110   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.621   1.340   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.621  -0.200   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.955  -0.970   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.955   0.570   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.987   3.280   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.956   0.570   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -5.956  -3.280   0.000  0.00  0.00           O+0
HETATM   23  H   UNK     0      -0.621  -1.740   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       0.713   0.570   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       2.046  -1.740   0.000  0.00  0.00           H+0
CONECT    1    2    4   22                                                  
CONECT    2    1    3                                                       
CONECT    3    2   18                                                       
CONECT    4    1    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   17   24                                             
CONECT    9    8   10   13   25                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   21                                                  
CONECT   12   11   13   20                                                  
CONECT   13   12    9   14   15                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    8   18   23                                             
CONECT   18   17    3    5   19                                             
CONECT   19   18                                                            
CONECT   20   12                                                            
CONECT   21   11                                                            
CONECT   22    1                                                            
CONECT   23   17                                                            
CONECT   24    8                                                            
CONECT   25    9                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0000352
HETATM    1  C1  UNL     1      -2.803  -1.600  -0.374  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.521  -0.271  -1.003  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.578  -0.345  -2.156  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.143  -0.423  -1.814  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.289   0.166  -0.539  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.737   0.081   0.571  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.273   0.667   1.850  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.177   0.986   1.893  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.058   0.497   1.041  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.477   0.878   1.170  1.00  0.00           C  
HETATM   11  C11 UNL     1       4.326   0.575  -0.017  1.00  0.00           C  
HETATM   12  O1  UNL     1       5.652   0.509   0.349  1.00  0.00           O  
HETATM   13  C12 UNL     1       3.928  -0.711  -0.709  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.517  -0.557  -1.180  1.00  0.00           C  
HETATM   15  C14 UNL     1       1.587  -0.418  -0.017  1.00  0.00           C  
HETATM   16  C15 UNL     1       1.354  -1.826   0.534  1.00  0.00           C  
HETATM   17  C16 UNL     1      -1.962   0.737   0.004  1.00  0.00           C  
HETATM   18  C17 UNL     1      -3.090   0.924   0.923  1.00  0.00           C  
HETATM   19  C18 UNL     1      -4.320   0.874   0.015  1.00  0.00           C  
HETATM   20  O2  UNL     1      -4.897   2.129  -0.112  1.00  0.00           O  
HETATM   21  C19 UNL     1      -3.815   0.381  -1.311  1.00  0.00           C  
HETATM   22  O3  UNL     1      -4.409   0.532  -2.361  1.00  0.00           O  
HETATM   23  H1  UNL     1      -1.956  -2.316  -0.441  1.00  0.00           H  
HETATM   24  H2  UNL     1      -3.159  -1.514   0.660  1.00  0.00           H  
HETATM   25  H3  UNL     1      -3.655  -2.062  -0.951  1.00  0.00           H  
HETATM   26  H4  UNL     1      -1.845  -1.279  -2.735  1.00  0.00           H  
HETATM   27  H5  UNL     1      -1.815   0.490  -2.853  1.00  0.00           H  
HETATM   28  H6  UNL     1       0.226  -1.490  -1.853  1.00  0.00           H  
HETATM   29  H7  UNL     1       0.434   0.080  -2.647  1.00  0.00           H  
HETATM   30  H8  UNL     1       0.489   1.265  -0.697  1.00  0.00           H  
HETATM   31  H9  UNL     1      -0.898  -1.022   0.745  1.00  0.00           H  
HETATM   32  H10 UNL     1      -0.541   0.002   2.723  1.00  0.00           H  
HETATM   33  H11 UNL     1      -0.830   1.612   2.037  1.00  0.00           H  
HETATM   34  H12 UNL     1       1.528   1.661   2.673  1.00  0.00           H  
HETATM   35  H13 UNL     1       3.582   1.974   1.374  1.00  0.00           H  
HETATM   36  H14 UNL     1       3.913   0.391   2.081  1.00  0.00           H  
HETATM   37  H15 UNL     1       4.248   1.388  -0.791  1.00  0.00           H  
HETATM   38  H16 UNL     1       5.794   1.046   1.170  1.00  0.00           H  
HETATM   39  H17 UNL     1       4.051  -1.593  -0.074  1.00  0.00           H  
HETATM   40  H18 UNL     1       4.582  -0.770  -1.628  1.00  0.00           H  
HETATM   41  H19 UNL     1       2.422   0.269  -1.901  1.00  0.00           H  
HETATM   42  H20 UNL     1       2.257  -1.505  -1.722  1.00  0.00           H  
HETATM   43  H21 UNL     1       2.242  -2.448   0.303  1.00  0.00           H  
HETATM   44  H22 UNL     1       0.504  -2.299  -0.002  1.00  0.00           H  
HETATM   45  H23 UNL     1       1.219  -1.819   1.622  1.00  0.00           H  
HETATM   46  H24 UNL     1      -1.712   1.643  -0.544  1.00  0.00           H  
HETATM   47  H25 UNL     1      -3.166   0.209   1.752  1.00  0.00           H  
HETATM   48  H26 UNL     1      -3.054   1.945   1.373  1.00  0.00           H  
HETATM   49  H27 UNL     1      -5.047   0.126   0.377  1.00  0.00           H  
HETATM   50  H28 UNL     1      -5.630   2.233   0.554  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

