ChemFOnt: Showing chemical card for 1,3-Dicaffeoylquinic acid (CFc000010524)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:57:59 UTC

Chemfont ID

CFc000010524

Molecule Identification

Common Name

1,3-Dicaffeoylquinic acid

Definition

1,3-Dicaffeoylquinic acid is a polyphenol compound found in foods of plant origin (PMID: 20428313 )

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,3-Dicaffeoylquinate	Generator
15-O-trans-Dicaffeoylquinic acid	HMDB
15-O-trans-Dicaffeoylquinate	HMDB
1,3-Di-O-caffeoylquinic acid	HMDB
1,5-Dicaffeoylquinic acid?	HMDB
Cinarin	HMDB
Listrocol	HMDB
Cynarex	HMDB
Cinarine	HMDB
Nivellipid	HMDB
Phemocil	HMDB
1,5-Dicaffeoylquinic acid	HMDB
1-Carboxy-4,5-dihydroxy-1,3-cyclohexylenebis-(3,4-dihydroxycinnamate)	HMDB
Cynarin, (1alpha,3alpha,4alpha,5beta)-isomer	HMDB
Listricol	HMDB
Cinarina	HMDB
Cynarin	HMDB
Cynarine	HMDB
Cynarix	HMDB
(1S,3R,4R,5R)-1,3-Bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4,5-dihydroxycyclohexane-1-carboxylate	HMDB
1,3-Dicaffeoylquinic acid	MeSH

Chemical Formula

C₂₅H₂₄O₁₂

Average Molecular Weight

516.4509

Monoisotopic Molecular Weight

516.126776232

IUPAC Name

(1S,3R,4R,5R)-1,3-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4,5-dihydroxycyclohexane-1-carboxylic acid

Traditional Name

(1S,3R,4R,5R)-1,3-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4,5-dihydroxycyclohexane-1-carboxylic acid

CAS Registry Number

19870-46-3

SMILES

O[C@@H]1C[C@@](C[C@@H](OC(=O)\C=C\C2=CC=C(O)C(O)=C2)[C@@H]1O)(OC(=O)\C=C\C1=CC=C(O)C(O)=C1)C(O)=O

InChI Identifier

InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(24(34)35,11-19(30)23(20)33)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,33H,11-12H2,(H,34,35)/b7-3+,8-4+/t19-,20-,23-,25+/m1/s1

InChI Key

YDDUMTOHNYZQPO-PSEXTPKNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, And 5, as well as a carboxylic acid at position 1.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Quinic acids and derivatives

Alternative Parents

Substituents

Quinic acid
Cinnamic acid or derivatives
Coumaric acid or derivatives
Cinnamic acid ester
Hydroxycinnamic acid or derivatives
Tricarboxylic acid or derivatives
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Cyclohexanol
Phenol
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
1,2-diol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Carbonyl group
Organic oxide
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: HMDB0029279)
Cytoplasm (HMDB: HMDB0029279)

Source

Endogenous

Endogenous (HMDB: HMDB0029279)

Exogenous

Food

Food (HMDB: HMDB0029279)

Exogenous (HMDB: HMDB0029279)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	2.07	ALOGPS
logP	2.16	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	3.18	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	211.28 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	126.76 m³·mol⁻¹	ChemAxon
Polarizability	49.62 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0029279

DrugBank ID

Not Available

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6474640

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 1,3-Dicaffeoylquinic acid (CFc000010524)

MOL for CFc000010524 (1,3-Dicaffeoylquinic acid)

3D MOL for CFc000010524 (1,3-Dicaffeoylquinic acid)

3D SDF for CFc000010524 (1,3-Dicaffeoylquinic acid)

3D-SDF for CFc000010524 (1,3-Dicaffeoylquinic acid)

PDB for CFc000010524 (1,3-Dicaffeoylquinic acid)

3D PDB for CFc000010524 (1,3-Dicaffeoylquinic acid)

SMILES for CFc000010524 (1,3-Dicaffeoylquinic acid)

INCHI for CFc000010524 (1,3-Dicaffeoylquinic acid)

Structure for CFc000010524 (1,3-Dicaffeoylquinic acid)

3D Structure for CFc000010524 (1,3-Dicaffeoylquinic acid)