(5S)-7,11,16-trihydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)-5-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.02,7.011,15]heptadecane-2-carbaldehyde

• ChemBase ID: 155194
• Molecular Formular: C29H42O11
• Molecular Mass: 566.63718
• Monoisotopic Mass: 566.27271216
• SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]1CCC2(C3CC(C4(C(CCC4(C3CCC2(C1)O)O)C1=CC(=O)OC1)C)O)C=O)O)O)O
• Canonical SMILES: O=CC12CC[C@@H](CC2(O)CCC2C1CC(O)C1(C2(O)CCC1C1=CC(=O)OC1)C)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C29H42O11/c1-14-22(33)23(34)24(35)25(39-14)40-16-3-6-27(13-30)19-10-20(31)26(2)17(15-9-21(32)38-12-15)5-8-29(26,37)18(19)4-7-28(27,36)11-16/h9,13-14,16-20,22-25,31,33-37H,3-8,10-12H2,1-2H3/t14-,16-,17?,18?,19?,20?,22-,23+,24+,25-,26?,27?,28?,29?/m0/s1
• InChIKey: MFIXZHBJWSBQJA-MIBBATSYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5S)-7,11,16-trihydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)-5-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecane-2-carbaldehyde
• IUPAC Traditional name: (5S)-7,11,16-trihydroxy-15-methyl-14-(5-oxo-2H-furan-3-yl)-5-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecane-2-carbaldehyde
• Synonyms: 3β,5α,14-Trihydroxy-19-oxo-5β,20(22)-cardenolide 3-(6-deoxy-α-L-mannopyranoside); Strophanthidin α-L-rhamnopyranoside; Convallatoxin

Database IDs

• CAS Number: 508-75-8
• EC Number: 208-086-3
• MDL Number: MFCD00069477
• PubChem SID: 162249332; 24893136
• PubChem CID: 16219181

CALCULATED PROPERTIES

• Acid pKa: 7.1511126
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -1.0959796
• LogD (pH = 7.4): -1.5285846
• Log P: -1.0863996
• Molar Refractivity: 138.302 cm^3
• Polarizability: 55.681087 Å^3
• Polar Surface Area: 183.21 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: GL4025000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥65%
• Empirical Formula (Hill Notation): C29H42O10

DETAILS

Sigma Aldrich - C9140

Biochem/physiol Actions
A cardiac glycoside found in lily-of-the-valley with digitalis-like cardiac effects.1