melagatran (CHEM044238)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 11:54:30 UTC
Update Date2016-11-09 01:23:05 UTC
Accession NumberCHEM044238
Identification
Common Namemelagatran
ClassSmall Molecule
DescriptionA member of the class of azetidines that is (2S)-azetidine 2-carboxylic acid in which the carboxylic acid has been converted to the amide corresponding to formal condensation with 4-(aminomethyl)benzenecarboximidamide and in which the hydrogen attached to the azetidine nitrogen is replaced by a (2R)-2-cyclohexyl-2-[(carboxymethyl)amino]acetyl group.
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
MelagatranumChEBI
N-((R)-(((2S)-2-((-p-Amidobenzyl)carbamoyl)-1-azetidinyl)carbonyl)cyclohexylmethyl)glycineChEBI
Chemical FormulaC22H31N5O4
Average Molecular Mass429.513 g/mol
Monoisotopic Mass429.238 g/mol
CAS Registry Number159776-70-2
IUPAC Name2-{[(1R)-2-[(2S)-2-{[(4-carbamimidoylphenyl)methyl]-C-hydroxycarbonimidoyl}azetidin-1-yl]-1-cyclohexyl-2-oxoethyl]amino}acetic acid
Traditional Namemelagatran
SMILES[H][C@@](NCC(O)=O)(C1CCCCC1)C(=O)N1CC[C@@]1([H])C(O)=NCC1=CC=C(C=C1)C(N)=N
InChI IdentifierInChI=1S/C22H31N5O4/c23-20(24)16-8-6-14(7-9-16)12-26-21(30)17-10-11-27(17)22(31)19(25-13-18(28)29)15-4-2-1-3-5-15/h6-9,15,17,19,25H,1-5,10-13H2,(H3,23,24)(H,26,30)(H,28,29)/t17-,19+/m0/s1
InChI KeyDKWNMCUOEDMMIN-PKOBYXMFSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • Alpha-amino acid amide
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • Monocyclic benzene moiety
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Amino acid or derivatives
  • Amino acid
  • Azetidine
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Amidine
  • Azacycle
  • Carboxylic acid amidine
  • Organoheterocyclic compound
  • Carboxylic acid
  • Secondary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Secondary amine
  • Carboximidamide
  • Carbonyl group
  • Organopnictogen compound
  • Organic nitrogen compound
  • Amine
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP-0.36ALOGPS
logP-2.9ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)2.67ChemAxon
pKa (Strongest Basic)11.49ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area152.1 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity126.22 m³·mol⁻¹ChemAxon
Polarizability46.35 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-0923400000-4cf5087051d819523790Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-1900000000-0c3260f1d0c0ad51131dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006t-4900000000-c2b89a474481ec3c69dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fvi-0390400000-4239a4f6a9064c684d0fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udj-2890100000-b75630b915b79292db10Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dj-9720000000-93f1276623796cf62519Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB13616
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkXimelagatran
Chemspider IDNot Available
ChEBI ID43966
PubChem Compound ID183797
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10102460
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11060733
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=12846595
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=13680847
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=15487959
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=16106594
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=16123912
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=16767816
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=22546231
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=28338626
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=9459334