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Cyclopamine

CAT: 0804-HY-17024-06Size: 500 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-17024-06Size:500 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Cyclopamine is a Hedgehog (Hh) pathway antagonist with an IC50 of 46 nM in the Hh cell assay. Cyclopamine is also a selective Smo inhibitor.
CAS Number
4449-51-8
Product Name Alternative
11-Deoxojervine
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Endogenous Metabolite; Hedgehog; Smo
Type
Natural Products
Related Pathways
Metabolic Enzyme/Protease; Stem Cell/Wnt
Applications
Cancer-programmed cell death
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/Cyclopamine.html
Concentration
10mM
Purity
99.97
Solubility
DMSO : 5 mg/mL (ultrasonic) |Ethanol : 5 mg/mL (ultrasonic)
Smiles
CC1=C2[C@@]([C@@]3([H])[C@]([C@@]4(C(C[C@@H](O)CC4)=CC3)C)([H])C2)([H])CC[C@@]15[C@@H]([C@@]6([H])[C@](C[C@H](C)CN6)([H])O5)C
Molecular Formula
C27H41NO2
Molecular Weight
411.62
Precautions
H302, H315, H319, H335
References & Citations
[1]Peukert S, et al. Identification and structure-activity relationships of ortho-biphenyl carboxamides as potent Smoothened antagonists inhibiting the Hedgehog signaling pathway. Bioorg Med Chem Lett, 2009, 19 (2), 328-331.|[2]Berman DM, et al. Widespread requirement for Hedgehog ligand stimulation in growth of digestive tract tumours. Nature, 2003, 425 (6960), 846-851.|[3]Thayer SP, et al. Hedgehog is an early and late mediator of pancreatic cancer tumorigenesis. Nature, 2003, 425 (6960), 851-856.|[4]Ma W, et al. Reduced Smoothened level rescued Aβ-induced memory deficits and neuronal inflammation in animal models of Alzheimer's disease. J Genet Genomics. 2018 May 20;45 (5) :237-246.|[5]Qi Wan, et al. Overexpression of Laminin α4 Facilitates Proliferation and Migration of Fibroblasts in Knee Arthrofibrosis by Targeting Canonical Shh/Gli1 Signaling. Connect Tissue Res. 2020 May 24.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

Cyclopamine

Cyclopamine is a member of piperidines. It has a role as a glioma-associated oncogene inhibitor.

CAS Number4449-51-8
PubChem CID442972
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
Molecular FormulaC27H41NO2
Molecular Weight411.6
XLogP3.5
Topological Polar Surface Area41.5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count0
Heavy Atom Count30
Formal Charge0
Complexity801
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
Chemical Structure
2D Structure
2D structure of Cyclopamine
CAS: 4449-51-8
CID: 442972
Formula: C27H41NO2
MW: 411.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight411.6
XLogP33.5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count0
Exact Mass411.313729551
Monoisotopic Mass411.313729551
Topological Polar Surface Area41.5 Ų
Heavy Atom Count30
Formal Charge0
Complexity801
Isotope Atom Count0
Defined Atom Stereocenter Count10
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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