ChemFOnt: Showing chemical card for cis-p-Coumaric acid (CFc000011883)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:59:47 UTC

Chemfont ID

CFc000011883

Molecule Identification

Common Name

cis-p-Coumaric acid

Definition

829

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2Z)-3-(4-Hydroxyphenyl)acrylic acid	ChEBI
(Z)-3-(4-Hydroxyphenyl)-2-propenoic acid	ChEBI
(Z)-p-Coumaric acid	ChEBI
(Z)-p-Hydroxycinnamic acid	ChEBI
cis-4-Hydroxycinnamic acid	ChEBI
cis-p-Coumarate	ChEBI
cis-p-Coumarinic acid	ChEBI
cis-p-Hydroxycinnamic acid	ChEBI
(2Z)-3-(4-Hydroxyphenyl)acrylate	Generator
(Z)-3-(4-Hydroxyphenyl)-2-propenoate	Generator
(Z)-p-Coumarate	Generator
(Z)-p-Hydroxycinnamate	Generator
cis-4-Hydroxycinnamate	Generator
cis-p-Coumarinate	Generator
cis-p-Hydroxycinnamate	Generator
cis-p-Coumaric acid	ChEBI
cis-4-Coumarate	Generator, HMDB
(2Z)-3-(4-Hydroxyphenyl)-2-propenoic acid	HMDB
(2Z)-3-(4-Hydroxyphenyl)prop-2-enoic acid	HMDB
(Z)-3-(4-Hydroxyphenyl)acrylic acid	HMDB
(Z)-4-Hydroxycinnamic acid	HMDB
3-(4-Hydroxyphenyl)-2-propenoic acid	HMDB
3-(4-Hydroxyphenyl)acrylic acid	HMDB
4-Coumaric acid	HMDB
4-Hydroxycinnamic acid	HMDB
beta-[4-Hydroxyphenyl]acrylic acid	HMDB
cis-3-(4-Hydroxyphenyl)-2-propenoic acid	HMDB
cis-4-Coumaric acid	HMDB
p-Coumaric acid	HMDB
p-Cumaric acid	HMDB
p-Hydroxy-cis-cinnamic acid	HMDB
p-Hydroxycinnamic acid	HMDB
p-Hydroxyphenylacrylic acid	HMDB
p-cis-Coumaric acid	HMDB
β-[4-Hydroxyphenyl]acrylic acid	HMDB

Chemical Formula

C₉H₈O₃

Average Molecular Weight

164.158

Monoisotopic Molecular Weight

164.047344122

IUPAC Name

(2Z)-3-(4-hydroxyphenyl)prop-2-enoic acid

Traditional Name

cis-p-coumaric acid

CAS Registry Number

4501-31-9

SMILES

OC(=O)\C=C/C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3-

InChI Key

NGSWKAQJJWESNS-UTCJRWHESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acids

Alternative Parents

Substituents

Cinnamic acid
Coumaric acid
Coumaric acid or derivatives
Hydroxycinnamic acid
Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

4-coumaric acid (CHEBI:17450 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 27273479)

Cellular substructure

Extracellular (HMDB: HMDB0030677)
Cytoplasm (HMDB: HMDB0030677)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030677)

Source

Endogenous

Endogenous (HMDB: HMDB0030677)

Plant

Plant (HMDB: HMDB0030677)

Exogenous

Food

Food (HMDB: HMDB0030677)

Beverage

Fermented beverage

Grape wine (FooDB: FOOD00612)

Herb and spice

Herb

Coriander (FooDB: FOOD00061)

Fruit

Pome

Pear (FooDB: FOOD00152)

Exogenous (HMDB: HMDB0030677)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.02 g/L	ALOGPS
logP	1.74	ALOGPS
logP	1.83	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	3.5	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	45.04 m³·mol⁻¹	ChemAxon
Polarizability	16.28 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon