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CHEBI:42142 - Ac-(D)Phe-Pro-boroArg-OH

ChEBI IDCHEBI:42142
ChEBI NameAc-(D)Phe-Pro-boroArg-OH
Stars
ASCII NameAc-(D)Phe-Pro-boroArg-OH
DefinitionA C-terminal boronic acid petide that is N-acetyl-D-phenylalanyl-L-prolyl-L-arginine in which the C-termnal carboxy group has been replaced by a borono (-B(OH)2) group. A thrombin (Factor IIa) inhibitor, thereby acting as an anticoagulant.
Last Modified5 April 2018
DownloadsMolfile
FormulaC21H33BN6O5
Net Charge0
Average Mass460.344
Monoisotopic Mass460.26055
SMILESCC(=O)N[C@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCNC(=N)N)B(O)O
InChIInChI=1S/C21H33BN6O5/c1-14(29)26-16(13-15-7-3-2-4-8-15)20(31)28-12-6-9-17(28)19(30)27-18(22(32)33)10-5-11-25-21(23)24/h2-4,7-8,16-18,32-33H,5-6,9-13H2,1H3,(H,26,29)(H,27,30)(H4,23,24,25)/t16-,17+,18+/m1/s1
InChIKeyFXFYPTZERULUBS-SQNIBIBYSA-N
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
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)
Ac-(D)Phe-Pro-boroArg-OH (CHEBI:42142) has role anticoagulant (CHEBI:50249)
Ac-(D)Phe-Pro-boroArg-OH (CHEBI:42142) has role EC 3.4.21.5 (thrombin) inhibitor (CHEBI:65232)
Ac-(D)Phe-Pro-boroArg-OH (CHEBI:42142) is a acetamides (CHEBI:22160)
Ac-(D)Phe-Pro-boroArg-OH (CHEBI:42142) is a C-terminal boronic acid peptide (CHEBI:140517)
Ac-(D)Phe-Pro-boroArg-OH (CHEBI:42142) is a guanidines (CHEBI:24436)
Ac-(D)Phe-Pro-boroArg-OH (CHEBI:42142) is conjugate base of Ac-(D)Phe-Pro-boroArg-OH(1+) (CHEBI:140518)
Incoming Relation(s)
Ac-(D)Phe-Pro-boroArg-OH(1+) (CHEBI:140518) is conjugate acid of Ac-(D)Phe-Pro-boroArg-OH (CHEBI:42142)
IUPAC Name 
N-acetyl-D-phenylalanyl-N-[(1R)-1-borono-4-carbamimidamidobutyl]-L-prolinamide
Synonym  Source
acetylphenylalanyl-prolyl-boroarginineChemIDplus
Manual XrefsDatabases
DP7PDBeChem
Registry NumbersSources
Reaxys:24287151Reaxys
CAS:130982-43-3ChemIDplus