Natural Product (NP) Details

General Information of the NP (ID: NP6785)
Name
Brucine
Synonyms
BRUCINE; 357-57-3; 10,11-Dimethoxystrychnine; Brucinum; (-)-Brucine; l-Brucine; 2,3-Dimethoxystrychnine; 2,3-Dimethoxystrychnidin-10-one; 10,11-Dimethystrychnine; UNII-6NG17YCK6H; Brucina; Brucin; 6NG17YCK6H; Brucine alkaloid; CHEBI:3193; Dimethoxy strychnine; Bruzin; 2,3-Dimethoxy-strychnine; RCRA waste number P018; DSSTox_RID_77490; DSSTox_GSID_24662; Strychnine, 2,3-dimethoxy-; 145428-94-0; Brucin [German]; Brucina [Italian]; (4aR,4a1R,5aS,8aR,8a1S,15aS)-10,11-dimethoxy-2,4a,4a1,5,5a,7,8,8a1,15,15a-decahydro-14H-4,6-methanoindolo[3,2,1-ij]oxepino[2,3,4-de]pyrrolo[2,3-h]quinolin-14-one; CAS-357-57-3; SMR000112281; DSSTox_CID_4662; 10,11-dimethoxy strychnine; CCRIS 4754; HSDB 307; anhydrous brucine; Bisdesmethylbrucin; Brucine Anhydrous; UN 1570; NCGC00094861-01; (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]quinoline-14-one; EINECS 206-614-7; UN1570; PubChem7945; RCRA waste no. P018; Brucine, anhydrous, 98%; GTPL342; MLS000515808; MLS001424166; SCHEMBL113229; CHEMBL501756; MEGxp0_001865; DTXSID2024662; ACon1_001990; Brucine [UN1570] [Poison]; HMS2052O03; HMS2268L16; ZINC1069090; Tox21_111349; Tox21_302174; BDBM50401037; MFCD00005942; AKOS015955678; AKOS024282466; CCG-101078; MCULE-9524496694; NC00328; NSC 757797; NCGC00255253-01; NCGC00263445-02; NCGC00384497-01; M127; B0670; B0946; C09084; Brucine - CASMI2016 Category 1 - Challenge 9; Q411022; SR-01000712407; Q-100426; SR-01000712407-5; BRD-K68077509-001-01-6; Brucine, European Pharmacopoeia (EP) Reference Standard; (1R,11S,18S,20R,21R,22S)-4,5-dimethoxy-12-oxa-8,17-diazaheptacyclo[15.5.2.0^{1,18}.0^{2,7}.0^{8,22}.0^{11,21}.0^{15,20}]tetracosa-2(7),3,5,14-tetraen-9-one
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Species Origin Strchnos icaja ...     Click to Show/Hide
Strchnos icaja
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Gentianales
Family: Loganiaceae
Genus: Strychnos
Species: Strchnos icaja
Disease Hepatocellular carcinoma [ICD-11: 2C12] Investigative [1]
Structure
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2D MOL

3D MOL

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Formula
C23H26N2O4
PubChem CID
442021
Canonical SMILES
COC1=C(C=C2C(=C1)C34CCN5C3CC6C7C4N2C(=O)CC7OCC=C6C5)OC
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
CAS Number
CAS 357-57-3
ChEBI ID
CHEBI:3193
Herb ID
HBIN018923
SymMap ID
SMIT00180
TCMSP ID
MOL003435
TTD Drug ID
D0H2UT
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Gemcitabine      Solid tumour/cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression p105  Molecule Info 
Pathway MAP
                    In-vitro Model MCF-7 CVCL_0031 Invasive breast carcinoma Homo sapiens
                    Experimental
                    Result(s)		 Brucine, either individually or in combination, but not gemcitabine, inhibited NF-kB subunit (p65) expression in MCF-7 cells.
Target and Pathway
Target(s) Muscarinic acetylcholine receptor M3 (CHRM3)  Molecule Info  [3]
KEGG Pathway Calcium signaling pathway Click to Show/Hide
2 Neuroactive ligand-receptor interaction
3 Cholinergic synapse
4 Regulation of actin cytoskeleton
5 Insulin secretion
6 Salivary secretion
7 Gastric acid secretion
8 Pancreatic secretion
Panther Pathway Alzheimer disease-amyloid secretase pathway Click to Show/Hide
2 Heterotrimeric G-protein signaling pathway-Gq alpha and Go alpha mediated pathway
3 Muscarinic acetylcholine receptor 1 and 3 signaling pathway
Pathwhiz Pathway Gastric Acid Production Click to Show/Hide
Reactome Muscarinic acetylcholine receptors Click to Show/Hide
2 Acetylcholine regulates insulin secretion
3 G alpha (q) signalling events
WikiPathways Monoamine GPCRs Click to Show/Hide
2 Calcium Regulation in the Cardiac Cell
3 Regulation of Actin Cytoskeleton
4 GPCRs, Class A Rhodopsin-like
5 Gastrin-CREB signalling pathway via PKC and MAPK
6 Integration of energy metabolism
7 GPCR ligand binding
8 GPCR downstream signaling
9 GPCRs, Other
References
Reference 1 Antitumor effects of brucine immuno-nanoparticles on hepatocellular carcinoma in vivo. Oncol Lett. 2018 May;15(5):6137-6146.
Reference 2 Anticancer effects of brucine and gemcitabine combination in MCF-7 human breast cancer cells. Nat Prod Res. 2015;29(5):484-90.
Reference 3 Subtype-selective positive cooperative interactions between brucine analogues and acetylcholine at muscarinic receptors: radioligand binding studies. Mol Pharmacol. 1998 Mar;53(3):573-89.
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