ChemFOnt: Showing chemical card for Okadaic acid (CFc000011654)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:59:29 UTC

Chemfont ID

CFc000011654

Molecule Identification

Common Name

Okadaic acid

Definition

Okadaic 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Okadaate	Generator
9,10-Deepithio-9,10-didehydroacanthifolicin	HMDB
PL Toxin II	HMDB
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-methylpropanoate	HMDB
Acid, ocadaic	HMDB
Acid, okadaic	HMDB
Ocadaic acid	HMDB
Okadaic acid	MeSH

Chemical Formula

C₄₄H₆₈O₁₃

Average Molecular Weight

805.0029

Monoisotopic Molecular Weight

804.465992262

IUPAC Name

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-methylpropanoic acid

Traditional Name

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-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 Number

78111-17-8

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 Key

QNDVLZJODHBUFM-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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Ketals

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 Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030441)
Cell membrane (HMDB: HMDB0030441)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030441)

Source

Exogenous

Exogenous (HMDB: HMDB0030441)

Food

Food (HMDB: HMDB0030441)

Aquatic origin

Mollusk

Mollusks (FooDB: FOOD00868)

Endogenous

Endogenous (HMDB: HMDB0030441)

Animal

Animal (HMDB: HMDB0030441)

Process

Not Available

Role

Indirect biological role

Marine biotoxin (HMDB: HMDB0030441)

Biological role

Modulator

Inhibitor

EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor (HMDB: HMDB0030441)

Calcium ionophore (HMDB: HMDB0030441)

Industrial application

Pharmaceutical industry

Antineoplastic agent

Antitumor (HMDB: HMDB0030441)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0044 g/L	ALOGPS
logP	2.73	ALOGPS
logP	5.13	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	3.76	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	182.83 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	210.78 m³·mol⁻¹	ChemAxon
Polarizability	88.49 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon