NP-MRD: Showing NP-Card for 5alpha-Stigmast-22-ene-3,6-dione (NP0046921)

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Record Information

Version

1.0

Created at

2022-03-17 20:31:43 UTC

Updated at

2022-03-17 20:31:43 UTC

NP-MRD ID

NP0046921

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5alpha-Stigmast-22-ene-3,6-dione

Description

5Alpha-Stigmast-22-ene-3,6-dione belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. 5Alpha-Stigmast-22-ene-3,6-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241212352D          

 32 35  0  0  0  0            999 V2000
   -2.3388   -1.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0533   -1.5989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0533   -2.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3388   -2.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6244   -2.4239    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6244   -1.5989    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9099   -1.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9099   -2.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1954   -2.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1954   -1.5989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1954    0.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9099   -0.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2335    0.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5190   -0.3614    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5190   -1.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9479   -1.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9479   -0.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7678   -2.8364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6244   -0.7739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5190    0.4636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9480    1.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2335    0.8761    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6624    0.8761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3769    1.2886    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0914    0.8761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8058    1.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0914    0.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5190    1.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3769    2.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0914    2.5261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6244   -3.2489    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9099   -3.6614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 18  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  7  6  1  0  0  0  0
  6 19  1  1  0  0  0
 12  7  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 11 14  1  0  0  0  0
 13 14  1  0  0  0  0
 22 13  1  0  0  0  0
 13 17  1  0  0  0  0
 14 15  1  0  0  0  0
 14 20  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 22 28  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 24 29  1  1  0  0  0
 29 30  1  0  0  0  0
  5 31  1  6  0  0  0
  8 32  2  0  0  0  0
M  END


  Mrv0541 02241212352D          

 32 35  0  0  0  0            999 V2000
   -2.3388   -1.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0533   -1.5989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0533   -2.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3388   -2.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6244   -2.4239    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6244   -1.5989    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9099   -1.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9099   -2.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1954   -2.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1954   -1.5989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1954    0.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9099   -0.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2335    0.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5190   -0.3614    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5190   -1.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9479   -1.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9479   -0.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7678   -2.8364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6244   -0.7739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5190    0.4636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9480    1.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2335    0.8761    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6624    0.8761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3769    1.2886    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0914    0.8761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8058    1.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0914    0.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5190    1.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3769    2.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0914    2.5261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6244   -3.2489    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9099   -3.6614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 18  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  7  6  1  0  0  0  0
  6 19  1  1  0  0  0
 12  7  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 11 14  1  0  0  0  0
 13 14  1  0  0  0  0
 22 13  1  0  0  0  0
 13 17  1  0  0  0  0
 14 15  1  0  0  0  0
 14 20  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 22 28  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 24 29  1  1  0  0  0
 29 30  1  0  0  0  0
  5 31  1  6  0  0  0
  8 32  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0046921

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H](C(C)C)\C=C\[C@@H](C)C1CCC2C3CC(=O)[C@@]4([H])CC(=O)CC[C@]4(C)C3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C29H46O2/c1-7-20(18(2)3)9-8-19(4)23-10-11-24-22-17-27(31)26-16-21(30)12-14-29(26,6)25(22)13-15-28(23,24)5/h8-9,18-20,22-26H,7,10-17H2,1-6H3/b9-8+/t19-,20-,22?,23?,24?,25?,26-,28-,29-/m1/s1

> <INCHI_KEY>
FJQGCLCMDPGZHC-PVHRTUTRSA-N

> <FORMULA>
C29H46O2

> <MOLECULAR_WEIGHT>
426.6743

> <EXACT_MASS>
426.349780716

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
52.65386220209871

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,7S,15R)-14-[(2R,3E,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,8-dione

> <ALOGPS_LOGP>
5.70

> <JCHEM_LOGP>
7.172384875000001

> <ALOGPS_LOGS>
-7.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.767757254796745

> <JCHEM_PKA_STRONGEST_BASIC>
-7.095221451774866

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
129.6719

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.59e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,7S,15R)-14-[(2R,3E,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,8-dione

