precursor

Showing entry for Pelargonidin 3-O-glucoside

Identification

PhytoHub ID
PHUB000506
Name
Pelargonidin 3-O-glucoside
Systematic Name
Not Available
Synonyms
  • 3-(beta-D-Glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-1-benzopyrylium chloride
  • 3-(β-D-glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)chromenylium chloride
  • 3-(β-D-glucopyranosyloxy)-5,7-dihydroxy-4'-hydroxyflavylium
  • 3,4',5,7-Tetrahydroxyflavylium(1+); 3-O-β-D-Glucopyranoside
  • callistephin
  • Pelargonidin 3-glucoside
  • pelargonidin 3-O-β-D-glucoside
  • Pelargonidin-3-glucopyranoside
CAS Number
18466-51-8
Average Mass
433.388
Monoisotopic Mass
433.112923296
Chemical Formula
C21H21O10
IUPAC Name
5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1lambda4-chromen-1-ylium
InChI Key
ABVCUBUIXWJYSE-UNJWAJPSSA-O
InChI Identifier
InChI=1S/C21H20O10/c22-8-16-17(26)18(27)19(28)21(31-16)30-15-7-12-13(25)5-11(24)6-14(12)29-20(15)9-1-3-10(23)4-2-9/h1-7,16-19,21-22,26-28H,8H2,(H2-,23,24,25)/p+1/t16-,17-,18+,19-,21-/m0/s1
SMILES
OC[C@@H]1O[C@H](OC2=CC3=C(O)C=C(O)C=C3[O+]=C2C2=CC=C(O)C=C2)[C@@H](O)[C@H](O)[C@H]1O
Structure
Similar Structures

Calculated Properties

Solubility (ALOGPS)
4.61e-01 g/l
LogS (ALOGPS)
-3.01
LogP (ALOGPS)
1.13
Hydrogen Acceptors
10
Hydrogen Donors
7
Rotatable Bond Count
4
Polar Surface Area
173.20999999999998
Refractivity
114.2766
Polarizability
41.80490662500228
Formal Charge
1
Physiological Charge
-1
pKa (strongest basic)
-2.9810923799280262
pKa (strongest acidic)
6.396818378835825
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
Anthocyanidin-3-O-glycosides
Alternative Parent Names
["1-benzopyrans", "1-hydroxy-2-unsubstituted benzenoids", "1-hydroxy-4-unsubstituted benzenoids", "4'-hydroxyflavonoids", "5-hydroxyflavonoids", "7-hydroxyflavonoids", "Acetals", "Anthocyanidins", "Benzene and substituted derivatives", "Flavonoid-3-O-glycosides", "Heteroaromatic compounds", "Hexoses", "Hydrocarbon derivatives", "O-glycosyl compounds", "Organic cations", "Oxacyclic compounds", "Oxanes", "Polyols", "Primary alcohols", "Secondary alcohols"]
External Descriptor Annotations
Not Available
Substituent Names
["1-benzopyran", "1-hydroxy-2-unsubstituted benzenoid", "1-hydroxy-4-unsubstituted benzenoid", "4'-hydroxyflavonoid", "5-hydroxyflavonoid", "7-hydroxyflavonoid", "Acetal", "Alcohol", "Anthocyanidin", "Anthocyanidin-3-o-glycoside", "Aromatic heteropolycyclic compound", "Benzenoid", "Benzopyran", "Flavonoid-3-o-glycoside", "Glycosyl compound", "Heteroaromatic compound", "Hexose monosaccharide", "Hydrocarbon derivative", "Hydroxyflavonoid", "Monocyclic benzene moiety", "Monosaccharide", "O-glycosyl compound", "Organic cation", "Organic oxygen compound", "Organoheterocyclic compound", "Organooxygen compound", "Oxacycle", "Oxane", "Phenol", "Polyol", "Primary alcohol", "Secondary alcohol"]

Spectra from Online Resources

Record IDSourceDescriptionView
PR040157MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, [M-2H]-View Spectra
PR040158MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, [M-2H+H2O]-View Spectra
PR040159MassBankLC-ESI-QTOF Spectrum - 30 V, [M-2H]-View Spectra
PR040160MassBankLC-ESI-QTOF Spectrum - 30 V, [M-2H+H2O]-View Spectra
PR040161MassBankLC-ESI-QTOF Spectrum - 30 V, [M]+View Spectra
PR040162MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, [M]+View Spectra
PR100250MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecifiedView Spectra
PR100672MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecifiedView Spectra

Food Sources

NameGroup
StrawberryFruit, Berries PublicationsShow

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Pelargonidin 3-O-glucoside Pelargonidin 3-O-glucosidehumanplasma, urineunchanged1h-3h<20 nmol/L<1%C21H21O10433.112923296 Detailed Intervention Studies Publications
Pelargonidin 3-O-glucoside 3-(1-Carboxy-4-hydroxyphenyl)beta-D-glucuronic acidNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableC13H14O10330.058696651 Publications
Pelargonidin 3-O-glucoside 4-(1-Carboxy-3-hydroxyphenyl)beta-D-glucuronic acidNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableC13H14O10330.058696651 Publications
Pelargonidin 3-O-glucoside 4-(1-Carboxyphenyl)beta-D-glucuronic acidNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableC13H14O9314.063782031 Publications
Pelargonidin 3-O-glucoside Pelargonidin glucuronidehuman pigurineNot AvailableNot AvailableNot AvailableNot AvailableC22H21O11461.4026627 Publications
Pelargonidin 3-O-glucoside Pelargonidin sulfatehumanurineNot AvailableNot AvailableNot AvailableNot AvailableC15H11O8S351.3121191 Publications
Back