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]
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) 10
Hydrogen Bond Donor Count (hbonddonor) 5
Hydrogen Bond Acceptor Count (hbondacc) 13
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
CHEMBL280487
CAS Number
78111-17-8
UNII
1W21G5Q4N2
DrugBank ID
DB02169
TTD ID
D01SLG
VARIDT ID
DR01345
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

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]

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

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
ADP/ATP translocase 1 (SLC25A4) OTKYLK2J ADT1_HUMAN Gene/Protein Processing [4]
Anaphase-promoting complex subunit 13 (ANAPC13) OTQWXHEJ APC13_HUMAN Gene/Protein Processing [5]
Apoptotic protease-activating factor 1 (APAF1) OTJWIVY0 APAF_HUMAN Gene/Protein Processing [6]
Aryl hydrocarbon receptor nuclear translocator (ARNT) OTMSIEZY ARNT_HUMAN Gene/Protein Processing [7]
Ataxin-3 (ATXN3) OTJVVGKT ATX3_HUMAN Gene/Protein Processing [7]
ATP synthase subunit alpha, mitochondrial (ATP5F1A) OT3FZDLX ATPA_HUMAN Gene/Protein Processing [8]
ATP synthase subunit delta, mitochondrial (ATP5F1D) OTXTAG2V ATPD_HUMAN Gene/Protein Processing [8]
ATP-binding cassette sub-family C member 3 (ABCC3) OTC3IJV4 MRP3_HUMAN Gene/Protein Processing [6]
ATP-dependent RNA helicase DDX1 (DDX1) OT3U8FD0 DDX1_HUMAN Gene/Protein Processing [7]
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Gene/Protein Processing [6]
Molecular Interaction Atlas (MIA) 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 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.
5 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.
6 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.
7 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.
8 Proteomic analysis reveals multiple patterns of response in cells exposed to a toxin mixture. Chem Res Toxicol. 2009 Jun;22(6):1077-85.