PhytoHub: Showing entry for Avenanthramide 2p

Avenanthramide 2p

Identification

PhytoHub ID

PHUB000571

Name

Avenanthramide 2p

Systematic Name

Not Available

Synonyms

Avenanthramide A
Avenanthramide A4
N-[4'-Hydroxy-(E)cinnamoyl]-5-hydroxyanthranilic acid

CAS Number

Not Available

Average Mass

299.282

Monoisotopic Mass

299.079372523

Chemical Formula

C₁₆H₁₃NO₅

IUPAC Name

5-hydroxy-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enamido]benzoic acid

InChI Key

QGUMNWHANDITDB-FPYGCLRLSA-N

InChI Identifier

InChI=1S/C16H13NO5/c18-11-4-1-10(2-5-11)3-8-15(20)17-14-7-6-12(19)9-13(14)16(21)22/h1-9,18-19H,(H,17,20)(H,21,22)/b8-3+

SMILES

OC(=O)C1=CC(O)=CC=C1NC(=O)\C=C\C1=CC=C(O)C=C1

Structure

Similar Structures

Calculated Properties

Solubility (ALOGPS): 4.50e-02 g/l
LogS (ALOGPS): -3.82
LogP (ALOGPS): 2.96
Hydrogen Acceptors: 5
Hydrogen Donors: 4
Rotatable Bond Count: 4
Polar Surface Area: 106.86
Refractivity: 82.55519999999999
Polarizability: 30.331988140296573
Formal Charge: 0
Physiological Charge: -1
pKa (strongest basic): -2.0315529503969465
pKa (strongest acidic): 3.3071191264897113
Number of Rings: 2
Rule of Five: Yes
Bioavailability: Yes
Ghose Filter: Yes
Veber's Rule: No
MDDR-like Rule: No

External Links

ChEBI: 2939
PubChem: 5281157
KNApSAcK: C00001527
Phenol-Explorer: 532
PeakForestCompound: 000439

Taxonomy as Food Phytochemical

Family: N-containing compounds
Class: Alkaloids
Sub-class: Miscellaneous alkaloids

Taxonomy as Metabolite

Metabolite Family: N-containing compound metabolites
Metabolite Class: Alkaloid metabolites
Metabolite Sub-class: Aventhramides

Taxonomy of its Food Phytochemical Precursor(s)

Food Phytochemical	Family	Class	Sub-class
Avenanthramide 2p	N-containing compounds	Alkaloids	Miscellaneous alkaloids	Show Food Phytochemical

Classyfire Taxonomy

Kingdom Name: Organic compounds
Class: Cinnamic acids and derivatives
Super-class: Phenylpropanoids and polyketides
Sub-class: Hydroxycinnamic acids and derivatives
Direct Parent Name: Avenanthramides
Alternative Parent Names: ["1-hydroxy-2-unsubstituted benzenoids", "Acylaminobenzoic acid and derivatives", "Anilides", "Benzoic acids", "Benzoyl derivatives", "Carbonyl compounds", "Carboxylic acids", "Coumaric acids and derivatives", "Hydrocarbon derivatives", "Hydroxybenzoic acid derivatives", "Monocarboxylic acids and derivatives", "N-arylamides", "N-cinnamoylanthranilic acids", "Organic oxides", "Organopnictogen compounds", "Secondary carboxylic acid amides", "Styrenes", "Vinylogous amides"]
External Descriptor Annotations: ["hydroxycinnamic acid"]
Substituent Names: ["1-hydroxy-2-unsubstituted benzenoid", "Acylaminobenzoic acid or derivatives", "Anilide", "Aromatic homomonocyclic compound", "Avenanthramide", "Benzenoid", "Benzoic acid", "Benzoic acid or derivatives", "Benzoyl", "Carbonyl group", "Carboxamide group", "Carboxylic acid", "Carboxylic acid derivative", "Cinnamic acid amide", "Coumaric acid or derivatives", "Hydrocarbon derivative", "Hydroxybenzoic acid", "Monocarboxylic acid or derivatives", "Monocyclic benzene moiety", "N-arylamide", "N-cinnamoylanthranilic acid", "Organic nitrogen compound", "Organic oxide", "Organic oxygen compound", "Organonitrogen compound", "Organooxygen compound", "Organopnictogen compound", "Phenol", "Secondary carboxylic acid amide", "Styrene", "Vinylogous amide"]

Spectra from Phytohub

Spectrum Type	Instrument Type	Ion Mode	Collision Energy Level	View	Peaks

Predicted GC-MS	GC-MS	Positive	Not Available	View Spectrum	(77.00219012,1.340156988);(107.0365617,1.782291995);(118.0413131,2.551345747);(119.0491377,4.916195895);(120.0569623,1.765009569);(134.0236512,3.063604726);(136.0393004,3.129892287);(147.0440518,4.869154587);(148.0518764,3.224703448);(149.059701,3.463421179);(151.0263899,5.027186375);(152.0342145,9.662000892);(153.0420391,5.502874706);(154.0498637,1.701705188);(229.0369532,1.529558138);(242.0447778,2.012995647);(251.0576883,2.016479445);(252.0655129,1.711148723);(253.0733375,3.1742626);(254.0811621,2.035216544);(255.0526024,1.377646081);(255.0889867,5.59034);(268.060427,1.949004599);(269.0682516,1.887983809);(270.0760762,4.797113306);(271.0839008,1.919787108);(281.0682516,7.510261207);(282.0715149,1.396375319);(282.0760762,5.490540714);(298.0709903,1.341582954);(299.0788149,2.260160225)
Predicted GC-MS	GC-MS	Positive	Not Available	View Spectrum	(71.03115062,0.8273758903);(72.03897522,0.7135671947);(73.04679982,6.707454703);(74.05462442,0.6634454593);(75.06244902,0.6478575922);(89.04171392,1.345565752);(191.0886615,1.142190788);(219.0835756,7.884442448);(220.0859492,1.481971064);(282.0976129,0.9423420584);(296.1132621,0.9769718958);(297.1210867,0.9320539705);(324.1081762,0.6386728479);(399.1680343,0.6507163912);(414.1551238,1.333283379);(425.1472992,0.8475773301);(426.1551238,6.756251523);(427.1573775,2.411383496);(428.1558826,0.912974187);(441.1422133,0.7025696145);(442.1500379,2.600339473);(443.1522937,0.9290657959);(443.1578625,2.700760294);(444.16012,0.965349959);(444.1656871,1.417791611);(498.1946476,0.8654750077);(499.1660879,0.7210881421);(500.1739125,11.46719341);(501.1759182,4.944752429);(502.1743716,2.277992462);(503.1751829,0.6188383486)
Predicted GC-MS	GC-MS	Ei	Not Available	View Spectrum	(104.0256639,0.9585095824);(105.0334885,1.201809206);(106.0413131,1.32207766);(109.0522109,1.001079607);(117.0334885,1.905434145);(118.0413131,1.217235299);(119.0491377,4.597223871);(120.0569623,1.578266761);(135.0314758,0.9522795289);(136.0393004,1.619433412);(138.0311413,0.9445583944);(145.0284026,0.8953528904);(147.0440518,2.664771014);(151.0263899,0.9277100169);(152.0342145,1.550159977);(153.0420391,3.538631991);(154.0498637,1.045269394);(180.0291286,1.347100666);(242.0447778,1.011165651);(251.0576883,1.118469724);(252.0655129,1.114970084);(253.0733375,1.668065378);(254.0811621,1.989352708);(255.0889867,2.238014103);(268.060427,0.9850326861);(270.0760762,2.060001891);(281.0682516,3.276353899);(282.0760762,3.485409606);(297.0631657,1.162610625);(298.0709903,1.398765687);(299.0788149,2.51684681)
LC-MS/MS	LC-ESI-qToF	Positive	Not Available	View Spectrum	(91.055908,412.0);(119.049248,10244.0);(120.051834,1212.0);(136.037735,676.0);(137.042297,440.0);(147.044128,63776.0);(148.047256,6148.0);(149.053467,624.0);(180.986176,316.0);(239.236359,456.0);(257.248749,1104.0);(258.248535,356.0);(282.075195,364.0)
