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Showing NP-Card for gamma-Taraxasterone (NP0048336)

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Record Information
Version2.0
Created at2022-03-17 20:54:50 UTC
Updated at2022-03-17 20:54:50 UTC
NP-MRD IDNP0048336
Secondary Accession NumbersNone
Natural Product Identification
Common Namegamma-Taraxasterone
DescriptionGamma-Taraxasterone, also known as γ-taraxasterone or 20-taraxasten-3-one, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Gamma-Taraxasterone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, gamma-Taraxasterone has been detected, but not quantified in, several different foods, such as alcoholic beverages, beverages, coffee and coffee products, and tea. gamma-Taraxasterone is found in Euphorbia cyparissias, Ixeris chinensis and Picris hieracioides. This could make gamma-taraxasterone a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0048336 (gamma-Taraxasterone)


  Mrv0541 05061308442D          

 31 35  0  0  0  0            999 V2000
    4.4782    2.5990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9071    1.7740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2347   -2.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2953   -2.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7638   -0.2885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0506   -0.2885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9072   -1.5260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6251   -0.4390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6216    0.5365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3361    0.1240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7637    1.3615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3361   -2.3510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4795   -1.1135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7637    0.5365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7650   -0.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6216   -1.9385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4782   -0.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1927   -1.1135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4782    1.7740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1927    1.3615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9071    0.1240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0505   -1.9385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3361   -0.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4795   -1.9385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1927    0.5365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7650   -2.3510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4782    0.1240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0506   -1.1135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9071   -0.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6216   -1.1135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1940   -2.3510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0  0  0  0
 14 11  1  0  0  0  0
 15 13  1  0  0  0  0
 16 12  1  0  0  0  0
 18 17  1  0  0  0  0
 19  1  1  0  0  0  0
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 20  2  1  0  0  0  0
 20 19  1  0  0  0  0
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 22 12  1  0  0  0  0
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 25 21  1  0  0  0  0
 26  3  1  0  0  0  0
 26  4  1  0  0  0  0
 26 22  1  0  0  0  0
 26 24  1  0  0  0  0
 27  5  1  0  0  0  0
 27 14  1  0  0  0  0
 27 17  1  0  0  0  0
 27 25  1  0  0  0  0
 28  6  1  0  0  0  0
 28 15  1  0  0  0  0
 28 22  1  0  0  0  0
 28 23  1  0  0  0  0
 29  7  1  0  0  0  0
 29 18  1  0  0  0  0
 29 21  1  0  0  0  0
 30  8  1  0  0  0  0
 30 16  1  0  0  0  0
 30 23  1  0  0  0  0
 30 29  1  0  0  0  0
 31 24  2  0  0  0  0
M  END
Download

3D MOL for NP0048336 (gamma-Taraxasterone)

Download
3D SDF for NP0048336 (gamma-Taraxasterone)

  Mrv0541 05061308442D          

 31 35  0  0  0  0            999 V2000
    4.4782    2.5990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9071    1.7740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2347   -2.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2953   -2.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7638   -0.2885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0506   -0.2885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9072   -1.5260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6251   -0.4390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6216    0.5365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3361    0.1240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7637    1.3615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3361   -2.3510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4795   -1.1135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7637    0.5365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7650   -0.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6216   -1.9385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4782   -0.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1927   -1.1135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4782    1.7740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1927    1.3615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9071    0.1240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0505   -1.9385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3361   -0.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4795   -1.9385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1927    0.5365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7650   -2.3510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4782    0.1240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0506   -1.1135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9071   -0.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6216   -1.1135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1940   -2.3510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0  0  0  0
 14 11  1  0  0  0  0
 15 13  1  0  0  0  0
 16 12  1  0  0  0  0
 18 17  1  0  0  0  0
 19  1  1  0  0  0  0
 19 11  2  0  0  0  0
 20  2  1  0  0  0  0
 20 19  1  0  0  0  0
 21  9  1  0  0  0  0
 22 12  1  0  0  0  0
 23 10  1  0  0  0  0
 24 13  1  0  0  0  0
 25 20  1  0  0  0  0
 25 21  1  0  0  0  0
 26  3  1  0  0  0  0
 26  4  1  0  0  0  0
 26 22  1  0  0  0  0
 26 24  1  0  0  0  0
 27  5  1  0  0  0  0
 27 14  1  0  0  0  0
 27 17  1  0  0  0  0
 27 25  1  0  0  0  0
 28  6  1  0  0  0  0
 28 15  1  0  0  0  0
 28 22  1  0  0  0  0
 28 23  1  0  0  0  0
 29  7  1  0  0  0  0
 29 18  1  0  0  0  0
 29 21  1  0  0  0  0
 30  8  1  0  0  0  0
 30 16  1  0  0  0  0
 30 23  1  0  0  0  0
 30 29  1  0  0  0  0
 31 24  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0048336

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2C3CCC4C5(C)CCC(=O)C(C)(C)C5CCC4(C)C3(C)CCC2(C)CC=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O/c1-19-11-14-27(5)17-18-29(7)21(25(27)20(19)2)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h11,20-23,25H,9-10,12-18H2,1-8H3

