PhytoHub: Showing entry for Avenanthramide 2f

Avenanthramide 2f

Identification

PhytoHub ID

PHUB000570

Name

Avenanthramide 2f

Systematic Name

Not Available

Synonyms

Avenanthramide A1
Avenanthramide B
N-[4'-Hydroxy-3'-methoxy-(E)-cinnamoyl]-5-hydroxyanthranilic acid

CAS Number

Not Available

Average Mass

329.308

Monoisotopic Mass

329.089937207

Chemical Formula

C₁₇H₁₅NO₆

IUPAC Name

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

InChI Key

JXFZHMCSCYADIX-XVNBXDOJSA-N

InChI Identifier

InChI=1S/C17H15NO6/c1-24-15-8-10(2-6-14(15)20)3-7-16(21)18-13-5-4-11(19)9-12(13)17(22)23/h2-9,19-20H,1H3,(H,18,21)(H,22,23)/b7-3+

SMILES

COC1=C(O)C=CC(\C=C\C(=O)NC2=CC=C(O)C=C2C(O)=O)=C1

Structure

Similar Structures

Calculated Properties

Solubility (ALOGPS): 2.40e-02 g/l
LogS (ALOGPS): -4.14
LogP (ALOGPS): 2.89
Hydrogen Acceptors: 6
Hydrogen Donors: 4
Rotatable Bond Count: 5
Polar Surface Area: 116.09000000000002
Refractivity: 89.01839999999999
Polarizability: 33.118066162714555
Formal Charge: 0
Physiological Charge: -1
pKa (strongest basic): -2.031672753251153
pKa (strongest acidic): 3.3071193313077383
Number of Rings: 2
Rule of Five: Yes
Bioavailability: Yes
Ghose Filter: Yes
Veber's Rule: No
MDDR-like Rule: No

External Links

PubChem: 10087955
Chemistry Dashboard: DTXSID50148603
Phenol-Explorer: 534
PeakForestCompound: 000438

