DMAMCL   Click here for help

GtoPdb Ligand ID: 9936

Synonyms: compound 21 [PMID: 22985027] | dimethylaminomicheliolide
Compound class: Synthetic organic
Comment: DMAMCL (dimethylaminomicheliolide) is a Michael adduct of micheliolide (a natural plant-derived guaianolide sesquiterpene lactone; PubChem CID 442279) [2]. It was originally identified for its ability to inhibit acute myelogenous leukemia (AML) stem and progenitor cells. More recently its mechanism of action has been determined [1]. It induces irreversible tetramerization of PKM2 and acts as a functional activator of PKM2 pyruvate kinase activity. This mechanism is being exploited as a potential anti-cancer therapeutic, with an orally active DMAMCL prodrug (ACT001) in early clinical trial (in Australian trial ACTRN12616000228482) in patients with advanced solid tumours, including glioblastoma multiforme (GBM).
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 3
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 50.97
Molecular weight 294.21
XLogP 0.69
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 C[NH+](CC1C(=O)OC2C1CCC(=C1C2C(C)(O)CC1)C)C
Isomeric SMILES C[NH+](C[C@@H]1C(=O)O[C@H]2[C@H]1CCC(=C1[C@@H]2[C@](C)(O)CC1)C)C
InChI InChI=1S/C17H27NO3/c1-10-5-6-12-13(9-18(3)4)16(19)21-15(12)14-11(10)7-8-17(14,2)20/h12-15,20H,5-9H2,1-4H3/p+1/t12-,13-,14-,15-,17+/m0/s1
InChI Key ZPBIJIIQXPRJSS-WNZSCWOMSA-O

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 Synthetic organic
IUPAC Name Click here for help
{[(3R,3aS,9R,9aS,9bS)-9-hydroxy-6,9-dimethyl-2-oxo-2H,3H,3aH,4H,5H,7H,8H,9H,9aH,9bH-azuleno[4,5-b]furan-3-yl]methyl}dimethylazanium
Synonyms Click here for help
compound 21 [PMID: 22985027] | dimethylaminomicheliolide
Database Links Click here for help
GtoPdb PubChem SID 363894230
PubChem CID 133081974
Search Google for chemical match using the InChIKey ZPBIJIIQXPRJSS-WNZSCWOMSA-O
Search Google for chemicals with the same backbone ZPBIJIIQXPRJSS
UniChem Compound Search for chemical match using the InChIKey ZPBIJIIQXPRJSS-WNZSCWOMSA-O
UniChem Connectivity Search for chemical match using the InChIKey ZPBIJIIQXPRJSS-WNZSCWOMSA-O