(2R,3R,4R,5R,6S)-2-{[(2R,3R,4R,5R,6S)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-{[(7S,10R,14S)-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.02,11.05,10.015,23.017,22]tetracos-4-en-7-yl]oxy}oxan-3-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl]oxy}-6-methyloxane-3,4,5-triol

• ChemBase ID: 156323
• Molecular Formular: C45H73NO14
• Molecular Mass: 852.05942
• Monoisotopic Mass: 851.50310602
• SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)O[C@@H]1[C@@H]([C@H]([C@@H](O[C@@H]1O[C@@H]1[C@H](O[C@H]([C@@H]([C@H]1O)O)O[C@H]1CC[C@@]2(C3CC[C@]4(C(C3CC=C2C1)CC1C4C(C2N1CC(CC2)C)C)C)C)CO)C)O)O)O)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](O[C@H]2CC[C@]3(C(=CCC4C3CC[C@]3(C4CC4C3C(C)C3N4CC(CC3)C)C)C2)C)[C@@H]([C@H]([C@@H]1O[C@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O[C@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O)O)O)O
• InChI: InChI=1S/C45H73NO14/c1-19-7-10-28-20(2)31-29(46(28)17-19)16-27-25-9-8-23-15-24(11-13-44(23,5)26(25)12-14-45(27,31)6)57-42-38(54)36(52)39(30(18-47)58-42)59-43-40(35(51)33(49)22(4)56-43)60-41-37(53)34(50)32(48)21(3)55-41/h8,19-22,24-43,47-54H,7,9-18H2,1-6H3/t19?,20?,21-,22-,24-,25?,26?,27?,28?,29?,30+,31?,32-,33-,34+,35+,36+,37+,38+,39+,40+,41+,42+,43+,44-,45-/m0/s1
• InChIKey: PDVHHANEJCMMRM-CXRPJEJSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5R,6S)-2-{[(2R,3R,4R,5R,6S)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-{[(7S,10R,14S)-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]tetracos-4-en-7-yl]oxy}oxan-3-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl]oxy}-6-methyloxane-3,4,5-triol
• IUPAC Traditional name: (2R,3R,4R,5R,6S)-2-{[(2R,3R,4R,5R,6S)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-{[(7S,10R,14S)-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]tetracos-4-en-7-yl]oxy}oxan-3-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl]oxy}-6-methyloxane-3,4,5-triol
• Synonyms: α-Chaconine

Database IDs

• CAS Number: 20562-03-2
• MDL Number: MFCD00017576
• Beilstein Number: 77396
• PubChem SID: 24853446; 162250461
• PubChem CID: 16211605

CALCULATED PROPERTIES

• Acid pKa: 11.783853
• H Acceptors: 15
• H Donor: 8
• LogD (pH = 5.5): -1.8373936
• LogD (pH = 7.4): -1.8256749
• Log P: 0.60955405
• Molar Refractivity: 215.0099 cm^3
• Polarizability: 87.61346 Å^3
• Polar Surface Area: 220.46 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: pyridine: soluble10 mg/mL, clear, very faintly yellow
• Melting Point: 228-236 °C

Safety Information

• RTECS: FL6700000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 63
• Safety Statements: 22-36/37
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H361
• 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
• Storage Temperature: -20°C

Product Information

• Purity: ≥98.0% (HPLC)
• Biological Source: from potato sprouts
• Empirical Formula (Hill Notation): C45H73NO14

DETAILS

Sigma Aldrich - 22455

Other Notes
Stimulates hepatic ornithine decarboxylase activity in rats1