ChemFOnt: Showing chemical card for p-Coumaric acid sulfate (CFc000105575)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 21:22:34 UTC

Chemfont ID

CFc000105575

Molecule Identification

Common Name

p-Coumaric acid sulfate

Definition

p-Coumaric acid sulfate (CAS: 376374-66-2) is an endogenous phenolic acid metabolite. p-Coumaric acid sulfate was found to be elevated in rat urine after whole rye consumption which makes this compound a potential urinary biomarker of whole grain intake (PMID: 26862900 ). BioTransformer predicts that p-coumaric acid sulfate is a product of p-coumaric acid metabolism via a 4-O-sulfation-of-phenolic-compound reaction catalyzed by sulfotransferase 1A3 (P0DMM9) and sulfotransferase enzymes (PMID: 30612223 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-(Sulfooxy)benzeneacrylic acid	ChEBI
p-(Sulfooxy)-cinnamic acid	ChEBI
p-(Sulphooxy)-cinnamic acid	ChEBI
Zosteric acid	ChEBI
4-(Sulfooxy)benzeneacrylate	Generator
4-(Sulphooxy)benzeneacrylate	Generator
4-(Sulphooxy)benzeneacrylic acid	Generator
p-(Sulfooxy)-cinnamate	Generator
p-(Sulphooxy)-cinnamate	Generator
Zosterate	Generator
p-Coumarate sulfate	Generator
p-Coumarate sulphate	Generator
p-Coumaric acid sulfuric acid	Generator
p-Coumaric acid sulphuric acid	Generator
(2E)-3-[4-(Sulfooxy)phenyl]prop-2-enoate	HMDB
(2E)-3-[4-(Sulphooxy)phenyl]prop-2-enoate	HMDB
(2E)-3-[4-(Sulphooxy)phenyl]prop-2-enoic acid	HMDB
p-Sulfoxycinnamic acid	HMDB
p-Sulfoxycinnamate	HMDB
p-Sulphoxycinnamate	HMDB
p-Sulphoxycinnamic acid	HMDB
(e)-3-(4-Sulfooxyphenyl)prop-2-enoate	HMDB
(e)-3-(4-Sulphooxyphenyl)prop-2-enoate	HMDB
(e)-3-(4-Sulphooxyphenyl)prop-2-enoic acid	HMDB
(2E)-3-[4-(Sulfooxy)phenyl]-2-propenoic acid	HMDB
(2E)-3-[4-(Sulfooxy)phenyl]prop-2-enoic acid	HMDB
3-[4-(Sulfooxy)phenyl]-2-propenoic acid	HMDB
4-Hydroxycinnamic acid sulfate	HMDB
4-Hydroxycinnamic acid sulphate	HMDB
Coumaric acid sulfate	HMDB
Coumaric acid sulphate	HMDB
Coumaric acid-O-sulfate	HMDB
Coumaric acid-O-sulphate	HMDB
p-Coumaric acid sulphate	HMDB
p-trans-Coumaric acid sulfate	HMDB
p-trans-Coumaric acid sulphate	HMDB
p-Coumaric acid sulfate	HMDB

Chemical Formula

C₉H₈O₆S

Average Molecular Weight

244.22

Monoisotopic Molecular Weight

244.004159152

IUPAC Name

(2E)-3-[4-(sulfooxy)phenyl]prop-2-enoic acid

Traditional Name

(2E)-3-[4-(sulfooxy)phenyl]prop-2-enoic acid

CAS Registry Number

151481-49-1

SMILES

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

InChI Identifier

InChI=1S/C9H8O6S/c10-9(11)6-3-7-1-4-8(5-2-7)15-16(12,13)14/h1-6H,(H,10,11)(H,12,13,14)/b6-3+

InChI Key

OYDCCWNLILCHDJ-ZZXKWVIFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Cinnamic acids

Direct Parent

Cinnamic acids

Alternative Parents

Substituents

Cinnamic acid
Phenylsulfate
Arylsulfate
Phenoxy compound
Styrene
Benzenoid
Sulfuric acid ester
Sulfate-ester
Sulfuric acid monoester
Monocyclic benzene moiety
Organic sulfuric acid or derivatives
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Source

Endogenous

Endogenous (HMDB: HMDB0125166)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.43 g/L	ALOGPS
logP	-0.45	ALOGPS
logP	1.36	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	-2.2	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	55.03 m³·mol⁻¹	ChemAxon
Polarizability	21.73 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

External Links

HMDB ID

HMDB0125166

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB084080

KNApSAcK ID

C00056286

Chemspider ID

4797737

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6070438

PDB ID

Not Available

ChEBI ID

144380

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for p-Coumaric acid sulfate (CFc000105575)

MOL for CFc000105575 (p-Coumaric acid sulfate)

3D MOL for CFc000105575 (p-Coumaric acid sulfate)

3D SDF for CFc000105575 (p-Coumaric acid sulfate)

3D-SDF for CFc000105575 (p-Coumaric acid sulfate)

PDB for CFc000105575 (p-Coumaric acid sulfate)

3D PDB for CFc000105575 (p-Coumaric acid sulfate)

SMILES for CFc000105575 (p-Coumaric acid sulfate)

INCHI for CFc000105575 (p-Coumaric acid sulfate)

Structure for CFc000105575 (p-Coumaric acid sulfate)

3D Structure for CFc000105575 (p-Coumaric acid sulfate)