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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2006-08-13 05:18:00 UTC

Update Date

2022-09-22 18:34:17 UTC

HMDB ID

HMDB0003818

Secondary Accession Numbers

HMDB03818

Metabolite Identification

Common Name

5-Androstenediol

Description

5-Androstenediol is a direct metabolite of the most abundant steroid produced by the human adrenal cortex, dehydroepiandrosterone (DHEA). 5-Androstenediol is less androgenic than 4-androstenediol, and stimulates the immune system. When administered to rats in vivo, 5-androstenediol has approximately 1/70 the androgenicity of DHEA, 1/185 the androgenicity of androstenedione, and 1/475 the androgenicity of testosterone (Wikipedia ). Because it induces production of white blood cells and platelets, 5-androstenediol is being developed as a radiation countermeasure as Neumune (HE2100). An intermediate in testosterone biosynthesis, found in the testis or the adrenal glands. 5-Androstenediol, derived from dehydroepiandrosterone by the reduction of the 17-keto group (17-hydroxysteroid dehydrogenases), is converted to testosterone by the oxidation of the 3-beta hydroxyl group to a 3-keto group (3-fydroxysteroid dehydrogenase).

Structure

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

HMDB0003818
     RDKit          3D
5-Androstenediol
 51 54  0  0  0  0  0  0  0  0999 V2000
    2.5385    1.9504   -0.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4740    0.4921   -0.6667 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5943    0.2606   -1.8412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4473   -0.6670   -1.6299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1851   -0.6926   -0.3024 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6401    0.0101    0.7945 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0976   -0.4641    2.1133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3357   -0.0831    2.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1101    0.0154    1.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5184    0.4072    1.3145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3960   -0.5911    0.6345 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6989   -0.1409    0.6103 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9657   -0.9792   -0.7373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5171   -1.3532   -0.8389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6168   -0.2498   -0.2549 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8820    0.9627   -1.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0237   -0.3851    0.4942 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0690   -0.1580    1.4857 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3365   -0.0564    0.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8808   -0.0001   -0.8065 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6056    0.9371   -1.5249 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5668    2.4732   -0.4271 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2356    2.4327   -1.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9886    2.1098    0.7008 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2273    1.2565   -2.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2360   -0.1093   -2.6709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3357   -0.3961   -2.3991 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7864   -1.6857   -1.9594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1801   -1.7631    0.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4107    1.0815    0.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6819    0.0683    2.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2675   -1.5455    2.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7495    0.1266    3.1541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7367    1.4554    1.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7836    0.3493    2.4124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3959   -1.5181    1.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7492    0.8399    0.5197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2484   -0.1869   -1.4880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5525   -1.8734   -1.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3311   -2.3228   -0.3793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2449   -1.4206   -1.9123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1266    1.7402   -1.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8463    1.3940   -0.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0646    0.6574   -2.1832 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0844   -1.4311    0.1173 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1560   -1.0667    2.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9405    0.6934    2.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9476    0.8195    0.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9209   -1.0002    0.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8857   -0.9945   -1.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5275    0.6014   -1.7043 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  6
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 17  2  1  0
 20  2  1  0
 15  5  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  1
  6 30  1  1
  7 31  1  0
  7 32  1  0
  8 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  1
 12 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  6
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  6
 21 51  1  0
M  END

HMDB03818.mol
  Mrv0541 02231219472D          

 24 27  0  0  0  0            999 V2000
   -2.0637   -0.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0637   -1.3448    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3492   -1.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348   -1.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348   -0.5198    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3492   -0.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797   -1.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942   -1.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942   -0.5198    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0797   -0.1073    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5086   -0.1073    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5086    0.7177    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7942    1.1302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797    0.7177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2933   -0.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7782    0.3052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2933    0.9727    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6348    0.3052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7782   -1.7573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5949    1.5382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5482    1.7573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942    0.3052    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797   -0.9323    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5086   -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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
  5 18  1  1  0  0  0
  2 19  1  1  0  0  0
 12 20  1  1  0  0  0
 17 21  1  1  0  0  0
  9 22  1  1  0  0  0
 10 23  1  6  0  0  0
 11 24  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0003818

