ChemFOnt: Showing chemical card for 5-Methoxyindoleacetate (CFc000002057)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:50 UTC

Chemfont ID

CFc000002057

Molecule Identification

Common Name

5-Methoxyindoleacetate

Definition

5-Methoxyindoleacetate, also known as 5-methoxy-IAA or 5-MIAA, belongs to the class of organic compounds known as indole-3-acetic acid derivatives. Indole-3-acetic acid derivatives are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole. 5-Methoxyindoleacetic acid is formed through oxidative deamination. It is identified in the urine, and the concentration is determined to be 1.3 µg/mL using GC-MS (PMID: 12908946 ). An increase in urinary 5-MIAA excretion was shown in patients with cancer of the stomach, rectum, and lung (PMID: 2446428 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-(5-Methoxy-1H-indol-3-yl)ethanoic acid	ChEBI
2-(5-Methoxyindole-3-yl)acetic acid	ChEBI
5-Methoxyindol-3-ylacetic acid	ChEBI
5-Methoxyindoleacetic acid	ChEBI
2-(5-Methoxy-1H-indol-3-yl)ethanoate	Generator
2-(5-Methoxyindole-3-yl)acetate	Generator
5-Methoxyindol-3-ylacetate	Generator
5-Methoxyindole-3-acetate	HMDB
5-Methoxyindole-3-acetic acid	HMDB, MeSH
Methoxyindoleacetate	HMDB
Methoxyindoleacetic acid	HMDB
5-Methoxy-1H-indole-3-acetic acid	HMDB
(5-Methoxy-1H-indol-3-yl)acetic acid	HMDB
2-(5-Methoxy-1H-indol-3-yl)acetic acid	HMDB
2-(5-Methoxy-3-indolyl)acetic acid	HMDB
5-Methoxy-3-indoleacetic acid	HMDB
5-Methoxy-3-indolylacetic acid	HMDB
5-Methoxy-IAA	HMDB
5-Methyloxyindole-3-acetic acid	HMDB
5-MIAA	HMDB

Chemical Formula

C₁₁H₁₁NO₃

Average Molecular Weight

205.2099

Monoisotopic Molecular Weight

205.073893223

IUPAC Name

2-(5-methoxy-1H-indol-3-yl)acetic acid

Traditional Name

5-methoxyindole-3-acetic acid

CAS Registry Number

3471-31-6

SMILES

COC1=CC2=C(NC=C2CC(O)=O)C=C1

InChI Identifier

InChI=1S/C11H11NO3/c1-15-8-2-3-10-9(5-8)7(6-12-10)4-11(13)14/h2-3,5-6,12H,4H2,1H3,(H,13,14)

InChI Key

COCNDHOPIHDTHK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indole-3-acetic acid derivatives. Indole-3-acetic acid derivatives are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolyl carboxylic acids and derivatives

Direct Parent

Indole-3-acetic acid derivatives

Alternative Parents

Substituents

Indole-3-acetic acid derivative
3-alkylindole
Indole
Anisole
Alkyl aryl ether
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Azacycle
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indole-3-acetic acids (CHEBI:28281 )
a small molecule (CPD-12020 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Saliva (HMDB: HMDB0004096)

Excreta

Biofluid or Excreta

Feces (PMID: 27786174)

Cellular substructure

Cytoplasm (HMDB: HMDB0004096)

Source

Endogenous

Endogenous (HMDB: HMDB0004096)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tryptophan Metabolism (PathBank: SMP0063693)
Tryptophan Metabolism (HMDB: HMDB0004096)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.7 g/L	ALOGPS
logP	1.76	ALOGPS
logP	1.55	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	4.3	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.32 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	54.92 m³·mol⁻¹	ChemAxon
Polarizability	20.73 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon