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Cas Database

Name	Cyclopamine	EINECS	N/A
CAS No.	4449-51-8	Density	1.14 g/cm³
PSA	41.49000	LogP	5.33070
Solubility	DMSO: soluble	Melting Point	236-238 °C
Formula	C₂₇H₄₁NO₂	Boiling Point	550.794 °C at 760 mmHg
Molecular Weight	411.628	Flash Point	286.91 °C
Transport Information	N/A	Appearance	White crystalline solid
Safety	22-24/25	Risk Codes	N/A
Molecular Structure		Hazard Symbols	Xi
Synonyms	Veratraman-3-ol, 17,23-epoxy-, (3b,23b)-;(-)-Cyclopamine;11-Deoxojervine;11-Deoxyjervine;Cyclopamine(8CI);Jervine, 11-deoxo- (7CI);	Article Data	7

Cyclopamine Synthetic route

: 1198184-95-0
C33H45NO4S

: 4449-51-8
cyclopamine

Conditions

Conditions	Yield
Stage #1: C33H45NO4S With naphthalene; sodium In 1,2-dimethoxyethane at -78℃; for 3h; Inert atmosphere; Stage #2: With water; sodium hydrogencarbonate In 1,2-dimethoxyethane at -78 - 20℃; Inert atmosphere;	91%

: 469-59-0
jervine

: 4449-51-8
cyclopamine

Conditions

Conditions	Yield
With potassium hydroxide; hydrazine hydrate Heating; 1.) triethylene glycol, 120 deg C, 1 h, 2.) triethylene glycol, 200 deg C, 3 h;	51%
With sodium; hydrazine In diethylene glycol Heating;

: 1224886-42-3
C35H46N2O7

A: 41833-13-0
4-hydroxymethyl-2-nitrophenol

B: 4449-51-8
cyclopamine

Conditions

Conditions	Yield
With water at 37℃; pH=7; aq. phosphate buffer; Inert atmosphere;

: C56H79N5O21

A: 1366596-68-0
C22H32N4O12

B: 4449-51-8
cyclopamine

Conditions

Conditions	Yield
With b-glucuronidase from E. Coli at 37℃; for 2h; pH=7; aq. phosphate buffer; Enzymatic reaction;

: cycloposine

: 4449-51-8
cyclopamine

Conditions

Conditions	Yield
With water; 2-amino-2-hydroxymethyl-1,3-propanediol In ethanol; dimethyl sulfoxide at 37℃; for 22h; pH=7.2; pH-value; Reagent/catalyst; Solvent; Temperature; Enzymatic reaction;

: 4449-51-8
cyclopamine

: cyclopamine-4-ene-3-one

Conditions

Conditions	Yield
With aluminum isopropoxide; butanone for 6.5h; Oppenauer oxidation; Reflux;	99%
With aluminum isopropoxide; butanone for 6.5h; Oppenauer oxidation; Reflux; Inert atmosphere;	85%
With cyclohexanone; aluminum isopropoxide In toluene for 2h; Heating / reflux;	70%
With cyclohexanone; aluminum isopropoxide In toluene for 2h; Heating / reflux;	70%

: 4449-51-8
cyclopamine

: 106-96-7
propargyl bromide

: 1017893-81-0
N-propargylcyclopamine

Conditions

Conditions	Yield
With sodium hydrogencarbonate In toluene; acetonitrile for 2.5h; Heating;	94%
With sodium hydrogencarbonate In toluene; acetonitrile for 2.5h; Reflux;	94%

: 4449-51-8
cyclopamine

: 501-53-1
benzyl chloroformate

: 1037210-08-4
bis-CBz-cyclopamine

Conditions

Conditions	Yield
With dmap; triethylamine In 1-Propyl acetate at 20℃; for 4h; Inert atmosphere; Large scale;	91.8%

: C46H58N8O14

: 4449-51-8
cyclopamine

: C73H97N9O15

Conditions

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 6h;	85%

: C38H36N2O20

: 4449-51-8
cyclopamine

: C59H72N2O19

Conditions

Conditions	Yield
With pyridine In N,N-dimethyl-formamide at 20℃; for 20h;	85%

Cyclopamine Specification

The Cyclopamine is an organic compound with the formula C₂₇H₄₁NO₂. The IUPAC name of this chemical is (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. With the CAS registry number 4449-51-8, it is also named as 11-Deoxojervine. The product's categories are Intermediates & Fine Chemicals; Pharmaceuticals; Steroids; Lipid Signaling. Besides, it is a white crystalline solid, which should be stored in a dark dry and well-ventilated place.

The Cyclopamine can prevent the fetal brain from dividing into two lobes (holoprosencephaly) and cause the development of a single eye (cyclopia). It does so by suppressing the hedgehog gene (Hh). 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.

Physical properties about Cyclopamine are: (1)ACD/LogP: 6.10; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 3.005; (4)ACD/LogD (pH 7.4): 3.263; (5)ACD/BCF (pH 5.5): 20.45; (6)ACD/BCF (pH 7.4): 37.05; (7)ACD/KOC (pH 5.5): 39.815; (8)ACD/KOC (pH 7.4): 72.134; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 41.49 Å²; (13)Index of Refraction: 1.583; (14)Molar Refractivity: 120.716 cm³; (15)Molar Volume: 360.973 cm³; (16)Polarizability: 47.856×10^-24cm³; (17)Surface Tension: 46.114 dyne/cm; (18)Density: 1.14 g/cm³; (19)Flash Point: 286.91 °C; (20)Enthalpy of Vaporization: 95.514 kJ/mol; (21)Boiling Point: 550.794 °C at 760 mmHg.

You can still convert the following datas into molecular structure:
(1)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
(2)InChI: InChI=1/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
(3)InChIKey: QASFUMOKHFSJGL-LAFRSMQTBZ
(4)Std. 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
(5)Std. InChIKey: QASFUMOKHFSJGL-LAFRSMQTSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
hamster	LDLo	oral	170mg/kg (170mg/kg)		Proceedings of the Society for Experimental Biology and Medicine. Vol. 149, Pg. 302, 1975.
mouse	LDLo	oral	180mg/kg (180mg/kg)		Proceedings of the Society for Experimental Biology and Medicine. Vol. 149, Pg. 302, 1975.

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