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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:36:48 UTC
Update Date2022-03-07 02:52:33 UTC
HMDB IDHMDB0030441
Secondary Accession Numbers
  • HMDB30441
Metabolite Identification
Common NameOkadaic acid
DescriptionOkadaic acid is found in mollusks. Okadaic acid is found in the marine sponges Halichondria okadai and Halichondria melanodocia and shellfish. It is a metabolite of Prorocentrum lima. It is a diarrhetic shellfish toxin. Okadaic acid is a toxin that accumulates in bivalves and causes diarrhetic shellfish poisoning. The molecular formula of okadaic acid, which is a derivative of a C38 fatty acid, is C44H68O13. The IUPAC name of okadaic acid is (2R)-2-hydroxy-3-{(2S,5R,6R,8S)-5-hydroxy-[(1R,2E)-3-((2R,5R,6'S,8'R,8a'S)-8'-hydroxy-6'-{(1S,3S)-1-hydroxy-3-[(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)-1-methylprop-2-en-1-yl]-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl}-2-methylpropanoic acid. Okadaic acid was named from the marine sponge Halichondria okadai, from which okadaic acid was isolated for the first time. It has also been isolated from another marine sponge, H. malanodocia, as a cytotoxin. The real producer of okadaic acid is a marine dinoflagellate
Structure
Data?1563861985
Synonyms
ValueSource
OkadaateGenerator
9,10-Deepithio-9,10-didehydroacanthifolicinHMDB
PL Toxin IIHMDB
2-Hydroxy-3-{5-hydroxy-8-[(3E)-4-[8'-hydroxy-6'-(1-hydroxy-3-{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]-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl}-2-methylpropanoateHMDB
Acid, ocadaicHMDB
Acid, okadaicHMDB
Ocadaic acidHMDB
Okadaic acidMeSH
Chemical FormulaC44H68O13
Average Molecular Weight805.0029
Monoisotopic Molecular Weight804.465992262
IUPAC Name2-hydroxy-3-{5-hydroxy-8-[(3E)-4-[8'-hydroxy-6'-(1-hydroxy-3-{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]-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl}-2-methylpropanoic acid
Traditional Name2-hydroxy-3-{5-hydroxy-8-[(3E)-4-[8'-hydroxy-6'-(1-hydroxy-3-{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]-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl}-2-methylpropanoic acid
CAS Registry Number78111-17-8
SMILES
CC(CC(O)C1OC2CCC3(CCC(O3)\C=C\C(C)C3CC(C)=CC4(OC(CC(C)(O)C(O)=O)CCC4O)O3)OC2C(O)C1=C)C1OC2(CCCCO2)CCC1C
InChI Identifier
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+
InChI KeyQNDVLZJODHBUFM-MDZDMXLPSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassEthers
Direct ParentKetals
Alternative Parents
Substituents
  • Ketal
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Oxane
  • Pyran
  • Tertiary alcohol
  • Tetrahydrofuran
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Dialkyl ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point164 - 166 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0044 g/LALOGPS
logP2.73ALOGPS
logP5.13ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)3.76ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area182.83 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity210.78 m³·mol⁻¹ChemAxon
Polarizability88.49 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+268.40630932474
DeepCCS[M-H]-266.58130932474
DeepCCS[M-2H]-299.82230932474
DeepCCS[M+Na]+274.01230932474
AllCCS[M+H]+272.232859911
AllCCS[M+H-H2O]+271.632859911
AllCCS[M+NH4]+272.732859911
AllCCS[M+Na]+272.932859911
AllCCS[M-H]-286.132859911
AllCCS[M+Na-2H]-293.232859911
AllCCS[M+HCOO]-301.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Okadaic acidCC(CC(O)C1OC2CCC3(CCC(O3)\C=C\C(C)C3CC(C)=CC4(OC(CC(C)(O)C(O)=O)CCC4O)O3)OC2C(O)C1=C)C1OC2(CCCCO2)CCC1C4577.5Standard polar33892256
Okadaic acidCC(CC(O)C1OC2CCC3(CCC(O3)\C=C\C(C)C3CC(C)=CC4(OC(CC(C)(O)C(O)=O)CCC4O)O3)OC2C(O)C1=C)C1OC2(CCCCO2)CCC1C4953.6Standard non polar33892256
