methyl (2R)-3-[(2S,5R,6R,8S)-8-[(2R)-4-[(2R,4'aR,5R,6'S,8'R,8'aS)-8'-hydroxy-6'-[(1S,3S)-1-hydroxy-3-[(2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]butyl]-7'-methylidene-hexahydro-3'H-spiro[oxolane-2,2'-pyrano[3,2-b]pyran]-5-yl]but-3-en-2-yl]-5-hydroxy-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl]-2-hydroxy-2-methylpropanoate

• ChemBase ID: 153540
• Molecular Formular: C45H70O13
• Molecular Mass: 819.0295
• Monoisotopic Mass: 818.4816423
• SMILES: C[C@@H]1CC[C@]2(CCCCO2)O[C@@H]1[C@@H](C)C[C@@H]([C@@H]1C(=C)[C@H]([C@H]2[C@H](O1)CC[C@]1(O2)CC[C@@H](O1)C=C[C@@H](C)[C@@H]1CC(=C[C@@]2(O1)[C@@H](CC[C@H](O2)CC(C)(C(=O)OC)O)O)C)O)O
• Canonical SMILES: COC(=O)C(C[C@@H]1CC[C@H]([C@]2(O1)O[C@@H](CC(=C2)C)[C@@H](C=C[C@H]1CC[C@]2(O1)CC[C@@H]1[C@@H](O2)[C@H](O)C(=C)[C@H](O1)[C@H](C[C@@H]([C@H]1O[C@@]2(CCCCO2)CC[C@H]1C)C)O)C)O)(O)C
• InChI: InChI=1S/C45H70O13/c1-26-22-35(56-45(24-26)36(47)13-12-32(55-45)25-42(6,50)41(49)51-7)27(2)10-11-31-15-19-44(54-31)20-16-34-40(58-44)37(48)30(5)39(53-34)33(46)23-29(4)38-28(3)14-18-43(57-38)17-8-9-21-52-43/h10-11,24,27-29,31-40,46-48,50H,5,8-9,12-23,25H2,1-4,6-7H3/t27-,28-,29+,31+,32+,33+,34-,35+,36-,37-,38+,39+,40-,42-,43+,44-,45-/m1/s1
• InChIKey: BVEXVMARIREFTJ-SPCHQZICSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2R)-3-[(2S,5R,6R,8S)-8-[(2R)-4-[(2R,4'aR,5R,6'S,8'R,8'aS)-8'-hydroxy-6'-[(1S,3S)-1-hydroxy-3-[(2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]butyl]-7'-methylidene-hexahydro-3'H-spiro[oxolane-2,2'-pyrano[3,2-b]pyran]-5-yl]but-3-en-2-yl]-5-hydroxy-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl]-2-hydroxy-2-methylpropanoate
• IUPAC Traditional name: methyl (2R)-3-[(2S,5R,6R,8S)-8-[(2R)-4-[(2R,4'aR,5R,6'S,8'R,8'aS)-8'-hydroxy-6'-[(1S,3S)-1-hydroxy-3-[(2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]butyl]-7'-methylidene-hexahydrospiro[oxolane-2,2'-pyrano[3,2-b]pyran]-5-yl]but-3-en-2-yl]-5-hydroxy-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl]-2-hydroxy-2-methylpropanoate
• Synonyms: Okadaic acid methyl ester

Database IDs

• CAS Number: 78111-14-5
• MDL Number: MFCD00171409
• PubChem SID: 162247679
• PubChem CID: 156939

CALCULATED PROPERTIES

• Acid pKa: 12.3764
• H Acceptors: 12
• H Donor: 4
• LogD (pH = 5.5): 5.28064
• LogD (pH = 7.4): 5.280636
• Log P: 5.28064
• Molar Refractivity: 215.5497 cm^3
• Polarizability: 85.96544 Å^3
• Polar Surface Area: 171.83 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-38
• Safety Statements: 26-36
• Storage Temperature: -20°C

Product Information

• Empirical Formula (Hill Notation): C45H70O13

DETAILS

Sigma Aldrich - O2507

Other Notes
Okadaic acid analog with very low affinity for OA receptors, and no apparent activity as a protein phosphatase inhibitor. However, it may be metabolized to OA, and so should be used with caution in whole-cell assays.