NP-MRD: Showing NP-Card for Stigmasta-4,6-dien-3-one (NP0049334)

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Record Information

Version

2.0

Created at

2022-03-17 21:10:49 UTC

Updated at

2022-03-17 21:10:49 UTC

NP-MRD ID

NP0049334

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Stigmasta-4,6-dien-3-one

Description

Stigmasta-4,6-dien-3-one 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. Stigmasta-4,6-dien-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, stigmasta-4,6-dien-3-one has been detected, but not quantified in, root vegetables and soy beans. Stigmasta-4,6-dien-3-one is found in Conium maculatum. This could make stigmasta-4,6-dien-3-one a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061310562D          

 30 33  0  0  0  0            999 V2000
    4.0644   -0.1252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3019   -2.2686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0644   -1.5541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7769   -0.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7797   -2.3127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3425   -1.5702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8894   -0.1252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5394   -1.5541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1269   -0.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5097   -4.4787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7251   -4.2237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4414   -3.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0545   -3.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3490   -2.8226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9951   -2.0578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5644   -2.5676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2105   -1.8028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9074   -4.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8894   -1.5541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3644   -1.5541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3019   -0.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1228   -3.9266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5205   -3.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5535   -3.4168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7769   -2.2686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7689   -3.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1666   -2.8647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9513   -3.1197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5974   -2.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3051   -3.8845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  9  8  1  0  0  0  0
 11 10  2  0  0  0  0
 13 12  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 19  2  1  0  0  0  0
 19  3  1  0  0  0  0
 20  4  1  0  0  0  0
 20  8  1  0  0  0  0
 21  7  1  0  0  0  0
 21  9  1  0  0  0  0
 21 19  1  0  0  0  0
 22 10  1  0  0  0  0
 22 18  2  0  0  0  0
 23 14  1  0  0  0  0
 23 18  1  0  0  0  0
 24 11  1  0  0  0  0
 25 12  1  0  0  0  0
 25 20  1  0  0  0  0
 26 13  1  0  0  0  0
 26 24  1  0  0  0  0
 27 15  1  0  0  0  0
 27 24  1  0  0  0  0
 28  5  1  0  0  0  0
 28 16  1  0  0  0  0
 28 22  1  0  0  0  0
 28 27  1  0  0  0  0
 29  6  1  0  0  0  0
 29 17  1  0  0  0  0
 29 25  1  0  0  0  0
 29 26  1  0  0  0  0
 30 23  2  0  0  0  0
M  END


  Mrv0541 05061310562D          

 30 33  0  0  0  0            999 V2000
    4.0644   -0.1252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3019   -2.2686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0644   -1.5541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7769   -0.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7797   -2.3127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3425   -1.5702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8894   -0.1252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5394   -1.5541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1269   -0.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5097   -4.4787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7251   -4.2237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4414   -3.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0545   -3.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3490   -2.8226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9951   -2.0578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5644   -2.5676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2105   -1.8028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9074   -4.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8894   -1.5541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3644   -1.5541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3019   -0.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1228   -3.9266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5205   -3.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5535   -3.4168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7769   -2.2686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7689   -3.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1666   -2.8647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9513   -3.1197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5974   -2.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3051   -3.8845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  9  8  1  0  0  0  0
 11 10  2  0  0  0  0
 13 12  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 19  2  1  0  0  0  0
 19  3  1  0  0  0  0
 20  4  1  0  0  0  0
 20  8  1  0  0  0  0
 21  7  1  0  0  0  0
 21  9  1  0  0  0  0
 21 19  1  0  0  0  0
 22 10  1  0  0  0  0
 22 18  2  0  0  0  0
 23 14  1  0  0  0  0
 23 18  1  0  0  0  0
 24 11  1  0  0  0  0
 25 12  1  0  0  0  0
 25 20  1  0  0  0  0
 26 13  1  0  0  0  0
 26 24  1  0  0  0  0
 27 15  1  0  0  0  0
 27 24  1  0  0  0  0
 28  5  1  0  0  0  0
 28 16  1  0  0  0  0
 28 22  1  0  0  0  0
 28 27  1  0  0  0  0
 29  6  1  0  0  0  0
 29 17  1  0  0  0  0
 29 25  1  0  0  0  0
 29 26  1  0  0  0  0
 30 23  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0049334

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(CCC(C)C1CCC2C3C=CC4=CC(=O)CCC4(C)C3CCC12C)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C29H46O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10-11,18-21,24-27H,7-9,12-17H2,1-6H3

