Compound: Pepstatin A
SMILES: O=C(N[C@H](C(=O)N[C@H]([C@@H](O)CC(=O)N[C@H](C(=O)N[C@H]([C@@H](O)CC(=O)O)CC(C)C)C)CC(C)C)C(C)C)[C@@H](NC(=O)CC(C)C)C(C)C
InChIKey: FAXGPCHRFPCXOO-LXTPJMTPSA-N
Synonyms: Pepstatin A, pepstatin, 26305-03-3, Pepstatine, Pepstatina, Ahpatinin C, Pepstatinum, Procidin S 735A, Pepsin inhibitor S 735A, V6Y2T27Q1U, DTXSID7046095, NSC-272671, CHEBI:7989, (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, DTXCID5026095, N-Isovaleryl-L-valyl-L-valyl-3-hydroxy-6-methyl-gamma-aminoheptanoyl-L-alanyl-3-hydroxy-6-methyl-gamma-aminoheptanoic acid, NSC272671, (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, RefChem:860129, 247-600-0, Pepstatin (nonspecific), MFCD00060740, Pepstatin (VAN), CCRIS 3603, 39324-30-6, Iva-Val-Val-Sta-Ala-Sta-OH, MLS002222329, CHEMBL296588, (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, (6S,9S,12S,13S,17S,20S,21S)-13,21-dihydroxy-12,20-diisobutyl-6,9-diisopropyl-2,17-dimethyl-4,7,10,15,18-pentaoxo-5,8,11,16,19-pentaazatricosan-23-oic acid, L-Alaninamide,N-(3-methyl-1-oxobutyl)-L-valyl-L-valyl-(3S,4S)-4-amino-3-hydroxy-6-methylheptanoyl-N-[(1S)-1-[(1S)-2-carboxy-1-hydroxyethyl]-3-methylbutyl]-, NCGC00161670-06, C34H63N5O9, 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, N-(3-Methyl-1-oxobutyl)-L-valyl-L-valyl-(3S,4S)-4-amino-3-hydroxy-6-methylheptanoyl-N-[(1S)-1-[(1S)-2-carboxy-1-hydroxyethyl]-3-methylbutyl]-L-alaninamide, 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, N-[(3-Methyl-1-oxobutyl)-L-valyl-L-valyl-4-amino-3-hydroxy-6-methylheptanoyl-L-alanyl]-4-amino-3-hydroxy-6-methylheptanoic acid, SMR000059191, Pepstatin [USAN:INN], Pepstatine [INN-French], Pepstatinum [INN-Latin], Pepstatina [INN-Spanish], UNII-V6Y2T27Q1U, 1lyb, 1sme, 6apr, N-(3-Methyl-1-oxobutyl)-L-valyl-L-valyl-4-amino-3-hydroxy-6-methylheptanoyl-L-alanyl-4-amino-3-hydroxy-6-methylheptanoic acid, EINECS 247-600-0, CAS-26305-03-3, NSC 272671, BRN 2201362, 4er2, PEPSTATIN [INN], PEPSTATIN [MI], Pepstatin (USAN/INN), PEPSTATIN [USAN], Pepstatin A (Synthetic), Prestwick3_000405, Iva-Val-Val-Sta-Ala-Sta, UPCMLD-DP141, PEPSTATIN [WHO-DD], SCHEMBL50324, BDBM912, BSPBio_000330, BSPBio_001000, KBioGR_000340, KBioSS_000340, MLS000069747, MLS002207302, MLS006010748, BPBio1_000364, orb1303884, UPCMLD-DP141:001, UPCMLD-DP141:002, IPA-3998-PI, KBio2_000340, KBio2_002908, KBio2_005476, KBio3_000679, KBio3_000680, Bio1_000404, Bio1_000893, Bio1_001382, Bio2_000340, Bio2_000820, GLXC-23556, HMS1362B21, HMS1792B21, HMS1990B21, HMS2096A12, HMS2233I07, HMS3403B21, HMS3713A12, EX-A4027, HY-P0018, IPA-4397, Pepstatin, from Streptomyces species, Tox21_111747, HB3359, s7381, Pepstatin A, >=100,000 U/mg, AKOS024456453, Tox21_111747_1, AC-8820, CCG-207852, CS-4202, EBC-616912, FP29630, IDI1_002095, NCGC00160128-02, NCGC00161670-01, NCGC00161670-02, NCGC00161670-03, NCGC00161670-04, BS-16753, DA-76723, 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-, L-Alaninamide, N-(3-methyl-1-oxobutyl)-L-valyl-L-valyl-(3S,4S)-4-amino-3-hydroxy-6-methylheptanoyl-N-[(1S)-1-[(1S)-2-carboxy-1-hydroxyethyl]-3-methylbutyl]-, SMR001307268, SY067712, Pepstatin A, microbial, >=75% (HPLC), Pepstatin A, microbial, >=90% (HPLC), AB00513830, NS00051237, C74361, D03818, Pepstatin A  (Purity Higher than 90% by HPLC), SR-01000721876, Q7166509, SR-01000721876-3, BRD-K13571841-001-03-7, BRD-K13571841-001-14-4, (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-methyl-heptanoic acid, Isovaleryl-Val-Val-4-amino-3-hydroxy-6-methylheptanoyl-Ala-4-amino-3-hydroxy-6-methylheptanoic Acid, 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*)))))-, N-(3-Methylbutanoyl)-L-valyl-N-[(3S,4S)-1-{[(2S)-1-{[(2S,3S)-1-carboxy-2-hydroxy-5-methyl-3-hexanyl]amino}-1-oxo-2-propanyl]amino}-3-hydroxy-6-methyl-1-oxo-4-heptanyl]-L-valinamide
Theoretical properties:
molecular_formula: C34H63N5O9
molecular_weight: 685.9 g/mol
exact_mass: 685.46257860 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 8
hydrogen_bond_acceptor_count: 9
rotatable_bond_count: 22
heavy_atom_count: 48
topological_polar_surface_area: 223 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
{"pubchem": "Pepstatin A is a pentapeptide isolated from Streptomyces testaceus. It is a potent inhibitor of aspartyl proteases. It has a role as an EC 3.4.23.* (aspartic endopeptidase) inhibitor and a bacterial metabolite. It is a secondary carboxamide and a pentapeptide. It is a conjugate acid of a pepstatin A(1-).", "chebi": "A pentapeptide isolated from <em>Streptomyces testaceus</em>. It is a potent inhibitor of aspartyl proteases.", "chembl": "PEPSTATIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.", "wikipedia": "Pepstatin is a potent inhibitor of aspartyl proteases.  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).  It was originally isolated from cultures of various species of Actinomyces due to its ability to inhibit pepsin at picomolar concentrations. It was later found to inhibit nearly all acid proteases with high potency and, as such, has become a valuable research tool, as well as a common constituent of protease inhibitor cocktails.\nPepstatin A is well known to be an inhibitor of aspartic proteases such as pepsin, cathepsins D and E. Except for its role as a protease inhibitor, however, the pharmacological action of pepstatin A upon cells remain unclear. Pepstatin A suppresses receptor activator of NF-\u03baB ligand (RANKL)\u2013induced osteoclast differentiation. Pepstatin A suppresses the formation of multinuclear osteoclasts dose-dependently. This inhibition of the formation only affected osteoclast cells, i.e., not osteoblast-like cells. Furthermore, pepstatin A also suppresses differentiation from pre-osteoclast cells to mononuclear osteoclast cells dose-dependently. This inhibition seems to be independent of the activities of proteases such as cathepsin D, because the formation of osteoclasts was not suppressed with the concentration that inhibited the activity of cathepsin D. Cell signaling analysis indicated that the phosphorylation of ERK was inhibited in pepstatin A-treated cells, while the phosphorylation of I\u03baB and Akt showed almost no change. Furthermore, pepstatin A decreased the expression of nuclear factor of activated T cells c1 (NFATc1). These results suggest that pepstatin A suppresses the differentiation of osteoclasts through the blockade of ERK signaling and the inhibition of NFATc1 expression.\nPepstatin is practically insoluble in water, chloroform, ether, and benzene, however it can be dissolved in methanol, ethanol, and DMSO with acetic acid, to between 1 and 5 mg/ml."}