NP-MRD: Showing NP-Card for Oxymesterone (NP0334748)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2024-09-10 19:47:57 UTC

Updated at

2024-09-10 19:47:57 UTC

NP-MRD ID

NP0334748

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Oxymesterone

Description

Oxymesterone, also known as anamidol or aranabol, 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. Oxymesterone is an extremely weak basic (essentially neutral) compound (based on its pKa). It was known by 1960.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02231220322D          

 26 29  0  0  1  0            999 V2000
   15.8750   -7.8403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3807   -6.9776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8295   -4.4597    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.8295   -5.2846    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.1152   -5.6971    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.4007   -5.2846    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.6100   -4.2084    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.1152   -4.0473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6501   -5.7028    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.6100   -5.5360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4007   -4.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0915   -4.8722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1284   -6.5563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6435   -6.5619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3876   -6.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8856   -5.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6564   -4.8779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1035   -5.6730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8719   -7.0154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0967   -6.5679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8993   -6.1471    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.1255   -4.7440    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.4224   -6.1232    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.8663   -3.4243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4300   -4.0558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9168   -3.6394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  1  0  0  0  0
  2 20  2  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  4 10  1  0  0  0  0
  4 21  1  6  0  0  0
  5  6  1  0  0  0  0
  5 13  1  0  0  0  0
  5 22  1  1  0  0  0
  6  9  1  0  0  0  0
  6 11  1  0  0  0  0
  6 23  1  6  0  0  0
  7 12  1  0  0  0  0
  8 11  1  0  0  0  0
  9 14  1  0  0  0  0
  9 16  1  0  0  0  0
  9 17  1  1  0  0  0
 10 12  1  0  0  0  0
 13 15  1  0  0  0  0
 14 15  1  0  0  0  0
 14 19  2  0  0  0  0
 16 18  1  0  0  0  0
 18 20  1  0  0  0  0
 19 20  1  0  0  0  0
  7 24  1  1  0  0  0
  7 25  1  6  0  0  0
  3 26  1  1  0  0  0
M  END


  Mrv0541 02231220322D          

 26 29  0  0  1  0            999 V2000
   15.8750   -7.8403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3807   -6.9776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8295   -4.4597    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.8295   -5.2846    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.1152   -5.6971    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.4007   -5.2846    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.6100   -4.2084    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.1152   -4.0473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6501   -5.7028    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.6100   -5.5360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4007   -4.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0915   -4.8722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1284   -6.5563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6435   -6.5619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3876   -6.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8856   -5.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6564   -4.8779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1035   -5.6730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8719   -7.0154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0967   -6.5679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8993   -6.1471    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.1255   -4.7440    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.4224   -6.1232    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.8663   -3.4243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4300   -4.0558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9168   -3.6394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  1  0  0  0  0
  2 20  2  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  4 10  1  0  0  0  0
  4 21  1  6  0  0  0
  5  6  1  0  0  0  0
  5 13  1  0  0  0  0
  5 22  1  1  0  0  0
  6  9  1  0  0  0  0
  6 11  1  0  0  0  0
  6 23  1  6  0  0  0
  7 12  1  0  0  0  0
  8 11  1  0  0  0  0
  9 14  1  0  0  0  0
  9 16  1  0  0  0  0
  9 17  1  1  0  0  0
 10 12  1  0  0  0  0
 13 15  1  0  0  0  0
 14 15  1  0  0  0  0
 14 19  2  0  0  0  0
 16 18  1  0  0  0  0
 18 20  1  0  0  0  0
 19 20  1  0  0  0  0
  7 24  1  1  0  0  0
  7 25  1  6  0  0  0
  3 26  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0334748

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=C(O)C(=O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O3/c1-18-9-8-16(21)17(22)15(18)5-4-12-13(18)6-10-19(2)14(12)7-11-20(19,3)23/h12-14,22-23H,4-11H2,1-3H3/t12-,13+,14+,18-,19+,20+/m1/s1

> <INCHI_KEY>
RXXBBHGCAXVBES-XMUHMHRVSA-N

> <FORMULA>
C20H30O3

> <MOLECULAR_WEIGHT>
318.4504

> <EXACT_MASS>
318.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
36.71217252944716

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,10R,11S,14S,15S)-6,14-dihydroxy-2,14,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

> <ALOGPS_LOGP>
2.99

> <JCHEM_LOGP>
3.127342284666667

> <ALOGPS_LOGS>
-3.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.313190913539229

