NP-MRD: Showing NP-Card for (+)-Androsta-1,4-diene-3,17-dione (NP0081233)

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Record Information

Version

2.0

Created at

2022-04-29 02:11:53 UTC

Updated at

2022-04-29 02:11:53 UTC

NP-MRD ID

NP0081233

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Androsta-1,4-diene-3,17-dione

Description

(1S,2S,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,6-diene-5,14-dione 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. (+)-Androsta-1,4-diene-3,17-dione is found in Aglaia rubiginosa and Plumbago zeylanica . Based on a literature review very few articles have been published on (1S,2S,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,6-diene-5,14-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 45 48  0  0  0  0  0  0  0  0999 V2000
   -1.8009   -1.7422    1.2145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2062   -0.7850    0.1439 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7437   -1.2128   -1.2116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2325   -1.3128   -1.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3207    0.0794   -0.9374 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1690    0.6664    0.3585 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2547    2.1269    0.4073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7789    2.2207    0.3564 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2946    0.7951    0.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0796    0.2837    1.1494 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5903   -1.0945    1.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3459   -1.5985    1.9246 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1451   -1.8298   -0.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3635   -1.2947   -0.9942 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8432    0.0715   -0.9314 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3481    0.8239   -2.1807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6466    0.6243    0.3756 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3250    0.9637    1.6535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7607    0.4913    1.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6366   -0.4986    0.2714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5273   -0.9739   -0.3847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8083   -1.5927    1.6346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5652   -1.7785    2.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8457   -2.7754    0.7604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1877   -2.1701   -1.5206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9927   -0.4271   -1.9441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0929   -1.6950   -2.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0362   -1.9820   -0.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0199    0.6817   -1.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2549    0.0854    1.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0697    2.5503    1.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1593    2.6997   -0.4218 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1122    2.6889    1.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1380    2.8408   -0.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3640    0.9088    1.9996 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4920   -2.8716   -0.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0924   -1.9540   -1.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6665    1.6325   -2.4379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3183    1.2683   -1.8805 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5475    0.0908   -2.9628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0859    1.2491   -0.4277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9062    0.2914    2.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2958    2.0191    1.9335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1892    0.0277    2.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3050    1.4079    1.0488 H   0  0  0  0  0  0  0  0  0  0  0  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  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  6
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 17  2  1  0
 20  2  1  0
 15  5  1  0
 15  9  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
 10 35  1  0
 13 36  1  0
 14 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  6
 18 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
M  END


  Mrv1652304292204112D          

 21 24  0  0  1  0            999 V2000
    2.6190    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.7029    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8705    0.0722    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6826    0.2174    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9629    0.9934    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4311    1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875    0.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939    1.6179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168    0.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340   -0.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3228    1.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781   -0.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9098    0.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266    0.5577    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8069    1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  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  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  1  0  0  0
  5 11  1  1  0  0  0
  3 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
  2 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0081233

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)C=C[C@@]34C)[C@@H]1CCC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H24O2/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/h7,9,11,14-16H,3-6,8,10H2,1-2H3/t14-,15-,16-,18+,19-/m0/s1

> <INCHI_KEY>
LUJVUUWNAPIQQI-FYAJOAKPSA-N

> <FORMULA>
C19H24O2

> <MOLECULAR_WEIGHT>
284.399

> <EXACT_MASS>
284.177630013

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
32.347136911930505

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-diene-5,14-dione

> <ALOGPS_LOGP>
2.78

> <JCHEM_LOGP>
3.926774492999999

> <ALOGPS_LOGS>
-4.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.826239116141732

> <JCHEM_PKA_STRONGEST_BASIC>
-5.000703377792103

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
84.70079999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.69e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-diene-5,14-dione

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       4.889   2.761   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.366   1.312   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.358   0.135   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.874   0.406   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.398   1.854   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.405   3.032   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.937   1.804   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.882   3.020   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.365   0.325   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.090  -0.539   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.069   3.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.835  -1.314   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.319  -1.585   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.326  -0.407   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.810  -0.678   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.182   0.499   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.698   0.228   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.341   1.947   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.857   2.218   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.850   1.041   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.373   2.489   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   20                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   11                                             
CONECT    6    5    1                                                       
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9    4                                                       
CONECT   11    5                                                            
CONECT   12    3   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    2   14   21                                             
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₄O₂

Average Mass

284.3990 Da

Monoisotopic Mass

284.17763 Da

IUPAC Name

(1S,2S,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-diene-5,14-dione

Traditional Name

(1S,2S,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-diene-5,14-dione

CAS Registry Number

Not Available

SMILES

C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)C=C[C@@]34C)[C@@H]1CCC2=O

InChI Identifier

InChI=1S/C19H24O2/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/h7,9,11,14-16H,3-6,8,10H2,1-2H3/t14-,15-,16-,18+,19-/m0/s1

InChI Key

LUJVUUWNAPIQQI-FYAJOAKPSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Aglaia rubiginosa	Plant	KNApSAcK
Plumbago zeylanica	Plant	KNApSAcK

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
Oxosteroid
17-oxosteroid
3-oxosteroid
3-oxo-delta-1,4-steroid
Delta-1,4-steroid
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	2.78	ALOGPS
logP	3.93	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	18.83	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	84.7 m³·mol⁻¹	ChemAxon
Polarizability	32.35 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

12882269

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Androsta-1,4-diene-3,17-dione (NP0081233)

MOL for NP0081233 ((+)-Androsta-1,4-diene-3,17-dione)

3D MOL for NP0081233 ((+)-Androsta-1,4-diene-3,17-dione)

3D SDF for NP0081233 ((+)-Androsta-1,4-diene-3,17-dione)

3D-SDF for NP0081233 ((+)-Androsta-1,4-diene-3,17-dione)

PDB for NP0081233 ((+)-Androsta-1,4-diene-3,17-dione)

3D PDB for NP0081233 ((+)-Androsta-1,4-diene-3,17-dione)

SMILES for NP0081233 ((+)-Androsta-1,4-diene-3,17-dione)

INCHI for NP0081233 ((+)-Androsta-1,4-diene-3,17-dione)

Structure for NP0081233 ((+)-Androsta-1,4-diene-3,17-dione)

3D Structure for NP0081233 ((+)-Androsta-1,4-diene-3,17-dione)