ChemFOnt: Showing chemical card for 2-trans-O-Feruloylglucaric acid (CFc000282062)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:34:03 UTC

Chemfont ID

CFc000282062

Molecule Identification

Common Name

2-trans-O-Feruloylglucaric acid

Definition

2-trans-o-feruloylglucaric acid belongs to glucuronic acid derivatives class of compounds. Those are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid. 2-trans-o-feruloylglucaric acid is slightly soluble (in water) and a moderately acidic compound (based on its pKa). 2-trans-o-feruloylglucaric acid can be found in sweet orange, which makes 2-trans-o-feruloylglucaric acid a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S,3S,4S,5R)-2,3,4-Trihydroxy-5-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}hexanedioate	Generator
2-trans-O-Feruloylglucarate	Generator

Chemical Formula

C₁₆H₁₈O₁₁

Average Molecular Weight

386.3075

Monoisotopic Molecular Weight

386.084911418

IUPAC Name

(2S,3S,4S,5R)-2,3,4-trihydroxy-5-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}hexanedioic acid

Traditional Name

(2S,3S,4S,5R)-2,3,4-trihydroxy-5-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}hexanedioic acid

CAS Registry Number

None

SMILES

COC1=C(O)C=CC(\C=C\C(=O)O[C@H]([C@@H](O)[C@H](O)[C@H](O)C(O)=O)C(O)=O)=C1

InChI Identifier

InChI=1S/C16H18O11/c1-26-9-6-7(2-4-8(9)17)3-5-10(18)27-14(16(24)25)12(20)11(19)13(21)15(22)23/h2-6,11-14,17,19-21H,1H3,(H,22,23)(H,24,25)/b5-3+/t11-,12-,13-,14+/m0/s1

InChI Key

JZRAOXRUPYISEN-GLJYKRHASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Glucuronic acid derivatives

Alternative Parents

Substituents

Glucuronic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid or derivatives
Cinnamic acid ester
Methoxyphenol
Tricarboxylic acid or derivatives
Phenoxy compound
Phenol ether
Methoxybenzene
Styrene
Anisole
Beta-hydroxy acid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acid ester
Alkyl aryl ether
Monosaccharide
Alpha-hydroxy acid
Hydroxy acid
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Polyol
Ether
Carbonyl group
Organic oxide
Alcohol
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302546)

Food

Fruit

Citrus

Sweet orange (FooDB: FOOD00057)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.78 g/L	ALOGPS
logP	0.71	ALOGPS
logP	-0.52	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	2.79	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	191.05 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	86.15 m³·mol⁻¹	ChemAxon
Polarizability	35.61 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0302546

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB005075

KNApSAcK ID

Not Available

Chemspider ID

59696348

KEGG Compound ID

Not Available

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 2-trans-O-Feruloylglucaric acid (CFc000282062)

MOL for CFc000282062 (2-trans-O-Feruloylglucaric acid)

3D MOL for CFc000282062 (2-trans-O-Feruloylglucaric acid)

3D SDF for CFc000282062 (2-trans-O-Feruloylglucaric acid)

3D-SDF for CFc000282062 (2-trans-O-Feruloylglucaric acid)

PDB for CFc000282062 (2-trans-O-Feruloylglucaric acid)

3D PDB for CFc000282062 (2-trans-O-Feruloylglucaric acid)

SMILES for CFc000282062 (2-trans-O-Feruloylglucaric acid)

INCHI for CFc000282062 (2-trans-O-Feruloylglucaric acid)

Structure for CFc000282062 (2-trans-O-Feruloylglucaric acid)

3D Structure for CFc000282062 (2-trans-O-Feruloylglucaric acid)