(1S,2R,5S,7S,10S,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.02,11.05,10.015,23.017,22]tetracosan-7-ol

• ChemBase ID: 104884
• Molecular Formular: C27H45NO
• Molecular Mass: 399.6523
• Monoisotopic Mass: 399.35011507
• SMILES: O[C@H]1CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@@]2([C@@H]4[C@@H](N5[C@@H]([C@H]4C)CC[C@H](C)C5)C[C@@H]32)C)C1
• Canonical SMILES: O[C@H]1CC[C@]2([C@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1C[C@H]1[C@@H]2[C@H](C)[C@@H]2N1C[C@H](CC2)C)C)C
• InChI: InChI=1S/C27H45NO/c1-16-5-8-23-17(2)25-24(28(23)15-16)14-22-20-7-6-18-13-19(29)9-11-26(18,3)21(20)10-12-27(22,25)4/h16-25,29H,5-15H2,1-4H3/t16-,17+,18-,19-,20+,21-,22-,23+,24-,25-,26-,27-/m0/s1
• InChIKey: JALVTHFTYRPDMB-HRRTYWNUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S,7S,10S,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.0^2,^1^1.0^5,^1^0.0^1^5,^2^3.0^1^7,^2^2]tetracosan-7-ol; (1S,2R,5S,7S,10S,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.0?,??.0?,??.0??,??.0??,??]tetracosan-7-ol
• IUPAC Traditional name: demissidine
• Synonyms: Solanine D; Demissidine; DEMISSIDINE

Database IDs

• CAS Number: 474-08-8
• EC Number: 207-478-1
• MDL Number: MFCD00200961
• PubChem SID: 162091809; 24893953
• PubChem CID: 101379

CALCULATED PROPERTIES

• Acid pKa: 18.296396
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.7868805
• LogD (pH = 7.4): 1.7991875
• Log P: 5.2881145
• Molar Refractivity: 120.0074 cm^3
• Polarizability: 48.258972 Å^3
• Polar Surface Area: 23.47 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: WF0192000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-40
• Safety Statements: 22-36
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H351
• GHS Precautionary statements: P281
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

DETAILS

MP Biomedicals - 02157541

(Solanine D)

Sigma Aldrich - D5649

Other Notes
Alkaloid found, as various glycosides, in the skin of unripe potatoes. Inhibits growth of human colon and liver cancer cells in culture, though less actively than its glycosides.1