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 Phytohub

Spectrum TypeInstrument TypeIon ModeCollision Energy LevelViewPeaks
Predicted LC-MS/MSNot AvailablePositivelowView Spectrum(31.01838972,0.3156146385);(45.03403978,0.6745323429);(47.04968984,0.3304217321);(57.03403978,0.2158349366);(75.04460446,0.466771137);(85.0289544,0.7766662075);(103.0395191,2.136271416);(105.0551691,0.5834844722);(115.0395191,0.2415518476);(133.0500838,0.8972238256);(135.0657338,0.3936131727);(145.0500838,1.002154574);(147.0657338,0.2905044057);(163.0606485,7.001512044);(165.0762985,0.375849657);(181.0712131,1.667333888);(269.1752843,0.6592854365);(271.1909343,0.6540880999);(285.1701989,1.010414925);(287.185849,0.9993719837);(327.1807636,0.2172949605);(329.1964136,0.2172949605);(331.2120637,0.2172949605);(387.201893,0.3125371609);(389.217543,0.3125371609);(391.2331931,0.3125371609);(413.217543,0.289437697);(417.2124576,0.2128765784);(419.2281077,0.2158756756);(431.2281077,11.9370255);(434.1212969,65.06278744)
Predicted LC-MS/MSNot AvailablePositivemedView Spectrum(43.01838972,1.413318233);(45.03403978,2.378206687);(47.04968984,0.6298372736);(55.01838972,0.4941408865);(57.03403978,0.6009223007);(59.04968984,0.6605093551);(73.0289544,0.6232517321);(75.04460446,0.7642669425);(85.0289544,0.5818663822);(103.0395191,0.7640764031);(105.0551691,0.4709321125);(145.0500838,7.003629083);(147.0657338,3.679089051);(149.0813839,0.5723998951);(163.0606485,10.81767573);(165.0762985,2.54844098);(181.0712131,0.4896910906);(255.1596342,0.8493497698);(257.1752843,0.8254517021);(259.1909343,0.8039267358);(269.1752843,0.4591358754);(285.1701989,0.6659045594);(287.185849,0.631155999);(399.201893,0.4897045565);(401.217543,0.4897045565);(413.217543,15.63174828);(417.2124576,0.5817339636);(419.2281077,0.7997786532);(431.2281077,32.87533776);(433.2073723,0.734697674);(434.1212969,9.670115781)
Predicted LC-MS/MSNot AvailablePositivehighView Spectrum(27.0234751,1.608965793);(43.01838972,5.580363399);(45.03403978,6.221173264);(57.03403978,2.011275299);(59.01330434,3.790838399);(61.0289544,2.046562246);(69.03403978,1.592567673);(73.0289544,3.335570728);(75.04460446,1.65270371);(85.0289544,1.483238667);(87.00821896,3.273388742);(89.02386902,3.160594607);(91.03951908,1.958353076);(101.023869,3.130303193);(103.0395191,5.412893371);(105.0551691,2.731326666);(111.08099,1.404109402);(113.09664,2.339837462);(127.0759046,3.218957319);(129.0915547,3.423894142);(131.1072047,2.366801664);(145.0500838,6.537645754);(147.0657338,7.003197673);(163.0606485,9.548856001);(267.1596342,1.696139342);(269.1752843,2.872340384);(269.1752843,1.459521229);(271.1909343,2.377455614);(285.1701989,2.763480049);(413.217543,2.431797371);(431.2281077,1.565847761)
Predicted LC-MS/MSNot AvailableNegativelowView Spectrum(17.00273965,0.3393821321);(31.01838972,0.3675591666);(41.00273965,0.4531810915);(43.01838972,0.933054055);(45.03403978,0.5815198163);(56.99765427,2.050256012);(59.01330434,1.457451302);(71.01330434,0.4077731681);(73.0289544,1.748755392);(85.0289544,0.4790203597);(87.00821896,1.805423609);(89.02386902,3.610798816);(91.03951908,0.392730764);(101.023869,0.5641296589);(103.0395191,3.90445571);(105.0551691,0.3666818238);(119.0344337,0.6381640426);(133.0500838,2.951734415);(135.0657338,0.6216045699);(149.0449984,1.396930122);(151.0606485,0.3304964749);(161.0449984,3.589264102);(177.039913,0.5076916852);(179.0555631,7.523372899);(325.1651135,0.2606301487);(327.1807636,0.2606301487);(355.1756782,0.2951966201);(357.1913283,0.2951966201);(359.2069783,0.2951966201);(429.2124576,6.173684092);(432.1056468,55.39803456)
Predicted LC-MS/MSNot AvailableNegativemedView Spectrum(17.00273965,1.019036865);(41.00273965,1.014039341);(43.01838972,4.666001528);(45.03403978,2.580855048);(56.99765427,0.6488006805);(59.01330434,4.217904797);(71.01330434,1.589022947);(73.0289544,7.255821802);(75.00821896,0.548129889);(75.04460446,0.9646529838);(87.00821896,0.6689460018);(89.02386902,1.587247303);(101.023869,1.762419637);(103.0395191,2.483795314);(105.0551691,0.6272525979);(115.0395191,0.5062355066);(117.0551691,0.7674029886);(131.0344337,2.08269565);(133.0500838,4.365164585);(135.0657338,0.5827433703);(149.0449984,1.194351959);(161.0449984,10.63812682);(177.039913,0.6332857901);(179.0555631,9.641528385);(267.1596342,0.5419632729);(269.1752843,0.5419632729);(285.1701989,0.4411116297);(415.1968076,1.324870002);(417.2124576,1.206976836);(429.2124576,7.731521566);(432.1056468,26.16613163)
Predicted LC-MS/MSNot AvailableNegativehighView Spectrum(29.00273965,1.554704734);(41.00273965,6.423159841);(43.01838972,16.83934554);(45.03403978,6.076215685);(55.01838972,1.550381208);(56.99765427,3.71100879);(59.01330434,10.37206011);(61.0289544,1.80877685);(67.01838972,1.04905645);(71.01330434,4.563990055);(73.0289544,7.642087258);(75.04460446,0.9512351889);(85.0289544,0.8998185204);(87.00821896,1.283725723);(89.02386902,5.148842007);(101.023869,1.727164106);(103.0395191,3.128209142);(109.0289544,1.524489427);(119.0344337,0.9994481411);(125.023869,2.332483309);(129.0551691,0.9434431217);(131.0344337,4.190601999);(131.0708192,1.361771181);(133.0500838,1.104419103);(143.0344337,0.8917316324);(147.0293483,2.279256244);(149.0449984,1.103586809);(161.0449984,4.656890578);(179.0555631,0.9978698416);(257.1752843,1.897344185);(285.1701989,0.9868832257)

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