ChemFOnt: Showing chemical card for 12-Hydroxyjasmonic acid glucoside (CFc000281353)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:32:39 UTC

Chemfont ID

CFc000281353

Molecule Identification

Common Name

12-Hydroxyjasmonic acid glucoside

Definition

12-hydroxyjasmonic acid glucoside, also known as tuberonic acid beta-D-glucoside, is a member of the class of compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. 12-hydroxyjasmonic acid glucoside is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 12-hydroxyjasmonic acid glucoside can be found in potato, which makes 12-hydroxyjasmonic acid glucoside a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-[(1R,2R)-3-oxo-2-[(2Z)-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pent-2-en-1-yl]cyclopentyl]acetate	Generator
12-Hydroxyjasmonate glucoside	Generator

Chemical Formula

C₁₈H₂₈O₉

Average Molecular Weight

388.4095

Monoisotopic Molecular Weight

388.173332494

IUPAC Name

2-[(1R,2R)-3-oxo-2-[(2Z)-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pent-2-en-1-yl]cyclopentyl]acetic acid

Traditional Name

tuberonic acid glucoside

CAS Registry Number

120399-24-8

SMILES

OC[C@H]1O[C@@H](OCC\C=C/C[C@@H]2[C@@H](CC(O)=O)CCC2=O)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C18H28O9/c19-9-13-15(23)16(24)17(25)18(27-13)26-7-3-1-2-4-11-10(8-14(21)22)5-6-12(11)20/h1-2,10-11,13,15-19,23-25H,3-9H2,(H,21,22)/b2-1-/t10-,11-,13-,15-,16+,17-,18-/m1/s1

InChI Key

JFDNMLUPLXZXGV-RKAGECJXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

Fatty acyl glycoside of mono- or disaccharide
Jasmonic acid
Alkyl glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Monosaccharide
Oxane
Ketone
Cyclic ketone
Secondary alcohol
Monocarboxylic acid or derivatives
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Polyol
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
Primary alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Fatty acyl glycosides of mono- and disaccharides (C08558 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301837)

Food

Vegetable

Tuber

Potato (FooDB: FOOD00175)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.79 g/L	ALOGPS
logP	-0.28	ALOGPS
logP	-0.79	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	4.46	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	153.75 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	92.9 m³·mol⁻¹	ChemAxon
Polarizability	39.54 Å³	ChemAxon
Number of Rings	2	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

HMDB0301837

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 12-Hydroxyjasmonic acid glucoside (CFc000281353)

MOL for CFc000281353 (12-Hydroxyjasmonic acid glucoside)

3D MOL for CFc000281353 (12-Hydroxyjasmonic acid glucoside)

3D SDF for CFc000281353 (12-Hydroxyjasmonic acid glucoside)

3D-SDF for CFc000281353 (12-Hydroxyjasmonic acid glucoside)

PDB for CFc000281353 (12-Hydroxyjasmonic acid glucoside)

3D PDB for CFc000281353 (12-Hydroxyjasmonic acid glucoside)

SMILES for CFc000281353 (12-Hydroxyjasmonic acid glucoside)

INCHI for CFc000281353 (12-Hydroxyjasmonic acid glucoside)

Structure for CFc000281353 (12-Hydroxyjasmonic acid glucoside)

3D Structure for CFc000281353 (12-Hydroxyjasmonic acid glucoside)