NP-MRD: Showing NP-Card for Aubergenone (NP0048341)

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Record Information

Version

2.0

Created at

2022-03-17 20:54:55 UTC

Updated at

2022-03-17 20:54:55 UTC

NP-MRD ID

NP0048341

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aubergenone

Description

Aubergenone, also known as mangeudesmenone, belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. Aubergenone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Aubergenone has been detected, but not quantified in, a few different foods, such as eggplants, fruits, and green vegetables. Aubergenone is found in Mangifera indica , Nicotiana undulata and Solanum melogena. This could make aubergenone a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061308442D          

 17 18  0  0  0  0            999 V2000
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
 10  1  1  0  0  0  0
 11  5  1  0  0  0  0
 11  9  1  0  0  0  0
 12  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13  6  1  0  0  0  0
 13 10  1  0  0  0  0
 14  2  1  0  0  0  0
 14  3  1  0  0  0  0
 14 11  1  0  0  0  0
 15  4  1  0  0  0  0
 15  7  1  0  0  0  0
 15  8  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  2  0  0  0  0
 17 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048341

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2CC(CCC2(C)C=CC1=O)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O2/c1-10-12-9-11(14(2,3)17)5-7-15(12,4)8-6-13(10)16/h6,8,10-12,17H,5,7,9H2,1-4H3

> <INCHI_KEY>
MSSWKGZMPUXALD-UHFFFAOYSA-N

> <FORMULA>
C15H24O2

> <MOLECULAR_WEIGHT>
236.3499

> <EXACT_MASS>
236.177630012

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.65555525310669

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-one

> <ALOGPS_LOGP>
2.93

> <JCHEM_LOGP>
2.9539466753333325

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.24787634115214

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9407363492797732

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
70.34459999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.82e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-1,5,6,7,8,8a-hexahydronaphthalen-2-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       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.104  -2.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.564   0.564   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   14                                                            
CONECT    3   14                                                            
CONECT    4   15                                                            
CONECT    5    7   11                                                       
CONECT    6    8   13                                                       
CONECT    7    5   15                                                       
CONECT    8    6   15                                                       
CONECT    9   11   12                                                       
CONECT   10    1   12   13                                                  
CONECT   11    5    9   14                                                  
CONECT   12    9   10   15                                                  
CONECT   13    6   10   16                                                  
CONECT   14    2    3   11   17                                             
CONECT   15    4    7    8   12                                             
CONECT   16   13                                                            
CONECT   17   14                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Value	Source
Mangeudesmenone	HMDB
[1R-(1alpha,4Aalpha,7alpha,8abeta)]-4a,5,6,7,8,8a-hexahydro-7-(1-hydroxy-1-methylethyl)-1,4a-dimethyl-2(1H)-naphthalenone	HMDB

Chemical Formula

C₁₅H₂₄O₂

Average Mass

236.3499 Da

Monoisotopic Mass

236.17763 Da

IUPAC Name

7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-one

Traditional Name

7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-1,5,6,7,8,8a-hexahydronaphthalen-2-one

CAS Registry Number

69427-35-6

SMILES

CC1C2CC(CCC2(C)C=CC1=O)C(C)(C)O

InChI Identifier

InChI=1S/C15H24O2/c1-10-12-9-11(14(2,3)17)5-7-15(12,4)8-6-13(10)16/h6,8,10-12,17H,5,7,9H2,1-4H3

InChI Key

MSSWKGZMPUXALD-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Mangifera indica	Plant	KNApSAcK
Nicotiana undulata	LOTUS Database	35616633
Solanum melogena	Plant	KNApSAcK
Solanum melongena	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids

Alternative Parents

Substituents

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid
Cyclohexenone
Tertiary alcohol
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	2.93	ALOGPS
logP	2.95	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	19.25	ChemAxon
pKa (Strongest Basic)	-0.94	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	70.34 m³·mol⁻¹	ChemAxon
Polarizability	27.66 Å³	ChemAxon
Number of Rings	2	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

HMDB0035827

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014591

KNApSAcK ID

C00012854

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

15601417

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Aubergenone (NP0048341)

MOL for NP0048341 (Aubergenone)

3D MOL for NP0048341 (Aubergenone)

3D SDF for NP0048341 (Aubergenone)

3D-SDF for NP0048341 (Aubergenone)

PDB for NP0048341 (Aubergenone)

3D PDB for NP0048341 (Aubergenone)

SMILES for NP0048341 (Aubergenone)

INCHI for NP0048341 (Aubergenone)

Structure for NP0048341 (Aubergenone)

3D Structure for NP0048341 (Aubergenone)