LC-MS/MS	Not Available	positive	Not Available	View Spectrum	(91.055908,0.646011);(119.049248,16.062469);(120.051834,1.900401);(136.037735,1.05996);(137.042297,0.689915);(147.044128,100.0);(148.047256,9.63999);(149.053467,0.978424);(180.986176,0.495484);(239.236359,0.715003);(257.248749,1.731059);(258.248535,0.558204);(282.075195,0.570748)
LC-MS/MS	Not Available	positive	Not Available	View Spectrum	(79.020737,0.443707);(87.253189,0.573572);(89.414894,0.959561);(91.054367,32.585405);(101.060509,0.790015);(105.025002,0.533891);(109.064217,0.624076);(118.032677,0.660149);(119.00338,0.959561);(119.025398,1.305869);(119.049332,48.428989);(119.085922,0.811659);(120.051414,4.487573);(121.038483,0.49421);(129.044998,0.580787);(136.038513,1.5656);(145.839966,0.667364);(146.508057,0.328271);(146.907166,0.501425);(147.043777,100.0);(147.093918,0.389596);(147.118118,0.544713);(148.047104,2.640597);(149.133011,1.287832);(150.966553,0.642112);(158.080322,0.580787);(160.215164,0.295805);(175.039688,0.588002);(190.02475,0.479781);(202.092621,0.382382);(206.020599,0.580787);(207.028458,0.728689);(208.038574,1.832546);(223.062729,3.120378);(236.072296,0.811659);(247.166748,1.363587);(301.067474,1.13993);(1346.167847,0.652935);(1614.40686,1.356372)
Predicted LC-MS/MS	Not Available	Positive	low	View Spectrum	(95.04968984,0.4285913553);(107.0496898,0.5184266339);(108.0449388,1.079427492);(119.0496898,3.272933229);(121.0653399,0.292169071);(131.0496898,0.1665989079);(136.0398534,2.811808379);(138.0555035,0.3300638207);(145.0289544,0.5469649971);(147.0446045,0.9451226994);(149.0602545,0.3679077731);(152.0347681,31.0906941);(154.0504181,4.312733714);(156.0660682,0.1864461159);(160.0398534,0.2266506254);(180.0296827,0.7760748665);(188.0347681,0.1899500136);(194.0453327,0.58113527);(204.0296827,0.2435824594);(206.0453327,0.6612353042);(228.0660682,0.3704099066);(236.0711536,0.7371670527);(252.0660682,0.6032299081);(254.0817182,7.88079694);(256.0973683,0.7473813248);(264.0660682,1.049867422);(268.0609828,0.1954882476);(270.0766329,0.3848118575);(282.0766329,0.7214632416);(282.0766329,12.49957591);(300.0871975,25.78129136)
Predicted LC-MS/MS	Not Available	Positive	med	View Spectrum	(95.04968984,0.3803170433);(107.0496898,1.011471903);(108.0449388,9.295647563);(119.0496898,7.334797785);(121.0653399,0.6458757114);(131.0496898,0.5560317258);(136.0398534,5.924072089);(138.0555035,0.4291996681);(145.0289544,0.8649589159);(147.0446045,8.66090859);(149.0602545,0.6597576071);(152.0347681,39.6183659);(154.0504181,1.946153511);(160.0398534,0.5975010818);(180.0296827,0.831855809);(188.0347681,0.3450234007);(204.0296827,0.3882109165);(206.0453327,0.5647924791);(224.0711536,0.2128077103);(236.0711536,0.8935233853);(238.0868036,0.4208126542);(252.0660682,0.4162927882);(254.0453327,0.2176050138);(254.0817182,5.110543813);(256.0973683,1.914065109);(258.0766329,0.4016174323);(264.0660682,1.283373561);(270.0766329,0.4487049682);(282.0766329,0.3251589696);(282.0766329,5.032413425);(300.0871975,3.268139465)
