PhytoHub: Showing entry for Indole-3-carbinol

Indole-3-carbinol

Identification

PhytoHub ID

PHUB002320

Name

Indole-3-carbinol

Systematic Name

1H-indol-3-ylmethanol

Synonyms

1H-indol-3-ylmethanol
3-hydroxymethylindole
3-indolylcarbinol
indole-3-methanol

CAS Number

700-06-1

Average Mass

147.177

Monoisotopic Mass

147.068413914

Chemical Formula

C₉H₉NO

IUPAC Name

(1H-indol-3-yl)methanol

InChI Key

IVYPNXXAYMYVSP-UHFFFAOYSA-N

InChI Identifier

InChI=1S/C9H9NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-5,10-11H,6H2

SMILES

OCC1=CNC2=CC=CC=C12

Structure

Similar Structures

Calculated Properties

Solubility (ALOGPS): 3.75e+00 g/l
LogS (ALOGPS): -1.59
LogP (ALOGPS): 1.66
Hydrogen Acceptors: 1
Hydrogen Donors: 2
Rotatable Bond Count: 1
Polar Surface Area: 36.019999999999996
Refractivity: 43.96039999999999
Polarizability: 15.86753202927834
Formal Charge: 0
Physiological Charge: 0
pKa (strongest basic): -2.7165363605434028
pKa (strongest acidic): 15.095988794293698
Number of Rings: 2
Rule of Five: Yes
Bioavailability: Yes
Ghose Filter: No
Veber's Rule: Yes
MDDR-like Rule: No

External Links

PubChem: 3712
ChEBI: 24814

Taxonomy as Food Phytochemical

Family: N-containing compounds
Class: Miscellaneous N-containing compounds
Sub-class: Miscellaneous N-containing compounds

Taxonomy as Metabolite

Metabolite Family: N-containing compound metabolites
Metabolite Class: Glucosinolate and isothiocyanate metabolites
Metabolite Sub-class: Not Available

Taxonomy of its Food Phytochemical Precursor(s)

Food Phytochemical	Family	Class	Sub-class
Broccoli glucosinolates	N-containing compounds	Glucosinolates	Not Available	Show Food Phytochemical
Kale and daikon radish glucosinolates	N-containing compounds	Glucosinolates	Not Available	Show Food Phytochemical
Glucobrassicin	N-containing compounds	Glucosinolates	Not Available	Show Food Phytochemical

Classyfire Taxonomy

Kingdom Name: Organic compounds
Class: Indoles and derivatives
Super-class: Organoheterocyclic compounds
Sub-class: Indoles
Direct Parent Name: 3-alkylindoles
Alternative Parent Names: ["Aromatic alcohols", "Azacyclic compounds", "Benzenoids", "Heteroaromatic compounds", "Hydrocarbon derivatives", "Organonitrogen compounds", "Organopnictogen compounds", "Primary alcohols", "Substituted pyrroles"]
External Descriptor Annotations: ["an indole-phytolexin", "indolyl alcohol"]
Substituent Names: ["3-alkylindole", "Alcohol", "Aromatic alcohol", "Aromatic heteropolycyclic compound", "Azacycle", "Benzenoid", "Heteroaromatic compound", "Hydrocarbon derivative", "Organic nitrogen compound", "Organic oxygen compound", "Organonitrogen compound", "Organooxygen compound", "Organopnictogen compound", "Primary alcohol", "Pyrrole", "Substituted pyrrole"]

