PhytoHub: Showing entry for Dihydrocaffeic acid-3-sulfate

Dihydrocaffeic acid-3-sulfate

Identification

PhytoHub ID

PHUB001588

Name

Dihydrocaffeic acid-3-sulfate

Systematic Name

3-(4'-hydroxyphenyl)propanoic acid-3'-sulfate

Synonyms

3-(4-hydroxyphenyl)propanoic acid-3-sulfate
3-(4-hydroxyphenyl)propionic acid-3-sulfate
3-(4-Hydroxyphenyl)propionic acid-3'-O-sulfate
dihydrocaffeic acid-3-sulfate

CAS Number

1187945-70-5

Average Mass

262.23

Monoisotopic Mass

262.014723836

Chemical Formula

C₉H₁₀O₇S

IUPAC Name

3-[4-hydroxy-3-(sulfooxy)phenyl]propanoic acid

InChI Key

MIMULQQHBAZGER-UHFFFAOYSA-N

InChI Identifier

InChI=1S/C9H10O7S/c10-7-3-1-6(2-4-9(11)12)5-8(7)16-17(13,14)15/h1,3,5,10H,2,4H2,(H,11,12)(H,13,14,15)

SMILES

OC(=O)CCC1=CC(OS(O)(=O)=O)=C(O)C=C1

Structure

Similar Structures

Calculated Properties

Solubility (ALOGPS): 2.15e+00 g/l
LogS (ALOGPS): -2.09
LogP (ALOGPS): -0.63
Hydrogen Acceptors: 6
Hydrogen Donors: 3
Rotatable Bond Count: 5
Polar Surface Area: 121.13000000000001
Refractivity: 55.92020000000001
Polarizability: 23.03018923639295
Formal Charge: 0
Physiological Charge: -2
pKa (strongest basic): -4.413439904857457
pKa (strongest acidic): -2.231573080921956
Number of Rings: 1
Rule of Five: Yes
Bioavailability: Yes
Ghose Filter: Yes
Veber's Rule: No
MDDR-like Rule: No

External Links

No external links

Taxonomy as Metabolite

Family: (Poly)phenol metabolites
Class: Phenolic acid metabolites
Sub-class: Phenylpropanoic acids

Taxonomy of its Food Phytochemical Precursor(s)

Food Phytochemical	Family	Class	Sub-class
Caffeic acid	Polyphenols	Phenolic acids	Hydroxycinnamic acids	Show Food Phytochemical
Orange flavanones	Polyphenols	Flavonoids	Flavanones	Show Food Phytochemical
Black tea Flavan-3-ols	Polyphenols	Flavonoids	Flavan-3-ols	Show Food Phytochemical
Coffee Chlorogenic acids	Polyphenols	Phenolic acids	Hydroxycinnamic acids	Show Food Phytochemical
Yerba mate Chlorogenic acids	Polyphenols	Phenolic acids	Hydroxycinnamic acids	Show Food Phytochemical
Coffee hydroxycinnamates	Polyphenols	Phenolic acids	Hydroxycinnamic acids	Show Food Phytochemical
Ferulic acid	Polyphenols	Phenolic acids	Hydroxycinnamic acids	Show Food Phytochemical

Classyfire Taxonomy

Kingdom Name: Organic compounds
Class: Organic sulfuric acids and derivatives
Super-class: Organic acids and derivatives
Sub-class: Arylsulfates
Direct Parent Name: Phenylsulfates
Alternative Parent Names: ["1-hydroxy-2-unsubstituted benzenoids", "Carbonyl compounds", "Carboxylic acids", "Hydrocarbon derivatives", "Monocarboxylic acids and derivatives", "Organic oxides", "Phenoxy compounds", "Phenylpropanoic acids", "Sulfuric acid monoesters"]
External Descriptor Annotations: Not Available
Substituent Names: ["1-hydroxy-2-unsubstituted benzenoid", "3-phenylpropanoic-acid", "Aromatic homomonocyclic compound", "Benzenoid", "Carbonyl group", "Carboxylic acid", "Carboxylic acid derivative", "Hydrocarbon derivative", "Monocarboxylic acid or derivatives", "Monocyclic benzene moiety", "Organic oxide", "Organic oxygen compound", "Organooxygen compound", "Phenol", "Phenoxy compound", "Phenylsulfate", "Sulfate-ester", "Sulfuric acid ester", "Sulfuric acid monoester"]

