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
CHEBI:9516
CAS Number
67526-95-8
TTD ID
D02KGR
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

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-hydroxy-3-methylglutaryl-coenzyme A reductase (HMGCR) OTRT3F3U HMDH_HUMAN Gene/Protein Processing [3]
3-hydroxyacyl-CoA dehydrogenase type-2 (HSD17B10) OT7RJON4 HCD2_HUMAN Gene/Protein Processing [3]
3-hydroxyisobutyrate dehydrogenase, mitochondrial (HIBADH) OTCMMMIZ 3HIDH_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.