Tyropeptin A-4
Basic information
- CAS
688737-89-5- Standard SMILES
CC(C)[C@H](NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)CC1CCCCC1)C(=O)NC(C=O)Cc1ccc(O)cc1- InChIKey
PBHZSZHBJWAKIL-TXJYOHDVSA-N- Molecular formula
- C31H41N3O6
- Average molar mass
- 551.7 g/mol
- Monoisotopic mass
- 551.29953604
Names & identifiers
- Preferred name
- Tyropeptin A-4
- IUPAC
- (2S)-2-[[(2S)-2-[(2-cyclohexylacetyl)amino]-3-(4-hydroxyphenyl)propanoyl]amino]-N-[1-(4-hydroxyphenyl)-3-oxopropan-2-yl]-3-methylbutanamide
- English name
- TP101
- Molecular formula
- C31H41N3O6
- Molecular weight
- 551.67
Names & synonyms
Tyropeptin A-4TP-101688737-89-5UNII-XYS3918ESEXYS3918ESECHEMBL361383L-Valinamide, N-(cyclohexylacetyl)-L-tyrosyl-N-(1-formyl-2-(4-hydroxyphenyl)ethyl)-(2S)-2-[[(2S)-2-[(2-cyclohexylacetyl)amino]-3-(4-hydroxyphenyl)propanoyl]amino]-N-[1-(4-hydroxyphenyl)-3-oxopropan-2-yl]-3-methylbutanamideorb1701500SCHEMBL29393951BDBM50475037AKOS040747557
Show more names
Tyropeptin A4Tyropeptin A 4Tyropeptin A 4,Tyropeptin A4
CS-0107933T26301Q27294064
Database identifiers
- CAS
688737-89-5- PubChem CID
- 44390959
- ChEMBL
CHEMBL361383- UNII
- XYS3918ESE
Properties
Computed structural properties
- XLogP
- 5.1
- Topological polar surface area
- 145 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 13
- Heavy atoms
- 40
- Formal charge
- 0
- Complexity
- 814
Physicochemical properties
- Melting point
- 153 · 153-155 °C
- Boiling point
- 887.82 · 887.820±65.00 °C(Press: 760.00 Torr)(predicted)
- Density
- 1.198 · 1.198±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
- pka
- 9.828 · 9.828±0.15(predicted)
- FDA UNII
- 3918 ESE · XYS3918ESE
Chemistry & industry
Applications
UsesTyropeptin A-4 (TP-101) is a potent proteasome inhibitor with the ability to inhibit mammalian 20S proteasome activity. Tyropeptin A-4 exerts its inhibitory effect by binding to the site responsible for trypsin-like activity. Tyropeptin A-4 derivative TP-104 has a 20-fold increase in inhibitory activity over Tyropeptin A. TP-110 specifically inhibits trypsin-like activity without affecting PGPH and trypsin-like activity[1].
Related reactions
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Compound notes
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