Predicted LC-MS/MS	Not Available	Positive	high	View Spectrum	(51.0234751,1.450264681);(52.01872406,1.335224512);(54.03437413,2.111606011);(55.01838972,1.292514954);(65.03912516,0.9627700831);(77.03912516,3.832532821);(79.01838972,0.8588674082);(80.01363868,9.437959909);(82.02928875,3.658204316);(89.03912516,4.658217289);(91.05477522,0.8796354837);(98.02420337,0.6075203611);(101.023869,1.173708157);(103.0547752,0.6481547805);(107.0496898,3.111892185);(108.0449388,13.09108076);(119.0496898,11.30281351);(121.0653399,0.7326271507);(123.008219,1.276116985);(124.0034679,1.131707509);(124.0398534,0.6441620017);(125.023869,1.168090719);(126.019118,1.566056117);(131.0496898,0.7446341786);(136.0398534,4.492971623);(145.0289544,0.800738714);(147.0446045,0.5898311538);(152.0347681,21.96680343);(160.0398534,1.526486604);(224.0711536,1.329460621);(236.0711536,1.617345972)
Predicted LC-MS/MS	Not Available	Negative	low	View Spectrum	(93.03403978,0.1217676941);(105.0340398,0.6020853019);(106.0292887,1.802517096);(117.0340398,0.121026485);(119.0496898,0.9054381565);(129.0340398,0.1423614443);(134.0242034,1.081524496);(136.0398534,0.2075360791);(137.023869,0.1434945328);(143.0133043,0.0867914461);(145.0289544,0.5102541513);(147.0446045,5.680919466);(148.0398534,0.1784678458);(150.019118,0.4221626542);(152.0347681,2.559808412);(154.0504181,0.1885195724);(178.0140326,0.5122523115);(180.0296827,0.3101737121);(192.0296827,0.2497745758);(198.0555035,0.1361480437);(200.0711536,0.1945731588);(234.0555035,0.2127387901);(236.0711536,8.404210277);(250.0504181,0.1335255984);(252.0660682,0.7038178739);(254.0817182,34.13667034);(268.0609828,0.1598513569);(272.0558974,0.2034923847);(280.0609828,0.6674183581);(280.0609828,4.308307039);(298.0715475,34.91237135)
Predicted LC-MS/MS	Not Available	Negative	med	View Spectrum	(93.03403978,0.274392269);(105.0340398,1.763649646);(106.0292887,10.47231354);(117.0340398,0.4501748416);(119.0496898,2.338702719);(129.0340398,0.4895232522);(134.0242034,3.445126304);(136.0398534,1.080151386);(145.0289544,5.603693758);(147.0446045,5.474190995);(148.0398534,1.699777717);(150.019118,0.8624357906);(152.0347681,3.540668683);(154.0504181,0.3444594472);(160.0398534,0.5310209397);(178.0140326,1.023063472);(180.0296827,0.2867702715);(192.0296827,0.8017764231);(212.0711536,0.6259117751);(224.0711536,0.4422977121);(234.0555035,0.3104701968);(236.0711536,14.7705288);(250.0504181,0.3351628678);(252.0660682,1.3391922);(254.0817182,29.64732599);(256.0609828,0.3548098791);(272.0558974,0.2464628813);(280.0609828,0.3916674049);(280.0609828,3.016276087);(282.0402474,0.2913826087);(298.0715475,7.74662015)
