roseophilin

Roseophilin is an antibiotic isolated from Streptomyces griseoviridis shown to have antitumor activity. The chemical structure can be considered in terms of two components, a macrotricyclic segment and a heterocyclic side-chain. Several laboratory syntheses of roseophilin (e.g., those of Trost, Fürstner, Salamone) are based upon the Paal-Knorr synthesis, and two others are based on the Nazarov cyclization reaction (those of Tius, Frontier). The compound is related to the prodiginines.

Chemical data

Formula: C27H33ClN2O2
Molecular weight: 453 g/mol
IUPAC name: (15Z)-15-[(5Z)-5-(3-chloropyrrol-2-ylidene)-3-methoxyfuran-2-ylidene]-13-propan-2-yl-2-azatricyclo[10.2.1.13,14]hexadeca-1(14),3(16)-diene
SMILES: CC(C)C1C\2CCCCCCCCC3=CC1=C(/C2=C\4/C(=C/C(=C/5\C(=CC=N5)Cl)/O4)OC)N3
InChIKey: XEQIXGXEBJYNMG-OLPWBVPVSA-N
XLogP: 6
Polar surface area: 46.6 Å²
H-bond donors: 1
H-bond acceptors: 3
Formal charge: 0

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Wikidata facts

Subclass of: chemical compound
Mass: 452.223055976

Show 3 more facts

isomeric SMILES: CC(C)C1C\2CCCCCCCCC3=CC1=C(/C2=C\4/C(=C/C(=C/5\C(=CC=N5)Cl)/O4)OC)N3
canonical SMILES: CC(C)C1C\2CCCCCCCCC3=CC1=C(/C2=C\4/C(=C/C(=C/5\C(=CC=N5)Cl)/O4)OC)N3
chemical formula: C₂₇H₃₃ClN₂O₂

via Wikidata · CC0

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