> <INCHI_KEY>
KEAZWUZFBSXOMV-UHFFFAOYSA-N

> <FORMULA>
C29H46O

> <MOLECULAR_WEIGHT>
410.6749

> <EXACT_MASS>
410.354866094

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
52.291170859259125

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
14-(5-ethyl-6-methylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-6,8-dien-5-one

> <ALOGPS_LOGP>
6.80

> <JCHEM_LOGP>
8.049801083333335

> <ALOGPS_LOGS>
-7.41

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.938628620851844

> <JCHEM_PKA_STRONGEST_BASIC>
-4.773828935718656

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
129.83129999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.61e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-(5-ethyl-6-methylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-6,8-dien-5-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       7.587  -0.234   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.897  -4.235   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.587  -2.901   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.517  -1.567   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.122  -4.317   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.573  -2.931   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.127  -0.234   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.207  -2.901   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.437  -1.567   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.618  -8.360   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.154  -7.884   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.891  -5.642   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.035  -6.672   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      23.051  -5.269   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      18.658  -3.841   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      21.587  -4.793   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.193  -3.365   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      22.227  -7.806   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.127  -2.901   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.747  -2.901   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.897  -1.567   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      20.763  -7.330   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      23.372  -6.775   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.833  -6.378   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.517  -4.235   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      16.369  -5.902   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      18.978  -5.347   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      20.442  -5.823   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      16.048  -4.396   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      24.836  -7.251   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2   19                                                            
CONECT    3   19                                                            
CONECT    4   20                                                            
CONECT    5   28                                                            
CONECT    6   29                                                            
CONECT    7    1   21                                                       
CONECT    8    9   20                                                       
CONECT    9    8   21                                                       
CONECT   10   11   22                                                       
CONECT   11   10   24                                                       
CONECT   12   13   25                                                       
CONECT   13   12   26                                                       
CONECT   14   16   23                                                       
CONECT   15   17   27                                                       
CONECT   16   14   28                                                       
CONECT   17   15   29                                                       
CONECT   18   22   23                                                       
CONECT   19    2    3   21                                                  
CONECT   20    4    8   25                                                  
CONECT   21    7    9   19                                                  
CONECT   22   10   18   28                                                  
CONECT   23   14   18   30                                                  
CONECT   24   11   26   27                                                  
CONECT   25   12   20   29                                                  
CONECT   26   13   24   29                                                  
CONECT   27   15   24   28                                                  
CONECT   28    5   16   22   27                                             
CONECT   29    6   17   25   26                                             
CONECT   30   23                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
24-Ethylcholesta-4,6-dien-3-one	HMDB

Chemical Formula

C₂₉H₄₆O

Average Mass

410.6749 Da

Monoisotopic Mass

410.35487 Da

IUPAC Name

14-(5-ethyl-6-methylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-6,8-dien-5-one

Traditional Name

14-(5-ethyl-6-methylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-6,8-dien-5-one

CAS Registry Number

29374-98-9

SMILES

CCC(CCC(C)C1CCC2C3C=CC4=CC(=O)CCC4(C)C3CCC12C)C(C)C

InChI Identifier

InChI=1S/C29H46O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10-11,18-21,24-27H,7-9,12-17H2,1-6H3

InChI Key

KEAZWUZFBSXOMV-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Conium maculatum	LOTUS Database	35616633
Glycine max	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

Not Available

Substituents

Not Available

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	6.8	ALOGPS
logP	8.05	ChemAxon
logS	-7.4	ALOGPS
pKa (Strongest Acidic)	19.94	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	129.83 m³·mol⁻¹	ChemAxon
Polarizability	52.29 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	Yes	ChemAxon

External Links

HMDB ID

HMDB0039196

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018724

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

12943206

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Stigmasta-4,6-dien-3-one (NP0049334)

MOL for NP0049334 (Stigmasta-4,6-dien-3-one)

3D MOL for NP0049334 (Stigmasta-4,6-dien-3-one)

3D SDF for NP0049334 (Stigmasta-4,6-dien-3-one)

3D-SDF for NP0049334 (Stigmasta-4,6-dien-3-one)

PDB for NP0049334 (Stigmasta-4,6-dien-3-one)

3D PDB for NP0049334 (Stigmasta-4,6-dien-3-one)

SMILES for NP0049334 (Stigmasta-4,6-dien-3-one)

INCHI for NP0049334 (Stigmasta-4,6-dien-3-one)

Structure for NP0049334 (Stigmasta-4,6-dien-3-one)

3D Structure for NP0049334 (Stigmasta-4,6-dien-3-one)