N-[(3'R,3'aS,4aR,6'S,6aR,6bS,7'aR,9S,12aS,12bS)-3',6',11,12b-tetramethyl-2,3,3'a,4,4',4a,5,5',6,6',6a,6b,7,7',7'a,8,10,12,12a,12b-icosahydro-1H,3'H-spiro[azuleno[2,1-a]naphthalene-9,2'-furo[3,2-b]pyridine]-3-yl]methanesulfonamide hydrochloride

• ChemBase ID: 171730
• Molecular Formular: C29H49ClN2O3S
• Molecular Mass: 541.22896
• Monoisotopic Mass: 540.31524212
• SMILES: C1C(C[C@@H]2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2C(=C(C[C@@]3(CC2)[C@@H]([C@H]2[C@H](O3)C[C@@H](CN2)C)C)C)C1)C)NS(=O)(=O)C.Cl
• Canonical SMILES: C[C@@H]1CN[C@@H]2[C@@H](C1)O[C@@]1([C@@H]2C)CC[C@@H]2C(=C(C1)C)C[C@H]1[C@H]2CC[C@H]2[C@]1(C)CCC(C2)NS(=O)(=O)C.Cl
• InChI: InChI=1S/C29H48N2O3S.ClH/c1-17-12-26-27(30-16-17)19(3)29(34-26)11-9-22-23-7-6-20-13-21(31-35(5,32)33)8-10-28(20,4)25(23)14-24(22)18(2)15-29;/h17,19-23,25-27,30-31H,6-16H2,1-5H3;1H/t17-,19+,20+,21?,22-,23-,25-,26+,27-,28-,29-;/m0./s1
• InChIKey: LICVMCOINZNZNW-YLEANGGXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(3'R,3'aS,4aR,6'S,6aR,6bS,7'aR,9S,12aS,12bS)-3',6',11,12b-tetramethyl-2,3,3'a,4,4',4a,5,5',6,6',6a,6b,7,7',7'a,8,10,12,12a,12b-icosahydro-1H,3'H-spiro[azuleno[2,1-a]naphthalene-9,2'-furo[3,2-b]pyridine]-3-yl]methanesulfonamide hydrochloride
• IUPAC Traditional name: N-[(3'R,3'aS,4aR,6'S,6aR,6bS,7'aR,9S,12aS,12bS)-3',6',11,12b-tetramethyl-1,2,3,3'a,4,4',4a,5,5',6,6',6a,6b,7,7',7'a,8,10,12,12a-icosahydro-3'H-spiro[azuleno[2,1-a]naphthalene-9,2'-furo[3,2-b]pyridine]-3-yl]methanesulfonamide hydrochloride
• Synonyms: N-[(2S,3R,3'R,3aS,4'aR,6S,6'aR,6'bS,7aR,12'aS,12'bS)-2',3',3a,4,4',4'a,5,5',6,6',6'a,6'b,7,7',7a,8',10',12',12'a,12'b-Eicosahydro-3,6,11',12'b-tetramethylspiro[furo[3,2-b]pyridine-2(3H),9'(1'H)-naphth[2,1-a]azulen]-3'-yl]methanesulfonamide Hydrochloride; IPI-926 Hydrochloride

Database IDs

• CAS Number: 1169829-40-6
• PubChem SID: 164227640
• PubChem CID: 71749523

CALCULATED PROPERTIES

• Acid pKa: 11.576916
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.4787406
• LogD (pH = 7.4): 1.1815326
• Log P: 3.5654418
• Molar Refractivity: 140.7764 cm^3
• Polarizability: 57.05339 Å^3
• Polar Surface Area: 67.43 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - I739300

A hedgehog inhibitor used in combination with other chemotherapeutics (e.g., docetaxel, mitoxantrone, estramustine, doxorubicin, etoposide, vinblastine, carboplatin, vinorelbine) for treating pancreatic cancer.

REFERENCES

• Shafaee, et al.: Cancer Chemother. Pharmacol., 58, 765 (2006)