(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-methylpropanoic acid

• ChemBase ID: 128711
• Molecular Formular: C44H68O13
• Molecular Mass: 805.00292
• Monoisotopic Mass: 804.46599224
• SMILES: O=C(O)C(O)(C)C[C@H]1O[C@]2(O[C@@H](CC(=C2)C)[C@@H](C=C[C@@H]2O[C@@]3(O[C@H]4[C@H](O)C(=C)[C@H](O[C@@H]4CC3)[C@@H](O)C[C@H](C)[C@H]3O[C@]4(OCCCC4)CC[C@H]3C)CC2)C)[C@H](O)CC1
• 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)CC(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)/t26-,27-,28+,30+,31+,32+,33-,34+,35-,36-,37+,38+,39-,41-,42+,43-,44-/m1/s1
• InChIKey: QNDVLZJODHBUFM-JGAYSDMHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (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-methylpropanoic acid
• IUPAC Traditional name: (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-methylpropanoic acid
• Synonyms: Okadaic acid; 9,10-Deepithio-9,10-didehydroacanthifolicin; Okadaic acid

Database IDs

• CAS Number: 78111-17-8
• MDL Number: MFCD00083455
• Beilstein Number: 4640246
• PubChem SID: 162223017
• PubChem CID: 57059112; 446512
• CHEBI ID: CHEBI:7733
• CHEMBL: 280487
• Chemspider ID: 393845
• KEGG ID: C01945
• MeSH Name: Okadaic Acid
• Wikipedia Title: Okadaic_acid

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

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; R
• 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: 2-8°C

Product Information

• Purity: ≥92% (HPLC)
• Empirical Formula (Hill Notation): C44H68O13

DETAILS

Sigma Aldrich - 75320

General description
Marine toxin, produced by dinoflagellates, accumulates in bivalves and sponges.
Other Notes
Tumour promoter and specific inhibitor of protein phosphatases 1 and 2A, review1