ammonium (2R)-3-[(2S,5R,6R,8S)-8-[(2R,3E)-4-[(2R,5R,6'S,8'R,8'aS)-8'-hydroxy-6'-[(1S,3S)-1-hydroxy-3-[(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: 133125
• Molecular Formular: C44H71NO13
• Molecular Mass: 822.03344
• Monoisotopic Mass: 821.49254134
• SMILES: C[C@@H]1CC[C@]2(CCCCO2)OC1[C@@H](C)C[C@@H]([C@@H]1C(=C)[C@H]([C@H]2C(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.[NH4+]
• Canonical SMILES: CC1=C[C@]2(O[C@@H](C1)[C@@H](/C=C/[C@H]1CC[C@]3(O1)CCC1[C@@H](O3)[C@H](O)C(=C)[C@H](O1)[C@H](C[C@@H](C1O[C@@]3(CCCCO3)CC[C@H]1C)C)O)C)O[C@@H](CC[C@H]2O)C[C@](C(=O)[O-])(O)C.[NH4+]
• InChI: InChI=1S/C44H68O13.H3N/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);1H3/b10-9+;/t26-,27-,28+,30+,31+,32+,33?,34+,35-,36-,37?,38+,39-,41-,42+,43-,44-;/m1./s1
• InChIKey: ZBOMSHVRJSJGNR-JBNKPAQWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ammonium (2R)-3-[(2S,5R,6R,8S)-8-[(2R,3E)-4-[(2R,5R,6'S,8'R,8'aS)-8'-hydroxy-6'-[(1S,3S)-1-hydroxy-3-[(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: ammonium (2R)-3-[(2S,5R,6R,8S)-8-[(2R,3E)-4-[(2R,5R,6'S,8'R,8'aS)-8'-hydroxy-6'-[(1S,3S)-1-hydroxy-3-[(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: OA; Okadaic acid ammonium salt from Prorocentrum concavum

Database IDs

• CAS Number: 155716-06-6
• MDL Number: MFCD00153856
• PubChem SID: 162227402; 24898053
• PubChem CID: 16219809

CALCULATED PROPERTIES

• Acid pKa: 3.761946
• H Acceptors: 13
• H Donor: 4
• LogD (pH = 5.5): 3.3957899
• LogD (pH = 7.4): 1.855299
• Log P: 5.134746
• Molar Refractivity: 221.6177 cm^3
• Polarizability: 83.77306 Å^3
• Polar Surface Area: 185.66 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: soluble; ethanol: soluble; H2O: soluble0.1 mg/mL
• Apperance: white solid

Safety Information

• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 23/24/25-38
• Safety Statements: 22-26-36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H315-H331
• GHS Precautionary statements: P261-P280-P301 + P310-P311
• Storage Temperature: -20°C

Product Information

• Purity: ≥90% (HPLC)

DETAILS

Sigma Aldrich - O8010

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.