ChemFOnt: Showing chemical card for 2-O-Caffeoylhydroxycitric acid (CFc000021444)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:13:15 UTC

Chemfont ID

CFc000021444

Molecule Identification

Common Name

2-O-Caffeoylhydroxycitric acid

Definition

2-O-Caffeoylhydroxycitric acid is found in cereals and cereal products. 2-O-Caffeoylhydroxycitric acid is a constituent of Spondias mombin (yellow mombin) and Zea mays (sweet corn).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-O-Caffeoylhydroxycitrate	Generator
1-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-2-hydroxypropane-1,2,3-tricarboxylate	HMDB

Chemical Formula

C₁₅H₁₄O₁₁

Average Molecular Weight

370.2651

Monoisotopic Molecular Weight

370.05361129

IUPAC Name

1-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-2-hydroxypropane-1,2,3-tricarboxylic acid

Traditional Name

1-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-2-hydroxypropane-1,2,3-tricarboxylic acid

CAS Registry Number

62345-87-3

SMILES

OC(=O)CC(O)(C(OC(=O)\C=C\C1=CC(O)=C(O)C=C1)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C15H14O11/c16-8-3-1-7(5-9(8)17)2-4-11(20)26-12(13(21)22)15(25,14(23)24)6-10(18)19/h1-5,12,16-17,25H,6H2,(H,18,19)(H,21,22)(H,23,24)/b4-2+

InChI Key

OUWOVSUGDPWIBY-DUXPYHPUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Coumaric acid or derivatives
Cinnamic acid or derivatives
Styrene
Catechol
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
1-hydroxy-4-unsubstituted benzenoid
Phenol
Monosaccharide
Monocyclic benzene moiety
Alpha-hydroxy acid
Hydroxy acid
Benzenoid
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Carboxylic acid ester
Carboxylic acid
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0040572)
Cytoplasm (HMDB: HMDB0040572)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040572)

Source

Exogenous

Exogenous (HMDB: HMDB0040572)

Food

Food (HMDB: HMDB0040572)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereal

Corn (FooDB: FOOD00205)

Cereals and cereal products (FooDB: FOOD00858)

Fruit

Fruits (FooDB: FOOD00871)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Endogenous

Plant

Plant (HMDB: HMDB0040572)
Poaceae (HMDB: HMDB0040572)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0040572)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.21 g/L	ALOGPS
logP	1.45	ALOGPS
logP	0.39	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	2.87	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	198.89 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	80.49 m³·mol⁻¹	ChemAxon
Polarizability	32.65 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0040572

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB020350

KNApSAcK ID

C00054230

Chemspider ID

35014965

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24797519

PDB ID

Not Available

ChEBI ID

169788

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 2-O-Caffeoylhydroxycitric acid (CFc000021444)

MOL for CFc000021444 (2-O-Caffeoylhydroxycitric acid)

3D MOL for CFc000021444 (2-O-Caffeoylhydroxycitric acid)

3D SDF for CFc000021444 (2-O-Caffeoylhydroxycitric acid)

3D-SDF for CFc000021444 (2-O-Caffeoylhydroxycitric acid)

PDB for CFc000021444 (2-O-Caffeoylhydroxycitric acid)

3D PDB for CFc000021444 (2-O-Caffeoylhydroxycitric acid)

SMILES for CFc000021444 (2-O-Caffeoylhydroxycitric acid)

INCHI for CFc000021444 (2-O-Caffeoylhydroxycitric acid)

Structure for CFc000021444 (2-O-Caffeoylhydroxycitric acid)

3D Structure for CFc000021444 (2-O-Caffeoylhydroxycitric acid)