NP-MRD: Showing NP-Card for 5β-dihydrotestosterone (NP0257891)

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Record Information

Version

2.0

Created at

2022-09-07 23:09:27 UTC

Updated at

2022-09-07 23:09:27 UTC

NP-MRD ID

NP0257891

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5β-dihydrotestosterone

Description

5B-Dihydrotestosterone, also known as 5-beta-DHT or 5-Β-DHT, 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, 5b-dihydrotestosterone is considered to be a steroid lipid molecule. 5B-Dihydrotestosterone is a drug. 5B-Dihydrotestosterone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 5B-dihydrotestosterone can be converted into testosterone; which is catalyzed by the enzyme 3-oxo-5-beta-steroid 4-dehydrogenase. 5β-dihydrotestosterone is found in Mus musculus. 5β-dihydrotestosterone was first documented in 1977 (PMID: 591837). In humans, 5b-dihydrotestosterone is involved in androgen and estrogen metabolism (PMID: 10357254) (PMID: 11430920) (PMID: 15758151) (PMID: 17804019) (PMID: 18276759) (PMID: 19215525).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231220512D          

 25 28  0  0  1  0            999 V2000
   20.0052   -3.2205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5192   -6.7741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2539   -5.4935    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.5394   -5.0810    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.9683   -5.0810    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.9683   -4.2561    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.7887   -5.4991    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.7820   -6.3584    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.5394   -4.2561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2539   -3.8436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2671   -6.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7489   -5.3324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7489   -4.0046    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.5262   -6.7881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2303   -4.6686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0241   -5.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9683   -3.4311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7950   -4.6741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0104   -6.8119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2421   -5.4693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2352   -6.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2642   -4.5816    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.5473   -5.9060    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.0793   -5.9023    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.7846   -7.0184    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 13  1  1  1  0  0  0
  2 21  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3 11  1  0  0  0  0
  3 22  1  1  0  0  0
  4  7  1  0  0  0  0
  4  9  1  0  0  0  0
  4 23  1  6  0  0  0
  5  6  1  0  0  0  0
  5 12  1  0  0  0  0
  5 24  1  6  0  0  0
  6 10  1  0  0  0  0
  6 13  1  0  0  0  0
  6 17  1  1  0  0  0
  7  8  1  0  0  0  0
  7 16  1  0  0  0  0
  7 18  1  1  0  0  0
  8 14  1  0  0  0  0
  8 19  1  0  0  0  0
  8 25  1  1  0  0  0
  9 10  1  0  0  0  0
 11 14  1  0  0  0  0
 12 15  1  0  0  0  0
 13 15  1  0  0  0  0
 16 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 21  1  0  0  0  0
M  END

     RDKit          3D

 51 54  0  0  0  0  0  0  0  0999 V2000
   -2.8570   -0.5764    1.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4599   -0.5508   -0.2803 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6654   -1.7272   -0.7130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3567   -1.7310    0.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4382   -0.4884   -0.2787 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3898    0.6972    0.1816 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4229    1.9405   -0.2039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5944    1.9480    0.7509 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4731    0.7821    0.4703 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3694    1.1659   -0.7166 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4496    0.1566   -0.7190 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5497    0.4038   -1.1349 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1359   -1.1869   -0.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6614   -1.4219   -0.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8054   -0.5235    0.3250 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7591   -1.2029    1.7020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6382    0.6996   -0.6129 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6124    1.7749   -0.3236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9187    1.2090   -0.8539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6834   -0.2697   -1.0958 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7876   -1.0055   -0.6867 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5348    0.3131    1.3279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0274   -0.5621    1.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4794   -1.4579    1.3343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2220   -2.6502   -0.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5492   -1.7297   -1.7952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6087   -1.8182    1.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2257   -2.6235   -0.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5058   -0.4276   -1.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5251    0.6776    1.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7788    1.7431   -1.2518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1763    2.8516   -0.1791 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1670    2.8821    0.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1709    1.8764    1.7735 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1975    0.7050    1.3354 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7495    2.1901   -0.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8031    1.2238   -1.6488 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2317   -1.1528    0.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7755   -1.9829   -0.6095 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4894   -1.0927   -1.6100 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4034   -2.4814   -0.4616 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6517   -0.8961    2.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8178   -2.3192    1.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8718   -0.9184    2.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4013    0.6488   -1.6794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3377    2.7063   -0.9003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6699    2.0623    0.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1260    1.7016   -1.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7195    1.3870   -0.1263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4365   -0.4424   -2.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3159   -0.5074   -0.0298 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  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  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
  2 17  1  0
 15  5  1  0
  6 17  1  0
 15  9  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
  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  6
  6 30  1  1
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  1
 10 36  1  0
 10 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


