potassium 1-[5-({2-[(3S,3'R,3'aS,7'aR)-3-hydroxy-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]-4'-yl]ethyl}carbamoyl)pentyl]-2-[(1E)-3-[(2E)-1-ethyl-3,3-dimethyl-5-sulfonato-2,3-dihydro-1H-indol-2-ylidene]prop-1-en-1-yl]-3,3-dimethyl-3H-indol-1-ium-5-sulfonate

• ChemBase ID: 165077
• Molecular Formular: C60H81KN4O9S2
• Molecular Mass: 1105.53484
• Monoisotopic Mass: 1104.50820387
• SMILES: c1c(ccc2c1C(C(=[N+]2CCCCCC(=O)NCCN1[C@@H]2[C@@H](CC(C1)C)OC1(CCC3C4CC=C5C[C@H](CCC5(C4CC3=C1C)C)O)[C@@H]2C)/C=C/C=C/1\C(c2cc(ccc2N1CC)S(=O)(=O)[O-])(C)C)(C)C)S(=O)(=O)[O-].[K+]
• Canonical SMILES: CCN1c2ccc(cc2C(/C/1=C\C=C\C1=[N+](CCCCCC(=O)NCCN2CC(C)C[C@@H]3[C@@H]2[C@@H](C)C2(O3)CCC3C(=C2C)CC2C3CC=C3C2(C)CC[C@@H](C3)O)c2c(C1(C)C)cc(cc2)S(=O)(=O)[O-])(C)C)S(=O)(=O)[O-].[K+]
• InChI: InChI=1S/C60H82N4O9S2.K/c1-10-63-50-22-19-42(74(67,68)69)33-48(50)57(5,6)53(63)15-14-16-54-58(7,8)49-34-43(75(70,71)72)20-23-51(49)64(54)29-13-11-12-17-55(66)61-28-30-62-36-37(2)31-52-56(62)39(4)60(73-52)27-25-44-45-21-18-40-32-41(65)24-26-59(40,9)47(45)35-46(44)38(60)3;/h14-16,18-20,22-23,33-34,37,39,41,44-45,47,52,56,65H,10-13,17,21,24-32,35-36H2,1-9H3,(H2-,61,66,67,68,69,70,71,72);/q;+1/p-1/t37?,39-,41+,44?,45?,47?,52-,56+,59?,60?;/m1./s1
• InChIKey: PLSNDDPWUVZUOK-OMIRHPFHSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: potassium 1-[5-({2-[(3S,3'R,3'aS,7'aR)-3-hydroxy-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]-4'-yl]ethyl}carbamoyl)pentyl]-2-[(1E)-3-[(2E)-1-ethyl-3,3-dimethyl-5-sulfonato-2,3-dihydro-1H-indol-2-ylidene]prop-1-en-1-yl]-3,3-dimethyl-3H-indol-1-ium-5-sulfonate
• IUPAC Traditional name: potassium 1-[5-({2-[(3S,3'R,3'aS,7'aR)-3-hydroxy-3',6',10,11b-tetramethyl-2,3,3',3'a,4,5',6,6',6a,6b,7,7',7'a,8,11,11a-hexadecahydro-1H-spiro[cyclohexa[a]fluorene-9,2'-furo[3,2-b]pyridine]-4'-yl]ethyl}carbamoyl)pentyl]-2-[(1E)-3-[(2E)-1-ethyl-3,3-dimethyl-5-sulfonatoindol-2-ylidene]prop-1-en-1-yl]-3,3-dimethylindol-1-ium-5-sulfonate
• Synonyms: Cy-3-Cyclopamine Potassium Salt; Cyanine-3 Cyclopamine Potassium Salt

Database IDs

• PubChem SID: 162259210
• PubChem CID: 71315031

CALCULATED PROPERTIES

• Acid pKa: -3.3496702
• H Acceptors: 11
• H Donor: 2
• LogD (pH = 5.5): 6.6117086
• LogD (pH = 7.4): 6.5987077
• Log P: 5.443016
• Molar Refractivity: 309.9012 cm^3
• Polarizability: 116.64166 Å^3
• Polar Surface Area: 182.45 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Brown Solid

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - C959300

A fluorescent deriviative of Cyclopamine, which demonstrates teratogenic properties and has been shown to reverse effects ofoncogenic mutations in Smoothened and Patched.1

REFERENCES

• Taipale, J., et al. Nature 406, 1005 (2000)
• Perron, M., et al. Development 130, 1565 (2003)