PhytoHub: Showing entry for Chrysophanol

Chrysophanol

Identification

PhytoHub ID

PHUB002552

Name

Chrysophanol

Systematic Name

1,8-Dihydroxy-3-methylanthraquinone

Synonyms

1,8-dihydroxy-3-methyl-9,10-anthracenedione
3-methylchrysazin
Chrysophanic acid
chrysophanol

CAS Number

481-74-3

Average Mass

254.241

Monoisotopic Mass

254.057908802

Chemical Formula

C₁₅H₁₀O₄

IUPAC Name

1,8-dihydroxy-3-methyl-9,10-dihydroanthracene-9,10-dione

InChI Key

LQGUBLBATBMXHT-UHFFFAOYSA-N

InChI Identifier

InChI=1S/C15H10O4/c1-7-5-9-13(11(17)6-7)15(19)12-8(14(9)18)3-2-4-10(12)16/h2-6,16-17H,1H3

SMILES

 	Cc1cc(O)c2C(=O)c3c(O)cccc3C(=O)c2c1

Structure

Similar Structures

Calculated Properties

Solubility (ALOGPS): 1.25e-01 g/l
LogS (ALOGPS): -3.31
LogP (ALOGPS): 3.08
Hydrogen Acceptors: 4
Hydrogen Donors: 2
Rotatable Bond Count: 0
Polar Surface Area: 74.6
Refractivity: 70.15400000000001
Polarizability: 25.514998563874897
Formal Charge: 0
Physiological Charge: 0
pKa (strongest basic): -5.64676034239525
pKa (strongest acidic): 7.940475575263968
Number of Rings: 3
Rule of Five: Yes
Bioavailability: Yes
Ghose Filter: Yes
Veber's Rule: No
MDDR-like Rule: No

External Links

PubChem: 10208
ChEBI: 3687
FooDB (Compounds): FDB002584
HMDB: HMDB0030670

Taxonomy as Food Phytochemical

Family: Miscellaneous phytochemicals
Class: Miscellaneous phytochemicals
Sub-class: Not Available

Classyfire Taxonomy

Kingdom Name: Organic compounds
Class: Anthracenes
Super-class: Benzenoids
Sub-class: Anthraquinones
Direct Parent Name: Anthraquinones
Alternative Parent Names: ["1-hydroxy-2-unsubstituted benzenoids", "1-hydroxy-4-unsubstituted benzenoids", "Aryl ketones", "Hydrocarbon derivatives", "Organic oxides", "Vinylogous acids"]
External Descriptor Annotations: ["Anthracenes and phenanthrenes", "Anthraquinone type", "a hydroxyanthraquinone", "hydroxyanthraquinones"]
Substituent Names: ["1-hydroxy-2-unsubstituted benzenoid", "1-hydroxy-4-unsubstituted benzenoid", "9,10-anthraquinone", "Anthraquinone", "Aromatic homopolycyclic compound", "Aryl ketone", "Hydrocarbon derivative", "Ketone", "Organic oxide", "Organic oxygen compound", "Organooxygen compound", "Vinylogous acid"]

Spectra from Phytohub

Spectrum Type	Instrument Type	Ion Mode	Collision Energy Level	View	Peaks

Predicted GC-MS	GC-MS	Positive	Not Available	View Spectrum	(39.02292522,1.299874827);(106.0413131,2.736204516);(107.0491377,1.145942807);(120.020578,1.840583807);(121.0284026,0.8350484151);(132.020578,3.967905655);(133.0284026,1.202353135);(134.0362272,7.457061728);(135.0440518,2.711638171);(145.9998429,1.171525995);(147.0076675,0.8563898369);(160.0154921,1.148056459);(161.0233167,0.8392242445);(186.0311413,0.9730206959);(188.0467905,0.7921047536);(198.0675256,1.954438796);(210.0311413,3.59567926);(211.0389659,1.327204093);(212.0467905,2.110787545);(213.0546151,1.34047861);(224.0467905,1.200819279);(225.0546151,0.7058372341);(226.0624397,13.21922967);(227.0658287,2.106348999);(236.0467905,1.95874815);(237.0546151,1.461268271);(238.0260554,1.541164349);(239.03388,2.108141451);(253.0495292,2.785236835);(254.0573538,6.504180238);(255.0607424,1.111620267)
Predicted GC-MS	GC-MS	Positive	Not Available	View Spectrum	(39.02292522,1.82926041);(73.04679982,5.361777126);(113.0417139,0.9246646559);(115.0573631,1.042723843);(139.0573631,1.18800906);(149.0417139,1.125629988);(163.0573631,1.114948846);(189.036628,1.227067528);(191.0522772,1.956379239);(192.0601018,0.9784695408);(205.0679264,1.504389532);(206.075751,1.265029218);(207.0835756,2.27145545);(267.0471913,1.19683358);(281.0628405,1.090918018);(282.0706651,1.334334664);(283.0784897,1.170207507);(284.0863143,0.9422082288);(285.0941389,1.388867769);(297.0941389,2.264520426);(311.0734038,2.346278808);(325.089053,2.241024193);(326.0968776,1.763847223);(327.1047022,1.565903701);(355.1180135,2.827122187);(356.1201995,0.9005181762);(370.1414873,1.99108921);(382.105103,1.222171558);(383.1129276,5.028141508);(384.1151556,1.659774591);(398.1364014,0.9855467402)
Predicted GC-MS	GC-MS	Ei	Not Available	View Spectrum	(39.02292522,1.299874827);(106.0413131,2.736204516);(107.0491377,1.145942807);(120.020578,1.840583807);(121.0284026,0.8350484151);(132.020578,3.967905655);(133.0284026,1.202353135);(134.0362272,7.457061728);(135.0440518,2.711638171);(145.9998429,1.171525995);(147.0076675,0.8563898369);(160.0154921,1.148056459);(161.0233167,0.8392242445);(186.0311413,0.9730206959);(188.0467905,0.7921047536);(198.0675256,1.954438796);(210.0311413,3.59567926);(211.0389659,1.327204093);(212.0467905,2.110787545);(213.0546151,1.34047861);(224.0467905,1.200819279);(225.0546151,0.7058372341);(226.0624397,13.21922967);(227.0658287,2.106348999);(236.0467905,1.95874815);(237.0546151,1.461268271);(238.0260554,1.541164349);(239.03388,2.108141451);(253.0495292,2.785236835);(254.0573538,6.504180238);(255.0607424,1.111620267)
LC-MS/MS	LC-ESI-QTOF	negative	Not Available	View Spectrum	(104.4922,0.837776);(155.6661,1.142422);(169.8251,0.799695);(193.0859,0.837776);(209.0651,0.913938);(225.0544,5.21706);(231.1354,0.952018);(237.9116,0.875857);(253.0506,100.0)
LC-MS/MS	LC-ESI-QTOF	negative	Not Available	View Spectrum	(100.8506,4.276316);(120.7015,3.947368);(138.749,2.412281);(171.0236,2.412281);(171.0949,2.850877);(174.9374,5.701754);(203.1635,3.179825);(225.0553,23.464912);(236.0465,2.741228);(253.0515,100.0)
LC-MS/MS	LC-ESI-QTOF	negative	Not Available	View Spectrum	(154.0348,7.476636);(155.0525,7.71028);(180.0554,7.242991);(180.2998,14.485981);(181.0642,26.635514);(181.5387,6.074766);(182.0351,8.411215);(195.0429,5.373832);(196.0496,5.373832);(196.083,6.775701);(207.0495,7.943925);(210.0298,27.803738);(224.0482,27.336449);(225.0566,100.0);(225.0871,9.345794)
LC-MS/MS	LC-ESI-QTOF	positive	Not Available	View Spectrum	(176.9872,100.0);(177.0115,1.17713);(177.0308,4.652466);(177.0686,1.289238)
