ChemFOnt: Showing chemical card for Sinapic acid 4-O-glucuronide (CFc000220646)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 01:39:53 UTC

Chemfont ID

CFc000220646

Molecule Identification

Common Name

Sinapic acid 4-O-glucuronide

Definition

Sinapic acid 4-O-glucuronide is an endogenous phenolic acid metabolite. Sinapic acid 4-O-glucuronide 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
Sinapate 4-O-glucuronide	Generator
(2S,3S,4S,5R,6S)-6-{4-[(1E)-2-carboxyeth-1-en-1-yl]-2,6-dimethoxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylate	HMDB
(2E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acid glucuronide	HMDB
(e)-3,5-Dimethoxy-4-hydroxycinnamic acid glucuronide	HMDB
(e)-3-(4-Hydroxy-3,5-dimethoxyphenyl)acrylic acid glucuronide	HMDB
(e)-Sinapic acid glucuronide	HMDB
3,5-Dimethoxy-4-hydroxy-trans-cinnamic acid glucuronide	HMDB
3,5-Dimethoxy-4-hydroxycinnamic acid glucuronide	HMDB
3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acid glucuronide	HMDB
4-Hydroxy-3,5-dimethoxycinnamic acid glucuronide	HMDB
e-Sinapinic acid glucuronide	HMDB
Sinapic acid glucuronide	HMDB
Sinapic acid-4'-O-glucuronide	HMDB
Sinapic acid-4-O-glucuronide	HMDB
Sinapic acid-4’-O-glucuronide	HMDB
Sinapinic acid glucuronide	HMDB
Synapitic acid glucuronide	HMDB
trans-4-Hydroxy-3,5-dimethoxycinnamic acid glucuronide	HMDB
trans-Sinapic acid glucuronide	HMDB
trans-Sinapinic acid glucuronide	HMDB

Chemical Formula

C₁₇H₂₀O₁₁

Average Molecular Weight

400.336

Monoisotopic Molecular Weight

400.100561464

IUPAC Name

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

Traditional Name

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

CAS Registry Number

233604-90-5

SMILES

COC1=CC(\C=C\C(O)=O)=CC(OC)=C1O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C17H20O11/c1-25-8-5-7(3-4-10(18)19)6-9(26-2)14(8)27-17-13(22)11(20)12(21)15(28-17)16(23)24/h3-6,11-13,15,17,20-22H,1-2H3,(H,18,19)(H,23,24)/b4-3+/t11-,12-,13+,15-,17+/m0/s1

InChI Key

SVMPWPWAQOHKHG-OGUZRXNMSA-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
O-glucuronide
1-o-glucuronide
Glucuronic acid or derivatives
Hexose monosaccharide
Coumaric acid or derivatives
Cinnamic acid or derivatives
Cinnamic acid
O-glycosyl compound
Dimethoxybenzene
M-dimethoxybenzene
Phenol ether
Styrene
Anisole
Phenoxy compound
Methoxybenzene
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: 32966057)

Source

Exogenous

Exogenous (HMDB: HMDB0240383)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.12 g/L	ALOGPS
logP	-0.08	ALOGPS
logP	-0.43	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	2.92	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	172.21 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	89.98 m³·mol⁻¹	ChemAxon
Polarizability	37.66 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0240383

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Sinapic acid 4-O-glucuronide (CFc000220646)

MOL for CFc000220646 (Sinapic acid 4-O-glucuronide)

3D MOL for CFc000220646 (Sinapic acid 4-O-glucuronide)

3D SDF for CFc000220646 (Sinapic acid 4-O-glucuronide)

3D-SDF for CFc000220646 (Sinapic acid 4-O-glucuronide)

PDB for CFc000220646 (Sinapic acid 4-O-glucuronide)

3D PDB for CFc000220646 (Sinapic acid 4-O-glucuronide)

SMILES for CFc000220646 (Sinapic acid 4-O-glucuronide)

INCHI for CFc000220646 (Sinapic acid 4-O-glucuronide)

Structure for CFc000220646 (Sinapic acid 4-O-glucuronide)

3D Structure for CFc000220646 (Sinapic acid 4-O-glucuronide)