precursor

Showing entry for Cyanidin 3-O-arabinoside

Identification

PhytoHub ID
PHUB000499
Name
Cyanidin 3-O-arabinoside
Systematic Name
Not Available
Synonyms
  • 3-[(2R,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-2-(3,4-dihydroxyphenyl)chromenylium-
CAS Number
Not Available
Average Mass
419.361
Monoisotopic Mass
419.097273232
Chemical Formula
C20H19O10
IUPAC Name
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2R,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-1lambda4-chromen-1-ylium
InChI Key
KUCVMQMKRICXJC-FEUVXWNVSA-O
InChI Identifier
InChI=1S/C20H18O10/c21-9-4-12(23)10-6-16(30-20-18(27)17(26)14(25)7-28-20)19(29-15(10)5-9)8-1-2-11(22)13(24)3-8/h1-6,14,17-18,20,25-27H,7H2,(H3-,21,22,23,24)/p+1/t14-,17-,18+,20+/m0/s1
SMILES
O[C@H]1CO[C@H](OC2=CC3=C(O)C=C(O)C=C3[O+]=C2C2=CC(O)=C(O)C=C2)[C@H](O)[C@H]1O
Structure
Similar Structures

Calculated Properties

Solubility (ALOGPS)
4.56e-01 g/l
LogS (ALOGPS)
-3.00
LogP (ALOGPS)
1.37
Hydrogen Acceptors
10
Hydrogen Donors
7
Rotatable Bond Count
3
Polar Surface Area
173.20999999999998
Refractivity
110.295
Polarizability
39.995557006783805
Formal Charge
1
Physiological Charge
-1
pKa (strongest basic)
-3.5265985690834403
pKa (strongest acidic)
6.388332879836749
Number of Rings
4
Rule of Five
No
Bioavailability
Yes
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'-hydroxyflavonoids", "4'-hydroxyflavonoids", "5-hydroxyflavonoids", "7-hydroxyflavonoids", "Acetals", "Anthocyanidins", "Benzene and substituted derivatives", "Catechols", "Heteroaromatic compounds", "Hydrocarbon derivatives", "Monosaccharides", "O-glycosyl compounds", "Organic cations", "Oxacyclic compounds", "Oxanes", "Polyols", "Secondary alcohols"]
External Descriptor Annotations
Not Available
Substituent Names
["1-benzopyran", "1-hydroxy-2-unsubstituted benzenoid", "1-hydroxy-4-unsubstituted benzenoid", "3'-hydroxyflavonoid", "4'-hydroxyflavonoid", "5-hydroxyflavonoid", "7-hydroxyflavonoid", "Acetal", "Alcohol", "Anthocyanidin", "Aromatic heteropolycyclic compound", "Benzenoid", "Benzopyran", "Catechol", "Flavonoid-3-o-glycoside", "Glycosyl compound", "Heteroaromatic compound", "Hydrocarbon derivative", "Hydroxyflavonoid", "Monocyclic benzene moiety", "Monosaccharide", "O-glycosyl compound", "Organic cation", "Organic oxygen compound", "Organoheterocyclic compound", "Organooxygen compound", "Oxacycle", "Oxane", "Phenol", "Polyol", "Secondary alcohol"]

Spectra from Online Resources

Record IDSourceDescriptionView
PR100451MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecifiedView Spectra
PR100909MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecifiedView Spectra

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
Cyanidin 3-O-arabinoside Cyanidin 3-O-arabinosidehumanplasma, urineunchanged1h-3h<20 nmol/LNot AvailableC20H19O10419.097273232 Detailed Intervention Studies Publications
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