Bovine Metabolome Database: Showing metabocard for 1H-Indole-3-carboxaldehyde (BMDB0063668)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2020-02-10 19:45:26 UTC

Update Date

2021-01-12 22:02:02 UTC

BMDB ID

BMDB0063668

Secondary Accession Numbers

BMDB63668

Metabolite Identification

Common Name

1H-Indole-3-carboxaldehyde

Description

Indole-3-carboxaldehyde (IAld or I3A), also known as 3-formylindole or 3-indolealdehyde, belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole. I3A is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, I3A is a biologically active metabolite which acts as a receptor agonist at the aryl hydrocarbon receptor in intestinal immune cells. It stimulates the production of interleukin-22 which facilitates mucosal reactivity (PMID: 27102537 ). I3A is a microbially derived tryptophan metabolite produced by Clostridium and Lactobacillus (PMID: 30120222 , 27102537 ). I3A has also been found in the urine of patients with untreated phenylketonuria (PMID: 5073866 ). Outside of the human body, I3A has been detected, but not quantified in, several different foods, such as beans, Brussels sprouts, cucumbers, cereals and cereal products, and white cabbages. This could make I3A a potential biomarker for the consumption of these foods.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
1H-Indole-3-carboxaldehyde	ChEBI
3-Formylindole	ChEBI
3-Indolealdehyde	ChEBI
3-Indolecarbaldehyde	ChEBI
3-Indolecarboxaldehyde	ChEBI
beta-Indolylaldehyde	ChEBI
I3cho	ChEBI
Indole-3-aldehyde	ChEBI
Indole-3-carbaldehyde	Kegg
b-Indolylaldehyde	Generator
Β-indolylaldehyde	Generator
3-Indolemethanal	MeSH
1H-Indole-3-carbaldehyde	HMDB
1H-Indole-3-carboxaldehde	HMDB
indol-3-Carbaldehyd	HMDB
indol-3-Carbaldehyde	HMDB
indol-3-Carboxaldehyde	HMDB
INDOLE-3-carboxyaldehyde	HMDB
Indole-3-carboxaldehyde	ChEBI
1H-Indol-3-yl carboxaldehyde	HMDB
1H-Indole-3-aldehyde	HMDB
1H-Indole-3-methanal	HMDB
3-Formyl-1H-indole	HMDB
3-Indolylformaldehyde	HMDB
I3A	HMDB
Indole-3-carboxylaldehyde	HMDB
Indole-3-formaldehyde	HMDB

Chemical Formula

C₉H₇NO

Average Molecular Weight

145.158

Monoisotopic Molecular Weight

145.052763851

IUPAC Name

1H-indole-3-carbaldehyde

Traditional Name

indole-3-carboxaldehyde

CAS Registry Number

Not Available

SMILES

O=CC1=CNC2=C1C=CC=C2

InChI Identifier

InChI=1S/C9H7NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-6,10H

InChI Key

OLNJUISKUQQNIM-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

Indoles

Alternative Parents

Substituents

Indole
Aryl-aldehyde
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Vinylogous amide
Azacycle
Aldehyde
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indoles (CHEBI:28238 )
heteroarenecarbaldehyde (CHEBI:28238 )
an indole-phytolexin (INDOLE-3-CARBOXALDEHYDE )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.92	ALOGPS
logP	1.78	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	13.54	ChemAxon
pKa (Strongest Basic)	-7.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	32.86 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	43.73 m³·mol⁻¹	ChemAxon
Polarizability	15 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00kp-7900000000-cfb69fae32949705791f	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0007-2900000000-90cfb2317bcbb908e2e8	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0007-2900000000-90cfb2317bcbb908e2e8	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0007-2900000000-c43b940db5ef735c79d6	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00kk-2950000000-8901bc9a710fac996fbc	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00kb-2960000000-0b154d6ce8924292e9ed	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9430000000-252f37d7921252e01ac0	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9430000000-868873ec5dc494bef752	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00kp-7900000000-cfb69fae32949705791f	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0007-2900000000-90cfb2317bcbb908e2e8	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0007-2900000000-90cfb2317bcbb908e2e8	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0007-2900000000-c43b940db5ef735c79d6	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00kk-2950000000-8901bc9a710fac996fbc	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00kb-2960000000-0b154d6ce8924292e9ed	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9430000000-252f37d7921252e01ac0	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9430000000-868873ec5dc494bef752	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-014j-0900000000-2f4c23a8137235ce4e95	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0006-0900000000-39d11dbd7bebe565fa94	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014l-0900000000-c9a64e9031a8d467a02b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0006-0900000000-b7ccb1c640ee7aaf06b4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014l-0900000000-d434c2e937c83d1ffd7c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00kb-0900000000-597c804d77e9a7930c9e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-2900000000-878ab4a0cfc6d8f0e9d0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00kf-9400000000-74dbc81ab5e686655977	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00kf-9100000000-22b52274e9bec85c9488	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-3900000000-b8cbcf3139ea5a313666	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-2900000000-94ec8ba0db56440ffc3f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-00kf-9400000000-baa602f27188a3041af4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-00kf-9100000000-345cf6df9ff740e5d926	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 25V, Positive	splash10-014i-2900000000-878ab4a0cfc6d8f0e9d0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-00kb-0900000000-597c804d77e9a7930c9e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0002-0900000000-3d2deb9c036b136fd16a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-014i-1900000000-16d2415d939c5aaff449	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-014l-0900000000-d434c2e937c83d1ffd7c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-014l-0900000000-c9a64e9031a8d467a02b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-00kf-0900000000-ba3a2cf1a036ce47cf69	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-68769392454e8a8bc1da	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0900000000-0be256e552c87fb9650a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-2900000000-ae05266446e712d329cb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-89f321c95d799e3073a8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0900000000-f63834b99989e7eab9cf	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-2900000000-7f76bc218a02b8adc1d0	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-0007-2900000000-fcb37c6394c016a4e2d0	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Colostrum
Muscle

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Colostrum	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Commercial Product/bacterial growth on ground beef	PMID: 22417363	details
Muscle	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Commercial Product/bacterial growth on ground beef	PMID: 22417363	details

External Links

HMDB ID

HMDB0029737

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

INDOLE-3-CARBOXALDEHYDE

BiGG ID

Not Available

Wikipedia Link

Indole-3-carboxaldehyde

METLIN ID

Not Available

PubChem Compound

10256

PDB ID

I3A

ChEBI ID

28238

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Zhang LS, Davies SS: Microbial metabolism of dietary components to bioactive metabolites: opportunities for new therapeutic interventions. Genome Med. 2016 Apr 21;8(1):46. doi: 10.1186/s13073-016-0296-x. [PubMed:27102537 ]
Kochen W, Buhner R, Otting W: [Identification of oxindole and 3-indolecarbaldehyde in the urine of patients with untreated phenylketonuria]. Hoppe Seylers Z Physiol Chem. 1972 Jul;353(7):1017-22. [PubMed:5073866 ]

Showing metabocard for 1H-Indole-3-carboxaldehyde (BMDB0063668)

Structure for BMDB0063668 (1H-Indole-3-carboxaldehyde)