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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:32:20 UTC
Update Date2021-10-13 06:02:46 UTC
HMDB IDHMDB0029739
Secondary Accession Numbers
  • HMDB29739
Metabolite Identification
Common NameIndole-3-acetamide
DescriptionIndole-3-acetamide, also known as 2-(3-indolyl)acetamide or IAM, belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. Indole-3-acetamide has been detected, but not quantified, in several different foods, such as Alaska wild rhubarbs, lingonberries, butternut squash, pineapples, and agaves. Indole-3-acetamide is also found in the common pea and has been isolated from the etiolated seedlings of the black gram (Phaseolus mungo).
Structure
Data?1586973577
Synonyms
ValueSource
1H-Indole-3-acetamideChEBI
3-IndoleacetamideChEBI
IndoleacetamideChEBI
Auxin amideMeSH
(indol-3-yl)AcetamideHMDB
1-Indole-3-acetamideHMDB
2-(1H-Indol-3-yl)acetamideHMDB
2-(3-Indolyl)acetamideHMDB
3-IndolylacetamideHMDB
IAMHMDB
Indole-3-acetamideHMDB, KEGG
Indole-3-acetamide (6ci,8ci)HMDB
Indole-3-acetamide (8ci)HMDB
TSCHMDB
TSRHMDB
Chemical FormulaC10H10N2O
Average Molecular Weight174.1992
Monoisotopic Molecular Weight174.079312952
IUPAC Name2-(1H-indol-3-yl)acetamide
Traditional Nameindole-3-acetamide
CAS Registry Number879-37-8
SMILES
NC(=O)CC1=CNC2=C1C=CC=C2
InChI Identifier
InChI=1S/C10H10N2O/c11-10(13)5-7-6-12-9-4-2-1-3-8(7)9/h1-4,6,12H,5H2,(H2,11,13)
InChI KeyZOAMBXDOGPRZLP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct Parent3-alkylindoles
Alternative Parents
Substituents
  • 3-alkylindole
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Carboximidic acid derivative
  • Carboximidic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point150 - 151 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility13440 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available136.0http://allccs.zhulab.cn/database/detail?ID=AllCCS00002125
[M+H]+Not Available137.4http://allccs.zhulab.cn/database/detail?ID=AllCCS00002125
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.25 g/LALOGPS
logP10(1.17) g/LALOGPS
logP10(0.9) g/LChemAxon
logS10(-2) g/LALOGPS
pKa (Strongest Acidic)15.94ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.88 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity50.27 m³·mol⁻¹ChemAxon
Polarizability18.23 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]+138.55831661259
DarkChem[M-H]-136.08231661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Indole-3-acetamideNC(=O)CC1=CNC2=C1C=CC=C23254.5Standard polar33892256
Indole-3-acetamideNC(=O)CC1=CNC2=C1C=CC=C22059.5Standard non polar33892256
Indole-3-acetamideNC(=O)CC1=CNC2=C1C=CC=C22098.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Indole-3-acetamide,1TMS,isomer #1C[Si](C)(C)NC(=O)CC1=C[NH]C2=CC=CC=C122041.3Semi standard non polar33892256
Indole-3-acetamide,1TMS,isomer #1C[Si](C)(C)NC(=O)CC1=C[NH]C2=CC=CC=C121983.4Standard non polar33892256
Indole-3-acetamide,1TMS,isomer #2C[Si](C)(C)N1C=C(CC(N)=O)C2=CC=CC=C212083.3Semi standard non polar33892256
Indole-3-acetamide,1TMS,isomer #2C[Si](C)(C)N1C=C(CC(N)=O)C2=CC=CC=C211940.7Standard non polar33892256
Indole-3-acetamide,2TMS,isomer #1C[Si](C)(C)N(C(=O)CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C2165.8Semi standard non polar33892256
Indole-3-acetamide,2TMS,isomer #1C[Si](C)(C)N(C(=O)CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C2147.7Standard non polar33892256
Indole-3-acetamide,2TMS,isomer #2C[Si](C)(C)NC(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C122077.8Semi standard non polar33892256
Indole-3-acetamide,2TMS,isomer #2C[Si](C)(C)NC(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C122075.3Standard non polar33892256
Indole-3-acetamide,3TMS,isomer #1C[Si](C)(C)N(C(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C2204.7Semi standard non polar33892256
Indole-3-acetamide,3TMS,isomer #1C[Si](C)(C)N(C(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C2202.4Standard non polar33892256
Indole-3-acetamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)CC1=C[NH]C2=CC=CC=C122281.3Semi standard non polar33892256
Indole-3-acetamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)CC1=C[NH]C2=CC=CC=C122168.9Standard non polar33892256
Indole-3-acetamide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=C(CC(N)=O)C2=CC=CC=C212324.7Semi standard non polar33892256
Indole-3-acetamide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=C(CC(N)=O)C2=CC=CC=C212134.2Standard non polar33892256
Indole-3-acetamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C(C)(C)C2615.7Semi standard non polar33892256
Indole-3-acetamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C(C)(C)C2577.3Standard non polar33892256
Indole-3-acetamide,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122510.1Semi standard non polar33892256
Indole-3-acetamide,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122490.5Standard non polar33892256
Indole-3-acetamide,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C2793.6Semi standard non polar33892256
