ChemFOnt: Showing chemical card for Apigeninidin 5-(5''-caffeylarabinoside) (CFc000281398)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:32:44 UTC

Chemfont ID

CFc000281398

Molecule Identification

Common Name

Apigeninidin 5-(5''-caffeylarabinoside)

Definition

Apigeninidin 5-(5''-caffeylarabinoside) is a member of the class of compounds known as anthocyanidin-5-o-glycosides. Anthocyanidin-5-o-glycosides are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C5-position. Apigeninidin 5-(5''-caffeylarabinoside) is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Apigeninidin 5-(5''-caffeylarabinoside) can be found in sorghum, which makes apigeninidin 5-(5''-caffeylarabinoside) a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₉H₂₅O₁₁

Average Molecular Weight

549.5022

Monoisotopic Molecular Weight

549.139686642

IUPAC Name

5-{[(2S,3R,4R,5S)-5-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]oxy}-7-hydroxy-2-(4-hydroxyphenyl)-1λ⁴-chromen-1-ylium

Traditional Name

5-{[(2S,3R,4R,5S)-5-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]oxy}-7-hydroxy-2-(4-hydroxyphenyl)-1λ⁴-chromen-1-ylium

CAS Registry Number

131400-98-1

SMILES

O[C@H]1[C@H](COC(=O)\C=C\C2=CC(O)=C(O)C=C2)O[C@@H](OC2=CC(O)=CC3=C2C=CC(=[O+]3)C2=CC=C(O)C=C2)[C@@H]1O

InChI Identifier

InChI=1S/C29H24O11/c30-17-5-3-16(4-6-17)22-9-7-19-23(38-22)12-18(31)13-24(19)39-29-28(36)27(35)25(40-29)14-37-26(34)10-2-15-1-8-20(32)21(33)11-15/h1-13,25,27-29,35-36H,14H2,(H3-,30,31,32,33,34)/p+1/t25-,27-,28+,29+/m0/s1

InChI Key

BBZCRSFPHPHYKT-ANHREMPLSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthocyanidin-5-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C5-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Anthocyanidin-5-O-glycosides

Alternative Parents

Substituents

Anthocyanidin-5-o-glycoside
Hydroxyflavonoid
4'-hydroxyflavonoid
7-hydroxyflavonoid
Anthocyanidin
Phenolic glycoside
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Coumaric acid or derivatives
Cinnamic acid or derivatives
O-glycosyl compound
Glycosyl compound
1-benzopyran
Pentose monosaccharide
Benzopyran
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
Fatty acid ester
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monosaccharide
Fatty acyl
Monocyclic benzene moiety
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
1,2-diol
Secondary alcohol
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Acetal
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301882)

Food

Cereal and cereal product

Cereal

Sorghum (FooDB: FOOD00177)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0079 g/L	ALOGPS
logP	3.85	ALOGPS
logP	4.76	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	6.84	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	179.28 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	149.86 m³·mol⁻¹	ChemAxon
Polarizability	55.98 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

HMDB0301882

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001569

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 Apigeninidin 5-(5''-caffeylarabinoside) (CFc000281398)

MOL for CFc000281398 (Apigeninidin 5-(5''-caffeylarabinoside))

3D MOL for CFc000281398 (Apigeninidin 5-(5''-caffeylarabinoside))

3D SDF for CFc000281398 (Apigeninidin 5-(5''-caffeylarabinoside))

3D-SDF for CFc000281398 (Apigeninidin 5-(5''-caffeylarabinoside))

PDB for CFc000281398 (Apigeninidin 5-(5''-caffeylarabinoside))

3D PDB for CFc000281398 (Apigeninidin 5-(5''-caffeylarabinoside))

SMILES for CFc000281398 (Apigeninidin 5-(5''-caffeylarabinoside))

INCHI for CFc000281398 (Apigeninidin 5-(5''-caffeylarabinoside))

Structure for CFc000281398 (Apigeninidin 5-(5''-caffeylarabinoside))

3D Structure for CFc000281398 (Apigeninidin 5-(5''-caffeylarabinoside))