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 2f	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", "Alkyl aryl ethers", "Anilides", "Anisoles", "Benzoic acids", "Benzoyl derivatives", "Carbonyl compounds", "Carboxylic acids", "Hydrocarbon derivatives", "Hydroxybenzoic acid derivatives", "Methoxybenzenes", "Methoxyphenols", "Monocarboxylic acids and derivatives", "N-arylamides", "N-cinnamoylanthranilic acids", "Organic oxides", "Organopnictogen compounds", "Phenoxy compounds", "Secondary carboxylic acid amides", "Styrenes", "Vinylogous amides"]
External Descriptor Annotations: Not Available
Substituent Names: ["1-hydroxy-2-unsubstituted benzenoid", "Acylaminobenzoic acid or derivatives", "Alkyl aryl ether", "Anilide", "Anisole", "Aromatic homomonocyclic compound", "Avenanthramide", "Benzenoid", "Benzoic acid", "Benzoic acid or derivatives", "Benzoyl", "Carbonyl group", "Carboxamide group", "Carboxylic acid", "Carboxylic acid derivative", "Cinnamic acid amide", "Ether", "Hydrocarbon derivative", "Hydroxybenzoic acid", "Methoxybenzene", "Methoxyphenol", "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", "Phenol ether", "Phenoxy compound", "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	(108.0443863,1.060704009);(109.0522109,1.142529819);(135.0314758,1.21424653);(136.0393004,1.519010678);(136.0518764,1.139127264);(138.0311413,0.823811987);(147.0440518,1.318662568);(148.0518764,1.114542054);(149.059701,2.813229601);(150.0675256,1.339743038);(151.0263899,1.208502308);(152.0342145,1.820180051);(153.0420391,4.040068979);(154.0498637,1.625916209);(155.0576883,1.006396579);(177.0546151,3.456910073);(180.0291286,1.021373399);(281.0682516,0.9932738368);(282.0760762,0.9901664001);(283.0839008,1.481351923);(284.0917254,1.285770927);(285.09955,1.873067265);(298.0709903,0.9964499856);(299.0788149,1.15282556);(300.0866395,1.423722526);(301.0944641,0.9288855364);(311.0788149,3.014101155);(312.0866395,2.972490797);(313.0580798,0.763757645);(314.0659044,2.472899769);(329.0893782,2.06544632)
Predicted GC-MS	GC-MS	Positive	Not Available	View Spectrum	(73.04679982,3.497547625);(208.0788242,3.559098947);(209.0809483,0.6018437723);(221.0992248,1.001728387);(249.0941389,4.259858527);(250.0965768,0.8512487797);(282.0976129,7.611049288);(283.0993371,1.852508049);(284.0967411,0.7583973129);(295.1054375,0.6151043703);(296.1132621,1.27624452);(297.1210867,0.8012383054);(298.1289113,0.7685788196);(428.170773,0.5962748855);(429.1785976,0.6639682842);(444.1656871,0.8932038899);(455.1578625,0.6682309126);(456.1656871,3.003330008);(457.1679795,1.107568972);(471.1527766,0.6649168038);(472.1606012,2.595034324);(473.1628956,0.9579704511);(473.1684258,2.651914202);(474.1707218,0.9793658016);(474.1762504,1.361455017);(528.2052109,0.8828738031);(529.1766512,1.008731678);(530.1844758,13.12657078);(531.1865203,5.81608772);(532.1850972,2.701705198);(533.185935,0.751241586)
Predicted GC-MS	GC-MS	Ei	Not Available	View Spectrum	(108.0443863,1.060704009);(109.0522109,1.142529819);(135.0314758,1.21424653);(136.0393004,1.519010678);(136.0518764,1.139127264);(138.0311413,0.823811987);(147.0440518,1.318662568);(148.0518764,1.114542054);(149.059701,2.813229601);(150.0675256,1.339743038);(151.0263899,1.208502308);(152.0342145,1.820180051);(153.0420391,4.040068979);(154.0498637,1.625916209);(155.0576883,1.006396579);(177.0546151,3.456910073);(180.0291286,1.021373399);(281.0682516,0.9932738368);(282.0760762,0.9901664001);(283.0839008,1.481351923);(284.0917254,1.285770927);(285.09955,1.873067265);(298.0709903,0.9964499856);(299.0788149,1.15282556);(300.0866395,1.423722526);(301.0944641,0.9288855364);(311.0788149,3.014101155);(312.0866395,2.972490797);(313.0580798,0.763757645);(314.0659044,2.472899769);(329.0893782,2.06544632)
LC-MS/MS	Not Available	positive	Not Available	View Spectrum	(89.039452,0.592654);(106.039726,0.328413);(117.033417,8.297158);(118.036957,1.238156);(121.065834,0.41901);(134.035263,1.253256);(136.032639,0.547356);(145.028046,37.02012);(146.031784,4.141029);(147.037628,0.592654);(149.059464,8.08199);(150.060898,1.090937);(177.054459,100.0);(178.057098,10.758371);(179.06076,0.947492)
LC-MS/MS	Not Available	positive	Not Available	View Spectrum	(117.032967,0.726941);(134.034393,0.281279);(145.027328,11.013699);(146.031754,0.876712);(149.059555,0.584475);(150.063156,0.452968);(176.98735,0.281279);(177.054489,100.0);(178.056839,12.094977);(179.058792,1.198174);(216.025711,0.230137);(323.094055,0.526027);(330.095886,11.484932);(331.098938,2.874886);(332.101532,0.339726);(504.129364,0.489498);(1429.969238,0.23379)
Predicted LC-MS/MS	Not Available	Positive	low	View Spectrum	(108.0449388,1.067415559);(125.0602545,0.4054280164);(136.0398534,2.79134493);(137.0602545,0.5142600031);(138.0555035,0.3264452775);(149.0602545,3.221086608);(151.0759046,0.2740790631);(152.0347681,31.2619543);(154.0504181,4.307963408);(156.0660682,0.1862904413);(160.0398534,0.2256789443);(161.0602545,0.1686665834);(175.0395191,0.5459596578);(177.0551691,0.9327199973);(179.0708192,0.3741662641);(180.0296827,0.7755314683);(188.0347681,0.1890099054);(194.0453327,0.5805650469);(204.0296827,0.2433434376);(206.0453327,0.6600870127);(258.0766329,0.3694333488);(266.0817182,0.5952108277);(282.0766329,0.6806202);(284.0922829,7.809119848);(286.107933,0.717490978);(294.0766329,0.7480536158);(294.0766329,0.1921005237);(298.0715475,0.6647833514);(300.0871975,0.6439847547);(312.0871975,12.86962353);(330.0977622,25.6575831)
Predicted LC-MS/MS	Not Available	Positive	med	View Spectrum	(108.0449388,9.02786086);(119.0496898,0.7659178579);(136.0398534,5.724197663);(137.0602545,0.9304136334);(138.0555035,0.409184348);(145.0289544,0.9941783876);(149.0602545,6.604972565);(151.0759046,0.4659452163);(152.0347681,40.40363927);(154.0504181,1.946553029);(160.0398534,0.576427468);(161.0602545,0.5846652526);(175.0395191,0.8559746324);(177.0551691,7.396697216);(179.0708192,0.7268262464);(180.0296827,0.8343191148);(204.0296827,0.3891598643);(206.0453327,0.5638059038);(252.0660682,0.4635722642);(254.0817182,0.8211164425);(266.0817182,0.6560899119);(268.0973683,0.39086683);(280.0609828,0.3794173921);(282.0766329,0.8161474255);(284.0922829,4.841565131);(286.107933,1.714313705);(294.0766329,0.7885835709);(298.0715475,0.6353261876);(300.0871975,0.9307659318);(312.0871975,5.131079674);(330.0977622,3.230417001)
