Details of the Drug

General Information of Drug (ID: DM9B6Y1)

Drug Name
NORCANTHARIDIN
Synonyms
Norcantharidin; 5442/12/6; Endothall anhydride; Norcantharadine; 7-Oxabicyclo[221]heptane-2,3-dicarboxylic anhydride; 4,7-Epoxyisobenzofuran-1,3-dione, hexahydro-; 3,6-Endoxohexahydrophthalic anhydride; 29745-04-8; Hexahydro-4,7-epoxyisobenzofuran-1,3-dione; NSC 14003; 7-Oxabicyclo(221)heptane-2,3-dicarboxylic anhydride; FR-0742; 3,6-Endooxyphthalic anhydride, hexahydro-; Phthalic anhydride, hexahydro-3,6-endoxo-; C8H8O4; 4,10-dioxatricyclo[5210< 2,6> ]decane-3,5-dione; NSC 59023; BRN 0084287; DEMETHYL-CANTHARIDIN
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): 0 Molecular Weight (mw) 168.15
Logarithm of the Partition Coefficient (xlogp) -0.1
Rotatable Bond Count (rotbonds) 0
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 4
Chemical Identifiers
Formula
C8H8O4
IUPAC Name
4,10-dioxatricyclo[5.2.1.02,6]decane-3,5-dione
Canonical SMILES
C1CC2C3C(C1O2)C(=O)OC3=O
InChI
InChI=1S/C8H8O4/c9-7-5-3-1-2-4(11-3)6(5)8(10)12-7/h3-6H,1-2H2
InChIKey
JAABVEXCGCXWRR-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
93004
ChEBI ID
CHEMBL8327
CAS Number
5442-12-6
TTD ID
D0W4IL
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
PP2A B subunit isoform R5-alpha (PPP2R5A) TTLONKX 2A5A_HUMAN Inhibitor [2]
Serine/threonine PP1-alpha (PPP1CA) TTFLH0E PP1A_HUMAN Inhibitor [1]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Bcl-2 homologous antagonist/killer (BAK1) OTDP6ILW BAK_HUMAN Gene/Protein Processing [3]
Bcl-2-like protein 1 (BCL2L1) OTRC5K9O B2CL1_HUMAN Gene/Protein Processing [4]
Bcl-2-like protein 11 (BCL2L11) OTNQQWFJ B2L11_HUMAN Gene/Protein Processing [3]
Bcl2-associated agonist of cell death (BAD) OT63ERYM BAD_HUMAN Gene/Protein Processing [4]
BH3-interacting domain death agonist (BID) OTOSHSHU BID_HUMAN Gene/Protein Processing [3]
Cyclic AMP-dependent transcription factor ATF-4 (ATF4) OTRFV19J ATF4_HUMAN Gene/Protein Processing [5]
Cyclin-dependent kinase inhibitor 1 (CDKN1A) OTQWHCZE CDN1A_HUMAN Post-Translational Modifications [4]
DNA damage-inducible transcript 3 protein (DDIT3) OTI8YKKE DDIT3_HUMAN Gene/Protein Processing [5]
Eukaryotic translation initiation factor 2 subunit 1 (EIF2S1) OTM0GDTP IF2A_HUMAN Post-Translational Modifications [5]
Histone H2AX (H2AX) OT18UX57 H2AX_HUMAN Gene/Protein Processing [5]
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References

1 In silico identification and biochemical evaluation of novel inhibitors of NRH:quinone oxidoreductase 2 (NQO2). Bioorg Med Chem Lett. 2010 Dec 15;20(24):7331-6.
2 Structure-activity relationship of cantharidin derivatives to protein phosphatases 1, 2A1, and 2B, Bioorg. Med. Chem. Lett. 7(14):1833-1836 (1997).
3 Norcantharidin induce apoptosis in human nasopharyngeal carcinoma through caspase and mitochondrial pathway. Environ Toxicol. 2018 Mar;33(3):343-350. doi: 10.1002/tox.22521. Epub 2017 Nov 29.
4 Norcantharidin induces apoptosis of breast cancer cells: involvement of activities of mitogen activated protein kinases and signal transducers and activators of transcription. Toxicol In Vitro. 2011 Apr;25(3):699-707. doi: 10.1016/j.tiv.2011.01.011. Epub 2011 Jan 23.
5 Norcantharidin combined with paclitaxel induces endoplasmic reticulum stress mediated apoptotic effect in prostate cancer cells by targeting SIRT7 expression. Environ Toxicol. 2021 Nov;36(11):2206-2216. doi: 10.1002/tox.23334. Epub 2021 Jul 16.