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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-11-21 17:42:22 UTC
Update Date2022-03-07 03:18:14 UTC
HMDB IDHMDB0240240
Secondary Accession NumbersNone
Metabolite Identification
Common NameLatrepirdine
DescriptionLatrepirdine belongs to the class of organic compounds known as n-alkylindoles. N-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 1-position. In humans, latrepirdine is involved in the latrepirdine h1-antihistamine action pathway. Latrepirdine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Latrepirdine.
Structure
Data?1563892735
Synonyms
ValueSource
DimebolinHMDB
DimebolineHMDB
DimebonHMDB, MeSH
DimeboneHMDB, MeSH
Preparation 84HMDB
LatrepirdineHMDB
Chemical FormulaC21H25N3
Average Molecular Weight319.452
Monoisotopic Molecular Weight319.204847817
IUPAC Name5-(2-{2,8-dimethyl-1H,2H,3H,4H,5H-pyrido[4,3-b]indol-5-yl}ethyl)-2-methylpyridine
Traditional Namelatrepirdine
CAS Registry Number3613-73-8
SMILES
CN1CCC2=C(C1)C1=CC(C)=CC=C1N2CCC1=CC=C(C)N=C1
InChI Identifier
InChI=1S/C21H25N3/c1-15-4-7-20-18(12-15)19-14-23(3)10-9-21(19)24(20)11-8-17-6-5-16(2)22-13-17/h4-7,12-13H,8-11,14H2,1-3H3
InChI KeyJNODQFNWMXFMEV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-alkylindoles. N-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 1-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassN-alkylindoles
Direct ParentN-alkylindoles
Alternative Parents
Substituents
  • 3-alkylindole
  • N-alkylindole
  • Indole
  • Methylpyridine
  • Aralkylamine
  • Pyridine
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Amine
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Process

Naturally occurring process:

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
logP3.52ALOGPS
logP3.41ChemAxon
logS-4.3ALOGPS
pKa (Strongest Basic)7.17ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area21.06 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity100.72 m³·mol⁻¹ChemAxon
Polarizability38.6 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+178.88531661259
AllCCS[M-H]-187.61431661259
DeepCCS[M+H]+177.34930932474
DeepCCS[M-H]-174.99130932474
DeepCCS[M-2H]-208.55130932474
DeepCCS[M+Na]+183.77830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LatrepirdineCN1CCC2=C(C1)C1=CC(C)=CC=C1N2CCC1=CC=C(C)N=C13706.4Standard polar33892256
LatrepirdineCN1CCC2=C(C1)C1=CC(C)=CC=C1N2CCC1=CC=C(C)N=C12786.4Standard non polar33892256
LatrepirdineCN1CCC2=C(C1)C1=CC(C)=CC=C1N2CCC1=CC=C(C)N=C12870.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Latrepirdine 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 - Latrepirdine 10V, Positive-QTOFsplash10-00di-0119000000-912c132b0c377d70b0b32017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Latrepirdine 20V, Positive-QTOFsplash10-00fr-1492000000-e074b38ea87239a8c2922017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Latrepirdine 40V, Positive-QTOFsplash10-00di-3900000000-abbbe3dcbd3e543a23a82017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Latrepirdine 10V, Negative-QTOFsplash10-014i-0009000000-71b046122676d3980bbc2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Latrepirdine 20V, Negative-QTOFsplash10-014j-4619000000-407ed46cd6f2005b65402017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Latrepirdine 40V, Negative-QTOFsplash10-0032-0900000000-89c2c2376cf7c27583892017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Latrepirdine 10V, Negative-QTOFsplash10-014i-0009000000-f70ad12b32e54f9e7e5e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Latrepirdine 20V, Negative-QTOFsplash10-014i-0119000000-51575273a5c6e505932e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Latrepirdine 40V, Negative-QTOFsplash10-0002-0900000000-889aeb417b06e468c4d62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Latrepirdine 10V, Positive-QTOFsplash10-00di-0029000000-1a06bc7ad64cfd4a3cf32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Latrepirdine 20V, Positive-QTOFsplash10-00fr-0296000000-a86db90723380799de1e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Latrepirdine 40V, Positive-QTOFsplash10-00di-4930000000-a84c3182acd7a67506cf2021-09-22Wishart 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 IDDB11725
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID170644
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLatrepirdine
METLIN IDNot Available
PubChem Compound197033
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. Montgomery LC, Deuster PA: Effects of antihistamine medications on exercise performance. Implications for sportspeople. Sports Med. 1993 Mar;15(3):179-95. [PubMed:7680815 ]