Predicted LC-MS/MS	Not Available	Positive	high	View Spectrum	(51.0234751,2.26810993);(52.01872406,1.294868307);(54.03437413,2.04778423);(55.01838972,1.253449614);(77.03912516,2.3123496);(80.01363868,9.152704323);(82.02928875,3.547637708);(98.02420337,0.5891584928);(99.00821896,0.5156671583);(101.023869,1.138233667);(107.0496898,2.213542459);(108.0449388,12.63989334);(119.0496898,3.702731813);(123.008219,1.237547262);(124.0034679,1.097502459);(125.023869,1.132786013);(126.019118,1.518723192);(133.0289544,2.92485296);(135.0446045,1.392187762);(136.0398534,4.322276471);(137.0602545,2.663685791);(149.0602545,8.709296332);(152.0347681,24.49561518);(154.0504181,0.505881494);(160.0398534,1.47498709);(161.0602545,1.092466453);(175.0395191,0.7729439053);(180.0296827,0.5690207757);(228.0296827,0.7248642966);(254.0817182,1.476758907);(266.0817182,1.212473018)
Predicted LC-MS/MS	Not Available	Negative	low	View Spectrum	(55.01838972,0.1641062978);(93.03403978,0.3474850179);(106.0292887,1.684802695);(134.0242034,1.006213116);(135.0446045,0.5939067882);(136.0398534,0.1926239208);(148.0398534,0.1648273624);(149.0602545,0.8187768826);(150.019118,0.4247505879);(152.0347681,2.579855738);(154.0504181,0.1888467839);(175.0395191,0.4995878287);(177.0551691,5.564438106);(178.0140326,0.5147974825);(180.0296827,0.3115696418);(192.0296827,0.2501755273);(230.0817182,0.1950663748);(252.0660682,0.2454236188);(254.0817182,0.2675706284);(264.0660682,0.2089560034);(266.0817182,7.126311813);(268.0609828,3.099789413);(280.0609828,0.1525717712);(282.0766329,0.7054746155);(284.0922829,32.00090698);(296.0558974,0.1955967305);(298.0715475,0.2718700725);(302.0664621,0.1631451319);(310.0715475,4.772962133);(312.050812,0.4712104525);(328.0821122,34.81638048)
Predicted LC-MS/MS	Not Available	Negative	med	View Spectrum	(106.0292887,8.34222904);(133.0289544,0.6898539311);(134.0242034,2.882878238);(135.0446045,1.555712336);(136.0398534,0.8321712401);(147.0446045,0.4000705675);(148.0398534,1.353855406);(149.0602545,1.417157543);(150.019118,0.9007192255);(152.0347681,3.708293685);(159.0446045,0.4188844799);(175.0395191,4.589641902);(177.0551691,4.450198737);(178.0140326,1.044192182);(190.0504181,0.3820492223);(192.0296827,0.7806764563);(228.0660682,0.6845878725);(242.0817182,0.8780066175);(252.0660682,1.71001916);(254.0817182,1.809751595);(266.0817182,9.566074989);(268.0609828,13.33435351);(280.0609828,0.4046679309);(282.0766329,1.314069072);(284.0558974,0.383565533);(284.0922829,22.95527678);(286.0715475,0.5268017114);(296.0558974,0.398892305);(310.0715475,3.125962453);(312.050812,1.827238858);(328.0821122,7.332147418)
Predicted LC-MS/MS	Not Available	Negative	high	View Spectrum	(41.00273965,3.310357754);(41.99798862,2.410767819);(55.01838972,0.8548911936);(80.01363868,0.8716094);(93.03403978,0.8717359261);(105.0340398,1.087928065);(106.0292887,29.20268092);(110.0242034,1.027124109);(117.0340398,0.8586780572);(122.0242034,1.623805667);(133.0289544,3.419216137);(134.0242034,7.715220492);(135.0446045,2.109724179);(136.0398534,1.711304908);(147.0446045,1.739863492);(148.0398534,3.3827252);(149.0602545,0.8532265629);(150.019118,8.272835622);(152.0347681,8.280554433);(161.023869,2.702607534);(175.0395191,2.506908079);(177.0551691,2.591155596);(178.0140326,1.437502861);(192.0296827,0.8209194723);(192.0660682,1.071339619);(242.0817182,1.030173683);(252.0660682,0.7902358625);(254.0817182,1.013395153);(266.0817182,1.742526928);(268.0609828,3.860388252);(284.0922829,0.8285970255)