> <INCHI_KEY>
CJRZLPSJKBMUPM-UHFFFAOYSA-N

> <FORMULA>
C30H48O

> <MOLECULAR_WEIGHT>
424.7015

> <EXACT_MASS>
424.370516158

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
53.34173601580421

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,4,6a,6b,8a,11,12,14b-octamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,12,12a,12b,13,14,14a,14b-icosahydropicen-3-one

> <ALOGPS_LOGP>
6.60

> <JCHEM_LOGP>
7.953640516333333

> <ALOGPS_LOGS>
-7.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.962170442253317

> <JCHEM_PKA_STRONGEST_BASIC>
-7.47088496448267

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
131.15849999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.09e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,4,6a,6b,8a,11,12,14b-octamethyl-1,2,4a,5,6,7,8,9,12,12a,12b,13,14,14a-tetradecahydropicen-3-one

> <JCHEM_VEBER_RULE>
1

$$$$

Download
3D-SDF for NP0048336 (gamma-Taraxasterone)
Download
PDB for NP0048336 (gamma-Taraxasterone)
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       8.359   4.851   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.027   3.311   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.371  -5.568   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      17.351  -5.568   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.026  -0.539   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.028  -0.539   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.027  -2.849   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.367  -0.819   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.360   1.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.694   0.231   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.026   2.541   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.694  -4.389   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      17.695  -2.079   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.026   1.001   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.361  -1.309   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.360  -3.619   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.359  -1.309   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.693  -2.079   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.359   3.311   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.693   2.541   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.027   0.231   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.028  -3.619   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.694  -1.309   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.695  -3.619   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.693   1.001   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      16.361  -4.389   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.359   0.231   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.028  -2.079   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.027  -1.309   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.360  -2.079   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      19.029  -4.389   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   20                                                            
CONECT    3   26                                                            
CONECT    4   26                                                            
CONECT    5   27                                                            
CONECT    6   28                                                            
CONECT    7   29                                                            
CONECT    8   30                                                            
CONECT    9   10   21                                                       
CONECT   10    9   23                                                       
CONECT   11   14   19                                                       
CONECT   12   16   22                                                       
CONECT   13   15   24                                                       
CONECT   14   11   27                                                       
CONECT   15   13   28                                                       
CONECT   16   12   30                                                       
CONECT   17   18   27                                                       
CONECT   18   17   29                                                       
CONECT   19    1   11   20                                                  
CONECT   20    2   19   25                                                  
CONECT   21    9   25   29                                                  
CONECT   22   12   26   28                                                  
CONECT   23   10   28   30                                                  
CONECT   24   13   26   31                                                  
CONECT   25   20   21   27                                                  
CONECT   26    3    4   22   24                                             
CONECT   27    5   14   17   25                                             
CONECT   28    6   15   22   23                                             
CONECT   29    7   18   21   30                                             
CONECT   30    8   16   23   29                                             
CONECT   31   24                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

Download
3D PDB for NP0048336 (gamma-Taraxasterone)
Download
SMILES for NP0048336 (gamma-Taraxasterone)
CC1C2C3CCC4C5(C)CCC(=O)C(C)(C)C5CCC4(C)C3(C)CCC2(C)CC=C1C
Download
INCHI for NP0048336 (gamma-Taraxasterone)
InChI=1S/C30H48O/c1-19-11-14-27(5)17-18-29(7)21(25(27)20(19)2)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h11,20-23,25H,9-10,12-18H2,1-8H3
Download
View in JSmol
Synonyms
ValueSource
g-TaraxasteroneGenerator
Γ-taraxasteroneGenerator
20-Taraxasten-3-oneHMDB
PseudotaraxasteroneHMDB
Y-taraxasteroneHMDB
Chemical FormulaC30H48O
Average Mass424.7015 Da
Monoisotopic Mass424.37052 Da
IUPAC Name4,4,6a,6b,8a,11,12,14b-octamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,12,12a,12b,13,14,14a,14b-icosahydropicen-3-one
Traditional Name4,4,6a,6b,8a,11,12,14b-octamethyl-1,2,4a,5,6,7,8,9,12,12a,12b,13,14,14a-tetradecahydropicen-3-one
CAS Registry Number16054-73-2
SMILES
CC1C2C3CCC4C5(C)CCC(=O)C(C)(C)C5CCC4(C)C3(C)CCC2(C)CC=C1C
InChI Identifier
InChI=1S/C30H48O/c1-19-11-14-27(5)17-18-29(7)21(25(27)20(19)2)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h11,20-23,25H,9-10,12-18H2,1-8H3
InChI KeyCJRZLPSJKBMUPM-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Coffea arabica L.FooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephoraFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Euphorbia cyparissiasLOTUS Database
Ixeris chinensisLOTUS Database
Picris hieracioidesLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassTriterpenoids  
Direct ParentTriterpenoids  
Alternative Parents
Substituents
  • Triterpenoid
    • 

  • Cyclic ketone
    • 

  • Ketone
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
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
logP6.6ALOGPS
logP7.95ChemAxon
logS-7.1ALOGPS
pKa (Strongest Acidic)19.96ChemAxon
pKa (Strongest Basic)-7.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity131.16 m³·mol⁻¹ChemAxon
Polarizability53.34 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0035817  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014579  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131751867  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References