(1R,2S,4S,5'S,6S,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-piperidine]-16-ol hydrochloride

• ChemBase ID: 178739
• Molecular Formular: C27H46ClNO2
• Molecular Mass: 452.11264
• Monoisotopic Mass: 451.3217074
• SMILES: C1[C@@H](C[C@H]2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@@H]1[C@H](C2)O[C@@]2([C@H]1C)NC[C@H](CC2)C)C)C)O.Cl
• Canonical SMILES: C[C@H]1CC[C@]2(NC1)O[C@@H]1[C@H]([C@@H]2C)[C@@]2([C@@H](C1)[C@@H]1CC[C@@H]3[C@]([C@H]1CC2)(C)CC[C@@H](C3)O)C.Cl
• InChI: InChI=1S/C27H45NO2.ClH/c1-16-7-12-27(28-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(29)8-10-25(18,3)21(20)9-11-26(22,24)4;/h16-24,28-29H,5-15H2,1-4H3;1H/t16-,17-,18-,19-,20+,21-,22-,23-,24-,25-,26-,27-;/m0./s1
• InChIKey: SXXHVPYRDFJKPG-VXJLCZPPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,4S,5'S,6S,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosane-6,2'-piperidine]-16-ol hydrochloride
• IUPAC Traditional name: tomatidine hydrochloride
• Synonyms: (3β,5α,22β,25S)-Spirosolan-3-ol Hydrochloride; Tomatidin Hydrochloride, >85%

Database IDs

• CAS Number: 6192-62-7
• PubChem SID: 164234649
• PubChem CID: 60196284

CALCULATED PROPERTIES

• Acid pKa: 18.296396
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.8373392
• LogD (pH = 7.4): 2.9038544
• Log P: 5.015457
• Molar Refractivity: 121.0968 cm^3
• Polarizability: 48.931477 Å^3
• Polar Surface Area: 41.49 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White Solid
• Melting Point: 281-284°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - T538500

A steriodal alkaloid structurally similar to Cyclopamine but does not inhibit hedgehog pathway. May be used as a negative control for Cyclopamine and KAAD-Cyclopamine.

REFERENCES

• Watkins, D.N., et al.: Nature, 422, 313 (2003)