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CHEBI:59173 - bivalirudin

ChEBI IDCHEBI:59173
ChEBI Namebivalirudin
Stars
DefinitionA synthetic peptide of 20 amino acids, comprising D-Phe, Pro, Arg, Pro, Gly, Gly, Gly, Gly, Asn, Gly, Asp, Phe, Glu, Glu, Ile, Pro, Glu, Glu, Tyr, and Leu in sequence. A congener of hirudin (a naturally occurring drug found in the saliva of the medicinal leech), it a specific and reversible inhibitor of thrombin, and is used as an anticoagulant.
Last Modified3 April 2018
SubmitterGareth Owen
DownloadsMolfile
FormulaC98H138N24O33
Net Charge0
Average Mass2180.317
Monoisotopic Mass2178.98581
SMILESCC[C@H](C)[C@H](NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CC(=O)O)NC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)CNC(=O)CNC(=O)CNC(=O)CNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H]1CCCN1C(=O)[C@H](N)Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)N[C@@H](CC(C)C)C(=O)O
InChIInChI=1S/C98H138N24O33/c1-5-52(4)82(96(153)122-39-15-23-70(122)92(149)114-60(30-34-79(134)135)85(142)111-59(29-33-78(132)133)86(143)116-64(43-55-24-26-56(123)27-25-55)89(146)118-67(97(154)155)40-51(2)3)119-87(144)61(31-35-80(136)137)112-84(141)58(28-32-77(130)131)113-88(145)63(42-54-18-10-7-11-19-54)117-90(147)66(45-81(138)139)110-76(129)50-107-83(140)65(44-71(100)124)109-75(128)49-106-73(126)47-104-72(125)46-105-74(127)48-108-91(148)68-21-13-38-121(68)95(152)62(20-12-36-103-98(101)102)115-93(150)69-22-14-37-120(69)94(151)57(99)41-53-16-8-6-9-17-53/h6-11,16-19,24-27,51-52,57-70,82,123H,5,12-15,20-23,28-50,99H2,1-4H3,(H2,100,124)(H,104,125)(H,105,127)(H,106,126)(H,107,140)(H,108,148)(H,109,128)(H,110,129)(H,111,142)(H,112,141)(H,113,145)(H,114,149)(H,115,150)(H,116,143)(H,117,147)(H,118,146)(H,119,144)(H,130,131)(H,132,133)(H,134,135)(H,136,137)(H,138,139)(H,154,155)(H4,101,102,103)/t52-,57+,58-,59-,60-,61-,62-,63-,64-,65-,66-,67-,68-,69-,70-,82-/m0/s1
InChIKeyOIRCOABEOLEUMC-GEJPAHFPSA-N
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Role:
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).
Application:
anticoagulant  An agent that prevents blood clotting.
ChEBI Ontology
Outgoing Relation(s)
bivalirudin (CHEBI:59173) has role anticoagulant (CHEBI:50249)
bivalirudin (CHEBI:59173) has role EC 3.4.21.5 (thrombin) inhibitor (CHEBI:65232)
bivalirudin (CHEBI:59173) is a polypeptide (CHEBI:15841)
IUPAC Name 
D-phenylalanyl-L-prolyl-L-arginyl-L-prolylglycylglycylglycylglycyl-L-asparaginylglycyl-L-α-aspartyl-L-phenylalanyl-L-α-glutamyl-L-α-glutamyl-L-isoleucyl-L-prolyl-L-α-glutamyl-L-alpha-glutamyl-L-tyrosyl-L-leucine
INN  Source
bivalirudinChemIDplus
Synonyms  Source
(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-4-amino-2-[[2-[[2-[[2-[[2-[[(2S)-1-[(2S)-2-[[(2S)-1-[(2R)-2-amino-3-cyclohexylpropanoyl]pyrrolidine-2-carbonyl]amino]-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]acetyl]amino]acetyl]amino]acetyl]amino]acetyl]amino]-4-oxobutanoyl]amino]acetyl]amino]-4-hydroxy-4-oxobutanoyl]amino]-3-cyclohexylpropanoyl]amino]-5-hydroxy-5-oxopentanoyl]amino]-5-hydroxy-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbonyl]amino]-5-hydroxy-5-oxopentanoyl]amino]-5-hydroxy-5-oxopentanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-methylpentanoic acidDrugBank
bivalirudinaChEBI
bivalirudineChEBI
bivalirudinumChEBI
Manual XrefsDatabases
DB00006DrugBank
WO9102750Patent
385DrugCentral
Registry NumbersSources
Beilstein:12004535Beilstein
CAS:128270-60-0ChemIDplus
Citations