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Showing NP-Card for 5-androstene-3,17-dione (NP0339857)

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Record Information
Version2.0
Created at2024-09-11 23:53:30 UTC
Updated at2024-09-11 23:53:30 UTC
NP-MRD IDNP0339857
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-androstene-3,17-dione
Description 5-androstene-3,17-dione was first documented in 2004 (PMID: 15600343). Based on a literature review a small amount of articles have been published on 5-androstene-3,17-dione (PMID: 38951177) (PMID: 31226491) (PMID: 25248748) (PMID: 16620897).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0339857 (5-androstene-3,17-dione)


  Mrv2104 05272302252D          

 21 24  0  0  0  0            999 V2000
    3.9503   -1.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6700   -0.9702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1382   -1.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3261   -1.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0458   -0.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2336   -0.5346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5776   -0.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3897   -0.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9215    0.4364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7336    0.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0139   -0.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8261   -0.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4774   -0.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1602   -0.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9309   -1.3791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4373   -2.0304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1064   -1.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5745   -2.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7624   -1.8914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4821   -1.1154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4662   -2.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  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
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 11 20  1  0  0  0  0
  2 20  1  0  0  0  0
 17 21  1  0  0  0  0
 12 17  1  0  0  0  0
  2  8  1  0  0  0  0
M  END
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3D MOL for NP0339857 (5-androstene-3,17-dione)

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3D SDF for NP0339857 (5-androstene-3,17-dione)

  Mrv2104 05272302252D          

 21 24  0  0  0  0            999 V2000
    3.9503   -1.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6700   -0.9702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1382   -1.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3261   -1.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0458   -0.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2336   -0.5346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5776   -0.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3897   -0.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9215    0.4364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7336    0.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0139   -0.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8261   -0.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4774   -0.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1602   -0.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9309   -1.3791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4373   -2.0304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1064   -1.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5745   -2.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7624   -1.8914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4821   -1.1154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4662   -2.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  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
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 11 20  1  0  0  0  0
  2 20  1  0  0  0  0
 17 21  1  0  0  0  0
 12 17  1  0  0  0  0
  2  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339857

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CCC3C(CC=C4CC(=O)CCC34C)C1CCC2=O

> <INCHI_IDENTIFIER>
InChI=1/C19H26O2/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/h3,14-16H,4-11H2,1-2H3

> <INCHI_KEY>
SQGZFRITSMYKRH-UHFFFAOYNA-N

> <FORMULA>
C19H26O2

> <MOLECULAR_WEIGHT>
286.415

> <EXACT_MASS>
286.193280077

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
33.1494740522928

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthrene-1,7-dione

> <JCHEM_LOGP>
3.569205857

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.169935131792723

> <JCHEM_PKA_STRONGEST_BASIC>
-7.1511823837848185

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
83.6308

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
9a,11a-dimethyl-2H,3H,3aH,3bH,4H,6H,8H,9H,9bH,10H,11H-cyclopenta[a]phenanthrene-1,7-dione

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0339857 (5-androstene-3,17-dione)
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PDB for NP0339857 (5-androstene-3,17-dione)
HEADER    PROTEIN                                 27-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-23         0                                  
HETATM    1  C   UNK     0       7.374  -3.259   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.851  -1.811   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.858  -2.988   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.342  -2.717   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.819  -1.269   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.303  -0.998   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.811  -0.092   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.327  -0.363   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.320   0.815   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.836   0.544   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.359  -0.905   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.875  -1.176   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.091  -0.231   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.366  -1.095   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.938  -2.574   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      13.883  -3.790   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      11.399  -2.624   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.406  -3.802   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.890  -3.531   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.367  -2.082   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.070  -4.010   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   20    8                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9    2                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   20                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   21   12                                             
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   11    2                                                  
CONECT   21   17                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

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3D PDB for NP0339857 (5-androstene-3,17-dione)
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SMILES for NP0339857 (5-androstene-3,17-dione)
CC12CCC3C(CC=C4CC(=O)CCC34C)C1CCC2=O
Download
INCHI for NP0339857 (5-androstene-3,17-dione)
InChI=1/C19H26O2/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/h3,14-16H,4-11H2,1-2H3
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SynonymsNot Available
Chemical FormulaC19H26O2
Average Mass286.4150 Da
Monoisotopic Mass286.19328 Da
IUPAC Name9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthrene-1,7-dione
Traditional Name9a,11a-dimethyl-2H,3H,3aH,3bH,4H,6H,8H,9H,9bH,10H,11H-cyclopenta[a]phenanthrene-1,7-dione
CAS Registry NumberNot Available
SMILES
CC12CCC3C(CC=C4CC(=O)CCC34C)C1CCC2=O
InChI Identifier
InChI=1/C19H26O2/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/h3,14-16H,4-11H2,1-2H3
InChI KeySQGZFRITSMYKRH-UHFFFAOYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
ClassificationNot classified
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.57ChemAxon
pKa (Strongest Acidic)16.17ChemAxon
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity83.63 m³·mol⁻¹ChemAxon
Polarizability33.15 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Dai J, Wu Z, Liu Z, Li C, Zhu L, Chen H, Chen X: Sources and control of impurity during one-pot enzymatic production of dehydroepiandrosterone. Appl Microbiol Biotechnol. 2024 Jun 29;108(1):399. doi:  10.1007/s00253-024-13221-3. [PubMed:38951177  ] 
  2. Peng F, Cheng X, Wang H, Song S, Chen T, Li X, He Y, Huang Y, Liu S, Yang F, Su Z: Structure-based reconstruction of a Mycobacterium hypothetical protein into an active Delta(5)-3-ketosteroid isomerase. Biochim Biophys Acta Proteins Proteom. 2019 Sep;1867(9):821-830. doi:  10.1016/j.bbapap.2019.06.008. Epub 2019 Jun 19. [PubMed:31226491  ] 
  3. Daka JL, Achilonu I, Dirr HW: The isomerization of Delta5-androstene-3,17-dione by the human glutathione transferase A3-3 proceeds via a conjugated heteroannular diene intermediate. J Biol Chem. 2014 Nov 14;289(46):32243-32252. doi: 10.1074/jbc.M114.601609. Epub  2014 Sep 23. [PubMed:25248748  ] 
  4. Sharma K, Vazquez-Ramirez R, Kubli-Garfias C: A theoretical model of the catalytic mechanism of the Delta5-3-ketosteroid isomerase reaction. Steroids. 2006 Jul;71(7):549-57. doi: 10.1016/j.steroids.2005.12.001. Epub 2006  Apr 18. [PubMed:16620897  ] 
  5. Houck WJ, Pollack RM: Temperature effects on the catalytic activity of the D38E mutant of 3-oxo-Delta5-steroid isomerase: favorable enthalpies and entropies of activation relative to the nonenzymatic reaction catalyzed by acetate ion. J Am Chem Soc. 2004 Dec 22;126(50):16416-25. doi: 10.1021/ja046819k. [PubMed:15600343  ]