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.

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Vinony's link graph records 2 inbound references to roseophilin, and connects out to antibiotic, digital object identifier and chemical formula.

It is catalogued under topics including Antibiotics, Chembox image size set and Chloroarenes.

Vinony links it to 7 Wikipedia language editions.

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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