AFCDB: Indole-beta-carboxylic acid (FDB000935)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:46 UTC

Update date

2019-11-26 02:55:39 UTC

Primary ID

FDB000935

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Indole-beta-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. Indole-3-carboxylic acid is a weakly acidic compound (based on its pKa). Indole-3-carboxylic acid has been detected, but not quantified in, several different foods, such as barley, brussel sprouts, wakames, broccoli, and cucumbers. This could make indole-3-carboxylic acid a potential biomarker for the consumption of these foods.

CAS Number

771-50-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted 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

Chemical Formula

C9H7NO2

IUPAC name

1H-indole-3-carboxylic acid

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

Isomeric SMILES

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

Average Molecular Weight

161.1574

Monoisotopic Molecular Weight

161.047678473

Classification

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

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Animal

Plant:

Biological location:

Biofluid and excreta:

Feces

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 67.08%; H 4.38%; N 8.69%; O 19.86%	DFC
Melting Point	Mp 210-218° (198-200°)	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	1.99	HANSCH,C ET AL. (1995)
Experimental pKa	pKa2 15.59 (25°,NH)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Indole-beta-carboxylic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03xu-0900000000-cc599488e0b8dc7f1a65	Spectrum
Predicted GC-MS	Indole-beta-carboxylic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00xu-9640000000-dff74635f047e367f224	Spectrum
Predicted GC-MS	Indole-beta-carboxylic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

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

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Spectrum