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-17,20-21H,4-11H2,1-2H3/t13-,14-,15-,16-,17-,18-,19-/m0/s1

> <INCHI_KEY>
QADHLRWLCPCEKT-LOVVWNRFSA-N

> <FORMULA>
C19H30O2

> <MOLECULAR_WEIGHT>
290.4403

> <EXACT_MASS>
290.224580204

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
34.68266542275768

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.42

> <JCHEM_LOGP>
2.798177349666666

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.377698709764868

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.204289505503816

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7678099996325817

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
85.4812

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.50e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-androstenediol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0003818
     RDKit          3D
5-Androstenediol
 51 54  0  0  0  0  0  0  0  0999 V2000
    2.5385    1.9504   -0.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4740    0.4921   -0.6667 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5943    0.2606   -1.8412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4473   -0.6670   -1.6299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1851   -0.6926   -0.3024 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6401    0.0101    0.7945 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0976   -0.4641    2.1133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3357   -0.0831    2.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1101    0.0154    1.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5184    0.4072    1.3145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3960   -0.5911    0.6345 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6989   -0.1409    0.6103 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9657   -0.9792   -0.7373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5171   -1.3532   -0.8389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6168   -0.2498   -0.2549 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8820    0.9627   -1.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0237   -0.3851    0.4942 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0690   -0.1580    1.4857 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3365   -0.0564    0.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8808   -0.0001   -0.8065 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6056    0.9371   -1.5249 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5668    2.4732   -0.4271 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2356    2.4327   -1.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9886    2.1098    0.7008 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2273    1.2565   -2.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2360   -0.1093   -2.6709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3357   -0.3961   -2.3991 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7864   -1.6857   -1.9594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1801   -1.7631    0.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4107    1.0815    0.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6819    0.0683    2.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2675   -1.5455    2.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7495    0.1266    3.1541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7367    1.4554    1.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7836    0.3493    2.4124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3959   -1.5181    1.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7492    0.8399    0.5197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2484   -0.1869   -1.4880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5525   -1.8734   -1.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3311   -2.3228   -0.3793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2449   -1.4206   -1.9123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1266    1.7402   -1.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8463    1.3940   -0.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0646    0.6574   -2.1832 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0844   -1.4311    0.1173 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1560   -1.0667    2.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9405    0.6934    2.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9476    0.8195    0.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9209   -1.0002    0.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8857   -0.9945   -1.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5275    0.6014   -1.7043 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  6
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 17  2  1  0
 20  2  1  0
 15  5  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  1
  6 30  1  1
  7 31  1  0
  7 32  1  0
  8 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  1
 12 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  6
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  6
 21 51  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: HMDB03818.mol                                     
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.852  -0.970   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.852  -2.510   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.519  -3.280   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.185  -2.510   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.185  -0.970   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.519  -0.200   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.149  -3.280   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.483  -2.510   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.483  -0.970   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.149  -0.200   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.816  -0.200   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.816   1.340   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.483   2.110   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.149   1.340   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.281  -0.676   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.186   0.570   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.281   1.816   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.185   0.570   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -5.186  -3.280   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.977   2.871   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.757   3.280   0.000  0.00  0.00           O+0
HETATM   22  H   UNK     0       1.483   0.570   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       0.149  -1.740   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       2.816  -1.740   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   18                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   22                                             
CONECT   10    9    5   14   23                                             
CONECT   11    9   12   15   24                                             
CONECT   12   11   13   17   20                                             
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   21                                                  
CONECT   18    5                                                            
CONECT   19    2                                                            
CONECT   20   12                                                            
CONECT   21   17                                                            
CONECT   22    9                                                            
CONECT   23   10                                                            
CONECT   24   11                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0003818
HETATM    1  C1  UNL     1       2.539   1.950  -0.277  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.474   0.492  -0.667  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.594   0.261  -1.841  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.447  -0.667  -1.630  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.185  -0.693  -0.302  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.640   0.010   0.794  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.098  -0.464   2.113  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.336  -0.083   2.151  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.110   0.015   1.104  1.00  0.00           C  
HETATM   10  C10 UNL     1      -3.518   0.407   1.315  1.00  0.00           C  
HETATM   11  C11 UNL     1      -4.396  -0.591   0.635  1.00  0.00           C  
HETATM   12  O1  UNL     1      -5.699  -0.141   0.610  1.00  0.00           O  
HETATM   13  C12 UNL     1      -3.966  -0.979  -0.737  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.517  -1.353  -0.839  1.00  0.00           C  
HETATM   15  C14 UNL     1      -1.617  -0.250  -0.255  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.882   0.963  -1.123  1.00  0.00           C  
HETATM   17  C16 UNL     1       2.024  -0.385   0.494  1.00  0.00           C  
HETATM   18  C17 UNL     1       3.069  -0.158   1.486  1.00  0.00           C  
HETATM   19  C18 UNL     1       4.337  -0.056   0.652  1.00  0.00           C  
HETATM   20  C19 UNL     1       3.881  -0.000  -0.806  1.00  0.00           C  
HETATM   21  O2  UNL     1       4.606   0.937  -1.525  1.00  0.00           O  
HETATM   22  H1  UNL     1       1.567   2.473  -0.427  1.00  0.00           H  
HETATM   23  H2  UNL     1       3.236   2.433  -1.024  1.00  0.00           H  
HETATM   24  H3  UNL     1       2.989   2.110   0.701  1.00  0.00           H  
HETATM   25  H4  UNL     1       1.227   1.256  -2.189  1.00  0.00           H  
HETATM   26  H5  UNL     1       2.236  -0.109  -2.671  1.00  0.00           H  
HETATM   27  H6  UNL     1      -0.336  -0.396  -2.399  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.786  -1.686  -1.959  1.00  0.00           H  
HETATM   29  H8  UNL     1      -0.180  -1.763   0.062  1.00  0.00           H  
HETATM   30  H9  UNL     1       0.411   1.082   0.696  1.00  0.00           H  
HETATM   31  H10 UNL     1       0.682   0.068   2.915  1.00  0.00           H  
HETATM   32  H11 UNL     1       0.268  -1.546   2.226  1.00  0.00           H  
HETATM   33  H12 UNL     1      -1.749   0.127   3.154  1.00  0.00           H  
HETATM   34  H13 UNL     1      -3.737   1.455   1.044  1.00  0.00           H  
HETATM   35  H14 UNL     1      -3.784   0.349   2.412  1.00  0.00           H  
HETATM   36  H15 UNL     1      -4.396  -1.518   1.280  1.00  0.00           H  
HETATM   37  H16 UNL     1      -5.749   0.840   0.520  1.00  0.00           H  
HETATM   38  H17 UNL     1      -4.248  -0.187  -1.488  1.00  0.00           H  
HETATM   39  H18 UNL     1      -4.552  -1.873  -1.039  1.00  0.00           H  
HETATM   40  H19 UNL     1      -2.331  -2.323  -0.379  1.00  0.00           H  
HETATM   41  H20 UNL     1      -2.245  -1.421  -1.912  1.00  0.00           H  
HETATM   42  H21 UNL     1      -1.127   1.740  -1.021  1.00  0.00           H  
HETATM   43  H22 UNL     1      -2.846   1.394  -0.781  1.00  0.00           H  
HETATM   44  H23 UNL     1      -2.065   0.657  -2.183  1.00  0.00           H  
HETATM   45  H24 UNL     1       2.084  -1.431   0.117  1.00  0.00           H  
HETATM   46  H25 UNL     1       3.156  -1.067   2.151  1.00  0.00           H  
HETATM   47  H26 UNL     1       2.941   0.693   2.168  1.00  0.00           H  
HETATM   48  H27 UNL     1       4.948   0.820   0.916  1.00  0.00           H  
HETATM   49  H28 UNL     1       4.921  -1.000   0.742  1.00  0.00           H  
HETATM   50  H29 UNL     1       3.886  -0.995  -1.279  1.00  0.00           H  
HETATM   51  H30 UNL     1       5.528   0.601  -1.704  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   17   20
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6   15   29
CONECT    6    7   17   30
CONECT    7    8   31   32
CONECT    8    9    9   33
CONECT    9   10   15
CONECT   10   11   34   35
CONECT   11   12   13   36
CONECT   12   37
CONECT   13   14   38   39
CONECT   14   15   40   41
CONECT   15   16
CONECT   16   42   43   44
CONECT   17   18   45
CONECT   18   19   46   47
CONECT   19   20   48   49
CONECT   20   21   50
CONECT   21   51
END