Spectra from Phytohub

Spectrum Type	Instrument Type	Ion Mode	Collision Energy Level	View	Peaks

Predicted GC-MS	GC-MS	Positive	Not Available	View Spectrum	(31.01783932,1.255437688);(39.02292522,1.950369084);(90.04639902,1.295822111);(93.02091252,2.815790959);(93.05729682,1.400478864);(95.03656172,1.256488245);(105.0209125,1.965067285);(106.0287371,1.814661091);(107.0365617,1.449230877);(116.0256639,1.55685043);(117.0209125,2.46097338);(117.0334885,1.312606107);(117.0572968,11.96366782);(118.0287371,1.710027773);(118.0413131,2.34854611);(118.0651214,2.936024735);(119.0365617,4.381123388);(119.0491377,3.389146714);(119.072946,4.311455831);(120.0569623,4.376570665);(121.0522109,2.517344715);(121.0647869,1.464653657);(122.0600355,1.241355092);(129.0572968,6.799819929);(130.0413131,1.368568778);(130.0651214,3.748049257);(131.0365617,4.208646119);(132.0443863,5.132911058);(146.0600355,3.224474387);(147.0678601,12.96739054);(148.0710368,1.376447307)
Predicted GC-MS	GC-MS	Positive	Not Available	View Spectrum	(39.02292522,0.8542906104);(57.01550142,0.8940249927);(59.03115062,1.921903241);(71.03115062,2.525665621);(73.01041552,0.9833063686);(73.04679982,13.81127746);(74.04796012,1.181779032);(74.05462442,1.888085703);(75.02606472,2.58731832);(75.06244902,2.757970685);(89.04171392,4.906780378);(90.04953852,1.076162875);(91.05736312,1.776970595);(103.0573631,0.9140814324);(117.0572968,1.477547638);(118.0651214,1.010980893);(129.0572968,1.269339035);(130.0651214,7.430741318);(131.06829,0.7848489929);(146.0600355,2.403267663);(147.0678601,1.360243813);(148.0756847,1.486947092);(176.0526117,0.9075494219);(191.0760855,1.311591067);(191.0886615,0.7611277329);(192.0964861,0.9555361752);(203.0760855,1.836989084);(204.0839101,7.031849703);(205.0861064,1.265163736);(218.0995593,1.028884355);(219.1073839,2.263424631)
Predicted GC-MS	GC-MS	Ei	Not Available	View Spectrum	(31.01783932,0.9368843347);(39.02292522,1.151807426);(93.02091252,1.554594219);(93.05729682,1.543189154);(95.03656172,0.8208794391);(103.0416476,1.060500731);(104.0494722,1.011309573);(105.0209125,1.429598213);(105.0572968,1.047256143);(106.0287371,1.362355872);(107.0365617,1.061119525);(116.0256639,0.8949190363);(117.0209125,1.705244674);(117.0572968,8.594043688);(118.0287371,1.144289325);(118.0413131,0.9772057962);(118.0651214,2.456053337);(119.0365617,3.035264823);(119.0491377,1.809631712);(119.072946,3.217471856);(120.0569623,2.096664133);(121.0522109,1.720690234);(122.0600355,0.8301904783);(129.0572968,6.264953045);(130.0651214,3.287079422);(131.0365617,3.060274757);(132.0443863,3.711304296);(145.0522109,1.142262002);(146.0600355,1.97533231);(147.0678601,10.19603788);(148.0710368,1.082277027)
Predicted GC-MS	GC-MS	Ei	Not Available	View Spectrum	(31.01783932,0.9368843347);(39.02292522,1.151807426);(93.02091252,1.554594219);(93.05729682,1.543189154);(95.03656172,0.8208794391);(103.0416476,1.060500731);(104.0494722,1.011309573);(105.0209125,1.429598213);(105.0572968,1.047256143);(106.0287371,1.362355872);(107.0365617,1.061119525);(116.0256639,0.8949190363);(117.0209125,1.705244674);(117.0572968,8.594043688);(118.0287371,1.144289325);(118.0413131,0.9772057962);(118.0651214,2.456053337);(119.0365617,3.035264823);(119.0491377,1.809631712);(119.072946,3.217471856);(120.0569623,2.096664133);(121.0522109,1.720690234);(122.0600355,0.8301904783);(129.0572968,6.264953045);(130.0651214,3.287079422);(131.0365617,3.060274757);(132.0443863,3.711304296);(145.0522109,1.142262002);(146.0600355,1.97533231);(147.0678601,10.19603788);(148.0710368,1.082277027)
