Milk Composition Database: Showing metabocard for 5-Methoxyindoleacetate (BMDB0004096)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:07:55 UTC

Update Date

2020-05-21 16:28:50 UTC

MCDB ID

BMDB0004096

Secondary Accession Numbers

BMDB04096

Metabolite Identification

Common Name

5-Methoxyindoleacetate

Description

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-Methoxyindoleacetate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 5-Methoxyindoleacetate exists in all living organisms, ranging from bacteria to humans. 5-Methoxyindoleacetate and S-adenosylhomocysteine can be biosynthesized from 5-hydroxyindoleacetic acid and S-adenosylmethionine through the action of the enzyme acetylserotonin O-methyltransferase. In cattle, 5-methoxyindoleacetate is involved in the metabolic pathway called the tryptophan metabolism pathway.

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 )

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	1.76	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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-001i-1492000000-4bb4e49122eeca577f6f	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-001i-1492000000-4bb4e49122eeca577f6f	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-001i-0491000000-3833b4bbd544be9889d4	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0bvl-1910000000-c1f37125fc3b608af61f	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-5090000000-de75a303e99011a4be34	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0f6x-0950000000-b35cb5918f36be3e1ed9	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udl-0900000000-4ecf8c9d3192ce786ee1	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0900000000-8aed7fec3a54d7bd49ce	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udl-2900000000-d7b7a09d3453a1048a14	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-5900000000-de21476dd6d423ce7637	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a4i-0190000000-30a337d0188ca2b01e98	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-03di-0900000000-e29f13bccd0ff61f4d73	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-03di-0900000000-27318e117029d4756f51	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-02u1-0900000000-fc96484038377a19704e	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-1900000000-b5ca37dc8dd19df79bca	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-7900000000-ceb8e6c122bb9a4d3fbb	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0002-1910000000-8fd2478b70c897657b7f	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0002-1900000000-7fd87377f29173005ec3	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-9700000000-a4cf39ea98f467ad9511	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-9200000000-db11b5a046b68c168da7	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-05n1-9100000000-0ff3c25c94ca7b6e75da	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-03di-0900000000-0c8ed04608a5330c9d3a	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-014i-7900000000-95cba07fd384f9f59f79	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014i-1900000000-23403ec6bee04579f899	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0920000000-a3ced0adb5929f6c9416	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dr-0900000000-24447a7e06d2aa011318	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0hjj-1900000000-2026293826cbb03562de	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0w29-0790000000-8c87e508e08c958691a7	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0w2i-0940000000-0373da6c43af5609fec7	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052o-1900000000-44a6d63553f83a5e7004	2017-09-01	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		PMID: 26686724	details

External Links

HMDB ID

HMDB0004096

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023312

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Not Available

METLIN ID

PubChem Compound

PDB ID

ChEBI ID

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Hagi T, Kobayashi M, Nomura M: Metabolome analysis of milk fermented by gamma-aminobutyric acid-producing Lactococcus lactis. J Dairy Sci. 2016 Feb;99(2):994-1001. doi: 10.3168/jds.2015-9945. Epub 2015 Dec 10. [PubMed:26686724 ]

Showing metabocard for 5-Methoxyindoleacetate (BMDB0004096)

Structure for BMDB0004096 (5-Methoxyindoleacetate)