HMDB0003818
     RDKit          3D
5-Androstenediol
 51 54  0  0  0  0  0  0  0  0999 V2000
    2.5385    1.9504   -0.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4740    0.4921   -0.6667 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5943    0.2606   -1.8412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4473   -0.6670   -1.6299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1851   -0.6926   -0.3024 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6401    0.0101    0.7945 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0976   -0.4641    2.1133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3357   -0.0831    2.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1101    0.0154    1.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5184    0.4072    1.3145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3960   -0.5911    0.6345 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6989   -0.1409    0.6103 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9657   -0.9792   -0.7373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5171   -1.3532   -0.8389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6168   -0.2498   -0.2549 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8820    0.9627   -1.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0237   -0.3851    0.4942 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0690   -0.1580    1.4857 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3365   -0.0564    0.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8808   -0.0001   -0.8065 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6056    0.9371   -1.5249 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5668    2.4732   -0.4271 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2356    2.4327   -1.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9886    2.1098    0.7008 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2273    1.2565   -2.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2360   -0.1093   -2.6709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3357   -0.3961   -2.3991 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7864   -1.6857   -1.9594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1801   -1.7631    0.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4107    1.0815    0.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6819    0.0683    2.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2675   -1.5455    2.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7495    0.1266    3.1541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7367    1.4554    1.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7836    0.3493    2.4124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3959   -1.5181    1.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7492    0.8399    0.5197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2484   -0.1869   -1.4880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5525   -1.8734   -1.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3311   -2.3228   -0.3793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2449   -1.4206   -1.9123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1266    1.7402   -1.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8463    1.3940   -0.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0646    0.6574   -2.1832 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0844   -1.4311    0.1173 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1560   -1.0667    2.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9405    0.6934    2.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9476    0.8195    0.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9209   -1.0002    0.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8857   -0.9945   -1.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5275    0.6014   -1.7043 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  6
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 17  2  1  0
 20  2  1  0
 15  5  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  1
  6 30  1  1
  7 31  1  0
  7 32  1  0
  8 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  1
 12 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  6
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  6
 21 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3beta,17beta)-Androst-5-ene-3,17-diol	ChEBI
3beta,17beta-Dihydroxy-5-androstene	ChEBI
3beta,17beta-Dihydroxyandrost-5-ene	ChEBI
5-Androstenediol	ChEBI
Androst-5-en-3beta,17beta-diol	ChEBI
Androst-5-enediol	ChEBI
Hermaphrodiol	ChEBI
Androst-5-ene-3beta,17beta-diol	Kegg
Tetrabol	Kegg
(3b,17b)-Androst-5-ene-3,17-diol	Generator
(3Β,17β)-androst-5-ene-3,17-diol	Generator
3b,17b-Dihydroxy-5-androstene	Generator
3Β,17β-dihydroxy-5-androstene	Generator
3b,17b-Dihydroxyandrost-5-ene	Generator
3Β,17β-dihydroxyandrost-5-ene	Generator
Androst-5-en-3b,17b-diol	Generator
Androst-5-en-3β,17β-diol	Generator
Androst-5-ene-3b,17b-diol	Generator
Androst-5-ene-3β,17β-diol	Generator
Androstenediol	ChEBI
Androst-5-ene-3,17-diol	HMDB
b,17b-Diol	HMDB
delta-5-Androstenediol	HMDB
Delta5-Androstenediol	HMDB
5 Androstene 3,17 diol	MeSH, HMDB
Delta 5-Androstenediol	MeSH, HMDB
Parke davis brand OF androstenediol	MeSH, HMDB
delta 5-Androstene-3 beta,17 beta-diol	MeSH, HMDB
5 Androstene 3beta 17beta diol	MeSH, HMDB
Androst 5 ene 3 beta,17 beta diol	MeSH, HMDB
Androst-5-ene-3 beta,17 beta-diol	MeSH, HMDB
5-Androstene-3beta-17beta-diol	MeSH, HMDB
Bisexovister	MeSH, HMDB
Delta 5 Androstenediol	MeSH, HMDB
5-Androstene-3,17-diol	MeSH, HMDB
Androst 5 ene 3,17 diol	MeSH, HMDB
delta 5 Androstene 3 beta,17 beta diol	MeSH, HMDB

