ChemFOnt: Showing chemical card for Geniposidic acid (CFc000015959)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:05:20 UTC

Chemfont ID

CFc000015959

Molecule Identification

Common Name

Geniposidic acid

Definition

Geniposidic acid is found in beverages. Geniposidic acid is a constituent of Genipa americana (genipap)

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Geniposidate	Generator
7-(Hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4ah,5H,7ah-cyclopenta[c]pyran-4-carboxylate	HMDB

Chemical Formula

C₁₆H₂₂O₁₀

Average Molecular Weight

374.3399

Monoisotopic Molecular Weight

374.121296924

IUPAC Name

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

Traditional Name

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

CAS Registry Number

27741-01-1

SMILES

OCC1OC(OC2OC=C(C3CC=C(CO)C23)C(O)=O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C16H22O10/c17-3-6-1-2-7-8(14(22)23)5-24-15(10(6)7)26-16-13(21)12(20)11(19)9(4-18)25-16/h1,5,7,9-13,15-21H,2-4H2,(H,22,23)

InChI Key

ZJDOESGVOWAULF-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: HMDB0034942)

Source

Endogenous

Endogenous (HMDB: HMDB0034942)

Plant

Plant (HMDB: HMDB0034942)

Animal

Animal (HMDB: HMDB0034942)

Exogenous

Food

Food (HMDB: HMDB0034942)

Fruit

Fruits (FooDB: FOOD00871)

Beverage

Beverages (FooDB: FOOD00870)

Exogenous (HMDB: HMDB0034942)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0034942)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0034942)

Lipid metabolism pathway (HMDB: HMDB0034942)

Cellular process

Cell signaling (HMDB: HMDB0034942)

Biochemical process

Lipid transport (HMDB: HMDB0034942)

Role

Biological role

Energy source (HMDB: HMDB0034942)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0034942)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	22.5 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-2.6	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	4.22	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	166.14 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	83.74 m³·mol⁻¹	ChemAxon
Polarizability	35.58 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon