ChemFOnt: Showing chemical card for Malvidin 3-arabinoside (CFc000283154)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:36:09 UTC

Chemfont ID

CFc000283154

Molecule Identification

Common Name

Malvidin 3-arabinoside

Definition

Malvidin 3-arabinoside is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Malvidin 3-arabinoside can be found in a number of food items such as sweet cherry, lingonberry, red raspberry, and american cranberry, which makes malvidin 3-arabinoside a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₂H₂₃O₁₁

Average Molecular Weight

463.4114

Monoisotopic Molecular Weight

463.124036578

IUPAC Name

3-{[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-1λ⁴-chromen-1-ylium

Traditional Name

3-{[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-1λ⁴-chromen-1-ylium

CAS Registry Number

28500-04-1

SMILES

COC1=CC(=CC(OC)=C1O)C1=[O+]C2=C(C=C1O[C@H]1O[C@H](CO)[C@@H](O)[C@@H]1O)C(O)=CC(O)=C2

InChI Identifier

InChI=1S/C22H22O11/c1-29-14-3-9(4-15(30-2)18(14)26)21-16(32-22-20(28)19(27)17(8-23)33-22)7-11-12(25)5-10(24)6-13(11)31-21/h3-7,17,19-20,22-23,27-28H,8H2,1-2H3,(H2-,24,25,26)/p+1/t17-,19-,20+,22+/m1/s1

InChI Key

WNKBGLOGIZOFFU-PBVWOCPUSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthocyanidin-3-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Anthocyanidin-3-O-glycosides

Alternative Parents

Substituents

Anthocyanidin-3-o-glycoside
Flavonoid-3-o-glycoside
3p-methoxyflavonoid-skeleton
Hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Anthocyanidin
Glycosyl compound
O-glycosyl compound
Benzopyran
Methoxyphenol
Pentose monosaccharide
1-benzopyran
M-dimethoxybenzene
Dimethoxybenzene
Anisole
Phenol ether
Phenoxy compound
Methoxybenzene
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monosaccharide
Benzenoid
Monocyclic benzene moiety
Heteroaromatic compound
Tetrahydrofuran
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Acetal
Ether
Alcohol
Organic oxygen compound
Primary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0303638)

Food

Fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Blackcurrant (FooDB: FOOD00155)
Lingonberry (FooDB: FOOD00194)
Strawberry (FooDB: FOOD00083)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Red raspberry (FooDB: FOOD00162)
Black crowberry (FooDB: FOOD00075)
Black chokeberry (FooDB: FOOD00136)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Canada blueberry (FooDB: FOOD00211)
Summer grape (FooDB: FOOD00227)
Rabbiteye blueberry (FooDB: FOOD00898)

Drupe

Sweet cherry (FooDB: FOOD00145)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.23 g/L	ALOGPS
logP	1.71	ALOGPS
logP	0.84	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	6.38	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	171.44 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	121.24 m³·mol⁻¹	ChemAxon
Polarizability	45.19 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0303638

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB017210

KNApSAcK ID

Not Available

Chemspider ID

30780112

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

157010086

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Malvidin 3-arabinoside (CFc000283154)

MOL for CFc000283154 (Malvidin 3-arabinoside)

3D MOL for CFc000283154 (Malvidin 3-arabinoside)

3D SDF for CFc000283154 (Malvidin 3-arabinoside)

3D-SDF for CFc000283154 (Malvidin 3-arabinoside)

PDB for CFc000283154 (Malvidin 3-arabinoside)

3D PDB for CFc000283154 (Malvidin 3-arabinoside)

SMILES for CFc000283154 (Malvidin 3-arabinoside)

INCHI for CFc000283154 (Malvidin 3-arabinoside)

Structure for CFc000283154 (Malvidin 3-arabinoside)

3D Structure for CFc000283154 (Malvidin 3-arabinoside)