NP-MRD: Showing NP-Card for 4-Androstenediol (NP0087423)

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Record Information

Version

2.0

Created at

2022-05-11 16:49:17 UTC

Updated at

2022-05-11 16:49:17 UTC

NP-MRD ID

NP0087423

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-Androstenediol

Description

4-Androstenediol 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, 4-androstenediol is considered to be a steroid lipid molecule. There is also some conversion into estrogen, since testosterone is the metabolic precursor of the estrogens.4-Androstenediol is closer to testosterone structurally than 5-androstenediol, and has androgenic effects, acting as a weak partial agonist of the androgen receptor. Patrick Arnold holds a 1999 patent on "Use of 4-androstenediol to increase testosterone levels in humans". 4-Androstenediol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. However, due to its lower intrinsic activity in comparison, in the presence of full agonists like testosterone or dihydrotestosterone (DHT), 4-androstenediol has antagonistic actions, behaving more like an antiandrogen.4-Androstenediol is very weakly estrogenic. The conversion rate is about 15.76%, Almost triple that of 4-androstenedione, due to utilization of a different enzymatic pathway. 4-Androstenediol is found in Homo sapiens and Mus musculus. 4-Androstenediol was first documented in 2004 (PMID: 15370836). It has approximately 0.5% And 0.6% Of the affinity of estradiol at the ERα and ERβ, respectively.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 51 54  0  0  0  0  0  0  0  0999 V2000
   -2.3369   -0.9843   -1.8411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3809    0.2003   -0.9443 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5020    1.3269   -1.4214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0931    0.7695   -1.4495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3355    0.4654   -0.0589 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5605   -0.5444    0.6268 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2178   -0.8190    2.0324 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2017   -0.7072    2.4364 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0984   -0.0802    1.4586 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2029    0.4998    1.9134 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1882    1.1677    1.0222 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4510    1.1935    1.5780 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1477    0.4424   -0.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7213    0.6509   -0.8347 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7343   -0.1196    0.0036 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7442   -1.5530   -0.4872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9690   -0.0871    0.4825 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0283   -1.0288    0.9168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2864   -0.4640    0.2552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8179    0.5911   -0.7337 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5642    0.5840   -1.9002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6675   -1.7881   -1.5546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0039   -0.6286   -2.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3603   -1.4489   -1.9520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8036    1.6962   -2.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5373    2.1426   -0.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5501    1.5343   -1.8847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0467   -0.1425   -2.0940 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3394    1.4097    0.5190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4410   -1.4972    0.0458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5902   -1.8463    2.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8295   -0.1285    2.6817 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2954   -0.1691    3.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6342   -1.7282    2.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4447    0.5139    2.9855 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7856    2.1946    0.8316 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7092    2.1487    1.6723 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8186    0.9365   -1.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3789   -0.6346   -0.2089 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7241    0.2565   -1.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5579    1.7452   -0.8104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917   -1.7785   -0.7895 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1247   -1.6729   -1.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5032   -2.2714    0.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1232    0.8776    1.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8187   -2.0320    0.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1710   -1.0715    2.0157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8283   -1.2522   -0.3025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9306   -0.0004    1.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8182    1.5806   -0.2356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7558    1.5508   -2.1121 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  1  0
  9 10  2  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
  8 34  1  0
 10 35  1  0
 11 36  1  6
 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


  Mrv1652310041922032D          

 24 27  0  0  0  0            999 V2000
 9999.306610000.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.447910001.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4479 9998.9596    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1658 9998.1238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.733710000.1945    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.0216 9998.9596    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.734510001.0246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.020010000.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0200 9999.7870    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.7345 9999.3746    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.0206 9998.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7351 9998.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5935 9999.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8790 9999.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8790 9998.5410    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.5935 9998.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3080 9998.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3080 9999.3661    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.233610000.8671    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.449010000.6121    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.4490 9999.7871    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.2336 9999.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.718510000.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.488510001.6517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 13 18  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
  9  6  1  6  0  0  0
 12 10  1  0  0  0  0
 10  5  1  1  0  0  0
 15  4  1  1  0  0  0
 18  1  1  1  0  0  0
  9 18  1  0  0  0  0
 17 11  1  0  0  0  0
 19 20  1  0  0  0  0
 19 23  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 24  1  1  0  0  0
 10 21  1  0  0  0  0
 21  3  1  6  0  0  0
  7 20  1  0  0  0  0
 20  2  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0087423

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=C[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/h11,13-17,20-21H,3-10H2,1-2H3/t13-,14-,15-,16-,17-,18-,19-/m0/s1

> <INCHI_KEY>
BTTWKVFKBPAFDK-LOVVWNRFSA-N

> <FORMULA>
C19H30O2

> <MOLECULAR_WEIGHT>
290.4403

> <EXACT_MASS>
290.224580204

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
34.37828684998394

> <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[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-diol

> <ALOGPS_LOGP>
3.10

> <JCHEM_LOGP>
2.954084809666667

> <ALOGPS_LOGS>
-3.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.37770520810813

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.504415926529536

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8227000810590906

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
85.3272

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.81e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-OCT-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-OCT-19         0                                  
HETATM    1  C   UNK     0    8665.3728667.030   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8669.3698669.361   0.000  0.00  0.00           C+0
HETATM    3  H   UNK     0    8669.3698664.725   0.000  0.00  0.00           H+0
HETATM    4  O   UNK     0    8661.3768663.164   0.000  0.00  0.00           O+0
HETATM    5  H   UNK     0    8668.0368667.030   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8666.7078664.725   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0    8668.0388668.579   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8666.7048667.809   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8666.7048666.269   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8668.0388665.499   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8666.7058663.173   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8668.0398663.943   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8664.0418666.253   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8662.7078665.483   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8662.7078663.943   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8664.0418663.173   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8665.3758663.943   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8665.3758665.483   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8670.8368668.285   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8669.3718667.809   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8669.3718666.269   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8670.8368665.793   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8671.7418667.039   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0    8671.3128669.750   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2   20                                                            
CONECT    3   21                                                            
CONECT    4   15                                                            
CONECT    5   10                                                            
CONECT    6    9                                                            
CONECT    7    8   20                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10    6   18                                             
CONECT   10    9   12    5   21                                             
CONECT   11   12   17                                                       
CONECT   12   11   10                                                       
CONECT   13   14   18                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16    4                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   11                                                  
CONECT   18   13   17    1    9                                             
CONECT   19   20   23   24                                                  
CONECT   20   19   21    7    2                                             
CONECT   21   20   22   10    3                                             
CONECT   22   21   23                                                       
CONECT   23   19   22                                                       
CONECT   24   19                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Value	Source
Androst-4-ene-3beta,17beta-diol	Kegg
Androst-4-ene-3b,17b-diol	Generator
Androst-4-ene-3β,17β-diol	Generator
(3b,17b)-Androst-4-ene-3,17-diol	HMDB
3b,17b-Dihydroxy-4-androstene	HMDB
4-Androstene-3b,17b-diol	HMDB
Androst-4-en-3b,17b-diol	HMDB
D4-Androstene-3b,17b-diol	HMDB
(3beta,17beta)-Androst-4-ene-3,17-diol	HMDB
(3Β,17β)-androst-4-ene-3,17-diol	HMDB
3beta,17beta-Dihydroxy-4-androstene	HMDB
3Β,17β-dihydroxy-4-androstene	HMDB
4-Androstenediol	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[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-diol

Traditional Name

(1S,2R,5S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-diol

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=C[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/h11,13-17,20-21H,3-10H2,1-2H3/t13-,14-,15-,16-,17-,18-,19-/m0/s1

InChI Key

BTTWKVFKBPAFDK-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
Hydroxysteroid
3-hydroxysteroid
3-hydroxy-delta-4-steroid
Delta-4-steroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-hydroxy steroid (CHEBI:34386 )
Androstane and derivatives (C14210 )
C19 steroids (androgens) and derivatives (LMST02020105 )

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	3.1	ALOGPS
logP	2.95	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	17.5	ChemAxon
pKa (Strongest Basic)	-0.82	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	85.33 m³·mol⁻¹	ChemAxon
Polarizability	34.38 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

HMDB0005849

DrugBank ID

DB01526

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023781

KNApSAcK ID

Not Available

Chemspider ID

120071

KEGG Compound ID

C14210

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

4-Androstenediol

METLIN ID

Not Available

PubChem Compound

136297

PDB ID

Not Available

ChEBI ID

34386

Good Scents ID

Not Available

References

General References

Parr MK, Geyer H, Reinhart U, Schanzer W: Analytical strategies for the detection of non-labelled anabolic androgenic steroids in nutritional supplements. Food Addit Contam. 2004 Jul;21(7):632-40. doi: 10.1080/02652030410001701602. [PubMed:15370836 ]

Showing NP-Card for 4-Androstenediol (NP0087423)

MOL for NP0087423 (4-Androstenediol)

3D MOL for NP0087423 (4-Androstenediol)

3D SDF for NP0087423 (4-Androstenediol)

3D-SDF for NP0087423 (4-Androstenediol)

PDB for NP0087423 (4-Androstenediol)

3D PDB for NP0087423 (4-Androstenediol)

SMILES for NP0087423 (4-Androstenediol)

INCHI for NP0087423 (4-Androstenediol)

Structure for NP0087423 (4-Androstenediol)

3D Structure for NP0087423 (4-Androstenediol)