NP-MRD: Showing NP-Card for 3beta,17alpha-Dihydroxy-5alpha-androstane (NP0334616)

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Record Information

Version

2.0

Created at

2024-09-10 19:09:26 UTC

Updated at

2024-09-10 19:09:26 UTC

NP-MRD ID

NP0334616

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3beta,17alpha-Dihydroxy-5alpha-androstane

Description

3Beta,17alpha-Dihydroxy-5alpha-androstane is also known as 3β,17α-dihydroxy-5α-androstane. 3beta,17alpha-Dihydroxy-5alpha-androstane was first documented in 2001 (PMID: 11746924). Based on a literature review very few articles have been published on 3beta,17alpha-Dihydroxy-5alpha-androstane.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05252321412D          

 25 28  0  0  0  0            999 V2000
 9999.308010000.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.445010001.6296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4450 9999.1515    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1715 9998.3172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3080 9997.9063    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.732310000.3854    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.0216 9999.1515    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5965 9999.9703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8820 9999.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8820 9998.7327    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.5965 9998.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.733610001.2141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.019110000.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0191 9999.9765    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.7336 9999.5641    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.3071 9999.5578    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.3071 9998.7327    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.0216 9998.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7361 9998.7327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.232710001.0566    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.448110000.8016    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.4481 9999.9766    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.2327 9999.7217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.717610000.3891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.487710001.8412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 10  4  1  1  0  0  0
 11 17  1  0  0  0  0
 17  5  1  6  0  0  0
  8 16  1  0  0  0  0
 16  1  1  1  0  0  0
 14 16  1  0  0  0  0
 14  7  1  6  0  0  0
 19 15  1  0  0  0  0
 15  6  1  1  0  0  0
 20 21  1  0  0  0  0
 20 24  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 20 25  1  6  0  0  0
 15 22  1  0  0  0  0
 22  3  1  6  0  0  0
 12 21  1  0  0  0  0
 21  2  1  1  0  0  0
M  END


  Mrv2104 05252321412D          

 25 28  0  0  0  0            999 V2000
 9999.308010000.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.445010001.6296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4450 9999.1515    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1715 9998.3172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3080 9997.9063    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.732310000.3854    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.0216 9999.1515    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5965 9999.9703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8820 9999.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8820 9998.7327    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.5965 9998.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.733610001.2141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.019110000.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0191 9999.9765    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.7336 9999.5641    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.3071 9999.5578    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.3071 9998.7327    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.0216 9998.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7361 9998.7327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.232710001.0566    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.448110000.8016    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.4481 9999.9766    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.2327 9999.7217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.717610000.3891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.487710001.8412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 10  4  1  1  0  0  0
 11 17  1  0  0  0  0
 17  5  1  6  0  0  0
  8 16  1  0  0  0  0
 16  1  1  1  0  0  0
 14 16  1  0  0  0  0
 14  7  1  6  0  0  0
 19 15  1  0  0  0  0
 15  6  1  1  0  0  0
 20 21  1  0  0  0  0
 20 24  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 20 25  1  6  0  0  0
 15 22  1  0  0  0  0
 22  3  1  6  0  0  0
 12 21  1  0  0  0  0
 21  2  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0334616

> <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])C[C@@H](O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1/C19H32O2/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/h12-17,20-21H,3-11H2,1-2H3/t12-,13-,14-,15-,16-,17+,18-,19-/s2

> <INCHI_KEY>
CBMYJHIOYJEBSB-BZLOLWJINA-N

> <FORMULA>
C19H32O2

> <MOLECULAR_WEIGHT>
292.463

> <EXACT_MASS>
292.24023027

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
35.444658301324566

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3aS,3bR,5aS,7S,9aS,9bS,11aS)-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthrene-1,7-diol

