PhytoHub: Showing entry for Isorhamnetin 3-O-glucuronide

Isorhamnetin 3-O-glucuronide

Identification

PhytoHub ID

PHUB000666

Name

Isorhamnetin 3-O-glucuronide

Systematic Name

Not Available

Synonyms

Not Available

CAS Number

36687-76-0

Average Mass

492.389

Monoisotopic Mass

492.090390704

Chemical Formula

C₂₂H₂₀O₁₃

IUPAC Name

(2S,3S,4S,5R,6S)-6-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

InChI Key

VVZWHOMBDMMRSC-NTKSAMNMSA-N

InChI Identifier

InChI=1S/C22H20O13/c1-32-11-4-7(2-3-9(11)24)18-19(14(26)13-10(25)5-8(23)6-12(13)33-18)34-22-17(29)15(27)16(28)20(35-22)21(30)31/h2-6,15-17,20,22-25,27-29H,1H3,(H,30,31)/t15-,16-,17+,20-,22+/m0/s1

SMILES

[H][C@@]1(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC(OC)=C(O)C=C2)O[C@]([H])(C(O)=O)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O

Structure

Similar Structures

Calculated Properties

Solubility (ALOGPS): 1.71e+00 g/l
LogS (ALOGPS): -2.46
LogP (ALOGPS): 1.40
Hydrogen Acceptors: 13
Hydrogen Donors: 7
Rotatable Bond Count: 5
Polar Surface Area: 212.66999999999993
Refractivity: 113.62519999999999
Polarizability: 45.48370646992349
Formal Charge: 0
Physiological Charge: -2
pKa (strongest basic): -3.686829748042071
pKa (strongest acidic): 2.647099411185527
Number of Rings: 4
Rule of Five: No
Bioavailability: No
Ghose Filter: No
Veber's Rule: No
MDDR-like Rule: No

External Links

PubChem: 5491630
Phenol-Explorer: 331
PeakForestCompound: 000523

Taxonomy as Metabolite

Family: (Poly)phenol metabolites
Class: Flavonoid metabolites
Sub-class: Flavonols (parent and host metabolites)

Taxonomy of its Food Phytochemical Precursor(s)

Food Phytochemical	Family	Class	Sub-class
Quercetin	Polyphenols	Flavonoids	Flavonols	Show Food Phytochemical
Quercetin 3,4'-O-diglucoside	Polyphenols	Flavonoids	Flavonols	Show Food Phytochemical
Quercetin 4'-O-glucoside	Polyphenols	Flavonoids	Flavonols	Show Food Phytochemical
Onion flavonols	Polyphenols	Flavonoids	Flavonols	Show Food Phytochemical

Classyfire Taxonomy

Kingdom Name: Organic compounds
Class: Flavonoids
Super-class: Phenylpropanoids and polyketides
Sub-class: Flavonoid glycosides
Direct Parent Name: Flavonoid-3-O-glucuronides
Alternative Parent Names: ["1-hydroxy-2-unsubstituted benzenoids", "1-hydroxy-4-unsubstituted benzenoids", "3'-O-methylated flavonoids", "4'-hydroxyflavonoids", "5-hydroxyflavonoids", "7-hydroxyflavonoids", "Acetals", "Alkyl aryl ethers", "Anisoles", "Beta hydroxy acids and derivatives", "Carbonyl compounds", "Carboxylic acids", "Chromones", "Flavones", "Flavonoid-3-O-glycosides", "Heteroaromatic compounds", "Hexoses", "Hydrocarbon derivatives", "Methoxybenzenes", "Methoxyphenols", "Monocarboxylic acids and derivatives", "O-glucuronides", "O-glycosyl compounds", "Organic oxides", "Oxacyclic compounds", "Oxanes", "Phenoxy compounds", "Polyols", "Pyranones and derivatives", "Secondary alcohols", "Vinylogous acids"]
External Descriptor Annotations: Not Available
Substituent Names: ["1-benzopyran", "1-hydroxy-2-unsubstituted benzenoid", "1-hydroxy-4-unsubstituted benzenoid", "1-o-glucuronide", "3p-methoxyflavonoid-skeleton", "4'-hydroxyflavonoid", "5-hydroxyflavonoid", "7-hydroxyflavonoid", "Acetal", "Alcohol", "Alkyl aryl ether", "Anisole", "Aromatic heteropolycyclic compound", "Benzenoid", "Benzopyran", "Beta-hydroxy acid", "Carbonyl group", "Carboxylic acid", "Carboxylic acid derivative", "Chromone", "Ether", "Flavone", "Flavonoid-3-o-glucuronide", "Flavonoid-3-o-glycoside", "Glucuronic acid or derivatives", "Glycosyl compound", "Heteroaromatic compound", "Hexose monosaccharide", "Hydrocarbon derivative", "Hydroxy acid", "Hydroxyflavonoid", "Methoxybenzene", "Methoxyphenol", "Monocarboxylic acid or derivatives", "Monocyclic benzene moiety", "Monosaccharide", "O-glucuronide", "O-glycosyl compound", "Organic oxide", "Organic oxygen compound", "Organoheterocyclic compound", "Organooxygen compound", "Oxacycle", "Oxane", "Phenol", "Phenol ether", "Phenoxy compound", "Polyol", "Pyran", "Pyranone", "Secondary alcohol", "Vinylogous acid"]