Okadaic acidCC(CC(O)C1OC2CCC3(CCC(O3)\C=C\C(C)C3CC(C)=CC4(OC(CC(C)(O)C(O)=O)CCC4O)O3)OC2C(O)C1=C)C1OC2(CCCCO2)CCC1C5415.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Okadaic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Okadaic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Okadaic acid GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Okadaic acid GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Okadaic acid GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Okadaic acid 10V, Positive-QTOFsplash10-052u-6202012910-6a4e7089c2f900223a192016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Okadaic acid 20V, Positive-QTOFsplash10-052u-9112168800-6d0bf4b6d501addde97b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Okadaic acid 40V, Positive-QTOFsplash10-0pic-9212022100-6bc8f80d6aac5cf742562016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Okadaic acid 10V, Negative-QTOFsplash10-000i-9302010110-aeb2581b5f1840056f0c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Okadaic acid 20V, Negative-QTOFsplash10-000i-9017000500-f2952279f3ed70043dc92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Okadaic acid 40V, Negative-QTOFsplash10-0fft-9546110100-b7aa8c44534d446d8d842016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Okadaic acid 10V, Positive-QTOFsplash10-052r-0000000940-aeab3fb939aa872c1efe2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Okadaic acid 20V, Positive-QTOFsplash10-0550-2221318950-2e80f445457f8309718b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Okadaic acid 40V, Positive-QTOFsplash10-0zg1-9314741130-5d7a2011860509c7bdd22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Okadaic acid 10V, Negative-QTOFsplash10-0udi-0000000490-8ac6020070b8bb2cfe0f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Okadaic acid 20V, Negative-QTOFsplash10-0udi-1000012690-2c912d6a29b8ade97e7a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Okadaic acid 40V, Negative-QTOFsplash10-0udv-3191402440-9d778ac031975ee1c0ef2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002307
KNApSAcK IDC00039897
Chemspider ID4510235
KEGG Compound IDC01945
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOkadaic acid
METLIN IDNot Available
PubChem Compound5353844
PDB IDNot Available
ChEBI ID1137572
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Yatsunami J, Komori A, Ohta T, Suganuma M, Fujiki H: Hyperphosphorylation of retinoblastoma protein and p53 by okadaic acid, a tumor promoter. Cancer Res. 1993 Jan 15;53(2):239-41. [PubMed:8417815 ]
  2. Korhonen P, Kyrylenko S, Suuronen T, Salminen A: Changes in DNA binding pattern of transcription factor YY1 in neuronal degeneration. Neurosci Lett. 2005 Mar 29;377(2):121-4. Epub 2004 Dec 21. [PubMed:15740849 ]
  3. Di Bartolomeo S, Spinedi A: Potentiation of okadaic acid-induced ceramide elevation but not apoptosis by inhibition of glucosylceramide synthase in human neuroepithelioma cells. Biochem Pharmacol. 2001 Apr 1;61(7):851-6. [PubMed:11274971 ]
  4. Morimoto C, Kiyama A, Kameda K, Ninomiya H, Tsujita T, Okuda H: Mechanism of the stimulatory action of okadaic acid on lipolysis in rat fat cells. J Lipid Res. 2000 Feb;41(2):199-204. [PubMed:10681403 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Protein phosphatase that associates with over 200 regulatory proteins to form highly specific holoenzymes which dephosphorylate hundreds of biological targets. Protein phosphatase 1 (PP1) is essential for cell division, and participates in the regulation of glycogen metabolism, muscle contractility and protein synthesis. Dephosphorylates RPS6KB1. Involved in regulation of ionic conductances and long-term synaptic plasticity. May play an important role in dephosphorylating substrates such as the postsynaptic density-associated Ca(2+)/calmodulin dependent protein kinase II. Component of the PTW/PP1 phosphatase complex, which plays a role in the control of chromatin structure and cell cycle progression during the transition from mitosis into interphase.
Gene Name:
PPP1CC
Uniprot ID:
P36873
Molecular weight:
38517.92
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]