ChemFOnt: Showing chemical card for Pelargonidin 3-rutinoside (CFc000283303)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:36:27 UTC

Chemfont ID

CFc000283303

Molecule Identification

Common Name

Pelargonidin 3-rutinoside

Definition

Pelargonidin 3-rutinoside 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-rutinoside is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Pelargonidin 3-rutinoside can be found in a number of food items such as gooseberry, lowbush blueberry, black chokeberry, and redcurrant, which makes pelargonidin 3-rutinoside a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₇H₃₁O₁₄

Average Molecular Weight

579.5266

Monoisotopic Molecular Weight

579.1713807

IUPAC Name

5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1lambda4-chromen-1-ylium

Traditional Name

5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1lambda4-chromen-1-ylium

CAS Registry Number

33978-17-5

SMILES

C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=CC4=C(O)C=C(O)C=C4[O+]=C3C3=CC=C(O)C=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C27H30O14/c1-10-19(31)21(33)23(35)26(38-10)37-9-18-20(32)22(34)24(36)27(41-18)40-17-8-14-15(30)6-13(29)7-16(14)39-25(17)11-2-4-12(28)5-3-11/h2-8,10,18-24,26-27,31-36H,9H2,1H3,(H2-,28,29,30)/p+1/t10-,18+,19-,20+,21+,22-,23+,24+,26+,27+/m0/s1

InChI Key

IFYOHQQBIKDHFT-ASZXTAQUSA-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
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Anthocyanidin
Disaccharide
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Oxane
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Polyol
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organooxygen compound
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

anthocyanin cation (CHEBI:31968 )
rutinoside (CHEBI:31968 )
disaccharide derivative (CHEBI:31968 )
Anthocyanidins (C12644 )
Anthocyanidins and anthocyanins (C12644 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0303787)

Food

Fruit

Berry

Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Gooseberry (FooDB: FOOD00157)
Strawberry (FooDB: FOOD00083)
Red raspberry (FooDB: FOOD00162)
Black elderberry (FooDB: FOOD00166)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Lowbush blueberry (FooDB: FOOD00189)

Tropical fruit

French plantain (FooDB: FOOD00436)

Drupe

Sweet cherry (FooDB: FOOD00145)

Herb and spice

Oilseed crop

Flaxseed (FooDB: FOOD00101)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.87 g/L	ALOGPS
logP	0.73	ALOGPS
logP	-0.36	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	6.4	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	232.13 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	145.15 m³·mol⁻¹	ChemAxon
Polarizability	56.03 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

HMDB0303787

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021681

KNApSAcK ID

Not Available

Chemspider ID

391981

KEGG Compound ID

C12644

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

443917

PDB ID

Not Available

ChEBI ID

31968

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Pelargonidin 3-rutinoside (CFc000283303)

MOL for CFc000283303 (Pelargonidin 3-rutinoside)

3D MOL for CFc000283303 (Pelargonidin 3-rutinoside)

3D SDF for CFc000283303 (Pelargonidin 3-rutinoside)

3D-SDF for CFc000283303 (Pelargonidin 3-rutinoside)

PDB for CFc000283303 (Pelargonidin 3-rutinoside)

3D PDB for CFc000283303 (Pelargonidin 3-rutinoside)

SMILES for CFc000283303 (Pelargonidin 3-rutinoside)

INCHI for CFc000283303 (Pelargonidin 3-rutinoside)

Structure for CFc000283303 (Pelargonidin 3-rutinoside)

3D Structure for CFc000283303 (Pelargonidin 3-rutinoside)