Basic information
- CAS
26305-03-3- Standard SMILES
CC(C)CC(=O)NC(C(=O)NC(C(=O)NC(CC(C)C)C(O)CC(=O)NC(C)C(=O)NC(CC(C)C)C(O)CC(=O)O)C(C)C)C(C)C- InChIKey
FAXGPCHRFPCXOO-UHFFFAOYSA-N- Molecular formula
- C34H63N5O9
- Average molar mass
- 685.9 g/mol
- Monoisotopic mass
- 685.4625786
Overview
See also: Pepstatin (annotation moved to).
Names & identifiers
- Preferred name
- 3-Hydroxy-4-[2-[[3-hydroxy-6-methyl-4-[[3-methyl-2-[[3-methyl-2-(3-methylbutanoylamino)butanoyl]amino]butanoyl]amino]heptanoyl]amino]propanoylamino]-6-methyl-heptanoic acid
- IUPAC
- 3-hydroxy-4-[2-[[3-hydroxy-6-methyl-4-[[3-methyl-2-[[3-methyl-2-(3-methylbutanoylamino)butanoyl]amino]butanoyl]amino]heptanoyl]amino]propanoylamino]-6-methylheptanoic acid
- English name
- Pepstatin
- Molecular formula
- C34H63N5O9
- Molecular weight
- 685.89
Names & synonyms
C34H63N5O939324-30-6N-(3-Methyl-1-oxobutyl)-L-valyl-L-valyl-4-amino-3-hydroxy-6-methylheptanoyl-L-alanyl-4-amino-3-hydroxy-6-methylheptanoic acidCHEMBL38526SCHEMBL19665773pepstatin A ~120'000 U/mgHMS3374B07HMS3745M07IPA-4397-Vs73813-hydroxy-4-[2-[[3-hydroxy-6-methyl-4-[[3-methyl-2-[[3-methyl-2-(3-methylbutanoylamino)butanoyl]amino]butanoyl]amino]heptanoyl]amino]propanoylamino]-6-methyl-heptanoic acidHeptanoic acid, N-(3-methyl-1-oxobutyl)-L-valyl-L-valyl-4-amino-3-hydroxy-6-methylheptanoyl-L-alanyl-4-amino-3-hydroxy-6-methyl-
Show more names
PEPSTATIN AIVA-VAL-VAL-STA-ALA-STAISOVALERYL-VAL-VAL-STA-ALA-STA-OH(3S,4S)-4-AMINO-3-HYDROXY-6-METHYL-HEPTANOIC ACIDCPSDCLN10PEPSTATINPepstainAahpatinincHEL-S-130P
Isovaleryl-L-Valyl-L-Valyl[(3S,4S)-4-Amino-3-Hydroxy-6-Methylheptanoyl]-L-Alanyl [(3S,4S)-4-Amino-3-Hydroxy-6-Methylheptanoic Acid]
Properties
Computed structural properties
- XLogP
- 3
- Topological polar surface area
- 223 Ų
- Hydrogen bond donors
- 8
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 22
- Heavy atoms
- 48
- Formal charge
- 0
- Complexity
- 1,060
Physicochemical properties
- Melting point
- 233 °C · 233 °C (dec.)(lit.)
- alpha
- 27 · D27 -90.3° (c = 0.288 in methanol)
- Boiling point
- 695.91 °C · 695.91°C (rough estimate)
- Density
- 1.134 · 1.1340 (rough estimate)
- refractive index
- 1.75 · 1.7500 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- 10 % · 10% acetic acid in methanol: 1 mg/mL
- form
- White solid
- pka
- 4.17 · 4.17±0.10(Predicted)
- color
- Colorless needles
- optical activity
- -90 · Optical rotation: -90.0 ± 5° (c = 0.5, MeOH, 20°C).
- biological source
- synthetic
- Water Solubility
- 10 % · It is soluble in 10% (v/v) acetic acid in methanol (9:1 methanol:acetic acid) (1 mg/ml), ethanol (1-2 mg/ml with heat up to 60°C), DMSO (5 mg/ml), methanol (1 mg/ml), and acetic acid. Insoluble in benzene, chloroform, water, 1 M NaOH, and ether.
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 10
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 2
- rtecs
- SC6155000
- hs_code
- 29241990
- Toxicity
- LD50 in mice, rats, rabbits, dogs (mg/kg): 1090, 875, 820, 450 i.p.; all >2000 orally (Umezawa, 1970)
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Applications
DescriptionPepstatin A is a bacterial-derived chemotactic pentapeptide that irreversibly inhibits aspartic proteases, including pepsin, gastricsin, renin, cathepsin E, and cathepsin D. Pepstatin A has been reported to stimulate human neutrophil degranulation (EC50 = 0.75 μM) and super oxide production (EC50 = 1.5 μM). Pepstatin A has been widely used as a research tool in studies of protease mechanisms and biological functions and has been examined as a therapeutic agent for inflammatory conditions including gastric ulcer, edema, and hypertension.
UsesAntiviral;Aspartic proteases irreversible inhibitor
UsesPepstatin A are natural, statine-containing peptides that acts as inhibitor of aspartic protease enzymes.
UsesAs an aspartic proteases irreversible inhibitor, Pepstain A can be used in conjunction with E64-d and Leupeptin A to inhibit the degradation of autophagic cargo inside autophagosomes.
General DescriptionPepstatin A is a naturally occurring chemotactic peptide and inhibitor of aspartic proteases that was initially isolated from culture filtrates of various Actinomycetes species, with the initial name simply of “pepstatin”. This name was later modified to “pepstatin A” to distinguish the original pepstatin from later derivatives. Pepstatin A notably contains the unusual amino acid 4-amino-hydroxy-6-methylheptanoic acid (AHMHA), which is known also as statine. The amino acid sequence of pepstatin A is N-Isovaleryl-L-Valyl-L-Valyl-AHMHA-L-Alanyl-AHMHA.
Upstream & downstream products
Upstream raw materials
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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