| Identification | Back Directory | [Name]
DEMETHYLASTERRIQUINONE B1 | [CAS]
78860-34-1 | [Synonyms]
DAQ B1
DMAQ-B1
L-783,281
Demethylasterriquino
DEMETHYLASTERRIQUINONE B1
Demethylasterriquinone B-1,Demethylasterriquinone B1
2-[2-(1,1-DIMETHYLALLYL)-1H-INDOL-3-YL]-3,6-DIHYDROXY-5-[7-(3-METHYLBUT-2-ENYL)-1H-INDOL-3-YL][1,4]BENZOQUINONE
2,5-DIHYDROXY-3-[7-(3-METHYL-BUT-2-ENYL)-1H-INDOL-3-YL]-6-[2-(1,1-DIMETHYL-ALLYL)-1H-INDOL-3-YL]-[1,4]BENZOQUINONE
2-(2-(1,1-Dimethyl-2-propenyl)-1H-indol-3-yl)-3,6-dihydroxy-5-(7-(3-methyl-2-butenyl)-1H-indol-3-yl)-2,5-cyclohexadiene-
2-[2-(1,1 Dimethyl-2-propenyl)-1H-indol-3-yl]-3,6-dihydroxy-5-[7-(3-methyl-2-butenyl)-1H-indol-3-yl]-2,5-cyclohexadien-1,4-dione
2-[2-(1,1-DIMETHYL-2-PROPENYL)-1H-INDOL-3-YL]-3,6-DIHYDROXY-5-[7-(3-METHYL-2-BUTENYL)-1H-INDOL-3-YL]-2,5-CYCLOHEXADIENE-1,4-DIONE
2,5-Cyclohexadiene-1,4-dione, 2-[2-(1,1-dimethyl-2-propen-1-yl)-1H-indol-3-yl]-3,6-dihydroxy-5-[7-(3-methyl-2-buten-1-yl)-1H-indol-3-yl]- | [Molecular Formula]
C32H30N2O4 | [MDL Number]
MFCD06410990 | [MOL File]
78860-34-1.mol | [Molecular Weight]
506.59 |
| Chemical Properties | Back Directory | [Boiling point ]
780.2±60.0 °C(Predicted) | [density ]
1.335±0.06 g/cm3(Predicted) | [storage temp. ]
Desiccate at -20°C | [solubility ]
Soluble to 100 mM in DMSO | [form ]
Powder | [pka]
2.82±0.50(Predicted) | [color ]
blue-black | [InChIKey]
XMGNJVXBPZAETK-UHFFFAOYSA-N |
| Hazard Information | Back Directory | [Description]
Demethylasterriquinone B1 (DMAQ B1) is a natural insulin mimic that activates insulin receptor tyrosine kinase (IRTK; EC50 = 6 μM). It less potently activates IGF1R and EGFR (EC50s = 100 μM for both). DMAQ B1 induces glucose uptake in adipocytes and skeletal muscle cells without activating proliferation. DMAQ B1 binds GAPDH in vitro. | [Uses]
Demethylasterriquinone B1 is a nonpeptidyl fungal metabolite that acted as an insulin mimetic in several biochemistry and cellular assays. | [Biological Activity]
Selective insulin receptor (IR) activator/mimetic (EC 50 values are 3-6 μ M for IRTK and 100 μ M for IGF1R and EGFR). Increases IR β subunit tyrosine phosphorylation and downstream activation of PI 3-kinase and Akt, but not ERK. Induces glucose uptake in adipocytes and skeletal muscle in vitro , without enhancing vascular proliferation. Binds GAPDH. | [storage]
Desiccate at -20°C | [References]
[1] G. SALITURO B Z F Pelaez. Discovery of a small molecule insulin receptor activator.[J]. Recent progress in hormone research, 2001, 25 1: 107-126. DOI: 10.1210/rp.56.1.107
[2] HENRY J TSAI Shan Y C. A novel hydroxyfuroic acid compound as an insulin receptor activator. Structure and activity relationship of a prenylindole moiety to insulin receptor activation.[J]. Journal of Biomedical Science, 2009: 68. DOI: 10.1186/1423-0127-16-68
[3] MICHAEL A. WEBER MDA. A novel insulin mimetic without a proliferative effect on vascular smooth muscle cells[J]. Journal of Vascular Surgery, 2000, 32 6: Pages 1118-1126. DOI: 10.1067/mva.2000.111280
[4] NICHOLAS J. G. WEBSTER PROF. Michael C P Prof Kaapjoo Park. Signaling Effects of Demethylasterriquinone B1, a Selective Insulin Receptor Modulator[J]. ChemBioChem, 2003, 4 5: 379-385. DOI: 10.1002/cbic.200200468
[5] HYUNSOO KIM. Glyceraldehyde 3-Phosphate Dehydrogenase Is a Cellular Target of the Insulin Mimic Demethylasterriquinone B1[J]. Journal of Medicinal Chemistry, 2007, 50 15: 3423-3426. DOI: 10.1021/jm070437i |
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