ChemFOnt: Showing chemical card for Petunidin 3-O-[6-O-(4-O-(E)-caffeoyl-O-alpha-rhamnopyranosyl)-beta-glucopyranoside]-5-O-beta-glucopyranoside (CFc000281518)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:32:59 UTC

Chemfont ID

CFc000281518

Molecule Identification

Common Name

Petunidin 3-O-[6-O-(4-O-(E)-caffeoyl-O-alpha-rhamnopyranosyl)-beta-glucopyranoside]-5-O-beta-glucopyranoside

Definition

Petunidin 3-o-[6-o-(4-o-(e)-caffeoyl-o-alpha-rhamnopyranosyl)-beta-glucopyranoside]-5-o-beta-glucopyranoside is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Petunidin 3-o-[6-o-(4-o-(e)-caffeoyl-o-alpha-rhamnopyranosyl)-beta-glucopyranoside]-5-o-beta-glucopyranoside can be found in potato, which makes petunidin 3-o-[6-o-(4-o-(e)-caffeoyl-o-alpha-rhamnopyranosyl)-beta-glucopyranoside]-5-o-beta-glucopyranoside a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Petunidin 3-O-[6-O-(4-O-(e)-caffeoyl-O-a-rhamnopyranosyl)-b-glucopyranoside]-5-O-b-glucopyranoside	Generator
Petunidin 3-O-[6-O-(4-O-(e)-caffeoyl-O-α-rhamnopyranosyl)-β-glucopyranoside]-5-O-β-glucopyranoside	Generator

Chemical Formula

C₄₃H₄₉O₂₄

Average Molecular Weight

949.8348

Monoisotopic Molecular Weight

949.261377496

IUPAC Name

2-(3,4-dihydroxy-5-methoxyphenyl)-3-{[(2S,3R,4S,5S,6R)-6-({[(2R,3R,4S,5R,6R)-5-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxy-6-methyloxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-7-hydroxy-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium

Traditional Name

CAS Registry Number

232617-23-1

SMILES

COC1=C(O)C(O)=CC(=C1)C1=[O+]C2=CC(O)=CC(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=C2C=C1O[C@@H]1O[C@H](CO[C@@H]2O[C@H](C)[C@H](OC(=O)\C=C\C3=CC(O)=C(O)C=C3)[C@@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C43H48O24/c1-15-39(67-29(49)6-4-16-3-5-20(46)21(47)7-16)35(55)38(58)41(61-15)60-14-28-32(52)34(54)37(57)43(66-28)64-26-12-19-23(62-40(26)17-8-22(48)30(50)25(9-17)59-2)10-18(45)11-24(19)63-42-36(56)33(53)31(51)27(13-44)65-42/h3-12,15,27-28,31-39,41-44,51-58H,13-14H2,1-2H3,(H4-,45,46,47,48,49,50)/p+1/t15-,27-,28-,31-,32-,33+,34+,35+,36-,37-,38-,39+,41-,42-,43-/m1/s1

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302002)

Food

Vegetable

Tuber

Potato (FooDB: FOOD00175)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.46 g/L	ALOGPS
logP	1.7	ALOGPS
logP	-0.43	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	6.66	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	22	ChemAxon
Hydrogen Donor Count	14	ChemAxon
Polar Surface Area	387.27 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	229.26 m³·mol⁻¹	ChemAxon
Polarizability	92.02 Å³	ChemAxon
Number of Rings	7	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

HMDB0302002

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001733

KNApSAcK ID

Not Available

Chemspider ID

30780093

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

157009813

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Petunidin 3-O-[6-O-(4-O-(E)-caffeoyl-O-alpha-rhamnopyranosyl)-beta-glucopyranoside]-5-O-beta-glucopyranoside (CFc000281518)

MOL for CFc000281518 (Petunidin 3-O-[6-O-(4-O-(E)-caffeoyl-O-alpha-rhamnopyranosyl)-beta-glucopyranoside]-5-O-beta-glucopyranoside)

3D MOL for CFc000281518 (Petunidin 3-O-[6-O-(4-O-(E)-caffeoyl-O-alpha-rhamnopyranosyl)-beta-glucopyranoside]-5-O-beta-glucopyranoside)

3D SDF for CFc000281518 (Petunidin 3-O-[6-O-(4-O-(E)-caffeoyl-O-alpha-rhamnopyranosyl)-beta-glucopyranoside]-5-O-beta-glucopyranoside)

3D-SDF for CFc000281518 (Petunidin 3-O-[6-O-(4-O-(E)-caffeoyl-O-alpha-rhamnopyranosyl)-beta-glucopyranoside]-5-O-beta-glucopyranoside)

PDB for CFc000281518 (Petunidin 3-O-[6-O-(4-O-(E)-caffeoyl-O-alpha-rhamnopyranosyl)-beta-glucopyranoside]-5-O-beta-glucopyranoside)

3D PDB for CFc000281518 (Petunidin 3-O-[6-O-(4-O-(E)-caffeoyl-O-alpha-rhamnopyranosyl)-beta-glucopyranoside]-5-O-beta-glucopyranoside)

SMILES for CFc000281518 (Petunidin 3-O-[6-O-(4-O-(E)-caffeoyl-O-alpha-rhamnopyranosyl)-beta-glucopyranoside]-5-O-beta-glucopyranoside)

INCHI for CFc000281518 (Petunidin 3-O-[6-O-(4-O-(E)-caffeoyl-O-alpha-rhamnopyranosyl)-beta-glucopyranoside]-5-O-beta-glucopyranoside)

Structure for CFc000281518 (Petunidin 3-O-[6-O-(4-O-(E)-caffeoyl-O-alpha-rhamnopyranosyl)-beta-glucopyranoside]-5-O-beta-glucopyranoside)

3D Structure for CFc000281518 (Petunidin 3-O-[6-O-(4-O-(E)-caffeoyl-O-alpha-rhamnopyranosyl)-beta-glucopyranoside]-5-O-beta-glucopyranoside)