NP-MRD: Showing NP-Card for 19-Oxotestosterone (NP0334106)

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Record Information

Version

2.0

Created at

2024-09-09 22:12:44 UTC

Updated at

2024-09-09 22:12:45 UTC

NP-MRD ID

NP0334106

Secondary Accession Numbers

None

Natural Product Identification

Common Name

19-Oxotestosterone

Description

19-Oxotestosterone is catalyzed by Aromatase (EC 1.14.14.1),Also called estrogen synthetase (a cytochrome P450 enzyme which catalyzes the formation of aromatic C18 estrogens from C19 androgens; it is symbolized CYP19) into oestrogens via sequential oxidations at the 19-methyl group. Biosynthesis of estrogens from C19 steroids is catalyzed by aromatase and its tissue-specific expression is determined at least in part by alternative use of tissue-specific promoters, which give rise to transcripts with unique 5-prime noncoding termini.(OMIM 107910 ) [HMDB]

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05252300452D          

 25 28  0  0  1  0            999 V2000
    2.6232    0.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1073    0.1997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520    2.7844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8399    2.6391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0962    2.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5867    1.7614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2475    0.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8111    0.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4354    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9990    0.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9960    2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1838    2.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5278    1.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5596    1.8632    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7475    1.7180    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0914    1.2325    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3574    0.9689    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9035    1.3777    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4672    0.9421    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3399    1.8134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8637    0.3176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2793    1.0873    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9451    2.5190    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3717    2.0084    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1676    1.1244    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 18  1  1  6  0  0  0
 19  2  1  6  0  0  0
  3  4  1  0  0  0  0
  3 12  1  0  0  0  0
 14  4  1  0  0  0  0
  5  6  1  0  0  0  0
 15  5  1  0  0  0  0
 17  6  1  0  0  0  0
  7  9  1  0  0  0  0
  7 13  1  0  0  0  0
  8 10  1  0  0  0  0
 16  8  1  0  0  0  0
 18  9  1  0  0  0  0
 19 10  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 18 12  1  0  0  0  0
 13 20  2  0  0  0  0
 14 22  1  1  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 23  1  1  0  0  0
 15 19  1  0  0  0  0
 16 24  1  6  0  0  0
 16 18  1  0  0  0  0
 17 25  1  1  0  0  0
 19 17  1  0  0  0  0
 17 21  1  6  0  0  0
M  END


  Mrv2104 05252300452D          

 25 28  0  0  1  0            999 V2000
    2.6232    0.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1073    0.1997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520    2.7844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8399    2.6391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0962    2.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5867    1.7614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2475    0.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8111    0.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4354    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9990    0.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9960    2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1838    2.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5278    1.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5596    1.8632    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7475    1.7180    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0914    1.2325    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3574    0.9689    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9035    1.3777    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4672    0.9421    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3399    1.8134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8637    0.3176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2793    1.0873    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9451    2.5190    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3717    2.0084    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1676    1.1244    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 18  1  1  6  0  0  0
 19  2  1  6  0  0  0
  3  4  1  0  0  0  0
  3 12  1  0  0  0  0
 14  4  1  0  0  0  0
  5  6  1  0  0  0  0
 15  5  1  0  0  0  0
 17  6  1  0  0  0  0
  7  9  1  0  0  0  0
  7 13  1  0  0  0  0
  8 10  1  0  0  0  0
 16  8  1  0  0  0  0
 18  9  1  0  0  0  0
 19 10  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 18 12  1  0  0  0  0
 13 20  2  0  0  0  0
 14 22  1  1  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 23  1  1  0  0  0
 15 19  1  0  0  0  0
 16 24  1  6  0  0  0
 16 18  1  0  0  0  0
 17 25  1  1  0  0  0
 19 17  1  0  0  0  0
 17 21  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0334106

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(O)CC[C@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@@]4(C)[C@@]3([H])CC[C@@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C19H28O2/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/h11,14-17,21H,3-10H2,1-2H3/t14-,15+,16-,17+,18+,19+/m0/s1

