MW 411.6 Da, Purity >99%. Cell-permeable inhibitor of hedgehog (Hh) signaling, via direct inhibition of Smo (Smoothened), the accessory protein to the putative Hh receptor. Anticancer and teratogenic activity in vivo.
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Key facts
- CAS number
- 4449-51-8
- Purity
- > 99%
- Form
- Liquid
- Molecular weight
- 411.6 Da
- Molecular formula
- C27H41NO2
- PubChem identifier
- 442972
- Nature
- Synthetic
Target data
Alternative names
FZD11, Frizzled family member 11, GX, Gx protein, HHG-1, HLP 3, HPE 3, Holoprosencephaly 3, MCOPCB5, Protein Gx, SHH_HUMAN, SMMC I, SMOH, SMO_HUMAN, Smoothened frizzled family receptor, Smoothened homolog, Smoothened homolog (Drosophila), Smoothened homolog precursor (SMO) (Gx protein), Smoothened seven transmembrane spanning receptor, Sonic Hedgehog (Drosophila) homolog, Sonic hedgehog homolog, Sonic hedgehog protein, Sonic hedgehog protein C-product, TPT, TPTPS, sonic hedgehog homolog (Drosophila)
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MW 411.6 Da, Purity >99%. Cell-permeable inhibitor of hedgehog (Hh) signaling, via direct inhibition of Smo (Smoothened), the accessory protein to the putative Hh receptor. Anticancer and teratogenic activity in vivo.
Key facts
- CAS number
- 4449-51-8
- Purity
- > 99%
- Form
- Liquid
- Molecular weight
- 411.6 Da
- Molecular formula
- C27H41NO2
- PubChem identifier
- 442972
- Nature
- Synthetic
- Biochemical name
- Cyclopamine
- Biological description
Cell-permeable inhibitor of hedgehog (Hh) signaling, via direct inhibition of Smo (Smoothened), the accessory protein to the putative Hh receptor. Anticancer and teratogenic activity in vivo.
- Canonical SMILES
- CC1CC2C(C(C3(O2)CCC4C5CC=C6CC(CCC6(C5CC4=C3C)C)O)C)NC1
- Isomeric SMILES
- C[C@H]1C[C@@H]2[C@H]([C@H]([C@]3(O2)CC[C@H]4[C@@H]5CC=C6C[C@H](CC[C@@]6([C@H]5CC4=C3C)C)O)C)NC1
- InChI
- InChI=1S/C27H41NO2/c1-15-11-24-25(28-14-15)17(3)27(30-24)10-8-20-21-6-5-18-12-19(29)7-9-26(18,4)23(21)13-22(20)16(27)2/h5,15,17,19-21,23-25,28-29H,6-14H2,1-4H3/t15-,17+,19-,20-,21-,23-,24+,25-,26-,27-/m0/s1
- InChIKey
- QASFUMOKHFSJGL-LAFRSMQTSA-N
- IUPAC name
- (3S,3'R,3'aS,6'S,6aS,6bS,7'aR,9R,11aS,11bR)-3',6',10,11b-tetramethylspiro[2,3,4,6,6a,6b,7,8,11,11a-decahydro-1H-benzo[a]fluorene-9,2'-3a,4,5,6,7,7a-hexahydro-3H-furo[3,2-b]pyridine]-3-ol
Storage
- Shipped at conditions
- Ambient - Can Ship with Ice
- Appropriate short-term storage conditions
- -20°C
- Appropriate long-term storage conditions
- -20°C
- Storage information
- Store in the dark, Store under desiccating conditions, This product is air and light sensitive and impurities can occur as a result of air oxidation or due to metabolism by microbes
Supplementary info
- This supplementary information is collated from multiple sources and compiled automatically.
- Activity summary
The Smoothened (SMO) protein also known as Sonic Hedgehog receptor plays a mechanical role in the Hedgehog (Hh) signaling pathway. This protein acts as a transmembrane receptor that transmits signals from the cell surface to the interior. Smoothened has a molecular mass of approximately 86 kDa and is expressed in several tissues including the brain kidney and liver. Its activity requires the presence of another protein Patched which regulates Smoothened by inhibiting or permitting its signaling depending on Hedgehog ligand binding.
- Biological function summary
Smoothened is essential for the Hh signaling pathway which is pivotal for embryonic development and tissue regeneration. In this context Smoothened participates in a complex that includes Patched and Gli family transcription factors. This complex orchestrates the transcription of target genes necessary for cellular proliferation differentiation and tissue organization. Smoothened’s role in activating transcription factors makes it integral to modulating gene expression in response to external Hh signals.
- Pathways
Smoothened is a central component of the Hedgehog signaling pathway which plays an important role in cell differentiation and organogenesis. Two of the significant pathways it influences are the Sonic Hedgehog (Shh) and Indian Hedgehog (Ihh) signaling pathways. Within these pathways Smoothened interacts closely with the protein Patched which inhibits Smoothened in the absence of Hedgehog ligands. The downstream activation of Smoothened results in the modulation of Gli transcription factors altering the expression of various developmental genes.
- Associated diseases and disorders
Smoothened is closely linked to conditions such as basal cell carcinoma and medulloblastoma. Dysregulation or mutations in Smoothened can lead to aberrant activation of Hedgehog signaling contributing to the development and progression of these cancers. The protein Gli as part of the same signaling cascade is also heavily involved in the transcriptional changes associated with these disorders. Inhibitors like Cyclopamine sometimes in an ethanol solution target Smoothened to mitigate its pathological signaling and offer therapeutic approaches for these types of cancers.
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Chemical Structure - Cyclopamine (ethanol solution), Hh signaling inhibitor (ab146596)
2D chemical structure image of ab146596, Cyclopamine (ethanol solution), Hh signaling inhibitor
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