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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:41:27 UTC
Update Date2023-02-21 17:19:57 UTC
HMDB IDHMDB0031173
Secondary Accession Numbers
  • HMDB31173
Metabolite Identification
Common Name6-Hydroxy-1H-indole-3-acetamide
Description6-Hydroxy-1H-indole-3-acetamide, also known as 6-hi-3a, belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group. Based on a literature review very few articles have been published on 6-Hydroxy-1H-indole-3-acetamide.
Structure
Data?1676999997
Synonyms
ValueSource
6-HI-3aHMDB
2-(6-Hydroxy-1H-indol-3-yl)ethanimidateHMDB
6-Hydroxy-1H-indole-3-acetamideMeSH
Chemical FormulaC10H10N2O2
Average Molecular Weight190.1986
Monoisotopic Molecular Weight190.074227574
IUPAC Name2-(6-hydroxy-1H-indol-3-yl)acetamide
Traditional Name2-(6-hydroxy-1H-indol-3-yl)acetamide
CAS Registry Number192184-73-9
SMILES
NC(=O)CC1=CNC2=C1C=CC(O)=C2
InChI Identifier
InChI=1S/C10H10N2O2/c11-10(14)3-6-5-12-9-4-7(13)1-2-8(6)9/h1-2,4-5,12-13H,3H2,(H2,11,14)
InChI KeyPGXXGODNTPWQHZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassHydroxyindoles
Direct ParentHydroxyindoles
Alternative Parents
Substituents
  • 3-alkylindole
  • Hydroxyindole
  • Indole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Substituted pyrrole
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Primary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.89 g/LALOGPS
logP0.49ALOGPS
logP0.6ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)9.52ChemAxon
pKa (Strongest Basic)-2.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area79.11 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity52.26 m³·mol⁻¹ChemAxon
Polarizability19.23 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]+144.10231661259
DarkChem[M-H]-141.04631661259
DeepCCS[M+H]+140.91430932474
DeepCCS[M-H]-138.10130932474
DeepCCS[M-2H]-174.31230932474
DeepCCS[M+Na]+149.85130932474
AllCCS[M+H]+141.632859911
AllCCS[M+H-H2O]+137.332859911
AllCCS[M+NH4]+145.532859911
AllCCS[M+Na]+146.732859911
AllCCS[M-H]-141.932859911
AllCCS[M+Na-2H]-142.132859911
AllCCS[M+HCOO]-142.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
6-Hydroxy-1H-indole-3-acetamideNC(=O)CC1=CNC2=C1C=CC(O)=C23710.3Standard polar33892256
6-Hydroxy-1H-indole-3-acetamideNC(=O)CC1=CNC2=C1C=CC(O)=C22252.2Standard non polar33892256
6-Hydroxy-1H-indole-3-acetamideNC(=O)CC1=CNC2=C1C=CC(O)=C22413.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
6-Hydroxy-1H-indole-3-acetamide,1TMS,isomer #1C[Si](C)(C)OC1=CC=C2C(CC(N)=O)=C[NH]C2=C12345.8Semi standard non polar33892256
6-Hydroxy-1H-indole-3-acetamide,1TMS,isomer #2C[Si](C)(C)NC(=O)CC1=C[NH]C2=CC(O)=CC=C122338.8Semi standard non polar33892256
6-Hydroxy-1H-indole-3-acetamide,1TMS,isomer #3C[Si](C)(C)N1C=C(CC(N)=O)C2=CC=C(O)C=C212334.3Semi standard non polar33892256
6-Hydroxy-1H-indole-3-acetamide,2TMS,isomer #1C[Si](C)(C)NC(=O)CC1=C[NH]C2=CC(O[Si](C)(C)C)=CC=C122356.3Semi standard non polar33892256
6-Hydroxy-1H-indole-3-acetamide,2TMS,isomer #1C[Si](C)(C)NC(=O)CC1=C[NH]C2=CC(O[Si](C)(C)C)=CC=C122324.8Standard non polar33892256
6-Hydroxy-1H-indole-3-acetamide,2TMS,isomer #2C[Si](C)(C)OC1=CC=C2C(CC(N)=O)=CN([Si](C)(C)C)C2=C12355.1Semi standard non polar33892256
6-Hydroxy-1H-indole-3-acetamide,2TMS,isomer #2C[Si](C)(C)OC1=CC=C2C(CC(N)=O)=CN([Si](C)(C)C)C2=C12218.0Standard non polar33892256
6-Hydroxy-1H-indole-3-acetamide,2TMS,isomer #3C[Si](C)(C)N(C(=O)CC1=C[NH]C2=CC(O)=CC=C12)[Si](C)(C)C2438.3Semi standard non polar33892256