  Mrv0541 02231220512D          

 25 28  0  0  1  0            999 V2000
   20.0052   -3.2205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5192   -6.7741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2539   -5.4935    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.5394   -5.0810    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.9683   -5.0810    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.9683   -4.2561    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.7887   -5.4991    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.7820   -6.3584    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.5394   -4.2561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2539   -3.8436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2671   -6.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7489   -5.3324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7489   -4.0046    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.5262   -6.7881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2303   -4.6686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0241   -5.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9683   -3.4311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7950   -4.6741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0104   -6.8119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2421   -5.4693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2352   -6.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2642   -4.5816    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.5473   -5.9060    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.0793   -5.9023    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.7846   -7.0184    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 13  1  1  1  0  0  0
  2 21  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3 11  1  0  0  0  0
  3 22  1  1  0  0  0
  4  7  1  0  0  0  0
  4  9  1  0  0  0  0
  4 23  1  6  0  0  0
  5  6  1  0  0  0  0
  5 12  1  0  0  0  0
  5 24  1  6  0  0  0
  6 10  1  0  0  0  0
  6 13  1  0  0  0  0
  6 17  1  1  0  0  0
  7  8  1  0  0  0  0
  7 16  1  0  0  0  0
  7 18  1  1  0  0  0
  8 14  1  0  0  0  0
  8 19  1  0  0  0  0
  8 25  1  1  0  0  0
  9 10  1  0  0  0  0
 11 14  1  0  0  0  0
 12 15  1  0  0  0  0
 13 15  1  0  0  0  0
 16 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0257891

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])CC(=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/h12,14-17,21H,3-11H2,1-2H3/t12-,14+,15+,16+,17+,18+,19+/m1/s1

> <INCHI_KEY>
NVKAWKQGWWIWPM-MISPCMORSA-N

> <FORMULA>
C19H30O2

> <MOLECULAR_WEIGHT>
290.4403

> <EXACT_MASS>
290.224580204

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
34.45766697599501

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,7R,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one

> <ALOGPS_LOGP>
3.37

> <JCHEM_LOGP>
3.4112576326666675

> <ALOGPS_LOGS>
-4.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.37770535655329

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8839915294840951

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
83.6031

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.98e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5β-dihydrotestosterone

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      37.343  -6.012   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      27.103 -12.645   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      34.074 -10.255   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      32.740  -9.485   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      35.407  -9.485   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      35.407  -7.945   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      31.339 -10.265   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      31.326 -11.869   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      32.740  -7.945   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      34.074  -7.175   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      34.099 -11.858   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      36.865  -9.954   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      36.865  -7.475   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      32.716 -12.671   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      37.763  -8.715   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      29.912  -9.396   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      35.407  -6.405   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      31.351  -8.725   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      29.886 -12.716   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      28.452 -10.209   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      28.439 -11.880   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0      34.093  -8.552   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0      32.755 -11.025   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      35.615 -11.018   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      31.331 -13.101   0.000  0.00  0.00           H+0
CONECT    1   13                                                            
CONECT    2   21                                                            
CONECT    3    4    5   11   22                                             
CONECT    4    3    7    9   23                                             
CONECT    5    3    6   12   24                                             
CONECT    6    5   10   13   17                                             
CONECT    7    4    8   16   18                                             
CONECT    8    7   14   19   25                                             
CONECT    9    4   10                                                       
CONECT   10    6    9                                                       
CONECT   11    3   14                                                       
CONECT   12    5   15                                                       
CONECT   13    1    6   15                                                  
CONECT   14    8   11                                                       
CONECT   15   12   13                                                       
CONECT   16    7   20                                                       
CONECT   17    6                                                            
CONECT   18    7                                                            
CONECT   19    8   21                                                       
CONECT   20   16   21                                                       
CONECT   21    2   19   20                                                  
CONECT   22    3                                                            
CONECT   23    4                                                            
CONECT   24    5                                                            
CONECT   25    8                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Value	Source
(5beta,17beta)-17-Hydroxyandrostan-3-one	ChEBI
(5beta,8alpha,17beta)-17-Hydroxyandrostan-3-one	ChEBI
17beta-Hydroxyetiocholan-3-one	ChEBI
5-beta-DHT	ChEBI
5beta,17beta-Hydroxyandrostan-3-one	ChEBI
5beta-Androstan-17beta-ol-3-one	ChEBI
Etiocholan-17-beta-ol-3-one	ChEBI
(5b,17b)-17-Hydroxyandrostan-3-one	Generator
(5Β,17β)-17-hydroxyandrostan-3-one	Generator
(5b,8a,17b)-17-Hydroxyandrostan-3-one	Generator
(5Β,8α,17β)-17-hydroxyandrostan-3-one	Generator
17b-Hydroxyetiocholan-3-one	Generator
17Β-hydroxyetiocholan-3-one	Generator
5-b-DHT	Generator
5-Β-DHT	Generator
5b,17b-Hydroxyandrostan-3-one	Generator
5Β,17β-hydroxyandrostan-3-one	Generator
5b-Androstan-17b-ol-3-one	Generator
5Β-androstan-17β-ol-3-one	Generator
Etiocholan-17-b-ol-3-one	Generator
Etiocholan-17-β-ol-3-one	Generator
5beta-Dihydrotestosterone	HMDB
17beta-Hydroxy-5beta-androstan-3-one	HMDB