Chemical Formula

C₁₉H₃₀O₂

Average Molecular Weight

290.4403

Monoisotopic Molecular Weight

290.224580204

IUPAC Name

(1S,2R,5S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,14-diol

Traditional Name

5-androstenediol

CAS Registry Number

521-17-5

SMILES

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

InChI Identifier

InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-17,20-21H,4-11H2,1-2H3/t13-,14-,15-,16-,17-,18-,19-/m0/s1

InChI Key

QADHLRWLCPCEKT-LOVVWNRFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Androstane steroids

Direct Parent

Androgens and derivatives

Alternative Parents

Substituents

Androgen-skeleton
17-hydroxysteroid
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Hydroxysteroid
3-hydroxysteroid
3-hydroxy-delta-5-steroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3beta-hydroxy steroid (CHEBI:2710 )
17beta-hydroxy steroid (CHEBI:2710 )
C19 steroids (androgens) and derivatives (C04295 )
Androstane and derivatives (C04295 )
C19 steroids (androgens) and derivatives (LMST02020005 )

Ontology

Not Available

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	0.055 g/L	ALOGPS
logP	3.42	ALOGPS
logP	2.8	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	18.2	ChemAxon
pKa (Strongest Basic)	-0.77	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	85.48 m³·mol⁻¹	ChemAxon
Polarizability	34.68 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]+	169.529	31661259
DarkChem	[M-H]-	164.976	31661259
DeepCCS	[M-2H]-	208.056	30932474
DeepCCS	[M+Na]+	182.582	30932474
AllCCS	[M+H]+	176.6	32859911
AllCCS	[M+H-H2O]+	173.5	32859911
AllCCS	[M+NH4]+	179.5	32859911
AllCCS	[M+Na]+	180.3	32859911
AllCCS	[M-H]-	178.8	32859911
AllCCS	[M+Na-2H]-	179.0	32859911
AllCCS	[M+HCOO]-	179.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Androstenediol	[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C	2471.0	Standard polar	33892256
5-Androstenediol	[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C	2497.1	Standard non polar	33892256
5-Androstenediol	[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C	2609.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Androstenediol,1TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@@]43C)[C@@H]1CC[C@@H]2O[Si](C)(C)C	2607.7	Semi standard non polar	33892256
5-Androstenediol,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]1CC[C@@H]2O	2601.2	Semi standard non polar	33892256
5-Androstenediol,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]1CC[C@@H]2O[Si](C)(C)C	2658.0	Semi standard non polar	33892256
5-Androstenediol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C	2891.1	Semi standard non polar	33892256
5-Androstenediol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CC[C@H](O)[C@@]4(C)CC[C@@H]32)C1	2871.3	Semi standard non polar	33892256
5-Androstenediol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]32)C1	3205.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 5-Androstenediol GC-MS (2 TMS)	splash10-004l-3920000000-6d05021a14366bfd40ba	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5-Androstenediol GC-MS (Non-derivatized)	splash10-004l-3920000000-6d05021a14366bfd40ba	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Androstenediol GC-MS (Non-derivatized) - 70eV, Positive	splash10-03ea-0190000000-3ceb1bf6f3d53ee5d7e5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Androstenediol GC-MS (2 TMS) - 70eV, Positive	splash10-014i-2126900000-1bc7293586fc53c1c457	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Androstenediol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Androstenediol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Androstenediol 10V, Positive-QTOF	splash10-00dl-0090000000-551d3445a2c6cdfa61ee	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Androstenediol 20V, Positive-QTOF	splash10-05fr-0390000000-5cfc4d0f79fea1c885b8	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Androstenediol 40V, Positive-QTOF	splash10-02bf-3890000000-e55a0a62bc36fe9049ec	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Androstenediol 10V, Negative-QTOF	splash10-000i-0090000000-d1deb080063b126f79ce	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Androstenediol 20V, Negative-QTOF	splash10-0079-0090000000-4d0bb4d4f197bc1e6846	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Androstenediol 40V, Negative-QTOF	splash10-0abc-1190000000-3f4cb9035ceae26a4876	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Androstenediol 10V, Positive-QTOF	splash10-0006-0090000000-9de0edc3a8b815dd7071	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Androstenediol 20V, Positive-QTOF	splash10-0abd-1940000000-90cd37c3652265920678	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Androstenediol 40V, Positive-QTOF	splash10-0aos-1900000000-76460d7bb552466d1504	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Androstenediol 10V, Negative-QTOF	splash10-000i-0090000000-c8c452fd99c6bb4f3631	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Androstenediol 20V, Negative-QTOF	splash10-000i-0090000000-1ce9bb01eb35f26908c4	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Androstenediol 40V, Negative-QTOF	splash10-000i-0090000000-aeda10893d01c46acf8c	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Adipose Tissue
Adrenal Cortex
Prostate
Skeletal Muscle
Testis