> <INCHI_KEY>
MUMGGOZAMZWBJJ-PKRLLGJHSA-N

> <FORMULA>
C19H28O2

> <MOLECULAR_WEIGHT>
288.431

> <EXACT_MASS>
288.208930142

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
33.952387850338496

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3aR,3bR,9aS,9bS,11aR)-1-hydroxy-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,5H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one

> <JCHEM_LOGP>
3.365423297666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.377705208106928

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.52379863216175

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8839411233575452

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
84.42979999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3aR,3bR,9aS,9bS,11aR)-1-hydroxy-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,5H,8H,9H,9bH,10H,11H-cyclopenta[a]phenanthren-7-one

> <JCHEM_VEBER_RULE>
1

$$$$

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       4.897   1.123   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.200   0.373   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.950   5.197   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.434   4.926   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.179   4.152   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.095   3.288   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.929   1.666   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.381   0.852   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.413   1.394   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.865   0.581   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.459   4.291   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.943   4.020   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.452   3.114   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.911   3.478   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.395   3.207   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.904   2.301   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.667   1.809   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.420   2.572   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.872   1.759   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.968   3.385   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.612   0.593   0.000  0.00  0.00           O+0
HETATM   22  H   UNK     0       2.388   2.030   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       1.764   4.702   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       4.427   3.749   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.180   2.099   0.000  0.00  0.00           H+0
CONECT    1   18                                                            
CONECT    2   19                                                            
CONECT    3    4   12                                                       
CONECT    4    3   14                                                       
CONECT    5    6   15                                                       
CONECT    6    5   17                                                       
CONECT    7    9   13                                                       
CONECT    8   10   16                                                       
CONECT    9    7   18                                                       
CONECT   10    8   19                                                       
CONECT   11   12   13                                                       
CONECT   12    3   11   18                                                  
CONECT   13    7   11   20                                                  
CONECT   14    4   22   15   16                                             
CONECT   15    5   14   23   19                                             
CONECT   16    8   14   24   18                                             
CONECT   17    6   25   19   21                                             
CONECT   18    1    9   12   16                                             
CONECT   19    2   10   15   17                                             
CONECT   20   13                                                            
CONECT   21   17                                                            
CONECT   22   14                                                            
CONECT   23   15                                                            
CONECT   24   16                                                            
CONECT   25   17                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₈O₂

Average Mass

288.4310 Da

Monoisotopic Mass

288.20893 Da

IUPAC Name

(1R,3aR,3bR,9aS,9bS,11aR)-1-hydroxy-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,5H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one

Traditional Name

(1R,3aR,3bR,9aS,9bS,11aR)-1-hydroxy-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,5H,8H,9H,9bH,10H,11H-cyclopenta[a]phenanthren-7-one

CAS Registry Number

Not Available

SMILES

[H][C@@]1(O)CC[C@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@@]4(C)[C@@]3([H])CC[C@@]12C

InChI Identifier

InChI=1S/C19H28O2/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/h11,14-17,21H,3-10H2,1-2H3/t14-,15+,16-,17+,18+,19+/m0/s1

InChI Key

MUMGGOZAMZWBJJ-PKRLLGJHSA-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

Diterpenoid
Androgen-skeleton
17-hydroxysteroid
Oxosteroid
Hydroxysteroid
3-oxosteroid
3-oxo-delta-4-steroid
Delta-4-steroid
Cyclohexenone
Alpha,beta-unsaturated ketone
Enone
Cyclic alcohol
Acryloyl-group
Cyclic ketone
Secondary alcohol
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

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	ChemAxon
pKa (Strongest Acidic)	18.52	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	84.43 m³·mol⁻¹	ChemAxon
Polarizability	33.95 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

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

162460416

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 19-Oxotestosterone (NP0334106)

MOL for NP0334106 (19-Oxotestosterone)

3D MOL for NP0334106 (19-Oxotestosterone)

3D SDF for NP0334106 (19-Oxotestosterone)

3D-SDF for NP0334106 (19-Oxotestosterone)

PDB for NP0334106 (19-Oxotestosterone)

3D PDB for NP0334106 (19-Oxotestosterone)

SMILES for NP0334106 (19-Oxotestosterone)

INCHI for NP0334106 (19-Oxotestosterone)

Structure for NP0334106 (19-Oxotestosterone)

3D Structure for NP0334106 (19-Oxotestosterone)