precursor

Showing entry for Peonidin 3-O-arabinoside

Identification

PhytoHub ID
PHUB001651
Name
Peonidin 3-O-arabinoside
Systematic Name
Not Available
Synonyms
  • 3-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-2-(4-hydroxy-3-methoxyphenyl)chromen
  • 3,4',5,7-Tetrahydroxy-3'-methoxyflavylium(1+); 3-O-α-L-Arabinopyranoside
  • Peonidin 3-arabinoside
CAS Number
27214-74-0
Average Mass
449.387
Monoisotopic Mass
449.107837916
Chemical Formula
C21H21O11
IUPAC Name
2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-3-{[(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}-1lambda4-chromen-1-ylium
InChI Key
XYWFSSFJPFAYCA-BSOUQAEPSA-O
InChI Identifier
InChI=1S/C21H20O11/c1-29-15-3-8(2-12(24)17(15)26)20-16(32-21-19(28)18(27)13(25)7-30-21)6-10-11(23)4-9(22)5-14(10)31-20/h2-6,13,18-19,21,25,27-28H,7H2,1H3,(H3-,22,23,24,26)/p+1/t13-,18+,19-,21-/m1/s1
SMILES
COC1=CC(=CC(O)=C1O)C1=[O+]C2=CC(O)=CC(O)=C2C=C1O[C@H]1OC[C@@H](O)[C@H](O)[C@H]1O
Structure
Similar Structures

Calculated Properties

Solubility (ALOGPS)
3.38e-01 g/l
LogS (ALOGPS)
-3.16
LogP (ALOGPS)
1.42
Hydrogen Acceptors
11
Hydrogen Donors
7
Rotatable Bond Count
4
Polar Surface Area
182.43999999999997
Refractivity
116.7582
Polarizability
43.48847103361649
Formal Charge
1
Physiological Charge
-1
pKa (strongest basic)
-3.5265985690834403
pKa (strongest acidic)
6.394362066685298
Number of Rings
4
Rule of Five
No
Bioavailability
No
Ghose Filter
Yes
Veber's Rule
No
MDDR-like Rule
No

Taxonomy as Food Phytochemical

Family
Polyphenols
Class
Flavonoids
Sub-class
Anthocyanins

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Flavonoids
Super-class
Phenylpropanoids and polyketides
Sub-class
Flavonoid glycosides
Direct Parent Name
Flavonoid-3-O-glycosides
Alternative Parent Names
["1-benzopyrans", "1-hydroxy-2-unsubstituted benzenoids", "1-hydroxy-4-unsubstituted benzenoids", "3'-O-methylated flavonoids", "3'-hydroxyflavonoids", "4'-hydroxyflavonoids", "5-hydroxyflavonoids", "7-hydroxyflavonoids", "Acetals", "Alkyl aryl ethers", "Anisoles", "Anthocyanidins", "Catechols", "Heteroaromatic compounds", "Hydrocarbon derivatives", "Methoxybenzenes", "Methoxyphenols", "Monosaccharides", "O-glycosyl compounds", "Organic cations", "Oxacyclic compounds", "Oxanes", "Phenoxy compounds", "Polyols", "Secondary alcohols"]
External Descriptor Annotations
Not Available
Substituent Names
["1-benzopyran", "1-hydroxy-2-unsubstituted benzenoid", "1-hydroxy-4-unsubstituted benzenoid", "3'-hydroxyflavonoid", "3p-methoxyflavonoid-skeleton", "4'-hydroxyflavonoid", "5-hydroxyflavonoid", "7-hydroxyflavonoid", "Acetal", "Alcohol", "Alkyl aryl ether", "Anisole", "Anthocyanidin", "Aromatic heteropolycyclic compound", "Benzenoid", "Benzopyran", "Catechol", "Ether", "Flavonoid-3-o-glycoside", "Glycosyl compound", "Heteroaromatic compound", "Hydrocarbon derivative", "Hydroxyflavonoid", "Methoxybenzene", "Methoxyphenol", "Monocyclic benzene moiety", "Monosaccharide", "O-glycosyl compound", "Organic cation", "Organic oxygen compound", "Organoheterocyclic compound", "Organooxygen compound", "Oxacycle", "Oxane", "Phenol", "Phenol ether", "Phenoxy compound", "Polyol", "Secondary alcohol"]

Spectra from Online Resources

No spectra information available

Food Sources

NameGroup
American cranberryFruit, Berries PublicationsShow
CranberryFruit, Berries PublicationsShow
Cranberry juiceBeverages, Non-alcoholic PublicationsShow

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Peonidin 3-O-arabinoside Peonidin 3-O-arabinosidehumanplasma, urineunchanged1h-3h<20 nmol/L<1%C21H21O11449.107837916 Detailed Intervention Studies Publications
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