ChemSpider 2D Image | Okadaic acid | C44H68O13

Okadaic acid

  • Molecular FormulaC44H68O13
  • Average mass805.003 Da
  • Monoisotopic mass804.466003 Da
  • ChemSpider ID393845

  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 17 of 17 defined stereocentres

More details:

Featured data source
The Merck Index Online

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

(2R)-2-Hydroxy-3-[(2S,5R,6R,8S)-5-hydroxy-8-{(2R,3E)-4-[(2R,4a'R,5R,6'S,8'R,8a'S)-8'-hydroxy-6'-{(1S,3S)-1-hydroxy-3-[(2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undec-2-yl]butyl}-7'-methyleneoctahydro-3H, 3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl]-3-buten-2-yl}-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl]-2-methylpropanoic acid [ACD/IUPAC Name]
(2R)-2-hydroxy-3-[(2S,5R,6R,8S)-5-hydroxy-8-{(2R,3E)-4-[(2R,4a'R,5R,6'S,8'R,8a'S)-8'-hydroxy-6'-{(1S,3S)-1-hydroxy-3-[(2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undec-2-yl]butyl}-7'-methylideneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl]but-3-en-2-yl}-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl]-2-methylpropanoic acid
1,7-Dioxaspiro[5.5]undec-10-ene-2-propanoic acid, α,5-dihydroxy-α,10-dimethyl-8-[(1R,2E)-1-methyl-3-[(2R,4a'R,5R,6'S,8'R,8a'S)-octahydro-8'-hydroxy-6'-[(1S,3S)-1-hydroxy-3-[(2S,3R,6S)-3-methyl -1,7-dioxaspiro[5.5]undec-2-yl]butyl]-7'-methylenespiro[furan-2(3H),2'(3'H)-pyrano[3,2-b]pyran]-5-yl]-2-propen-1-yl]-, (αR,2S,5R,6R,8S)- [ACD/Index Name]
1,7-Dioxaspiro[5.5]undec-10-ene-2-propanoic acid, α,5-dihydroxy-α,10-dimethyl-8-[(1R,2E)-1-methyl-3-[(2R,4a'R,5R,6'S,8'R,8a'S)-octahydro-8'-hydroxy-6'-[(1S,3S)-1-hydroxy-3-[(2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undec-2-yl]butyl]-7'-methylenespiro[furan-2(3H),2'(3'H)-pyrano[3,2-b]pyran]-5-yl]-2-propen-1-yl]-, (αR,2S,5R,6R,8S)-
1W21G5Q4N2
78111-17-8 [RN]
AA8227800
Halochondrine A
MFCD00083455
Okadaic acid [Wiki]
More...

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

4640246; 4900372; 5471989 [DBID]
CCRIS 3329 [DBID]
CHEBI:7733 [DBID]
LI7 [DBID]
O4511_SIGMA [DBID]
O9381_SIGMA [DBID]
  • Miscellaneous

    • Chemical Class:

      A polycyclic ether that is produced by several species of dinoflagellates, and is known to accumulate in both marine sponges and shellfish. A polyketide, polyether derivative of a C<smallsub>38</smal lsub> fatty acid, it is one of the primary causes of diarrhetic shellfish poisoning (DSP). It is a potent inhibitor of specific protein phosphatases and is known to have a variety of negative effects on cells. ChEBI CHEBI:44658
      A polycyclic ether that is produced by several species of dinoflagellates, and is known to accumulate in both marine sponges and shellfish. A polyketide, polyether derivative of a C38 fatty acid, it is one of the primary causes of diarrhetic shellfish poisoning (DSP). It is a potent inhibitor of specific protein phosphatases and is known to have a variety of negative effects on cells. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:44658

    • Bio Activity:

      Biochemicals & small molecules/Antagonists & inhibitors Hello Bio HB0468
      Enzymes/Phosphatase/Phosphoprotein phosphatase/PP2A Hello Bio HB0468
      Potent and non-competitive protein phosphatase inhibitor. Exhibits higher selectivity for PP2A and PP1 over PCM (purified polycation-modulated) phosphatase and PP2B (ID<sub>50</sub> values are 1.2, 315, 205 and 4530 nM respectively) yet little or no activity at PP2C. Displays apoptosis inducing properties with neurotoxic and tumor promoting effects. A diarrheic shellfish poisoning (DSP) toxin. Hello Bio HB0468
      Potent, non-competitive protein phosphatase inhibitor Hello Bio HB0468

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.3±0.1 g/cm3
Boiling Point: 921.6±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.6 mmHg at 25°C
Enthalpy of Vaporization: 152.1±6.0 kJ/mol
Flash Point: 269.4±27.8 °C
Index of Refraction: 1.585
Molar Refractivity: 210.4±0.4 cm3
#H bond acceptors: 13
#H bond donors: 5
#Freely Rotating Bonds: 10
#Rule of 5 Violations: 3
ACD/LogP: 4.21
ACD/LogD (pH 5.5): 2.72
ACD/BCF (pH 5.5): 21.84
ACD/KOC (pH 5.5): 81.91
ACD/LogD (pH 7.4): 1.24
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 2.71
Polar Surface Area: 183 Å2
Polarizability: 83.4±0.5 10-24cm3
Surface Tension: 58.3±5.0 dyne/cm
Molar Volume: 627.8±5.0 cm3

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