LC-MS/MS	Quattro_QQQ	Positive	low	View Spectrum	(90.0,66.466);(91.0,21.772);(92.0,9.204);(119.0,100.0);(120.0,77.091);(147.0,82.9);(148.0,67.687);(149.0,6.812)
LC-MS/MS	Quattro_QQQ	Positive	med	View Spectrum	(64.0,40.645);(65.0,42.262);(76.0,10.324);(77.0,10.967);(90.0,100.0);(91.0,44.603);(92.0,9.854);(93.0,4.946);(104.0,9.078);(132.0,5.099)
LC-MS/MS	Quattro_QQQ	Positive	high	View Spectrum	(50.0,15.454);(64.0,100.0);(65.0,19.685);(76.0,32.68);(77.0,32.643);(91.0,16.055)
LC-MS/MS	LC-ESI-QTOF	positive	Not Available	View Spectrum	(77.037,0.36248);(103.056,2.64095);(128.048,0.56962);(130.063,100.0)
LC-MS/MS	LC-ESI-QTOF	positive	Not Available	View Spectrum	(51.027,0.98058);(77.038,58.19348);(95.05,9.25891);(101.04,0.43372);(102.045,3.03602);(103.056,66.56609);(104.046,0.56572);(105.047,2.92287);(128.048,9.78691);(129.047,0.73543);(130.063,100.0)
LC-MS/MS	LC-ESI-QTOF	positive	Not Available	View Spectrum	(50.017,0.42486);(51.024,13.97785);(53.04,0.52404);(63.023,0.26251);(75.023,0.90078);(77.038,100.0);(78.036,0.43075);(91.05,0.23403);(95.05,12.98803);(101.041,0.7584);(102.048,4.57527);(103.056,19.45554);(104.05,0.31292);(105.045,4.37855);(119.049,0.21145);(128.05,2.55178);(129.047,0.67362);(130.063,8.49328)
LC-MS/MS	Not Available	Positive	Not Available	View Spectrum	(51.02326,3.31);(77.03736,9.94);(89.03912,6.62);(94.06475,9.94);(103.05156,9.94);(106.06502,100.0);(118.06467,3.31);(130.06142,13.25);(148.07635,26.26)
LC-MS/MS	LC-ESI-Q	Positive	high	View Spectrum	(94.066,0.024);(106.065,0.238);(120.081,0.029);(130.065,0.105);(148.076,1.0)
LC-MS/MS	LC-ESI-QTOF	Positive	medium	View Spectrum	(51.023,0.033);(77.037,0.099);(89.039,0.066);(94.065,0.099);(103.052,0.099);(106.065,1.0);(118.065,0.033);(130.061,0.132);(148.064,0.033);(148.076,0.263)
Predicted LC-MS/MS	Not Available	Positive	low	View Spectrum	(31.01838972,0.0244051345);(41.03912516,0.0706985542);(51.0234751,0.0384388182);(52.01872406,0.0008267131);(53.03912516,0.0338676141);(55.05477522,0.0075216517);(65.03912516,0.000004798);(66.03437413,0.0000944542);(79.05477522,0.0036407764);(80.05002419,0.0031579629);(81.03403978,0.0000062821);(81.07042529,0.0059879166);(90.03437413,0.0000682656);(92.05002419,0.0025222492);(94.02928875,0.0330306409);(96.04493881,0.0566924388);(98.06058888,0.0074815097);(103.0547752,0.0738774686);(104.0500242,0.0134094644);(106.0656743,0.0100081222);(108.0449388,0.0688648454);(116.0500242,0.5283737759);(118.0292887,0.0040379573);(118.0656743,0.1741943974);(119.0496898,0.1096362749);(120.0449388,0.0377458737);(121.0653399,0.0546192693);(122.0605889,0.061094615);(130.0656743,47.41457865);(132.0449388,0.1669095288);(148.0762389,50.99420398)
Predicted LC-MS/MS	Not Available	Positive	med	View Spectrum	(31.01838972,0.0797654448);(41.03912516,0.0799678289);(51.0234751,0.034939837);(52.01872406,0.0047752548);(53.03912516,0.0095183245);(55.05477522,0.0077428198);(65.03912516,0.0033862731);(66.03437413,0.0020834709);(79.05477522,0.3242663328);(80.05002419,0.0201950913);(81.03403978,0.0004779347);(81.07042529,0.0537068078);(90.03437413,0.0030735691);(92.05002419,0.3038706168);(94.02928875,0.0574948463);(96.04493881,0.0552021997);(98.06058888,0.0048252481);(103.0547752,3.421637494);(104.0500242,0.2845405784);(106.0656743,0.2166430477);(108.0449388,0.042248128);(116.0500242,1.580509824);(118.0292887,0.0397475227);(118.0656743,3.000749433);(119.0496898,1.361335442);(120.0449388,0.4420499057);(121.0653399,2.476750695);(122.0605889,0.5356090467);(130.0656743,64.79077549);(132.0449388,0.6279258875);(148.0762389,20.13418561)
