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Cyclopamine

Molecular FormulaC₂₇H₄₁NO₂
Average mass411.620 Da
Monoisotopic mass411.313721 Da
ChemSpider ID391275

- 10 of 10 defined stereocentres

More details:

Featured data source

Names and Synonyms
Database ID(s)

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

(3β,17β,22S,23R)-17,23-Epoxyveratraman-3-ol [ACD/IUPAC Name]

(3β,22S,23R)-17,23-Epoxyveratraman-3-ol [ACD/IUPAC Name]

(3β,22S,23R)-17,23-Époxyvératraman-3-ol [French] [ACD/IUPAC Name]

(3β,22S,23R)-17,23-Epoxyveratrumaman-3-ol [German] [ACD/IUPAC Name]

11-deoxojervine

4449-51-8 [RN]

Cyclopamine [Wiki]

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)-

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-, (3S,3'R,3a'S,6'S,6aS,6bS,7a'R,9R,11aS,11bR)- [ACD/Index Name]

Veratraman-3-ol, 17,23-epoxy-, (3β,23β)-

More...

ZH658AJ192

(2'R,3S,3'R,3a'S,6aS,6bS,6'S,7a'R,11aS,11bR)-3',6',10,11b-tetramethyl-1,2,3,3a',4,4',5',6,6a,6b,6',7,7',7a',8,11,11a,11b-octadecahydro-3'H-spiro[benzo[a]fluorene-9,2'-furo[3,2-b]pyridin]-3-ol

(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-tetramethyl-spiro[9H-benzo[a]fluorene-9,2'(3'H)-furo[3,2-b]pyridin]-3-ol

(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

(3S,3'R,3a'S,6aS,6bS,6'S,7a'R,9R,11aS,11bR)-3',6',10,11b-tetramethyl-1,2,3,3a',4,4',5',6,6a,6b,6',7,7',7a',8,11,11a,11b-octadecahydro-3'H-spiro[benzo[a]fluorene-9,2'-furo[3,2-b]pyridin]-3-ol

(3S,3'R,3'AS,6'S,6AS,6BS,7'AR,9R,11AS,11BR)-3',6',10,11B-TETRAMETHYL-1,2,3,3'A,4,4',5',6,6',6A,6B,7,7',7'A,8,11,11A,11B-OCTADECAHYDRO-3'H-SPIRO[CYCLOHEXA[A]FLUORENE-9,2'-FURO[3,2-B]PYRIDINE]-3-OL

(3S,3'R,3'AS,6'S,6AS,6BS,7'AR,9R,11AS,11BR)-3',6',10,11B-TETRAMETHYL-2,3,3'A,4,4',5',6,6',6A,6B,7,7',7'A,8,11,11A-HEXADECAHYDRO-1H,3'H-SPIRO[CYCLOHEXA[A]FLUORENE-9,2'-FURO[3,2-B]PYRIDINE]-3-OL

(3S,3'R,3'aS,6'S,6aS,6bS,7'aR,9R,11aS,11bR)-3',6',10,11b-tetramethyl-3-spiro[2,3,4,6,6a,6b,7,8,11,11a-decahydro-1H-benzo[i]fluorene-9,2'-3a,4,5,6,7,7a-hexahydro-3H-furo[4,5-b]pyridine]ol

(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

(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[i]fluorene-9,2'-3a,4,5,6,7,7a-hexahydro-3H-furo[4,5-b]pyridine]-3-ol

[3H]-Cyclopamine.11-Deoxojervine

108-93-0 [RN]

1178510-81-0 [RN]

11-Deoxyjervine

BSPBio_001032

Cy5 NHS Ester |

CY8

cyclopamine(11-deoxojervine)

cyclopamine, [3h]-

Cyclopamine, V. californicum - CAS 4449-51-8 - Calbiochem

Cyclopamine|11-Deoxojervine

GY0750000

Jervine, 11-deoxo-

MFCD09878269 [MDL number]

NSC734950

Spiro(9H-benzo(a)fluorene-9,2'(3'H)-furo(3,2-b)pyridin)-3-o l, 1,2,3,3'a,4,4',5',6,6',6a,6b,7,7',7'a,8,11,11a,11b-octa deca hydro-3',6',10,11b-tetramethyl-, (2'R,3S,3'R,3'aS,6'S,6aS,6bS,7'aR,11aS,11bR)-Veratraman-3-ol, 17,23-epoxy-, (3-β,23-β)-

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)- (9CI)

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)-

UNII:ZH658AJ192

UNII-ZH658AJ192

Veratraman-3-ol, 17,23-epoxy-, (3-β,23-β)-

环杷明 [Chinese]

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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

C10798 [DBID]

C4116_SIGMA [DBID]

nchembio753-comp1 [DBID]

Experimental data
Predicted - ACD/Labs
Predicted - EPISuite
Predicted - ChemAxon
Predicted - Mcule

Experimental Physico-chemical Properties
- Experimental Solubility:
  
  Soluble to 5 mM in ethanol Tocris Bioscience 1623

Miscellaneous

Toxicity:

Organic Compound; Amine; Ether; Plant Toxin; Natural Compound Toxin, Toxin-Target Database T3D4082
Target Organs:

Beta Amyloid modulator TargetMol T2825

Bio Activity:

