nogalamycin

Nogalamycin is an anthracycline antibiotic produced by the soil bacteria Streptomyces nogalater. It has antitumor properties but it is also highly cardiotoxic. The less cardiotoxic semisynthetic analog menogaril was developed in the 1970s. Currently nogalamycin and menogaril are not used clinically.

Chemical data

Formula: C39H49NO16
Molecular weight: 787.8 g/mol
IUPAC name: methyl (1R,10S,12S,13R,21R,22S,23R,24R)-23-(dimethylamino)-4,8,12,22,24-pentahydroxy-1,12-dimethyl-6,17-dioxo-10-[(2R,3R,4R,5S,6S)-3,4,5-trimethoxy-4,6-dimethyloxan-2-yl]oxy-20,25-dioxahexacyclo[19.3.1.02,19.05,18.07,16.09,14]pentacosa-2,4,7(16),8,14,18-hexaene-13-carboxylate
SMILES: C[C@H]1[C@@H]([C@@]([C@H]([C@@H](O1)O[C@H]2C[C@]([C@@H](C3=CC4=C(C(=C23)O)C(=O)C5=C(C=C6C(=C5C4=O)O[C@H]7[C@H]([C@@H]([C@H]([C@@]6(O7)C)O)N(C)C)O)O)C(=O)OC)(C)O)OC)(C)OC)OC
InChIKey: KGTDRFCXGRULNK-JYOBTZKQSA-N
XLogP: 1.1
Polar surface area: 229 Å²
H-bond donors: 5
H-bond acceptors: 17
Formal charge: 0

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Drug data · ChEMBL

Max clinical phase: Phase 2
Molecule type: Small molecule

via ChEMBL · EBI

Research

344 papers

The snogI Gene is Necessary for the Proper Functioning of the Nogalamycin Biosynthesis Pathway.Indian journal of microbiology · 2021
DNA-nogalamycin interactions.Biochemistry · 1991
The biochemical pharmacology of nogalamycin and its derivatives.Pharmacology & therapeutics · 1991
Progress toward the Total Synthesis of Nogalamycin Using a Benzyne Cycloaddition Strategy.The Journal of organic chemistry · 2024
The Rieske Oxygenase SnoT Catalyzes 2''-Hydroxylation of l-Rhodosamine in Nogalamycin Biosynthesis.Chembiochem : a European journal of chemical biology · 2020

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Wikidata facts

Subclass of: chemical compound
Mass: 787.305

Show 5 more facts

chemical formula: C₃₉H₄₉NO₁₆
canonical SMILES: CC1C(C(C(C(O1)OC2CC(C(C3=C2C(=C4C(=C3)C(=O)C5=C6C(=CC(=C5C4=O)O)C7(C(C(C(C(O6)O7)O)N(C)C)O)C)O)C(=O)OC)(C)O)OC)(C)OC)OC
isomeric SMILES: C[C@H]1[C@@H]([C@@]([C@H]([C@@H](O1)O[C@H]2C[C@]([C@@H](C3=C2C(=C4C(=C3)C(=O)C5=C6C(=CC(=C5C4=O)O)[C@@]7([C@@H]([C@H]([C@@H]([C@H](O6)O7)O)N(C)C)O)C)O)C(=O)OC)(C)O)OC)(C)OC)OC
subject has role: DNA polymerase inhibitors
Commons category: Nogalamycin

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