6-Hydroxy-1H-indole-3-acetamide,2TMS,isomer #3C[Si](C)(C)N(C(=O)CC1=C[NH]C2=CC(O)=CC=C12)[Si](C)(C)C2425.8Standard non polar33892256
6-Hydroxy-1H-indole-3-acetamide,2TMS,isomer #4C[Si](C)(C)NC(=O)CC1=CN([Si](C)(C)C)C2=CC(O)=CC=C122341.7Semi standard non polar33892256
6-Hydroxy-1H-indole-3-acetamide,2TMS,isomer #4C[Si](C)(C)NC(=O)CC1=CN([Si](C)(C)C)C2=CC(O)=CC=C122412.9Standard non polar33892256
6-Hydroxy-1H-indole-3-acetamide,3TMS,isomer #1C[Si](C)(C)OC1=CC=C2C(CC(=O)N([Si](C)(C)C)[Si](C)(C)C)=C[NH]C2=C12393.7Semi standard non polar33892256
6-Hydroxy-1H-indole-3-acetamide,3TMS,isomer #1C[Si](C)(C)OC1=CC=C2C(CC(=O)N([Si](C)(C)C)[Si](C)(C)C)=C[NH]C2=C12436.5Standard non polar33892256
6-Hydroxy-1H-indole-3-acetamide,3TMS,isomer #2C[Si](C)(C)NC(=O)CC1=CN([Si](C)(C)C)C2=CC(O[Si](C)(C)C)=CC=C122372.1Semi standard non polar33892256
6-Hydroxy-1H-indole-3-acetamide,3TMS,isomer #2C[Si](C)(C)NC(=O)CC1=CN([Si](C)(C)C)C2=CC(O[Si](C)(C)C)=CC=C122329.2Standard non polar33892256
6-Hydroxy-1H-indole-3-acetamide,3TMS,isomer #3C[Si](C)(C)N(C(=O)CC1=CN([Si](C)(C)C)C2=CC(O)=CC=C12)[Si](C)(C)C2426.7Semi standard non polar33892256
6-Hydroxy-1H-indole-3-acetamide,3TMS,isomer #3C[Si](C)(C)N(C(=O)CC1=CN([Si](C)(C)C)C2=CC(O)=CC=C12)[Si](C)(C)C2503.4Standard non polar33892256
6-Hydroxy-1H-indole-3-acetamide,4TMS,isomer #1C[Si](C)(C)OC1=CC=C2C(CC(=O)N([Si](C)(C)C)[Si](C)(C)C)=CN([Si](C)(C)C)C2=C12466.2Semi standard non polar33892256
6-Hydroxy-1H-indole-3-acetamide,4TMS,isomer #1C[Si](C)(C)OC1=CC=C2C(CC(=O)N([Si](C)(C)C)[Si](C)(C)C)=CN([Si](C)(C)C)C2=C12450.0Standard non polar33892256
6-Hydroxy-1H-indole-3-acetamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C(CC(N)=O)=C[NH]C2=C12604.7Semi standard non polar33892256
6-Hydroxy-1H-indole-3-acetamide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(=O)CC1=C[NH]C2=CC(O)=CC=C122596.9Semi standard non polar33892256
6-Hydroxy-1H-indole-3-acetamide,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C=C(CC(N)=O)C2=CC=C(O)C=C212574.1Semi standard non polar33892256
6-Hydroxy-1H-indole-3-acetamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)CC1=C[NH]C2=CC(O[Si](C)(C)C(C)(C)C)=CC=C122826.5Semi standard non polar33892256
6-Hydroxy-1H-indole-3-acetamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)CC1=C[NH]C2=CC(O[Si](C)(C)C(C)(C)C)=CC=C122748.5Standard non polar33892256
6-Hydroxy-1H-indole-3-acetamide,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C2C(CC(N)=O)=CN([Si](C)(C)C(C)(C)C)C2=C12858.8Semi standard non polar33892256
6-Hydroxy-1H-indole-3-acetamide,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C2C(CC(N)=O)=CN([Si](C)(C)C(C)(C)C)C2=C12642.2Standard non polar33892256
6-Hydroxy-1H-indole-3-acetamide,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(C(=O)CC1=C[NH]C2=CC(O)=CC=C12)[Si](C)(C)C(C)(C)C2860.5Semi standard non polar33892256
6-Hydroxy-1H-indole-3-acetamide,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(C(=O)CC1=C[NH]C2=CC(O)=CC=C12)[Si](C)(C)C(C)(C)C2868.1Standard non polar33892256
6-Hydroxy-1H-indole-3-acetamide,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC(O)=CC=C122819.7Semi standard non polar33892256
6-Hydroxy-1H-indole-3-acetamide,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC(O)=CC=C122806.4Standard non polar33892256
6-Hydroxy-1H-indole-3-acetamide,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C(CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C[NH]C2=C13099.9Semi standard non polar33892256
6-Hydroxy-1H-indole-3-acetamide,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C(CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C[NH]C2=C13066.6Standard non polar33892256
6-Hydroxy-1H-indole-3-acetamide,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC(O[Si](C)(C)C(C)(C)C)=CC=C123026.8Semi standard non polar33892256
6-Hydroxy-1H-indole-3-acetamide,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC(O[Si](C)(C)C(C)(C)C)=CC=C122940.0Standard non polar33892256
6-Hydroxy-1H-indole-3-acetamide,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(C(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC(O)=CC=C12)[Si](C)(C)C(C)(C)C3063.4Semi standard non polar33892256
6-Hydroxy-1H-indole-3-acetamide,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(C(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC(O)=CC=C12)[Si](C)(C)C(C)(C)C3104.1Standard non polar33892256
6-Hydroxy-1H-indole-3-acetamide,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C(CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CN([Si](C)(C)C(C)(C)C)C2=C13276.7Semi standard non polar33892256
6-Hydroxy-1H-indole-3-acetamide,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C(CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CN([Si](C)(C)C(C)(C)C)C2=C13219.2Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 6-Hydroxy-1H-indole-3-acetamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-1900000000-1653c95429913a8c4d5b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Hydroxy-1H-indole-3-acetamide GC-MS (1 TMS) - 70eV, Positivesplash10-00dm-8790000000-45b6ea18c84febb5f83e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Hydroxy-1H-indole-3-acetamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Hydroxy-1H-indole-3-acetamide 10V, Positive-QTOFsplash10-006x-0900000000-de14fc15a207756b4c2b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Hydroxy-1H-indole-3-acetamide 20V, Positive-QTOFsplash10-00dj-0900000000-75797c57d7ade8d643642016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Hydroxy-1H-indole-3-acetamide 40V, Positive-QTOFsplash10-000t-0900000000-ccda37806e581232eedb2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Hydroxy-1H-indole-3-acetamide 10V, Negative-QTOFsplash10-000i-0900000000-c0e17c19b05a4ff287a82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Hydroxy-1H-indole-3-acetamide 20V, Negative-QTOFsplash10-000j-2900000000-4eb14c6cc7733af68da52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Hydroxy-1H-indole-3-acetamide 40V, Negative-QTOFsplash10-0006-9200000000-bf56b91112ab3598410e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Hydroxy-1H-indole-3-acetamide 10V, Positive-QTOFsplash10-00dm-0900000000-57e604b71d1060e1b6bf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Hydroxy-1H-indole-3-acetamide 20V, Positive-QTOFsplash10-006t-0900000000-b874f2038a5eba77f5052021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Hydroxy-1H-indole-3-acetamide 40V, Positive-QTOFsplash10-0gba-1900000000-1c4acaaeb74d9663a92b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Hydroxy-1H-indole-3-acetamide 10V, Negative-QTOFsplash10-007a-0900000000-8d613d72e9ef06b7000a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Hydroxy-1H-indole-3-acetamide 20V, Negative-QTOFsplash10-006x-3900000000-f6b3b86efb20aab077c52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Hydroxy-1H-indole-3-acetamide 40V, Negative-QTOFsplash10-0006-9000000000-8ed5d346035c3042d26f2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003190
KNApSAcK IDNot Available
Chemspider ID252618
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound286538
PDB IDNot Available
ChEBI ID563250
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.. .