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -4.366  -2.215   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.699  -2.985   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.699  -4.525   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.366  -5.295   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.032  -4.525   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.032  -2.985   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.698  -2.215   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.698  -5.295   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.365  -4.525   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.365  -2.985   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.365   0.095   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.698  -0.675   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.303   0.095   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.969  -0.675   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.969  -2.215   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.636  -2.215   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.636  -0.675   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -7.033  -5.295   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -3.032  -1.445   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.969   0.865   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.636   2.405   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.303   1.635   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.970   1.635   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.304   2.405   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.637   1.635   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.971   2.405   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.637   0.095   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.969   2.405   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.304   3.945   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.637   4.715   0.000  0.00  0.00           C+0
HETATM   31  H   UNK     0      -3.032  -6.065   0.000  0.00  0.00           H+0
HETATM   32  O   UNK     0      -1.698  -6.835   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8   31                                             
CONECT    6    1    5    7   19                                             
CONECT    7    6   12   10                                                  
CONECT    8    5    9   32                                                  
CONECT    9    8   10                                                       
CONECT   10    7    9   15                                                  
CONECT   11   12   14                                                       
CONECT   12    7   11                                                       
CONECT   13   14   22   17                                                  
CONECT   14   11   13   15   20                                             
CONECT   15   10   14   16                                                  
CONECT   16   15   17                                                       
CONECT   17   13   16                                                       
CONECT   18    3                                                            
CONECT   19    6                                                            
CONECT   20   14                                                            
CONECT   21   22   23                                                       
CONECT   22   13   21   28                                                  
CONECT   23   21   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   22                                                            
CONECT   29   24   30                                                       
CONECT   30   29                                                            
CONECT   31    5                                                            
CONECT   32    8                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
5a-Stigmast-22-ene-3,6-dione	Generator
5Α-stigmast-22-ene-3,6-dione	Generator

Chemical Formula

C₂₉H₄₆O₂

Average Mass

426.6743 Da

Monoisotopic Mass

426.34978 Da

IUPAC Name

(2R,7S,15R)-14-[(2R,3E,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,8-dione

Traditional Name

(2R,7S,15R)-14-[(2R,3E,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,8-dione

CAS Registry Number

Not Available

SMILES

CC[C@@H](C(C)C)\C=C\[C@@H](C)C1CCC2C3CC(=O)[C@@]4([H])CC(=O)CC[C@]4(C)C3CC[C@]12C

InChI Identifier

InChI=1S/C29H46O2/c1-7-20(18(2)3)9-8-19(4)23-10-11-24-22-17-27(31)26-16-21(30)12-14-29(26,6)25(22)13-15-28(23,24)5/h8-9,18-20,22-26H,7,10-17H2,1-6H3/b9-8+/t19-,20-,22?,23?,24?,25?,26-,28-,29-/m1/s1

InChI Key

FJQGCLCMDPGZHC-PVHRTUTRSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Phoenix dactylifera	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Stigmastanes and derivatives

Direct Parent

Stigmastanes and derivatives

Alternative Parents

Substituents

Triterpenoid
Stigmastane-skeleton
6-oxosteroid
3-oxo-5-alpha-steroid
Oxosteroid
3-oxosteroid
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	5.7	ALOGPS
logP	7.17	ChemAxon
logS	-7.1	ALOGPS
pKa (Strongest Acidic)	17.77	ChemAxon
pKa (Strongest Basic)	-7.1	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	5	ChemAxon
Refractivity	129.67 m³·mol⁻¹	ChemAxon
Polarizability	52.65 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

FDB006545

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

Not Available

Showing NP-Card for 5alpha-Stigmast-22-ene-3,6-dione (NP0046921)

MOL for NP0046921 (5alpha-Stigmast-22-ene-3,6-dione)

3D MOL for NP0046921 (5alpha-Stigmast-22-ene-3,6-dione)

3D SDF for NP0046921 (5alpha-Stigmast-22-ene-3,6-dione)

3D-SDF for NP0046921 (5alpha-Stigmast-22-ene-3,6-dione)

PDB for NP0046921 (5alpha-Stigmast-22-ene-3,6-dione)

3D PDB for NP0046921 (5alpha-Stigmast-22-ene-3,6-dione)

SMILES for NP0046921 (5alpha-Stigmast-22-ene-3,6-dione)

INCHI for NP0046921 (5alpha-Stigmast-22-ene-3,6-dione)

Structure for NP0046921 (5alpha-Stigmast-22-ene-3,6-dione)

3D Structure for NP0046921 (5alpha-Stigmast-22-ene-3,6-dione)