mitomycin C   Click here for help

GtoPdb Ligand ID: 7089

Synonyms: Mitosol® | NSC-26980
Approved drug
mitomycin C is an approved drug (FDA (1981))
Compound class: Natural product
Comment: Mitomycin C is an antineoplastic drug, with DNA alkylating activity. It is one of the mitomycin family of compounds, isolated from Streptomyces caespitosus or Streptomyces lavendulae.
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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 9
Hydrogen bond donors 4
Rotatable bonds 4
Topological polar surface area 147.88
Molecular weight 334.13
XLogP -0.25
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES COC12C3NC3CN2C2=C(C1COC(=N)O)C(=O)C(=C(C2=O)C)N
Isomeric SMILES CO[C@@]12[C@H]3N[C@H]3CN2C2=C([C@H]1COC(=N)O)C(=O)C(=C(C2=O)C)N
InChI InChI=1S/C15H18N4O5/c1-5-9(16)12(21)8-6(4-24-14(17)22)15(23-2)13-7(18-13)3-19(15)10(8)11(5)20/h6-7,13,18H,3-4,16H2,1-2H3,(H2,17,22)/t6-,7+,13+,15-/m1/s1
InChI Key NWIBSHFKIJFRCO-WUDYKRTCSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Natural product
Approved drug? Yes (FDA (1981))
International Nonproprietary Names Click here for help
INN number INN
3043 mitomycin
Synonyms Click here for help
Mitosol® | NSC-26980
Database Links Click here for help
CAS Registry No. 1404-00-8 (source: Scifinder)
ChEBI CHEBI:27504
ChEMBL Ligand CHEMBL105
DrugBank Ligand DB00305
DrugCentral Ligand 1819
GtoPdb PubChem SID 178103667
PubChem CID 5746
Search Google for chemical match using the InChIKey NWIBSHFKIJFRCO-WUDYKRTCSA-N
Search Google for chemicals with the same backbone NWIBSHFKIJFRCO
Search PubMed clinical trials mitomycin
Search PubMed titles mitomycin
Search PubMed titles/abstracts mitomycin
UniChem Compound Search for chemical match using the InChIKey NWIBSHFKIJFRCO-WUDYKRTCSA-N
UniChem Connectivity Search for chemical match using the InChIKey NWIBSHFKIJFRCO-WUDYKRTCSA-N