ChemFOnt: Showing chemical card for 3-Sinapoylquinic acid (CFc000281232)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:32:25 UTC

Chemfont ID

CFc000281232

Molecule Identification

Common Name

3-Sinapoylquinic acid

Definition

3-sinapoylquinic acid belongs to quinic acids and derivatives class of compounds. Those are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, and 5, as well as a carboxylic acid at position 1. 3-sinapoylquinic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 3-sinapoylquinic acid can be found in a number of food items such as sour cherry, sweet cherry, european plum, and peach (variety), which makes 3-sinapoylquinic acid a potential biomarker for the consumption of these food products. .

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-O-Sinapoylquinate	Generator
3-Sinapoylquinate	Generator

Chemical Formula

C₁₈H₂₂O₁₀

Average Molecular Weight

398.3613

Monoisotopic Molecular Weight

398.121296924

IUPAC Name

(1R,3R,4S,5R)-1,3,4-trihydroxy-5-{[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid

Traditional Name

(1R,3R,4S,5R)-1,3,4-trihydroxy-5-{[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid

CAS Registry Number

None

SMILES

COC1=CC(\C=C\C(=O)O[C@@H]2C[C@](O)(C[C@@H](O)[C@@H]2O)C(O)=O)=CC(OC)=C1O

InChI Identifier

InChI=1S/C18H22O10/c1-26-11-5-9(6-12(27-2)16(11)22)3-4-14(20)28-13-8-18(25,17(23)24)7-10(19)15(13)21/h3-6,10,13,15,19,21-22,25H,7-8H2,1-2H3,(H,23,24)/b4-3+/t10-,13-,15+,18-/m1/s1

InChI Key

DTJWTKVKHOJHJK-LTLLRWTCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, And 5, as well as a carboxylic acid at position 1.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Quinic acids and derivatives

Alternative Parents

Substituents

Quinic acid
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Methoxyphenol
M-dimethoxybenzene
Dimethoxybenzene
Anisole
Phenoxy compound
Methoxybenzene
Phenol ether
Styrene
Phenol
Alkyl aryl ether
Fatty acid ester
Cyclohexanol
Fatty acyl
Monocyclic benzene moiety
Hydroxy acid
Dicarboxylic acid or derivatives
Benzenoid
Alpha-hydroxy acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Ether
Polyol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

cinnamate ester (CHEBI:75493 )
cyclitol carboxylic acid (CHEBI:75493 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301716)

Food

Fruit

Pome

Apple (FooDB: FOOD00105)
Pear (FooDB: FOOD00152)

Drupe

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.5 g/L	ALOGPS
logP	0.29	ALOGPS
logP	-0.28	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	3.3	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	162.98 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	94.18 m³·mol⁻¹	ChemAxon
Polarizability	38.03 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

HMDB0301716

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000252

KNApSAcK ID

Not Available

Chemspider ID

30785641

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

75493

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 3-Sinapoylquinic acid (CFc000281232)

MOL for CFc000281232 (3-Sinapoylquinic acid)

3D MOL for CFc000281232 (3-Sinapoylquinic acid)

3D SDF for CFc000281232 (3-Sinapoylquinic acid)

3D-SDF for CFc000281232 (3-Sinapoylquinic acid)

PDB for CFc000281232 (3-Sinapoylquinic acid)

3D PDB for CFc000281232 (3-Sinapoylquinic acid)

SMILES for CFc000281232 (3-Sinapoylquinic acid)

INCHI for CFc000281232 (3-Sinapoylquinic acid)

Structure for CFc000281232 (3-Sinapoylquinic acid)

3D Structure for CFc000281232 (3-Sinapoylquinic acid)