Structure via PubChem · Public domain (PubChem)
Hitachimycin
Sign in to saveHitachimycin, also known as stubomycin, is a cyclic polypeptide produced by Streptomyces that acts as an antibiotic. It exhibits cytotoxic activity against mammalian cells, Gram-positive bacteria, yeast, and fungi, as well as hemolytic activity; this is mediated by changes at the cell membrane and subsequent lysis. Owing to its cytotoxic activity against mammalian cells and tumors, it was first proposed as an antitumor antibiotic.
Chemical data
- Formula
- C29H35NO5
- Molecular weight
- 477.6 g/mol
- IUPAC name
- (2Z,4E,6E,12E)-16,20-dihydroxy-21-methoxy-3-methyl-10-phenyl-9-azabicyclo[17.3.0]docosa-2,4,6,12,19-pentaene-8,18-dione
- SMILES
- C/C/1=C/C2CC(C(=C2C(=O)CC(CC/C=C/CC(NC(=O)/C=C\C=C1)C3=CC=CC=C3)O)O)OC
- InChIKey
- PLQKHNPZPRTISL-ITRAFUHISA-N
- XLogP
- 4
- Polar surface area
- 95.9 Ų
- H-bond donors
- 3
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 477.25152322
Show 4 more facts
- isomeric SMILES
- COC1CC2/C=C(C)\C=C\C=C\C(=O)NC(c3ccccc3)C/C=C/CCC(O)CC(=O)C2=C1O
- chemical formula
- C₂₉H₃₅NO₅
- canonical SMILES
- CC1=CC2CC(C(=C2C(=O)CC(CCC=CCC(NC(=O)C=CC=C1)C3=CC=CC=C3)O)O)OC
- found in taxon
- Streptomyces
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
Hitachimycin, also known as stubomycin, is a cyclic polypeptide produced by Streptomyces that acts as an antibiotic. It exhibits cytotoxic activity against mammalian cells, Gram-positive bacteria, yeast, and fungi, as well as hemolytic activity; this is mediated by changes at the cell membrane and subsequent lysis. Owing to its cytotoxic activity against mammalian cells and tumors, it was first proposed as an antitumor antibiotic.
As of 2007, it has not been used in a clinical setting.
Excerpted from Wikipedia’s “Hitachimycin” article, available under the CC BY-SA 4.0 licence.