Spectra from Phytohub

Spectrum Type	Instrument Type	Ion Mode	Collision Energy Level	View	Peaks

Predicted GC-MS	GC-MS	Positive	Not Available	View Spectrum	(44.99710422,2.606915093);(59.01275342,1.177258135);(80.96408832,1.180968497);(109.0284026,1.907508183);(111.0440518,0.8121281365);(121.0284026,2.096788504);(123.0440518,2.157004936);(133.0284026,0.9819278935);(135.0440518,1.860953388);(136.0518764,1.046384744);(137.059701,1.565062278);(165.0546151,1.10282726);(176.0104062,0.8774230711);(178.0260554,1.178102701);(179.03388,1.157336482);(180.0417046,1.033215073);(181.0495292,2.229113853);(182.0573538,2.443555184);(188.9852149,1.239801146);(189.9930395,0.9930362759);(200.9852149,5.362673857);(201.9930395,1.297522244);(203.0008641,3.485300282);(215.0008641,2.130250977);(216.0086887,2.7191477);(217.0165133,4.699760079);(218.0243379,1.618120422);(244.0036028,2.403975226);(245.0114274,2.166288574);(259.9985169,0.8623066716);(262.0141661,2.56200515)
Predicted GC-MS	GC-MS	Positive	Not Available	View Spectrum	(59.03115062,0.9073910443);(71.03115062,0.9091309103);(73.04679982,10.18069614);(74.04796012,0.8711238521);(74.05462442,0.7317308468);(75.02606472,3.559311092);(75.06244902,0.7118739734);(89.04171392,3.374877188);(90.04953852,1.358011739);(91.05736312,1.178413248);(117.036628,1.264263899);(131.0522772,1.055557532);(273.0247387,0.953090665);(274.0325633,0.7288344944);(275.0403879,5.939303896);(276.0425124,1.036951268);(288.0482125,0.9236097836);(289.0560371,4.109642985);(290.0582423,0.7647443218);(305.0509512,1.333266682);(311.1129276,2.790951419);(312.1148676,0.7338347159);(317.0509512,3.223625966);(323.1129276,0.7660440605);(325.1285768,2.128482372);(326.1364014,1.004255724);(333.0458653,2.14844545);(334.0536899,2.22267467);(335.0615145,1.243711664);(391.0697399,3.980440808);(392.0716152,1.082486125)
Predicted GC-MS	GC-MS	Ei	Not Available	View Spectrum	(44.99710422,2.606915093);(59.01275342,1.177258135);(80.96408832,1.180968497);(109.0284026,1.907508183);(111.0440518,0.8121281365);(121.0284026,2.096788504);(123.0440518,2.157004936);(133.0284026,0.9819278935);(135.0440518,1.860953388);(136.0518764,1.046384744);(137.059701,1.565062278);(165.0546151,1.10282726);(176.0104062,0.8774230711);(178.0260554,1.178102701);(179.03388,1.157336482);(180.0417046,1.033215073);(181.0495292,2.229113853);(182.0573538,2.443555184);(188.9852149,1.239801146);(189.9930395,0.9930362759);(200.9852149,5.362673857);(201.9930395,1.297522244);(203.0008641,3.485300282);(215.0008641,2.130250977);(216.0086887,2.7191477);(217.0165133,4.699760079);(218.0243379,1.618120422);(244.0036028,2.403975226);(245.0114274,2.166288574);(259.9985169,0.8623066716);(262.0141661,2.56200515)
Predicted LC-MS/MS	Not Available	Positive	low	View Spectrum	(145.0284058,1.113638124);(165.0546206,1.388180392);(203.0008707,3.960190534);(217.0165208,6.177818476);(227.0008707,7.657487528);(245.0114354,43.25642275);(263.0220001,17.18974859)
Predicted LC-MS/MS	Not Available	Positive	med	View Spectrum	(55.01784114,0.7889508404);(59.01275576,1.143901852);(73.02840582,1.476102039);(80.96409131,2.921046015);(109.0284058,0.7283916059);(110.974656,0.9170503649);(119.0491413,0.8625965453);(121.0284058,1.185181987);(123.0440559,2.443940806);(135.0440559,1.815963152);(137.0597059,5.287428698);(165.0546206,11.36202286);(172.9903061,0.7398932031);(183.0651853,4.670666994);(184.9903061,1.365260331);(187.0059561,0.9053158306);(188.9852207,0.7562172381);(189.0216062,1.347380903);(199.0059561,2.128523071);(200.9852207,0.8792913976);(201.0216062,0.8107385128);(203.0008707,2.962166763);(215.0008707,1.746241613);(217.0165208,9.433061811);(227.0008707,5.546510576);(245.0114354,12.08657749);(263.0220001,3.963796158)
Predicted LC-MS/MS	Not Available	Positive	high	View Spectrum	(27.02292652,1.761724413);(39.02292652,2.235159979);(49.00727645,3.64687195);(51.02292652,3.088866654);(53.03857658,1.484215216);(59.01275576,1.535711567);(65.03857658,5.599038986);(67.05422664,1.342093638);(68.99710569,1.84673004);(75.02292652,2.172643155);(77.00219107,1.686220268);(77.03857658,1.023679446);(79.01784114,1.848476708);(79.05422664,3.022733148);(93.0334912,2.544948512);(105.0334912,4.059721945);(107.0491413,4.969385849);(109.0647913,1.051770372);(117.0334912,2.458214298);(119.0491413,3.348745319);(121.0647913,1.010502629);(123.0440559,2.678443058);(135.0440559,1.350587944);(170.974656,1.393681792);(172.9903061,3.120770891);(175.0059561,1.299895389);(187.0059561,1.942934462);(199.0059561,0.9856821609);(200.9852207,1.201004029);(203.0008707,1.303613885);(217.0165208,1.435377675)
Predicted LC-MS/MS	Not Available	Negative	low	View Spectrum	(59.01385292,1.583314561);(163.0400677,1.595153567);(181.0506323,3.417874549);(217.017618,9.375628941);(242.9968825,16.17529676);(261.0074472,57.59733082)
Predicted LC-MS/MS	Not Available	Negative	med	View Spectrum	(59.01385292,4.482813319);(96.96010309,2.22455472);(121.029503,2.590070474);(123.045153,1.546107509);(133.029503,1.533930104);(135.045153,4.961765688);(137.0608031,4.230981902);(163.0400677,11.20087555);(175.0036822,1.447203989);(177.0193322,2.083945572);(179.0349823,2.750925186);(181.0506323,17.03180207);(217.017618,5.133821025);(242.9968825,9.27027952);(261.0074472,10.371074)
Predicted LC-MS/MS	Not Available	Negative	high	View Spectrum	(41.00328823,4.294920664);(44.99820285,2.560374021);(59.01385292,16.74957715);(64.97027385,1.890290172);(80.96518847,10.47375734);(82.98083854,2.009433696);(84.9964886,2.765953521);(96.96010309,2.357687551);(121.029503,2.183695418);(135.045153,6.56597716);(137.0608031,6.019802249);(161.0244176,1.55297878);(163.0400677,15.24279741);(181.0506323,4.901830666);(242.9968825,1.495644034)
Predicted LC-MS/MS	Not Available	Negative	low	View Spectrum	(242.99688,15.38);(242.99688,15.38);(242.99688,15.38);(242.99688,15.38);(242.99688,15.38);(242.99688,15.38);(242.99688,15.38);(261.00745,100.0);(261.00745,100.0);(261.00745,100.0);(261.00745,100.0);(261.00745,100.0);(261.00745,100.0);(261.00745,100.0)
Predicted LC-MS/MS	Not Available	Negative	medium	View Spectrum	(59.01385,12.04);(96.9601,100.0);(135.04515,8.51);(199.00705,9.01);(199.00705,9.01);(215.00197,24.26);(215.00197,24.26);(215.00197,24.26);(215.00197,24.26);(215.00197,24.26);(217.01762,59.8);(217.01762,59.8);(217.01762,59.8);(217.01762,59.8);(217.01762,59.8);(217.01762,59.8);(242.99688,15.69);(242.99688,15.69);(242.99688,15.69);(242.99688,15.69);(242.99688,15.69);(242.99688,15.69);(242.99688,15.69);(261.00745,32.09);(261.00745,32.09);(261.00745,32.09);(261.00745,32.09);(261.00745,32.09);(261.00745,32.09);(261.00745,32.09)
