ChemFOnt: Showing chemical card for Neoisodihydrocarveol (CFc000282011)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:33:57 UTC

Chemfont ID

CFc000282011

Molecule Identification

Common Name

Neoisodihydrocarveol

Definition

Neoisodihydrocarveol, also known as (1s,2r,4r)-neoiso-dihydrocarveol or (1r,2s,5r)-5-isopropenyl-2-methylcyclohexanol, 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. Thus, neoisodihydrocarveol is considered to be an isoprenoid lipid molecule. Neoisodihydrocarveol is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). Neoisodihydrocarveol can be found in caraway and wild celery, which makes neoisodihydrocarveol a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(1R,2S,5R)-5-Isopropenyl-2-methylcyclohexanol	ChEBI
(1S,2R,4R)-Neoiso-dihydrocarveol	ChEBI
(1S,2R,4R)-Neoisodihydrocarveol	ChEBI

Chemical Formula

C₁₀H₁₈O

Average Molecular Weight

154.2493

Monoisotopic Molecular Weight

154.135765198

IUPAC Name

(1R,2S,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-ol

Traditional Name

(+)-neoisodihydrocarveol

CAS Registry Number

18675-34-8

SMILES

C[C@H]1CC[C@H](C[C@H]1O)C(C)=C

InChI Identifier

InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)10(11)6-9/h8-11H,1,4-6H2,2-3H3/t8-,9+,10+/m0/s1

InChI Key

KRCZYMFUWVJCLI-IVZWLZJFSA-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
Cyclohexanol
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

dihydrocarveol (CHEBI:50232 )
Menthane monoterpenoids (C11400 )
Cyclic monoterpenes (C11400 )
Menthane monoterpenoids (LMPR0102090035 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302495)

Food

Herb and spice

Spice

Wild celery (FooDB: FOOD00015)
Caraway (FooDB: FOOD00043)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.32 g/L	ALOGPS
logP	2.7	ALOGPS
logP	2.32	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	18.99	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	47.22 m³·mol⁻¹	ChemAxon
Polarizability	18.82 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

HMDB0302495

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB004797

KNApSAcK ID

Not Available

Chemspider ID

391438

KEGG Compound ID

C11400

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

50232

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Neoisodihydrocarveol (CFc000282011)

MOL for CFc000282011 (Neoisodihydrocarveol)

3D MOL for CFc000282011 (Neoisodihydrocarveol)

3D SDF for CFc000282011 (Neoisodihydrocarveol)

3D-SDF for CFc000282011 (Neoisodihydrocarveol)

PDB for CFc000282011 (Neoisodihydrocarveol)

3D PDB for CFc000282011 (Neoisodihydrocarveol)

SMILES for CFc000282011 (Neoisodihydrocarveol)

INCHI for CFc000282011 (Neoisodihydrocarveol)

Structure for CFc000282011 (Neoisodihydrocarveol)

3D Structure for CFc000282011 (Neoisodihydrocarveol)