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5280912870485565

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
91.0354

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.69e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
oxymesterone

> <JCHEM_VEBER_RULE>
0

$$$$

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      29.633 -14.635   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      26.844 -13.025   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      35.148  -8.325   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      35.148  -9.865   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      33.815 -10.635   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      32.481  -9.865   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      36.605  -7.856   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      33.815  -7.555   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      31.080 -10.645   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      36.605 -10.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      32.481  -8.325   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      37.504  -9.095   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      33.840 -12.238   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      31.068 -12.249   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      32.457 -13.051   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      29.653  -9.776   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      31.092  -9.105   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.193 -10.590   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      29.628 -13.095   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      28.181 -12.260   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0      35.279 -11.475   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0      33.834  -8.855   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0      32.522 -11.430   0.000  0.00  0.00           H+0
HETATM   24  O   UNK     0      37.084  -6.392   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      38.136  -7.571   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      35.311  -6.794   0.000  0.00  0.00           C+0
CONECT    1   19                                                            
CONECT    2   20                                                            
CONECT    3    4    7    8   26                                             
CONECT    4    3    5   10   21                                             
CONECT    5    4    6   13   22                                             
CONECT    6    5    9   11   23                                             
CONECT    7    3   12   24   25                                             
CONECT    8    3   11                                                       
CONECT    9    6   14   16   17                                             
CONECT   10    4   12                                                       
CONECT   11    6    8                                                       
CONECT   12    7   10                                                       
CONECT   13    5   15                                                       
CONECT   14    9   15   19                                                  
CONECT   15   13   14                                                       
CONECT   16    9   18                                                       
CONECT   17    9                                                            
CONECT   18   16   20                                                       
CONECT   19    1   14   20                                                  
CONECT   20    2   18   19                                                  
CONECT   21    4                                                            
CONECT   22    5                                                            
CONECT   23    6                                                            
CONECT   24    7                                                            
CONECT   25    7                                                            
CONECT   26    3                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Value	Source
4,17beta-Dihydroxy-17alpha-methylandrost-4-en-3-one	Kegg
4-Hydroxy-17alpha-methyltestosterone	Kegg
4,17b-Dihydroxy-17a-methylandrost-4-en-3-one	Generator
4,17Β-dihydroxy-17α-methylandrost-4-en-3-one	Generator
4-Hydroxy-17a-methyltestosterone	Generator
4-Hydroxy-17α-methyltestosterone	Generator
(17b)- 4,17b-Dihydroxy-17-methyl-androst-4-en-3-one	HMDB
4,17b-Dihydroxy-17-methyl-androst-4-en-3-one	HMDB
4,17b-Dihydroxy-17-methylandrost-4-en-3-one	HMDB
4-Hydroxy-17-methyltestosterone	HMDB
Anamidol	HMDB
Aranabol	HMDB
Oranabol	HMDB
Oxymestrone	HMDB
Theranabol	HMDB
17Alpah-methyl-4, 17beta-dihydroxy-androst-4-ene-3-one	HMDB
Oxymesterone	KEGG

Chemical Formula

C₂₀H₃₀O₃

Average Mass

318.4504 Da

Monoisotopic Mass

318.21949 Da

IUPAC Name

(1S,2R,10R,11S,14S,15S)-6,14-dihydroxy-2,14,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

Traditional Name

oxymesterone

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=C(O)C(=O)CC[C@]12C

InChI Identifier

InChI=1S/C20H30O3/c1-18-9-8-16(21)17(22)15(18)5-4-12-13(18)6-10-19(2)14(12)7-11-20(19,3)23/h12-14,22-23H,4-11H2,1-3H3/t12-,13+,14+,18-,19+,20+/m1/s1

InChI Key

RXXBBHGCAXVBES-XMUHMHRVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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-oxo-delta-4-steroid
3-oxosteroid
4-hydroxysteroid
Hydroxysteroid
Oxosteroid
17-hydroxysteroid
Delta-4-steroid
Cyclohexenone
Cyclic alcohol
Tertiary alcohol
Ketone
Cyclic ketone
Enol
Organic oxygen compound
Organooxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-hydroxy steroid (CHEBI:34903 )

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	2.99	ALOGPS
logP	3.13	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	9.31	ChemAxon
pKa (Strongest Basic)	-0.53	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	91.04 m³·mol⁻¹	ChemAxon
Polarizability	36.71 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