precursor metabolite

Showing entry for Luteolin 7-O-glucuronide

Identification

PhytoHub ID
PHUB000897
Name
Luteolin 7-O-glucuronide
Systematic Name
Not Available
Synonyms
Not Available
CAS Number
Not Available
Average Mass
462.363
Monoisotopic Mass
462.07982602
Chemical Formula
C21H18O12
IUPAC Name
(2S,3S,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
InChI Key
VSUOKLTVXQRUSG-ZFORQUDYSA-N
InChI Identifier
InChI=1S/C21H18O12/c22-9-2-1-7(3-10(9)23)13-6-12(25)15-11(24)4-8(5-14(15)32-13)31-21-18(28)16(26)17(27)19(33-21)20(29)30/h1-6,16-19,21-24,26-28H,(H,29,30)/t16-,17-,18+,19-,21+/m0/s1
SMILES
[H][C@@]1(OC2=CC(O)=C3C(=O)C=C(OC3=C2)C2=CC(O)=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)
1.38e+00 g/l
LogS (ALOGPS)
-2.52
LogP (ALOGPS)
1.22
Hydrogen Acceptors
12
Hydrogen Donors
7
Rotatable Bond Count
4
Polar Surface Area
203.43999999999994
Refractivity
106.90659999999998
Polarizability
43.20025683808933
Formal Charge
0
Physiological Charge
-2
pKa (strongest basic)
-3.6868267780685726
pKa (strongest acidic)
2.7391979384789336
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
Flavones

Taxonomy as Metabolite

Metabolite Family
(Poly)phenol metabolites
Metabolite Class
Flavonoid metabolites
Metabolite Sub-class
Flavones (parent and host metabolites)

Taxonomy of its Food Phytochemical Precursor(s)

Food PhytochemicalFamilyClassSub-class
LuteolinPolyphenolsFlavonoidsFlavonesShow Food Phytochemical

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Flavonoids
Super-class
Phenylpropanoids and polyketides
Sub-class
Flavonoid glycosides
Direct Parent Name
Flavonoid-7-O-glucuronides
Alternative Parent Names
["1-hydroxy-2-unsubstituted benzenoids", "1-hydroxy-4-unsubstituted benzenoids", "3'-hydroxyflavonoids", "4'-hydroxyflavonoids", "5-hydroxyflavonoids", "Acetals", "Benzene and substituted derivatives", "Beta hydroxy acids and derivatives", "Carbonyl compounds", "Carboxylic acids", "Catechols", "Chromones", "Flavones", "Flavonoid-7-O-glycosides", "Heteroaromatic compounds", "Hexoses", "Hydrocarbon derivatives", "Monocarboxylic acids and derivatives", "O-glucuronides", "O-glycosyl compounds", "Organic oxides", "Oxacyclic compounds", "Oxanes", "Phenolic glycosides", "Polyols", "Pyranones and derivatives", "Secondary alcohols", "Vinylogous acids"]
External Descriptor Annotations
["Flavones and Flavonols", "flavones", "glycosyloxyflavone", "luteolin O-glucuronoside", "monosaccharide derivative", "trihydroxyflavone"]
Substituent Names
["1-benzopyran", "1-hydroxy-2-unsubstituted benzenoid", "1-hydroxy-4-unsubstituted benzenoid", "1-o-glucuronide", "3'-hydroxyflavonoid", "4'-hydroxyflavonoid", "5-hydroxyflavonoid", "Acetal", "Alcohol", "Aromatic heteropolycyclic compound", "Benzenoid", "Benzopyran", "Beta-hydroxy acid", "Carbonyl group", "Carboxylic acid", "Carboxylic acid derivative", "Catechol", "Chromone", "Flavone", "Flavonoid-7-o-glucuronide", "Flavonoid-7-o-glycoside", "Glucuronic acid or derivatives", "Glycosyl compound", "Heteroaromatic compound", "Hexose monosaccharide", "Hydrocarbon derivative", "Hydroxy acid", "Hydroxyflavonoid", "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", "Phenolic glycoside", "Polyol", "Pyran", "Pyranone", "Secondary alcohol", "Vinylogous acid"]

Spectra from Phytohub

Spectrum TypeInstrument TypeIon ModeCollision Energy LevelViewPeaks
Predicted GC-MSGC-MSEiNot AvailableView Spectrum(29.00219012,2.458294237);(44.99710422,2.54460608);(58.00492882,1.090607312);(59.01275342,4.383709592);(60.02057802,1.115410431);(87.00766752,0.9936921994);(88.01549212,1.420976663);(89.02331672,3.186182378);(90.03114132,1.465209888);(134.0209695,0.7920305324);(285.0393574,0.9572133687);(286.047182,2.51627794);(297.0393574,0.8445833042);(313.0342715,0.824008511);(314.0420961,1.034285873);(327.0499207,1.27388547);(328.0577453,0.8491718262);(343.0448348,1.457050029);(344.0526594,1.135225761);(356.0526594,0.9472008135);(357.060484,1.482756099);(358.0683086,1.073865278);(372.0475735,0.7724663238);(373.0553981,1.602112043);(374.0632227,1.028668287);(387.0710473,0.8609224776);(417.0816106,1.318908012);(431.0608755,0.8259459101);(432.0687001,0.7891303641);(444.0687001,2.298941364);(445.0765247,2.431050076)
Predicted GC-MSGC-MSEiNot AvailableView Spectrum(29.00219012,2.458294237);(44.99710422,2.54460608);(58.00492882,1.090607312);(59.01275342,4.383709592);(60.02057802,1.115410431);(87.00766752,0.9936921994);(88.01549212,1.420976663);(89.02331672,3.186182378);(90.03114132,1.465209888);(134.0209695,0.7920305324);(285.0393574,0.9572133687);(286.047182,2.51627794);(297.0393574,0.8445833042);(313.0342715,0.824008511);(314.0420961,1.034285873);(327.0499207,1.27388547);(328.0577453,0.8491718262);(343.0448348,1.457050029);(344.0526594,1.135225761);(356.0526594,0.9472008135);(357.060484,1.482756099);(358.0683086,1.073865278);(372.0475735,0.7724663238);(373.0553981,1.602112043);(374.0632227,1.028668287);(387.0710473,0.8609224776);(417.0816106,1.318908012);(431.0608755,0.8259459101);(432.0687001,0.7891303641);(444.0687001,2.298941364);(445.0765247,2.431050076)
LC-MS/MSNot AvailablePositiveNot AvailableView Spectrum(153.016,2.18);(287.055,100.0);(288.0562,1.23);(307.2453,1.07)
LC-MS/MSNot AvailableNegativeNot AvailableView Spectrum(285.04,100.0);(286.0385,3.4);(327.0473,1.98);(357.0585,3.12);(461.0706,95.55)
LC-MS/MSNot AvailablePositiveNot AvailableView Spectrum(287.0547,100.0);(385.2568,1.61);(389.1736,1.11);(463.0866,3.23)
LC-MS/MSNot AvailablePositiveNot AvailableView Spectrum(287.0548,100.0);(288.0516,1.18);(389.1778,1.68);(463.0869,97.84)
LC-MS/MSNot AvailableNegativeNot AvailableView Spectrum(59.0117,1.03);(113.0226,1.74);(285.0399,100.0);(286.0452,2.3);(461.0647,3.94)
LC-MS/MSNot AvailableNegativeNot AvailableView Spectrum(59.0111,1.26);(59.0137,2.09);(71.0155,1.48);(85.0256,1.02);(99.0101,1.01);(107.0134,1.46);(133.0293,5.79);(149.022,1.86);(151.0025,6.04);(175.0381,2.86);(199.036,2.35);(213.0535,1.06);(217.0461,2.18);(241.0513,1.35);(243.0346,1.0);(285.0398,100.0);(286.0374,1.78)
Predicted LC-MS/MSNot AvailablePositivelowView Spectrum(68.99765427,0.3805738823);(87.00821896,0.5423998961);(99.00821896,0.6481718629);(109.0289544,1.082950514);(111.0446045,0.2754929396);(117.0187836,0.7203842354);(147.0293483,0.3077910916);(159.0293483,0.8817731072);(161.0449984,0.3533004508);(175.0242629,0.3006344379);(177.039913,2.523005424);(195.0504777,0.3739618707);(257.0449984,0.2415977437);(269.0449984,12.97929431);(271.0606485,1.344218165);(275.0919486,0.2174748737);(277.1075986,0.2174748737);(285.039913,0.6228301598);(287.0555631,32.36319996);(291.0868632,0.4423235547);(315.0504777,0.2280950772);(353.0508716,0.3424377147);(401.0508716,0.2641721019);(417.0821717,0.5749976297);(427.0665217,1.956984196);(427.0665217,1.95350391);(427.0665217,0.9120557039);(445.0770864,12.07389975);(445.0770864,6.892206101);(445.0770864,0.2774117973);(463.087651,17.70538267)
Predicted LC-MS/MSNot AvailablePositivemedView Spectrum(43.01838972,0.5206080819);(87.00821896,0.2492143222);(109.0289544,1.642101934);(111.0446045,0.3468655936);(131.0344337,0.5665849844);(137.023869,0.399326486);(159.0293483,2.613488341);(161.0449984,0.5100302709);(177.039913,3.266398774);(179.0344337,0.5534286514);(203.0344337,0.3486229708);(229.0500838,0.4680025403);(239.0344337,0.5316159781);(243.0293483,0.2697713968);(245.0449984,0.5346665827);(255.0293483,1.564740325);(257.0449984,10.29982621);(269.0449984,23.44845709);(271.0606485,1.169712334);(285.039913,1.599521183);(287.0555631,39.94035854);(327.0504777,0.445341407);(329.0661278,0.2503659921);(417.0821717,0.7333003288);(427.0665217,0.5636793892);(427.0665217,1.246611783);(427.0665217,0.3843824139);(433.0770864,0.540690268);(445.0770864,2.122720616);(445.0770864,1.310157798);(463.087651,1.559407407)
Predicted LC-MS/MSNot AvailablePositivehighView Spectrum(43.01838972,1.872976465);(59.01330434,1.012664427);(87.00821896,3.905423909);(89.02386902,0.9953569877);(105.0187836,1.161460204);(109.0289544,6.196315433);(117.0187836,2.102251773);(131.0344337,1.407818836);(133.0289544,1.355235225);(135.0446045,1.657661563);(137.023869,2.720462982);(151.0395191,1.086765694);(153.0187836,1.745244293);(159.0293483,2.104588688);(161.0449984,2.407119361);(177.0187836,1.091291637);(177.039913,1.007329041);(179.0344337,2.345791015);(203.0344337,1.025979541);(229.0500838,4.770129749);(243.0293483,1.009870554);(245.0449984,1.913723838);(253.0500838,0.9890022394);(255.0293483,1.403291275);(257.0449984,3.599183239);(269.0449984,29.4057035);(271.0606485,2.59675007);(285.039913,1.504748445);(287.0555631,12.98132086);(291.0868632,1.42360013);(401.0508716,1.200939029)
Predicted LC-MS/MSNot AvailableNegativelowView Spectrum(41.00273965,0.8701328848);(59.01330434,0.7512350705);(71.01330434,2.124884032);(73.0289544,0.67358894);(87.00821896,1.597320972);(89.02386902,2.582838921);(101.023869,0.5334344767);(103.0031336,1.583138501);(103.0395191,0.4804356067);(109.0289544,0.783950174);(117.0187836,2.557278236);(133.0136983,0.4655582744);(147.0293483,1.977211372);(149.0449984,0.5640230065);(163.0242629,0.9003580518);(175.0242629,1.398546612);(193.0348276,1.14490099);(267.0293483,4.009497875);(269.0449984,0.4700101237);(285.039913,23.20381259);(327.0504777,1.465074978);(343.0453923,0.902585093);(357.0610424,0.6260227508);(387.0716071,0.4558010713);(399.0716071,2.638433939);(415.0665217,3.551448137);(417.0821717,7.615884423);(431.0614363,0.665404232);(443.0614363,2.604918643);(443.0614363,2.626348664);(461.072001,28.17592136)
Predicted LC-MS/MSNot AvailableNegativemedView Spectrum(41.00273965,1.018839735);(43.01838972,1.751025849);(59.01330434,1.879852925);(71.01330434,0.7570942562);(72.99256889,0.9667932086);(73.0289544,1.773760778);(87.00821896,2.266853636);(89.02386902,1.854377426);(103.0395191,2.462986439);(117.0187836,0.9635198634);(131.0344337,1.196833712);(145.0136983,1.078960731);(147.0293483,1.882434736);(149.0449984,0.9734825284);(175.0242629,2.156650018);(193.0348276,1.682794155);(241.0136983,0.7912923692);(243.0293483,3.104406442);(267.0293483,5.444492752);(269.0449984,0.7319654139);(283.0242629,1.110419357);(285.039913,42.45719185);(297.039913,1.304903733);(327.0504777,1.259392817);(343.0453923,1.11666107);(399.0716071,3.879665881);(415.0665217,2.179971204);(417.0821717,4.357778365);(443.0614363,1.249021201);(443.0614363,2.454487813);(461.072001,3.892089732)
Predicted LC-MS/MSNot AvailableNegativehighView Spectrum(41.00273965,2.019452301);(43.01838972,4.251124462);(56.99765427,0.9836280621);(59.01330434,3.437289838);(61.0289544,3.842924782);(71.01330434,1.344564796);(73.0289544,2.495491288);(83.01330434,1.457736582);(87.00821896,1.241242102);(103.0395191,0.8986884797);(109.0289544,0.8348177692);(131.0133043,0.8225532853);(131.0344337,4.058206224);(133.0289544,2.988119283);(135.008219,1.288534048);(147.0293483,1.192528624);(149.023869,1.985348442);(149.0449984,0.7080076772);(151.0031336,1.017978325);(201.0187836,1.424907371);(215.0344337,6.126566764);(229.0136983,0.8478717746);(241.0136983,2.842762018);(243.0293483,7.983266022);(255.0293483,1.751802543);(257.0449984,0.6321681316);(267.0293483,7.476186782);(269.0086129,0.732715359);(269.0449984,0.7909880518);(283.0242629,3.582717067);(285.039913,28.93981175)
Predicted LC-MS/MSNot AvailableNegativelowView Spectrum(285.04045,100.0);(461.07254,73.0)
Predicted LC-MS/MSNot AvailableNegativemediumView Spectrum(113.00328,11.0);(284.03263,100.0);(285.04045,100.0)
Predicted LC-MS/MSNot AvailableNegativehighView Spectrum(284.03263,100.0);(285.04045,100.0)
Predicted LC-MS/MSNot AvailablePositivelowView Spectrum(287.05501,100.0);(463.0871,50.0)
Predicted LC-MS/MSNot AvailablePositivemediumView Spectrum(287.05501,100.0)
Predicted LC-MS/MSNot AvailablePositivehighView Spectrum(287.05501,100.0)

Food Sources

NameGroup
LettuceVegetables, Leaf vegetables PublicationsShow

Food Sources of its Food Phytochemical(s)

Food PhytochemicalFood SourceFood Source Group
LuteolinAngelicaHerbs and Spices PublicationsShow
LuteolinAppleFruit, Pomes PublicationsShow
LuteolinBroccoliVegetables, Cabbages PublicationsShow
LuteolinCommon oreganoHerbs and Spices PublicationsShow
LuteolinCommon sageHerbs and Spices PublicationsShow
LuteolinCommon thymeHerbs and Spices PublicationsShow
LuteolinGlobe artichokeVegetables, Other vegetables PublicationsShow
LuteolinKiwiFruit, Tropical fruits PublicationsShow
LuteolinOlive, blackFruit, Drupes PublicationsShow
LuteolinPeppermintHerbs and Spices PublicationsShow
LuteolinRadicchioVegetables, Leaf vegetables PublicationsShow
LuteolinStrawberryFruit, Berries PublicationsShow

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Luteolin Luteolin 7-O-glucuronidehuman ratplasma, urinehost metabolism<1h0.5-2µmol/L<1%C21H18O12462.07982602 Publications

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
Back