Predicted LC-MS/MS	Not Available	Negative	high	View Spectrum	(41.00329,6.26);(65.00329,18.08);(65.03967,82.41);(67.01894,30.18);(77.00329,8.15);(79.01894,8.84);(80.96519,26.76);(89.00329,7.16);(96.9601,100.0);(107.01385,6.34);(107.05024,11.37);(109.0295,31.03);(109.0295,31.03);(119.01385,6.31);(119.01385,6.31);(121.0295,26.74);(121.0295,26.74);(121.0295,26.74);(121.0295,26.74);(123.04515,14.94);(123.04515,14.94);(123.04515,14.94);(135.04515,6.75);(136.95502,15.57);(146.97575,5.88);(175.00705,9.09);(187.00705,12.74);(189.0227,16.73);(200.98632,6.07);(200.98632,6.07);(215.00197,21.13);(215.00197,21.13);(215.00197,21.13);(215.00197,21.13);(215.00197,21.13);(218.99688,51.48);(242.99688,8.66);(242.99688,8.66);(242.99688,8.66);(242.99688,8.66);(242.99688,8.66);(242.99688,8.66);(242.99688,8.66)
Predicted LC-MS/MS	Not Available	Positive	low	View Spectrum	(137.05971,16.56);(137.05971,16.56);(161.02332,12.92);(161.02332,12.92);(161.02332,12.92);(161.02332,12.92);(163.03897,37.45);(163.03897,37.45);(163.03897,37.45);(163.03897,37.45);(163.03897,37.45);(165.05462,69.93);(165.05462,69.93);(165.05462,69.93);(165.05462,69.93);(165.05462,69.93);(165.05462,69.93);(217.01652,23.76);(217.01652,23.76);(217.01652,23.76);(217.01652,23.76);(217.01652,23.76);(245.01144,100.0);(245.01144,100.0);(245.01144,100.0);(245.01144,100.0);(245.01144,100.0);(245.01144,100.0);(245.01144,100.0);(263.022,39.68);(263.022,39.68);(263.022,39.68);(263.022,39.68);(263.022,39.68);(263.022,39.68);(263.022,39.68)
Predicted LC-MS/MS	Not Available	Positive	medium	View Spectrum	(105.03349,15.92);(107.04914,14.01);(109.02841,20.53);(109.02841,20.53);(109.02841,20.53);(111.04406,12.38);(111.04406,12.38);(111.04406,12.38);(121.02841,23.9);(121.02841,23.9);(123.04406,54.35);(123.04406,54.35);(133.02841,11.55);(133.02841,11.55);(133.02841,11.55);(133.02841,11.55);(135.04406,27.22);(135.04406,27.22);(135.04406,27.22);(137.05971,42.45);(137.05971,42.45);(147.04406,35.41);(147.04406,35.41);(149.05971,25.89);(149.05971,25.89);(163.03897,15.52);(163.03897,15.52);(163.03897,15.52);(163.03897,15.52);(163.03897,15.52);(165.05462,100.0);(165.05462,100.0);(165.05462,100.0);(165.05462,100.0);(165.05462,100.0);(165.05462,100.0);(181.04954,20.02);(181.04954,20.02);(181.04954,20.02);(181.04954,20.02);(181.04954,20.02);(181.04954,20.02);(181.04954,20.02);(183.06519,19.04);(183.06519,19.04);(183.06519,19.04);(183.06519,19.04);(183.06519,19.04);(183.06519,19.04);(183.06519,19.04);(217.01652,15.79);(217.01652,15.79);(217.01652,15.79);(217.01652,15.79);(217.01652,15.79);(245.01144,23.59);(245.01144,23.59);(245.01144,23.59);(245.01144,23.59);(245.01144,23.59);(245.01144,23.59);(245.01144,23.59);(263.022,17.48);(263.022,17.48);(263.022,17.48);(263.022,17.48);(263.022,17.48);(263.022,17.48);(263.022,17.48)
Predicted LC-MS/MS	Not Available	Positive	high	View Spectrum	(65.03858,8.28);(65.03858,8.28);(79.05423,26.6);(82.97974,8.61);(95.04914,14.39);(95.04914,14.39);(105.03349,28.29);(107.04914,12.48);(109.02841,22.8);(109.02841,22.8);(109.02841,22.8);(117.03349,47.16);(119.01276,9.4);(119.04914,100.0);(121.02841,14.23);(121.02841,14.23);(121.06479,23.24);(123.04406,20.47);(123.04406,20.47);(125.05971,8.73);(133.02841,18.16);(133.02841,18.16);(133.02841,18.16);(133.02841,18.16);(135.04406,9.21);(135.04406,9.21);(135.04406,9.21);(137.05971,9.77);(137.05971,9.77);(145.02841,30.7);(147.04406,32.28);(147.04406,32.28);(149.05971,10.94);(149.05971,10.94)

Food Sources

No food source information available

Food Sources of its Food Phytochemical(s)

Food Phytochemical	Food Source	Food Source Group
Caffeic acid	American cranberry	Fruit, Berries	Publications	Show
Ferulic acid	American cranberry	Fruit, Berries	Publications	Show
Caffeic acid	Apple	Fruit, Pomes	Publications	Show
Caffeic acid	Apple juice	Beverages, Non-alcoholic	Publications	Show
Ferulic acid	Apple juice	Beverages, Non-alcoholic	Publications	Show
Caffeic acid	Beer	Beverages, Alcoholic	Publications	Show
Ferulic acid	Beer	Beverages, Alcoholic	Publications	Show
Ferulic acid	Bilberry	Fruit, Berries	Publications	Show
Ferulic acid	Black mulberry	Fruit, Berries	Publications	Show
Caffeic acid	Blackberry	Fruit, Berries	Publications	Show
Ferulic acid	Blackberry	Fruit, Berries	Publications	Show
Caffeic acid	Blueberry	Fruit, Berries	Publications	Show
Ferulic acid	Blueberry	Fruit, Berries	Publications	Show
Caffeic acid	Broccoli	Vegetables, Cabbages	Publications	Show
Ferulic acid	Broccoli	Vegetables, Cabbages	Publications	Show
Caffeic acid	Carrot	Vegetables, Root vegetables	Publications	Show
Caffeic acid	Cider	Beverages, Alcoholic	Publications	Show
Ferulic acid	Cocoa bean	Cocoa and cocoa products	Publications	Show
Caffeic acid	Coffee	Coffee and coffee products	Publications	Show
Ferulic acid	Coffee	Coffee and coffee products	Publications	Show
Ferulic acid	Common bean	Pulses and beans	Publications	Show
Ferulic acid	Common walnut	Nuts	Publications	Show
Caffeic acid	Common wheat	Cereals and cereal products	Publications	Show
Ferulic acid	Common wheat	Cereals and cereal products	Publications	Show
Ferulic acid	Corn	Cereals and cereal products	Publications	Show
Ferulic acid	Date	Fruit, Other fruits	Publications	Show
Caffeic acid	Eggplant	Vegetables, Fruit vegetables	Publications	Show
Ferulic acid	Eggplant	Vegetables, Fruit vegetables	Publications	Show
Caffeic acid	European cranberry	Fruit, Berries	Publications	Show
Ferulic acid	European cranberry	Fruit, Berries	Publications	Show
Caffeic acid	European plum	Fruit, Drupes	Publications	Show
Ferulic acid	Fennel	Herbs and Spices	Publications	Show
Ferulic acid	Grapefruit	Fruit, Citrus	Publications	Show
Ferulic acid	Hard wheat	Cereals and cereal products	Publications	Show
Caffeic acid	Mate	Teas and herbal teas	Publications	Show
Caffeic acid	Olive, black	Fruit, Drupes	Publications	Show
Ferulic acid	Olive, black	Fruit, Drupes	Publications	Show
Caffeic acid	Olive, green	Fruit, Drupes	Publications	Show
Ferulic acid	Olive, green	Fruit, Drupes	Publications	Show
Ferulic acid	Orange juice	Beverages, Non-alcoholic	Publications	Show
Caffeic acid	Pear	Fruit, Pomes	Publications	Show
Ferulic acid	Rapeseed	Oilseed crops	Publications	Show
Ferulic acid	Red raspberry	Fruit, Berries	Publications	Show
Ferulic acid	Rice	Cereals and cereal products	Publications	Show
Ferulic acid	Rosemary	Herbs and Spices	Publications	Show
Ferulic acid	Rye bread	Cereals and cereal products	Publications	Show
Ferulic acid	Spinach	Vegetables, Leaf vegetables	Publications	Show
Caffeic acid	Strawberry	Fruit, Berries	Publications	Show
Ferulic acid	Strawberry	Fruit, Berries	Publications	Show
Caffeic acid	Sweet cherry	Fruit, Drupes	Publications	Show
Ferulic acid	Sweet orange	Fruit, Citrus	Publications	Show
Ferulic acid	Tarragon	Herbs and Spices	Publications	Show
Caffeic acid	Tomato	Vegetables, Fruit vegetables	Publications	Show
Ferulic acid	Tomato	Vegetables, Fruit vegetables	Publications	Show
Ferulic acid	White wine	Beverages, Alcoholic	Publications	Show
Caffeic acid	White wine grape	Fruit, Berries	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
Caffeic acid	Dihydrocaffeic acid-3-sulfate	human	plasma	host metabolism	Not Available	Not Available	Not Available	C₉H₁₀O₇S	262.014723836		Publications
Orange flavanones	Dihydrocaffeic acid-3-sulfate	Not Available	Not Available	Not Available	Not Available	Not Available	Not Available	C₉H₁₀O₇S	262.014723836	Detailed Intervention Studies
Black tea Flavan-3-ols	Dihydrocaffeic acid-3-sulfate	human	urine	host-gut microbiota co-metabolite	Not Available	Not Available	<1%	C₉H₁₀O₇S	262.014723836	Detailed Intervention Studies	Publications
Coffee Chlorogenic acids	Dihydrocaffeic acid-3-sulfate	human	plasma, urine	host-gut microbiota co-metabolite	5h-8h	200-500 nmol/L	5-10%	C₉H₁₀O₇S	262.014723836	Detailed Intervention Studies	Publications
Yerba mate Chlorogenic acids	Dihydrocaffeic acid-3-sulfate	human	urine	host-gut microbiota co-metabolite	Not Available	Not Available	1-5%	C₉H₁₀O₇S	262.014723836	Detailed Intervention Studies	Publications
Coffee hydroxycinnamates	Dihydrocaffeic acid-3-sulfate	Not Available	Not Available	Not Available	Not Available	Not Available	Not Available	C₉H₁₀O₇S	262.014723836	Detailed Intervention Studies
Ferulic acid	Dihydrocaffeic acid-3-sulfate	human	urine	host-gut microbiota co-metabolite	Not Available	Not Available	<1%	C₉H₁₀O₇S	262.014723836	Detailed Intervention Studies	Publications

Inter-Individual Variations in Metabolism

	Food Phytochemical		Metabolite	Effect	Value
	Coffee Chlorogenic acids		Dihydrocaffeic acid-3-sulfate	Microbiota	Effect, clusters	Publications

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Showing entry for Dihydrocaffeic acid-3-sulfate