Spectra from Phytohub

Spectrum Type	Instrument Type	Ion Mode	Collision Energy Level	View	Peaks

Predicted GC-MS	GC-MS	Ei	Not Available	View Spectrum	(29.00219012,2.485112294);(44.99710422,2.506694403);(58.00492882,1.102748246);(59.01275342,4.302551809);(60.02057802,1.128028382);(87.00766752,1.004955948);(88.01549212,1.436795356);(89.02331672,3.174479061);(90.03114132,1.481520998);(118.0260554,0.7779680808);(134.0209695,0.8008476289);(313.0342715,0.8698589931);(316.0577453,1.152433535);(343.0448348,0.8222752217);(344.0526594,1.03211075);(357.060484,1.271250858);(358.0683086,0.8474159968);(373.0553981,1.454069842);(374.0632227,1.132904353);(386.0632227,0.9452967644);(387.0710473,1.479776192);(388.0788719,1.071707636);(402.0581368,0.7709308664);(403.0659614,1.59892823);(404.073786,1.026624543);(417.0816106,0.8592425588);(447.0921739,1.316411363);(461.0714388,0.8243995813);(462.0792634,0.7840452413);(474.0792634,2.407351464);(475.087088,2.465278125)
Predicted GC-MS	GC-MS	Ei	Not Available	View Spectrum	(29.00219012,2.485112294);(44.99710422,2.506694403);(58.00492882,1.102748246);(59.01275342,4.302551809);(60.02057802,1.128028382);(87.00766752,1.004955948);(88.01549212,1.436795356);(89.02331672,3.174479061);(90.03114132,1.481520998);(118.0260554,0.7779680808);(134.0209695,0.8008476289);(313.0342715,0.8698589931);(316.0577453,1.152433535);(343.0448348,0.8222752217);(344.0526594,1.03211075);(357.060484,1.271250858);(358.0683086,0.8474159968);(373.0553981,1.454069842);(374.0632227,1.132904353);(386.0632227,0.9452967644);(387.0710473,1.479776192);(388.0788719,1.071707636);(402.0581368,0.7709308664);(403.0659614,1.59892823);(404.073786,1.026624543);(417.0816106,0.8592425588);(447.0921739,1.316411363);(461.0714388,0.8243995813);(462.0792634,0.7840452413);(474.0792634,2.407351464);(475.087088,2.465278125)
Predicted LC-MS/MS	Not Available	Positive	low	View Spectrum	(68.99765427,0.4194874849);(87.00821896,0.6153536249);(99.00821896,0.7126036422);(117.0187836,0.8040088199);(125.0602545,0.4390111217);(147.0293483,0.339089865);(159.0293483,0.9545724198);(161.0449984,0.4025776669);(173.0086129,0.3327387045);(175.0242629,0.329237012);(177.039913,2.516010743);(285.039913,0.6295439623);(287.0555631,0.4978985057);(299.0555631,1.503625014);(299.0555631,0.5875655965);(301.0348276,1.911516506);(301.0712131,1.376089128);(315.0504777,0.6796156379);(317.0661278,36.59985486);(321.0974279,0.4840991372);(369.0457862,0.3030874764);(447.0927364,0.6456897683);(457.0770864,1.133483408);(457.0770864,2.338856456);(457.0770864,1.316775852);(461.072001,0.4970394323);(463.087651,0.3410009142);(475.087651,9.497323602);(475.087651,4.594014219);(475.087651,6.927894659);(493.0982157,20.27033476)
Predicted LC-MS/MS	Not Available	Positive	med	View Spectrum	(43.01838972,0.661839595);(87.00821896,0.3162242555);(125.0602545,0.4784228065);(131.0344337,0.63632134);(153.0187836,0.5211584397);(159.0293483,2.93793487);(161.0449984,0.61994734);(177.039913,3.41862186);(195.0293483,0.3551458147);(261.039913,0.3552705887);(273.039913,0.3261927373);(275.0555631,0.4790263557);(285.039913,5.239644983);(287.0555631,10.07253838);(289.0712131,0.4161266296);(299.0555631,5.912233779);(299.0555631,3.593912439);(301.0348276,5.679212687);(301.0712131,1.111112784);(315.0504777,1.699096722);(317.0661278,44.71292364);(357.0610424,0.4018121121);(447.0927364,0.8996650935);(457.0770864,1.541413268);(457.0770864,0.75287231);(461.072001,0.3983169273);(463.087651,0.4901109336);(475.087651,1.813471837);(475.087651,0.9392928251);(475.087651,1.262977474);(493.0982157,1.957159166)
Predicted LC-MS/MS	Not Available	Positive	high	View Spectrum	(43.01838972,2.297360999);(59.01330434,1.010326671);(68.99765427,0.848509226);(73.0289544,1.055651867);(87.00821896,4.091377291);(89.02386902,1.217608161);(105.0187836,1.15898231);(109.0289544,0.8556985401);(117.0187836,2.438441299);(131.0344337,1.404568858);(137.023869,5.043871607);(137.0602545,2.525857012);(151.0395191,3.528439168);(153.0187836,6.874532227);(155.0344337,1.106743486);(159.0293483,2.099368268);(161.0449984,1.913412415);(207.0293483,0.9198939764);(233.0449984,0.8658877411);(245.0449984,2.546209167);(261.0762985,1.728317945);(273.039913,1.28127354);(275.0555631,0.9774048871);(285.039913,5.336015119);(287.0555631,3.718880293);(299.0555631,8.04216499);(299.0555631,3.285380907);(301.0348276,13.0159787);(301.0712131,2.90077249);(315.0504777,2.261192065);(317.0661278,13.64987877)
Predicted LC-MS/MS	Not Available	Negative	low	View Spectrum	(41.00273965,0.8605651805);(59.01330434,0.6800966472);(71.01330434,2.116892012);(73.0289544,0.6516881229);(87.00821896,1.398166715);(103.0031336,1.731707876);(117.0187836,2.645048954);(123.0446045,0.9367721034);(133.0136983,0.5480104218);(147.0293483,2.154439848);(161.023869,0.5064111924);(175.0242629,1.35720181);(297.039913,0.9733039664);(299.0191776,2.275876025);(315.0504777,21.94561269);(339.0352216,1.224213953);(355.0665217,0.6129445313);(357.0610424,1.612385279);(367.0301362,0.6500556887);(373.055957,0.9865215989);(387.0716071,0.6848562615);(417.0821717,0.5377839375);(429.0821717,2.650770511);(431.0614363,0.6250902692);(445.0770864,3.872870952);(447.0927364,8.081247549);(461.072001,0.7260767162);(473.072001,1.288720403);(473.072001,1.625139887);(473.072001,2.479078932);(491.0825657,31.56044997)
Predicted LC-MS/MS	Not Available	Negative	med	View Spectrum	(43.01838972,1.805740745);(59.01330434,1.706849121);(72.99256889,1.046930153);(73.0289544,1.710651869);(87.00821896,2.608599199);(103.0395191,1.666036608);(117.0187836,1.006912365);(145.0136983,0.9392074336);(147.0293483,2.000259066);(175.0242629,1.132564495);(259.0242629,3.50463324);(259.0606485,1.116980442);(273.039913,1.06641215);(283.0242629,2.897038848);(285.039913,1.612382228);(297.039913,2.481898584);(299.0191776,13.73951352);(299.0555631,0.9607217852);(313.0348276,1.21298906);(315.0504777,31.10064707);(357.0610424,1.428547352);(373.055957,1.210034322);(429.0821717,2.891153051);(431.0614363,2.229043775);(445.0770864,2.537301604);(447.0927364,4.226393308);(473.072001,0.9809500068);(473.072001,1.267945612);(473.072001,2.395784018);(475.0512655,1.246589926);(491.0825657,4.269289041)
Predicted LC-MS/MS	Not Available	Negative	high	View Spectrum	(41.00273965,2.160024841);(43.01838972,3.74651976);(56.99765427,1.148310892);(59.01330434,3.042888085);(61.0289544,3.372917075);(71.01330434,1.260786345);(73.0289544,1.533819434);(107.0133043,1.432675693);(109.0289544,1.068497411);(125.023869,2.951430007);(131.0344337,3.732144089);(135.008219,3.649345939);(147.0293483,0.8397548385);(151.0031336,2.021254329);(163.0395191,1.179702671);(217.0500838,0.8546468104);(229.0136983,1.141272541);(255.0293483,1.017785077);(257.0086129,1.428068385);(259.0242629,0.9116136131);(259.0242629,1.186575586);(259.0606485,1.685216614);(271.0242629,1.389892411);(273.039913,2.693164292);(283.0242629,3.36818515);(285.039913,6.551062923);(295.0453923,0.898693189);(297.039913,2.23247999);(299.0191776,19.00504391);(313.0348276,3.123260539);(315.0504777,19.37296756)
Predicted LC-MS/MS	Not Available	Negative	low	View Spectrum	(315.05102,2.0);(491.08311,100.0)
Predicted LC-MS/MS	Not Available	Negative	medium	View Spectrum	(314.04319,26.0);(315.05102,30.0);(491.08311,100.0)
Predicted LC-MS/MS	Not Available	Negative	high	View Spectrum	(151.00367,7.0);(255.02989,17.0);(285.04045,14.0);(314.04319,100.0);(315.05102,49.0);(491.08311,17.0)
Predicted LC-MS/MS	Not Available	Positive	low	View Spectrum	(317.06557,100.0);(493.09766,29.0)
Predicted LC-MS/MS	Not Available	Positive	medium	View Spectrum	(317.06557,100.0);(493.09766,100.0)
Predicted LC-MS/MS	Not Available	Positive	high	View Spectrum	(85.0284,7.0);(317.06557,100.0)

Food Sources

No food source information available

Food Sources of its Food Phytochemical(s)

Food Phytochemical	Food Source	Food Source Group
Quercetin	Acerola	Fruit, Tropical fruits	Publications	Show
Quercetin	American cranberry	Fruit, Berries	Publications	Show
Quercetin	Angelica	Herbs and Spices	Publications	Show
Quercetin	Apple	Fruit, Pomes	Publications	Show
Quercetin	Apple juice	Beverages, Non-alcoholic	Publications	Show
Quercetin	Black tea	Teas and herbal teas	Publications	Show
Quercetin	Blackberry	Fruit, Berries	Publications	Show
Quercetin	Broccoli	Vegetables, Cabbages	Publications	Show
Quercetin	Cherry tomato	Vegetables, Fruit vegetables	Publications	Show
Quercetin	European cranberry	Fruit, Berries	Publications	Show
Quercetin	Green tea	Teas and herbal teas	Publications	Show
Quercetin	Lettuce	Vegetables, Leaf vegetables	Publications	Show
Quercetin	Onion	Vegetables, Onion-family	Publications	Show
Quercetin 3,4'-O-diglucoside	Onion	Vegetables, Onion-family	Publications	Show
Quercetin 4'-O-glucoside	Onion	Vegetables, Onion-family	Publications	Show
Quercetin	Orange juice	Beverages, Non-alcoholic	Publications	Show
Quercetin	Parsnip	Vegetables, Root vegetables	Publications	Show
Quercetin	Tomato	Vegetables, Fruit vegetables	Publications	Show
Quercetin 3,4'-O-diglucoside	red onion	Vegetables, Onion-family	Publications	Show
Quercetin 4'-O-glucoside	red onion	Vegetables, Onion-family	Publications	Show

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food Phytochemical	Metabolite	Species	Biofluids	Origin	TMax	CMax	Urinary Excretion	Formula	Monoisotopic mass
Quercetin	Isorhamnetin 3-O-glucuronide	human	plasma, urine	host metabolism	Not Available	Not Available	Not Available	C₂₂H₂₀O₁₃	492.090390704	Publications
Quercetin 3,4'-O-diglucoside	Isorhamnetin 3-O-glucuronide	human	plasma	Not Available	Not Available	Not Available	Not Available	C₂₂H₂₀O₁₃	492.090390704	Publications
Quercetin 4'-O-glucoside	Isorhamnetin 3-O-glucuronide	human	plasma	host-gut microbiota co-metabolite	Not Available	Not Available	Not Available	C₂₂H₂₀O₁₃	492.090390704	Publications
Onion flavonols	Isorhamnetin 3-O-glucuronide	human	plasma, urine	unknown	<1h	50-200 nmol/L	<1%	C₂₂H₂₀O₁₃	492.090390704	Publications

Inter-Individual Variations in Metabolism

	Food Phytochemical		Metabolite	Effect	Value

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Showing entry for Isorhamnetin 3-O-glucuronide