Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:18:28 UTC
Update Date2022-03-07 02:56:00 UTC
HMDB IDHMDB0038961
Secondary Accession Numbers
  • HMDB38961
Metabolite Identification
Common NameN-[2-(1H-Indol-3-yl)ethyl]docosanamide
DescriptionN-[2-(1H-Indol-3-yl)ethyl]docosanamide 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. N-[2-(1H-Indol-3-yl)ethyl]docosanamide has been detected, but not quantified in, several different foods, such as alcoholic beverages, cocoa and cocoa products, cocoa beans (Theobroma cacao), fats and oils, and fruits. This could make N-[2-(1H-indol-3-yl)ethyl]docosanamide a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on N-[2-(1H-Indol-3-yl)ethyl]docosanamide.
Structure
Data?1563863288
Synonyms
ValueSource
N-BehenoyltryptamineChEMBL, HMDB
3-[2-(Docosanoylaminoethyl)]indoleHMDB
Behenic acid tryptamideHMDB
NB-BehenoyltryptamineHMDB
NB-DocosanoyltryptamineHMDB
N-[2-(1H-indol-3-yl)Ethyl]docosanimidateGenerator
Chemical FormulaC32H54N2O
Average Molecular Weight482.784
Monoisotopic Molecular Weight482.42361436
IUPAC NameN-[2-(1H-indol-3-yl)ethyl]docosanamide
Traditional NameN-[2-(1H-indol-3-yl)ethyl]docosanamide
CAS Registry Number7367-79-5
SMILES
CCCCCCCCCCCCCCCCCCCCCC(=O)NCCC1=CNC2=C1C=CC=C2
InChI Identifier
InChI=1S/C32H54N2O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-25-32(35)33-27-26-29-28-34-31-24-22-21-23-30(29)31/h21-24,28,34H,2-20,25-27H2,1H3,(H,33,35)
InChI KeyHAWFHRQOMIMGFR-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
  • Fatty amide
  • N-acyl-amine
  • Substituted pyrrole
  • Benzenoid
  • Fatty acyl
  • Pyrrole
  • Heteroaromatic compound
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Azacycle
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point121 - 123 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.4e-05 g/LALOGPS
logP9.3ALOGPS
logP10.45ChemAxon
logS-7.6ALOGPS
pKa (Strongest Acidic)15.9ChemAxon
pKa (Strongest Basic)-0.25ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area44.89 ŲChemAxon
Rotatable Bond Count23ChemAxon
Refractivity151.86 m³·mol⁻¹ChemAxon
Polarizability65 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+224.87131661259
DarkChem[M-H]-222.82331661259
DeepCCS[M+H]+227.13130932474
DeepCCS[M-H]-223.5430932474
DeepCCS[M-2H]-259.65630932474
DeepCCS[M+Na]+235.94630932474
AllCCS[M+H]+233.432859911
AllCCS[M+H-H2O]+231.932859911
AllCCS[M+NH4]+234.732859911
AllCCS[M+Na]+235.132859911
AllCCS[M-H]-220.232859911
AllCCS[M+Na-2H]-224.132859911
AllCCS[M+HCOO]-228.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-[2-(1H-Indol-3-yl)ethyl]docosanamideCCCCCCCCCCCCCCCCCCCCCC(=O)NCCC1=CNC2=C1C=CC=C24590.0Standard polar33892256
N-[2-(1H-Indol-3-yl)ethyl]docosanamideCCCCCCCCCCCCCCCCCCCCCC(=O)NCCC1=CNC2=C1C=CC=C23924.9Standard non polar33892256
N-[2-(1H-Indol-3-yl)ethyl]docosanamideCCCCCCCCCCCCCCCCCCCCCC(=O)NCCC1=CNC2=C1C=CC=C24361.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-[2-(1H-Indol-3-yl)ethyl]docosanamide,1TMS,isomer #1CCCCCCCCCCCCCCCCCCCCCC(=O)N(CCC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C4129.3Semi standard non polar33892256
N-[2-(1H-Indol-3-yl)ethyl]docosanamide,1TMS,isomer #1CCCCCCCCCCCCCCCCCCCCCC(=O)N(CCC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C4015.3Standard non polar33892256
N-[2-(1H-Indol-3-yl)ethyl]docosanamide,1TMS,isomer #2CCCCCCCCCCCCCCCCCCCCCC(=O)NCCC1=CN([Si](C)(C)C)C2=CC=CC=C124184.1Semi standard non polar33892256
N-[2-(1H-Indol-3-yl)ethyl]docosanamide,1TMS,isomer #2CCCCCCCCCCCCCCCCCCCCCC(=O)NCCC1=CN([Si](C)(C)C)C2=CC=CC=C123885.6Standard non polar33892256
N-[2-(1H-Indol-3-yl)ethyl]docosanamide,2TMS,isomer #1CCCCCCCCCCCCCCCCCCCCCC(=O)N(CCC1=CN([Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C4164.0Semi standard non polar33892256
N-[2-(1H-Indol-3-yl)ethyl]docosanamide,2TMS,isomer #1CCCCCCCCCCCCCCCCCCCCCC(=O)N(CCC1=CN([Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C3968.9Standard non polar33892256
N-[2-(1H-Indol-3-yl)ethyl]docosanamide,1TBDMS,isomer #1CCCCCCCCCCCCCCCCCCCCCC(=O)N(CCC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C(C)(C)C4364.9Semi standard non polar33892256
N-[2-(1H-Indol-3-yl)ethyl]docosanamide,1TBDMS,isomer #1CCCCCCCCCCCCCCCCCCCCCC(=O)N(CCC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C(C)(C)C4205.0Standard non polar33892256
N-[2-(1H-Indol-3-yl)ethyl]docosanamide,1TBDMS,isomer #2CCCCCCCCCCCCCCCCCCCCCC(=O)NCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C124388.5Semi standard non polar33892256
N-[2-(1H-Indol-3-yl)ethyl]docosanamide,1TBDMS,isomer #2CCCCCCCCCCCCCCCCCCCCCC(=O)NCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C124057.8Standard non polar33892256
N-[2-(1H-Indol-3-yl)ethyl]docosanamide,2TBDMS,isomer #1CCCCCCCCCCCCCCCCCCCCCC(=O)N(CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C4584.5Semi standard non polar33892256
N-[2-(1H-Indol-3-yl)ethyl]docosanamide,2TBDMS,isomer #1CCCCCCCCCCCCCCCCCCCCCC(=O)N(CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C4247.5Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-[2-(1H-Indol-3-yl)ethyl]docosanamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0knc-4982000000-cce4fab63b052d5f78982017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-[2-(1H-Indol-3-yl)ethyl]docosanamide 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 - N-[2-(1H-Indol-3-yl)ethyl]docosanamide 10V, Positive-QTOFsplash10-0a59-0900300000-6241c15c1e1fd52e117e2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-[2-(1H-Indol-3-yl)ethyl]docosanamide 20V, Positive-QTOFsplash10-0a4l-0900000000-3029f69c64d4dbbf6ef22016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-[2-(1H-Indol-3-yl)ethyl]docosanamide 40V, Positive-QTOFsplash10-05nf-0910000000-14e6301673151119c0112016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-[2-(1H-Indol-3-yl)ethyl]docosanamide 10V, Negative-QTOFsplash10-001i-0101900000-0e4d2ce5acafa95af98e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-[2-(1H-Indol-3-yl)ethyl]docosanamide 20V, Negative-QTOFsplash10-001i-1916700000-e0b59a9c82dde9898ed62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-[2-(1H-Indol-3-yl)ethyl]docosanamide 40V, Negative-QTOFsplash10-0006-9512000000-400a7046c84d2974466b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-[2-(1H-Indol-3-yl)ethyl]docosanamide 10V, Positive-QTOFsplash10-001i-0600900000-fab309e1439087ba91e02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-[2-(1H-Indol-3-yl)ethyl]docosanamide 20V, Positive-QTOFsplash10-0006-0900100000-dfcd72de5e775f4bc13b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-[2-(1H-Indol-3-yl)ethyl]docosanamide 40V, Positive-QTOFsplash10-0006-2900000000-2a6b61b5bf9e62c01b1c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-[2-(1H-Indol-3-yl)ethyl]docosanamide 10V, Negative-QTOFsplash10-001i-0000900000-2f6f9482b7fa6d4c556e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-[2-(1H-Indol-3-yl)ethyl]docosanamide 20V, Negative-QTOFsplash10-001i-0400900000-19ea976d660afa5d73432021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-[2-(1H-Indol-3-yl)ethyl]docosanamide 40V, Negative-QTOFsplash10-015c-4911200000-4acca507be36a871691b2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDFDB018446
KNApSAcK IDC00026912
Chemspider ID8486510
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10311044
PDB IDNot Available
ChEBI ID166545
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.. .