Details of the Drug

General Information of Drug (ID: DM50RUD)

Drug Name
brucine
Synonyms 10,11-dimethoxy strychnine
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL is unavailable 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 394.5
Logarithm of the Partition Coefficient (xlogp) 1
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 5
Chemical Identifiers
Formula
C23H26N2O4
IUPAC Name
(4aR,5aS,8aR,13aS,15aS,15bR)-10,11-dimethoxy-4a,5,5a,7,8,13a,15,15a,15b,16-decahydro-2H-4,6-methanoindolo[3,2,1-ij]oxepino[2,3,4-de]pyrrolo[2,3-h]quinolin-14-one
Canonical SMILES
COC1=C(C=C2C(=C1)[C@]34CCN5[C@H]3C[C@@H]6[C@@H]7[C@@H]4N2C(=O)C[C@@H]7OCC=C6C5)OC
InChI
InChI=1S/C23H26N2O4/c1-27-16-8-14-15(9-17(16)28-2)25-20(26)10-18-21-13-7-19-23(14,22(21)25)4-5-24(19)11-12(13)3-6-29-18/h3,8-9,13,18-19,21-22H,4-7,10-11H2,1-2H3/t13-,18-,19-,21-,22-,23+/m0/s1
InChIKey
RRKTZKIUPZVBMF-IBTVXLQLSA-N
Cross-matching ID
PubChem CID
442021
ChEBI ID
CHEBI:3193
CAS Number
357-57-3
TTD ID
D0H2UT

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Muscarinic acetylcholine receptor (CHRM) TTOXS3C NOUNIPROTAC Modulator (allosteric modulator) [2]
Muscarinic acetylcholine receptor M3 (CHRM3) TTQ13Z5 ACM3_HUMAN Modulator (allosteric modulator) [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
72 kDa type IV collagenase (MMP2) OT5NIWA2 MMP2_HUMAN Gene/Protein Processing [3]
Apoptosis regulator BAX (BAX) OTAW0V4V BAX_HUMAN Gene/Protein Processing [4]
Apoptosis regulator Bcl-2 (BCL2) OT9DVHC0 BCL2_HUMAN Gene/Protein Processing [4]
Caspase-3 (CASP3) OTIJRBE7 CASP3_HUMAN Gene/Protein Processing [5]
Caspase-9 (CASP9) OTD4RFFG CASP9_HUMAN Gene/Protein Processing [6]
Cathepsin D (CTSD) OTQZ36F3 CATD_HUMAN Gene/Protein Processing [3]
Fibronectin (FN1) OTB5ZN4Q FINC_HUMAN Gene/Protein Processing [3]
Muscarinic acetylcholine receptor M2 (CHRM2) OTUMZ2WR ACM2_HUMAN Protein Interaction/Cellular Processes [7]
Muscarinic acetylcholine receptor M3 (CHRM3) OTKSD095 ACM3_HUMAN Protein Interaction/Cellular Processes [7]
Muscarinic acetylcholine receptor M4 (CHRM4) OTF0F0FF ACM4_HUMAN Protein Interaction/Cellular Processes [8]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Discovery agent
ICD Disease Classification N.A.
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Muscarinic acetylcholine receptor M3 (CHRM3) DTT CHRM3 4.61E-07 -0.59 -0.73
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression 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: 342).
2 Subtype-selective positive cooperative interactions between brucine analogues and acetylcholine at muscarinic receptors: radioligand binding studies. Mol Pharmacol. 1998 Mar;53(3):573-89.
3 Brucine, an alkaloid from seeds of Strychnos nux-vomica Linn., represses hepatocellular carcinoma cell migration and metastasis: the role of hypoxia inducible factor 1 pathway. Toxicol Lett. 2013 Oct 24;222(2):91-101. doi: 10.1016/j.toxlet.2013.07.024. Epub 2013 Aug 7.
4 The apoptotic effect of brucine from the seed of Strychnos nux-vomica on human hepatoma cells is mediated via Bcl-2 and Ca2+ involved mitochondrial pathway. Toxicol Sci. 2006 May;91(1):59-69. doi: 10.1093/toxsci/kfj114. Epub 2006 Jan 27.
5 The cytotoxicity induced by brucine from the seed of Strychnos nux-vomica proceeds via apoptosis and is mediated by cyclooxygenase 2 and caspase 3 in SMMC 7221 cells. Food Chem Toxicol. 2007 Sep;45(9):1700-8.
6 Cytotoxic and antitumor effects of brucine on Ehrlich ascites tumor and human cancer cell line. Life Sci. 2011 Aug 1;89(5-6):147-58. doi: 10.1016/j.lfs.2011.05.020. Epub 2011 Jun 13.
7 Asparagine, valine, and threonine in the third extracellular loop of muscarinic receptor have essential roles in the positive cooperativity of strychnine-like allosteric modulators. J Pharmacol Exp Ther. 2005 May;313(2):688-96. doi: 10.1124/jpet.104.080358. Epub 2005 Jan 12.
8 Interaction studies of multiple binding sites on m4 muscarinic acetylcholine receptors. Mol Pharmacol. 2006 Aug;70(2):736-46. doi: 10.1124/mol.106.024711. Epub 2006 May 18.