Chemical Formula

C₁₉H₃₀O₂

Average Mass

290.4403 Da

Monoisotopic Mass

290.22458 Da

IUPAC Name

(1S,2S,7R,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one

Traditional Name

5β-dihydrotestosterone

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])CC(=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/h12,14-17,21H,3-11H2,1-2H3/t12-,14+,15+,16+,17+,18+,19+/m1/s1

InChI Key

NVKAWKQGWWIWPM-MISPCMORSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Mus musculus	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Androstane steroids

Direct Parent

Androgens and derivatives

Alternative Parents

Substituents

Androgen-skeleton
3-oxosteroid
3-oxo-5-beta-steroid
17-hydroxysteroid
Oxosteroid
Hydroxysteroid
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-hydroxy steroid (CHEBI:2150 )
17beta-hydroxyandrostan-3-one (CHEBI:2150 )
C19 steroids (androgens) and derivatives (C05293 )
C19 steroids (androgens) and derivatives (LMST02020069 )

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	3.37	ALOGPS
logP	3.41	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	19.38	ChemAxon
pKa (Strongest Basic)	-0.88	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	83.6 m³·mol⁻¹	ChemAxon
Polarizability	34.46 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

External Links

HMDB ID

HMDB0006770

DrugBank ID

DB07447

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB024072

KNApSAcK ID

Not Available

Chemspider ID

10827

KEGG Compound ID

C05293

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11302

PDB ID

Not Available

ChEBI ID

428206

Good Scents ID

Not Available

References

General References

Perusquia M, Villalon CM: Possible role of Ca2+ channels in the vasodilating effect of 5beta-dihydrotestosterone in rat aorta. Eur J Pharmacol. 1999 Apr 29;371(2-3):169-78. doi: 10.1016/s0014-2999(99)00161-2. [PubMed:10357254 ]
Bordallo C, Rubin JM, Varona AB, Cantabrana B, Hidalgo A, Sanchez M: Increases in ornithine decarboxylase activity in the positive inotropism induced by androgens in isolated left atrium of the rat. Eur J Pharmacol. 2001 Jun 22;422(1-3):101-7. doi: 10.1016/s0014-2999(01)01039-1. [PubMed:11430920 ]
Perusquia M, Navarrete E, Jasso-Kamel J, Montano LM: Androgens induce relaxation of contractile activity in pregnant human myometrium at term: a nongenomic action on L-type calcium channels. Biol Reprod. 2005 Aug;73(2):214-21. doi: 10.1095/biolreprod.104.036954. Epub 2005 Mar 9. [PubMed:15758151 ]
Perusquia M, Navarrete E, Gonzalez L, Villalon CM: The modulatory role of androgens and progestins in the induction of vasorelaxation in human umbilical artery. Life Sci. 2007 Sep 1;81(12):993-1002. doi: 10.1016/j.lfs.2007.07.024. Epub 2007 Aug 7. [PubMed:17804019 ]
Montano LM, Calixto E, Figueroa A, Flores-Soto E, Carbajal V, Perusquia M: Relaxation of androgens on rat thoracic aorta: testosterone concentration dependent agonist/antagonist L-type Ca2+ channel activity, and 5beta-dihydrotestosterone restricted to L-type Ca2+ channel blockade. Endocrinology. 2008 May;149(5):2517-26. doi: 10.1210/en.2007-1288. Epub 2008 Feb 14. [PubMed:18276759 ]
Schumacher M, Hutchison RE, Hutchison JB: Inhibition of hypothalamic aromatase activity by 5 Beta-dihydrotestosterone. J Neuroendocrinol. 1991 Apr 1;3(2):221-6. doi: 10.1111/j.1365-2826.1991.tb00266.x. [PubMed:19215525 ]
Massa R, Cresti L, Martini L: Metabolism of testosterone in the anterior pituitary gland and the central nervous system of the European starling (Sturnus vulgaris). J Endocrinol. 1977 Dec;75(3):347-54. doi: 10.1677/joe.0.0750347. [PubMed:591837 ]
LOTUS database [Link]

Showing NP-Card for 5β-dihydrotestosterone (NP0257891)

MOL for NP0257891 (5β-dihydrotestosterone)

3D MOL for NP0257891 (5β-dihydrotestosterone)

3D SDF for NP0257891 (5β-dihydrotestosterone)

3D-SDF for NP0257891 (5β-dihydrotestosterone)

PDB for NP0257891 (5β-dihydrotestosterone)

3D PDB for NP0257891 (5β-dihydrotestosterone)

SMILES for NP0257891 (5β-dihydrotestosterone)

INCHI for NP0257891 (5β-dihydrotestosterone)

Structure for NP0257891 (5β-dihydrotestosterone)

3D Structure for NP0257891 (5β-dihydrotestosterone)