ChemFOnt: Showing chemical card for Verbenalin (CFc000281369)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:32:41 UTC

Chemfont ID

CFc000281369

Molecule Identification

Common Name

Verbenalin

Definition

Verbenalin, also known as cornin (glycoside) or cornin iridoid, is a member of the class of compounds known as iridoid o-glycosides. Iridoid o-glycosides are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton. Thus, verbenalin is considered to be an isoprenoid lipid molecule. Verbenalin is soluble (in water) and a very weakly acidic compound (based on its pKa). Verbenalin is a bitter tasting compound found in common verbena, which makes verbenalin a potential biomarker for the consumption of this food product. Verbenalin is a chemical compound, classified as an iridoid glucoside, that is found in Verbena officinalis. It is one of the sleep-promoting (soporific) components in Verbena officinalis .

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Cornin (glycoside)	Kegg
Methyl (1S,4as,7S,7ar)-7-methyl-5-oxo-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4ah,5H,6H,7H,7ah-cyclopenta[c]pyran-4-carboxylic acid	Generator
Cornin iridoid	MeSH

Chemical Formula

C₁₇H₂₄O₁₀

Average Molecular Weight

388.3665

Monoisotopic Molecular Weight

388.136946988

IUPAC Name

methyl (1S,4aS,7S,7aR)-7-methyl-5-oxo-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate

Traditional Name

cornin

CAS Registry Number

548-37-8

SMILES

COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H]2[C@@H](C)CC(=O)[C@H]12

InChI Identifier

InChI=1S/C17H24O10/c1-6-3-8(19)11-7(15(23)24-2)5-25-16(10(6)11)27-17-14(22)13(21)12(20)9(4-18)26-17/h5-6,9-14,16-18,20-22H,3-4H2,1-2H3/t6-,9+,10+,11-,12+,13-,14+,16-,17-/m0/s1

InChI Key

HLXRWTJXGMHOFN-XJSNKYLASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Iridoid O-glycosides

Alternative Parents

Substituents

Iridoid o-glycoside
Hexose monosaccharide
Glycosyl compound
Iridoid-skeleton
O-glycosyl compound
Bicyclic monoterpenoid
Monoterpenoid
Monosaccharide
Oxane
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Secondary alcohol
Ketone
Carboxylic acid ester
Polyol
Carboxylic acid derivative
Acetal
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Carbonyl group
Organooxygen compound
Primary alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

terpene glycoside (CHEBI:9954 )
Iridoid, 10-alkyliridoid and secoiridoid monoterpenoids (C09802 )
Iridoids (C09802 )
Iridoid, 10-alkyliridoid and secoiridoid monoterpenoids (LMPR0102070016 )

Functional Ontology

Physiological effect

Organoleptic effect

Taste

Bitter

Disposition

Source

Exogenous

Exogenous (HMDB: HMDB0301853)

Food

Herb and spice

Herb

Common verbena (FooDB: FOOD00196)

Process

Not Available

Role

Industrial application

Abortifacient (HMDB: HMDB0301853)
Central nervous system stimulant (HMDB: HMDB0301853)

Biological role

Cathartic (HMDB: HMDB0301853)
Coagulant (HMDB: HMDB0301853)
Parasympathicomimetic (HMDB: HMDB0301853)
Purgative (HMDB: HMDB0301853)
Utero tonic (HMDB: HMDB0301853)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	33 g/L	ALOGPS
logP	-0.93	ALOGPS
logP	-1.5	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	10.23	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	151.98 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	86.55 m³·mol⁻¹	ChemAxon
Polarizability	37.7 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0301853

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

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

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Verbenalin (CFc000281369)

MOL for CFc000281369 (Verbenalin)

3D MOL for CFc000281369 (Verbenalin)

3D SDF for CFc000281369 (Verbenalin)

3D-SDF for CFc000281369 (Verbenalin)

PDB for CFc000281369 (Verbenalin)

3D PDB for CFc000281369 (Verbenalin)

SMILES for CFc000281369 (Verbenalin)

INCHI for CFc000281369 (Verbenalin)

Structure for CFc000281369 (Verbenalin)

3D Structure for CFc000281369 (Verbenalin)