Indole-3-acetamide,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C2821.6Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Indole-3-acetamide GC-MS (3 TMS)splash10-000i-1940000000-2e0b818a401b68b37cb02014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indole-3-acetamide GC-MS (2 TMS)splash10-0udi-1690000000-bd0b44e69af5595426d52014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indole-3-acetamide GC-MS (Non-derivatized)splash10-000i-1940000000-2e0b818a401b68b37cb02017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indole-3-acetamide GC-MS (Non-derivatized)splash10-0udi-1690000000-bd0b44e69af5595426d52017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indole-3-acetamide GC-EI-TOF (Non-derivatized)splash10-0udi-0690000000-7d97254bac7f634f8ef62017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indole-3-acetamide GC-EI-TOF (Non-derivatized)splash10-0006-0790000000-3baf5bdb295590ef5e302017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indole-3-acetamide GC-EI-TOF (Non-derivatized)splash10-014i-0490000000-68d3c7497fdc144df3ff2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indole-3-acetamide GC-EI-TOF (Non-derivatized)splash10-014i-0962600000-44dab9af3d483d3248602017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Indole-3-acetamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-1900000000-bee6d4f863595e61f64c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Indole-3-acetamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-001i-4900000000-6404e04bc67c64bf01fe2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-acetamide LC-ESI-QQ , negative-QTOFsplash10-00di-0900000000-8e500497980b176c3b932017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-acetamide LC-ESI-QQ , negative-QTOFsplash10-0089-0900000000-7ed0e1427315880135e92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-acetamide LC-ESI-QQ , negative-QTOFsplash10-001i-0900000000-fc7d0772d90e4729aef22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-acetamide LC-ESI-QQ , negative-QTOFsplash10-0059-3900000000-f1a9ae54e7b833bbf7262017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-acetamide LC-ESI-QQ , negative-QTOFsplash10-0006-9500000000-1c040087111497793e632017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-acetamide , negative-QTOFsplash10-00e9-0900000000-9f05f0a7e9fe3835ecf32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-acetamide , positive-QTOFsplash10-001i-0900000000-67ccc2768cce859f24992017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-acetamide 35V, Negative-QTOFsplash10-00e9-0900000000-40c799aeb47a282dda9e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-acetamide 10V, Negative-QTOFsplash10-00di-0900000000-94ea4a1c3d4e34debac92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-acetamide 20V, Positive-QTOFsplash10-001i-0900000000-c5a3e3d2da08ed3d6ab92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-acetamide 10V, Positive-QTOFsplash10-001i-0900000000-269e12170dc5be0e70732021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-acetamide 35V, Negative-QTOFsplash10-001i-0900000000-c1b8fc03b1893c6c77322021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-acetamide 40V, Positive-QTOFsplash10-0fc0-4900000000-8071bee81ef6d0157bee2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-acetamide 35V, Positive-QTOFsplash10-001i-0900000000-0f6021a437dc4ae1d5892021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-acetamide 35V, Positive-QTOFsplash10-001i-0900000000-2781bfef6ced20d656662021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-acetamide 35V, Positive-QTOFsplash10-001i-0900000000-5de87672862d9a87ffad2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-acetamide 40V, Negative-QTOFsplash10-0006-9000000000-a7211114eee7d20849642021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-acetamide 20V, Negative-QTOFsplash10-001i-1900000000-3de8c91d628d34d622902021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-acetamide 10V, Positive-QTOFsplash10-0a6r-0900000000-1f155ed0ed5f83f867252015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-acetamide 20V, Positive-QTOFsplash10-0a59-0900000000-07eabe3745639209f1332015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-acetamide 40V, Positive-QTOFsplash10-001i-1900000000-b726329bdc2f6e86c3312015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-acetamide 10V, Negative-QTOFsplash10-00di-0900000000-a3d953ff50b9cf8574732015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-acetamide 20V, Negative-QTOFsplash10-00ec-2900000000-945fb87e55e153b511602015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-acetamide 40V, Negative-QTOFsplash10-0006-9300000000-8838f76ce5faa9a043372015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-acetamide 10V, Negative-QTOFsplash10-00di-2900000000-10871b30e21061e9ad032021-09-21Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB08652
Phenol Explorer Compound IDNot Available
FooDB IDFDB000937
KNApSAcK IDC00000108
Chemspider ID386
KEGG Compound IDC02693
BioCyc IDCPD-237
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound397
PDB IDTSR
ChEBI ID16031
Food Biomarker OntologyNot Available
VMH IDIND3ACAM
MarkerDB IDNot Available
Good Scents IDrw1251491
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .