ChemFOnt: Showing chemical card for Deoxyloganic acid (CFc000017964)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:08:12 UTC

Chemfont ID

CFc000017964

Molecule Identification

Common Name

Deoxyloganic acid

Definition

Deoxyloganic acid is found in herbs and spices. Deoxyloganic acid is a constituent of Nepeta cataria (catnip).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Deoxyloganate	Generator
1,5,9-Epideoxyloganic acid	HMDB
5-Epideoxyloganic acid	HMDB
8-Epideoxyloganic acid	HMDB
Deoxyloganic acid tetraacetate	HMDB
7-Methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4ah,5H,6H,7H,7ah-cyclopenta[c]pyran-4-carboxylate	Generator
7-Deoxyloganic acid	MeSH
Deoxyloganic acid	MeSH

Chemical Formula

C₁₆H₂₄O₉

Average Molecular Weight

360.3564

Monoisotopic Molecular Weight

360.142032366

IUPAC Name

7-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylic acid

Traditional Name

7-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylic acid

CAS Registry Number

92842-56-3

SMILES

CC1CCC2C1C(OC1OC(CO)C(O)C(O)C1O)OC=C2C(O)=O

InChI Identifier

InChI=1S/C16H24O9/c1-6-2-3-7-8(14(21)22)5-23-15(10(6)7)25-16-13(20)12(19)11(18)9(4-17)24-16/h5-7,9-13,15-20H,2-4H2,1H3,(H,21,22)

InChI Key

DSXFHNSGLYXPNG-UHFFFAOYSA-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
Secondary alcohol
Acetal
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Polyol
Primary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037028)

Source

Endogenous

Endogenous (HMDB: HMDB0037028)

Plant

Plant (HMDB: HMDB0037028)

Animal

Animal (HMDB: HMDB0037028)

Exogenous

Food

Food (HMDB: HMDB0037028)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0037028)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0037028)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0037028)

Lipid metabolism pathway (HMDB: HMDB0037028)

Cellular process

Cell signaling (HMDB: HMDB0037028)

Biochemical process

Lipid transport (HMDB: HMDB0037028)

Role

Biological role

Energy source (HMDB: HMDB0037028)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037028)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	20.3 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-0.91	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	4.33	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	145.91 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	81.11 m³·mol⁻¹	ChemAxon
Polarizability	35.6 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