Predicted LC-MS/MS	Not Available	Negative	low	View Spectrum	(175.04007,11.88);(175.04007,11.88);(175.04007,11.88);(175.04007,11.88);(268.06153,23.53);(268.06153,23.53);(284.09283,26.04);(284.09283,26.04);(284.09283,26.04);(284.09283,26.04);(284.09283,26.04);(284.09283,26.04);(284.09283,26.04);(284.09283,26.04);(310.0721,4.62);(310.0721,4.62);(310.0721,4.62);(310.0721,4.62);(310.0721,4.62);(312.05136,7.35);(312.05136,7.35);(312.05136,7.35);(312.05136,7.35);(312.05136,7.35);(312.05136,7.35);(312.05136,7.35);(328.08266,100.0);(328.08266,100.0);(328.08266,100.0);(328.08266,100.0);(328.08266,100.0);(328.08266,100.0);(328.08266,100.0);(328.08266,100.0);(328.08266,100.0);(328.08266,100.0)
Predicted LC-MS/MS	Not Available	Negative	medium	View Spectrum	(106.02984,3.9);(108.04549,20.82);(133.0295,16.93);(134.02475,33.5);(135.04515,5.32);(135.04515,5.32);(136.0404,11.96);(148.0404,7.78);(149.0608,7.41);(149.0608,7.41);(149.0608,7.41);(161.02442,6.38);(175.04007,5.03);(175.04007,5.03);(175.04007,5.03);(175.04007,5.03);(178.01458,6.03);(178.01458,6.03);(178.01458,6.03);(178.01458,6.03);(252.06662,6.01);(252.06662,6.01);(254.08227,8.77);(254.08227,8.77);(254.08227,8.77);(256.09792,10.02);(256.09792,10.02);(266.04588,5.15);(266.08227,10.93);(266.08227,10.93);(268.06153,100.0);(268.06153,100.0);(274.0721,5.45);(274.0721,5.45);(274.0721,5.45);(282.07718,11.35);(282.07718,11.35);(282.07718,11.35);(282.07718,11.35);(282.07718,11.35);(284.09283,10.4);(284.09283,10.4);(284.09283,10.4);(284.09283,10.4);(284.09283,10.4);(284.09283,10.4);(284.09283,10.4);(284.09283,10.4);(286.0721,3.86);(286.0721,3.86);(286.0721,3.86);(286.0721,3.86);(286.0721,3.86);(310.0721,7.35);(310.0721,7.35);(310.0721,7.35);(310.0721,7.35);(310.0721,7.35);(326.06701,26.83);(326.06701,26.83);(326.06701,26.83);(326.06701,26.83);(326.06701,26.83);(326.06701,26.83)
Predicted LC-MS/MS	Not Available	Negative	high	View Spectrum	(41.99854,8.5);(93.03459,7.53);(105.03459,8.02);(106.02984,7.64);(108.04549,11.87);(119.05024,16.5);(119.05024,16.5);(121.06589,16.2);(133.0295,62.82);(134.02475,42.34);(135.04515,30.03);(135.04515,30.03);(136.0404,10.42);(149.0608,20.6);(149.0608,20.6);(149.0608,20.6);(164.03532,8.48);(164.03532,8.48);(178.01458,30.35);(178.01458,30.35);(178.01458,30.35);(178.01458,30.35);(210.05605,17.73);(212.0717,22.32);(232.06153,23.3);(240.06662,14.86);(240.06662,14.86);(240.06662,14.86);(240.06662,14.86);(252.03023,8.38);(252.03023,8.38);(252.03023,8.38);(254.04588,22.45);(254.04588,22.45);(254.04588,22.45);(254.04588,22.45);(254.08227,31.5);(254.08227,31.5);(254.08227,31.5);(256.06153,37.88);(256.06153,37.88);(256.06153,37.88);(256.06153,37.88);(256.06153,37.88);(256.06153,37.88);(256.09792,12.66);(256.09792,12.66);(258.07718,13.02);(258.07718,13.02);(258.07718,13.02);(266.04588,7.24);(268.06153,15.93);(268.06153,15.93);(274.0721,16.75);(274.0721,16.75);(274.0721,16.75);(282.0408,14.91);(282.0408,14.91);(282.0408,14.91);(284.05645,12.32);(284.05645,12.32);(284.05645,12.32);(284.05645,12.32);(284.05645,12.32);(326.06701,100.0);(326.06701,100.0);(326.06701,100.0);(326.06701,100.0);(326.06701,100.0);(326.06701,100.0)
Predicted LC-MS/MS	Not Available	Positive	low	View Spectrum	(145.02841,16.25);(147.04406,10.41);(147.04406,10.41);(147.04406,10.41);(149.05971,17.01);(149.05971,17.01);(149.05971,17.01);(149.05971,17.01);(177.05462,100.0);(177.05462,100.0);(177.05462,100.0);(177.05462,100.0);(177.05462,100.0);(177.05462,100.0);(177.05462,100.0);(280.06043,27.69);(280.06043,27.69);(284.09173,16.67);(284.09173,16.67);(284.09173,16.67);(284.09173,16.67);(284.09173,16.67);(284.09173,16.67);(284.09173,16.67);(284.09173,16.67);(312.08665,62.42);(312.08665,62.42);(312.08665,62.42);(312.08665,62.42);(312.08665,62.42);(312.08665,62.42);(312.08665,62.42);(312.08665,62.42);(312.08665,62.42);(312.08665,62.42);(312.08665,62.42);(312.08665,62.42);(312.08665,62.42);(330.09721,31.68);(330.09721,31.68);(330.09721,31.68);(330.09721,31.68);(330.09721,31.68);(330.09721,31.68);(330.09721,31.68);(330.09721,31.68);(330.09721,31.68);(330.09721,31.68);(330.09721,31.68);(330.09721,31.68);(330.09721,31.68)
Predicted LC-MS/MS	Not Available	Positive	medium	View Spectrum	(117.03349,13.26);(135.04406,8.82);(135.04406,8.82);(135.04406,8.82);(135.04406,8.82);(145.02841,43.38);(147.04406,52.64);(147.04406,52.64);(147.04406,52.64);(149.05971,33.94);(149.05971,33.94);(149.05971,33.94);(149.05971,33.94);(164.03422,16.81);(166.04987,14.07);(177.05462,38.28);(177.05462,38.28);(177.05462,38.28);(177.05462,38.28);(177.05462,38.28);(177.05462,38.28);(177.05462,38.28);(252.06552,7.18);(254.08117,7.56);(280.06043,100.0);(280.06043,100.0);(282.07608,16.22);(282.07608,16.22);(284.09173,26.14);(284.09173,26.14);(284.09173,26.14);(284.09173,26.14);(284.09173,26.14);(284.09173,26.14);(284.09173,26.14);(284.09173,26.14);(312.08665,34.51);(312.08665,34.51);(312.08665,34.51);(312.08665,34.51);(312.08665,34.51);(312.08665,34.51);(312.08665,34.51);(312.08665,34.51);(312.08665,34.51);(312.08665,34.51);(312.08665,34.51);(312.08665,34.51);(312.08665,34.51)
Predicted LC-MS/MS	Not Available	Positive	high	View Spectrum	(77.03858,24.44);(79.05423,14.77);(105.03349,22.18);(105.03349,22.18);(107.04914,9.09);(108.04439,100.0);(109.06479,22.72);(109.06479,22.72);(110.06004,7.3);(117.03349,11.87);(121.06479,21.12);(121.06479,21.12);(133.02841,11.06);(135.04406,27.39);(135.04406,27.39);(135.04406,27.39);(135.04406,27.39);(136.0393,28.73);(136.0393,28.73);(137.05971,7.51);(137.05971,7.51);(138.05495,7.0);(138.05495,7.0);(145.02841,16.51);(147.04406,28.49);(147.04406,28.49);(147.04406,28.49);(149.05971,36.04);(149.05971,36.04);(149.05971,36.04);(149.05971,36.04);(151.07536,12.43);(151.07536,12.43);(151.07536,12.43);(151.07536,12.43);(151.07536,12.43);(151.07536,12.43);(151.07536,12.43);(154.04987,12.3);(154.04987,12.3);(159.04406,6.3);(159.04406,6.3);(177.05462,24.89);(177.05462,24.89);(177.05462,24.89);(177.05462,24.89);(177.05462,24.89);(177.05462,24.89);(177.05462,24.89);(214.08626,6.06);(228.06552,9.11);(230.08117,14.0);(234.11247,9.11);(268.06043,6.75);(268.06043,6.75);(268.06043,6.75);(268.09682,8.45);(268.09682,8.45);(268.09682,8.45);(286.071,6.28);(286.071,6.28);(286.10738,6.86);(286.10738,6.86);(286.10738,6.86);(286.10738,6.86);(286.10738,6.86);(328.08156,9.41)

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 2f		Avenanthramide 2f	human	plasma	unchanged	<1h	20-50 nmol/L	Not Available	C₁₇H₁₅NO₆	329.089937207		Publications
	Avenanthramide 2f		dihydroavenanthramide 2f	human	urine	gut microbiota metabolite	Not Available	Not Available	<1%				Publications

Inter-Individual Variations in Metabolism

	Food Phytochemical		Metabolite	Effect	Value

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Showing entry for Avenanthramide 2f