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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:11:38 UTC

Update Date

2021-09-26 22:55:02 UTC

HMDB ID

HMDB0246158

Secondary Accession Numbers

None

Metabolite Identification

Common Name

5alpha-Androstenone

Description

5alpha-Androstenone, also known as 5α-androstenone, 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. Based on a literature review a significant number of articles have been published on 5alpha-Androstenone. This compound has been identified in human blood as reported by (PMID: 31557052 ). 5alpha-androstenone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 5alpha-Androstenone is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0248398
     RDKit          3D
Androst-16-en-3-one
 48 51  0  0  0  0  0  0  0  0999 V2000
   -2.7555   -0.8241    1.5649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6454    0.2361    0.4909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0354    0.5784    0.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1961    0.6670   -1.2087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9020    0.3899   -1.8695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1003   -0.2977   -0.8059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6261   -0.0342   -0.9873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0453   -1.1189   -1.8261 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3987   -1.4027   -1.6022 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8332   -1.2941   -0.1660 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2677   -1.6515   -0.0400 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0826   -0.6393    0.6610 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2119   -0.4339    0.2934 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5159    0.1077    1.7962 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0549    0.4377    1.6324 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5095    0.1158    0.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0066    1.1415   -0.7148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0105    0.1321    0.3519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4823    1.4355    0.9485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9813    1.4899    0.9579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1629   -0.5819    2.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4438   -1.7930    1.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8117   -0.9427    1.9347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8347    0.7375    0.8130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1203    0.9047   -1.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0439   -0.2470   -2.7686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4677    1.3850   -2.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2822   -1.3955   -0.8518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5580    0.9608   -1.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6498   -2.0561   -1.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1675   -0.8307   -2.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5990   -2.4584   -1.9194 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0593   -0.7757   -2.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1788   -1.9967    0.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7315   -1.9415   -1.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3464   -2.5968    0.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5825   -0.5697    2.6912 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1392    1.0155    1.9742 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9627    1.5556    1.7580 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4192    0.0130    2.4396 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4697    1.0994   -1.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0677    0.9872   -0.9281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9120    2.1382   -0.2362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2917   -0.7414    0.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0655    1.5553    1.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0451    2.2461    0.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3083    2.3594    0.3526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3156    1.6817    1.9987 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
  6  2  1  0
 18  7  1  0
 20  2  1  0
 16 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
M  END

  Mrv0541 05061307472D          

 20 23  0  0  0  0            999 V2000
    2.1794    0.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3365    0.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8734    1.8884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1906    2.3514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3653    2.9114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4468    2.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9608    1.0193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4756    0.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6441    1.0959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2877    0.4384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1486    0.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7092    2.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8971    2.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2411    1.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7271    1.9903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5392    1.8451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1953    1.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8195    1.0691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6168    1.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0532    1.9404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  6  5  1  0  0  0  0
  9  3  2  0  0  0  0
 10  8  1  0  0  0  0
 11  7  1  0  0  0  0
 13  5  1  0  0  0  0
 13 12  1  0  0  0  0
 14  7  1  0  0  0  0
 14 12  1  0  0  0  0
 15  6  1  0  0  0  0
 16  4  1  0  0  0  0
 16 15  1  0  0  0  0
 17  8  1  0  0  0  0
 17 15  1  0  0  0  0
 18  1  1  0  0  0  0
 18  9  1  0  0  0  0
 18 10  1  0  0  0  0
 18 16  1  0  0  0  0
 19  2  1  0  0  0  0
 19 11  1  0  0  0  0
 19 13  1  0  0  0  0
 19 17  1  0  0  0  0
 20 14  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0246158

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12CCC3C(CCC4CC(=O)CCC34C)C1CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C19H28O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,9,13,15-17H,4-8,10-12H2,1-2H3

> <INCHI_KEY>
HFVMLYAGWXSTQI-UHFFFAOYSA-N

> <FORMULA>
C19H28O

> <MOLECULAR_WEIGHT>
272.425

> <EXACT_MASS>
272.214015518

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
32.86380914314622

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-13-en-5-one

> <ALOGPS_LOGP>
4.62

> <JCHEM_LOGP>
4.280147043

> <ALOGPS_LOGS>
-6.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.352808751886174

