methyl N-[(Z,7R)-8-[4-[(2Z)-hexa-2,5-dienyl]-1,3-thiazol-2-yl]-7-hydroxy-8-methyl-3-methylidenenon-4-enyl]carbamate
Basic information
- CAS
114582-75-1- Standard SMILES
C=CC/C=C\Cc1csc(C(C)(C)[C@H](O)C/C=C\C(=C)CCNC(=O)OC)n1- InChIKey
WOVFSYAJXQSJES-OEKGKEFLSA-N- Molecular formula
- C22H32N2O3S
- Average molar mass
- 404.6 g/mol
- Monoisotopic mass
- 404.21336406
Names & identifiers
- Preferred name
- methyl N-[(Z,7R)-8-[4-[(2Z)-hexa-2,5-dienyl]-1,3-thiazol-2-yl]-7-hydroxy-8-methyl-3-methylidenenon-4-enyl]carbamate
- IUPAC
- methyl N-[(Z,7R)-8-[4-[(2Z)-hexa-2,5-dienyl]-1,3-thiazol-2-yl]-7-hydroxy-8-methyl-3-methylidenenon-4-enyl]carbamate
- English name
- mycothiazole
- Molecular formula
- C22H32N2O3S
- Molecular weight
- 404.57
Names & synonyms
CHEMBL490508mycothiazole
Database identifiers
- CAS
114582-75-1- PubChem CID
- 11632806
- ChEMBL
CHEMBL490508- Nikkaji
- J1.011.165J
Properties
Computed structural properties
- XLogP
- 5.5
- Topological polar surface area
- 99.7 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 13
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 572
Chemistry & industry
Applications
DescriptionMycothiazole is from cacospongia mycofijiensis.
UsesMycothiazole is an inhibitor for mitochondrial electron transport chain (ETC) complex I. Mycothiazole exhibits cytotoxicity in cancer cells Huh7 (IC50 is 55.8 μM), U87 and MCF7. Mycothiazole induces apoptosis in Huh7. Mycothiazole utilizes the unfolded protein response (UPR) and heat shock response (HSR) pathway involved transcription factors ATFS-1 and HSF1, to extend the lifespan of C. elegans[1].
Additional notes
DefinitionChEBI: Mycothiazole is a member of thiazoles. It has a role as a metabolite.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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