环巴明

Description

Cyclopamine · CAS 4449-51-8 · C27H41NO2. UNII ZH658AJ192.

Identification

CAS Registry Number	4449-51-8
PubChem CID	442972
Molecular formula	C27H41NO2
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
UNII (FDA)	ZH658AJ192

Computed Descriptors

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
Heavy Atom Count	30
Formal Charge	0

Physical description & handling notes

• 218.7 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID6043709]
• 219.1 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID6043709]

GHS Hazard Classification

Reported hazard statements	H341 (88.6%), H361 (90.9%)

Documented Uses

• It is a teratogen isolated from the corn lily (Veratrum californicum) that causes usually fatal birth defects. Cyclopamine is useful in studying the role of Hh in normal development, and as a potential treatment for certain cancers in which Hh is overexpressed.
• 11-Deoxojervine is a precursor for the biosynthesis of jervine in Veratrum grandiflorum.
• 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.
• 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/
• 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.

Synonyms

CYCLOPAMINE; 4449-51-8; 11-Deoxojervine; 11-Deoxyjervine; DTXSID6043709; Alkaloid V; ZH658AJ192; NSC-734950; DTXCID4023709; Veratraman-3-ol, 17,23-epoxy-, (3beta,23beta)-; (3beta23R)-17,23-Epoxyveratraman-3-ol; 3,4'-Dinitroflavone; RefChem:129819; 628-058-8; MFCD09878269; Jervine, 11-deoxo-

Frequently Asked Questions

What are the CAS number and molecular formula of Cyclopamine?

CAS 4449-51-8; molecular formula C27H41NO2; molecular weight — g/mol.

What other names is Cyclopamine known by?

CYCLOPAMINE, 4449-51-8, 11-Deoxojervine, 11-Deoxyjervine, DTXSID6043709, Alkaloid V.

Is Cyclopamine classified as hazardous?

Hazard statements reported: H341, H361.

Facts on this page are taken from PubChem (US National Library of Medicine) and Wikidata. Grade-specific data — assay, moisture, particle size, packaging, shelf life — is issued per batch on the COA and is not published here.