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 (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Withdrawn drug?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
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).
Database Links
CAS Registry No. 18378-89-7
ChEBI CHEBI:31856
DrugBank Ligand DB06810
GtoPdb PubChem SID 252166605
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
Search UniChem for chemical match using the InChIKey CFCUWKMKBJTWLW-BKHRDMLASA-N
Search UniChem for chemicals with the same backbone CFCUWKMKBJTWLW
Wikipedia Plicamycin