Cyclopamine

CAT: 0804-HY-17024-07Size: 1 gDry Ice: NoHazardous: No

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CAT#:0804-HY-17024-07Size:1 g

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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 Number	4449-51-8
PubChem CID	442972
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 Formula	C27H41NO2
Molecular Weight	411.6
XLogP	3.5
Topological Polar Surface Area	41.5
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	0
Heavy Atom Count	30
Formal Charge	0
Complexity	801

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

CAS: 4449-51-8

CID: 442972

Formula: C27H41NO2

MW: 411.6

Interactive 3D Structure

Loading 3D structure...

View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	411.6
XLogP3	3.5
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	0
Exact Mass	411.313729551
Monoisotopic Mass	411.313729551
Topological Polar Surface Area	41.5 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	801
Isotope Atom Count	0
Defined Atom Stereocenter Count	10
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes

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Catalog	Name
HY-128683-01	Cycloposine

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Catalog	Name
A8340-10	Cyclopamine

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