5-Methoxyindoleacetate (CHEM035637)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:56:47 UTC
Update Date2016-11-09 01:21:21 UTC
Accession NumberCHEM035637
Identification
Common Name5-Methoxyindoleacetate
ClassSmall Molecule
DescriptionA member of the class of indole-3-acetic acids in which the hydrogen at position 5 of indole-3-acetic acid has been replaced by a methoxy group.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-(5-Methoxy-1H-indol-3-yl)ethanoic acidChEBI
2-(5-Methoxyindole-3-yl)acetic acidChEBI
5-Methoxyindol-3-ylacetic acidChEBI
5-Methoxyindoleacetic acidChEBI
2-(5-Methoxy-1H-indol-3-yl)ethanoateGenerator
2-(5-Methoxyindole-3-yl)acetateGenerator
5-Methoxyindol-3-ylacetateGenerator
5-Methoxyindole-3-acetateHMDB
5-Methoxyindole-3-acetic acidHMDB, MeSH
MethoxyindoleacetateHMDB
Methoxyindoleacetic acidHMDB
5-Methoxy-1H-indole-3-acetic acidHMDB
(5-Methoxy-1H-indol-3-yl)acetic acidHMDB
2-(5-Methoxy-1H-indol-3-yl)acetic acidHMDB
2-(5-Methoxy-3-indolyl)acetic acidHMDB
5-Methoxy-3-indoleacetic acidHMDB
5-Methoxy-3-indolylacetic acidHMDB
5-Methoxy-IAAHMDB
5-Methyloxyindole-3-acetic acidHMDB
5-MIAAHMDB
Chemical FormulaC11H11NO3
Average Molecular Mass205.210 g/mol
Monoisotopic Mass205.074 g/mol
CAS Registry Number3471-31-6
IUPAC Name2-(5-methoxy-1H-indol-3-yl)acetic acid
Traditional Name5-methoxyindole-3-acetic acid
SMILESCOC1=CC2=C(NC=C2CC(O)=O)C=C1
InChI IdentifierInChI=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 KeyCOCNDHOPIHDTHK-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolyl carboxylic acids and derivatives
Direct ParentIndole-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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.7 g/LALOGPS
logP1.76ALOGPS
logP1.55ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)4.3ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area62.32 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity54.92 m³·mol⁻¹ChemAxon
Polarizability20.73 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-1492000000-4bb4e49122eeca577f6fSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-1492000000-4bb4e49122eeca577f6fSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001i-0491000000-3833b4bbd544be9889d4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0bvl-1910000000-c1f37125fc3b608af61fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-5090000000-de75a303e99011a4be34Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0f6x-0950000000-b35cb5918f36be3e1ed9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udl-0900000000-4ecf8c9d3192ce786ee1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0900000000-8aed7fec3a54d7bd49ceSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udl-2900000000-d7b7a09d3453a1048a14Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-5900000000-de21476dd6d423ce7637Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0190000000-30a337d0188ca2b01e98Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0900000000-e29f13bccd0ff61f4d73Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0900000000-27318e117029d4756f51Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-02u1-0900000000-fc96484038377a19704eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-1900000000-b5ca37dc8dd19df79bcaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-7900000000-ceb8e6c122bb9a4d3fbbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-1910000000-8fd2478b70c897657b7fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-1900000000-7fd87377f29173005ec3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-9700000000-a4cf39ea98f467ad9511Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-9200000000-db11b5a046b68c168da7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-05n1-9100000000-0ff3c25c94ca7b6e75daSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-03di-0900000000-0c8ed04608a5330c9d3aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-014i-7900000000-95cba07fd384f9f59f79Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-1900000000-23403ec6bee04579f899Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0920000000-a3ced0adb5929f6c9416Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dr-0900000000-24447a7e06d2aa011318Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0hjj-1900000000-2026293826cbb03562deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0w29-0790000000-8c87e508e08c958691a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0w2i-0940000000-0373da6c43af5609fec7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052o-1900000000-44a6d63553f83a5e7004Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0004096
FooDB IDFDB023312
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID46224
BioCyc IDCPD-12020
METLIN ID7016
PDB IDMYI
Wikipedia LinkNot Available
Chemspider ID17924
ChEBI ID28281
PubChem Compound ID18986
Kegg Compound IDC05660
YMDB IDNot Available
ECMDB IDM2MDB005935
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11459072
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11701394
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=12106902
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=15950974
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=16141651
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=16318213
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=16512423
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=19185928
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=2423155
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=2446428
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=2476196
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=2481026
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=2580458
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=26960374
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=27723491
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=29160833
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=7537498
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=8946731
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=9345324
20. 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.
21. Higa S, Markey SP: Identification and quantification of 5-methoxyindole-3-acetic acid in human urine. Anal Biochem. 1985 Jan;144(1):86-93.
22. Meatherall R, Sharma P: Foxy, a designer tryptamine hallucinogen. J Anal Toxicol. 2003 Jul-Aug;27(5):313-7.
23. Sergeeva TI, Raushenbakh TI, Shevchenko MO, Rybal'chenko VG: [Excretion of 5-hydroxyindole-3-acetic and 5-methoxyindole-3-acetic acids in cancer patients]. Vopr Onkol. 1987;33(10):20-5.