methyl (2S,3R,4S)-3-ethenyl-4-(2-oxoethyl)-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate

• ChemBase ID: 129426
• Molecular Formular: C17H24O10
• Molecular Mass: 388.36646
• Monoisotopic Mass: 388.13694697
• SMILES: COC(=O)C1=CO[C@H]([C@@H]([C@@H]1CC=O)C=C)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
• Canonical SMILES: O=CC[C@H]1[C@@H](C=C)[C@@H](OC=C1C(=O)OC)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
• InChI: InChI=1S/C17H24O10/c1-3-8-9(4-5-18)10(15(23)24-2)7-25-16(8)27-17-14(22)13(21)12(20)11(6-19)26-17/h3,5,7-9,11-14,16-17,19-22H,1,4,6H2,2H3/t8-,9+,11-,12-,13+,14-,16+,17+/m1/s1
• InChIKey: CSKKDSFETGLMSB-NRZPKYKESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3R,4S)-3-ethenyl-4-(2-oxoethyl)-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate
• IUPAC Traditional name: (-)-secologanin
• Synonyms: Secologanin; Secologanin; 开联番木鳖苷

Database IDs

• CAS Number: 19351-63-4
• MDL Number: MFCD16661163
• PubChem SID: 162223720; 24873401
• PubChem CID: 161276
• Chemspider ID: 141670
• Wikipedia Title: Secologanin

CALCULATED PROPERTIES

• Acid pKa: 12.027821
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -1.6899513
• LogD (pH = 7.4): -1.6899614
• Log P: -1.6899512
• Molar Refractivity: 88.5206 cm^3
• Polarizability: 35.786114 Å^3
• Polar Surface Area: 151.98 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 595.5°C
• Density: 1.42 g/mL

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥88% (HPLC)
• Grade: analytical standard
• Empirical Formula (Hill Notation): C17H24O10