PhytoHub: Showing entry for Arecoline

Arecoline

Identification

PhytoHub ID

PHUB000837

Name

Arecoline

Systematic Name

Not Available

Synonyms

Not Available

CAS Number

63-75-2

Average Mass

155.197

Monoisotopic Mass

155.094628663

Chemical Formula

C₈H₁₃NO₂

IUPAC Name

methyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate

InChI Key

HJJPJSXJAXAIPN-UHFFFAOYSA-N

InChI Identifier

InChI=1S/C8H13NO2/c1-9-5-3-4-7(6-9)8(10)11-2/h4H,3,5-6H2,1-2H3

SMILES

COC(=O)C1=CCCN(C)C1

Structure

Similar Structures

Calculated Properties

Solubility (ALOGPS): 4.46e+02 g/l
LogS (ALOGPS): 0.46
LogP (ALOGPS): 0.55
Hydrogen Acceptors: 2
Hydrogen Donors: 0
Rotatable Bond Count: 2
Polar Surface Area: 29.54
Refractivity: 43.861000000000004
Polarizability: 17.102589891339612
Formal Charge: 0
Physiological Charge: 1
pKa (strongest basic): 8.225681392301013
pKa (strongest acidic): Not Available
Number of Rings: 1
Rule of Five: Yes
Bioavailability: Yes
Ghose Filter: No
Veber's Rule: Yes
MDDR-like Rule: No

Taxonomy as Food Phytochemical

Family: N-containing compounds
Class: Alkaloids
Sub-class: Pyrrolidine and piperidine alkaloids

Taxonomy as Metabolite

Metabolite Family: N-containing compound metabolites
Metabolite Class: Alkaloid metabolites
Metabolite Sub-class: Pyrrolidines and piperidines (parent, host and microbial metabolites)

Taxonomy of its Food Phytochemical Precursor(s)

Food Phytochemical	Family	Class	Sub-class
Arecoline	N-containing compounds	Alkaloids	Pyrrolidine and piperidine alkaloids	Show Food Phytochemical

Classyfire Taxonomy

Kingdom Name: Organic compounds
Class: Not Available
Super-class: Alkaloids and derivatives
Sub-class: Not Available
Direct Parent Name: Alkaloids and derivatives
Alternative Parent Names: ["Amino acids and derivatives", "Azacyclic compounds", "Carbonyl compounds", "Enoate esters", "Hydrocarbon derivatives", "Hydropyridines", "Methyl esters", "Monocarboxylic acids and derivatives", "Organic oxides", "Organopnictogen compounds", "Trialkylamines"]
External Descriptor Annotations: ["Pyridine alkaloids", "enoate ester", "methyl ester", "pyridine alkaloid", "tetrahydropyridine"]
Substituent Names: ["Aliphatic heteromonocyclic compound", "Alkaloid or derivatives", "Alpha,beta-unsaturated carboxylic ester", "Amine", "Amino acid or derivatives", "Azacycle", "Carbonyl group", "Carboxylic acid derivative", "Carboxylic acid ester", "Enoate ester", "Hydrocarbon derivative", "Hydropyridine", "Methyl ester", "Monocarboxylic acid or derivatives", "Organic nitrogen compound", "Organic oxide", "Organic oxygen compound", "Organoheterocyclic compound", "Organonitrogen compound", "Organooxygen compound", "Organopnictogen compound", "Tertiary aliphatic amine", "Tertiary amine"]

Spectra from Phytohub

Spectrum Type	Instrument Type	Ion Mode	Collision Energy Level	View	Peaks

Predicted GC-MS	GC-MS	Positive	Not Available	View Spectrum	(25.00727602,1.673362247);(27.02292522,4.338735162);(39.02292522,2.213793424);(41.03857442,3.804582293);(42.03382302,6.243812532);(43.04164762,1.563668995);(57.05729682,2.036633178);(58.06512142,3.193945732);(68.04947222,3.326779975);(70.06512142,6.002998653);(71.07294602,1.459284066);(81.03348852,1.686027096);(82.06512142,1.651510209);(94.06512142,1.860269396);(95.07294602,4.045328264);(96.08077062,12.84158143);(97.08859522,2.746756664);(98.03622722,2.632390573);(99.04405182,1.548878797);(111.0440518,2.300267639);(112.0518764,2.13549615);(123.0678601,2.897625751);(124.0756847,4.496217905);(125.0835093,2.11278835);(126.0549496,1.580039012);(127.0627742,2.067916942);(128.0705988,1.649735107);(139.0627742,2.830293629);(140.0705988,5.593391752);(154.086248,3.788573714);(155.0940726,3.677315365)
Predicted GC-MS	GC-MS	Ei	Not Available	View Spectrum	(27.02292522,1.296963531);(28.01817382,0.9143705334);(39.02292522,1.52181329);(41.03857442,2.46572457);(42.03382302,2.610464234);(57.05729682,1.226332617);(58.06512142,2.189652644);(68.04947222,2.021848699);(69.05729682,0.8180358452);(70.06512142,3.444676384);(71.07294602,0.9561776671);(81.03348852,1.280139851);(94.06512142,1.484143072);(95.07294602,3.61531521);(96.08077062,7.934277835);(97.08859522,1.822062324);(98.03622722,1.374201174);(99.04405182,0.9192759223);(111.0440518,1.404559363);(112.0518764,1.415858304);(113.059701,0.8888420931);(123.0678601,2.133520443);(124.0756847,3.450292217);(125.0835093,1.426372266);(126.0549496,1.037820433);(127.0627742,1.354976762);(128.0705988,1.082960109);(138.0913339,0.8357681676);(139.0627742,1.730835006);(140.0705988,4.151742454);(155.0940726,2.497394079)
Predicted LC-MS/MS	Not Available	Positive	low	View Spectrum	(28.01872406,0.0877374411);(30.03437413,0.0745896316);(41.03912516,0.4233126713);(43.05477522,0.1113597082);(44.05002419,0.0692560103);(45.07042529,0.0555698858);(56.05002419,0.1296624211);(61.0289544,0.0969584637);(67.05477522,0.2050668405);(68.05002419,0.152873277);(69.07042529,0.145502446);(70.06567426,0.1889273414);(81.03403978,0.5187430726);(85.0289544,0.1233811636);(95.04968984,1.934945403);(96.08132432,2.341681384);(97.06533991,1.32254419);(110.0605889,0.0638337382);(111.0446045,0.7661824096);(112.0398534,0.1171357052);(113.0602545,1.070597571);(116.0711536,0.125334862);(124.0762389,18.27690873);(125.0602545,2.319426137);(126.091889,2.038973655);(127.0759046,3.619733725);(128.0711536,0.196368035);(129.0915547,0.7510352537);(130.0868036,0.0755670596);(140.0711536,1.324118445);(156.1024537,61.27267332)
Predicted LC-MS/MS	Not Available	Positive	med	View Spectrum	(41.03912516,2.251688629);(43.05477522,1.027988149);(44.05002419,2.2166288);(45.07042529,0.3126739802);(53.03912516,0.3730681654);(56.05002419,0.6867768782);(65.03912516,0.3135054115);(67.05477522,0.6838382371);(68.05002419,1.031948093);(69.07042529,0.3354423273);(70.06567426,5.613169559);(72.08132432,5.550387581);(79.01838972,0.8457425802);(81.03403978,2.20430922);(85.0289544,0.5151652145);(95.04968984,1.568477432);(96.08132432,9.817457165);(97.06533991,0.6653107859);(110.0605889,0.3601217425);(111.0446045,2.423767939);(113.0602545,1.953343939);(114.0555035,0.4761518017);(124.0762389,18.30788834);(125.0602545,4.863561718);(126.091889,1.146234786);(127.0759046,3.007848073);(128.0711536,1.488720254);(129.0915547,0.8887928597);(130.0868036,0.4481919602);(140.0711536,1.629733923);(156.1024537,26.99206445)
