Structure via PubChem · Public domain (PubChem)
تائوتومیسین
Sign in to saveTautomycin is a chemical that occurs naturally in shellfish and is produced by the bacterium Streptomyces spiroverticillatus. It is a polyketide-based structure characterized by a three hydroxyl groups, two ketones, a dialkylmaleic anhydride, an ester linkage (connecting anhydride unit to polyketide chain), a spiroketal and one methyl ether among others.
Chemical data
- Formula
- C41H66O13
- Molecular weight
- 767 g/mol
- IUPAC name
- [(3R,4R,5R,8S,9S,12R)-12-[(2S,3S,6R,8S,9R)-3,9-dimethyl-8-[(3S)-3-methyl-4-oxopentyl]-1,7-dioxaspiro[5.5]undecan-2-yl]-5,9-dihydroxy-4-methoxy-2,8-dimethyl-7-oxotridecan-3-yl] (3R)-3-hydroxy-3-(4-methyl-2,5-dioxofuran-3-yl)propanoate
- SMILES
- C[C@@H]1CC[C@@]2(CC[C@@H]([C@@H](O2)[C@H](C)CC[C@@H]([C@H](C)C(=O)C[C@H]([C@H]([C@@H](C(C)C)OC(=O)C[C@H](C3=C(C(=O)OC3=O)C)O)OC)O)O)C)O[C@H]1CC[C@H](C)C(=O)C
- InChIKey
- RFCWHQNNCOJYTR-IRCAEPKSSA-N
- XLogP
- 4.9
- Polar surface area
- 192 Ų
- H-bond donors
- 3
- H-bond acceptors
- 13
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
205 papers- Tautomycin's interactions with protein phosphatase 1.Chemistry, an Asian journal · 2010
- Tautomycin and enzalutamide combination yields synergistic effects on castration-resistant prostate cancer.Cell death discovery · 2022
- A new antibiotic, tautomycin.The Journal of antibiotics · 1987
- Synthesis of specific protein phosphatase inhibitors, tautomycin and tautomycetin toward structure-activity relationship study.Current medicinal chemistry · 2002
- Natural products with maleic anhydride structure: nonadrides, tautomycin, chaetomellic anhydride, and other compounds.Chemical reviews · 2007
via PubMed
Wikidata facts
- Mass
- 766.450342
Show 4 more facts
- chemical formula
- C₄₁H₆₆O₁₃
- canonical SMILES
- CC1CCC2(CCC(C(O2)C(C)CCC(C(C)C(=O)CC(C(C(C(C)C)OC(=O)CC(C3=C(C(=O)OC3=O)C)O)OC)O)O)C)OC1CCC(C)C(=O)C
- isomeric SMILES
- C[C@@H]1CC[C@@]2(CC[C@@H]([C@@H](O2)[C@H](C)CC[C@@H]([C@H](C)C(=O)C[C@H]([C@H]([C@@H](C(C)C)OC(=O)C[C@H](C3=C(C(=O)OC3=O)C)O)OC)O)O)C)O[C@H]1CC[C@H](C)C(=O)C
- subject has role
- platelet aggregation inhibitors
Sources (2)
via Wikidata · CC0