ChemFOnt: Showing chemical card for 1-Menthyl-beta-D-glucoside (CFc000334176)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:15:03 UTC

Chemfont ID

CFc000334176

Molecule Identification

Common Name

1-Menthyl-beta-D-glucoside

Definition

1-menthyl-beta-d-glucoside, also known as (-)-menthyl o-β-glucopyranoside, is a member of the class of compounds known as terpene glycosides. Terpene glycosides are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. Thus, 1-menthyl-beta-d-glucoside is considered to be an isoprenoid lipid molecule. 1-menthyl-beta-d-glucoside is soluble (in water) and a very weakly acidic compound (based on its pKa). 1-menthyl-beta-d-glucoside can be found in peppermint, which makes 1-menthyl-beta-d-glucoside a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-Menthyl O-beta-glucopyranoside	ChEBI
(-)-Menthyl O-beta-D-glucoside	ChEBI
(-)-Menthyl O-b-glucopyranoside	Generator
(-)-Menthyl O-β-glucopyranoside	Generator
(-)-Menthyl O-b-D-glucoside	Generator
(-)-Menthyl O-β-D-glucoside	Generator
Menthyl pyrrolidone carboxylic acid	Generator
(-)-Menthyl b-D-glucoside	HMDB
(-)-Menthyl β-D-glucoside	HMDB
1-Menthyl-b-D-glucoside	HMDB
1-Menthyl-β-D-glucoside	HMDB

Chemical Formula

C₁₆H₃₀O₆

Average Molecular Weight

318.4058

Monoisotopic Molecular Weight

318.204238692

IUPAC Name

(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]oxy}oxane-3,4,5-triol

Traditional Name

(-)-menthyl β-D-glucoside

CAS Registry Number

52528-10-6

SMILES

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

InChI Identifier

InChI=1S/C16H30O6/c1-8(2)10-5-4-9(3)6-11(10)21-16-15(20)14(19)13(18)12(7-17)22-16/h8-20H,4-7H2,1-3H3/t9-,10+,11-,12-,13-,14+,15-,16-/m1/s1

InChI Key

GZSDZJZIZBGBON-NZZARTGWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Glycosyl compound
O-glycosyl compound
Monocyclic monoterpenoid
Monoterpenoid
P-menthane monoterpenoid
Oxane
Monosaccharide
Secondary alcohol
Polyol
Acetal
Oxacycle
Organoheterocyclic compound
Primary alcohol
Organooxygen compound
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:15411 )
Menthane monoterpenoids (C03962 )
Menthane monoterpenoids (LMPR0102090060 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032368)

Source

Endogenous

Endogenous (HMDB: HMDB0032368)

Animal

Animal (HMDB: HMDB0032368)

Exogenous

Food

Food (HMDB: HMDB0032368)

Herb and spice

Herb

Peppermint (FooDB: FOOD00113)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0032368)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0032368)

Lipid metabolism pathway (HMDB: HMDB0032368)

Cellular process

Cell signaling (HMDB: HMDB0032368)

Biochemical process

Lipid transport (HMDB: HMDB0032368)

Role

Biological role

Energy source (HMDB: HMDB0032368)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0032368)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	12.2 g/L	ALOGPS
logP	0.47	ALOGPS
logP	0.89	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.38 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	79.86 m³·mol⁻¹	ChemAxon
Polarizability	34.44 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0032368

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB006135

KNApSAcK ID

Not Available

Chemspider ID

4573550

KEGG Compound ID

C03962

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5459767

PDB ID

Not Available

ChEBI ID

15411

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 1-Menthyl-beta-D-glucoside (CFc000334176)

MOL for CFc000334176 (1-Menthyl-beta-D-glucoside)

3D MOL for CFc000334176 (1-Menthyl-beta-D-glucoside)

3D SDF for CFc000334176 (1-Menthyl-beta-D-glucoside)

3D-SDF for CFc000334176 (1-Menthyl-beta-D-glucoside)

PDB for CFc000334176 (1-Menthyl-beta-D-glucoside)

3D PDB for CFc000334176 (1-Menthyl-beta-D-glucoside)

SMILES for CFc000334176 (1-Menthyl-beta-D-glucoside)

INCHI for CFc000334176 (1-Menthyl-beta-D-glucoside)

Structure for CFc000334176 (1-Menthyl-beta-D-glucoside)

3D Structure for CFc000334176 (1-Menthyl-beta-D-glucoside)