HMDB0000352
     RDKit          3D
16a-Hydroxydehydroisoandrosterone
 50 53  0  0  0  0  0  0  0  0999 V2000
   -2.8029   -1.6004   -0.3742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5214   -0.2714   -1.0034 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5785   -0.3449   -2.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.4229   -1.8144 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2887    0.1662   -0.5392 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7368    0.0809    0.5713 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2727    0.6667    1.8502 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1773    0.9862    1.8932 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0581    0.4975    1.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4765    0.8777    1.1702 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3261    0.5749   -0.0169 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6522    0.5087    0.3489 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9284   -0.7106   -0.7093 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5172   -0.5569   -1.1796 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5871   -0.4184   -0.0170 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3543   -1.8262    0.5344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9616    0.7365    0.0043 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0895    0.9238    0.9230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3198    0.8741    0.0147 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8975    2.1294   -0.1120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8152    0.3815   -1.3114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4088    0.5315   -2.3611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9561   -2.3161   -0.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1594   -1.5140    0.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6547   -2.0624   -0.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8446   -1.2789   -2.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8149    0.4903   -2.8530 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2258   -1.4905   -1.8528 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4340    0.0797   -2.6469 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4890    1.2646   -0.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8983   -1.0218    0.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5412    0.0017    2.7228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8302    1.6121    2.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5280    1.6614    2.6726 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5823    1.9742    1.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9129    0.3906    2.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2479    1.3875   -0.7911 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7942    1.0456    1.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0509   -1.5928   -0.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5825   -0.7703   -1.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4219    0.2695   -1.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2572   -1.5049   -1.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2417   -2.4477    0.3032 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5042   -2.2988   -0.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2188   -1.8191    1.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7123    1.6429   -0.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1665    0.2093    1.7518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0539    1.9448    1.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0470    0.1263    0.3768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6302    2.2330    0.5543 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  1
 20 50  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
16alpha-Hydroxydehydroisoandrosterone	ChEBI
3beta,16alpha-Dihydroxy-androst-5-en-17-one	ChEBI
5-Androstene-3beta,16alpha-diol-17-one	ChEBI
16Α-hydroxydehydroisoandrosterone	Generator
3b,16a-Dihydroxy-androst-5-en-17-one	Generator
3Β,16α-dihydroxy-androst-5-en-17-one	Generator
5-Androstene-3b,16a-diol-17-one	Generator
5-Androstene-3β,16α-diol-17-one	Generator
16 alpha-Hydroxy-dehydroepiandrosterone	HMDB
16-Hydroxydehydroandrosterone	HMDB
16-Hydroxydehydroepiandrosterone	HMDB
16a-Hydroxy-dhea	HMDB
16a-Hydroxydehydroandrosterone	HMDB
16a-Hydroxydehydroepiandrosterone	HMDB
3b,16a-Dihydroxyandrost-5-en-17-one	HMDB
Androst-5-ene-3b-16a-diol-17-one	HMDB
16alpha-Hydroxy-dehydroepiandrosterone	HMDB
3beta,16alpha-Dihydroxyandrost-5-en-17-one	HMDB
16 alpha-Hydroxydehydroisoandrosterone	HMDB
3,16-Dihydroxyandrost-5-en-17-one	HMDB
3 beta,16 beta-Dihydroxyandrost-5-en-17-one	HMDB
16 beta-Hydroxydehydroepiandrosterone	HMDB
3 beta,16 alpha-Dihydroxyandrost-5-en-17-one	HMDB
16-Hydroxydehydroepiandrosterone, (16beta)-isomer	HMDB
16-Hydroxydehydroepiandrosterone, (3alpha,16alpha)-isomer	HMDB
16Α-hydroxydehydroepiandrosterone	HMDB
16a-Hydroxydehydroisoandrosterone	Generator

