N-{2-[(3'R,7'aR)-3',6',10,11b-tetramethyl-3-oxo-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}-6-(3-phenylpropanamido)hexanamide

• ChemBase ID: 172042
• Molecular Formular: C44H63N3O4
• Molecular Mass: 697.98872
• Monoisotopic Mass: 697.48185751
• SMILES: C1(=O)CC2=CCC3C(C2(CC1)C)CC1=C(C2(CCC31)O[C@H]1C([C@H]2C)N(CC(C1)C)CCNC(=O)CCCCCNC(=O)CCc1ccccc1)C
• Canonical SMILES: CC1CN(CCNC(=O)CCCCCNC(=O)CCc2ccccc2)C2[C@@H](C1)OC1([C@@H]2C)CCC2C(=C1C)CC1C2CC=C2C1(C)CCC(=O)C2
• InChI: InChI=1S/C44H63N3O4/c1-29-25-39-42(47(28-29)24-23-46-40(49)13-9-6-10-22-45-41(50)17-14-32-11-7-5-8-12-32)31(3)44(51-39)21-19-35-36-16-15-33-26-34(48)18-20-43(33,4)38(36)27-37(35)30(44)2/h5,7-8,11-12,15,29,31,35-36,38-39,42H,6,9-10,13-14,16-28H2,1-4H3,(H,45,50)(H,46,49)/t29?,31-,35?,36?,38?,39-,42?,43?,44?/m1/s1
• InChIKey: WDHRPWOAMDJICD-BWBMXWGBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{2-[(3'R,7'aR)-3',6',10,11b-tetramethyl-3-oxo-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}-6-(3-phenylpropanamido)hexanamide
• IUPAC Traditional name: N-{2-[(3'R,7'aR)-3',6',10,11b-tetramethyl-3-oxo-1,2,3',3'a,4,5',6,6',6a,6b,7,7',7'a,8,11,11a-hexadecahydrospiro[cyclohexa[a]fluorene-9,2'-furo[3,2-b]pyridine]-4'-yl]ethyl}-6-(3-phenylpropanamido)hexanamide
• Synonyms: KAAD-Cyclopamine; 3-Keto-N-aminoethyl-N'-aminocaproyldihydrocinnamoyl Cyclopamine, >80%

Database IDs

• CAS Number: 306387-90-6
• PubChem SID: 164227952
• PubChem CID: 16760383

CALCULATED PROPERTIES

• Acid pKa: 15.530833
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.878715
• LogD (pH = 7.4): 4.53552
• Log P: 5.9973145
• Molar Refractivity: 204.6121 cm^3
• Polarizability: 80.17164 Å^3
• Polar Surface Area: 87.74 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Pale Yellow Solid

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - K171000

Cyclopamine demonstrates teratogenic properties and has been shown to reverse effects ofoncogenic mutations in Smoothened and Patched.1 The KAAD-Cyclopamine has shown 10-20 fold higher potency than cyclopamine in inhibition of β-Galactosidase expression in p2Ptch-1- cells, with similar or lower toxicity. KAAD-Cyclopamine compound is unstable in solution.

REFERENCES

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