LC-MS/MS	LC-ESI-QTOF	positive	Not Available	View Spectrum	(173.0782,8.333333);(176.9876,100.0)
LC-MS/MS	Not Available	Negative	Not Available	View Spectrum	(100.8506,4.28);(120.7015,3.95);(138.749,2.41);(171.0236,2.41);(171.0949,2.85);(174.9374,5.7);(203.1635,3.18);(225.0553,23.46);(236.0465,2.74);(253.0515,100.0)
LC-MS/MS	Not Available	Negative	Not Available	View Spectrum	(154.0348,7.48);(155.0525,7.71);(180.0554,7.24);(180.2998,14.49);(181.0642,26.64);(181.5387,6.07);(182.0351,8.41);(195.0429,5.37);(196.0496,5.37);(196.083,6.78);(207.0495,7.94);(210.0298,27.8);(224.0482,27.34);(225.0566,100.0);(225.0871,9.35)
LC-MS/MS	Not Available	Negative	Not Available	View Spectrum	(155.6661,1.14);(225.0544,5.22);(253.0506,100.0)
LC-MS/MS	Not Available	Positive	Not Available	View Spectrum	(176.9872,100.0);(177.0115,1.18);(177.0308,4.65);(177.0686,1.29)
LC-MS/MS	Not Available	Positive	Not Available	View Spectrum	(173.0782,8.33);(176.9876,100.0)
LC-MS/MS	LC-ESI-QTOF	Negative	low	View Spectrum	(104.4922,0.00800801);(155.6661,0.01101101);(169.8251,0.00800801);(193.0859,0.00800801);(209.0651,0.00900901);(225.0544,0.05205205);(231.1354,0.01001001);(237.9116,0.00900901);(253.0506,1.0)
LC-MS/MS	LC-ESI-QTOF	Negative	high	View Spectrum	(154.0348,0.07507508);(155.0525,0.07707708);(180.0554,0.07207207);(180.2998,0.14514515);(181.0642,0.26626627);(181.5387,0.06106106);(182.0351,0.08408408);(195.0429,0.05405405);(196.0496,0.05405405);(196.083,0.06806807);(207.0495,0.07907908);(210.0298,0.27827828);(224.0482,0.27327327);(225.0566,1.0);(225.0871,0.09309309)
LC-MS/MS	LC-ESI-QTOF	Negative	medium	View Spectrum	(100.8506,0.04304304);(120.7015,0.03903904);(138.749,0.02402402);(171.0236,0.02402402);(171.0949,0.02802803);(174.9374,0.05705706);(203.1635,0.03203203);(225.0553,0.23423423);(236.0465,0.02702703);(253.0515,1.0)
LC-MS/MS	LC-ESI-QTOF	Negative	low	View Spectrum	(155.666,0.011);(225.054,0.052);(231.135,0.01);(253.051,1.0)
LC-MS/MS	LC-ESI-QTOF	Negative	medium	View Spectrum	(100.851,0.043);(120.702,0.039);(138.749,0.024);(171.024,0.024);(171.095,0.029);(174.937,0.057);(203.164,0.032);(225.055,0.235);(236.046,0.027);(253.052,1.0)
LC-MS/MS	LC-ESI-QTOF	Negative	high	View Spectrum	(154.035,0.075);(155.052,0.077);(180.055,0.072);(180.3,0.145);(181.064,0.266);(181.539,0.061);(182.035,0.084);(195.043,0.054);(196.05,0.054);(196.083,0.068);(207.05,0.079);(210.03,0.278);(224.048,0.273);(225.057,1.0);(225.087,0.093)
Predicted LC-MS/MS	Not Available	Positive	low	View Spectrum	(41.03912516,0.0468628144);(43.01838972,0.0297168228);(51.0234751,0.0007520372);(65.03912516,0.0011539646);(67.01838972,0.0318353469);(69.03403978,0.0000060628);(79.01838972,0.000073176);(81.03403978,0.0000538562);(91.01838972,0.0007269083);(95.01330434,0.000066928);(104.9976543,0.000009326);(107.0133043,0.0001298389);(107.0496898,1.69933773);(123.0446045,0.0000006801);(149.023869,0.209387415);(159.0446045,0.0000341873);(163.0395191,0.0000647303);(171.0446045,0.0002486023);(183.0446045,0.0000818472);(189.0551691,0.0113406832);(197.023869,0.000059223);(199.0395191,0.0000489256);(213.0551691,0.1847470694);(215.0344337,0.0198731219);(229.0500838,0.054560079);(239.0344337,0.099245158);(255.0657338,97.60958347)
Predicted LC-MS/MS	Not Available	Positive	med	View Spectrum	(41.03912516,0.9629602564);(43.01838972,0.075456532);(51.0234751,0.0459840954);(65.03912516,0.0833494974);(67.01838972,0.5990680941);(69.03403978,0.0013352857);(79.01838972,0.0049208536);(81.03403978,0.0057750311);(91.01838972,0.0875575415);(95.01330434,0.0015729384);(104.9976543,0.0005031444);(107.0133043,0.0190265061);(107.0496898,7.048208304);(123.0446045,0.0194874761);(149.023869,1.869199016);(159.0446045,0.0325086035);(163.0395191,0.0074897835);(171.0446045,0.0255835004);(183.0446045,0.0447367696);(189.0551691,0.2027131265);(197.023869,0.0031911187);(199.0395191,0.0123985474);(213.0551691,3.189022577);(215.0344337,0.1503647884);(229.0500838,0.4261036392);(239.0344337,0.349972097);(255.0657338,84.73151088)
