CHEBI:43966 - melagatran

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name melagatran
ChEBI ID CHEBI:43966
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:73114
Supplier Information
Download Molfile XML SDF
Formula C22H31N5O4
Net Charge 0
Average Mass 429.51260
Monoisotopic Mass 429.23760
InChI InChI=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
InChIKey DKWNMCUOEDMMIN-PKOBYXMFSA-N
SMILES [H][C@]1(CCN1C(=O)[C@H](NCC(O)=O)C1CCCCC1)C(=O)NCc1ccc(cc1)C(N)=N
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): 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(s): anticoagulant
An agent that prevents blood clotting.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 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 Sources
melagatran ChemIDplus
melagatrán WHO MedNet
mélagatran WHO MedNet
melagatranum WHO MedNet
Synonym Source
N-((R)-(((2S)-2-((-p-amidobenzyl)carbamoyl)-1-azetidinyl)carbonyl)cyclohexylmethyl)glycine ChemIDplus
Manual Xrefs Databases
D07143 KEGG DRUG
MEL PDBeChem
View more database links
Registry Numbers Types Sources
159776-70-2 CAS Registry Number KEGG DRUG
159776-70-2 CAS Registry Number ChemIDplus
8090770 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10102460 PubMed citation Europe PMC
11060733 PubMed citation Europe PMC
12846595 PubMed citation Europe PMC
13680847 PubMed citation Europe PMC
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16123912 PubMed citation Europe PMC
16767816 PubMed citation Europe PMC
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28338626 PubMed citation Europe PMC
9459334 PubMed citation Europe PMC
Last Modified
03 April 2017