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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2017-11-21 17:43:26 UTC
Update Date2019-07-23 14:38:55 UTC
HMDB IDHMDB0240244
Secondary Accession NumbersNone
Metabolite Identification
Common NameTemelastine
DescriptionTemelastine, also known as sk&f 93944 or SK and F-93944, belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. Temelastine is a very strong basic compound (based on its pKa). In humans, temelastine is involved in temelastine h1-antihistamine action. Temelastine is a second-generation H1-antihistamine.
Structure
Data?1563892735
Synonyms
ValueSource
SK&F 93944HMDB
SK And F 93944HMDB
SK And F-93944HMDB
SKF 93944HMDB
TemelastineHMDB
Chemical FormulaC21H24BrN5O
Average Molecular Weight442.361
Monoisotopic Molecular Weight441.116423
IUPAC Name2-{[4-(5-bromo-3-methylpyridin-2-yl)butyl]amino}-5-[(6-methylpyridin-3-yl)methyl]-3,4-dihydropyrimidin-4-one
Traditional Nametemelastine
CAS Registry Number86181-42-2
SMILES
CC1=CC=C(CC2=CN=C(NCCCCC3=C(C)C=C(Br)C=N3)NC2=O)C=N1
InChI Identifier
InChI=1S/C21H24BrN5O/c1-14-9-18(22)13-25-19(14)5-3-4-8-23-21-26-12-17(20(28)27-21)10-16-7-6-15(2)24-11-16/h6-7,9,11-13H,3-5,8,10H2,1-2H3,(H2,23,26,27,28)
InChI KeyOGEAASSLWZDQBM-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentPyrimidones
Alternative Parents
Substituents
  • Aminopyrimidine
  • Pyrimidone
  • Secondary aliphatic/aromatic amine
  • Methylpyridine
  • Aryl bromide
  • Aryl halide
  • Hydropyrimidine
  • Pyridine
  • Heteroaromatic compound
  • Lactam
  • Secondary amine
  • Azacycle
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organobromide
  • Organohalogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Process

Naturally occurring process:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.28ALOGPS
logP3.22ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)8.06ChemAxon
pKa (Strongest Basic)5.61ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area79.27 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity113.06 m³·mol⁻¹ChemAxon
Polarizability44.46 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0220900000-27c0d49a67eb91895cdcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-016u-1690400000-9dee478c37683ce817b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-3920000000-0f648f74ca0e74e53c94Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0033900000-029790136c989f2000b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014l-2291200000-31713515fbafc306f1c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-8930000000-a685d36f6382eb65e67bSpectrum
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 ID50101
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound55482
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Adam K, Oswald I: No effects on sleep of a histamine H1-receptor antagonist: temelastine. Br J Clin Pharmacol. 1986 Dec;22(6):718-20. [PubMed:2882773 ]