CHEBI:7989 - pepstatin A

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ChEBI Name pepstatin A
ChEBI ID CHEBI:7989
Definition A pentapeptide isolated from Streptomyces testaceus. It is a potent inhibitor of aspartyl proteases.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:43324
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Formula C34H63N5O9
Net Charge 0
Average Mass 685.904
Monoisotopic Mass 685.46258
InChI InChI=1S/C34H63N5O9/c1-17(2)12-23(37-33(47)31(21(9)10)39-34(48)30(20(7)8)38-27(42)14-19(5)6)25(40)15-28(43)35-22(11)32(46)36-24(13-18(3)4)26(41)16-29(44)45/h17-26,30-31,40-41H,12-16H2,1-11H3,(H,35,43)(H,36,46)(H,37,47)(H,38,42)(H,39,48)(H,44,45)/t22-,23-,24-,25-,26-,30-,31-/m0/s1
InChIKey FAXGPCHRFPCXOO-LXTPJMTPSA-N
SMILES CC(C)C[C@H](NC(=O)[C@H](C)NC(=O)C[C@H](O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CC(C)C)C(C)C)C(C)C)[C@@H](O)CC(O)=O
Metabolite of Species Details
Streptomyces testaceus (NCBI:txid1883) See: DOI
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
EC 3.4.23.* (aspartic endopeptidase) inhibitor
An EC 3.4.* (hydrolases acting on peptide bond) inhibitor that interferes with the action of any aspartic endopeptidase (EC 3.4.23.*).
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ChEBI Ontology
Outgoing pepstatin A (CHEBI:7989) has role bacterial metabolite (CHEBI:76969)
pepstatin A (CHEBI:7989) has role EC 3.4.23.* (aspartic endopeptidase) inhibitor (CHEBI:76885)
pepstatin A (CHEBI:7989) is a pentapeptide (CHEBI:48545)
pepstatin A (CHEBI:7989) is a secondary carboxamide (CHEBI:140325)
pepstatin A (CHEBI:7989) is conjugate acid of pepstatin A(1−) (CHEBI:190525)
Incoming pepstatin A(1−) (CHEBI:190525) is conjugate base of pepstatin A (CHEBI:7989)
IUPAC Name
N-(3-methylbutanoyl)-L-valyl-N-[(3S,4S)-1-{[(2S)-1-{[(2S,3S)-1-carboxy-2-hydroxy-5-methylhexan-3-yl]amino}-1-oxopropan-2-yl]amino}-3-hydroxy-6-methyl-1-oxoheptan-4-yl]-L-valinamide
INNs Sources
pepstatin WHO MedNet
pepstatina WHO MedNet
pepstatine WHO MedNet
pepstatinum WHO MedNet
Synonyms Sources
(3S,4S)-3-hydroxy-4-[(2S)-2-[(3S,4S)-3-hydroxy-6-methyl-4-[(2S)-3-methyl-2-[(2S)-3-methyl-2-(3-methylbutanamido)butanamido]butanamido]heptanamido]propanamido]-6-methylheptanoic acid IUPAC
ahpatinin C ChemIDplus
pepsin inhibitor S 735A ChemIDplus
procidin S 735A ChemIDplus
Manual Xrefs Databases
C00018785 KNApSAcK
C00773 KEGG COMPOUND
D03818 KEGG DRUG
IHN PDBeChem
LSM-2282 LINCS
Pepstatin Wikipedia
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Registry Numbers Types Sources
2201362 Reaxys Registry Number Reaxys
26305-03-3 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
24 September 2020