PhytoHub: Showing entry for Narirutin

Narirutin

Identification

PhytoHub ID

PHUB000392

Name

Narirutin

Systematic Name

Not Available

Synonyms

Isonaringin
Naringenin 7-O-rutinoside

CAS Number

14259-46-2

Average Mass

580.539

Monoisotopic Mass

580.17920571

Chemical Formula

C₂₇H₃₂O₁₄

IUPAC Name

5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one

InChI Key

HXTFHSYLYXVTHC-TUURGLJWSA-N

InChI Identifier

InChI=1S/C27H32O14/c1-10-20(31)22(33)24(35)26(38-10)37-9-18-21(32)23(34)25(36)27(41-18)39-13-6-14(29)19-15(30)8-16(40-17(19)7-13)11-2-4-12(28)5-3-11/h2-7,10,16,18,20-29,31-36H,8-9H2,1H3/t10-,16?,18+,20-,21+,22+,23-,24+,25+,26+,27+/m0/s1

SMILES

C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=CC(O)=C4C(=O)CC(OC4=C3)C3=CC=C(O)C=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O

Structure

Similar Structures

Calculated Properties

Solubility (ALOGPS): 3.08e+00 g/l
LogS (ALOGPS): -2.28
LogP (ALOGPS): -0.35
Hydrogen Acceptors: 14
Hydrogen Donors: 8
Rotatable Bond Count: 6
Polar Surface Area: 225.05999999999997
Refractivity: 134.30380000000005
Polarizability: 56.55559613093186
Formal Charge: 0
Physiological Charge: 0
pKa (strongest basic): -3.612182351683661
pKa (strongest acidic): 8.579286961223794
Number of Rings: 5
Rule of Five: No
Bioavailability: No
Ghose Filter: No
Veber's Rule: No
MDDR-like Rule: Yes

External Links

PubChem: 477826
PeakForestCompound: 000343

Taxonomy as Food Phytochemical

Family: Polyphenols
Class: Flavonoids
Sub-class: Flavanones

Classyfire Taxonomy

Kingdom Name: Organic compounds
Class: Flavonoids
Super-class: Phenylpropanoids and polyketides
Sub-class: Flavonoid glycosides
Direct Parent Name: Flavonoid-7-O-glycosides
Alternative Parent Names: ["1-hydroxy-2-unsubstituted benzenoids", "1-hydroxy-4-unsubstituted benzenoids", "4'-hydroxyflavonoids", "5-hydroxyflavonoids", "Acetals", "Alkyl aryl ethers", "Aryl alkyl ketones", "Benzene and substituted derivatives", "Chromones", "Disaccharides", "Flavanones", "Hydrocarbon derivatives", "O-glycosyl compounds", "Organic oxides", "Oxacyclic compounds", "Oxanes", "Phenolic glycosides", "Polyols", "Secondary alcohols", "Vinylogous acids"]
External Descriptor Annotations: Not Available
Substituent Names: ["1-benzopyran", "1-hydroxy-2-unsubstituted benzenoid", "1-hydroxy-4-unsubstituted benzenoid", "4'-hydroxyflavonoid", "5-hydroxyflavonoid", "Acetal", "Alcohol", "Alkyl aryl ether", "Aromatic heteropolycyclic compound", "Aryl alkyl ketone", "Aryl ketone", "Benzenoid", "Benzopyran", "Chromane", "Chromone", "Disaccharide", "Ether", "Flavan", "Flavanone", "Flavonoid-7-o-glycoside", "Glycosyl compound", "Hydrocarbon derivative", "Hydroxyflavonoid", "Ketone", "Monocyclic benzene moiety", "O-glycosyl compound", "Organic oxide", "Organic oxygen compound", "Organoheterocyclic compound", "Organooxygen compound", "Oxacycle", "Oxane", "Phenol", "Phenolic glycoside", "Polyol", "Secondary alcohol", "Vinylogous acid"]