Predicted LC-MS/MS	Not Available	Negative	high	View Spectrum	(40.01872406,0.9253456715);(41.00273965,4.85724547);(41.99798862,2.65298654);(44.99765427,0.7318013567);(67.01838972,0.6137717144);(80.01363868,1.194784818);(93.03403978,2.079395447);(101.0391252,0.8448597524);(105.0340398,3.123871198);(106.0292887,32.03021968);(108.0449388,0.6615490793);(110.0242034,1.010819112);(115.0183897,0.4897812101);(117.0340398,2.580792798);(119.0496898,2.946266469);(122.0242034,1.676214367);(129.0340398,1.416884338);(134.0242034,8.321919519);(136.0398534,1.86272018);(145.0289544,4.994004287);(147.0446045,4.247621574);(148.0398534,3.845265064);(150.019118,4.985512968);(152.0347681,4.167339316);(160.0398534,0.5837016624);(162.0555035,1.07765006);(178.0140326,0.9287908755);(192.0296827,0.8758072832);(212.0711536,0.9027665227);(236.0711536,2.240552343);(254.0817182,1.129759319)
Predicted LC-MS/MS	Not Available	Positive	low	View Spectrum	(147.04406,100.0);(147.04406,100.0);(147.04406,100.0);(147.04406,100.0);(282.07608,39.37);(282.07608,39.37);(282.07608,39.37);(282.07608,39.37);(282.07608,39.37);(282.07608,39.37);(282.07608,39.37);(282.07608,39.37);(282.07608,39.37);(282.07608,39.37);(282.07608,39.37);(300.08665,23.14);(300.08665,23.14);(300.08665,23.14);(300.08665,23.14);(300.08665,23.14);(300.08665,23.14);(300.08665,23.14);(300.08665,23.14);(300.08665,23.14);(300.08665,23.14)
Predicted LC-MS/MS	Not Available	Positive	medium	View Spectrum	(119.04914,31.36);(119.04914,31.36);(119.04914,31.36);(119.04914,31.36);(129.03349,11.23);(129.03349,11.23);(136.0393,24.81);(136.0393,24.81);(145.02841,11.04);(145.02841,11.04);(145.02841,11.04);(145.02841,11.04);(147.04406,100.0);(147.04406,100.0);(147.04406,100.0);(147.04406,100.0);(164.03422,57.0);(282.07608,42.27);(282.07608,42.27);(282.07608,42.27);(282.07608,42.27);(282.07608,42.27);(282.07608,42.27);(282.07608,42.27);(282.07608,42.27);(282.07608,42.27);(282.07608,42.27);(282.07608,42.27)
Predicted LC-MS/MS	Not Available	Positive	high	View Spectrum	(77.03858,12.56);(79.05423,5.43);(79.05423,5.43);(91.01784,5.38);(91.05423,15.82);(101.03858,7.78);(103.05423,11.22);(105.03349,10.19);(105.03349,10.19);(107.04914,12.48);(107.04914,12.48);(108.04439,25.8);(117.03349,9.32);(117.03349,9.32);(119.04914,100.0);(119.04914,100.0);(119.04914,100.0);(119.04914,100.0);(121.06479,14.95);(121.06479,14.95);(121.06479,14.95);(121.06479,14.95);(129.03349,13.47);(129.03349,13.47);(131.04914,19.19);(131.04914,19.19);(136.0393,12.27);(136.0393,12.27);(145.02841,5.4);(145.02841,5.4);(145.02841,5.4);(145.02841,5.4);(147.04406,19.29);(147.04406,19.29);(147.04406,19.29);(147.04406,19.29);(154.04987,9.65);(154.04987,9.65);(202.08626,4.88);(226.08626,8.14);(226.08626,8.14);(232.06043,7.43);(232.06043,7.43);(238.08626,10.53);(238.08626,10.53);(238.08626,10.53);(242.04478,7.03);(242.04478,7.03);(242.04478,7.03);(244.06043,7.1);(244.06043,7.1);(246.07608,4.7);(246.07608,4.7);(258.07608,12.33);(258.07608,12.33);(258.07608,12.33)
