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
References
1. BROWN JH, KENNEDY BJ. (1965)
MITHRAMYCIN IN THE TREATMENT OF DISSEMINATED TESTICULAR NEOPLASMS.
N Engl J Med, 272: 111-8. [PMID:14224214]
2. Jones Jr DE, Cui DM, Miller DM. (1995)
Expression of beta-galactosidase under the control of the human c-myc promoter in transgenic mice is inhibited by mithramycin.
Oncogene, 10 (12): 2323-30. [PMID:7784080]
3. Lin RK, Hsu CH, Wang YC. (2007)
Mithramycin A inhibits DNA methyltransferase and metastasis potential of lung cancer cells.
Anticancer Drugs, 18 (10): 1157-64. [PMID:17893516]
4. Rodriguez-Paredes M, Martinez de Paz A, Simó-Riudalbas L, Sayols S, Moutinho C, Moran S, Villanueva A, Vázquez-Cedeira M, Lazo PA, Carneiro F et al.. (2014)
Gene amplification of the histone methyltransferase SETDB1 contributes to human lung tumorigenesis.
Oncogene, 33 (21): 2807-13. [PMID:23770855]
5. Ryu H, Lee J, Hagerty SW, Soh BY, McAlpin SE, Cormier KA, Smith KM, Ferrante RJ. (2006)
ESET/SETDB1 gene expression and histone H3 (K9) trimethylation in Huntington's disease.
Proc Natl Acad Sci USA, 103 (50): 19176-81. [PMID:17142323]