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Substance Name: Pepstatin [USAN:INN]
RN: 26305-03-3
UNII: V6Y2T27Q1U
InChIKey: FAXGPCHRFPCXOO-LXTPJMTPSA-N

Note

  • Inhibits the aspartic protease endothiapepsin.

Molecular Formula

  • C34-H63-N5-O9

Molecular Weight

  • 685.8977
 

Classification Codes

  • Anti-Infective Agents
  • Antimalarials
  • Antiparasitic Agents
  • Antiprotozoal Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitor (Pepsin)
  • Enzyme Inhibitors
  • Natural Product
  • Protease Inhibitors
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Names and Synonyms

Name of Substance

  • Pepstatin
  • Pepstatin [USAN:INN]

Synonyms

  • Ahpatinin C
  • BRN 2201362
  • EINECS 247-600-0
  • Heptanoic acid, N-(3-methyl-1-oxobutyl)-L-valyl-L-valyl-(3S,4S)-3-hydroxy-6-methyl-4-aminoheptanoyl-L-alanyl-(3S,4S)-3-hydroxy-6-methyl-4-amino-
  • N-(3-Methyl-1-oxobutyl)-L-valyl-L-valyl-4-amino-3-hydroxy-6-methylheptanoyl-L-alanyl-4-amino-3-hydroxy-6-methylheptanoic acid
  • N-Isovaleryl-L-valyl-L-valyl-3-hydroxy-6-methyl-gamma-aminoheptanoyl-L-alanyl-3-hydroxy-6-methyl-gamma-aminoheptanoic acid
  • NSC 272671
  • Pepsin inhibitor S 735A
  • Pepstatin
  • Pepstatin A
  • Pepstatina
  • Pepstatina [INN-Spanish]
  • Pepstatine
  • Pepstatine [INN-French]
  • Pepstatinum
  • Pepstatinum [INN-Latin]
  • Procidin S 735A
  • UNII-V6Y2T27Q1U

Systematic Names

  • L-Alaninamide, N-(3-methyl-1-oxobutyl)-L-valyl-(3S,4S)-4-amino-3-hydroxy-6-methylheptanoyl-N-((1S)-1-((1S)-2-carboxy-1-hydroxyethyl)-3-methylbutyl)-
  • L-Valinamide, N-(3-methyl-1-oxobutyl)-L-valyl-N-(4-((2-((1-(2-carboxy-1-hydroxyethyl)-3-methylbutyl)amino)-1-methyl-2-oxoethyl)amino)-2-hydroxy-1-(2-methylpropyl)-4-oxobutyl)-, (1S-(1R*,2R*,4(R*(R*(R*)))))-
  • Pepstatin
  • Pepstatin A

Registry Numbers

CAS Registry Number

  • 26305-03-3

FDA UNII

  • V6Y2T27Q1U

Other Registry Number

  • 26368-29-6

System Generated Number

  • 0026305033

Structure Descriptors

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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intraperitoneal 450mg/kg (450mg/kg)   Journal of Antibiotics. Vol. 23, Pg. 259, 1970.
dog LD50 oral > 2gm/kg (2000mg/kg)   Journal of Antibiotics. Vol. 23, Pg. 259, 1970.
mouse LD50 intraperitoneal 1090mg/kg (1090mg/kg)   Journal of Antibiotics. Vol. 23, Pg. 259, 1970.
mouse LD50 oral > 2gm/kg (2000mg/kg)   Proceedings of the International Symposium of the Princess Takamatsu Cancer Research Fund. Vol. 6, Pg. 57, 1976.
rabbit LD50 intraperitoneal 820mg/kg (820mg/kg)   Journal of Antibiotics. Vol. 23, Pg. 259, 1970.
rabbit LD50 oral > 2gm/kg (2000mg/kg)   Journal of Antibiotics. Vol. 23, Pg. 259, 1970.
rat LD50 intraperitoneal 875mg/kg (875mg/kg)   Journal of Antibiotics. Vol. 23, Pg. 259, 1970.
rat LD50 oral > 2gm/kg (2000mg/kg)   Proceedings of the International Symposium of the Princess Takamatsu Cancer Research Fund. Vol. 6, Pg. 57, 1976.