Predicted LC-MS/MS	Not Available	Negative	low	View Spectrum	(108.04549,10.06);(119.05024,28.46);(119.05024,28.46);(119.05024,28.46);(119.05024,28.46);(236.0717,33.29);(236.0717,33.29);(236.0717,33.29);(254.08227,100.0);(254.08227,100.0);(254.08227,100.0);(254.08227,100.0);(254.08227,100.0);(254.08227,100.0);(254.08227,100.0);(298.0721,33.85);(298.0721,33.85);(298.0721,33.85);(298.0721,33.85);(298.0721,33.85);(298.0721,33.85);(298.0721,33.85);(298.0721,33.85);(298.0721,33.85);(298.0721,33.85)
Predicted LC-MS/MS	Not Available	Negative	medium	View Spectrum	(91.01894,4.05);(91.05532,5.35);(101.03967,9.69);(106.02984,8.17);(108.04549,24.57);(117.03459,5.58);(119.05024,100.0);(119.05024,100.0);(119.05024,100.0);(119.05024,100.0);(134.02475,41.18);(134.02475,41.18);(136.0404,6.42);(145.0295,14.43);(145.0295,14.43);(145.0295,14.43);(148.0404,4.94);(228.06662,4.19);(228.06662,4.19);(228.06662,4.19);(236.0717,25.5);(236.0717,25.5);(236.0717,25.5);(252.06662,4.19);(252.06662,4.19);(252.06662,4.19);(254.08227,27.78);(254.08227,27.78);(254.08227,27.78);(254.08227,27.78);(254.08227,27.78);(254.08227,27.78);(254.08227,27.78);(280.06153,9.23);(280.06153,9.23);(280.06153,9.23);(280.06153,9.23);(280.06153,9.23);(280.06153,9.23);(280.06153,9.23);(280.06153,9.23);(296.05645,9.65);(296.05645,9.65);(296.05645,9.65);(296.05645,9.65);(298.0721,8.72);(298.0721,8.72);(298.0721,8.72);(298.0721,8.72);(298.0721,8.72);(298.0721,8.72);(298.0721,8.72);(298.0721,8.72);(298.0721,8.72);(298.0721,8.72)
Predicted LC-MS/MS	Not Available	Negative	high	View Spectrum	(43.01894,4.0);(51.02402,9.83);(65.03967,13.58);(89.03967,6.53);(91.05532,7.99);(93.03459,23.04);(101.03967,22.84);(106.02984,12.3);(108.04549,22.48);(117.03459,49.82);(119.05024,100.0);(119.05024,100.0);(119.05024,100.0);(119.05024,100.0);(122.02475,4.79);(134.02475,17.85);(134.02475,17.85);(136.0404,4.28);(148.0404,4.12);(152.03532,6.54);(152.03532,6.54);(152.03532,6.54);(152.03532,6.54);(172.0404,6.7);(172.0404,6.7);(196.0404,3.71);(198.05605,5.01);(198.05605,5.01);(226.08735,3.84);(228.06662,4.51);(228.06662,4.51);(228.06662,4.51);(236.0717,7.89);(236.0717,7.89);(236.0717,7.89);(256.06153,4.44);(256.06153,4.44);(256.06153,4.44)

Food Sources

No food source information available

Food Sources of its Food Phytochemical(s)

No food source information available of its precursor(s)

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
	Avenanthramide 2p		Avenanthramide 2p	human	plasma, urine	unchanged	1h-3h	20-50 nmol/L	<1%	C₁₆H₁₃NO₅	299.079372523		Publications
	Avenanthramide 2p		dihydroavenanthramide 2p	human	urine	gut microbiota metabolite	Not Available	Not Available	<1%	C₁₆H₁₅NO₄	285.100107967		Publications

Inter-Individual Variations in Metabolism

	Food Phytochemical		Metabolite	Effect	Value

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Showing entry for Avenanthramide 2p