(2R)-3-[(2S,5R,6R,8S)-8-[(2R,3E)-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-methylpropanoic acid

• ChemBase ID: 134171
• Molecular Formular: C44H68O13
• Molecular Mass: 805.00292
• Monoisotopic Mass: 804.46599224
• 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)C[C@](C)(C(=O)O)O)O)C)O)O
• Canonical SMILES: CC1=C[C@]2(O[C@@H](C1)[C@@H](/C=C/[C@H]1CC[C@]3(O1)CC[C@@H]1[C@@H](O3)[C@H](O)C(=C)[C@H](O1)[C@H](C[C@@H]([C@H]1O[C@@]3(CCCCO3)CC[C@H]1C)C)O)C)O[C@@H](CC[C@H]2O)C[C@](C(=O)O)(O)C
• InChI: InChI=1S/C44H68O13/c1-25-21-34(55-44(23-25)35(46)12-11-31(54-44)24-41(6,50)40(48)49)26(2)9-10-30-14-18-43(53-30)19-15-33-39(57-43)36(47)29(5)38(52-33)32(45)22-28(4)37-27(3)13-17-42(56-37)16-7-8-20-51-42/h9-10,23,26-28,30-39,45-47,50H,5,7-8,11-22,24H2,1-4,6H3,(H,48,49)/b10-9+/t26-,27-,28+,30+,31+,32+,33-,34+,35-,36-,37+,38+,39-,41-,42+,43-,44-/m1/s1
• InChIKey: QNDVLZJODHBUFM-WFXQOWMNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-3-[(2S,5R,6R,8S)-8-[(2R,3E)-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-methylpropanoic acid
• IUPAC Traditional name: okadaic acid
• Synonyms: OA; Okadaic acid from Prorocentrum concavum

Database IDs

• CAS Number: 78111-17-8
• MDL Number: MFCD00083455
• PubChem SID: 24897998; 162228448; 24898069
• PubChem CID: 446512

CALCULATED PROPERTIES

• Acid pKa: 3.761946
• H Acceptors: 13
• H Donor: 5
• LogD (pH = 5.5): 3.3957899
• LogD (pH = 7.4): 1.855299
• Log P: 5.134746
• Molar Refractivity: 210.7806 cm^3
• Polarizability: 83.88593 Å^3
• Polar Surface Area: 182.83 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: ≥1 mg/mL; ethanol: ≥1 mg/mL; H2O: insoluble; methanol: ≥1 mg/mL
• Apperance: translucent film

Safety Information

• RTECS: AA8227800
• European Hazard Symbols: Toxic (T)
• UN Number: 3462
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1
• Risk Statements: 23/24/25-38
• Safety Statements: 26-36/37-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H315-H331
• GHS Precautionary statements: P261-P280-P301 + P310-P311
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 3462 6.1/PG 1
• Storage Temperature: -20°C

Product Information

• Purity: ≥90% (HPLC); 92-100% (HPLC)
• Shipped in: dry ice

DETAILS

Sigma Aldrich - O9381

Preparation Note
Isolated from unialgal cultures of dinoflagellates.
Biochem/physiol Actions
Dinoflagellate toxin and an ionophore-like polyether derivative of a 38 carbon, fatty acid. Readily enters cells. Inhibitor of type 1 and type 2A protein phosphatases. Does not inhibit tyrosine phosphatases, alkaline phosphatases or acid phosphatase. Known tumor promotor. Used to study various cellular processes including cell cycle, apoptosis, nitric oxide metabolism and calcium signaling.

Sigma Aldrich - O4511

Biochem/physiol Actions
Dinoflagellate toxin and an ionophore-like polyether derivative of a 38 carbon, fatty acid. Readily enters cells. Inhibitor of type 1 and type 2A protein phosphatases. Does not inhibit tyrosine phosphatases, alkaline phosphatases or acid phosphatase. Known tumor promotor. Used to study various cellular processes including cell cycle, apoptosis, nitric oxide metabolism and calcium signaling.