Beta Amyloid TargetMol T2825

Biochemicals & small molecules/Antagonists & inhibitors Hello Bio HB2965

Cell Biology Tocris Bioscience 1623

Cell process/Stem cells/Stem cell signaling Hello Bio HB2965

Cell signaling/Hedgehog signaling Hello Bio HB2965

Hedgehog Signaling Tocris Bioscience 1623

Inhibitor of Hedgehog (Hh) signaling Tocris Bioscience 1623

Inhibitor of hedgehog (Hh) signaling, likely via direct inhibition of Smoothened, the accessory protein to the putative Hh receptor Patched. Anticancer and teratogenic in vivo. Depletes stem-like canc er cells in glioblastoma and blocks tumor engraftment. Can also be used to induce differentiation of human embryonic stem cells (hESCs) into hormone-expressing endocrine cells. Tocris Bioscience 1623

Inhibitor of hedgehog (Hh) signaling, likely via direct inhibition of Smoothened, the accessory protein to the putative Hh receptor Patched. Anticancer and teratogenic in vivo. Depletes stem-like cancer cells in glioblastoma and blocks tumor engraftment. Can also be used to induce differentiation of human embryonic stem cells (hESCs) into hormone-expressing endocrine cells. Tocris Bioscience 1623

Neuroscience TargetMol T2825

Receptors & Transporters/G protein coupled receptors/Smo Hello Bio HB2965

Signal Transduction Tocris Bioscience 1623

Smo and hedgehog (Hh) signaling inhibitor. Also depletes stem like cancer cells. Hello Bio HB2965

Smo Inhibitor and hedgehog (Hh) signaling inhibitor. Blocks abnormal cell growth associated with fibroblast Ptch and Smo oncogenic mutations. Also induces apoptosis and arrests cell cycle at G0/G1 phase and depletes stem like cancer cells. Shows anticancer activity. Hello Bio HB2965

Smo Inhibitor and hedgehog (Hh) signaling inhibitor. Depletes stem like cancer cells and induces hESCs into endocrine cells. Blocks abnormal cell growth associated with fibroblast Ptch and Smo oncogenic mutations. Also induces apoptosis and arrests cell cycle at G0/G1 phase and depletes stem like cancer cells. Shows anticancer activity. Hello Bio HB2965

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density:	1.1±0.1 g/cm³
Boiling Point:	550.8±50.0 °C at 760 mmHg
Vapour Pressure:	0.0±3.4 mmHg at 25°C
Enthalpy of Vaporization:	95.5±6.0 kJ/mol
Flash Point:	286.9±30.1 °C
Index of Refraction:	1.583
Molar Refractivity:	120.7±0.4 cm³
#H bond acceptors:	3
#H bond donors:	2
#Freely Rotating Bonds:	0
#Rule of 5 Violations:	1

ACD/LogP:	5.44
ACD/LogD (pH 5.5):	2.63
ACD/BCF (pH 5.5):	10.55
ACD/KOC (pH 5.5):	24.80
ACD/LogD (pH 7.4):	2.88
ACD/BCF (pH 7.4):	19.12
ACD/KOC (pH 7.4):	44.94
Polar Surface Area:	41 Å²
Polarizability:	47.9±0.5 10^-24cm³
Surface Tension:	46.1±5.0 dyne/cm
Molar Volume:	361.0±5.0 cm³

Predicted data is generated using the US Environmental Protection Agency�s EPISuite™

                        
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  4.90

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  494.05  (Adapted Stein & Brown method)
    Melting Pt (deg C):  209.82  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.1E-012  (Modified Grain method)
    Subcooled liquid VP: 2.84E-010 mm Hg (25 deg C, Mod-Grain method)

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  1.724
       log Kow used: 4.90 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  72.573 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aliphatic Amines
       Vinyl/Allyl Ethers

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   7.52E-012  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  9.739E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.90  (KowWin est)
  Log Kaw used:  -9.512  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  14.412
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.1489
   Biowin2 (Non-Linear Model)     :   0.0006
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.0410  (months      )
   Biowin4 (Primary Survey Model) :   3.1100  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1036
   Biowin6 (MITI Non-Linear Model):   0.0012
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.9359
 Ready Biodegradability Prediction:   NO

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  3.79E-008 Pa (2.84E-010 mm Hg)
  Log Koa (Koawin est  ): 14.412
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  79.2 
       Octanol/air (Koa) model:  63.4 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 338.0475 E-12 cm3/molecule-sec
      Half-Life =     0.032 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    22.781 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    55.453121 E-17 cm3/molecule-sec
      Half-Life =     0.021 Days (at 7E11 mol/cm3)
      Half-Life =     29.759 Min
   Fraction sorbed to airborne particulates (phi): 1 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1.629E+005
      Log Koc:  5.212 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
    Rate constants can NOT be estimated for this structure!

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 3.074 (BCF = 1185)
       log Kow used: 4.90 (estimated)

 Volatilization from Water:
    Henry LC:  7.52E-012 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  1.58E+008  hours   (6.582E+006 days)
    Half-Life from Model Lake : 1.723E+009  hours   (7.18E+007 days)

 Removal In Wastewater Treatment:
    Total removal:              74.28  percent
    Total biodegradation:        0.65  percent
    Total sludge adsorption:    73.63  percent
    Total to Air:                0.00  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.00644         0.3          1000       
   Water     9.46            1.44e+003    1000       
   Soil      67.3            2.88e+003    1000       
   Sediment  23.2            1.3e+004     0          
     Persistence Time: 2.13e+003 hr

Click to predict properties on the Chemicalize site

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Cyclopamine

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