Chemical Formula

C₁₉H₂₈O₃

Average Molecular Weight

304.4238

Monoisotopic Molecular Weight

304.203844762

IUPAC Name

(1S,2R,5S,10R,11S,13R,15S)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-one

Traditional Name

16a-Hydroxy-DHEA

CAS Registry Number

1232-73-1

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-/m0/s1

InChI Key

QQIVKFZWLZJXJT-DNKQKWOHSA-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-beta-hydroxysteroid
16-hydroxysteroid
16-alpha-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
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

3beta-hydroxy steroid (CHEBI:27771 )
17-oxo steroid (CHEBI:27771 )
androstanoid (CHEBI:27771 )
16alpha-hydroxy steroid (CHEBI:27771 )
C19 steroids (androgens) and derivatives (C05139 )
C19 steroids (androgens) and derivatives (LMST02020064 )

Ontology

Physiological effect

Health effect

Cancer

Thyroid cancer (HMDB: HMDB0000352)

Disposition

Biological location

Cytoplasm (HMDB: HMDB0000352)
Cell membrane (HMDB: HMDB0000352)

Biofluid or Excreta

Blood (HMDB: HMDB0000352)
Urine (HMDB: HMDB0000352)

Tissue substructure

Hepatic tissue (HMDB: HMDB0000352)

Excreta

Biofluid or Excreta

Urine (PMID: 14643447)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0000352)

Cellular substructure

Membrane (HMDB: HMDB0000352)
Extracellular (HMDB: HMDB0000352)

Organelle

Endoplasmic reticulum (HMDB: HMDB0000352)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000352)

Source

Endogenous

Endogenous (HMDB: HMDB0000352)

Animal

Animal (HMDB: HMDB0000352)

Exogenous

Food

Food (HMDB: HMDB0000352)

Animal origin

Poultry

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

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0000352)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0000352)

Cellular process

Cell signaling (HMDB: HMDB0000352)

System process

Reproduction (HMDB: HMDB0000352)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0000352)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0000352)

Molecular messenger

Hormone (HMDB: HMDB0000352)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000352)

Emulsifier (HMDB: HMDB0000352)

