ChemFOnt: Showing chemical card for Isopulegone (CFc000335905)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:28:44 UTC

Chemfont ID

CFc000335905

Molecule Identification

Common Name

Isopulegone

Definition

(-)-trans-isopulegone, also known as isopulegone or 1-methyl-4-isopropenyl-3-cyclohexanone, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes (-)-trans-isopulegone is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). (-)-trans-isopulegone can be found in fats and oils, which makes (-)-trans-isopulegone a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Methyl-4-isopropenyl-3-cyclohexanone	ChEBI
Isopulegone	ChEBI
(+)-Isopulegone	HMDB
(-)-trans-P-Menth-8-en-3-one	HMDB
(2R-trans)-5-Methyl-2-(1-methylethenyl)-cyclohexanone	HMDB
Pulegone, (S)-isomer	MeSH, HMDB
Pulegone, (R)-isomer	MeSH, HMDB
Pulegone	MeSH, HMDB
cis-Isopulegone	MeSH, HMDB

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

IUPAC Name

5-methyl-2-(prop-1-en-2-yl)cyclohexan-1-one

Traditional Name

isopulegone

CAS Registry Number

529-00-0

SMILES

CC1CCC(C(C)=C)C(=O)C1

InChI Identifier

InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8-9H,1,4-6H2,2-3H3

InChI Key

RMIANEGNSBUGDJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane monoterpenoids

Alternative Parents

Substituents

P-menthane monoterpenoid
Monocyclic monoterpenoid
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

p-menthane monoterpenoid (CHEBI:37046 )
a monoterpenoid (CPD-4941 )

Functional Ontology

Exogenous (HMDB: HMDB0035741)

Food

Herb and spice

Spice

Wild celery (FooDB: FOOD00015)

Herb

Cornmint (FooDB: FOOD00111)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavor (HMDB: HMDB0035741)

Fragrance (HMDB: HMDB0035741)

Biological role

Hepatotoxic agent (HMDB: HMDB0035741)
Pulmonotoxic (HMDB: HMDB0035741)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.54 g/L	ALOGPS
logP	2.42	ALOGPS
logP	2.7	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	17.88	ChemAxon
pKa (Strongest Basic)	-7.5	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	1	ChemAxon
Refractivity	46.3 m³·mol⁻¹	ChemAxon
Polarizability	18.26 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0035741

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB014470

KNApSAcK ID

C00010948

Chemspider ID

31884

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

34645

PDB ID

Not Available

ChEBI ID

37046

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Isopulegone (CFc000335905)

MOL for CFc000335905 (Isopulegone)

3D MOL for CFc000335905 (Isopulegone)

3D SDF for CFc000335905 (Isopulegone)

3D-SDF for CFc000335905 (Isopulegone)

PDB for CFc000335905 (Isopulegone)

3D PDB for CFc000335905 (Isopulegone)

SMILES for CFc000335905 (Isopulegone)

INCHI for CFc000335905 (Isopulegone)

Structure for CFc000335905 (Isopulegone)

3D Structure for CFc000335905 (Isopulegone)