ChemFOnt: Showing chemical card for Ferulic acid 4-O-sulfate (CFc000010448)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:57:53 UTC

Chemfont ID

CFc000010448

Molecule Identification

Common Name

Ferulic acid 4-O-sulfate

Definition

Ferulic acid 4-O-sulfate (CAS: 86321-29-1) is a phenolic acid metabolite. It is also a coffee metabolite found in blood or urine. Ferulic acid 4-O-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
Ferulate 4-O-glucuronide	Generator
(2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-acrylic acid glucuronide	HMDB
(2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid glucuronide	HMDB
(2E)-3-(4-Hydroxy-3-methoxyphenyl)prop-2-enoic acid glucuronide	HMDB
(e)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid glucuronide	HMDB
(e)-3-(4-Hydroxy-3-methoxyphenyl)acrylic acid glucuronide	HMDB
(e)-4-Hydroxy-3-methoxycinnamic acid glucuronide	HMDB
(e)-Ferulic acid glucuronide	HMDB
3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid glucuronide	HMDB
3-(4-Hydroxy-3-methoxyphenyl)acrylic acid glucuronide	HMDB
3-(4-Hydroxy-3-methoxyphenyl)propenoic acid glucuronide	HMDB
3-Methoxy-4-hydroxy-trans-cinnamic acid glucuronide	HMDB
3-Methoxy-4-hydroxycinnamic acid glucuronide	HMDB
4'-Hydroxy-3'-methoxycinnamic acid glucuronide	HMDB
4-Hydroxy-3-methoxycinnamic acid glucuronide	HMDB
4’-hydroxy-3’-methoxycinnamic acid glucuronide	HMDB
Coniferic acid glucuronide	HMDB
Ferulaic acid glucuronide	HMDB
Ferulic acid glucuronide	HMDB
Ferulic acid-4'-O-glucuronide	HMDB
Ferulic acid-4-O-glucuronide	HMDB
Ferulic acid-4’-O-glucuronide	HMDB
Fumalic acid glucuronide	HMDB
trans-4-Hydroxy-3-methoxycinnamic acid glucuronide	HMDB
trans-Ferulic acid glucuronide	HMDB
trans-Ferulic acid 4-O-glucuronide	HMDB
Ferulic acid 4-O-glucuronide	HMDB
Ferulate 4-glucuronide	Generator

Chemical Formula

C₁₆H₁₈O₁₀

Average Molecular Weight

370.3081

Monoisotopic Molecular Weight

370.089996796

IUPAC Name

(2S,3S,4S,5R,6S)-6-{4-[(1E)-2-carboxyeth-1-en-1-yl]-2-methoxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6S)-6-{4-[(1E)-2-carboxyeth-1-en-1-yl]-2-methoxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

151481-53-7

SMILES

COC1=C(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)C=CC(\C=C\C(O)=O)=C1

InChI Identifier

InChI=1S/C16H18O10/c1-24-9-6-7(3-5-10(17)18)2-4-8(9)25-16-13(21)11(19)12(20)14(26-16)15(22)23/h2-6,11-14,16,19-21H,1H3,(H,17,18)(H,22,23)/b5-3+/t11-,12-,13+,14-,16+/m0/s1

InChI Key

TWSIWBHKRJLZCF-MBAOVNHDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Cinnamic acid
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hexose monosaccharide
O-glycosyl compound
Phenoxy compound
Anisole
Methoxybenzene
Styrene
Phenol ether
Alkyl aryl ether
Beta-hydroxy acid
Monocyclic benzene moiety
Benzenoid
Dicarboxylic acid or derivatives
Pyran
Hydroxy acid
Monosaccharide
Oxane
Secondary alcohol
Organoheterocyclic compound
Carboxylic acid
Carboxylic acid derivative
Ether
Polyol
Acetal
Oxacycle
Alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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: 26269369)

Source

Endogenous

Endogenous (HMDB: HMDB0029200)

Plant

Plant (HMDB: HMDB0029200)

Exogenous

Food

Cocoa and cocoa product

Cocoa and cocoa products (HMDB: HMDB0029200)

Coffee and coffee product

Coffee product

Coffee products (HMDB: HMDB0029200)

Tea

Tea products (HMDB: HMDB0029200)

Fat and oil

Olive oil (HMDB: HMDB0029200)

Fruit

Fruits (HMDB: HMDB0029200)

Vegetable

Vegetables (HMDB: HMDB0029200)

Legumes (HMDB: HMDB0029200)

Cereal and cereal product

Cereal product

Whole grain cereal products (HMDB: HMDB0029200)

Nut

Nuts (HMDB: HMDB0029200)

Beverage

Alcoholic beverage

Red wine (HMDB: HMDB0029200)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0029200)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.81 g/L	ALOGPS
logP	-0.23	ALOGPS
logP	-0.27	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	3.01	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	162.98 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	83.52 m³·mol⁻¹	ChemAxon
Polarizability	34.54 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

HMDB0041733

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029899

KNApSAcK ID

Not Available

Chemspider ID

4947174

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6443140

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Ferulic acid 4-O-sulfate (CFc000010448)

MOL for CFc000010448 (Ferulic acid 4-O-sulfate)

3D MOL for CFc000010448 (Ferulic acid 4-O-sulfate)

3D SDF for CFc000010448 (Ferulic acid 4-O-sulfate)

3D-SDF for CFc000010448 (Ferulic acid 4-O-sulfate)

PDB for CFc000010448 (Ferulic acid 4-O-sulfate)

3D PDB for CFc000010448 (Ferulic acid 4-O-sulfate)

SMILES for CFc000010448 (Ferulic acid 4-O-sulfate)

INCHI for CFc000010448 (Ferulic acid 4-O-sulfate)

Structure for CFc000010448 (Ferulic acid 4-O-sulfate)

3D Structure for CFc000010448 (Ferulic acid 4-O-sulfate)