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| CAS No.: | 4449-51-8 |
|---|---|
| Name: | CYCLOPAMINE |
| Article Data: | 7 |
| Molecular Structure: | |
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| Formula: | C27H41NO2 |
| Molecular Weight: | 411.628 |
| Synonyms: | Veratraman-3-ol, 17,23-epoxy-, (3b,23b)-;(-)-Cyclopamine;11-Deoxojervine;11-Deoxyjervine;Cyclopamine(8CI);Jervine, 11-deoxo- (7CI); |
| Density: | 1.14 g/cm3 |
| Melting Point: | 236-238 °C |
| Boiling Point: | 550.794 °C at 760 mmHg |
| Flash Point: | 286.91 °C |
| Solubility: | DMSO: soluble |
| Appearance: | White crystalline solid |
| Hazard Symbols: |
 Xi
|
| Safety: | 22-24/25 |
| PSA: | 41.49000 |
| LogP: | 5.33070 |
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C33H45NO4S
- 4449-51-8
cyclopamine
| 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% |
| 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; |
| Conditions | Yield |
|---|---|
| With water at 37℃; pH=7; aq. phosphate buffer; Inert atmosphere; |
| Conditions | Yield |
|---|---|
| With b-glucuronidase from E. Coli at 37℃; for 2h; pH=7; aq. phosphate buffer; Enzymatic reaction; |
- 4449-51-8
cyclopamine
| 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
| 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% |
| Conditions | Yield |
|---|---|
| With sodium hydrogencarbonate In toluene; acetonitrile for 2.5h; Heating; | 94% |
| With sodium hydrogencarbonate In toluene; acetonitrile for 2.5h; Reflux; | 94% |
| Conditions | Yield |
|---|---|
| With dmap; triethylamine In 1-Propyl acetate at 20℃; for 4h; Inert atmosphere; Large scale; | 91.8% |
| Conditions | Yield |
|---|---|
| With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 6h; | 85% |
| Conditions | Yield |
|---|---|
| With pyridine In N,N-dimethyl-formamide at 20℃; for 20h; | 85% |
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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. |