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Cyclopamine

Cyclopamine structure

CAS No:
4449-51-8
Formula:
C27H41NO2
Chemical Name:
Cyclopamine
Synonyms:
Spiro[9H-benzo[a]fluorene-9,2′(3′H)-furo[3,2-b]pyridin]-3-ol,1,2,3,3′a,4,4′,5′,6,6′,6a,6b,7,7′,7′a,8,11,11a,11b-octadecahydro-3′,6′,10,11b-tetramethyl-,(2′R,3S,3′R,3′aS,6′S,6aS,6bS,7′aR,11aS,11bR)-;Cyclopamine;Veratraman-3-ol,17,23-epoxy-,(3β,23β)-;Jervine,11-deoxo-;(2′R,3S,3′R,3′aS,6′S,6aS,6bS,7′aR,11aS,11bR)-1,2,3,3′a,4,4′,5′,6,6′,6a,6b,7,7′,7′a,8,11,11a,11b-Octadecahydro-3′,6′,10,11b-tetramethylspiro[9H-benzo[a]fluorene-9,2′(3′H)-furo[3,2-b]pyridin]-3-ol;11-Deoxyjervine;11-Deoxojervine;(-)-Cyclopamine;11051-96-0;26108-61-2
Categories:
Biochemical Engineering > Inhibitors

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

Cyclopamine Basic Attributes

Molecular Weight：

411.62

Exact Mass：

411.62

UNII：

ZH658AJ192

NSC Number：

734950

DSSTox ID：

DTXSID6043709

HScode：

29349990

Characteristics

PSA：

41.5

XLogP3：

5.33070

Appearance：

solid

Density：

1.1±0.1 g/cm3

Melting Point：

224-227 °C

Boiling Point：

550.794°C at 760 mmHg

Flash Point：

286.9±30.1 °C

Refractive Index：

1.583

Water Solubility：

DMSO: soluble

Storage Conditions：

2-8°C

Safety Information

wgk germany：

safety instructions：

22-24/25

RTECS Number：

GY0750000

Marks：

Stability/Shelf Life：

Store in Freezer at - 20°C

GHS Classification：

|Warning|H341 (90.7%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]|P201, P202, P281, P308+P313, P405, and P501|Aggregated GHS information provided by 43 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Natural Pollution Sources：

...DERIVED FROM THE PLANT VERATRUM CALIFORNICUM.

Drug Information

Therapeutic Uses：

Plants have and continue to provide medicine with an abundance of pharmacologically interesting and useful chemicals. In recent years, cyclopamine, a steroidal alkaloid isolated from Veratrum californicum, has been instrumental in dissecting the sonic hedgehog pathway. This brief report outlines cyclopamine's discovery with discussion of its potential application to clinical dermatology.

Reported Fatal Dose：

3 OR 4. 3= MODERATELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 0.5-5 G/KG, BETWEEN 1 OZ & 1 PINT (OR 1 LB) FOR 70 KG PERSON (150 LB). 4= VERY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 50-500 MG/KG, BETWEEN 1 TEASPOON & 1 OZ FOR 70 KG PERSON (150 LB). /VERATRUM VIRIDE ALKALOIDS/

Metabolism/Metabolites：

Conversion to teratogen of cyclopamine by rumen microorganisms is not essential. Indeed, ruminant sheep and non-ruminant rabbits were about equally susceptible to cyclopamine on a body weight basis.

Mechanism of Action：

A NUMBER OF VERATRUM ALKALOIDS WERE TESTED IN PREGNANT SHEEP FOR TERATOGENICITY. THE COMPOUNDS JERVINE, CYCLOPAMINE...AND CYCLOPOSINE...PRODUCED DEFORMITIES SIMILAR TO NATURAL CASES. THE 3 TERATOGENIC COMPOUNDS ARE CLOSELY RELATED STEROIDAL FURANOPIPERIDINES, BUT CYCLOPAMINE IS THE TERATOGEN OF NATURAL IMPORTANCE BECAUSE OF PLANT CONCN. CLOSELY RELATED COMPD DEVOID OF THE FURAN RING DID NOT PRODUCE CYCLOPIA IN SHEEP, SUGGESTING THAT AN INTACT FURAN RING WAS REQUIRED FOR ACTIVITY, PERHAPS CONFERRING SOME ESSENTIAL CONFIGURATION ON THE MOLECULE.

MeSH Entry Terms：

cyclopamine

Cyclopamine Use and Manufacturing

Uses

Cyclopamine antibacterial properties. Cyclopamine demonstrates teratogenic properties and has been shown to reverse effects of oncogenic mutations in Smoothened and Patched.

Manufacturing Info：

11-Deoxojervine is a precursor for the biosynthesis of jervine in Veratrum grandiflorum.

Computed Properties

Molecular Weight:411.6
XLogP3:3.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Exact Mass:411.313729551
Monoisotopic Mass:411.313729551
Topological Polar Surface Area:41.5
Heavy Atom Count:30
Complexity:801
Defined Atom Stereocenter Count:10
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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CAS No.: 4449-51-8

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