> <JCHEM_LOGP>
3.2037568309999997

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.377705356554483

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.2963963211217

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7580100340749988

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
84.63119999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5-α-androstane-3-β,17-α-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-MAY-23         0                                  
HETATM    1  C   UNK     0    8665.3758667.386   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8669.3648669.709   0.000  0.00  0.00           C+0
HETATM    3  H   UNK     0    8669.3648665.083   0.000  0.00  0.00           H+0
HETATM    4  O   UNK     0    8661.3878663.525   0.000  0.00  0.00           O+0
HETATM    5  H   UNK     0    8665.3758662.758   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8668.0348667.386   0.000  0.00  0.00           H+0
HETATM    7  H   UNK     0    8666.7078665.083   0.000  0.00  0.00           H+0
HETATM    8  C   UNK     0    8664.0478666.611   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8662.7138665.841   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8662.7138664.301   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8664.0478663.531   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8668.0368668.933   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8666.7028668.163   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8666.7028666.623   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8668.0368665.853   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8665.3738665.841   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8665.3738664.301   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8666.7078663.531   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8668.0418664.301   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8670.8348668.639   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8669.3708668.163   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8669.3708666.623   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8670.8348666.147   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8671.7408667.393   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0    8671.3108670.104   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2   21                                                            
CONECT    3   22                                                            
CONECT    4   10                                                            
CONECT    5   17                                                            
CONECT    6   15                                                            
CONECT    7   14                                                            
CONECT    8    9   16                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11    4                                                  
CONECT   11   10   17                                                       
CONECT   12   13   21                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16    7                                             
CONECT   15   14   19    6   22                                             
CONECT   16   17    8    1   14                                             
CONECT   17   16   18   11    5                                             
CONECT   18   17   19                                                       
CONECT   19   18   15                                                       
CONECT   20   21   24   25                                                  
CONECT   21   20   22   12    2                                             
CONECT   22   21   23   15    3                                             
CONECT   23   22   24                                                       
CONECT   24   20   23                                                       
CONECT   25   20                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Value	Source
3b,17a-Dihydroxy-5a-androstane	Generator
3Β,17α-dihydroxy-5α-androstane	Generator

Chemical Formula

C₁₉H₃₂O₂

Average Mass

292.4630 Da

Monoisotopic Mass

292.24023 Da

IUPAC Name

(1R,3aS,3bR,5aS,7S,9aS,9bS,11aS)-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthrene-1,7-diol

Traditional Name

5-α-androstane-3-β,17-α-diol

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])C[C@@H](O)CC[C@]12C

InChI Identifier

InChI=1/C19H32O2/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/h12-17,20-21H,3-11H2,1-2H3/t12-,13-,14-,15-,16-,17+,18-,19-/s2

InChI Key

CBMYJHIOYJEBSB-BZLOLWJINA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound 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
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:40836 )
17alpha-hydroxy steroid (CHEBI:40836 )
androstane-3,17-diol (CHEBI:40836 )
C19 steroids (androgens) and derivatives (LMST02020080 )

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	3.2	ChemAxon
pKa (Strongest Acidic)	18.3	ChemAxon
pKa (Strongest Basic)	-0.76	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	84.63 m³·mol⁻¹	ChemAxon
Polarizability	35.44 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Prevost S, Nicol T, Monteau F, Andre F, Le Bizec B: Gas chromatography/combustion/isotope ratio mass spectrometry to control the misuse of androgens in breeding animals: new derivatisation method applied to testosterone metabolites and precursors in urine samples. Rapid Commun Mass Spectrom. 2001;15(24):2509-14. doi: 10.1002/rcm.538. [PubMed:11746924 ]

Showing NP-Card for 3beta,17alpha-Dihydroxy-5alpha-androstane (NP0334616)

MOL for NP0334616 (3beta,17alpha-Dihydroxy-5alpha-androstane)

3D MOL for NP0334616 (3beta,17alpha-Dihydroxy-5alpha-androstane)

3D SDF for NP0334616 (3beta,17alpha-Dihydroxy-5alpha-androstane)

3D-SDF for NP0334616 (3beta,17alpha-Dihydroxy-5alpha-androstane)

PDB for NP0334616 (3beta,17alpha-Dihydroxy-5alpha-androstane)

3D PDB for NP0334616 (3beta,17alpha-Dihydroxy-5alpha-androstane)

SMILES for NP0334616 (3beta,17alpha-Dihydroxy-5alpha-androstane)

INCHI for NP0334616 (3beta,17alpha-Dihydroxy-5alpha-androstane)

Structure for NP0334616 (3beta,17alpha-Dihydroxy-5alpha-androstane)

3D Structure for NP0334616 (3beta,17alpha-Dihydroxy-5alpha-androstane)