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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2020-02-24 17:48:02 UTC
Update Date2022-03-07 03:18:20 UTC
HMDB IDHMDB0240640
Secondary Accession NumbersNone
Metabolite Identification
Common NameIndolepropionamide
DescriptionIndolepropionamide (IPAM) is a product of tryptophan metabolism formed by symbiotic bacteria in the gastrointestinal tract of mammals. In particular, IPAM is an amide derivatization product of indole-3-propionic acid (IPA). IPAM reduces reactive oxygen species by inhibiting oxidative phosphorylation in complex I of the electron transport chain and acts as a stabilizer of energy metabolism, thereby reducing reactive oxygen species (ROS) production. In contrast to indole-3-propionic acid which bears a polar carboxyl group that is ionized at physiological pH carrying a negative charge, IPAM is non-polar and has sufficient lipophilicity to penetrate through biological membranes. In contrast to melatonin, IPAM is a "reversed amide" lacking the methoxy group as an aromatic substituent. In contrast to IPAM, melatonin is quickly metabolized in the liver by hydroxylation and excreted as the glucuronide or sulfate conjugate of 6-hydroxymelatonin (a pro-oxidant metabolite). IPAM, however, has a long half-life and no pro-oxidant activity (PMID: 20421998 ).
Structure
Data?1582566488
Synonyms
ValueSource
3-(1H-indol-3-yl)PropanamideHMDB
3-(3-Indolyl)propanamideHMDB
3-indol-3-YlpropionamideHMDB
3-IndolepropanamideHMDB
IPAMHMDB
Indole-3-propionamideHMDB
IndolepropionamideHMDB
Chemical FormulaC11H12N2O
Average Molecular Weight188.23
Monoisotopic Molecular Weight188.094963014
IUPAC Name3-(1H-indol-3-yl)propanamide
Traditional Name3-(1H-indol-3-yl)propanamide
CAS Registry Number5814-93-7
SMILES
NC(=O)CCC1=CNC2=C1C=CC=C2
InChI Identifier
InChI=1S/C11H12N2O/c12-11(14)6-5-8-7-13-10-4-2-1-3-9(8)10/h1-4,7,13H,5-6H2,(H2,12,14)
InChI KeyOTVHXWFANORBAK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tryptamines and derivatives. Tryptamines and derivatives are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassTryptamines and derivatives
Direct ParentTryptamines and derivatives
Alternative Parents
Substituents
  • Triptan
  • 3-alkylindole
  • Indole
  • Fatty amide
  • Substituted pyrrole
  • Benzenoid
  • Fatty acyl
  • Pyrrole
  • Heteroaromatic compound
  • Carboxamide group
  • Primary carboxylic acid amide
  • Carboxylic acid derivative
  • Azacycle
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
DispositionNot Available
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
logP1.51ALOGPS
logP1.35ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)16.06ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.88 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity54.88 m³·mol⁻¹ChemAxon
Polarizability20.36 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
DeepCCS[M+H]+139.00530932474
DeepCCS[M-H]-136.24130932474
DeepCCS[M-2H]-172.61830932474
DeepCCS[M+Na]+148.15630932474
AllCCS[M+H]+141.932859911
AllCCS[M+H-H2O]+137.632859911
AllCCS[M+NH4]+145.832859911
AllCCS[M+Na]+147.032859911
AllCCS[M-H]-143.932859911
AllCCS[M+Na-2H]-144.232859911
AllCCS[M+HCOO]-144.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IndolepropionamideNC(=O)CCC1=CNC2=C1C=CC=C23389.0Standard polar33892256
IndolepropionamideNC(=O)CCC1=CNC2=C1C=CC=C22107.9Standard non polar33892256
IndolepropionamideNC(=O)CCC1=CNC2=C1C=CC=C22203.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Indolepropionamide,1TMS,isomer #1C[Si](C)(C)NC(=O)CCC1=C[NH]C2=CC=CC=C122144.9Semi standard non polar33892256
Indolepropionamide,1TMS,isomer #1C[Si](C)(C)NC(=O)CCC1=C[NH]C2=CC=CC=C122081.1Standard non polar33892256
Indolepropionamide,1TMS,isomer #1C[Si](C)(C)NC(=O)CCC1=C[NH]C2=CC=CC=C122697.4Standard polar33892256
Indolepropionamide,1TMS,isomer #2C[Si](C)(C)N1C=C(CCC(N)=O)C2=CC=CC=C212134.2Semi standard non polar33892256
Indolepropionamide,1TMS,isomer #2C[Si](C)(C)N1C=C(CCC(N)=O)C2=CC=CC=C212034.3Standard non polar33892256
Indolepropionamide,1TMS,isomer #2C[Si](C)(C)N1C=C(CCC(N)=O)C2=CC=CC=C212921.8Standard polar33892256
Indolepropionamide,2TMS,isomer #1C[Si](C)(C)N(C(=O)CCC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C2272.3Semi standard non polar33892256
Indolepropionamide,2TMS,isomer #1C[Si](C)(C)N(C(=O)CCC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C2243.8Standard non polar33892256
