A fungal metabolite
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(–)-Cyclopenol

Item No. 27723

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2'S,3'R)-3'-(3-hydroxyphenyl)-4-methyl-spiro[3H-1,4-benzodiazepine-3,2'-oxirane]-2,5(1H,4H)-dione
CAS Number
20007-85-6
Synonyms
  • NSC 604990
Molecular Formula
C17H14N2O4
Formula Weight
310.3
Purity
≥95%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: solubleEthanol: solubleMethanol: soluble
SMILES
O=C1[C@@]2([C@@H](C3=CC=CC(O)=C3)O2)N(C)C(C(C=CC=C4)=C4N1)=O
InChi Code
InChI=1S/C17H14N2O4/c1-19-15(21)12-7-2-3-8-13(12)18-16(22)17(19)14(23-17)10-5-4-6-11(20)9-10/h2-9,14,20H,1H3,(H,18,22)/t14-,17+/m1/s1
InChi Key
BDDNYDPRCCDQQJ-PBHICJAKSA-N
Origin
Fungus/Penicillium sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $202

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    5 mg

    $797

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    Product Description

    (–)-Cyclopenol is a benzodiazepine alkaloid fungal metabolite originally isolated from P. viridicatum.1 It inhibits protein tyrosine phosphatase 1B (PTP1B; IC50 = 30 μM).2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Mohammed, Y.S., and Luckner, M. The structure of cyclopenin and cyclopenol, metabolic products from penicillium cyclopium westling and penicillium viridicatum westling. Tetrahedron Lett. 4(28), 1953-1958 (1963).

    2. Sohn, J.H., Lee, Y.-R., Lee, D.-S., et al. PTP1B inhibitory secondary metabolites from marine-derived fungal strains Penicillium spp. and Eurotium sp. J. Microbiol. Biotechnol. 23(9), 1206-1211 (2013).