ChemFOnt: Showing chemical card for 1,4-Di-O-caffeoylquinic acid (CFc000015809)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:05:07 UTC

Chemfont ID

CFc000015809

Molecule Identification

Common Name

1,4-Di-O-caffeoylquinic acid

Definition

1,4-Di-O-caffeoylquinic acid is found in herbs and spices. 1,4-Di-O-caffeoylquinic acid is isolated from flowers and leaves of Helichrysum italicum (curry plant

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,4-Di-O-caffeoylquinate	Generator
1,4-Bis-(3,4-dihydroxycinnamoyl)quinic acid	HMDB
1,4-Dicaffeoylquinic acid	HMDB
1,4-Dicaffeylquinic acid	HMDB
NSC 91529	HMDB
(1S,3R,4S,5R)-1,4-Bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-3,5-dihydroxycyclohexane-1-carboxylate	Generator

Chemical Formula

C₂₅H₂₄O₁₂

Average Molecular Weight

516.4509

Monoisotopic Molecular Weight

516.126776232

IUPAC Name

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

Traditional Name

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

CAS Registry Number

1182-34-9

SMILES

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

InChI Identifier

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

InChI Key

IYXQRCXQQWUFQV-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
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Tricarboxylic acid or derivatives
Catechol
Styrene
Phenol
1-hydroxy-4-unsubstituted benzenoid
Fatty acid ester
Cyclohexanol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Fatty acyl
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
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: HMDB0034766)
Cytoplasm (HMDB: HMDB0034766)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034766)

Source

Exogenous

Exogenous (HMDB: HMDB0034766)

Food

Food (HMDB: HMDB0034766)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0034766)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034766)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	2.06	ALOGPS
logP	2.16	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	3.21	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	50.16 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

HMDB0034766

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB013317

KNApSAcK ID

C00055091

Chemspider ID

22912997

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 1,4-Di-O-caffeoylquinic acid (CFc000015809)

MOL for CFc000015809 (1,4-Di-O-caffeoylquinic acid)

3D MOL for CFc000015809 (1,4-Di-O-caffeoylquinic acid)

3D SDF for CFc000015809 (1,4-Di-O-caffeoylquinic acid)

3D-SDF for CFc000015809 (1,4-Di-O-caffeoylquinic acid)

PDB for CFc000015809 (1,4-Di-O-caffeoylquinic acid)

3D PDB for CFc000015809 (1,4-Di-O-caffeoylquinic acid)

SMILES for CFc000015809 (1,4-Di-O-caffeoylquinic acid)

INCHI for CFc000015809 (1,4-Di-O-caffeoylquinic acid)

Structure for CFc000015809 (1,4-Di-O-caffeoylquinic acid)

3D Structure for CFc000015809 (1,4-Di-O-caffeoylquinic acid)