NP-MRD: Showing NP-Card for Androst-5-ene-3beta,17beta-diol (NP0087081)

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Record Information

Version

2.0

Created at

2022-05-11 16:39:29 UTC

Updated at

2022-05-11 16:39:29 UTC

NP-MRD ID

NP0087081

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Androst-5-ene-3beta,17beta-diol

Description

5-Androstenediol, also known as hermaphrodiol or tetrabol, 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, 5-androstenediol is considered to be a steroid lipid molecule. 5-Androstenediol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 5-Androstenediol exists in all living organisms, ranging from bacteria to humans. Androst-5-ene-3beta,17beta-diol is found in Homo sapiens and Mus musculus. Androst-5-ene-3beta,17beta-diol was first documented in 1978 (PMID: 209918). A 3beta-hydroxy steroid that is 3beta-hydroxyandrost-5-ene carrying an additional hydroxy group at position 17beta (PMID: 9618794) (PMID: 7723675) (PMID: 2941625) (PMID: 8287574).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 51 54  0  0  0  0  0  0  0  0999 V2000
   -2.2942    1.6513   -0.5641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5329    0.4373    0.2634 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9257    0.6037    1.6092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4452    0.7355    1.5002 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2155   -0.2863    0.6334 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5173   -0.5791   -0.6429 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1008   -1.8639   -1.2134 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5732   -1.8610   -1.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2642   -0.9675   -0.4200 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7391   -1.0758   -0.3689 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4156    0.1127    0.2251 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6147    1.0784   -0.7829 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7869    0.6707    1.4554 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3250    0.4314    1.6065 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6099    0.1626    0.2969 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6085    1.3696   -0.5952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9312   -0.8324   -0.3285 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8534   -1.0955   -1.4545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1902   -1.0302   -0.7396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9906    0.0664    0.2851 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7598    1.1509   -0.1259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2601    2.1886   -0.6901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9654    1.4182   -1.6093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6237    2.3862   -0.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3101    1.5329    2.0976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1586   -0.2672    2.2597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1973    1.7772    1.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0304    0.5846    2.5417 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2869   -1.2511    1.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3633    0.1766   -1.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3525   -2.7562   -0.7016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1948   -1.9119   -2.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1081   -2.6565   -1.5841 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0684   -2.0309    0.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0820   -1.1464   -1.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4506   -0.2243    0.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8630    1.9371   -0.3408 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2824    0.3221    2.3889 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9689    1.7803    1.4379 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1048   -0.4121    2.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8546    1.3257    2.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9975    1.1682   -1.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6046    1.8216   -0.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2018    2.1702   -0.0694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0136   -1.6305    0.4247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8615   -0.3098   -2.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7051   -2.0987   -1.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0261   -0.8253   -1.4324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3265   -2.0022   -0.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3427   -0.2278    1.2901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9546    1.1259   -1.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20  2  1  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  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
  2 17  1  0
 15  5  1  0
  6 17  1  0
 15  9  1  0
 17 45  1  1
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  1
 21 51  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  1
  6 30  1  6
  7 31  1  0
  7 32  1  0
  8 33  1  0
 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
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>
NP0087081

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

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

View in JSmol

Synonyms

Value	Source
(3beta,17beta)-Androst-5-ene-3,17-diol	ChEBI
3beta,17beta-Dihydroxy-5-androstene	ChEBI
3beta,17beta-Dihydroxyandrost-5-ene	ChEBI
Androst-5-en-3beta,17beta-diol	ChEBI
Androst-5-enediol	ChEBI
Androstenediol	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
Androst-5-ene-3,17-diol	HMDB
b,17b-Diol	HMDB
delta-5-Androstenediol	HMDB
Delta5-Androstenediol	HMDB
5 Androstene 3,17 diol	HMDB
Delta 5-Androstenediol	HMDB
Parke davis brand OF androstenediol	HMDB
delta 5-Androstene-3 beta,17 beta-diol	HMDB
5 Androstene 3beta 17beta diol	HMDB
Androst 5 ene 3 beta,17 beta diol	HMDB
Androst-5-ene-3 beta,17 beta-diol	HMDB
5-Androstene-3beta-17beta-diol	HMDB
Bisexovister	HMDB
Delta 5 Androstenediol	HMDB
5-Androstene-3,17-diol	HMDB
Androst 5 ene 3,17 diol	HMDB
delta 5 Androstene 3 beta,17 beta diol	HMDB

Chemical Formula

C₁₉H₃₀O₂

Average Mass

290.4403 Da

Monoisotopic Mass

290.22458 Da

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

Not Available

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Homo sapiens	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Mus musculus	LOTUS Database	35616633
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
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

External Links

HMDB ID

HMDB0003818

DrugBank ID

DB01524

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023228

KNApSAcK ID

Not Available

Chemspider ID

10188

KEGG Compound ID

C04295

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

5-Androstenediol

METLIN ID

6983

PubChem Compound

10634

PDB ID

Not Available

ChEBI ID

2710

Good Scents ID

Not Available

References

General References

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. doi: 10.1016/s0039-128x(98)00019-1. [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. doi: 10.1016/0026-0495(95)90060-8. [PubMed:7723675 ]
Vermeulen A, Deslypere JP: Intratesticular unconjugated steroids in elderly men. J Steroid Biochem. 1986 May;24(5):1079-83. doi: 10.1016/0022-4731(86)90363-8. [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. doi: 10.1111/j.1365-2265.1978.tb03567.x. [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. doi: 10.1111/j.1365-2265.1993.tb02395.x. [PubMed:8287574 ]

Showing NP-Card for Androst-5-ene-3beta,17beta-diol (NP0087081)

MOL for NP0087081 (Androst-5-ene-3beta,17beta-diol)

3D MOL for NP0087081 (Androst-5-ene-3beta,17beta-diol)

3D SDF for NP0087081 (Androst-5-ene-3beta,17beta-diol)

3D-SDF for NP0087081 (Androst-5-ene-3beta,17beta-diol)

PDB for NP0087081 (Androst-5-ene-3beta,17beta-diol)

3D PDB for NP0087081 (Androst-5-ene-3beta,17beta-diol)

SMILES for NP0087081 (Androst-5-ene-3beta,17beta-diol)

INCHI for NP0087081 (Androst-5-ene-3beta,17beta-diol)

Structure for NP0087081 (Androst-5-ene-3beta,17beta-diol)

3D Structure for NP0087081 (Androst-5-ene-3beta,17beta-diol)