ximelagatran   

GtoPdb Ligand ID: 6381

Synonyms: H 376-95 | H 376/95
Compound class: Synthetic organic
Comment: Applications for approval of ximelagatran were withdrawn in 2006.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 8
Hydrogen bond donors 4
Rotatable bonds 13
Topological polar surface area 146.35
Molecular weight 473.26
XLogP 2.39
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES CCOC(=O)CNC(C(=O)N1CCC1C(=O)NCc1ccc(cc1)C(=NO)N)C1CCCCC1
Isomeric SMILES CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCc1ccc(cc1)/C(=N/O)/N)C1CCCCC1
InChI InChI=1S/C24H35N5O5/c1-2-34-20(30)15-26-21(17-6-4-3-5-7-17)24(32)29-13-12-19(29)23(31)27-14-16-8-10-18(11-9-16)22(25)28-33/h8-11,17,19,21,26,33H,2-7,12-15H2,1H3,(H2,25,28)(H,27,31)/t19-,21+/m0/s1
InChI Key ZXIBCJHYVWYIKI-PZJWPPBQSA-N
Classification
Compound class Synthetic organic
Is prodrug? Yes
Active form melagatran
IUPAC Name
ethyl 2-[[(1R)-1-cyclohexyl-2-[(2S)-2-[[4-(N'-hydroxycarbamimidoyl)phenyl]methylcarbamoyl]azetidin-1-yl]-2-oxoethyl]amino]acetate
International Nonproprietary Names
INN number INN
8037 ximelagatran
Synonyms
H 376-95 | H 376/95
Database Links
CAS Registry No. 192939-46-1 (source: PubChem)
ChEBI CHEBI:65172
ChEMBL Ligand CHEMBL522038
DrugBank Ligand DB04898
DrugCentral Ligand 2852
GtoPdb PubChem SID 178102999
PubChem CID 9574101
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Search UniChem for chemical match using the InChIKey ZXIBCJHYVWYIKI-PZJWPPBQSA-N
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Wikipedia Ximelagatran