An inhibitor of the hedgehog signaling pathway
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Jervine

Item No. 11723

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2’R,3S,3’R,3’aS,6’S,6aS,6bS,7’aR,11aS,11bR)-2,3,3’a,4,4’,5’,6,6’,6a,6b,7,7’,7’a,8,11a,11b-hexadecahydro-3-hydroxy-3’,6’,10,11b-tetramethyl-spiro[9H-benzo[a]fluorene-9,2’(3’H)-furo[3,2-b]pyridin]-11(1H)-one
CAS Number
469-59-0
Synonyms
  • NSC 7520
  • NSC 23898
Molecular Formula
C27H39NO3
Formula Weight
425.6
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 2 mg/mlEthanol: 10 mg/mlEthanol:PBS (pH 7.2) (1:3): 0.25 mg/ml
λmax
251 nm
SMILES
CC1=C2[C@](CC[C@]13O[C@@](C[C@H](C)CN4)([H])[C@]4([H])[C@H]3C)([H])[C@]5([H])CC=C6C[C@@H](O)CC[C@]6(C)[C@@]5([H])C2=O
InChi Code
InChI=1S/C27H39NO3/c1-14-11-21-24(28-13-14)16(3)27(31-21)10-8-19-20-6-5-17-12-18(29)7-9-26(17,4)23(20)25(30)22(19)15(27)2/h5,14,16,18-21,23-24,28-29H,6-13H2,1-4H3/t14-,16+,18-,19-,20-,21+,23+,24-,26-,27-/m0/s1
InChi Key
CLEXYFLHGFJONT-DNMILWOZSA-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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    10 mg

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    50 mg

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    Cayman Chemical
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    Product Description

    Jervine is a naturally occurring teratogenic alkaloid that inhibits the sonic hedgehog pathway (IC50s = 500-700 nM) in vitro.1 It induces a variety of birth defects in vivo, including holoprosencephaly, cyclopia, cebocephaly, exencephaly, and microphthalmia in rat, chicken, and sheep.2,3,4 Jervine also reduces lipid accumulation and PPARγ and C/EBPα gene expression in 3T3-L1 adipocytes in vitro.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Williams, J.A., Guicherit, O.M., Zaharian, B.I., et al. Identification of a small molecule inhibitor of the hedgehog signaling pathway: Effects on basal cell carcinoma-like lesions. Proc. Natl. Acad. Sci. USA 100(8), 4616-4621 (2003).

    2. Sim, F.R.P., Matsumoto, N., Goulding, E.H., et al. Specific craniofacial defects induced by jervine in the cultured rat embryo. Teratog. Carcinoq. Mutagen. 3(2), 111-121 (1983).

    3. Cooper, M.K., Porter, J.A., Young, K.E., et al. Teratogen-mediated inhibition of target tissue response to Shh signaling. Science 280(5369), 1603-1607 (1998).

    4. Mistretta, C.M., Liu, H.-X., Gaffield, W., et al. Cyclopamine and jervine in embryonic rat tongue cultures demonstrate a role for Shh signaling in taste papilla development and patterning: Fungiform papillae double in number and form in novel locations in dorsal lingual epithelium. Deve. Biol. 254(1), 1-18 (2003).

    5. Park, J., Jeon, Y.D., Kim, H.L., et al. Veratri nigri rhizoma et radix (Veratrum nigrum L.) and its constituent jervine prevent adipogenesis via activation of the LKB1-AMPKα-ACC axis in vivo and in vitro. Evid. Based Complement. Altnernat. Med. 2016(8674397), 1-12 (2016).