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

DB01524

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023228

KNApSAcK ID

Not Available

Chemspider ID

10188

KEGG Compound ID

C04295

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Androstenediol

METLIN ID

Not Available

PubChem Compound

10634

PDB ID

Not Available

ChEBI ID

2710

Food Biomarker Ontology

Not Available

VMH ID

C04295

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Ristovic, Lj.; Cobanovic, M.; Jovanovic, Z.; Orlic, M. Synthesis of androstenediol and determination of its physicochemical constants. Kemija u Industriji (1975), 24(7), 389-92.

Material Safety Data Sheet (MSDS)

Not Available

General References

Weusten JJ, Smals AG, Hofman JA, Kloppenborg PW, Benraad TJ: Early time sequence in pregnenolone metabolism to testosterone in homogenates of human and rat testis. Endocrinology. 1987 May;120(5):1909-13. [PubMed:3569120 ]
Leszczynski DE, Schafer RM: Characterization of steroid hormone association with human plasma lipoproteins. Steroids. 1989 Jul;54(1):37-53. [PubMed:2815156 ]
Szymczak J, Milewicz A, Thijssen JH, Blankenstein MA, Daroszewski J: Concentration of sex steroids in adipose tissue after menopause. Steroids. 1998 May-Jun;63(5-6):319-21. [PubMed:9618794 ]
Tchernof A, Despres JP, Belanger A, Dupont A, Prud'homme D, Moorjani S, Lupien PJ, Labrie F: Reduced testosterone and adrenal C19 steroid levels in obese men. Metabolism. 1995 Apr;44(4):513-9. [PubMed:7723675 ]
Vermeulen A, Deslypere JP: Intratesticular unconjugated steroids in elderly men. J Steroid Biochem. 1986 May;24(5):1079-83. [PubMed:2941625 ]
Anderson DC, Child DF, Sutcliffe CH, Buckley CH, Davies D, Longson D: Cushing's syndrome, nodular adrenal hyperplasia and virilizing carcinoma. Clin Endocrinol (Oxf). 1978 Jul;9(1):1-14. [PubMed:209918 ]
Dikkeschei LD, Wolthers BG, Willemse PH, van der Pol H, de Ruyter-Buitenhuis AW, Nagel GT: The determination of delta-5-androstenediol and its sulphate in serum and urine by gas chromatography-mass spectrometry. Clin Endocrinol (Oxf). 1993 Oct;39(4):469-74. [PubMed:8287574 ]
Bonney RC, Reed MJ, Beranek PA, James VH: Metabolism of adrenal androgens by human endometrium and adrenal cortex. J Steroid Biochem. 1985 Sep;23(3):347-52. [PubMed:2995729 ]
Mizokami A, Koh E, Fujita H, Maeda Y, Egawa M, Koshida K, Honma S, Keller ET, Namiki M: The adrenal androgen androstenediol is present in prostate cancer tissue after androgen deprivation therapy and activates mutated androgen receptor. Cancer Res. 2004 Jan 15;64(2):765-71. [PubMed:14744796 ]
Higashi T, Takayama N, Shimada K: Enzymic conversion of 3beta-hydroxy-5-ene-steroids and their sulfates to 3-oxo-4-ene-steroids for increasing sensitivity in LC-APCI-MS. J Pharm Biomed Anal. 2005 Sep 15;39(3-4):718-23. [PubMed:15905063 ]
