ChemFOnt: Showing chemical card for 4-O-Caffeoylshikimic acid (CFc000015076)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:04:06 UTC

Chemfont ID

CFc000015076

Molecule Identification

Common Name

4-O-Caffeoylshikimic acid

Definition

4-O-Caffeoylshikimic acid is found in fruits. 4-O-Caffeoylshikimic acid is isolated from unripe dates (Phoenix dactylifera).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-O-Caffeoylshikimate	Generator
4-Caffeoylshikimic acid	HMDB
Isodactylifric acid	HMDB
Isodattelic acid	HMDB
4-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,5-dihydroxycyclohex-1-ene-1-carboxylate	Generator

Chemical Formula

C₁₆H₁₆O₈

Average Molecular Weight

336.2934

Monoisotopic Molecular Weight

336.084517488

IUPAC Name

4-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,5-dihydroxycyclohex-1-ene-1-carboxylic acid

Traditional Name

4-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,5-dihydroxycyclohex-1-ene-1-carboxylic acid

CAS Registry Number

None

SMILES

OC1CC(=CC(O)C1OC(=O)\C=C/C1=CC(O)=C(O)C=C1)C(O)=O

InChI Identifier

InChI=1S/C16H16O8/c17-10-3-1-8(5-11(10)18)2-4-14(21)24-15-12(19)6-9(16(22)23)7-13(15)20/h1-6,12-13,15,17-20H,7H2,(H,22,23)/b4-2-

InChI Key

VTURJKQJEXSKNY-RQOWECAXSA-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

Coumaric acid or derivatives
Cinnamic acid ester
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Cyclitol or derivatives
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
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: HMDB0033997)
Cytoplasm (HMDB: HMDB0033997)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033997)

Source

Exogenous

Exogenous (HMDB: HMDB0033997)

Food

Food (HMDB: HMDB0033997)

Fruit

Pome

Pear (FooDB: FOOD00152)

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0033997)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033997)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1 g/L	ALOGPS
logP	1.21	ALOGPS
logP	0.79	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	4	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	82.49 m³·mol⁻¹	ChemAxon
Polarizability	31.94 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

HMDB0033997

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012231

KNApSAcK ID

Not Available

Chemspider ID

35013684

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751510

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 4-O-Caffeoylshikimic acid (CFc000015076)

MOL for CFc000015076 (4-O-Caffeoylshikimic acid)

3D MOL for CFc000015076 (4-O-Caffeoylshikimic acid)

3D SDF for CFc000015076 (4-O-Caffeoylshikimic acid)

3D-SDF for CFc000015076 (4-O-Caffeoylshikimic acid)

PDB for CFc000015076 (4-O-Caffeoylshikimic acid)

3D PDB for CFc000015076 (4-O-Caffeoylshikimic acid)

SMILES for CFc000015076 (4-O-Caffeoylshikimic acid)

INCHI for CFc000015076 (4-O-Caffeoylshikimic acid)

Structure for CFc000015076 (4-O-Caffeoylshikimic acid)

3D Structure for CFc000015076 (4-O-Caffeoylshikimic acid)