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	0.12 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	34.85 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	172.623	31661259
DarkChem	[M-H]-	167.528	31661259
AllCCS	[M+H]+	177.896	32859911
AllCCS	[M-H]-	180.478	32859911
DeepCCS	[M-2H]-	208.226	30932474
DeepCCS	[M+Na]+	182.498	30932474
AllCCS	[M+H]+	177.9	32859911
AllCCS	[M+H-H2O]+	174.9	32859911
AllCCS	[M+NH4]+	180.7	32859911
AllCCS	[M+Na]+	181.5	32859911
AllCCS	[M-H]-	180.5	32859911
AllCCS	[M+Na-2H]-	180.6	32859911
AllCCS	[M+HCOO]-	180.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
16a-Hydroxydehydroisoandrosterone	[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
16a-Hydroxydehydroisoandrosterone	[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
16a-Hydroxydehydroisoandrosterone	[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
16a-Hydroxydehydroisoandrosterone,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
16a-Hydroxydehydroisoandrosterone,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
16a-Hydroxydehydroisoandrosterone,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
16a-Hydroxydehydroisoandrosterone,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
16a-Hydroxydehydroisoandrosterone,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
16a-Hydroxydehydroisoandrosterone,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
16a-Hydroxydehydroisoandrosterone,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
16a-Hydroxydehydroisoandrosterone,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
16a-Hydroxydehydroisoandrosterone,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
16a-Hydroxydehydroisoandrosterone,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
16a-Hydroxydehydroisoandrosterone,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
16a-Hydroxydehydroisoandrosterone,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
16a-Hydroxydehydroisoandrosterone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4C[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)[C@@]4(C)CC[C@@H]32)C1	3359.6	Semi standard non polar	33892256
16a-Hydroxydehydroisoandrosterone,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
16a-Hydroxydehydroisoandrosterone,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
16a-Hydroxydehydroisoandrosterone,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
16a-Hydroxydehydroisoandrosterone,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
16a-Hydroxydehydroisoandrosterone,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 - 16a-Hydroxydehydroisoandrosterone GC-MS (Non-derivatized) - 70eV, Positive	splash10-01r2-0190000000-8f531134e0d23da25da5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16a-Hydroxydehydroisoandrosterone GC-MS (2 TMS) - 70eV, Positive	splash10-001i-1038900000-e6ab9b68f3f5cbbada20	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16a-Hydroxydehydroisoandrosterone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16a-Hydroxydehydroisoandrosterone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16a-Hydroxydehydroisoandrosterone GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16a-Hydroxydehydroisoandrosterone GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16a-Hydroxydehydroisoandrosterone GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16a-Hydroxydehydroisoandrosterone GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16a-Hydroxydehydroisoandrosterone GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16a-Hydroxydehydroisoandrosterone GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16a-Hydroxydehydroisoandrosterone GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16a-Hydroxydehydroisoandrosterone GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16a-Hydroxydehydroisoandrosterone GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16a-Hydroxydehydroisoandrosterone GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16a-Hydroxydehydroisoandrosterone 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 - 16a-Hydroxydehydroisoandrosterone 10V, Positive-QTOF	splash10-052r-0194000000-ebe887790f49b4681923	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16a-Hydroxydehydroisoandrosterone 20V, Positive-QTOF	splash10-0a4r-0291000000-dd1067b167ad1b942053	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16a-Hydroxydehydroisoandrosterone 40V, Positive-QTOF	splash10-0pxr-3690000000-ff802ceebc639b3e7c1f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16a-Hydroxydehydroisoandrosterone 10V, Negative-QTOF	splash10-0udi-0029000000-c31ccc892715a3b41570	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16a-Hydroxydehydroisoandrosterone 20V, Negative-QTOF	splash10-0udi-0079000000-ca33420930d851c47a69	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16a-Hydroxydehydroisoandrosterone 40V, Negative-QTOF	splash10-007c-1090000000-e8a494aec5ecf04bc8fd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16a-Hydroxydehydroisoandrosterone 10V, Positive-QTOF	splash10-0a4r-0069000000-057040f4b3850a066367	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16a-Hydroxydehydroisoandrosterone 20V, Positive-QTOF	splash10-0670-0982000000-202e2a5dcedc0d7b97b1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16a-Hydroxydehydroisoandrosterone 40V, Positive-QTOF	splash10-0005-1910000000-6544390a129e44d96106	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16a-Hydroxydehydroisoandrosterone 10V, Negative-QTOF	splash10-0udi-0009000000-93986d59045cc7fce551	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16a-Hydroxydehydroisoandrosterone 20V, Negative-QTOF	splash10-0udi-0039000000-af52444aa96638a90cb7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16a-Hydroxydehydroisoandrosterone 40V, Negative-QTOF	splash10-0uk9-1094000000-48ce674daa94d6aea6fb	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)
Endoplasmic reticulum