Brown GA, Vukovich M, King DS: Testosterone prohormone supplements. Med Sci Sports Exerc. 2006 Aug;38(8):1451-61. [PubMed:16888459 ]
Mendonca BB, Bloise W, Arnhold IJ, Batista MC, Toledo SP, Drummond MC, Nicolau W, Mattar E: Male pseudohermaphroditism due to nonsalt-losing 3 beta-hydroxysteroid dehydrogenase deficiency: gender role change and absence of gynecomastia at puberty. J Steroid Biochem. 1987 Dec;28(6):669-75. [PubMed:2826919 ]
Brind JL: Direct radioimmunoassay of androstenediol-3-sulfate in the serum of normal men. Steroids. 1991 Jun;56(6):320-4. [PubMed:1926228 ]
Jones DL, James VH: The identification, quantification and possible origin of non-polar conjugates in human plasma. J Steroid Biochem. 1985 Feb;22(2):243-7. [PubMed:3157025 ]

Enzymes

Enzyme Details

1. 3-oxo-5-beta-steroid 4-dehydrogenase

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

Enzyme Details

2. 3-oxo-5-alpha-steroid 4-dehydrogenase 1

General function:: Involved in 3-oxo-5-alpha-steroid 4-dehydrogenase activity
Specific function:: Converts testosterone into 5-alpha-dihydrotestosterone and progesterone or corticosterone into their corresponding 5-alpha-3-oxosteroids. It plays a central role in sexual differentiation and androgen physiology.
Gene Name:: SRD5A1
Uniprot ID:: P18405
Molecular weight:: 29458.18

Enzyme Details

3. Testosterone 17-beta-dehydrogenase 3

General function:: Involved in oxidoreductase activity
Specific function:: Favors the reduction of androstenedione to testosterone. Uses NADPH while the two other EDH17B enzymes use NADH.
Gene Name:: HSD17B3
Uniprot ID:: P37058
Molecular weight:: 34515.345

Enzyme Details

4. Cytochrome P450 19A1

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:: CYP19A1
Uniprot ID:: P11511
Molecular weight:: 57882.48

Enzyme Details

5. 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

Testosterone + Hydrogen Ion + NADH → 5-Androstenediol + NAD	details

Enzyme Details

6. 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

Testosterone + Hydrogen Ion + NADH → 5-Androstenediol + NAD	details

Showing metabocard for 5-Androstenediol (HMDB0003818)

MOL for HMDB0003818 (5-Androstenediol)

3D MOL for HMDB0003818 (5-Androstenediol)

3D SDF for HMDB0003818 (5-Androstenediol)

3D-SDF for HMDB0003818 (5-Androstenediol)

PDB for HMDB0003818 (5-Androstenediol)

3D PDB for HMDB0003818 (5-Androstenediol)

SMILES for HMDB0003818 (5-Androstenediol)

INCHI for HMDB0003818 (5-Androstenediol)

Structure for HMDB0003818 (5-Androstenediol)

3D Structure for HMDB0003818 (5-Androstenediol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions