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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-13 10:48:49 UTC
Update Date2020-02-26 21:24:58 UTC
HMDB IDHMDB0004096
Secondary Accession Numbers
  • HMDB04096
Metabolite Identification
Common Name5-Methoxyindoleacetate
Description5-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
Data?1582752298
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 Weight205.2099
Monoisotopic Molecular Weight205.073893223
IUPAC Name2-(5-methoxy-1H-indol-3-yl)acetic acid
Traditional Name5-methoxyindole-3-acetic acid
CAS Registry Number3471-31-6
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 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
Ontology
Disposition

Biological location

Source

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+MetCCS_train_pos144.00730932474
[M+H]+Not Available144.168http://allccs.zhulab.cn/database/detail?ID=AllCCS00000476
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+146.5331661259
DarkChem[M-H]-145.61831661259
DeepCCS[M+H]+145.26130932474
DeepCCS[M-H]-142.90330932474
DeepCCS[M-2H]-176.76730932474
DeepCCS[M+Na]+151.56230932474
AllCCS[M+H]+144.932859911
AllCCS[M+H-H2O]+140.732859911
AllCCS[M+NH4]+148.732859911
AllCCS[M+Na]+149.932859911
AllCCS[M-H]-145.932859911
AllCCS[M+Na-2H]-146.032859911
AllCCS[M+HCOO]-146.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-MethoxyindoleacetateCOC1=CC2=C(NC=C2CC(O)=O)C=C13585.1Standard polar33892256
5-MethoxyindoleacetateCOC1=CC2=C(NC=C2CC(O)=O)C=C12019.0Standard non polar33892256
5-MethoxyindoleacetateCOC1=CC2=C(NC=C2CC(O)=O)C=C12152.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-Methoxyindoleacetate,1TMS,isomer #1COC1=CC=C2[NH]C=C(CC(=O)O[Si](C)(C)C)C2=C12118.5Semi standard non polar33892256
5-Methoxyindoleacetate,1TMS,isomer #2COC1=CC=C2C(=C1)C(CC(=O)O)=CN2[Si](C)(C)C2227.9Semi standard non polar33892256
5-Methoxyindoleacetate,2TMS,isomer #1COC1=CC=C2C(=C1)C(CC(=O)O[Si](C)(C)C)=CN2[Si](C)(C)C2150.1Semi standard non polar33892256
5-Methoxyindoleacetate,2TMS,isomer #1COC1=CC=C2C(=C1)C(CC(=O)O[Si](C)(C)C)=CN2[Si](C)(C)C2155.3Standard non polar33892256
5-Methoxyindoleacetate,2TMS,isomer #1COC1=CC=C2C(=C1)C(CC(=O)O[Si](C)(C)C)=CN2[Si](C)(C)C2457.4Standard polar33892256
5-Methoxyindoleacetate,1TBDMS,isomer #1COC1=CC=C2[NH]C=C(CC(=O)O[Si](C)(C)C(C)(C)C)C2=C12394.2Semi standard non polar33892256
5-Methoxyindoleacetate,1TBDMS,isomer #2COC1=CC=C2C(=C1)C(CC(=O)O)=CN2[Si](C)(C)C(C)(C)C2453.3Semi standard non polar33892256
5-Methoxyindoleacetate,2TBDMS,isomer #1COC1=CC=C2C(=C1)C(CC(=O)O[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C2625.2Semi standard non polar33892256
5-Methoxyindoleacetate,2TBDMS,isomer #1COC1=CC=C2C(=C1)C(CC(=O)O[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C2585.0Standard non polar33892256
5-Methoxyindoleacetate,2TBDMS,isomer #1COC1=CC=C2C(=C1)C(CC(=O)O[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C2646.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 5-Methoxyindoleacetate GC-MS (2 TMS)splash10-001i-1492000000-4bb4e49122eeca577f6f2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5-Methoxyindoleacetate GC-MS (Non-derivatized)splash10-001i-1492000000-4bb4e49122eeca577f6f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5-Methoxyindoleacetate GC-EI-TOF (Non-derivatized)splash10-001i-0491000000-3833b4bbd544be9889d42017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methoxyindoleacetate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0bvl-1910000000-c1f37125fc3b608af61f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methoxyindoleacetate GC-MS (1 TMS) - 70eV, Positivesplash10-00di-5090000000-de75a303e99011a4be342017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methoxyindoleacetate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methoxyindoleacetate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methoxyindoleacetate LC-ESI-QQ , negative-QTOFsplash10-0f6x-0950000000-b35cb5918f36be3e1ed92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methoxyindoleacetate LC-ESI-QQ , negative-QTOFsplash10-0udl-0900000000-4ecf8c9d3192ce786ee12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methoxyindoleacetate LC-ESI-QQ , negative-QTOFsplash10-0udi-0900000000-8aed7fec3a54d7bd49ce2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methoxyindoleacetate LC-ESI-QQ , negative-QTOFsplash10-0udl-2900000000-d7b7a09d3453a1048a142017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methoxyindoleacetate LC-ESI-QQ , negative-QTOFsplash10-0006-5900000000-de21476dd6d423ce76372017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methoxyindoleacetate LC-ESI-QTOF , positive-QTOFsplash10-0a4i-0190000000-30a337d0188ca2b01e982017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methoxyindoleacetate LC-ESI-QTOF , positive-QTOFsplash10-03di-0900000000-e29f13bccd0ff61f4d732017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methoxyindoleacetate LC-ESI-QTOF , positive-QTOFsplash10-03di-0900000000-27318e117029d4756f512017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methoxyindoleacetate LC-ESI-QTOF , positive-QTOFsplash10-02u1-0900000000-fc96484038377a19704e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methoxyindoleacetate LC-ESI-QTOF , positive-QTOFsplash10-014i-1900000000-b5ca37dc8dd19df79bca2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methoxyindoleacetate LC-ESI-QTOF , positive-QTOFsplash10-014i-7900000000-ceb8e6c122bb9a4d3fbb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methoxyindoleacetate LC-ESI-QQ , positive-QTOFsplash10-0002-1910000000-8fd2478b70c897657b7f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methoxyindoleacetate LC-ESI-QQ , positive-QTOFsplash10-0002-1900000000-7fd87377f29173005ec32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methoxyindoleacetate LC-ESI-QQ , positive-QTOFsplash10-000i-9700000000-a4cf39ea98f467ad95112017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methoxyindoleacetate LC-ESI-QQ , positive-QTOFsplash10-000i-9200000000-db11b5a046b68c168da72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methoxyindoleacetate LC-ESI-QQ , positive-QTOFsplash10-05n1-9100000000-0ff3c25c94ca7b6e75da2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methoxyindoleacetate LC-ESI-IT , positive-QTOFsplash10-03di-0900000000-0c8ed04608a5330c9d3a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methoxyindoleacetate 60V, Positive-QTOFsplash10-014i-7900000000-95cba07fd384f9f59f792021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methoxyindoleacetate 40V, Positive-QTOFsplash10-014i-1900000000-23403ec6bee04579f8992021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methoxyindoleacetate 10V, Positive-QTOFsplash10-000i-0920000000-a3ced0adb5929f6c94162017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methoxyindoleacetate 20V, Positive-QTOFsplash10-03dr-0900000000-24447a7e06d2aa0113182017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methoxyindoleacetate 40V, Positive-QTOFsplash10-0hjj-1900000000-2026293826cbb03562de2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methoxyindoleacetate 10V, Negative-QTOFsplash10-0w29-0790000000-8c87e508e08c958691a72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methoxyindoleacetate 20V, Negative-QTOFsplash10-0w2i-0940000000-0373da6c43af5609fec72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methoxyindoleacetate 40V, Negative-QTOFsplash10-052o-1900000000-44a6d63553f83a5e70042017-09-01Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected and Quantified1.09 +/- 2.13 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothEnthesitis-related arthritis details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023312
KNApSAcK IDNot Available
Chemspider ID17924
KEGG Compound IDC05660
BioCyc IDCPD-12020
BiGG ID46224
Wikipedia LinkNot Available
METLIN ID7016
PubChem Compound18986
PDB IDMYI
ChEBI ID28281
Food Biomarker OntologyNot Available
VMH ID5MOXACT
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Higa S, Markey SP: Identification and quantification of 5-methoxyindole-3-acetic acid in human urine. Anal Biochem. 1985 Jan;144(1):86-93. [PubMed:2580458 ]
  2. Meatherall R, Sharma P: Foxy, a designer tryptamine hallucinogen. J Anal Toxicol. 2003 Jul-Aug;27(5):313-7. [PubMed:12908946 ]
  3. 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. [PubMed:2446428 ]

Enzymes

General function:
Involved in O-methyltransferase activity
Specific function:
Isoform 1 catalyzes the transfer of a methyl group onto N-acetylserotonin, producing melatonin (N-acetyl-5-methoxytryptamine). Isoform 2 and isoform 3 lack enzyme activity.
Gene Name:
ASMT
Uniprot ID:
P46597
Molecular weight:
41660.34
Reactions
S-Adenosylmethionine + 5-Hydroxyindoleacetic acid → S-Adenosylhomocysteine + 5-Methoxyindoleacetatedetails