Showing Compound Verbenalin (FDB001521)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:00 UTC

Update date

2019-11-26 02:56:33 UTC

Primary ID

FDB001521

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Verbenalin

Description

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 .

CAS Number

548-37-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
Cornin (glycoside)	Kegg
Cornin iridoid	MeSH
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

Showing 1 to 3 of 3 entries

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

Chemical Formula

C17H24O10

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

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

Isomeric 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

Average Molecular Weight

388.3665

Monoisotopic Molecular Weight

388.136946988

Classification

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 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	211 mg/mL at 18 oC	BEILSTEIN
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01t9-0896000000-437cd88fa73a5c4d7b90	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06vj-0951000000-1242e64dbb52b6178f09	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kb-3920000000-da78294fdb00d24514e0	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004r-1589000000-d3de7f2ed7d905736e35	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-2963000000-a5eb145f50523b35dd20	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0036-8920000000-cae9774ae18e15ccbe46	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004r-0197000000-08dc874beea6d15b7630	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4l-0982000000-cccb82751b52776fa64a	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05r0-7792000000-390fc7ee43f9dc8ee78d	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0379000000-9c71e3d58bd848370ba7	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05ot-2944000000-ed555a3f148b5df753ed	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4m-9631000000-3f8cf1006bc884d2333e	2021-10-21	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

VERBENALIN

BIGG ID

Not Available

KNApSAcK ID

C00003102

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
abortifacient	50691	A chemical substance that interrupts pregnancy after implantation.	DUKE
cathartic	75325	Any substance that accelerates defecation. Compare with laxatives, which are substances that ease defecation (usually by softening faeces). A substance can be both a laxative and a cathartic.	DUKE
central nervous system stimulant	35470	A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.	DUKE
coagulant			DUKE
parasympathicomimetic			DUKE
purgative	50503	An agent that produces a soft formed stool, and relaxes and loosens the bowels, typically used over a protracted period, to relieve constipation. Compare with cathartic, which is a substance that accelerates defecation. A substances can be both a laxative and a cathartic.	DUKE
utero tonic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE