Details of the Drug

General Information of Drug (ID: DMDMQIE)

Drug Name
THAPSIGARGIN
Synonyms
thapsigargin; 67526-95-8; UNII-Z96BQ26RZD; Z96BQ26RZD; CHEMBL96926; CHEBI:9516; OCTANOIC ACID [3S-[3ALPHA, 3ABETA, 4ALPHA, 6BETA, 6ABETA, 7BETA, 8ALPHA(Z), 9BALPHA]]-6-(ACETYLOXY)-2,3,-3A,4,5,6,6A,7,8,9B-DECAHYDRO-3,3A-DIHYDROXY-3,6,9-TRIMETHYL-8-[(2-METHYL-1-OXO-2-BUTENYL)OXY]-2-OXO-4-(1-OXOBUTOXY)-AZULENO[4,5-B]FURAN-7-YL ESTER
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 3 Molecular Weight (mw) 650.8
Logarithm of the Partition Coefficient (xlogp) 3.6
Rotatable Bond Count (rotbonds) 17
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 12
Chemical Identifiers
Formula
C34H50O12
IUPAC Name
[(3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-acetyloxy-4-butanoyloxy-3,3a-dihydroxy-3,6,9-trimethyl-8-[(Z)-2-methylbut-2-enoyl]oxy-2-oxo-4,5,6a,7,8,9b-hexahydroazuleno[4,5-b]furan-7-yl] octanoate
Canonical SMILES
CCCCCCCC(=O)O[C@H]1[C@H]2C(=C([C@@H]1OC(=O)/C(=C\\C)/C)C)[C@H]3[C@]([C@H](C[C@]2(C)OC(=O)C)OC(=O)CCC)([C@](C(=O)O3)(C)O)O
InChI
InChI=1S/C34H50O12/c1-9-12-13-14-15-17-24(37)43-28-26-25(20(5)27(28)44-30(38)19(4)11-3)29-34(41,33(8,40)31(39)45-29)22(42-23(36)16-10-2)18-32(26,7)46-21(6)35/h11,22,26-29,40-41H,9-10,12-18H2,1-8H3/b19-11-/t22-,26+,27-,28-,29-,32-,33+,34+/m0/s1
InChIKey
IXFPJGBNCFXKPI-FSIHEZPISA-N
Cross-matching ID
PubChem CID
446378
ChEBI ID
CHEMBL96926
CAS Number
67526-95-8
TTD ID
D02KGR
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
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Sarcoplasmic/endoplasmic reticulum calcium ATPase (ATP2A) TTZVSJ2 NOUNIPROTAC Inhibitor [1]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-2 (PLCG2) OTGVC9MY PLCG2_HUMAN Gene/Protein Processing [2]
10 kDa heat shock protein, mitochondrial (HSPE1) OT7JSZLB CH10_HUMAN Gene/Protein Processing [3]
14-3-3 protein epsilon OT3WQXNA 1433E_HUMAN Gene/Protein Processing [4]
14-3-3 protein eta OTP8NJFJ 1433F_HUMAN Gene/Protein Processing [3]
14-3-3 protein gamma OTYQTMPI 1433G_HUMAN Gene/Protein Processing [3]
2-amino-3-ketobutyrate coenzyme A ligase, mitochondrial (GCAT) OT6WZPWV KBL_HUMAN Gene/Protein Processing [3]
26S proteasome non-ATPase regulatory subunit 1 (PSMD1) OTW258OV PSMD1_HUMAN Gene/Protein Processing [3]
3-hydroxyisobutyrate dehydrogenase, mitochondrial (HIBADH) OTCMMMIZ 3HIDH_HUMAN Gene/Protein Processing [3]
5-hydroxytryptamine receptor 1A (HTR1A) OT38K9MK 5HT1A_HUMAN Gene/Protein Processing [5]
6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 3 (PFKFB3) OT25JBA3 F263_HUMAN Gene/Protein Processing [3]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Elucidation of the topography of the thapsigargin binding site in the sarco-endoplasmic calcium ATPase. Bioorg Med Chem. 2010 Aug 1;18(15):5634-46.
2 Chemical stresses fail to mimic the unfolded protein response resulting from luminal load with unfolded polypeptides. J Biol Chem. 2018 Apr 13;293(15):5600-5612.
3 Endoplasmic reticulum stress impairs insulin signaling through mitochondrial damage in SH-SY5Y cells. Neurosignals. 2012;20(4):265-80.
4 Proteomic signatures in thapsigargin-treated hepatoma cells. Chem Res Toxicol. 2011 Aug 15;24(8):1215-22. doi: 10.1021/tx200109y. Epub 2011 Jul 1.
5 Mechanisms of regulation of agonist efficacy at the 5-HT(1A) receptor by phospholipid-derived signaling components. J Pharmacol Exp Ther. 2001 Jun;297(3):1025-35.