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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2006-05-22 15:12:50 UTC

Update Date

2023-02-21 17:16:36 UTC

HMDB ID

HMDB0003320

Secondary Accession Numbers

HMDB03320

Metabolite Identification

Common Name

Indole-3-carboxylic acid

Description

Indole-3-carboxylic acid, also known as 3-carboxyindole or 3-indolecarboxylate, belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. Indolecarboxylic acids and derivatives are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole. Naphthylmethylindoles: Any compound containing a 1H-indol-3-yl-(1-naphthyl)methane structure with substitution at the nitrogen atom of the indole ring by an alkyl, haloalkyl, alkenyl, cycloalkylmethyl, cycloalkylethyl, 1-(N-methyl-2-piperidinyl)methyl, or 2-(4-morpholinyl)ethyl group whether or not further substituted in the indole ring to any extent and whether or not substituted in the naphthyl ring to any extent. One example given is JWH-250. Outside of the human body, indole-3-carboxylic acid has been detected, but not quantified in several different foods, such as brassicas, broccoli, pulses, common beets, and barley. This could make indole-3-carboxylic acid a potential biomarker for the consumption of these foods. Notice the pentyl group substituted onto the nitrogen atom of the indole ring. Note that this definition encompasses only those compounds that have OH groups attached to both the phenyl and the cyclohexyl rings, and so does not include compounds such as O-1871 which lacks the cyclohexyl OH group, or compounds such as JWH-337 or JWH-344 which lack the phenolic OH group.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      49.460 -32.501   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      46.924 -31.672   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      47.475 -36.761   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      47.953 -32.819   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      46.017 -36.292   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      47.475 -34.282   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      46.017 -34.752   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      48.373 -35.522   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      44.684 -37.062   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      44.684 -33.982   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      43.350 -36.292   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      43.350 -34.752   0.000  0.00  0.00           C+0
CONECT    1    4                                                            
CONECT    2    4                                                            
CONECT    3    5    8                                                       
CONECT    4    1    2    6                                                  
CONECT    5    3    7    9                                                  
CONECT    6    4    7    8                                                  
CONECT    7    5    6   10                                                  
CONECT    8    3    6                                                       
CONECT    9    5   11                                                       
CONECT   10    7   12                                                       
CONECT   11    9   12                                                       
CONECT   12   10   11                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Indole-3-carboxylate	Generator
3-Carboxyindole	HMDB
1H-Indole-3-carboxylate	HMDB
1H-Indole-3-carboxylic acid	HMDB
3-Indole carboxylic acid	HMDB
3-Indolecarboxylate	HMDB
3-Indolecarboxylic acid	HMDB
3-Indoleformate	HMDB
3-Indoleformic acid	HMDB
3-Indolylcarboxylate	HMDB
3-Indolylcarboxylic acid	HMDB
Indole - 3 carboxylate	HMDB
Indole - 3 carboxylic acid	HMDB
Indole-3-carboxylicacid	HMDB
Indole-3-carboxylic acid	KEGG
Indole-b-carboxylate	Generator
Indole-b-carboxylic acid	Generator
Indole-beta-carboxylate	Generator
Indole-β-carboxylate	Generator
Indole-β-carboxylic acid	Generator

Chemical Formula

C₉H₇NO₂

Average Molecular Weight

161.1574

Monoisotopic Molecular Weight

161.047678473

IUPAC Name

1H-indole-3-carboxylic acid

Traditional Name

indole - 3 carboxylic acid

CAS Registry Number

771-50-6

SMILES

OC(=O)C1=CNC2=CC=CC=C12

InChI Identifier

InChI=1S/C9H7NO2/c11-9(12)7-5-10-8-4-2-1-3-6(7)8/h1-5,10H,(H,11,12)

InChI Key

KMAKOBLIOCQGJP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. Indolecarboxylic acids and derivatives are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolecarboxylic acids and derivatives

Direct Parent

Indolecarboxylic acids and derivatives

Alternative Parents

Substituents

Indolecarboxylic acid derivative
Indole
Pyrrole-3-carboxylic acid
Pyrrole-3-carboxylic acid or derivatives
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Vinylogous amide
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indol-3-yl carboxylic acid (CHEBI:24809 )

Ontology

Not Available

Feces (HMDB: HMDB0003320)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0003320)

Source

Exogenous

Food

Food (HMDB: HMDB0003320)

Cereal and cereal product

Cereal

Barley (FooDB: FOOD00088)

