ChemFOnt: Showing chemical card for Caffeic acid 3-O-sulfate (CFc000022567)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:14:56 UTC

Chemfont ID

CFc000022567

Molecule Identification

Common Name

Caffeic acid 3-O-sulfate

Definition

Caffeic acid 3-O-sulfate (CAS: 1208232-16-9) is a polyphenol metabolite detected in biological fluids (PMID: 20428313 ). Caffeic 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 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Caffeic acid 3'-O-sulfate	ChEBI
Caffeic acid 3'-sulfate	ChEBI
Caffeic acid 3-sulphate	ChEBI
Caffeate 3'-O-sulfate	Generator
Caffeate 3'-O-sulphate	Generator
Caffeic acid 3'-O-sulfuric acid	Generator
Caffeic acid 3'-O-sulphuric acid	Generator
Caffeate 3'-sulfate	Generator
Caffeate 3'-sulphate	Generator
Caffeic acid 3'-sulfuric acid	Generator
Caffeic acid 3'-sulphuric acid	Generator
Caffeate 3-sulfate	Generator
Caffeate 3-sulphate	Generator
Caffeic acid 3-sulfuric acid	Generator
Caffeic acid 3-sulphuric acid	Generator
Caffeate 3-O-sulfate	Generator
Caffeate 3-O-sulphate	Generator
Caffeic acid 3-O-sulfuric acid	Generator
Caffeic acid 3-O-sulphuric acid	Generator
(2E)-3-[4-Hydroxy-3-(sulfooxy)phenyl]-2-propenoic acid	HMDB
(e)-Caffeic acid 3-O-sulfate	HMDB
(e)-Caffeic acid 3-O-sulphate	HMDB
(e)-Caffeic acid 3-sulfate	HMDB
(e)-Caffeic acid 3-sulphate	HMDB
(e)-Caffeic acid sulfate	HMDB
(e)-Caffeic acid sulphate	HMDB
3-[4-Hydroxy-3-(sulfooxy)phenyl]-2-propenoic acid	HMDB
Caffeic acid 3-O-sulphate	HMDB
Caffeic acid 3-sulfate	HMDB
Caffeic acid sulfate	HMDB
Caffeic acid sulphate	HMDB
trans-Caffeic acid 3-O-sulfate	HMDB
trans-Caffeic acid 3-O-sulphate	HMDB
trans-Caffeic acid 3-sulfate	HMDB
trans-Caffeic acid 3-sulphate	HMDB
trans-Caffeic acid sulfate	HMDB
trans-Caffeic acid sulphate	HMDB
Caffeic acid 3-O-sulfate	ChEBI

Chemical Formula

C₉H₈O₇S

Average Molecular Weight

260.221

Monoisotopic Molecular Weight

259.9990733

IUPAC Name

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

Traditional Name

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

CAS Registry Number

151481-52-6

SMILES

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

InChI Identifier

InChI=1S/C9H8O7S/c10-7-3-1-6(2-4-9(11)12)5-8(7)16-17(13,14)15/h1-5,10H,(H,11,12)(H,13,14,15)/b4-2+

InChI Key

VWQNTRNACRFUCQ-DUXPYHPUSA-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 or derivatives
Hydroxycinnamic acid
Phenylsulfate
Arylsulfate
Phenoxy compound
Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Sulfuric acid ester
Sulfate-ester
Sulfuric acid monoester
Organic sulfuric acid or derivatives
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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: 19460943)

Excreta

Biofluid or Excreta

Urine (PMID: 19460943)

Cellular substructure

Extracellular (HMDB: HMDB0041706)
Cytoplasm (HMDB: HMDB0041706)

Source

Endogenous

Endogenous (HMDB: HMDB0041706)

Plant

Plant (HMDB: HMDB0041706)

Exogenous

Food

Food (HMDB: HMDB0041706)
Legumes (HMDB: HMDB0041706)

Cocoa and cocoa product

Cocoa and cocoa products (HMDB: HMDB0041706)

Coffee and coffee product

Coffee product

Coffee products (HMDB: HMDB0041706)

Tea

Tea products (HMDB: HMDB0041706)

Fat and oil

Olive oil (HMDB: HMDB0041706)

Fruit

Fruits (HMDB: HMDB0041706)

Vegetable

Vegetables (HMDB: HMDB0041706)

Cereal and cereal product

Cereal product

Whole grain cereal products (HMDB: HMDB0041706)

Nut

Nuts (HMDB: HMDB0041706)

Beverage

Alcoholic beverage

Red wine (HMDB: HMDB0041706)

Exogenous (HMDB: HMDB0041706)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0041706)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.75 g/L	ALOGPS
logP	-0.37	ALOGPS
logP	1.7	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	-2.3	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	121.13 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	57.01 m³·mol⁻¹	ChemAxon
Polarizability	22.35 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

HMDB0041706

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029871

KNApSAcK ID

Not Available

Chemspider ID

30777605

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102261219

PDB ID

Not Available

ChEBI ID

90242

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Caffeic acid 3-O-sulfate (CFc000022567)

MOL for CFc000022567 (Caffeic acid 3-O-sulfate)

3D MOL for CFc000022567 (Caffeic acid 3-O-sulfate)

3D SDF for CFc000022567 (Caffeic acid 3-O-sulfate)

3D-SDF for CFc000022567 (Caffeic acid 3-O-sulfate)

PDB for CFc000022567 (Caffeic acid 3-O-sulfate)

3D PDB for CFc000022567 (Caffeic acid 3-O-sulfate)

SMILES for CFc000022567 (Caffeic acid 3-O-sulfate)

INCHI for CFc000022567 (Caffeic acid 3-O-sulfate)

Structure for CFc000022567 (Caffeic acid 3-O-sulfate)

3D Structure for CFc000022567 (Caffeic acid 3-O-sulfate)