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
83.20419999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.14e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-13-en-5-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0248398
     RDKit          3D
Androst-16-en-3-one
 48 51  0  0  0  0  0  0  0  0999 V2000
   -2.7555   -0.8241    1.5649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6454    0.2361    0.4909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0354    0.5784    0.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1961    0.6670   -1.2087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9020    0.3899   -1.8695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1003   -0.2977   -0.8059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6261   -0.0342   -0.9873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0453   -1.1189   -1.8261 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3987   -1.4027   -1.6022 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8332   -1.2941   -0.1660 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2677   -1.6515   -0.0400 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0826   -0.6393    0.6610 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2119   -0.4339    0.2934 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5159    0.1077    1.7962 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0549    0.4377    1.6324 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5095    0.1158    0.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0066    1.1415   -0.7148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0105    0.1321    0.3519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4823    1.4355    0.9485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9813    1.4899    0.9579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1629   -0.5819    2.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4438   -1.7930    1.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8117   -0.9427    1.9347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8347    0.7375    0.8130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1203    0.9047   -1.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0439   -0.2470   -2.7686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4677    1.3850   -2.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2822   -1.3955   -0.8518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5580    0.9608   -1.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6498   -2.0561   -1.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1675   -0.8307   -2.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5990   -2.4584   -1.9194 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0593   -0.7757   -2.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1788   -1.9967    0.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7315   -1.9415   -1.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3464   -2.5968    0.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5825   -0.5697    2.6912 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1392    1.0155    1.9742 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9627    1.5556    1.7580 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4192    0.0130    2.4396 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4697    1.0994   -1.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0677    0.9872   -0.9281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9120    2.1382   -0.2362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2917   -0.7414    0.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0655    1.5553    1.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0451    2.2461    0.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3083    2.3594    0.3526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3156    1.6817    1.9987 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
  6  2  1  0
 18  7  1  0
 20  2  1  0
 16 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       4.068   0.610   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.628   1.361   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.364   3.525   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.089   4.389   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.682   5.435   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.834   5.164   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.660   1.903   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.888   1.089   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.936   2.046   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.404   0.818   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.144   1.632   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.191   4.528   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.675   4.257   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.183   3.351   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.357   3.715   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.873   3.444   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.365   2.538   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.396   1.996   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.151   2.809   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -5.699   3.622   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2   19                                                            
CONECT    3    4    9                                                       
CONECT    4    3   16                                                       
CONECT    5    6   13                                                       
CONECT    6    5   15                                                       
CONECT    7   11   14                                                       
CONECT    8   10   17                                                       
CONECT    9    3   18                                                       
CONECT   10    8   18                                                       
CONECT   11    7   19                                                       
CONECT   12   13   14                                                       
CONECT   13    5   12   19                                                  
CONECT   14    7   12   20                                                  
CONECT   15    6   16   17                                                  
CONECT   16    4   15   18                                                  
CONECT   17    8   15   19                                                  
CONECT   18    1    9   10   16                                             
CONECT   19    2   11   13   17                                             
CONECT   20   14                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

COMPND    HMDB0246158
HETATM    1  C1  UNL     1       2.519   2.000   0.618  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.481   0.757  -0.239  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.905   0.431  -0.556  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.089  -0.879  -0.536  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.816  -1.561  -0.207  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.045  -0.465   0.511  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.594  -0.725   0.508  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.037  -0.744   1.940  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.368  -1.260   1.966  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.219  -0.954   0.811  1.00  0.00           C  
HETATM   11  C11 UNL     1      -3.333  -0.008   1.284  1.00  0.00           C  
HETATM   12  C12 UNL     1      -3.023   1.382   0.904  1.00  0.00           C  
HETATM   13  O1  UNL     1      -2.876   2.247   1.726  1.00  0.00           O  
HETATM   14  C13 UNL     1      -2.896   1.682  -0.534  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.517   0.424  -1.262  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.584  -0.464  -0.431  1.00  0.00           C  
HETATM   17  C16 UNL     1      -1.280  -1.669  -1.324  1.00  0.00           C  
HETATM   18  C17 UNL     1      -0.255   0.261  -0.212  1.00  0.00           C  
HETATM   19  C18 UNL     1       0.285   0.798  -1.473  1.00  0.00           C  
HETATM   20  C19 UNL     1       1.767   0.959  -1.540  1.00  0.00           C  
HETATM   21  H1  UNL     1       2.768   2.848  -0.028  1.00  0.00           H  
HETATM   22  H2  UNL     1       3.356   1.878   1.354  1.00  0.00           H  
HETATM   23  H3  UNL     1       1.591   2.138   1.203  1.00  0.00           H  
HETATM   24  H4  UNL     1       4.696   1.139  -0.774  1.00  0.00           H  
HETATM   25  H5  UNL     1       5.013  -1.447  -0.725  1.00  0.00           H  
HETATM   26  H6  UNL     1       2.256  -1.786  -1.155  1.00  0.00           H  
HETATM   27  H7  UNL     1       2.931  -2.462   0.399  1.00  0.00           H  
HETATM   28  H8  UNL     1       2.400  -0.376   1.564  1.00  0.00           H  
HETATM   29  H9  UNL     1       0.435  -1.790   0.164  1.00  0.00           H  
HETATM   30  H10 UNL     1       0.141   0.281   2.357  1.00  0.00           H  
HETATM   31  H11 UNL     1       0.739  -1.385   2.513  1.00  0.00           H  
HETATM   32  H12 UNL     1      -1.809  -0.890   2.940  1.00  0.00           H  
HETATM   33  H13 UNL     1      -1.285  -2.373   2.135  1.00  0.00           H  
HETATM   34  H14 UNL     1      -2.796  -1.892   0.543  1.00  0.00           H  
HETATM   35  H15 UNL     1      -4.315  -0.270   0.819  1.00  0.00           H  
HETATM   36  H16 UNL     1      -3.424  -0.062   2.403  1.00  0.00           H  
HETATM   37  H17 UNL     1      -3.933   1.960  -0.888  1.00  0.00           H  
HETATM   38  H18 UNL     1      -2.270   2.547  -0.753  1.00  0.00           H  
HETATM   39  H19 UNL     1      -2.092   0.593  -2.257  1.00  0.00           H  
HETATM   40  H20 UNL     1      -3.440  -0.178  -1.402  1.00  0.00           H  
HETATM   41  H21 UNL     1      -0.280  -1.658  -1.740  1.00  0.00           H  
HETATM   42  H22 UNL     1      -2.013  -1.770  -2.146  1.00  0.00           H  
HETATM   43  H23 UNL     1      -1.380  -2.622  -0.728  1.00  0.00           H  
HETATM   44  H24 UNL     1      -0.510   1.114   0.482  1.00  0.00           H  
HETATM   45  H25 UNL     1      -0.152   1.833  -1.617  1.00  0.00           H  
HETATM   46  H26 UNL     1      -0.081   0.259  -2.398  1.00  0.00           H  
HETATM   47  H27 UNL     1       2.095   1.944  -1.939  1.00  0.00           H  
HETATM   48  H28 UNL     1       2.170   0.214  -2.282  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    6   20
CONECT    3    4    4   24
CONECT    4    5   25
CONECT    5    6   26   27
CONECT    6    7   28
CONECT    7    8   18   29
CONECT    8    9   30   31
CONECT    9   10   32   33
CONECT   10   11   16   34
CONECT   11   12   35   36
CONECT   12   13   13   14
CONECT   14   15   37   38
CONECT   15   16   39   40
CONECT   16   17   18
CONECT   17   41   42   43
CONECT   18   19   44
CONECT   19   20   45   46
CONECT   20   47   48
END

