(3S,3'R,3'aS,6'S,6aS,6bS,7'aR,9R,11aS,11bR)-4'-(2-aminoethyl)-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

• ChemBase ID: 160113
• Molecular Formular: C29H46N2O2
• Molecular Mass: 454.68774
• Monoisotopic Mass: 454.35592872
• SMILES: [C@H]1(CC2=CC[C@@H]3[C@@H]([C@]2(CC1)C)CC1=C([C@]2(CC[C@@H]31)O[C@H]1[C@H]([C@H]2C)N(C[C@H](C1)C)CCN)C)O
• Canonical SMILES: NCCN1C[C@@H](C)C[C@@H]2[C@@H]1[C@@H](C)[C@]1(O2)CC[C@@H]2C(=C1C)C[C@H]1[C@H]2CC=C2[C@]1(C)CC[C@@H](C2)O
• InChI: InChI=1S/C29H46N2O2/c1-17-13-26-27(31(16-17)12-11-30)19(3)29(33-26)10-8-22-23-6-5-20-14-21(32)7-9-28(20,4)25(23)15-24(22)18(29)2/h5,17,19,21-23,25-27,32H,6-16,30H2,1-4H3/t17-,19+,21-,22-,23-,25-,26+,27-,28-,29-/m0/s1
• InChIKey: QCFBFPHBSKOKSL-QBWUJNPXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,3'R,3'aS,6'S,6aS,6bS,7'aR,9R,11aS,11bR)-4'-(2-aminoethyl)-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
• IUPAC Traditional name: (3S,3'R,3'aS,6'S,6aS,6bS,7'aR,9R,11aS,11bR)-4'-(2-aminoethyl)-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]-3-ol
• Synonyms: (2'R,3S,3'R,3'aS,6'S,6aS,6bS,7'aR,11aS,11bR)-4'-(2-aminoethyl)-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; N-(2-Aminoethyl) Cyclopamine

Database IDs

• CAS Number: 334616-31-8
• PubChem SID: 162254248
• PubChem CID: 58682577

CALCULATED PROPERTIES

• Acid pKa: 18.204288
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.3790532
• LogD (pH = 7.4): 0.91898334
• Log P: 3.3825307
• Molar Refractivity: 135.4136 cm^3
• Polarizability: 53.66821 Å^3
• Polar Surface Area: 58.72 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid
• Melting Point: >175°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A608925

A 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)