Natural Product (NP) Details

General Information of the NP (ID: NP6300)
Name
Sinomenine
Synonyms
Sinomenine; 115-53-7; Cucoline; Kukoline; Coculine; Sabianine A; CCRIS 1550; UNII-63LT81K70N; CHEBI:9163; CHEMBL248095; 63LT81K70N; morphinan-6-one, 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-, (9alpha,13alpha,14alpha)-; SR-05000002170; EINECS 204-094-6; BRN 0095280; Sinomenine,(S); Sinomenine (Cucoline); (9alpha,13alpha,14alpha)-4-Hydroxy-3,7-dimethoxy-17-methyl-7,8-didehydromorphinan-6-one hydrochloride; Spectrum2_001242; Spectrum3_001134; Spectrum4_001981; Spectrum5_001621; UPCMLD-DP085; 7,8-Didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-9-alpha,13-alpha,14-alpha-morphinan-6-one; BSPBio_002627; KBioGR_002508; 5-21-13-00516 (Beilstein Handbook Reference); SCHEMBL363812; SPECTRUM1505253; SPBio_001144; 4-Hydroxy-3,7-dimethoxy-17-methyl-7,8-didehydromorphinan-6-one; NP51; UPCMLD-DP085:001; BCBcMAP01_000195; KBio3_002127; DTXSID00871595; BDBM224031; ALBB-020908; BCP20032; ZINC1280591; BDBM50241298; CCG-39100; NSC785175; s2359; AKOS000265568; AKOS015960539; AKOS016023715; AC-8025; NSC-785175; 9-alpha,13-alpha,14-alpha-Morphinan-6-one, 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-; SMP1_000273; NCGC00161641-01; NCGC00161641-02; NCGC00161641-04; NCGC00161641-05; HY-15122; O600; Sinomenine 100 microg/mL in Acetonitrile; CS-0003778; SW219295-1; C09643; 115S537; Sinomenine, 0.3 mol chloroform of crystallization; Q7524904; SR-05000002170-2; SR-05000002170-3; BRD-K83459933-001-02-1; 3-(4-Fluorophenyl)-3-(toluene-4-sulfonylamino)-propionicacid; 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methylmorphinan-6-one; morphinan-6-one, 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-, (9alpha,13alpha,14alpha)-, hydrochloride
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Species Origin Sinomenium ...     Click to Show/Hide
Sinomenium
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Ranunculales
Family: Menispermaceae
Genus: Sinomenium
Disease Rheumatoid arthritis [ICD-11: FA20] Discontinued in Phase 2 [1]
Structure
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2D MOL

3D MOL

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Formula
C19H23NO4
PubChem CID
5459308
Canonical SMILES
CN1CCC23CC(=O)C(=CC2C1CC4=C3C(=C(C=C4)OC)O)OC
InChI
1S/C19H23NO4/c1-20-7-6-19-10-14(21)16(24-3)9-12(19)13(20)8-11-4-5-15(23-2)18(22)17(11)19/h4-5,9,12-13,22H,6-8,10H2,1-3H3/t12-,13+,19-/m1/s1
InChIKey
INYYVPJSBIVGPH-QHRIQVFBSA-N
CAS Number
CAS 115-53-7
ChEBI ID
CHEBI:9163
Herb ID
HBIN044111
SymMap ID
SMIT01618
TCMSP ID
MOL000625
TTD Drug ID
D0F9WF
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Methotrexate      Leukaemia     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 IL6  Molecule Info 
Pathway MAP
Down-regulation Expression MMP-9  Molecule Info 
Pathway MAP
                    In-vivo Model Arthritis was induced by immunizing with CII in female Srague-Dawley rats.
                    Experimental
                    Result(s)		 SIN and MTX have additive effects, decreasing inflammation and joint damage in CIA rats by modulating osteoclast-related cytokines. These results are indicative of the combined effect of SIN and MTX for anti-arthritic treatment in RA.
Target and Pathway
Target(s) NADPH oxidase (NOX)  Molecule Info  [3]
KEGG Pathway HIF-1 signaling pathway Click to Show/Hide
2 Phagosome
3 Osteoclast differentiation
4 Leukocyte transendothelial migration
Pathway Interaction Database RAC1 signaling pathway Click to Show/Hide
WikiPathways Vitamin D Receptor Pathway Click to Show/Hide
2 TNF alpha Signaling Pathway
References
Reference 1 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800008290)
Reference 2 A combination of sinomenine and methotrexate reduces joint damage of collagen induced arthritis in rats by modulating osteoclast-related cytokines. Int Immunopharmacol. 2014 Jan;18(1):135-41.
Reference 3 Sinomenine, a natural dextrorotatory morphinan analog, is anti-inflammatory and neuroprotective through inhibition of microglial NADPH oxidase. J Neuroinflammation. 2007 Sep 19;4:23.
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