A natural insulin mimic
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Demethylasterriquinone B1

Item No. 21026

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
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]-2,5-cyclohexadiene-1,4-dione
CAS Number
78860-34-1
Synonyms
  • DMAQ B1
  • L-783,281
Molecular Formula
C32H30N2O4
Formula Weight
506.6
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 15 mg/mlDMF:PBS (pH 7.2) (1:4): 0.20 mg/mlDMSO: 10 mg/mlEthanol: 10 mg/ml
λmax
222, 282, 289 nm
SMILES
OC(C(C(C1=CNC2=C1C=CC=C2C/C=C(C)\C)=C3O)=O)=C(C4=C(C(C)(C)C=C)NC5=C4C=CC=C5)C3=O
InChi Code
InChI=1S/C32H30N2O4/c1-6-32(4,5)31-23(20-11-7-8-13-22(20)34-31)25-29(37)27(35)24(28(36)30(25)38)21-16-33-26-18(15-14-17(2)3)10-9-12-19(21)26/h6-14,16,33-35,38H,1,15H2,2-5H3
InChi Key
XMGNJVXBPZAETK-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Cayman Chemical
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    Product Description

    Demethylasterriquinone B1 (DMAQ B1) is a natural insulin mimic that activates insulin receptor tyrosine kinase (IRTK; EC50 = 6 µM).1,2,3,4 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.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Salituro, G.M., Pelaez, F., and Zhang, B.B. Discovery of a small molecule insulin receptor activator. Recent Prog. Horm. Res. 56, 107-126 (2001).

    2. Tsai, H.J., and Chou, S.Y. A novel hydroxyfuroic acid compound as an insulin receptor activator. Structure and activity relationship of a prenylindole moiety to insulin receptor activation. J. Biomed. Sci. 16(68), (2009).

    3. Weber, M.A., Lidor, A., Arora, S., et al. A novel insulin mimetic without a proliferative effect on vascular smooth muscle cells. J. Vasc. Surg. 32(6), 1118-1126 (2000).

    4. Webster, N.J.G., Park, K., and Pirrung, M.C. Signaling effects of demethylasterriquinone B1, a selective insulin receptor modulator. Chembiochem 4(5), 379-385 (2003).

    5. Kim, H., Deng, L., Xiong, X., et al. Glyceraldehyde 3-phosphate dehydrogenase is a cellular target of the insulin mimic demethylasterriquinone B1. J. Med. Chem. 50(15), 3423-3426 (2007).