HMDB0248398
     RDKit          3D
Androst-16-en-3-one
 48 51  0  0  0  0  0  0  0  0999 V2000
   -2.7555   -0.8241    1.5649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6454    0.2361    0.4909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0354    0.5784    0.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1961    0.6670   -1.2087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9020    0.3899   -1.8695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1003   -0.2977   -0.8059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6261   -0.0342   -0.9873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0453   -1.1189   -1.8261 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3987   -1.4027   -1.6022 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8332   -1.2941   -0.1660 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2677   -1.6515   -0.0400 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0826   -0.6393    0.6610 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2119   -0.4339    0.2934 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5159    0.1077    1.7962 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0549    0.4377    1.6324 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5095    0.1158    0.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0066    1.1415   -0.7148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0105    0.1321    0.3519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4823    1.4355    0.9485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9813    1.4899    0.9579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1629   -0.5819    2.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4438   -1.7930    1.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8117   -0.9427    1.9347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8347    0.7375    0.8130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1203    0.9047   -1.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0439   -0.2470   -2.7686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4677    1.3850   -2.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2822   -1.3955   -0.8518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5580    0.9608   -1.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6498   -2.0561   -1.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1675   -0.8307   -2.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5990   -2.4584   -1.9194 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0593   -0.7757   -2.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1788   -1.9967    0.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7315   -1.9415   -1.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3464   -2.5968    0.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5825   -0.5697    2.6912 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1392    1.0155    1.9742 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9627    1.5556    1.7580 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4192    0.0130    2.4396 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4697    1.0994   -1.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0677    0.9872   -0.9281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9120    2.1382   -0.2362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2917   -0.7414    0.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0655    1.5553    1.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0451    2.2461    0.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3083    2.3594    0.3526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3156    1.6817    1.9987 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
  6  2  1  0
 18  7  1  0
 20  2  1  0
 16 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5a-Androstenone	Generator
5Α-androstenone	Generator
(5alpha)-Androst-16-en-3-one	HMDB
16-(5alpha)Androsten-3-one	HMDB
3-keto-5alpha,16-Androstene	HMDB
Androst-16-en-3-one	HMDB
Androstenone	HMDB
5alpha-Androst-16-en-3-one	MeSH
5 alpha-Androst-16-en-3-one	MeSH
AEON steroid	MeSH
Androst-16-en-3-one, (5beta)-isomer	MeSH
5a-Androst-16-en-3-one	Generator
5Α-androst-16-en-3-one	Generator

Chemical Formula

C₁₉H₂₈O

Average Molecular Weight

272.425

Monoisotopic Molecular Weight

272.214015518

IUPAC Name

2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-13-en-5-one

Traditional Name

2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-13-en-5-one

CAS Registry Number

Not Available

SMILES

CC12CCC3C(CCC4CC(=O)CCC34C)C1CC=C2

InChI Identifier

InChI=1S/C19H28O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,9,13,15-17H,4-8,10-12H2,1-2H3

