mithramycin

Ligand id: 8394

Name: mithramycin

Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
Hydrogen bond acceptors 21
Hydrogen bond donors 11
Rotatable bonds 15
Topological polar surface area 358.2
Molecular weight 1084.47
XLogP -1.61
No. Lipinski's rules broken 3

Molecular properties generated using the CDK

Classification
Compound class Natural product or derivative
Approved drug? Yes (source: FDA (1970))
Withdrawn drug? Yes
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
International Nonproprietary Names
INN number INN
2029 plicamycin
Synonyms
aureolic acid
Mithracin®
mithramycin A
MMA
Database Links
CAS Registry No. 18378-89-7
ChEBI CHEBI:31856
DrugBank Ligand DB06810
PubChem CID 163659
Search Google for chemical match using the InChIKey CFCUWKMKBJTWLW-BKHRDMLASA-N
Search Google for chemicals with the same backbone CFCUWKMKBJTWLW
Search PubMed clinical trials plicamycin
Search PubMed titles plicamycin
Search PubMed titles/abstracts plicamycin
Wikipedia Plicamycin
Comments
We show one representation of mithramycin here. As a natural product there are alternate chemical structures due to the complex stereochemistry. Also known as plicamycin, the compound has been used clinically as an antineoplastic antibiotic (produced by Streptomyces plicatus).