4-(2-{[5-({2-[(3S,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)(2H10)pentyl]carbamoyl}ethyl)-2,2-difluoro-10,12-dimethyl-1λ5,3-diaza-2-boratricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaen-1-ylium-2-uide

• ChemBase ID: 162670
• Molecular Formular: C49H70BF2N5O4
• Molecular Mass: 841.9190064
• Monoisotopic Mass: 841.54889259
• SMILES: C1[C@@H](CC2=CCC3C(C2(C1)C)CC1=C(C2(CCC31)C(C1[C@H](O2)CC(CN1CCNC(=O)CCCCCNC(=O)CCc1ccc2n1[B-]([N+]1=C(C=C(C1=C2)C)C)(F)F)C)C)C)O
• Canonical SMILES: CC1CN(CCNC(=O)CCCCCNC(=O)CCc2ccc3n2[B-](F)(F)[N+]2=C(C)C=C(C2=C3)C)C2[C@@H](C1)OC1(C2C)CCC2C(=C1C)CC1C2CC=C2C1(C)CC[C@@H](C2)O
• InChI: InChI=1S/C49H70BF2N5O4/c1-30-24-44-47(34(5)49(61-44)20-18-39-40-15-11-35-26-38(58)17-19-48(35,6)42(40)28-41(39)33(49)4)55(29-30)23-22-54-45(59)10-8-7-9-21-53-46(60)16-14-36-12-13-37-27-43-31(2)25-32(3)56(43)50(51,52)57(36)37/h11-13,25,27,30,34,38-40,42,44,47,58H,7-10,14-24,26,28-29H2,1-6H3,(H,53,60)(H,54,59)/t30?,34?,38-,39?,40?,42?,44+,47?,48?,49?/m0/s1
• InChIKey: CQPRECBXTRAUSE-QEXJUGOOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(2-{[5-({2-[(3S,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)(^2H₁₀)pentyl]carbamoyl}ethyl)-2,2-difluoro-10,12-dimethyl-1λ^5,3-diaza-2-boratricyclo[7.3.0.0^3,^7]dodeca-1(12),4,6,8,10-pentaen-1-ylium-2-uide
• IUPAC Traditional name: 4-(2-{[5-({2-[(3S,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)(^2H₁₀)pentyl]carbamoyl}ethyl)-2,2-difluoro-10,12-dimethyl-1λ^5,3-diaza-2-boratricyclo[7.3.0.0^3,^7]dodeca-1(12),4,6,8,10-pentaen-1-ylium-2-uide
• Synonyms: Bodipy Cyclopamine-d10

Database IDs

• PubChem SID: 162256805
• PubChem CID: 71314180

CALCULATED PROPERTIES

• Acid pKa: 14.610145
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -3.4470232
• LogD (pH = 7.4): -1.6864699
• Log P: -0.22267419
• Molar Refractivity: 241.6739 cm^3
• Polarizability: 92.16448 Å^3
• Polar Surface Area: 98.84 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - B674802

A labelled fluorescent Cyclopamine derivative that retains potency in Shh signaling inhibition (IC50=150nM).

REFERENCES

• Chen, K.J., et al.: Genes Develop., 16, 2743 (2002)