Indolepropionamide,2TMS,isomer #1C[Si](C)(C)N(C(=O)CCC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C2561.0Standard polar33892256
Indolepropionamide,2TMS,isomer #2C[Si](C)(C)NC(=O)CCC1=CN([Si](C)(C)C)C2=CC=CC=C122167.1Semi standard non polar33892256
Indolepropionamide,2TMS,isomer #2C[Si](C)(C)NC(=O)CCC1=CN([Si](C)(C)C)C2=CC=CC=C122156.4Standard non polar33892256
Indolepropionamide,2TMS,isomer #2C[Si](C)(C)NC(=O)CCC1=CN([Si](C)(C)C)C2=CC=CC=C122433.1Standard polar33892256
Indolepropionamide,3TMS,isomer #1C[Si](C)(C)N(C(=O)CCC1=CN([Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C2313.1Semi standard non polar33892256
Indolepropionamide,3TMS,isomer #1C[Si](C)(C)N(C(=O)CCC1=CN([Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C2281.7Standard non polar33892256
Indolepropionamide,3TMS,isomer #1C[Si](C)(C)N(C(=O)CCC1=CN([Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C2360.7Standard polar33892256
Indolepropionamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)CCC1=C[NH]C2=CC=CC=C122376.0Semi standard non polar33892256
Indolepropionamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)CCC1=C[NH]C2=CC=CC=C122290.0Standard non polar33892256
Indolepropionamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)CCC1=C[NH]C2=CC=CC=C122763.2Standard polar33892256
Indolepropionamide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=C(CCC(N)=O)C2=CC=CC=C212386.4Semi standard non polar33892256
Indolepropionamide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=C(CCC(N)=O)C2=CC=CC=C212240.2Standard non polar33892256
Indolepropionamide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=C(CCC(N)=O)C2=CC=CC=C212982.3Standard polar33892256
Indolepropionamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)CCC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C(C)(C)C2726.1Semi standard non polar33892256
Indolepropionamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)CCC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C(C)(C)C2684.5Standard non polar33892256
Indolepropionamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)CCC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C(C)(C)C2666.0Standard polar33892256
Indolepropionamide,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(=O)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122620.2Semi standard non polar33892256
Indolepropionamide,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(=O)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122578.5Standard non polar33892256
Indolepropionamide,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(=O)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122618.5Standard polar33892256
Indolepropionamide,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C2920.6Semi standard non polar33892256
Indolepropionamide,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C2900.5Standard non polar33892256
Indolepropionamide,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C2636.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Indolepropionamide 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 - Indolepropionamide 10V, Positive-QTOFsplash10-001i-0900000000-a6c6cf65771bf60da87b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indolepropionamide 20V, Positive-QTOFsplash10-001i-0900000000-1dd20caaf8946c0cc1672021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indolepropionamide 40V, Positive-QTOFsplash10-0fvl-5900000000-bf2e9bb93f2843450f572021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indolepropionamide 10V, Negative-QTOFsplash10-000l-0900000000-f369bd1b50d501c475c52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indolepropionamide 20V, Negative-QTOFsplash10-066r-7900000000-875077392f8aefecbafa2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indolepropionamide 40V, Negative-QTOFsplash10-014i-0900000000-c776cb5758d92e719aa12021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDNot Available
KNApSAcK IDNot Available
Chemspider ID312353
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIndolepropionamide
METLIN IDNot Available
PubChem Compound351791
PDB IDNot Available
ChEBI IDNot Available
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. Poeggeler B, Sambamurti K, Siedlak SL, Perry G, Smith MA, Pappolla MA: A novel endogenous indole protects rodent mitochondria and extends rotifer lifespan. PLoS One. 2010 Apr 21;5(4):e10206. doi: 10.1371/journal.pone.0010206. [PubMed:20421998 ]