Spectra from Phytohub

Spectrum Type	Instrument Type	Ion Mode	Collision Energy Level	View	Peaks

Predicted LC-MS/MS	Not Available	Positive	low	View Spectrum	(27.0234751,0.7805298413);(87.04460446,0.7020412287);(95.04968984,0.6790354403);(119.0496898,1.524539934);(121.0653399,1.786829429);(137.0602545,1.016637644);(145.0500838,0.55406976);(147.0657338,3.040606122);(153.0187836,1.344865058);(155.0344337,0.4947590816);(165.0762985,0.5941446509);(177.0762985,0.7015450781);(189.0762985,0.4515914343);(219.0868632,0.6368598933);(249.0974279,0.9923694846);(255.0657338,11.21956193);(257.0813839,1.174579556);(271.0606485,0.5070845015);(273.0762985,27.69195456);(309.1185573,1.906592583);(327.1291219,0.5047295185);(399.1079926,0.4893884629);(417.1185573,1.587594209);(417.1185573,2.396421367);(433.1346012,1.344154769);(435.1291219,2.2405794);(459.1138658,0.5143051164);(461.1295159,2.510664333);(545.1659014,1.356435466);(563.1764661,16.45381213);(581.1870307,12.80171802)
Predicted LC-MS/MS	Not Available	Positive	med	View Spectrum	(45.03403978,0.9155773282);(95.04968984,0.830815545);(107.0496898,2.151233065);(119.0496898,1.203811106);(121.0289544,0.7143174313);(121.0653399,2.039442233);(123.0446045,0.7924909042);(129.0551691,1.353604878);(137.023869,6.111288575);(145.0500838,0.5550408035);(147.0446045,1.023601424);(147.0657338,4.094559993);(153.0187836,3.724976819);(163.0606485,1.746750758);(165.0762985,1.173177412);(243.0657338,1.125520684);(255.0657338,19.38505208);(257.0813839,0.6224607807);(271.0606485,1.269255199);(273.0762985,33.92444373);(291.1079926,0.5639688571);(299.0766924,0.9261019714);(309.1185573,1.30501484);(417.1185573,2.891314734);(417.1185573,1.46313183);(435.1291219,2.893946498);(461.1295159,0.5291290388);(545.1659014,0.6001223847);(551.1764661,0.6327722466);(563.1764661,2.63706118);(581.1870307,0.800015676)
Predicted LC-MS/MS	Not Available	Positive	high	View Spectrum	(45.03403978,1.991691467);(75.04460446,1.385284105);(95.04968984,1.131138421);(119.0496898,5.585349182);(121.0289544,2.674689718);(121.0653399,4.877478286);(123.0446045,1.652374984);(131.0708192,1.371572884);(137.023869,3.878293266);(137.0602545,2.922928103);(145.0289544,1.432024837);(145.0500838,1.677042255);(147.0446045,1.100289793);(147.0657338,3.407633573);(153.0187836,9.499295744);(155.0344337,2.907201082);(161.0449984,1.41302472);(161.0813839,1.213689756);(163.0395191,1.813525178);(163.0606485,4.831649686);(231.0657338,1.121560902);(241.0500838,1.13668947);(243.0657338,1.671099421);(255.0657338,10.18135199);(257.0813839,1.63102123);(271.0817778,2.560215809);(273.0762985,15.77223394);(287.0766924,1.933656917);(313.0923425,2.460905622);(519.1502513,1.499104525);(563.1764661,3.265983127)
Predicted LC-MS/MS	Not Available	Negative	low	View Spectrum	(56.99765427,2.75124858);(57.03403978,1.087171216);(59.01330434,0.9487152569);(73.0289544,1.932579574);(87.00821896,2.553412975);(87.04460446,2.011458634);(89.02386902,1.057122893);(93.03403978,1.452434011);(101.023869,1.015886585);(117.0551691,1.233885487);(145.0500838,4.258652193);(163.0606485,6.798718391);(219.0868632,0.7739228079);(235.0817778,1.410342174);(249.0974279,2.049281345);(253.0500838,3.873484555);(271.0606485,19.32692584);(279.1079926,1.721604727);(295.1029072,1.00671614);(307.1029072,0.951545964);(313.0712131,1.274809584);(325.1134719,0.8252925587);(415.1029072,2.164059834);(431.1189512,1.813012763);(433.1134719,5.057592222);(475.1240366,1.07559797);(491.1189512,1.299323605);(493.1346012,0.7576115848);(549.160816,0.9000431065);(561.160816,6.4540312);(579.1713807,20.16351623)
Predicted LC-MS/MS	Not Available	Negative	med	View Spectrum	(43.01838972,2.922687924);(59.01330434,2.019310094);(71.01330434,0.8570283012);(73.0289544,1.311068555);(87.00821896,1.307903327);(87.04460446,1.101663014);(89.02386902,4.351765382);(93.03403978,1.420015733);(133.0500838,1.094422523);(145.0500838,10.56382335);(161.0449984,1.136978202);(163.0606485,9.825030519);(177.0187836,0.8703733625);(205.0712131,0.7824618396);(229.0500838,1.424864368);(253.0500838,5.567120885);(271.0606485,32.35693529);(279.1079926,0.9511609541);(283.0606485,0.9839627156);(307.1029072,1.494695715);(313.0712131,1.086186);(325.1134719,1.192706128);(329.0661278,0.8112660332);(415.1029072,1.871635041);(431.1189512,1.061641172);(433.1134719,1.699300867);(535.1451659,0.7767374224);(549.160816,0.867173235);(561.160816,4.423129759);(561.160816,1.731190337);(579.1713807,2.13576195)
Predicted LC-MS/MS	Not Available	Negative	high	View Spectrum	(41.00273965,1.337973863);(43.01838972,3.13459821);(55.01838972,1.378373239);(56.99765427,0.7333538544);(57.03403978,1.732473378);(59.01330434,2.60241138);(73.0289544,2.01517588);(83.01330434,0.7979826936);(85.0289544,1.081563011);(93.03403978,4.866703601);(103.0395191,0.7590307789);(117.0340398,2.487732647);(119.0496898,5.541041277);(135.008219,1.016397996);(135.0446045,1.746168029);(145.0289544,0.7899955782);(145.0500838,2.746364344);(149.023869,1.769312687);(151.0031336,1.450431092);(163.0606485,8.176187452);(177.0187836,1.538729446);(187.0606485,0.7986146547);(201.0551691,3.893136918);(205.0712131,0.7362221699);(227.0344337,1.096468403);(229.0500838,5.548533286);(253.0500838,6.475034069);(255.0293483,0.9740133021);(269.0449984,1.970313881);(271.0606485,30.06567581);(489.1396866,0.739987065)

Food Sources

Name	Group
Globe artichoke	Vegetables, Other vegetables	Publications	Show
Grapefruit	Fruit, Citrus	Publications	Show
Grapefruit juice	Beverages, Non-alcoholic	Publications	Show
Orange juice	Beverages, Non-alcoholic	Publications	Show
Sweet orange	Fruit, Citrus	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
Narirutin	Naringenin	Not Available	Not Available	Not Available	Not Available	Not Available	Not Available	C₁₅H₁₂O₅	272.068473486	Detailed Intervention Studies
Narirutin	Naringenin-4'-glucuronide	human rat	plasma (major), urine (major)	host metabolism	Not Available	Not Available	Not Available	C₂₁H₂₀O₁₁	448.100561464		Publications
Narirutin	Naringenin-7-glucuronide	human rat	plasma (major), urine (major)	host metabolism	Not Available	Not Available	Not Available	C₂₁H₂₀O₁₁	448.100561464		Publications
Narirutin	Naringenin-diglucuronide	human	urine (minor)	host metabolism	Not Available	Not Available	Not Available	C₂₇H₂₈O₁₇	624.5095093		Publications

Inter-Individual Variations in Metabolism

	Food Phytochemical		Metabolite	Effect	Value

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Showing entry for Narirutin