Details of the Drug

General Information of Drug (ID: DM47CO1)

Drug Name

Okadaic acid

Synonyms

78111-17-8; CHEMBL280487; CHEBI:44658; C44H68O13; 9,10-Deepithio-9,10-didehydroacanthifolicin; Ocadaic Acid; OKA; (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; UNII-1W21G5Q4N2; CCRIS 3329; HSDB 7243; 1W21G5Q4N2; 1jk7

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 2

Molecular Weight (mw)

805

Logarithm of the Partition Coefficient (xlogp)

3.4

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C44H68O13
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
Canonical SMILES: C[C@@H]1CC[C@]2(CCCCO2)O[C@@H]1[C@@H](C)C[C@@H]([C@@H]3C(=C)[C@H]([C@H]4[C@H](O3)CC[C@]5(O4)CC[C@@H](O5)/C=C/[C@@H](C)[C@@H]6CC(=C[C@@]7(O6)[C@@H](CC[C@H](O7)C[C@](C)(C(=O)O)O)O)C)O)O
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
InChIKey: QNDVLZJODHBUFM-WFXQOWMNSA-N

Cross-matching ID

PubChem CID: 446512
ChEBI ID: CHEBI:44658
CAS Number: 78111-17-8
DrugBank ID: DB02169
TTD ID: D01SLG
VARIDT ID: DR01345

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Dual specificity protein phosphatase 1 (DUSP1)	TTG8HIM	DUS1_HUMAN	Inhibitor	[2]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
P-glycoprotein 1 (ABCB1)	DTUGYRD	MDR1_HUMAN	Substrate	[3]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMGCR)	OTRT3F3U	HMDH_HUMAN	Gene/Protein Processing	[4]
ADP/ATP translocase 1 (SLC25A4)	OTKYLK2J	ADT1_HUMAN	Gene/Protein Processing	[5]
Anaphase-promoting complex subunit 13 (ANAPC13)	OTQWXHEJ	APC13_HUMAN	Gene/Protein Processing	[6]
Apoptosis regulator BAX (BAX)	OTAW0V4V	BAX_HUMAN	Gene/Protein Processing	[7]
Apoptosis regulator Bcl-2 (BCL2)	OT9DVHC0	BCL2_HUMAN	Gene/Protein Processing	[8]
Apoptotic protease-activating factor 1 (APAF1)	OTJWIVY0	APAF_HUMAN	Gene/Protein Processing	[8]
Aryl hydrocarbon receptor nuclear translocator (ARNT)	OTMSIEZY	ARNT_HUMAN	Gene/Protein Processing	[4]
Ataxin-3 (ATXN3)	OTJVVGKT	ATX3_HUMAN	Gene/Protein Processing	[4]
ATP synthase subunit alpha, mitochondrial (ATP5F1A)	OT3FZDLX	ATPA_HUMAN	Gene/Protein Processing	[9]
ATP synthase subunit delta, mitochondrial (ATP5F1D)	OTXTAG2V	ATPD_HUMAN	Gene/Protein Processing	[9]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 5349).
2	Inhibition of protein phosphatase 1 stimulates secretion of Alzheimer amyloid precursor protein. Mol Med. 1995 Jul;1(5):535-41.
3	Fingerprint-based in silico models for the prediction of P-glycoprotein substrates and inhibitors. Bioorg Med Chem. 2012 Sep 15;20(18):5388-95.
4	Whole genome mRNA transcriptomics analysis reveals different modes of action of the diarrheic shellfish poisons okadaic acid and dinophysis toxin-1 versus azaspiracid-1 in Caco-2 cells. Toxicol In Vitro. 2018 Feb;46:102-112.
5	Alterations in metabolism-related genes induced in SHSY5Y cells by okadaic acid exposure. J Toxicol Environ Health A. 2012;75(13-15):844-56. doi: 10.1080/15287394.2012.690703.
6	The marine toxin okadaic acid induces alterations in the expression level of cancer-related genes in human neuronal cells. Ecotoxicol Environ Saf. 2013 Jun;92:303-11. doi: 10.1016/j.ecoenv.2013.03.009. Epub 2013 Apr 3.
7	Morphological and biochemical changes associated with apoptosis induced by okadaic acid in human amniotic FL cells. Environ Toxicol. 2009 Oct;24(5):437-45. doi: 10.1002/tox.20446.
8	Comparison of long-term versus short-term effects of okadaic acid on the apoptotic status of human HepaRG cells. Chem Biol Interact. 2020 Feb 1;317:108937. doi: 10.1016/j.cbi.2020.108937. Epub 2020 Jan 8.
9	Proteomic analysis reveals multiple patterns of response in cells exposed to a toxin mixture. Chem Res Toxicol. 2009 Jun;22(6):1077-85.