Plicamycin

A tricyclic pentaglycosidic antibiotic from Streptomyces strains that inhibits RNA and protein synthesis by adhering to DNA. It is used as a fluorescent dye and as an antineoplastic agent, especially in bone and testicular tumors. Plicamycin is also used to reduce hypercalcemia, especially that due to malignancies.

Molecular Formula

C₅₂H₇₆O₂₄

Molecular Weight

1085.1 g/mol

CAS Registry No.

18378-89-7

IUPAC Name

(2S,3S)-2-[(2S,4R,5R,6R)-4-[(2S,4R,5S,6R)-4-[(2S,4S,5R,6R)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]oxy-3-[(1S,3S,4R)-3,4-dihydroxy-1-methoxy-2-oxopentyl]-6-[(2S,4R,5R,6R)-4-[(2S,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]oxy-8,9-dihydroxy-7-methyl-3,4-dihydro-2H-anthracen-1-one

InChIKey

CFCUWKMKBJTWLW-BKHRDMLASA-N

SMILES

C[C@@H]1[C@H]([C@@H](C[C@@H](O1)O[C@@H]2C[C@@H](O[C@@H]([C@H]2O)C)OC3=CC4=CC5=C(C(=O)[C@H]([C@@H](C5)[C@@H](C(=O)[C@H]([C@@H](C)O)O)OC)O[C@H]6C[C@H]([C@@H]([C@H](O6)C)O)O[C@H]7C[C@H]([C@H]([C@H](O7)C)O)O[C@H]8C[C@]([C@@H]([C@H](O8)C)O)(C)O)C(=C4C(=C3C)O)O)O)O

MeSH Unique ID

D008926

Source

PubChem CID 163659

• Antineoplastic Antibiotics
• Calcium-Regulating Hormones and Agents
• Fluorescent Dyes
• Nucleic Acid Synthesis Inhibitors
• Protein Synthesis Inhibitors

93; was MITHRAMYCIN 1971-92 (Prov 1971-72)

• Antibiotics, Antineoplastic (1967-1970)

1. D02w.455w.426w.559w.847w.562.050.650w
2. D04w.615w.562.050.650w
3. D09w.408w.051.059.650w

QV 269

1. National Library of Medicine. Plicamycin. Medical Subject Headings (MeSH). 2026. Unique ID D008926. http://id.nlm.nih.gov/mesh/2026/D008926
2. Plicamycin. In: Wikipedia. https://en.wikipedia.org/wiki/Plicamycin
3. Plicamycin. In: Wikidata. https://www.wikidata.org/wiki/Q3906700
4. Plicamycin. In: PubChem Compound. CID 163659. https://pubchem.ncbi.nlm.nih.gov/compound/163659