ChemFOnt: Showing chemical card for pelargonidin 3-O-beta-D-caffeoylglucoside (CFc000283966)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:37:43 UTC

Chemfont ID

CFc000283966

Molecule Identification

Common Name

pelargonidin 3-O-beta-D-caffeoylglucoside

Definition

Pelargonidin 3-o-beta-d-caffeoylglucoside is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Pelargonidin 3-o-beta-d-caffeoylglucoside can be found in a number of food items such as cauliflower, swamp cabbage, enokitake, and sunflower, which makes pelargonidin 3-o-beta-d-caffeoylglucoside a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-{[(6-{[5,7-dihydroxy-2-(4-oxocyclohexa-2,5-dien-1-ylidene)-2H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl]oxidaniumylidene}-3-(3,4-dihydroxyphenyl)prop-2-en-1-olic acid	Generator

Chemical Formula

C₃₀H₂₆O₁₃

Average Molecular Weight

594.525

Monoisotopic Molecular Weight

594.137340897

IUPAC Name

3-{[6-({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-7-hydroxy-2-(4-hydroxyphenyl)-1λ⁴-chromen-1-ylium-5-olate

Traditional Name

3-{[6-({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-7-hydroxy-2-(4-hydroxyphenyl)-1λ⁴-chromen-1-ylium-5-olate

CAS Registry Number

Not Available

SMILES

OC1C(COC(=O)C=CC2=CC(O)=C(O)C=C2)OC(OC2=CC3=C(C=C(O)C=C3[O-])[O+]=C2C2=CC=C(O)C=C2)C(O)C1O

InChI Identifier

InChI=1S/C30H26O13/c31-16-5-3-15(4-6-16)29-23(12-18-20(34)10-17(32)11-22(18)41-29)42-30-28(39)27(38)26(37)24(43-30)13-40-25(36)8-2-14-1-7-19(33)21(35)9-14/h1-12,24,26-28,30,37-39H,13H2,(H4-,31,32,33,34,35,36)

InChI Key

OUWGZZOPFVOIFO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid 3-o-p-coumaroyl glycosides. These are flavonoid 3-O-glycosides where the carbohydrate moiety is esterified with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid 3-O-p-coumaroyl glycosides

Alternative Parents

Substituents

Flavonoid 3-o-6-p-coumaroyl-glycoside
Flavonoid-3-o-glycoside
4'-hydroxyflavonoid
5-hydroxyflavonoid
Hydroxyflavonoid
Coumaric acid ester
Hydroxycinnamic acid or derivatives
Coumaric acid or derivatives
Cinnamic acid or derivatives
Cinnamic acid ester
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Styrene
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
1-hydroxy-4-unsubstituted benzenoid
Fatty acyl
Monosaccharide
Monocyclic benzene moiety
Oxane
Benzenoid
Vinylogous acid
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Cyclic ketone
Secondary alcohol
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Carbonyl group
Organic oxide
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.05 g/L	ALOGPS
logP	3.27	ALOGPS
logP	3.8	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	6.4	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	222.57 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	168.36 m³·mol⁻¹	ChemAxon
Polarizability	57.63 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0304450

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB031088

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 pelargonidin 3-O-beta-D-caffeoylglucoside (CFc000283966)

MOL for CFc000283966 (pelargonidin 3-O-beta-D-caffeoylglucoside)

3D MOL for CFc000283966 (pelargonidin 3-O-beta-D-caffeoylglucoside)

3D SDF for CFc000283966 (pelargonidin 3-O-beta-D-caffeoylglucoside)

3D-SDF for CFc000283966 (pelargonidin 3-O-beta-D-caffeoylglucoside)

PDB for CFc000283966 (pelargonidin 3-O-beta-D-caffeoylglucoside)

3D PDB for CFc000283966 (pelargonidin 3-O-beta-D-caffeoylglucoside)

SMILES for CFc000283966 (pelargonidin 3-O-beta-D-caffeoylglucoside)

INCHI for CFc000283966 (pelargonidin 3-O-beta-D-caffeoylglucoside)

Structure for CFc000283966 (pelargonidin 3-O-beta-D-caffeoylglucoside)

3D Structure for CFc000283966 (pelargonidin 3-O-beta-D-caffeoylglucoside)