Bovine Metabolome Database: Showing metabocard for Indoleacetic acid (BMDB0000197)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:26:36 UTC

Update Date

2020-05-11 20:43:32 UTC

BMDB ID

BMDB0000197

Secondary Accession Numbers

BMDB00197

Metabolite Identification

Common Name

Indoleacetic acid

Description

Indoleacetic acid, also known as indoleacetate, belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring. Indoleacetic acid is a weakly acidic compound (based on its pKa). indoleacetic acid can be biosynthesized from indoleacetaldehyde through the action of the enzyme aldehyde dehydrogenase, mitochondrial. In cattle, indoleacetic acid is involved in the metabolic pathway called the tryptophan metabolism pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Indoleacetate	Generator
INDOLE-2-acetate	Generator
2-(1H-indol-2-yl)Acetate	Generator

Chemical Formula

C₁₀H₉NO₂

Average Molecular Weight

175.184

Monoisotopic Molecular Weight

175.063328537

IUPAC Name

2-(1H-indol-2-yl)acetic acid

Traditional Name

1H-indol-2-ylacetic acid

CAS Registry Number

Not Available

SMILES

OC(=O)CC1=CC2=CC=CC=C2N1

InChI Identifier

InChI=1S/C10H9NO2/c12-10(13)6-8-5-7-3-1-2-4-9(7)11-8/h1-5,11H,6H2,(H,12,13)

InChI Key

QOPBEBWGSGFROG-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolyl carboxylic acids and derivatives

Direct Parent

Indolyl carboxylic acids and derivatives

Alternative Parents

Substituents

Indolyl carboxylic acid derivative
Indole
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm
Mitochondria

Physical Properties

State

Solid

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	1.78	ALOGPS
logP	1.63	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	4.65	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	2	ChemAxon
Refractivity	48.33 m³·mol⁻¹	ChemAxon
Polarizability	18.14 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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-003r-2900000000-f64315153796a5741a9c	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 (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-f75ef2aedd2a3d4b6cd4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0900000000-7523e130883e327833ea	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900000000-9ba80a55406aebca2c38	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-49a0d4b911f4f404483d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05ai-0900000000-d71d809d188f10b025aa	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-053r-0900000000-3579dbfbc3e8511d5c35	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-057i-0900000000-a7c17efaf94b444d90dd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0900000000-49e666ab879885e73540	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0043-5900000000-66412efc14b953218d75	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0089-0900000000-e109c5fa0e278755a4b5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a59-0900000000-e93ec64d3fa17a7efc7c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0zi0-0900000000-faaf36dd1d5883e45f27	View in MoNA

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria

Biospecimen Locations

Brain
Fibroblasts
Kidney
Liver
Placenta
Platelet

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Brain	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Kidney	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Platelet	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Indole-3-acetic acid

METLIN ID

Not Available

PubChem Compound

4371752

PDB ID

Not Available

ChEBI ID

Not Available

References

Synthesis Reference

Snyder, H. R.; Pilgrim, Frederick J. Preparation of 3-indoleacetic acid; new synthesis of tryptophol. Journal of the American Chemical Society (1948), 70 3770-1.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Indoleacetic acid (BMDB0000197)

Structure for BMDB0000197 (Indoleacetic acid)