ChemFOnt: Showing chemical card for cis-Caftaric acid (CFc000282576)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:35:03 UTC

Chemfont ID

CFc000282576

Molecule Identification

Common Name

cis-Caftaric acid

Definition

Cis-caftaric acid, also known as (2s,3r)-cis-caffeoyl tartaric acid or cis-caftarate, belongs to coumaric acids and derivatives class of compounds. Those are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Cis-caftaric acid is practically insoluble (in water) and a moderately acidic compound (based on its pKa). Cis-caftaric acid can be found in common grape, which makes cis-caftaric acid a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S,3R)-cis-Caffeoyl tartaric acid	ChEBI
cis-Caftaric acid	ChEBI
(2S,3R)-cis-Caffeoyl tartarate	Generator
cis-Caftarate	Generator
(2S,3R)-cis-Caftarate	Generator

Chemical Formula

C₁₃H₁₂O₉

Average Molecular Weight

312.23

Monoisotopic Molecular Weight

312.048131966

IUPAC Name

(2S,3R)-2-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioic acid

Traditional Name

(2S,3R)-2-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioic acid

CAS Registry Number

None

SMILES

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

InChI Identifier

InChI=1S/C13H12O9/c14-7-3-1-6(5-8(7)15)2-4-9(16)22-11(13(20)21)10(17)12(18)19/h1-5,10-11,14-15,17H,(H,18,19)(H,20,21)/b4-2-/t10-,11+/m1/s1

InChI Key

SWGKAHCIOQPKFW-ADAMHKFESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

catechols (CHEBI:76082 )
cinnamate ester (CHEBI:76082 )
dicarboxylic acid (CHEBI:76082 )
tetraric acid derivative (CHEBI:76082 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0303060)

Food

Fruit

Berry

Common grape (FooDB: FOOD00204)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.82 g/L	ALOGPS
logP	1.68	ALOGPS
logP	0.6	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	2.96	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	161.59 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	69.74 m³·mol⁻¹	ChemAxon
Polarizability	27.4 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0303060

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB007549

KNApSAcK ID

Not Available

Chemspider ID

30785782

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72551521

PDB ID

Not Available

ChEBI ID

76082

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for cis-Caftaric acid (CFc000282576)

MOL for CFc000282576 (cis-Caftaric acid)

3D MOL for CFc000282576 (cis-Caftaric acid)

3D SDF for CFc000282576 (cis-Caftaric acid)

3D-SDF for CFc000282576 (cis-Caftaric acid)

PDB for CFc000282576 (cis-Caftaric acid)

3D PDB for CFc000282576 (cis-Caftaric acid)

SMILES for CFc000282576 (cis-Caftaric acid)

INCHI for CFc000282576 (cis-Caftaric acid)

Structure for CFc000282576 (cis-Caftaric acid)

3D Structure for CFc000282576 (cis-Caftaric acid)