InChI Key

HFVMLYAGWXSTQI-UHFFFAOYSA-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
Oxosteroid
3-oxosteroid
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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
logP	4.62	ALOGPS
logP	4.28	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	83.2 m³·mol⁻¹	ChemAxon
Polarizability	32.86 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	200.923	30932474
DeepCCS	[M+Na]+	176.488	30932474
AllCCS	[M+H]+	170.2	32859911
AllCCS	[M+H-H2O]+	166.9	32859911
AllCCS	[M+NH4]+	173.3	32859911
AllCCS	[M+Na]+	174.2	32859911
AllCCS	[M-H]-	176.7	32859911
AllCCS	[M+Na-2H]-	176.8	32859911
AllCCS	[M+HCOO]-	176.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5alpha-Androstenone	CC12CCC3C(CCC4CC(=O)CCC34C)C1CC=C2	2511.4	Standard polar	33892256
5alpha-Androstenone	CC12CCC3C(CCC4CC(=O)CCC34C)C1CC=C2	2264.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5alpha-Androstenone,1TMS,isomer #1	CC12C=CCC1C1CCC3CC(O[Si](C)(C)C)=CCC3(C)C1CC2	2370.2	Semi standard non polar	33892256
5alpha-Androstenone,1TMS,isomer #1	CC12C=CCC1C1CCC3CC(O[Si](C)(C)C)=CCC3(C)C1CC2	2193.9	Standard non polar	33892256
5alpha-Androstenone,1TMS,isomer #1	CC12C=CCC1C1CCC3CC(O[Si](C)(C)C)=CCC3(C)C1CC2	2706.7	Standard polar	33892256
5alpha-Androstenone,1TMS,isomer #2	CC12C=CCC1C1CCC3C=C(O[Si](C)(C)C)CCC3(C)C1CC2	2379.9	Semi standard non polar	33892256
5alpha-Androstenone,1TMS,isomer #2	CC12C=CCC1C1CCC3C=C(O[Si](C)(C)C)CCC3(C)C1CC2	2217.3	Standard non polar	33892256
5alpha-Androstenone,1TMS,isomer #2	CC12C=CCC1C1CCC3C=C(O[Si](C)(C)C)CCC3(C)C1CC2	2702.2	Standard polar	33892256
5alpha-Androstenone,1TBDMS,isomer #1	CC12C=CCC1C1CCC3CC(O[Si](C)(C)C(C)(C)C)=CCC3(C)C1CC2	2625.4	Semi standard non polar	33892256
5alpha-Androstenone,1TBDMS,isomer #1	CC12C=CCC1C1CCC3CC(O[Si](C)(C)C(C)(C)C)=CCC3(C)C1CC2	2401.9	Standard non polar	33892256
5alpha-Androstenone,1TBDMS,isomer #1	CC12C=CCC1C1CCC3CC(O[Si](C)(C)C(C)(C)C)=CCC3(C)C1CC2	2874.0	Standard polar	33892256
5alpha-Androstenone,1TBDMS,isomer #2	CC12C=CCC1C1CCC3C=C(O[Si](C)(C)C(C)(C)C)CCC3(C)C1CC2	2629.5	Semi standard non polar	33892256
5alpha-Androstenone,1TBDMS,isomer #2	CC12C=CCC1C1CCC3C=C(O[Si](C)(C)C(C)(C)C)CCC3(C)C1CC2	2440.3	Standard non polar	33892256
5alpha-Androstenone,1TBDMS,isomer #2	CC12C=CCC1C1CCC3C=C(O[Si](C)(C)C(C)(C)C)CCC3(C)C1CC2	2869.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5alpha-Androstenone GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-0290000000-c34aa5054883b3ad13e6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5alpha-Androstenone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5alpha-Androstenone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5alpha-Androstenone 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 - 5alpha-Androstenone 10V, Positive-QTOF	splash10-00di-0090000000-574fd253156e121ac144	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5alpha-Androstenone 20V, Positive-QTOF	splash10-05fs-1290000000-172e066e35f7e2baa99f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5alpha-Androstenone 40V, Positive-QTOF	splash10-05r1-3390000000-2d9bdf5fda43f59c8799	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5alpha-Androstenone 10V, Negative-QTOF	splash10-00di-0090000000-304bb54718cd6d863ae8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5alpha-Androstenone 20V, Negative-QTOF	splash10-00di-0090000000-32310c65098512441667	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5alpha-Androstenone 40V, Negative-QTOF	splash10-052f-3090000000-e87d431cebc617fdf93d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5alpha-Androstenone 10V, Positive-QTOF	splash10-00di-0090000000-3a6e962fc715b278f2ef	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5alpha-Androstenone 20V, Positive-QTOF	splash10-0ac1-1690000000-5ae3fcb24c1f192a2d9a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5alpha-Androstenone 40V, Positive-QTOF	splash10-0536-9500000000-8c58bc20cd3b71173cdf	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5alpha-Androstenone 10V, Negative-QTOF	splash10-00di-0090000000-c4728b358ec3c0d7d18c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5alpha-Androstenone 20V, Negative-QTOF	splash10-00di-0090000000-c4728b358ec3c0d7d18c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5alpha-Androstenone 40V, Negative-QTOF	splash10-01b9-0190000000-6f1fcb32aa48f1b823fd	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012796

KNApSAcK ID

Not Available

Chemspider ID

78208

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Androstenone

METLIN ID

Not Available

PubChem Compound

86705

PDB ID

Not Available

ChEBI ID

37894

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 5alpha-Androstenone (HMDB0246158)

MOL for HMDB0246158 (5alpha-Androstenone)

3D MOL for HMDB0246158 (5alpha-Androstenone)

3D SDF for HMDB0246158 (5alpha-Androstenone)

3D-SDF for HMDB0246158 (5alpha-Androstenone)

PDB for HMDB0246158 (5alpha-Androstenone)

3D PDB for HMDB0246158 (5alpha-Androstenone)

SMILES for HMDB0246158 (5alpha-Androstenone)

INCHI for HMDB0246158 (5alpha-Androstenone)

Structure for HMDB0246158 (5alpha-Androstenone)

3D Structure for HMDB0246158 (5alpha-Androstenone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra