PhytoHub: Showing entry for Genistein 4'-O-glucuronide

Genistein 4'-O-glucuronide

Identification

PhytoHub ID

PHUB002127

Name

Genistein 4'-O-glucuronide

Systematic Name

(2S,3S,4S,5R,6S)-6-[4-(5,7-dihydroxy-4-oxochromen-3-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

Synonyms

Not Available

CAS Number

Not Available

Average Mass

446.364

Monoisotopic Mass

446.0849114

Chemical Formula

C₂₁H₁₈O₁₁

IUPAC Name

(2S,3S,4S,5R,6S)-6-[4-(5,7-dihydroxy-4-oxo-4H-chromen-3-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

InChI Key

NHEBJNCJBWUPCK-ZFORQUDYSA-N

InChI Identifier

InChI=1S/C21H18O11/c22-9-5-12(23)14-13(6-9)30-7-11(15(14)24)8-1-3-10(4-2-8)31-21-18(27)16(25)17(26)19(32-21)20(28)29/h1-7,16-19,21-23,25-27H,(H,28,29)/t16-,17-,18+,19-,21+/m0/s1

SMILES

O[C@@H]1[C@@H](O)[C@H](OC2=CC=C(C=C2)C2=COC3=C(C(O)=CC(O)=C3)C2=O)O[C@@H]([C@H]1O)C(O)=O

Structure

Similar Structures

Calculated Properties

Solubility (ALOGPS): 1.05e+00 g/l
LogS (ALOGPS): -2.63
LogP (ALOGPS): 0.99
Hydrogen Acceptors: 11
Hydrogen Donors: 6
Rotatable Bond Count: 4
Polar Surface Area: 183.21
Refractivity: 103.69469999999998
Polarizability: 42.23393987941993
Formal Charge: 0
Physiological Charge: -2
pKa (strongest basic): -3.686826761383337
pKa (strongest acidic): 3.1858610011957627
Number of Rings: 4
Rule of Five: No
Bioavailability: No
Ghose Filter: Yes
Veber's Rule: No
MDDR-like Rule: No

External Links

No external links

Taxonomy as Metabolite

Family: (Poly)phenol metabolites
Class: Flavonoid metabolites
Sub-class: Isoflavones (parent, host and microbial metabolites)

Taxonomy of its Food Phytochemical Precursor(s)

Food Phytochemical	Family	Class	Sub-class
Genistin	Polyphenols	Flavonoids	Isoflavones	Show Food Phytochemical
Genistein	Polyphenols	Flavonoids	Isoflavones	Show Food Phytochemical

Spectra from Phytohub

Spectrum Type	Instrument Type	Ion Mode	Collision Energy Level	View	Peaks

Predicted GC-MS	GC-MS	Positive	Not Available	View Spectrum	(29.00219012,0.8994818586);(44.99710422,2.042008529);(56.99710422,0.8393350239);(58.00492882,1.391796645);(59.01275342,7.958619946);(60.02057802,1.95395317);(61.02840262,0.8301201907);(87.00766752,1.180099292);(88.01549212,0.9725680765);(89.02331672,2.877625863);(90.03114132,1.396558907);(103.0025816,1.006201286);(117.0182308,1.499169651);(134.0209695,1.265041118);(270.0522679,2.971945587);(271.0600925,0.8913575144);(298.047182,0.9878481566);(311.0550066,1.487663173);(312.0628312,1.35972598);(326.0420961,1.073589162);(327.0499207,1.511460918);(328.0577453,1.029711006);(340.0577453,0.904635363);(342.0733945,1.025607254);(356.0526594,0.9802652473);(358.0683086,1.169590194);(401.0866965,1.259581987);(415.0659614,0.8860577996);(416.073786,0.8275617039);(428.073786,2.331193387);(429.0816106,2.439099669)
Predicted GC-MS	GC-MS	Positive	Not Available	View Spectrum	(44.99710422,1.737945856);(73.04679982,3.322415838);(74.05462442,0.6348505522);(89.04171392,1.159414576);(115.0573631,0.6738647229);(175.0421054,0.9131612258);(203.091801,2.638128946);(204.0996256,1.679367591);(233.1023643,0.7127328214);(270.0522679,3.074438995);(271.0600925,0.9042445014);(305.1418881,1.38370611);(306.1497127,1.683362208);(383.0945304,1.186765612);(384.102355,0.8536219552);(399.0894445,0.6633941752);(400.0972691,0.8008389495);(485.1446175,1.087740853);(486.1524421,0.8616214112);(501.1395316,1.206848614);(502.1473562,1.340097588);(572.1528336,0.7884345004);(573.1606582,2.090295943);(574.1631261,0.8616285479);(588.2025292,0.8880793937);(589.1555723,0.9955419398);(590.1633969,0.7471076685);(617.2052679,1.157850284);(647.1794469,8.550421609);(648.1816622,4.159790809);(649.1806864,2.017581809)
Predicted GC-MS	GC-MS	Ei	Not Available	View Spectrum	(29.00219012,0.8994818586);(44.99710422,2.042008529);(56.99710422,0.8393350239);(58.00492882,1.391796645);(59.01275342,7.958619946);(60.02057802,1.95395317);(61.02840262,0.8301201907);(87.00766752,1.180099292);(88.01549212,0.9725680765);(89.02331672,2.877625863);(90.03114132,1.396558907);(103.0025816,1.006201286);(117.0182308,1.499169651);(134.0209695,1.265041118);(270.0522679,2.971945587);(271.0600925,0.8913575144);(298.047182,0.9878481566);(311.0550066,1.487663173);(312.0628312,1.35972598);(326.0420961,1.073589162);(327.0499207,1.511460918);(328.0577453,1.029711006);(340.0577453,0.904635363);(342.0733945,1.025607254);(356.0526594,0.9802652473);(358.0683086,1.169590194);(401.0866965,1.259581987);(415.0659614,0.8860577996);(416.073786,0.8275617039);(428.073786,2.331193387);(429.0816106,2.439099669)
Predicted LC-MS/MS	Not Available	Positive	low	View Spectrum	(177.0393644,2.131084837);(269.0655792,2.343797037);(271.0600999,34.49483525);(411.0710585,4.448613998);(429.0816232,23.32334723);(447.0921878,15.4761158)
Predicted LC-MS/MS	Not Available	Positive	med	View Spectrum	(95.04914126,1.626754071);(159.0287997,2.240937129);(177.0393644,3.041304481);(227.0338851,1.31472525);(229.0495352,1.373155013);(241.0495352,2.928603558);(243.0651853,4.542200437);(255.0651853,1.675085063);(271.0600999,54.55903991);(411.0710585,2.029227975);(429.0816232,4.180420082);(447.0921878,1.628956062)
Predicted LC-MS/MS	Not Available	Positive	high	View Spectrum	(41.00219107,0.9668292748);(43.01784114,1.221707843);(59.01275576,1.237112264);(63.02292652,1.199476138);(68.99710569,1.071089536);(87.00767038,1.62313889);(95.04914126,2.652726834);(105.0182351,0.8173383042);(105.0334912,4.689122844);(107.0491413,0.8027030334);(115.002585,0.7414141484);(117.0182351,1.270715544);(117.0334912,1.566912097);(119.0491413,3.317461802);(131.0338851,0.9726885141);(153.0182351,3.314562066);(157.0131497,0.816833471);(159.0287997,1.329052563);(161.0233204,1.564685343);(165.0182351,1.285403604);(201.0182351,0.8280665016);(227.0338851,1.709471711);(229.0495352,2.172078728);(239.0338851,1.449786174);(241.0495352,4.26789423);(243.0651853,6.863391994);(249.0393644,0.7686582483);(255.0287997,0.7378487711);(255.0651853,3.657768541);(271.0600999,14.25695713);(275.0914,1.092132368)
Predicted LC-MS/MS	Not Available	Negative	low	View Spectrum	(71.01385292,1.889210337);(89.0244176,2.150550521);(103.0036822,1.338766011);(117.0193322,2.169473958);(147.0298969,1.576185579);(177.0193322,1.29857029);(269.045547,22.25039253);(311.0561117,1.346832403);(383.077241,2.466083659);(399.0721556,3.333097131);(401.0878057,6.808589188);(427.0670703,8.302289381);(445.0776349,25.27043957)
Predicted LC-MS/MS	Not Available	Negative	med	View Spectrum	(41.00328823,1.079595659);(43.0189383,1.349317339);(59.01385292,2.060195178);(73.02950298,1.408951079);(87.00876754,1.708243695);(89.0244176,1.124741855);(103.0400677,1.848098357);(131.0349823,1.328934785);(177.0193322,4.546042946);(241.0506323,2.390632642);(269.045547,41.29949755);(311.0561117,1.097755831);(371.077241,0.9698724876);(383.077241,3.176407889);(399.0721556,2.308642331);(401.0878057,3.400202726);(417.0827203,1.522607573);(427.0670703,5.00311727);(445.0776349,3.057506058)
Predicted LC-MS/MS	Not Available	Negative	high	View Spectrum	(41.00328823,1.555404695);(43.0189383,3.777595318);(59.01385292,3.122071351);(61.02950298,3.229277864);(73.02950298,2.205303427);(105.0345884,1.224685431);(109.029503,1.69830583);(117.0345884,2.415440301);(131.0349823,2.572806883);(133.029503,1.059648691);(177.0193322,1.130198637);(227.0349823,5.860407469);(239.0349823,1.894345316);(241.0506323,16.27948178);(269.045547,31.04622947);(371.077241,1.123146342)
Predicted LC-MS/MS	Not Available	Positive	low	View Spectrum	(177.03936,9.34);(177.03936,9.34);(177.03936,9.34);(177.03936,9.34);(177.03936,9.34);(271.0601,28.14);(271.0601,28.14);(271.0601,28.14);(271.0601,28.14);(271.0601,28.14);(271.0601,28.14);(271.0601,28.14);(271.0601,28.14);(429.08162,20.72);(429.08162,20.72);(429.08162,20.72);(429.08162,20.72);(429.08162,20.72);(429.08162,20.72);(429.08162,20.72);(429.08162,20.72);(429.08162,20.72);(429.08162,20.72);(429.08162,20.72);(429.08162,20.72);(429.08162,20.72);(429.08162,20.72);(429.08162,20.72);(429.08162,20.72);(429.08162,20.72);(447.09219,100.0);(447.09219,100.0);(447.09219,100.0);(447.09219,100.0);(447.09219,100.0);(447.09219,100.0);(447.09219,100.0);(447.09219,100.0);(447.09219,100.0);(447.09219,100.0);(447.09219,100.0);(447.09219,100.0);(447.09219,100.0);(447.09219,100.0);(447.09219,100.0);(447.09219,100.0);(447.09219,100.0);(447.09219,100.0);(447.09219,100.0);(447.09219,100.0)
Predicted LC-MS/MS	Not Available	Positive	medium	View Spectrum	(59.01276,6.55);(61.02841,5.7);(129.01824,9.02);(131.03389,10.34);(131.03389,10.34);(157.01315,13.01);(157.01315,13.01);(157.01315,13.01);(159.0288,9.57);(159.0288,9.57);(177.03936,9.66);(177.03936,9.66);(177.03936,9.66);(177.03936,9.66);(177.03936,9.66);(271.0601,100.0);(271.0601,100.0);(271.0601,100.0);(271.0601,100.0);(271.0601,100.0);(271.0601,100.0);(271.0601,100.0);(271.0601,100.0);(311.05501,12.36);(313.07066,49.07);(315.08631,25.46);(315.08631,25.46);(315.08631,25.46);(315.08631,25.46);(329.06558,11.81);(331.08123,6.71);(343.08123,6.97);(343.08123,6.97);(343.08123,6.97);(359.07614,7.02);(359.07614,7.02);(369.06049,7.02);(371.07614,26.32);(373.09179,12.09);(401.08671,28.45);(401.08671,28.45);(401.08671,28.45);(401.08671,28.45);(401.08671,28.45);(401.08671,28.45);(401.08671,28.45);(401.08671,28.45);(401.08671,28.45);(401.08671,28.45);(403.10236,5.72);(403.10236,5.72);(411.07106,23.04);(411.07106,23.04);(411.07106,23.04);(429.08162,73.22);(429.08162,73.22);(429.08162,73.22);(429.08162,73.22);(429.08162,73.22);(429.08162,73.22);(429.08162,73.22);(429.08162,73.22);(429.08162,73.22);(429.08162,73.22);(429.08162,73.22);(429.08162,73.22);(429.08162,73.22);(429.08162,73.22);(429.08162,73.22);(429.08162,73.22);(429.08162,73.22);(447.09219,48.43);(447.09219,48.43);(447.09219,48.43);(447.09219,48.43);(447.09219,48.43);(447.09219,48.43);(447.09219,48.43);(447.09219,48.43);(447.09219,48.43);(447.09219,48.43);(447.09219,48.43);(447.09219,48.43);(447.09219,48.43);(447.09219,48.43);(447.09219,48.43);(447.09219,48.43);(447.09219,48.43);(447.09219,48.43);(447.09219,48.43);(447.09219,48.43)
Predicted LC-MS/MS	Not Available	Positive	high	View Spectrum	(59.01276,19.27);(61.02841,27.93);(63.04406,7.08);(73.02841,8.2);(73.02841,8.2);(73.02841,8.2);(101.02332,7.33);(101.02332,7.33);(101.02332,7.33);(103.03897,8.74);(103.03897,8.74);(103.03897,8.74);(129.01824,16.58);(133.02841,8.65);(153.01824,12.55);(157.01315,6.45);(157.01315,6.45);(157.01315,6.45);(229.04954,9.48);(229.04954,9.48);(229.04954,9.48);(241.04954,10.33);(241.04954,10.33);(241.04954,10.33);(241.04954,10.33);(241.04954,10.33);(243.06519,13.01);(243.06519,13.01);(243.06519,13.01);(243.06519,13.01);(255.06519,14.42);(255.06519,14.42);(255.06519,14.42);(255.06519,14.42);(255.06519,14.42);(255.06519,14.42);(255.06519,14.42);(255.06519,14.42);(271.0601,100.0);(271.0601,100.0);(271.0601,100.0);(271.0601,100.0);(271.0601,100.0);(271.0601,100.0);(271.0601,100.0);(271.0601,100.0);(281.06558,6.25);(283.0601,33.75);(283.0601,33.75);(283.0601,33.75);(283.0601,33.75);(283.0601,33.75);(283.0601,33.75);(283.0601,33.75);(295.0601,11.62);(299.05501,7.42);(299.05501,7.42);(339.04993,8.6);(343.08123,11.9);(343.08123,11.9);(343.08123,11.9);(345.09688,15.97);(357.06049,7.19);(357.06049,7.19);(359.07614,9.96);(359.07614,9.96);(371.07614,10.82);(377.08671,8.68);(401.08671,10.99);(401.08671,10.99);(401.08671,10.99);(401.08671,10.99);(401.08671,10.99);(401.08671,10.99);(401.08671,10.99);(401.08671,10.99);(401.08671,10.99);(401.08671,10.99);(421.07654,5.87);(429.08162,16.79);(429.08162,16.79);(429.08162,16.79);(429.08162,16.79);(429.08162,16.79);(429.08162,16.79);(429.08162,16.79);(429.08162,16.79);(429.08162,16.79);(429.08162,16.79);(429.08162,16.79);(429.08162,16.79);(429.08162,16.79);(429.08162,16.79);(429.08162,16.79);(429.08162,16.79);(429.08162,16.79);(447.09219,9.17);(447.09219,9.17);(447.09219,9.17);(447.09219,9.17);(447.09219,9.17);(447.09219,9.17);(447.09219,9.17);(447.09219,9.17);(447.09219,9.17);(447.09219,9.17);(447.09219,9.17);(447.09219,9.17);(447.09219,9.17);(447.09219,9.17);(447.09219,9.17);(447.09219,9.17);(447.09219,9.17);(447.09219,9.17);(447.09219,9.17);(447.09219,9.17)
Predicted LC-MS/MS	Not Available	Negative	low	View Spectrum	(75.00877,4.12);(129.01933,12.39);(157.01425,16.47);(157.01425,16.47);(157.01425,16.47);(175.02481,16.6);(175.02481,16.6);(175.02481,16.6);(175.02481,16.6);(175.02481,16.6);(175.02481,16.6);(175.02481,16.6);(269.04555,40.93);(269.04555,40.93);(269.04555,40.93);(269.04555,40.93);(269.04555,40.93);(269.04555,40.93);(269.04555,40.93);(297.04046,7.51);(327.05103,9.66);(327.05103,9.66);(409.05651,14.2);(409.05651,14.2);(409.05651,14.2);(409.05651,14.2);(427.06707,89.1);(427.06707,89.1);(427.06707,89.1);(427.06707,89.1);(427.06707,89.1);(427.06707,89.1);(427.06707,89.1);(427.06707,89.1);(427.06707,89.1);(427.06707,89.1);(427.06707,89.1);(427.06707,89.1);(427.06707,89.1);(427.06707,89.1);(427.06707,89.1);(427.06707,89.1);(427.06707,89.1);(427.06707,89.1);(427.06707,89.1);(427.06707,89.1);(427.06707,89.1);(427.06707,89.1);(427.06707,89.1);(445.07763,100.0);(445.07763,100.0);(445.07763,100.0);(445.07763,100.0);(445.07763,100.0);(445.07763,100.0);(445.07763,100.0);(445.07763,100.0);(445.07763,100.0);(445.07763,100.0);(445.07763,100.0);(445.07763,100.0);(445.07763,100.0);(445.07763,100.0);(445.07763,100.0);(445.07763,100.0);(445.07763,100.0);(445.07763,100.0);(445.07763,100.0);(445.07763,100.0)
Predicted LC-MS/MS	Not Available	Negative	medium	View Spectrum	(41.00329,7.81);(59.01385,30.77);(59.01385,30.77);(72.99312,8.83);(73.0295,4.56);(73.0295,4.56);(75.00877,12.36);(87.00877,6.87);(87.00877,6.87);(87.00877,6.87);(89.02442,7.42);(89.02442,7.42);(125.02442,5.22);(125.02442,5.22);(131.03498,5.35);(147.0299,6.47);(163.02481,5.35);(175.02481,7.32);(175.02481,7.32);(175.02481,7.32);(175.02481,7.32);(175.02481,7.32);(175.02481,7.32);(175.02481,7.32);(269.04555,100.0);(269.04555,100.0);(269.04555,100.0);(269.04555,100.0);(269.04555,100.0);(269.04555,100.0);(269.04555,100.0);(271.0612,4.71);(271.0612,4.71);(297.04046,8.98);(299.05611,4.51);(327.05103,12.72);(327.05103,12.72);(341.06668,8.73);(343.08233,4.1);(371.07724,4.69);(371.07724,4.69);(375.07216,16.57);(383.07724,8.13);(383.07724,8.13);(385.05651,6.81);(385.05651,6.81);(385.05651,6.81);(387.07216,5.35);(387.07216,5.35);(399.07216,5.21);(399.07216,5.21);(399.07216,5.21);(399.07216,5.21);(401.08781,7.54);(401.08781,7.54);(401.08781,7.54);(401.08781,7.54);(401.08781,7.54);(417.08272,9.98);(417.08272,9.98);(417.08272,9.98);(417.08272,9.98);(417.08272,9.98);(417.08272,9.98);(417.08272,9.98);(417.08272,9.98);(417.08272,9.98);(417.08272,9.98);(417.08272,9.98);(417.08272,9.98);(427.06707,18.23);(427.06707,18.23);(427.06707,18.23);(427.06707,18.23);(427.06707,18.23);(427.06707,18.23);(427.06707,18.23);(427.06707,18.23);(427.06707,18.23);(427.06707,18.23);(427.06707,18.23);(427.06707,18.23);(427.06707,18.23);(427.06707,18.23);(427.06707,18.23);(427.06707,18.23);(427.06707,18.23);(427.06707,18.23);(427.06707,18.23);(427.06707,18.23);(427.06707,18.23);(427.06707,18.23);(427.06707,18.23);(443.06198,4.46);(443.06198,4.46);(445.07763,19.62);(445.07763,19.62);(445.07763,19.62);(445.07763,19.62);(445.07763,19.62);(445.07763,19.62);(445.07763,19.62);(445.07763,19.62);(445.07763,19.62);(445.07763,19.62);(445.07763,19.62);(445.07763,19.62);(445.07763,19.62);(445.07763,19.62);(445.07763,19.62);(445.07763,19.62);(445.07763,19.62);(445.07763,19.62);(445.07763,19.62);(445.07763,19.62)
Predicted LC-MS/MS	Not Available	Negative	high	View Spectrum	(41.00329,38.53);(56.9982,7.2);(59.01385,15.85);(59.01385,15.85);(83.01385,5.5);(87.00877,4.38);(87.00877,4.38);(87.00877,4.38);(109.0295,4.43);(109.0295,4.43);(109.0295,4.43);(125.02442,6.51);(125.02442,6.51);(133.0295,4.96);(201.01933,10.9);(201.05572,13.06);(211.04007,5.71);(215.03498,8.36);(227.03498,94.84);(227.03498,94.84);(227.03498,94.84);(239.03498,7.1);(241.05063,10.02);(241.05063,10.02);(241.05063,10.02);(269.04555,100.0);(269.04555,100.0);(269.04555,100.0);(269.04555,100.0);(269.04555,100.0);(269.04555,100.0);(269.04555,100.0);(375.07216,6.15);(417.08272,4.44);(417.08272,4.44);(417.08272,4.44);(417.08272,4.44);(417.08272,4.44);(417.08272,4.44);(417.08272,4.44);(417.08272,4.44);(417.08272,4.44);(417.08272,4.44);(417.08272,4.44);(417.08272,4.44);(419.06198,4.78);(427.06707,5.7);(427.06707,5.7);(427.06707,5.7);(427.06707,5.7);(427.06707,5.7);(427.06707,5.7);(427.06707,5.7);(427.06707,5.7);(427.06707,5.7);(427.06707,5.7);(427.06707,5.7);(427.06707,5.7);(427.06707,5.7);(427.06707,5.7);(427.06707,5.7);(427.06707,5.7);(427.06707,5.7);(427.06707,5.7);(427.06707,5.7);(427.06707,5.7);(427.06707,5.7);(427.06707,5.7);(427.06707,5.7)

Food Sources

No food source information available

Food Sources of its Food Phytochemical(s)

	Food Phytochemical	Food Source	Food Source Group
	Genistein	Chickpea	Pulses and beans		Show
	Genistein	Red clover	Pulses and beans	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
	Genistin		Genistein 4'-O-glucuronide	human	plasma	host metabolism	Not Available	Not Available	Not Available	C₂₁H₁₈O₁₁	446.0849114		Publications
	Genistein		Genistein 4'-O-glucuronide	human	plasma	host metabolism	3h-5h	<20 nmol/L	Not Available	C₂₁H₁₈O₁₁	446.0849114		Publications

Inter-Individual Variations in Metabolism

	Food Phytochemical		Metabolite	Effect	Value

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Showing entry for Genistein 4'-O-glucuronide