(1R,2S,4S,5'S,6R,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: 105611
• Molecular Formular: C27H46ClNO2
• Molecular Mass: 452.11264
• Monoisotopic Mass: 451.3217074
• SMILES: Cl.O[C@H]1CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@@]2([C@@H]4[C@@H](O[C@@]5(NC[C@H](CC5)C)[C@H]4C)C[C@@H]32)C)C1
• 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-XRWUXUKGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,4S,5'S,6R,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; (1R,2S,4S,5'S,6R,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0?,?.0?,?.0??,??]icosane-6,2'-piperidine]-16-ol hydrochloride
• IUPAC Traditional name: (1R,2S,4S,5'S,6R,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; (1R,2S,4S,5'S,6R,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0?,?.0?,?.0??,??]icosane-6,2'-piperidine]-16-ol hydrochloride
• Synonyms: 3β-Hydroxy-5α-tomatidane hydrochloride; 5α-Tomatidan-3β-ol hydrochloride; Tomatidine hydrochloride; 5α-Tomatidan-3β-ol; TOMATIDINE HYDROCHLORIDE

Database IDs

• CAS Number: 6192-62-7
• MDL Number: MFCD00133866
• Beilstein Number: 3920740
• PubChem SID: 162092718; 24900092
• PubChem CID: 16220013

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

Safety Information

• Storage Condition: 2-8°C, Desiccate
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥85%

DETAILS

MP Biomedicals - 02193506

Hydrochloride
Crystalline

Sigma Aldrich - T2909

Biochem/physiol Actions
Potent inhibitor of Staphylococcus aureus small-colony variants typically seen as complications of cystic fibrosis, with little or no effect on normal S. aureus strains.1 Also shows antiinflammatory activity by indirectly inhibiting iNOS and COX-2 pathways.2