Structure via PubChem · Public domain (PubChem)
Talopeptin
Sign in to saveTalopeptin is a chemical compound derived from cultures of Streptomyces. It is a known reversible inhibitor of thermolysin and is expected to inhibit other metalloproteinases. Chemically, talopeptin differs from its closely related peptidase inhibitor phosphoramidon by a single stereocenter.
Chemical data
- Formula
- C23H34N3O10P
- Molecular weight
- 543.5 g/mol
- IUPAC name
- (2S)-2-[[(2S)-2-[[hydroxy-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyphosphoryl]amino]-4-methylpentanoyl]amino]-3-(1H-indol-3-yl)propanoic acid
- SMILES
- C[C@H]1[C@H]([C@H]([C@H]([C@@H](O1)OP(=O)(N[C@@H](CC(C)C)C(=O)N[C@@H](CC2=CNC3=CC=CC=C32)C(=O)O)O)O)O)O
- InChIKey
- ZPHBZEQOLSRPAK-XVOJFHBISA-N
- XLogP
- -0.2
- Polar surface area
- 211 Ų
- H-bond donors
- 8
- H-bond acceptors
- 11
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- phosphoramidon
- Mass
- 543.198181
Show 3 more facts
- chemical formula
- C₂₃H₃₄N₃O₁₀P
- isomeric SMILES
- C[C@H]1[C@H]([C@H]([C@H]([C@@H](O1)OP(=O)(N[C@@H](CC(C)C)C(=O)N[C@@H](CC2=CNC3=CC=CC=C32)C(=O)O)O)O)O)O
- canonical SMILES
- CC1C(C(C(C(O1)OP(=O)(NC(CC(C)C)C(=O)NC(CC2=CNC3=CC=CC=C32)C(=O)O)O)O)O)O
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- References
- External links
{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 443607228 | ImageFile = talopeptin.png | ImageSize = 200px | SystematicName = (2S)-2-{(2S)-2-[(Hydroxy{[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phosphoryl)amino]-4-methylpentanamido}-3-(1H-indol-3-yl)propanoic acid | OtherNames = N-(N-{[(6-Deoxy-α-L-talopyranosyl)oxy]hydroxyphosphinyl}-L-leucyl)-L-tryptophan |Section1= |Section2= |Section3= }}
Talopeptin is a chemical compound derived from cultures of Streptomyces. It is a known reversible inhibitor of thermolysin and is expected to inhibit other metalloproteinases. Chemically, talopeptin differs from its closely related peptidase inhibitor phosphoramidon by a single stereocenter.
Excerpted from Wikipedia’s “Talopeptin” article, available under the CC BY-SA 4.0 licence.