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

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ChEBI Name Ac-(D)Phe-Pro-boroArg-OH
ChEBI ID CHEBI:42142
ChEBI ASCII Name Ac-(D)Phe-Pro-boroArg-OH
Definition A 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boronic acid petide that is N-acetyl-D-phenylalanyl-L-prolyl-L-arginine in which the C-termnal carboxy group has been replaced by a borono (-B(OH)2) group.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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C21H33BN6O5
Net Charge 0
Average Mass 460.336
Monoisotopic Mass 460.26055
InChI InChI=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
InChIKey FXFYPTZERULUBS-SQNIBIBYSA-N
SMILES N([C@@H](CCCNC(N)=N)B(O)O)C(=O)[C@@H]1CCCN1C([C@@H](CC2=CC=CC=C2)NC(C)=O)=O
Roles Classification
Chemical Role(s): 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).
Application(s): anticoagulant
An agent that prevents blood clotting.
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ChEBI Ontology
Outgoing 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 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-boroarginine ChemIDplus
Manual Xref Database
DP7 PDBeChem
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Registry Numbers Types Sources
130982-43-3 CAS Registry Number ChemIDplus
24287151 Reaxys Registry Number Reaxys
Last Modified
05 April 2018