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CHEBI:43966 - melagatran

ChEBI IDCHEBI:43966
ChEBI Namemelagatran
Stars
DefinitionA 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.
Secondary ChEBI IDCHEBI:73114
Last Modified3 April 2017
SubmitterGareth Owen
DownloadsMolfile
FormulaC22H31N5O4
Net Charge0
Average Mass429.521
Monoisotopic Mass429.23760
SMILES[H][C@@]1(C(=O)NCc2ccc(C(=N)N)cc2)CCN1C(=O)[C@H](NCC(=O)O)C1CCCCC1
InChIInChI=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
InChIKeyDKWNMCUOEDMMIN-PKOBYXMFSA-N
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
EC 3.4.21.5 (thrombin) inhibitor  An EC 3.4.21.* (serine endopeptidase) inhibitor that interferes with the action of thrombin (EC 3.4.21.5).
serine protease inhibitor  Any protease inhibitor that restricts the action of a serine protease.
Application:
anticoagulant  An agent that prevents blood clotting.
ChEBI Ontology
Outgoing Relation(s)
melagatran (CHEBI:43966) has role anticoagulant (CHEBI:50249)
melagatran (CHEBI:43966) has role EC 3.4.21.5 (thrombin) inhibitor (CHEBI:65232)
melagatran (CHEBI:43966) has role serine protease inhibitor (CHEBI:64926)
melagatran (CHEBI:43966) is a azetidines (CHEBI:38777)
melagatran (CHEBI:43966) is a carboxamidine (CHEBI:35359)
melagatran (CHEBI:43966) is a dicarboxylic acid monoamide (CHEBI:35735)
melagatran (CHEBI:43966) is a non-proteinogenic α-amino acid (CHEBI:83925)
melagatran (CHEBI:43966) is a secondary amino compound (CHEBI:50995)
Incoming Relation(s)
ximelagatran (CHEBI:65172) has functional parent melagatran (CHEBI:43966)
IUPAC Name 
N-[(1R)-2-{(2S)-2-[(4-carbamimidoylbenzyl)carbamoyl]azetidin-1-yl}-1-cyclohexyl-2-oxoethyl]glycine
INNs  Source
mélagatranWHO MedNet
melagatranChemIDplus
melagatránWHO MedNet
melagatranumWHO MedNet
Synonym  Source
N-((R)-(((2S)-2-((-p-amidobenzyl)carbamoyl)-1-azetidinyl)carbonyl)cyclohexylmethyl)glycineChemIDplus
Manual XrefsDatabases
D07143KEGG DRUG
MELPDBeChem
Registry NumbersSources
Reaxys:8090770Reaxys
CAS:159776-70-2ChemIDplus
CAS:159776-70-2KEGG DRUG
Citations