ChemFOnt: Showing chemical card for 3-O-p-Coumaroylquinic acid (CFc000010914)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:58:30 UTC

Chemfont ID

CFc000010914

Molecule Identification

Common Name

3-O-p-Coumaroylquinic acid

Definition

3-O-p-Coumaroylquinic acid is found in apple. 3-O-p-Coumaroylquinic acid is found in cider apples, tea, cacao etc

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-O-p-Coumaroylquinate	Generator
1,4,5-Trihydroxy-3-[[3-(4-hydroxyphenyl)-1-oxo-2-propenyl]oxy]cyclohexanecarboxylic acid, 9ci	HMDB
O-Coumaroylquinic acid	HMDB
p-Coumaroyl quinic acid	HMDB
trans-5-O-(4-Coumaroyl)-D-quinate	HMDB
trans-5-O-(4-Coumaroyl)-D-quinic acid	HMDB
2-Coumaroylquinic acid	HMDB

Chemical Formula

C₁₆H₁₈O₈

Average Molecular Weight

338.3093

Monoisotopic Molecular Weight

338.100167552

IUPAC Name

(1R,3R,4S,5R)-1,3,4-trihydroxy-5-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid

Traditional Name

(1R,3R,4S,5R)-1,3,4-trihydroxy-5-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid

CAS Registry Number

None

SMILES

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

InChI Identifier

InChI=1S/C16H18O8/c17-10-4-1-9(2-5-10)3-6-13(19)24-12-8-16(23,15(21)22)7-11(18)14(12)20/h1-6,11-12,14,17-18,20,23H,7-8H2,(H,21,22)/b6-3+/t11-,12-,14+,16-/m1/s1

InChI Key

BMRSEYFENKXDIS-QHAYPTCMSA-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

Coumaric acid ester
Quinic acid
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Styrene
Phenol
Fatty acid ester
Cyclohexanol
1-hydroxy-2-unsubstituted benzenoid
Fatty acyl
Benzenoid
Alpha-hydroxy acid
Monocyclic benzene moiety
Hydroxy acid
Dicarboxylic acid or derivatives
Enoate ester
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Polyol
Carbonyl group
Organic oxide
Hydrocarbon derivative
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: HMDB0029681)
Cytoplasm (HMDB: HMDB0029681)

Source

Exogenous

Exogenous (HMDB: HMDB0029681)

Food

Fruit

Pome

Apple (FooDB: FOOD00105)
Pear (FooDB: FOOD00152)
Pomes (FooDB: FOOD00856)

Drupe

Berry

Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Gooseberry (FooDB: FOOD00157)
Strawberry (FooDB: FOOD00083)
Highbush blueberry (FooDB: FOOD00191)
Jostaberry (FooDB: FOOD00257)

Vegetable

Fruit vegetable

Avocado (FooDB: FOOD00130)

Root vegetable

Carrot (FooDB: FOOD00245)
Chicory (FooDB: FOOD00049)

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)

Tea

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Cocoa and cocoa products (FooDB: FOOD00860)

Endogenous

Endogenous (HMDB: HMDB0029681)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Stilbenoid, Diarylheptanoid, and Gingerol Biosynthesis (PathBank: SMP0063461)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.92 g/L	ALOGPS
logP	0.13	ALOGPS
logP	0.035	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	3.36	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.52 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	81.25 m³·mol⁻¹	ChemAxon
Polarizability	32.23 Å³	ChemAxon
Number of Rings	2	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

HMDB0029681

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000240

KNApSAcK ID

C00052747

Chemspider ID

8121397

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9945785

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 3-O-p-Coumaroylquinic acid (CFc000010914)

MOL for CFc000010914 (3-O-p-Coumaroylquinic acid)

3D MOL for CFc000010914 (3-O-p-Coumaroylquinic acid)

3D SDF for CFc000010914 (3-O-p-Coumaroylquinic acid)

3D-SDF for CFc000010914 (3-O-p-Coumaroylquinic acid)

PDB for CFc000010914 (3-O-p-Coumaroylquinic acid)

3D PDB for CFc000010914 (3-O-p-Coumaroylquinic acid)

SMILES for CFc000010914 (3-O-p-Coumaroylquinic acid)

INCHI for CFc000010914 (3-O-p-Coumaroylquinic acid)

Structure for CFc000010914 (3-O-p-Coumaroylquinic acid)

3D Structure for CFc000010914 (3-O-p-Coumaroylquinic acid)