ChemFOnt: Showing chemical card for Pelargonidin 3-arabinoside (CFc000281179)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:32:18 UTC

Chemfont ID

CFc000281179

Molecule Identification

Common Name

Pelargonidin 3-arabinoside

Definition

Pelargonidin 3-arabinoside is a member of the class of compounds known as anthocyanidin-3-o-glycosides. Anthocyanidin-3-o-glycosides are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C3-position. Pelargonidin 3-arabinoside is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Pelargonidin 3-arabinoside can be found in a number of food items such as gooseberry, strawberry, black elderberry, and blackcurrant, which makes pelargonidin 3-arabinoside a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₀H₁₉O₉

Average Molecular Weight

403.3595

Monoisotopic Molecular Weight

403.102907206

IUPAC Name

3-{[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxyphenyl)-1lambda4-chromen-1-ylium

Traditional Name

3-{[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxyphenyl)-1lambda4-chromen-1-ylium

CAS Registry Number

None

SMILES

[H][C@]1(CO)O[C@]([H])(OC2=CC3=C(O)C=C(O)C=C3[O+]=C2C2=CC=C(O)C=C2)[C@@]([H])(O)[C@]1([H])O

InChI Identifier

InChI=1S/C20H18O9/c21-8-16-17(25)18(26)20(29-16)28-15-7-12-13(24)5-11(23)6-14(12)27-19(15)9-1-3-10(22)4-2-9/h1-7,16-18,20-21,25-26H,8H2,(H2-,22,23,24)/p+1/t16-,17-,18+,20+/m1/s1

InChI Key

BGOQMKHOLJPANL-XSYGEPLQSA-O

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
Anthocyanin
Anthocyanidin-3-o-glycoside
Flavonoid-3-o-glycoside
3p-methoxyflavonoid-skeleton
Hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Anthocyanidin
Hydroxycinnamic acid or derivatives
Coumaric acid or derivatives
Cinnamic acid or derivatives
Cinnamic acid ester
Glycosyl compound
O-glycosyl compound
Dimethoxybenzene
M-dimethoxybenzene
Methoxyphenol
1-benzopyran
Benzopyran
Styrene
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
Catechol
Phenol
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Oxane
Monosaccharide
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Acetal
Polyol
Ether
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Alcohol
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301663)

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.28 g/L	ALOGPS
logP	1.62	ALOGPS
logP	1.34	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	6.4	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	152.98 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	108.31 m³·mol⁻¹	ChemAxon
Polarizability	39.24 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0301663

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000031

KNApSAcK ID

Not Available

Chemspider ID

30780055

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-arabinoside (CFc000281179)

MOL for CFc000281179 (Pelargonidin 3-arabinoside)

3D MOL for CFc000281179 (Pelargonidin 3-arabinoside)

3D SDF for CFc000281179 (Pelargonidin 3-arabinoside)

3D-SDF for CFc000281179 (Pelargonidin 3-arabinoside)

PDB for CFc000281179 (Pelargonidin 3-arabinoside)

3D PDB for CFc000281179 (Pelargonidin 3-arabinoside)

SMILES for CFc000281179 (Pelargonidin 3-arabinoside)

INCHI for CFc000281179 (Pelargonidin 3-arabinoside)

Structure for CFc000281179 (Pelargonidin 3-arabinoside)

3D Structure for CFc000281179 (Pelargonidin 3-arabinoside)