Predicted LC-MS/MS	Not Available	Positive	high	View Spectrum	(27.0234751,0.7688115482);(28.01872406,0.5336416887);(30.03437413,1.073256039);(41.03912516,12.39605369);(43.05477522,2.807044124);(44.05002419,2.851818912);(46.06567426,1.277855341);(51.0234751,2.817603242);(53.03912516,3.736118689);(54.03437413,2.181539201);(55.01838972,1.075775608);(56.05002419,2.778094978);(65.03912516,2.929174991);(67.05477522,6.981041008);(68.05002419,2.379676116);(69.07042529,7.233002828);(70.06567426,8.232583797);(79.01838972,1.252956124);(80.05002419,4.301778393);(81.03403978,7.257869553);(84.04493881,0.6699896281);(85.0289544,3.555157834);(95.04968984,5.887594321);(96.08132432,4.717240025);(97.06533991,4.242493725);(98.06058888,0.6226172707);(110.0605889,1.225119679);(111.0446045,1.234301762);(124.0762389,1.855399617);(125.0602545,0.531328792);(140.0711536,0.5930614709)
Predicted LC-MS/MS	Not Available	Negative	low	View Spectrum	(15.0234751,0.2444749044);(27.0234751,0.0209287152);(28.01872406,0.0655683436);(31.01838972,0.2408446065);(39.0234751,0.0564904382);(41.03912516,0.0290980903);(42.03437413,0.1226034907);(44.05002419,0.0552426735);(59.01330434,0.0761240199);(68.05002419,0.0565956598);(70.06567426,0.0759782324);(78.03437413,0.0111836697);(83.01330434,0.0179046142);(93.03403978,0.0570217904);(94.06567426,0.5663639601);(95.04968984,0.0647886982);(96.04493881,0.0756790726);(106.0292887,0.056291428);(108.0449388,0.0618844995);(109.0289544,0.0570454279);(111.0446045,0.3760557077);(112.0398534,0.0272459146);(122.0605889,8.739985198);(123.0446045,0.4560620055);(124.0762389,1.354983822);(125.0602545,0.8732357108);(126.0555035,0.1725503655);(127.0759046,0.4126181149);(128.0711536,0.3590484043);(138.0555035,1.583146945);(154.0868036,83.63295548)
Predicted LC-MS/MS	Not Available	Negative	med	View Spectrum	(15.0234751,0.3356554086);(26.003074,0.1389607106);(28.01872406,0.3480548675);(31.01838972,0.3837103491);(39.0234751,0.1508442336);(42.03437413,0.2509521869);(53.00273965,0.8826547396);(54.03437413,0.2604438336);(55.01838972,0.1951233383);(59.01330434,0.4751955026);(68.05002419,0.8648763577);(68.99765427,0.1715503067);(70.06567426,1.498811239);(79.01838972,0.2975394521);(83.01330434,0.9005699625);(85.0289544,1.312618408);(87.04460446,0.5231239337);(94.06567426,2.906738238);(96.04493881,0.269779408);(106.0292887,0.1444558236);(108.0449388,0.7389807586);(109.0289544,0.5479383586);(111.0446045,1.529655845);(114.0555035,0.1282155739);(122.0605889,16.05033381);(124.0762389,2.906224814);(125.0602545,0.3447045424);(126.0555035,0.7710240996);(128.0711536,0.457603296);(138.0555035,6.094091342);(154.0868036,58.11956926)
Predicted LC-MS/MS	Not Available	Negative	high	View Spectrum	(25.00782503,1.05211253);(27.0234751,1.039178954);(28.01872406,1.517412957);(29.00273965,4.065716465);(42.03437413,7.110216879);(44.05002419,1.7550358);(53.00273965,8.330829251);(54.03437413,2.698091577);(55.01838972,1.751356038);(59.01330434,5.876795896);(67.05477522,1.19273922);(68.05002419,3.521591457);(68.99765427,0.8551799028);(70.06567426,7.791815038);(78.03437413,2.372099508);(82.02928875,0.9487535151);(83.01330434,1.376291414);(85.0289544,1.699553706);(93.03403978,0.9756059309);(94.06567426,9.880625298);(95.04968984,1.350714179);(96.04493881,2.488493851);(106.0292887,1.631472208);(108.0449388,4.840511701);(111.0446045,2.165678004);(112.0398534,0.9935024059);(122.0605889,6.991820027);(124.0762389,3.569520236);(126.0555035,1.561700751);(138.0555035,5.681160619);(154.0868036,2.91442468)
Predicted LC-MS/MS	Not Available	Negative	low	View Spectrum	(94.06622,31.72);(94.06622,31.72);(94.06622,31.72);(94.06622,31.72);(154.08735,100.0);(154.08735,100.0);(154.08735,100.0);(154.08735,100.0);(154.08735,100.0);(154.08735,100.0);(154.08735,100.0)
Predicted LC-MS/MS	Not Available	Negative	medium	View Spectrum	(94.06622,45.0);(94.06622,45.0);(94.06622,45.0);(94.06622,45.0);(96.08187,100.0);(96.08187,100.0);(96.08187,100.0);(96.08187,100.0);(122.06114,69.68);(122.06114,69.68);(122.06114,69.68);(122.06114,69.68);(122.06114,69.68);(138.05605,14.09);(138.05605,14.09);(138.05605,14.09);(138.05605,14.09);(138.05605,14.09);(138.05605,14.09);(138.05605,14.09);(154.08735,80.45);(154.08735,80.45);(154.08735,80.45);(154.08735,80.45);(154.08735,80.45);(154.08735,80.45);(154.08735,80.45)
Predicted LC-MS/MS	Not Available	Negative	high	View Spectrum	(28.01927,12.7);(31.01894,42.14);(39.02402,11.35);(42.03492,21.88);(44.05057,28.26);(59.01385,100.0);(65.03967,12.32);(67.05532,16.34);(68.05057,17.91);(68.05057,17.91);(70.06622,12.48);(70.06622,12.48);(78.03492,7.07);(80.05057,34.78);(90.03492,14.38);(92.05057,12.34);(94.06622,41.78);(94.06622,41.78);(94.06622,41.78);(94.06622,41.78);(96.08187,25.22);(96.08187,25.22);(96.08187,25.22);(96.08187,25.22);(138.05605,15.05);(138.05605,15.05);(138.05605,15.05);(138.05605,15.05);(138.05605,15.05);(138.05605,15.05);(138.05605,15.05)
Predicted LC-MS/MS	Not Available	Positive	low	View Spectrum	(44.04948,6.21);(96.08078,27.02);(96.08078,27.02);(96.08078,27.02);(96.08078,27.02);(124.07569,13.28);(124.07569,13.28);(124.07569,13.28);(124.07569,13.28);(124.07569,13.28);(124.07569,13.28);(138.09134,9.53);(138.09134,9.53);(138.09134,9.53);(138.09134,9.53);(138.09134,9.53);(156.10191,100.0);(156.10191,100.0);(156.10191,100.0);(156.10191,100.0);(156.10191,100.0);(156.10191,100.0);(156.10191,100.0)
Predicted LC-MS/MS	Not Available	Positive	medium	View Spectrum	(42.03383,6.22);(44.04948,27.12);(53.03858,11.16);(58.06513,12.08);(58.06513,12.08);(67.05423,27.4);(70.06513,5.84);(70.06513,5.84);(81.03349,23.18);(81.03349,23.18);(81.03349,23.18);(94.06513,9.99);(94.06513,9.99);(94.06513,9.99);(94.06513,9.99);(95.04914,13.97);(95.04914,13.97);(95.04914,13.97);(96.08078,51.47);(96.08078,51.47);(96.08078,51.47);(96.08078,51.47);(98.09643,10.72);(98.09643,10.72);(98.09643,10.72);(98.09643,10.72);(99.04406,11.05);(99.04406,11.05);(113.05971,12.1);(113.05971,12.1);(124.07569,100.0);(124.07569,100.0);(124.07569,100.0);(124.07569,100.0);(124.07569,100.0);(124.07569,100.0);(125.05971,5.98);(127.07536,11.38);(138.09134,36.56);(138.09134,36.56);(138.09134,36.56);(138.09134,36.56);(138.09134,36.56);(156.10191,63.06);(156.10191,63.06);(156.10191,63.06);(156.10191,63.06);(156.10191,63.06);(156.10191,63.06);(156.10191,63.06)
Predicted LC-MS/MS	Not Available	Positive	high	View Spectrum	(39.02293,12.02);(42.03383,11.46);(44.04948,100.0);(53.00219,7.62);(53.03858,18.98);(56.04948,8.73);(58.06513,7.72);(58.06513,7.72);(67.05423,22.77);(81.03349,8.1);(81.03349,8.1);(81.03349,8.1);(94.06513,20.34);(94.06513,20.34);(94.06513,20.34);(94.06513,20.34);(96.08078,72.82);(96.08078,72.82);(96.08078,72.82);(96.08078,72.82);(124.07569,19.14);(124.07569,19.14);(124.07569,19.14);(124.07569,19.14);(124.07569,19.14);(124.07569,19.14);(154.08626,44.7);(154.08626,44.7);(154.08626,44.7);(154.08626,44.7)

Food Sources

	Name	Group
	Areca nut	Nuts	Publications	Show

Food Sources of its Food Phytochemical(s)

	Food Phytochemical	Food Source	Food Source Group
	Arecoline	Areca nut	Nuts	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
	Arecoline		Arecoline	human	saliva, urine	unchanged	1h-3h	Not Available	<1%	C₈H₁₃NO₂	155.094628663		Publications

Inter-Individual Variations in Metabolism

	Food Phytochemical		Metabolite	Effect	Value

Back

Showing entry for Arecoline