Predicted LC-MS/MS	Not Available	Positive	high	View Spectrum	(41.03912516,1.686467515);(43.01838972,2.555731812);(51.0234751,1.974571307);(65.03912516,8.395675064);(67.01838972,7.797922014);(69.03403978,0.1193422793);(79.01838972,0.910340806);(81.03403978,0.9128815558);(91.01838972,3.359938277);(95.01330434,0.1763984808);(104.9976543,0.322083488);(107.0133043,1.345229242);(107.0496898,33.05874029);(123.0446045,0.0329305147);(149.023869,6.294757939);(159.0446045,0.5130461694);(163.0395191,0.1918927638);(171.0446045,1.536395357);(183.0446045,1.005226888);(189.0551691,0.5594545626);(197.023869,0.6045466226);(199.0395191,0.287498912);(213.0551691,7.758445336);(215.0344337,0.2472438146);(229.0500838,0.7478858907);(239.0344337,2.245313609);(255.0657338,15.36003949)
Predicted LC-MS/MS	Not Available	Negative	low	View Spectrum	(39.0234751,0.0240660721);(41.00273965,0.0431127707);(49.00782503,0.0008454846);(63.0234751,0.0010290535);(65.00273965,0.0104003227);(67.01838972,0.000007047);(77.00273965,0.0000758625);(79.01838972,0.0000526966);(89.00273965,0.0000363323);(92.99765427,0.0000150581);(104.9976543,0.000063648);(105.0340398,0.9044137294);(145.0289544,0.0000337006);(147.008219,0.0676671827);(159.0446045,0.0000535268);(169.0289544,0.0000192476);(171.008219,0.0000179492);(173.023869,0.000071628);(181.0289544,0.000032866);(187.0395191,0.0306665398);(197.023869,0.0000107871);(211.0395191,0.3457449233);(213.0187836,0.0355775676);(227.0344337,0.0565517999);(237.0187836,0.0158364333);(253.0500838,98.46359777)
Predicted LC-MS/MS	Not Available	Negative	med	View Spectrum	(39.0234751,0.1248479088);(41.00273965,0.1413961371);(49.00782503,0.0096157432);(63.0234751,0.0140615776);(65.00273965,0.0214492647);(67.01838972,0.0000233325);(77.00273965,0.0012193893);(79.01838972,0.0007166175);(89.00273965,0.0008144073);(92.99765427,0.0011833505);(104.9976543,0.0011226183);(105.0340398,2.913569354);(145.0289544,0.0064130172);(147.008219,0.210442548);(159.0446045,0.0106220683);(169.0289544,0.00290201);(171.008219,0.0000529231);(173.023869,0.0050164409);(181.0289544,0.0002989877);(187.0395191,0.0724380158);(197.023869,0.0000597382);(211.0395191,1.701403289);(213.0187836,0.1089771375);(227.0344337,0.1852562101);(237.0187836,0.1051485785);(253.0500838,94.36094934)
Predicted LC-MS/MS	Not Available	Negative	high	View Spectrum	(39.0234751,1.58777922);(41.00273965,14.67824514);(49.00782503,0.2503128139);(63.0234751,0.6380757745);(65.00273965,1.667530132);(67.01838972,0.1212599188);(77.00273965,0.4661156555);(79.01838972,1.021324396);(89.00273965,0.1343872072);(92.99765427,0.3675390388);(104.9976543,1.647041508);(105.0340398,28.60835616);(145.0289544,1.037375708);(147.008219,9.168134802);(159.0446045,1.052802046);(169.0289544,0.3477034313);(171.008219,0.1190168924);(173.023869,0.0655938902);(181.0289544,0.1758787771);(187.0395191,1.405343548);(197.023869,0.1534926332);(211.0395191,3.642885226);(213.0187836,2.027042307);(227.0344337,2.046136645);(237.0187836,0.4277731405);(253.0500838,27.14285399)
Predicted LC-MS/MS	Not Available	Positive	low	View Spectrum	(255.06519,100.0);(255.06519,100.0);(255.06519,100.0);(255.06519,100.0);(255.06519,100.0);(255.06519,100.0);(255.06519,100.0);(255.06519,100.0);(255.06519,100.0);(255.06519,100.0);(255.06519,100.0);(255.06519,100.0);(255.06519,100.0);(255.06519,100.0);(255.06519,100.0)
Predicted LC-MS/MS	Not Available	Positive	medium	View Spectrum	(121.02841,5.61);(121.02841,5.61);(121.02841,5.61);(121.02841,5.61);(121.02841,5.61);(121.02841,5.61);(121.02841,5.61);(121.02841,5.61);(121.02841,5.61);(121.02841,5.61);(255.06519,100.0);(255.06519,100.0);(255.06519,100.0);(255.06519,100.0);(255.06519,100.0);(255.06519,100.0);(255.06519,100.0);(255.06519,100.0);(255.06519,100.0);(255.06519,100.0);(255.06519,100.0);(255.06519,100.0);(255.06519,100.0);(255.06519,100.0);(255.06519,100.0)
Predicted LC-MS/MS	Not Available	Positive	high	View Spectrum	(65.03858,9.26);(65.03858,9.26);(91.05423,8.91);(93.03349,13.3);(93.03349,13.3);(93.03349,13.3);(93.03349,13.3);(107.04914,68.24);(107.04914,68.24);(107.04914,68.24);(107.04914,68.24);(107.04914,68.24);(107.04914,68.24);(121.02841,23.09);(121.02841,23.09);(121.02841,23.09);(121.02841,23.09);(121.02841,23.09);(121.02841,23.09);(121.02841,23.09);(121.02841,23.09);(121.02841,23.09);(121.02841,23.09);(133.02841,26.9);(135.04406,100.0);(135.04406,100.0);(135.04406,100.0);(135.04406,100.0);(187.03897,42.64);(187.03897,42.64);(187.03897,42.64);(187.03897,42.64);(187.03897,42.64);(201.05462,10.58);(211.03897,11.13);(211.03897,11.13);(211.03897,11.13);(213.05462,16.06);(213.05462,16.06);(215.03389,13.76);(215.03389,13.76);(215.03389,13.76);(215.03389,13.76);(227.07027,28.21);(227.07027,28.21);(227.07027,28.21);(227.07027,28.21);(227.07027,28.21);(227.07027,28.21);(227.07027,28.21);(227.07027,28.21);(227.07027,28.21);(227.07027,28.21);(237.05462,22.93);(237.05462,22.93);(237.05462,22.93);(237.05462,22.93);(237.05462,22.93);(237.05462,22.93);(237.05462,22.93);(237.05462,22.93);(237.05462,22.93);(237.05462,22.93);(237.05462,22.93);(237.05462,22.93);(237.05462,22.93);(237.05462,22.93);(253.04954,8.97);(253.04954,8.97);(253.04954,8.97);(255.06519,7.44);(255.06519,7.44);(255.06519,7.44);(255.06519,7.44);(255.06519,7.44);(255.06519,7.44);(255.06519,7.44);(255.06519,7.44);(255.06519,7.44);(255.06519,7.44);(255.06519,7.44);(255.06519,7.44);(255.06519,7.44);(255.06519,7.44);(255.06519,7.44)
Predicted LC-MS/MS	Not Available	Negative	low	View Spectrum	(253.05063,100.0);(253.05063,100.0);(253.05063,100.0);(253.05063,100.0);(253.05063,100.0);(253.05063,100.0);(253.05063,100.0);(253.05063,100.0)
Predicted LC-MS/MS	Not Available	Negative	medium	View Spectrum	(253.05063,100.0);(253.05063,100.0);(253.05063,100.0);(253.05063,100.0);(253.05063,100.0);(253.05063,100.0);(253.05063,100.0);(253.05063,100.0)
Predicted LC-MS/MS	Not Available	Negative	high	View Spectrum	(91.01894,15.75);(107.05024,42.55);(107.05024,42.55);(107.05024,42.55);(107.05024,42.55);(107.05024,42.55);(119.01385,49.64);(119.01385,49.64);(119.01385,49.64);(119.01385,49.64);(183.04515,47.74);(183.04515,47.74);(211.04007,81.62);(211.04007,81.62);(211.04007,81.62);(211.04007,81.62);(211.04007,81.62);(211.04007,81.62);(211.04007,81.62);(211.04007,81.62);(225.05572,100.0);(225.05572,100.0);(225.05572,100.0);(225.05572,100.0);(225.05572,100.0);(253.05063,67.24);(253.05063,67.24);(253.05063,67.24);(253.05063,67.24);(253.05063,67.24);(253.05063,67.24);(253.05063,67.24);(253.05063,67.24)

Food Sources

	Name	Group
	Garden rhubarb	Vegetables, Other vegetables	Publications	Show
	rhubarb	Vegetables, Other vegetables	Publications	Show

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

No metabolism information available

Inter-Individual Variations in Metabolism

No data on inter-individual variations available

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Showing entry for Chrysophanol