Antipain
Basic information
- CAS
37691-11-5- Standard SMILES
CC(C)[C@H](NC(=O)[C@H](CCCN=C(N)N)NC(=O)N[C@@H](Cc1ccccc1)C(=O)O)C(=O)N[C@H](C=O)CCCN=C(N)N- InChIKey
SDNYTAYICBFYFH-TUFLPTIASA-N- Molecular formula
- C27H44N10O6
- Average molar mass
- 604.7 g/mol
- Monoisotopic mass
- 604.34452916
Overview
Antipain is a serine/cysteine protease inhibitor originally isolated from various strains of actinomycetes. Early studies investigated the potential for antipain to alter DNA damage and chromosomal aberrations in irradiated cells or those treated with chemical mutagens such as N-methyl-N'-nitro-N-nitrosoguanidine (MNNG). Antipain was used in 2010 to obtain a crystal structure of the Leishmania major oligopeptidase B (OPB), a serine protease that serves as a virulence factor in trypanosomatids. The binding of antipain to OPB has been used in molecular dynamic studies to identify other OPB inhibitors with more favourable pharmacodynamic and pharmacokinetic properties for potential development as anti-trypanosomatid drugs.
Names & identifiers
- Preferred name
- Antipain
- IUPAC
- (2S)-2-[[(2S)-5-(diaminomethylideneamino)-1-[[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxopentan-2-yl]carbamoylamino]-3-phenylpropanoic acid
- English name
- Antipain hydrochloride dihydrate
- Molecular formula
- C27H44N10O6
- Molecular weight
- 604.7
Names & synonyms
Antipain37691-11-5DTXSID4095873347V479BE6LL-Valinamide, N2-(((1-carboxy-2-phenylethyl)amino)carbonyl)-L-arginyl-N-(4-((aminoiminomethyl)amino)-1-formylbutyl)-(2S)-2-[[(2S)-5-(diaminomethylideneamino)-1-[[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxopentan-2-yl]carbamoylamino]-3-phenylpropanoic acidL-Valinamide, N2-[[(1-carboxy-2-phenylethyl)amino]carbonyl]-L-arginyl-N-[4-[(aminoiminomethyl)amino]-1-formylbutyl]-(2S)-2-(((2S)-5-(diaminomethylideneamino)-1-(((2S)-1-(((2S)-5-(diaminomethylideneamino)-1-oxopentan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)amino)-1-oxopentan-2-yl)carbamoylamino)-3-phenylpropanoic acidRefChem:113237DTXCID301386630(2S)-2-((((1S)-4-carbamimidamido-1-(((1S)-1-(((2S)-5-carbamimidamido-1-oxopentan-2-yl)carbamoyl)-2-methylpropyl)carbamoyl)butyl)carbamoyl)amino)-3-phenylpropanoic acid253-631-0
Show more names
Aids006469Aids-006469PHE-ARG-VAL-ARG-CHO
Properties
Computed structural properties
- XLogP
- -2.7
- Topological polar surface area
- 283 Ų
- Hydrogen bond donors
- 9
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 19
- Heavy atoms
- 43
- Formal charge
- 0
- Complexity
- 975
Physicochemical properties
- Density
- 1.38 · 1.38
- storage temp.
- 20 °C · −20°C
- pka
- 3.84 · 3.84±0.10(Predicted)
- Specific Activity
- 50000 U/mg · >50000U/mg
- BRN
- 6837629 · 6837629
- InChIKey
- SDNYTAYICBFYFH-KTYMLHDXSA-N
- SMILES
- [H]C(=O)C(CCCNC(N)=N)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=N)NC(=O)N[C@@H](Cc1ccccc1)C(O)=O)C(C)C
- FDA UNII
- 47 V479BE6L · 47V479BE6L
- UNSPSC Code
- 12352202 · 12352202
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302
- Precautionary statements
- 264 · P264-P270-P301+P312-P330-P501
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- WGK Germany
- 3 · 3
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- F
- 1-10
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- rtecs
- YV9350700
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- Precautionary statements
- P264-P270-P301+P312-P330-P501
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationCompounds which inhibit or antagonize biosynthesis or actions of proteases (ENDOPEPTIDASES).
Applications
UsesAntipain is a reversible inhibitor of Ser and Cys proteases.
General DescriptionChemical structure: peptide
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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