mithramycin   Click here for help

GtoPdb Ligand ID: 8394

Synonyms: aureolic acid | Mithracin® | mithramycin A | MMA
Approved drug PDB Ligand
mithramycin is an approved drug (FDA (1970))
Compound class: Natural product or derivative
Comment: 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 antibacterial (produced by Streptomyces plicatus).
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 21
Hydrogen bond donors 11
Rotatable bonds 15
Topological polar surface area 358.2
Molecular weight 1084.47
XLogP -0.39
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES COC(C1Cc2cc3cc(OC4OC(C)C(C(C4)OC4CC(O)C(C(O4)C)O)O)c(c(c3c(c2C(=O)C1OC1OC(C)C(C(C1)OC1OC(C)C(C(C1)OC1OC(C)C(C(C1)(C)O)O)O)O)O)O)C)C(=O)C(C(O)C)O
Isomeric SMILES CO[C@@H]([C@@H]1Cc2cc3cc(O[C@@H]4O[C@H](C)[C@H]([C@@H](C4)O[C@H]4C[C@@H](O)[C@@H]([C@H](O4)C)O)O)c(c(c3c(c2C(=O)[C@H]1O[C@@H]1O[C@H](C)[C@H]([C@@H](C1)O[C@@H]1O[C@H](C)[C@@H]([C@@H](C1)O[C@@H]1O[C@H](C)[C@H]([C@@](C1)(C)O)O)O)O)O)O)C)C(=O)[C@H]([C@H](O)C)O
InChI InChI=1S/C52H76O24/c1-18-29(72-34-14-30(43(58)21(4)68-34)73-33-13-28(54)42(57)20(3)67-33)12-26-10-25-11-27(49(66-9)48(63)41(56)19(2)53)50(47(62)39(25)46(61)38(26)40(18)55)76-36-16-31(44(59)23(6)70-36)74-35-15-32(45(60)22(5)69-35)75-37-17-52(8,65)51(64)24(7)71-37/h10,12,19-24,27-28,30-37,41-45,49-51,53-61,64-65H,11,13-17H2,1-9H3/t19-,20-,21-,22-,23-,24-,27+,28-,30-,31-,32-,33+,34+,35+,36+,37+,41+,42-,43-,44-,45+,49+,50+,51-,52+/m1/s1
InChI Key CFCUWKMKBJTWLW-BKHRDMLASA-N
Classification Click here for help
Compound class Natural product or derivative
Approved drug? Yes (FDA (1970))
Withdrawn drug? Yes
IUPAC Name Click here for help
(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 Click here for help
INN number INN
2029 plicamycin
Synonyms Click here for help
aureolic acid | Mithracin® | mithramycin A | MMA
Database Links Click here for help
CAS Registry No. 18378-89-7
ChEBI CHEBI:31856
DrugBank Ligand DB06810
DrugCentral Ligand 2223
GtoPdb PubChem SID 252166605
PubChem CID 163659
RCSB PDB Ligand QWP
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
UniChem Compound Search for chemical match using the InChIKey CFCUWKMKBJTWLW-BKHRDMLASA-N
UniChem Connectivity Search for chemical match using the InChIKey CFCUWKMKBJTWLW-BKHRDMLASA-N
Wikipedia Plicamycin