Okadaic Acid

Details

• Internal ID: b7b44edd-127c-4247-a719-3b14e5b132f1
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Ethers > Acetals > Ketals
• IUPAC Name: (2R)-3-[(2S,6R,8S,11R)-2-[(E,2R)-4-[(2S,2'R,4R,4aS,6R,8aR)-4-hydroxy-2-[(1S,3S)-1-hydroxy-3-[(2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]butyl]-3-methylidenespiro[4a,7,8,8a-tetrahydro-4H-pyrano[3,2-b]pyran-6,5'-oxolane]-2'-yl]but-3-en-2-yl]-11-hydroxy-4-methyl-1,7-dioxaspiro[5.5]undec-4-en-8-yl]-2-hydroxy-2-methylpropanoic acid
• 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)/b10-9+/t26-,27-,28+,30+,31+,32+,33-,34+,35-,36-,37+,38+,39-,41-,42+,43-,44-/m1/s1
• InChI Key: QNDVLZJODHBUFM-WFXQOWMNSA-N
• Popularity: 7,454 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₄H₆₈O₁₃
• Molecular Weight: 805.00 g/mol
• Exact Mass: 804.46599222 g/mol
• Topological Polar Surface Area (TPSA): 183.00 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 5.21
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 10

Synonyms

• 78111-17-8
• 9,10-Deepithio-9,10-didehydroacanthifolicin
• CHEMBL280487
• CHEBI:44658
• (2R)-3-[(2S,5R,6R,8S)-8-[(2R,3E)-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
• OKA
• Acanthifolicin, 9,10-deepithio-9,10-didehydro-
• C44H68O13
• 1W21G5Q4N2
• NSC-677083
• Okadaic acid from Prorocentrum concavum
• 1jk7
• OKADAIC ACID [MI]
• Probes1_000180
• OKADAIC ACID [HSDB]
• 35-DEMETHYL-DTX 1
• SCHEMBL131485
• OA and NSC 677083
• CHEMBL158524
• GTPL5349
• DTXSID60880002
• 1u32
• HY-N6785
• 35-DEMETHYLDINOPHYSISTOXIN 1
• BDBM50097634
• BDBM50110676
• HB0468
• AKOS040742329
• AT32065
• DB02169
• CS-0014219
• Q414042
• Okadaic acid from Prorocentrum concavum, 92-100% (HPLC)
• Okadaic acid from Prorocentrum concavum, >=90% (HPLC), translucent film
• (.ALPHA.R,2S,5R,6R,8S)-.ALPHA.,5-DIHYDROXY-.ALPHA.,10-DIMETHYL-8-((1R,2E)-1-METHYL-3-((2R,4'AR,5R,6'S,8'R,8'AS)-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)-1,7-DIOXASPIRO(5.5)UNDEC-10-ENE-2-PROPANOIC ACID
• (2R)-2-hydroxy-3-[(2S,5R,6R,8S)-5-hydroxy-8-{(1R,2E)-3-[(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]-1-methylprop-2-en-1-yl}-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl]-2-methylpropanoic acid
• (2R)-3-((2S,6R,8S,11R)-2-((E,2R)-4-((2S,2'R,4R,4AS,6R,8AR)-4-HYDROXY-2-((1S,3S)-1-HYDROXY-3-((2S,3R,6S)-3-METHYL-1,7-DIOXASPIRO(5.5)UNDECAN-2-YL)BUTYL)-3-METHYLIDENESPIRO(4A,7,8,8A-TETRAHYDRO-4H-PYRANO(3,2-B)PYRAN-6,5'-OXOLANE)-2'-YL)BUT-3-EN-2-YL)-11-HYDROXY-4-METHYL-1,7-DIOXASPIRO(5.5)UNDEC-4-EN-8-YL)-2-HYDROXY-2-METHYLPROPANOIC ACID
• (2R)-3-[(2S,5R,6R,8S)-8-{(2R,3E)-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'-methylidenehexahydro-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
• 1,7-DIOXASPIRO(5.5)UNDEC-10-ENE-2-PROPANOIC ACID, .ALPHA.,5-DIHYDROXY-.ALPHA.,10-DIMETHYL-8-((1R,2E)-1-METHYL-3-((2R,4'AR,5R,6'S,8'R,8'AS)-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)-, (.ALPHA.R,2S,5R,6R,8S)-
• 1,7-Dioxaspiro[5.5]undec-10-ene-2-propanoic acid, .alpha,5-dihydroxy-.alpha.,10-dimethyl-8-[(1R,2E)-1-methyl-3-[(2R,4'aR,5R,6'S,8'R,8'aS)-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]-, (.alpha.R,2S,5R,6R,8S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9383	93.83%
Caco-2	-	0.8718	87.18%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7991	79.91%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8249	82.49%
OATP1B3 inhibitior	+	0.9161	91.61%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.9243	92.43%
P-glycoprotein inhibitior	+	0.7417	74.17%
P-glycoprotein substrate	+	0.7524	75.24%
CYP3A4 substrate	+	0.7364	73.64%
CYP2C9 substrate	-	0.8048	80.48%
CYP2D6 substrate	-	0.8654	86.54%
CYP3A4 inhibition	-	0.8160	81.60%
CYP2C9 inhibition	-	0.9020	90.20%
CYP2C19 inhibition	-	0.8976	89.76%
CYP2D6 inhibition	-	0.9508	95.08%
CYP1A2 inhibition	-	0.8688	86.88%
CYP2C8 inhibition	+	0.7779	77.79%
CYP inhibitory promiscuity	-	0.9621	96.21%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5290	52.90%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.9117	91.17%
Skin irritation	+	0.7724	77.24%
Skin corrosion	-	0.9351	93.51%
Ames mutagenesis	-	0.8700	87.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7224	72.24%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	+	0.6625	66.25%
skin sensitisation	-	0.8887	88.87%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.6250	62.50%
Acute Oral Toxicity (c)	I	0.5349	53.49%
Estrogen receptor binding	+	0.8341	83.41%
Androgen receptor binding	+	0.7316	73.16%
Thyroid receptor binding	-	0.5073	50.73%
Glucocorticoid receptor binding	+	0.6879	68.79%
Aromatase binding	+	0.6285	62.85%
PPAR gamma	+	0.7686	76.86%
Honey bee toxicity	-	0.6701	67.01%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9862	98.62%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293224	P10636	Microtubule-associated protein tau	89.1 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.95%	98.95%
CHEMBL230	P35354	Cyclooxygenase-2	97.34%	89.63%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.87%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.84%	97.25%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	95.84%	96.47%
CHEMBL3359	P21462	Formyl peptide receptor 1	94.97%	93.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.23%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	93.13%	96.61%
CHEMBL3401	O75469	Pregnane X receptor	92.32%	94.73%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	88.66%	96.95%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	87.42%	91.24%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	87.30%	98.75%
CHEMBL4227	P25090	Lipoxin A4 receptor	87.06%	100.00%
CHEMBL5028	O14672	ADAM10	86.65%	97.50%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	86.30%	90.24%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.22%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.64%	95.56%
CHEMBL4506	Q96EB6	NAD-dependent deacetylase sirtuin 1	85.42%	88.33%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.28%	90.71%
CHEMBL221	P23219	Cyclooxygenase-1	84.78%	90.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.65%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.66%	85.14%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.58%	93.03%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.63%	100.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.46%	100.00%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	81.30%	90.93%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.79%	93.04%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.58%	99.17%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 446512
• LOTUS: LTS0001343
• wikiData: Q414042