Pepstatin A

Category	HIV Protease
CAS	26305-03-3
Description	Pepstatin A is a potent aspartic protease inhibitor, and also inhibits HIV replication.It is a hexa-peptide containing the unusual amino acid statine (Sta, (3S,4S)-4-amino-3-hydroxy-6-methylheptanoic acid), having the sequence Isovaleryl-Val-Val-Sta-Ala-Sta (Iva-Val-Val-Sta-Ala-Sta).

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Product Information

Synonyms	Pepstatin; NSC 272671; NSC-272671; NSC272671; Pepstatin A; Pepstatina; Pepstatinum; Pepstatin A
IUPAC Name	(3S,4S)-3-hydroxy-4-[[(2S)-2-[[(3S,4S)-3-hydroxy-6-methyl-4-[[(2S)-3-methyl-2-[[(2S)-3-methyl-2-(3-methylbutanoylamino)butanoyl]amino]butanoyl]amino]heptanoyl]amino]propanoyl]amino]-6-methylheptanoic acid
Molecular Weight	685.89
Molecular Formula	C34H63N5O9
Canonical SMILES	CC(C)CC(C(CC(=O)O)O)NC(=O)C(C)NC(=O)CC(C(CC(C)C)NC(=O)C(C(C)C)NC(=O)C(C(C)C)NC(=O)CC(C)C)O
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
Boiling Point	997.6°C at 760 mmHg
Melting Point	233°C (dec.)(lit.)
Flash Point	557.1±34.3 °C
Purity	>98%
Density	1.117 g/cm3
Solubility	In vitro: 10 mM in DMSO
Appearance	White Solid
Application	Protease Inhibitors
Storage	Store at -20°C
Complexity	1060
Exact Mass	685.46257860
Index Of Refraction	1.504
In Vitro	Pepstatin is a specific acid protease inhibitor produced by actinomycetes, with IC50s of 4.5 nM, 6.2 nM, 150 nM, 290 nM, 520 nM and 260 nM for hemoglobin-pepsin, hemoglobin-proctase, casein-pepsin, casein-proctase, casein-acid protease and hemoglobin-acid protease, respectively. Pepstatin (Pepstatin A) inhibits the recombinant HIV protease with an IC50 of 250 μM. Pepstatin shows no effect on cellular protein synthesis and probably does not exert severe cell toxicity.
In Vivo	Pepstatin has a very low toxicity, with LD50s of 1090 mg/kg, 875 mg/kg, 820 mg/kg and 450 mg/kg for mice, rats, rabbits, and dogs by i.p. route, and > 2000 mg/kg for all species by oral route. Pepstatin (0.5-50 mg/kg, p.o.) suppresses stomach ulceration of the pylorus in ligated Shay rats.
PSA	223.26000
Target	IC50: 4.5 nM (Hemoglobin-pepsin), 6.2 nM (Hemoglobin-proctase), 150 nM (Casein-pepsin), 260 nM (Hemoglobin-acid protease), 290 nM (Casein-proctase), 520 nM (Casein-acid protease)
Vapor Pressure	0.0±0.6 mmHg at 25°C
XLogP3-AA	3