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AB120392

Cyclopamine, Hh signaling inhibitor

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(4 Publications)

MW 411.6 Da, Purity >98%. 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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Chemical Structure - Cyclopamine, Hh signaling inhibitor (AB120392)
  • Chemical Structure

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Chemical Structure - Cyclopamine, Hh signaling inhibitor (AB120392)

2D chemical structure image of ab120392, Cyclopamine, Hh signaling inhibitor

Key facts

CAS number

4449-51-8

Purity

>98%

Form

Solid

form

Source

Veratrum californicum

Molecular weight

411.6 Da

Molecular formula

C<sub>2</sub><sub>7</sub>H<sub>4</sub><sub>1</sub>NO<sub>2</sub>

PubChem

442972

Nature

Native

Solubility

Soluble in ethanol to 5 mM

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

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Complementary Products

Biochemicals

AB142160

SAG (Smo agonist), Smoothened agonist

Chemical Structure - SAG (Smo agonist), Smoothened agonist (AB142160)

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Biochemicals

AB120962

SB 415286, GSK3 inhibitor

Chemical Structure - SB 415286, GSK3 inhibitor (AB120962)

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Biochemicals

AB120488

Z-D(OMe)E(OMe)VD(OMe)-FMK, Cell permeable caspase-3 inhibitor

Functional Studies - Z-D(OMe)E(OMe)VD(OMe)-FMK, Cell permeable caspase-3 inhibitor (AB120488)

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Biochemicals

AB120891

BIO, GSK3 inhibitor; cell-permeable

Immunocytochemistry/ Immunofluorescence - BIO, GSK3 inhibitor; cell-permeable (AB120891)

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Properties and storage information

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 under desiccating conditions|The product can be stored for up to 12 months
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Supplementary information

This supplementary information is collated from multiple sources and compiled automatically.

Sonic Hedgehog also known as SHH is a protein that plays an important role in cell signaling during embryonic development. It has alternative names like 'HHG-1' and '5h4'. The Sonic Hedgehog protein is about 45 kDa in mass. Scientists find SHH expression in various tissues including the brain lungs and limb buds. Its activity plays a role in the organization of several tissue structures during development helping to regulate cellular growth and differentiation processes.
Biological function summary

Sonic Hedgehog is critical for the vertebrate embryonic patterning and organogenesis. It functions as a signaling molecule and is part of the Hedgehog signaling complex. The protein acts by binding to the Patched receptor further influencing the Smoothened transducer in cellular signaling cascades. This signaling contributes to the proper formation of limbs central nervous system structures and other vital organs in early development stages.

Pathways

Sonic Hedgehog participates in essential signaling pathways such as the Hedgehog pathway and the Wnt signaling pathway. It interacts with proteins including the Patched and Smoothened to facilitate downstream genetic transcription regulation. Through these pathways Sonic Hedgehog influences the transcription of specific genes that control cell growth. These interactions contribute to the regulation of different cell types and the organization of distinct tissue areas.

Sonic Hedgehog connects to issues like cancer and congenital malformations. Aberrations in its signaling can lead to conditions such as basal cell carcinoma and holoprosencephaly. Sonic Hedgehog through its influence on the Hedgehog signaling pathway implicates interactions with other proteins like GLI transcription factors and Patched. These interactions can dysregulate cellular processes and result in disease states when not functioning correctly.
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Product protocols

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Publications (4)

Recent publications for all applications. Explore the full list and refine your search

Nature communications 11:414 PubMed31964872

2020

Structural insight into small molecule action on Frizzleds.

Applications

Unspecified application

Species

Unspecified reactive species

Paweł Kozielewicz,Ainoleena Turku,Carl-Fredrik Bowin,Julian Petersen,Jana Valnohova,Maria Consuelo Alonso Cañizal,Yuki Ono,Asuka Inoue,Carsten Hoffmann,Gunnar Schulte

Cell death & disease 10:574 PubMed31366904

2019

GLI1 activation by non-classical pathway integrin αβ/ERK1/2 maintains stem cell-like phenotype of multicellular aggregates in gastric cancer peritoneal metastasis.

Applications

Unspecified application

Species

Unspecified reactive species

Hui Dong,Hongchang Liu,Wen Zhou,Fan Zhang,Chuan Li,Jun Chen,Chenjun Tan,Bo Tang,Peiwu Yu

Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research 34:533-546 PubMed30352124

2018

Inactivation of Nell-1 in Chondrocytes Significantly Impedes Appendicular Skeletogenesis.

Applications

Unspecified application

Species

Unspecified reactive species

Huichuan Qi,Jong Kil Kim,Pin Ha,Xiaoyan Chen,Eric Chen,Yao Chen,Jiayi Li,Hsin Chuan Pan,Mengliu Yu,Yasamin Mohazeb,Sophia Azer,Lloyd Baik,Jin Hee Kwak,Kang Ting,Xinli Zhang,Min Hu,Chia Soo

Aging and disease 8:442-457 PubMed28840059

2017

Dopamine Burden Induced the Inactivation of Sonic Hedgehog Signaling to Cognitive Decline in Minimal Hepatic Encephalopathy.

Applications

Unspecified application

Species

Unspecified reactive species

Saidan Ding,Jianjing Yang,Xueli Huang,Leping Liu,Jiangnan Hu,Zhu Xu,Qichuan Zhuge
View all publications
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