ChemFOnt: Showing chemical card for 3-O-Caffeoylshikimic acid (CFc000011862)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:59:45 UTC

Chemfont ID

CFc000011862

Molecule Identification

Common Name

3-O-Caffeoylshikimic acid

Definition

3-O-Caffeoylshikimic acid is found in date. 3-O-Caffeoylshikimic acid is a constituent of dates (Phoenix dactylifera)

Structure

MOL SDF PDB SMILES InChI

Synonyms

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

Chemical Formula

C₁₆H₁₆O₈

Average Molecular Weight

336.2934

Monoisotopic Molecular Weight

336.084517488

IUPAC Name

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

Traditional Name

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

CAS Registry Number

6082-44-6

SMILES

OC1C=C(CC(OC(=O)\C=C/C2=CC(O)=C(O)C=C2)C1O)C(O)=O

InChI Identifier

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

InChI Key

QMPHZIPNNJOWQI-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
Fatty acyl
Benzenoid
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
1,2-diol
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Carboxylic acid
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Alcohol
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: HMDB0030654)
Cytoplasm (HMDB: HMDB0030654)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030654)

Source

Endogenous

Endogenous (HMDB: HMDB0030654)

Plant

Plant (HMDB: HMDB0030654)

Exogenous

Food

Food (HMDB: HMDB0030654)

Fruit

Other fruit

Date (FooDB: FOOD00135)

Pome

Pear (FooDB: FOOD00152)

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0030654)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.01 g/L	ALOGPS
logP	1.17	ALOGPS
logP	0.79	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	3.94	ChemAxon
pKa (Strongest Basic)	-3.4	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	32.18 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

HMDB0030654

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB002563

KNApSAcK ID

C00054901

Chemspider ID

35013250

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dactylifric acid

METLIN ID

Not Available

PubChem Compound

131751067

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 3-O-Caffeoylshikimic acid (CFc000011862)

MOL for CFc000011862 (3-O-Caffeoylshikimic acid)

3D MOL for CFc000011862 (3-O-Caffeoylshikimic acid)

3D SDF for CFc000011862 (3-O-Caffeoylshikimic acid)

3D-SDF for CFc000011862 (3-O-Caffeoylshikimic acid)

PDB for CFc000011862 (3-O-Caffeoylshikimic acid)

3D PDB for CFc000011862 (3-O-Caffeoylshikimic acid)

SMILES for CFc000011862 (3-O-Caffeoylshikimic acid)

INCHI for CFc000011862 (3-O-Caffeoylshikimic acid)

Structure for CFc000011862 (3-O-Caffeoylshikimic acid)

3D Structure for CFc000011862 (3-O-Caffeoylshikimic acid)