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Detected and Quantified	0.35 +/- 0.24 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	14643447	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	0.35 +/- 0.21 umol/mmol creatinine	Adult (>18 years old)	Female	Thyroid cancer	14643447	details

Associated Disorders and Diseases

Disease References

Thyroid cancer
Kim KM, Jung BH, Lho DS, Chung WY, Paeng KJ, Chung BC: Alteration of urinary profiles of endogenous steroids and polyunsaturated fatty acids in thyroid cancer. Cancer Lett. 2003 Dec 30;202(2):173-9. [PubMed:14643447 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021975

KNApSAcK ID

Not Available

Chemspider ID

92168

KEGG Compound ID

C05139

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5341

PubChem Compound

102030

PDB ID

Not Available

ChEBI ID

27771

Food Biomarker Ontology

Not Available

VMH ID

EANDRSTRN

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Siiter, Pentti K.; MacDonald, Paul C. Placental estrogen biosynthesis during human pregnancy. Journal of Clinical Endocrinology and Metabolism (1966), 26(7), 751-61.

Material Safety Data Sheet (MSDS)

Not Available

General References

Gothoda Y, Hirato K, Yanaihara T, Nakayama T, Kanbegawa A: [A study of 16 alpha OH-DHA and 16 alpha OH-pregnenolone in feto-placental unit (author's transl)]. Nihon Sanka Fujinka Gakkai Zasshi. 1982 Mar;34(3):325-34. [PubMed:6461703 ]
Hirato K, Yanaihara T: Serum steroid hormone levels in neonates born from the mother with placental sulfatase deficiency. Endocrinol Jpn. 1990 Oct;37(5):731-9. [PubMed:2150812 ]

Enzymes

Enzyme Details

1. 3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1

General function:: Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:: 3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids. Efficiently catalyzes the transformation of pregnenolone to progesterone, 17-alpha-hydroxypregnenolone to 17-alpha-hydroxyprogesterone, DHEA to 4-androstenedione, dihydrotestosterone to 5-alpha-androstane-3 beta,17 beta-diol, dehydroepiandrosterone to androstenedione and 5-alpha-androstan-3 beta,17 beta-diol to 5-alpha-dihydrotestosterone.
Gene Name:: HSD3B1
Uniprot ID:: P14060
Molecular weight:: 42251.25

Reactions

16a-Hydroxyandrost-4-ene-3,17-dione + Hydrogen Ion + NADH → 16a-Hydroxydehydroisoandrosterone + NAD	details

Enzyme Details

2. 3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 2

General function:: Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:: 3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids.
Gene Name:: HSD3B2
Uniprot ID:: P26439
Molecular weight:: 42051.845

Reactions

16a-Hydroxyandrost-4-ene-3,17-dione + Hydrogen Ion + NADH → 16a-Hydroxydehydroisoandrosterone + NAD	details

Showing metabocard for 16a-Hydroxydehydroisoandrosterone (HMDB0000352)

MOL for HMDB0000352 (16a-Hydroxydehydroisoandrosterone)

3D MOL for HMDB0000352 (16a-Hydroxydehydroisoandrosterone)

3D SDF for HMDB0000352 (16a-Hydroxydehydroisoandrosterone)

3D-SDF for HMDB0000352 (16a-Hydroxydehydroisoandrosterone)

PDB for HMDB0000352 (16a-Hydroxydehydroisoandrosterone)

3D PDB for HMDB0000352 (16a-Hydroxydehydroisoandrosterone)

SMILES for HMDB0000352 (16a-Hydroxydehydroisoandrosterone)

INCHI for HMDB0000352 (16a-Hydroxydehydroisoandrosterone)

Structure for HMDB0000352 (16a-Hydroxydehydroisoandrosterone)

3D Structure for HMDB0000352 (16a-Hydroxydehydroisoandrosterone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions