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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Physico-chemical Properties
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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
SMILES / InChI / InChIKey
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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
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
Search Google for chemical match using the InChIKey ZPBIJIIQXPRJSS-WNZSCWOMSA-O
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UniChem Compound Search for chemical match using the InChIKey ZPBIJIIQXPRJSS-WNZSCWOMSA-O
UniChem Connectivity Search for chemical match using the InChIKey ZPBIJIIQXPRJSS-WNZSCWOMSA-O