Vegetable

Cabbage

Broccoli (FooDB: FOOD00034)
Brussel sprouts (FooDB: FOOD00032)

Leaf vegetable

Common beet (FooDB: FOOD00025)

Brassica

Brassicas (FooDB: FOOD00857)

Gourd

Cucumber (FooDB: FOOD00065)

Pulse

Pea

Common pea (FooDB: FOOD00141)

Pulses (FooDB: FOOD00867)

Aquatic origin

Seaweed

Wakame (FooDB: FOOD00550)

Fruit

Pome

Pomes (FooDB: FOOD00856)

Endogenous

Plant

Animal

Animal (HMDB: HMDB0003320)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	206.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	1.99	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	124.501	30932474
[M+H]+	MetCCS_train_pos	132.367	30932474
[M-H]-	Not Available	124.501	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000356
[M+H]+	Not Available	132.357	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000356

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.42 g/L	ALOGPS
logP	1.79	ALOGPS
logP	1.73	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	3.52	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	53.09 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	44.4 m³·mol⁻¹	ChemAxon
Polarizability	15.96 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	134.003	31661259
DarkChem	[M-H]-	130.197	31661259
DeepCCS	[M-2H]-	166.11	30932474
DeepCCS	[M+Na]+	141.648	30932474
AllCCS	[M+H]+	133.6	32859911
AllCCS	[M+H-H2O]+	129.0	32859911
AllCCS	[M+NH4]+	137.9	32859911
AllCCS	[M+Na]+	139.1	32859911
AllCCS	[M-H]-	131.1	32859911
AllCCS	[M+Na-2H]-	131.7	32859911
AllCCS	[M+HCOO]-	132.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Indole-3-carboxylic acid	OC(=O)C1=CNC2=CC=CC=C12	3069.2	Standard polar	33892256
Indole-3-carboxylic acid	OC(=O)C1=CNC2=CC=CC=C12	1744.4	Standard non polar	33892256
Indole-3-carboxylic acid	OC(=O)C1=CNC2=CC=CC=C12	1933.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Indole-3-carboxylic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)C1=C[NH]C2=CC=CC=C12	1877.1	Semi standard non polar	33892256
Indole-3-carboxylic acid,1TMS,isomer #2	C[Si](C)(C)N1C=C(C(=O)O)C2=CC=CC=C21	1904.4	Semi standard non polar	33892256
Indole-3-carboxylic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CN([Si](C)(C)C)C2=CC=CC=C12	1990.2	Semi standard non polar	33892256
Indole-3-carboxylic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CN([Si](C)(C)C)C2=CC=CC=C12	1938.8	Standard non polar	33892256
Indole-3-carboxylic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CN([Si](C)(C)C)C2=CC=CC=C12	1989.5	Standard polar	33892256
Indole-3-carboxylic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=C[NH]C2=CC=CC=C12	2137.4	Semi standard non polar	33892256
Indole-3-carboxylic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=C(C(=O)O)C2=CC=CC=C21	2163.3	Semi standard non polar	33892256
Indole-3-carboxylic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2367.6	Semi standard non polar	33892256
Indole-3-carboxylic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2305.1	Standard non polar	33892256
Indole-3-carboxylic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2261.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Indole-3-carboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-03xu-0900000000-cc599488e0b8dc7f1a65	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Indole-3-carboxylic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00xu-9640000000-dff74635f047e367f224	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Indole-3-carboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-carboxylic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-03di-0900000000-104208fcdd8732ebadf0	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-carboxylic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-014l-4900000000-6b0c749e944b64d5385c	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-carboxylic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-014u-9300000000-0af5d90221e77a572181	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-carboxylic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-014i-0900000000-8c45f845ef01c19b445c	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-carboxylic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF	splash10-014l-1900000000-1c77378b797771275320	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-carboxylic acid LC-ESI-qToF , Positive-QTOF	splash10-0udi-0900000000-946741c676c658f5309f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-carboxylic acid LC-ESI-QTOF , negative-QTOF	splash10-014i-0900000000-8c45f845ef01c19b445c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-carboxylic acid LC-ESI-QTOF , positive-QTOF	splash10-02t9-0900000000-6053c6788a142676471b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-carboxylic acid LC-ESI-QTOF , positive-QTOF	splash10-014l-1900000000-1995f9dbe32f987d490a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-carboxylic acid LC-ESI-QTOF , positive-QTOF	splash10-014l-9800000000-670cc23cba665a2c274c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-carboxylic acid LC-ESI-QTOF , positive-QTOF	splash10-00ko-9100000000-933c5733f214b898f898	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-carboxylic acid LC-ESI-QTOF , positive-QTOF	splash10-03xu-0900000000-3f9d7c7294f2ea5a6c2c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-carboxylic acid LC-ESI-QTOF , positive-QTOF	splash10-014l-0900000000-a2251627ca78c6acb131	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-carboxylic acid LC-ESI-QTOF , positive-QTOF	splash10-014l-0900000000-391c26d59d3501f7004c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-carboxylic acid LC-ESI-ITFT , positive-QTOF	splash10-014i-0900000000-9af372afcef18a3b9f32	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-carboxylic acid LC-ESI-ITFT , positive-QTOF	splash10-014i-0900000000-265f90afc22f3879b03e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-carboxylic acid LC-ESI-ITFT , positive-QTOF	splash10-014i-0900000000-3e251a670db5df960fd6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-carboxylic acid LC-ESI-ITFT , positive-QTOF	splash10-014i-0900000000-ff43090393a4f119b73a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-carboxylic acid LC-ESI-QTOF , positive-QTOF	splash10-014l-1900000000-1c77378b797771275320	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-carboxylic acid 10V, Positive-QTOF	splash10-03dl-0900000000-bac7fe6d41164b57962a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-carboxylic acid 20V, Positive-QTOF	splash10-0006-0900000000-75aeec0d90802e4f4ce6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-carboxylic acid 40V, Positive-QTOF	splash10-0006-0900000000-4057c3f38ac935f3f96b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-carboxylic acid 10V, Negative-QTOF	splash10-02t9-0900000000-92711ed9a44b0be75d6b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-carboxylic acid 20V, Negative-QTOF	splash10-014i-0900000000-4f69556e7cb4da6b44d3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-carboxylic acid 40V, Negative-QTOF	splash10-014i-0900000000-c48621befefcf6da4d50	2017-09-01	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Metastatic melanoma	28923537	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Metastatic melanoma
Frankel AE, Coughlin LA, Kim J, Froehlich TW, Xie Y, Frenkel EP, Koh AY: Metagenomic Shotgun Sequencing and Unbiased Metabolomic Profiling Identify Specific Human Gut Microbiota and Metabolites Associated with Immune Checkpoint Therapy Efficacy in Melanoma Patients. Neoplasia. 2017 Oct;19(10):848-855. doi: 10.1016/j.neo.2017.08.004. Epub 2017 Sep 15. [PubMed:28923537 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Structural scheduling of synthetic cannabinoids

METLIN ID

3795

PubChem Compound

69867

PDB ID

Not Available

ChEBI ID

24809

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

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General References

Liebich HM, Forst C: Basic profiles of organic acids in urine. J Chromatogr. 1990 Jan 26;525(1):1-14. [PubMed:2338430 ]
HARTMANN F, FREIBERG E, RUGE W: [Indolepatterns in the urine of liver patients]. Klin Wochenschr. 1962 Jul 15;40:721-9. [PubMed:13905029 ]
Byrd DJ, Kochen W, Idzko D, Knorr E: The analysis of indolic tryptophan metabolites in human urine. Thin-layer chromatography and in situ quantitation. J Chromatogr. 1974 Jul 17;94(0):85-106. [PubMed:4844607 ]

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Indole-3-carboxylic acid → 3,4,5-trihydroxy-6-(1H-indole-3-carbonyloxy)oxane-2-carboxylic acid	details

Enzyme Details

2. Glycine N-acyltransferase

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:: GLYAT
Uniprot ID:: Q6IB77
Molecular weight:: 18506.33

Reactions

Indole-3-carboxylic acid → 2-{[hydroxy(1H-indol-3-yl)methylidene]amino}acetic acid	details

Showing metabocard for Indole-3-carboxylic acid (HMDB0003320)

MOL for HMDB0003320 (Indole-3-carboxylic acid)

3D MOL for HMDB0003320 (Indole-3-carboxylic acid)

3D SDF for HMDB0003320 (Indole-3-carboxylic acid)

3D-SDF for HMDB0003320 (Indole-3-carboxylic acid)

PDB for HMDB0003320 (Indole-3-carboxylic acid)

3D PDB for HMDB0003320 (Indole-3-carboxylic acid)

SMILES for HMDB0003320 (Indole-3-carboxylic acid)

INCHI for HMDB0003320 (Indole-3-carboxylic acid)

Structure for HMDB0003320 (Indole-3-carboxylic acid)

3D Structure for HMDB0003320 (Indole-3-carboxylic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions