ChemFOnt: Showing chemical card for Peonidin 3-rutinoside (CFc000283165)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:36:11 UTC

Chemfont ID

CFc000283165

Molecule Identification

Common Name

Peonidin 3-rutinoside

Definition

Peonidin 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. Peonidin 3-rutinoside is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Peonidin 3-rutinoside can be found in a number of food items such as european plum, blackcurrant, lima bean, and french plantain, which makes peonidin 3-rutinoside a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₈H₃₃O₁₅

Average Molecular Weight

609.5526

Monoisotopic Molecular Weight

609.181945386

IUPAC Name

5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-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-hydroxy-3-methoxyphenyl)-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

27539-32-8

SMILES

[H][C@@]1(C)O[C@@]([H])(OC[C@@]2([H])O[C@@]([H])(OC3=CC4=C(C=C(O)C=C4O)[O+]=C3C3=CC(OC)=C(O)C=C3)[C@]([H])(O)[C@@]([H])(O)[C@]2([H])O)[C@]([H])(O)[C@]([H])(O)[C@@]1([H])O

InChI Identifier

InChI=1S/C28H32O15/c1-10-20(32)22(34)24(36)27(40-10)39-9-19-21(33)23(35)25(37)28(43-19)42-18-8-13-15(31)6-12(29)7-16(13)41-26(18)11-3-4-14(30)17(5-11)38-2/h3-8,10,19-25,27-28,32-37H,9H2,1-2H3,(H2-,29,30,31)/p+1/t10-,19+,20-,21+,22+,23-,24+,25+,27+,28+/m0/s1

InChI Key

ONQVTPMFYSRRLL-HUJUZFAXSA-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
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
Anthocyanidin
Disaccharide
O-glycosyl compound
Glycosyl compound
1-benzopyran
Benzopyran
Methoxyphenol
Methoxybenzene
Anisole
Phenoxy compound
Phenol ether
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Oxane
Heteroaromatic compound
Secondary alcohol
Polyol
Organoheterocyclic compound
Acetal
Oxacycle
Ether
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organooxygen compound
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0303649)

Food

Vegetable

Shoot vegetable

Asparagus (FooDB: FOOD00021)

Fruit

Tropical fruit

Banana (FooDB: FOOD00208)
French plantain (FooDB: FOOD00436)

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)
Lowbush blueberry (FooDB: FOOD00189)

Drupe

Prunus (Cherry, Plum) (FooDB: FOOD00143)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)

Herb and spice

Herb

Rose hip (FooDB: FOOD00446)

Cereal and cereal product

Cereal

Rye (FooDB: FOOD00169)
Common wheat (FooDB: FOOD00187)

Pulse

Bean

Lima bean (FooDB: FOOD00133)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.72 g/L	ALOGPS
logP	0.77	ALOGPS
logP	-0.61	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	6.4	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	241.36 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	151.61 m³·mol⁻¹	ChemAxon
Polarizability	58.81 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

HMDB0303649

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB017305

KNApSAcK ID

Not Available

Chemspider ID

30780113

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 Peonidin 3-rutinoside (CFc000283165)

MOL for CFc000283165 (Peonidin 3-rutinoside)

3D MOL for CFc000283165 (Peonidin 3-rutinoside)

3D SDF for CFc000283165 (Peonidin 3-rutinoside)

3D-SDF for CFc000283165 (Peonidin 3-rutinoside)

PDB for CFc000283165 (Peonidin 3-rutinoside)

3D PDB for CFc000283165 (Peonidin 3-rutinoside)

SMILES for CFc000283165 (Peonidin 3-rutinoside)

INCHI for CFc000283165 (Peonidin 3-rutinoside)

Structure for CFc000283165 (Peonidin 3-rutinoside)

3D Structure for CFc000283165 (Peonidin 3-rutinoside)