Predicted LC-MS/MS	Not Available	Positive	high	View Spectrum	(31.01838972,0.2310487613);(41.03912516,0.4696761507);(51.0234751,2.131034042);(52.01872406,0.200523694);(53.03912516,0.3023192313);(55.05477522,0.1509453901);(65.03912516,0.1515401919);(66.03437413,0.1610086095);(79.05477522,1.243715472);(80.05002419,1.057068771);(81.03403978,0.1219099822);(81.07042529,1.103960068);(90.03437413,0.1632547034);(92.05002419,0.0277091282);(94.02928875,0.473249205);(96.04493881,0.502221969);(98.06058888,0.1152374736);(103.0547752,19.79910943);(104.0500242,4.175495286);(106.0656743,0.491376952);(108.0449388,0.3783907989);(116.0500242,1.649085212);(118.0292887,0.170903724);(118.0656743,0.771986603);(119.0496898,1.224627146);(120.0449388,0.8607917198);(121.0653399,0.3282745816);(122.0605889,0.7596540514);(130.0656743,55.9724695);(132.0449388,3.894255256);(148.0762389,0.9171568916)
Predicted LC-MS/MS	Not Available	Negative	low	View Spectrum	(17.00273965,0.659257443);(29.00273965,0.2558811849);(31.01838972,0.0710464448);(41.00273965,0.0000500524);(50.003074,0.0003302368);(51.0234751,0.0009805398);(64.01872406,0.0116373106);(65.99798862,0.0031976513);(66.03437413,0.0011374769);(68.01363868,0.0067608488);(77.03912516,0.0059997769);(78.03437413,0.0044887274);(88.01872406,0.0037388149);(90.03437413,0.0295474479);(92.01363868,0.0091834426);(92.05002419,0.0207643097);(94.02928875,0.069578502);(96.04493881,0.0106780522);(101.0391252,0.01127106);(102.0343741,0.001376991);(104.0500242,0.2012061558);(114.0343741,0.6182120276);(116.0136387,0.0030885529);(116.0500242,20.61601228);(117.0340398,0.0453089686);(118.0292887,0.0215996642);(119.0496898,0.0452142622);(120.0449388,0.1653637578);(128.0500242,12.44345603);(130.0292887,0.2669742515);(146.0605889,64.39665774)
Predicted LC-MS/MS	Not Available	Negative	med	View Spectrum	(17.00273965,0.8986844796);(29.00273965,0.1076570217);(31.01838972,0.0409860194);(41.00273965,0.0015814461);(50.003074,0.0137643642);(51.0234751,0.0043011803);(64.01872406,0.0386641231);(65.99798862,0.0086870856);(66.03437413,0.0255979857);(68.01363868,0.1031152133);(77.03912516,0.0025382138);(78.03437413,0.0026543816);(88.01872406,0.1603857628);(90.03437413,0.6807983692);(92.01363868,0.0160025747);(92.05002419,0.0669509803);(94.02928875,0.04295079);(96.04493881,0.0192497128);(101.0391252,0.1592061348);(102.0343741,0.0165858684);(104.0500242,0.0315200939);(114.0343741,2.925489383);(116.0136387,0.060335376);(116.0500242,62.69111681);(117.0340398,0.2887206405);(118.0292887,0.1700756595);(119.0496898,0.2960501432);(120.0449388,0.2417778918);(128.0500242,10.75706129);(130.0292887,0.6675051165);(146.0605889,19.45998588)
Predicted LC-MS/MS	Not Available	Negative	high	View Spectrum	(17.00273965,0.5104463034);(29.00273965,0.7096322569);(31.01838972,0.1449216234);(41.00273965,0.2394748747);(50.003074,0.211538199);(51.0234751,0.1565547355);(64.01872406,2.140725717);(65.99798862,0.2758723194);(66.03437413,1.729904868);(68.01363868,0.5250464106);(77.03912516,0.6532803024);(78.03437413,0.0518814033);(88.01872406,2.642160178);(90.03437413,5.805922231);(92.01363868,0.3168979722);(92.05002419,1.396743155);(94.02928875,0.2369751208);(96.04493881,0.1351341623);(101.0391252,0.3428848465);(102.0343741,0.0684624307);(104.0500242,1.40671332);(114.0343741,7.468515668);(116.0136387,0.2224173624);(116.0500242,62.52042425);(117.0340398,0.1824273274);(118.0292887,1.352954456);(119.0496898,0.1645219622);(120.0449388,1.734907415);(128.0500242,2.855259311);(130.0292887,1.627198583);(146.0605889,2.170201235)
Predicted LC-MS/MS	Not Available	Negative	low	View Spectrum	(116.05057,96.21);(116.05057,96.21);(116.05057,96.21);(116.05057,96.21);(116.05057,96.21);(116.05057,96.21);(116.05057,96.21);(116.05057,96.21);(116.05057,96.21);(128.05057,55.24);(128.05057,55.24);(128.05057,55.24);(146.06114,100.0);(146.06114,100.0);(146.06114,100.0);(146.06114,100.0);(146.06114,100.0);(146.06114,100.0);(146.06114,100.0);(146.06114,100.0);(146.06114,100.0)
Predicted LC-MS/MS	Not Available	Negative	medium	View Spectrum	(116.05057,100.0);(116.05057,100.0);(116.05057,100.0);(116.05057,100.0);(116.05057,100.0);(116.05057,100.0);(116.05057,100.0);(116.05057,100.0);(116.05057,100.0);(128.05057,26.62);(128.05057,26.62);(128.05057,26.62)
Predicted LC-MS/MS	Not Available	Negative	high	View Spectrum	(116.05057,100.0);(116.05057,100.0);(116.05057,100.0);(116.05057,100.0);(116.05057,100.0);(116.05057,100.0);(116.05057,100.0);(116.05057,100.0);(116.05057,100.0)
Predicted LC-MS/MS	Not Available	Positive	low	View Spectrum	(130.06513,100.0);(130.06513,100.0);(130.06513,100.0);(130.06513,100.0);(130.06513,100.0);(130.06513,100.0);(130.06513,100.0);(130.06513,100.0);(130.06513,100.0);(146.06004,16.17);(146.06004,16.17);(146.06004,16.17);(146.06004,16.17);(146.06004,16.17);(146.06004,16.17);(148.07569,25.29);(148.07569,25.29);(148.07569,25.29);(148.07569,25.29);(148.07569,25.29);(148.07569,25.29);(148.07569,25.29);(148.07569,25.29);(148.07569,25.29);(148.07569,25.29)
Predicted LC-MS/MS	Not Available	Positive	medium	View Spectrum	(79.05423,20.71);(79.05423,20.71);(104.04948,30.94);(104.04948,30.94);(104.04948,30.94);(104.04948,30.94);(104.04948,30.94);(104.04948,30.94);(104.04948,30.94);(104.04948,30.94);(104.04948,30.94);(130.06513,100.0);(130.06513,100.0);(130.06513,100.0);(130.06513,100.0);(130.06513,100.0);(130.06513,100.0);(130.06513,100.0);(130.06513,100.0);(130.06513,100.0)
Predicted LC-MS/MS	Not Available	Positive	high	View Spectrum	(43.01784,23.6);(65.03858,40.51);(77.03858,100.0);(79.05423,47.45);(79.05423,47.45);(91.05423,19.51);(92.04948,25.31);(92.04948,25.31);(92.04948,25.31);(92.04948,25.31);(92.04948,25.31);(92.04948,25.31);(101.03858,25.87);(103.05423,59.89);(104.04948,76.03);(104.04948,76.03);(104.04948,76.03);(104.04948,76.03);(104.04948,76.03);(104.04948,76.03);(104.04948,76.03);(104.04948,76.03);(104.04948,76.03);(116.04948,39.4);(116.04948,39.4);(116.04948,39.4);(116.04948,39.4);(116.04948,39.4);(116.04948,39.4);(116.04948,39.4);(116.04948,39.4);(128.04948,17.48);(128.04948,17.48);(128.04948,17.48);(128.04948,17.48);(128.04948,17.48);(128.04948,17.48);(128.04948,17.48);(130.06513,35.84);(130.06513,35.84);(130.06513,35.84);(130.06513,35.84);(130.06513,35.84);(130.06513,35.84);(130.06513,35.84);(130.06513,35.84);(130.06513,35.84);(146.06004,35.14);(146.06004,35.14);(146.06004,35.14);(146.06004,35.14);(146.06004,35.14);(146.06004,35.14)

Food Sources

Name	Group
Broccoli	Vegetables, Cabbages	Publications	Show
Cauliflower	Vegetables, Cabbages	Publications	Show
Common cabbage	Vegetables, Cabbages	Publications	Show

Food Sources of its Food Phytochemical(s)

Food Phytochemical	Food Source	Food Source Group
Glucobrassicin	Broccoli	Vegetables, Cabbages	Publications	Show
Glucobrassicin	Brussel sprouts	Vegetables, Cabbages	Publications	Show
Glucobrassicin	Cabbage, White	Vegetables, Cabbages	Publications	Show
Glucobrassicin	Cabbage, red	Vegetables, Cabbages	Publications	Show
Glucobrassicin	Capers	Herbs and Spices	Publications	Show
Glucobrassicin	Cauliflower	Vegetables, Cabbages	Publications	Show
Glucobrassicin	Kale	Vegetables, Cabbages	Publications	Show
Glucobrassicin	Mustard	Condiments and seasonings	Publications	Show
Glucobrassicin	Radish	Vegetables, Root vegetables	Publications	Show
Glucobrassicin	Swede (Rutabaga)	Vegetables, Root vegetables	Publications	Show
Glucobrassicin	Turnip	Vegetables, Root vegetables	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
Indole-3-carbinol	3,3′-Diindolylmethane	human	urine	Not Available	Not Available	Not Available	Not Available	C₁₇H₁₄N₂	246.115698459	Detailed Intervention Studies
Indole-3-carbinol	Ascorbigen	human	urine	Not Available	Not Available	Not Available	Not Available	C₁₅H₁₅NO₆	305.089937207		Publications
Indole-3-carbinol	Indole-3-carboxaldehyde	human	urine	Not Available	Not Available	Not Available	Not Available	C₉H₇NO	145.052763849		Publications
Indole-3-carbinol	Indole-3-carboxylic acid	human	urine	Not Available	Not Available	Not Available	Not Available	C₉H₇NO₂	161.047678469		Publications
Broccoli glucosinolates	Indole-3-carbinol	Not Available	Not Available	Not Available	Not Available	Not Available	Not Available	C₉H₉NO	147.068413914	Detailed Intervention Studies
Kale and daikon radish glucosinolates	Indole-3-carbinol	Not Available	Not Available	Not Available	Not Available	Not Available	Not Available	C₉H₉NO	147.068413914	Detailed Intervention Studies
Glucobrassicin	Indole-3-carbinol	human	urine	Not Available	Not Available	Not Available	Not Available	C₉H₉NO	147.068413914		Publications

Inter-Individual Variations in Metabolism

	Food Phytochemical		Metabolite	Effect	Value

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Showing entry for Indole-3-carbinol