Natural Product (NP) Details

General Information of the NP (ID: NP3882)
Name
L-canavanine
Synonyms
canavanine; L-canavanine; Canavanin; 543-38-4; 2-Amino-4-(guanidinooxy)butyric acid; UNII-3HZV514J4B; O-((Aminoiminomethyl)amino)-L-homoserine; O-((Aminoiminomethyl)amino)homoserine; 3HZV514J4B; CHEMBL443732; CHEBI:609827; GGB; L-2-AMINO-4-(GUANIDINOOXY)BUTYRIC ACID; C5H12N4O3; HSDB 3471; L(+)-Canavanine; Spectrum_001137; Tocris-0673; AI3-52153; L-Homoserine, O-((aminoiminomethyl)amino)-; Prestwick3_000609; Spectrum2_000800; Spectrum3_001206; Spectrum4_000783; Spectrum5_001884; Lopac-C-9758; bmse000073; Lopac0_000320; BSPBio_000518; BSPBio_002592; KBioGR_001226; KBioSS_001617; DivK1c_000360; O-carbamimidamido-L-homoserine; SCHEMBL151097; SPECTRUM1500833; SPBio_000940; BPBio1_000570; DTXSID5045041; HMS501B22; KBio1_000360; KBio2_001617; KBio2_004185; KBio2_006753; KBio3_002092; NINDS_000360; HMS1921K08; ZINC3869452; BDBM50271982; BDBM50370459; CCG-40178; AKOS006240676; DB01833; SDCCGMLS-0066683.P001; SDCCGSBI-0050308.P003; IDI1_000360; SMP1_000062; NCGC00015287-01; NCGC00015287-18; NCGC00015287-19; NCGC00024722-01; NCGC00024722-02; NCGC00024722-03; NCGC00024722-04; (2S)-2-amino-4-guanidinooxy-butanoic acid; (S)-2-Amino-4-(guanidinooxy)butanoic acid; O-{[Amino(imino)methyl]amino}-L-homoserine; X6876; Butyric acid, 2-amino-4-(guanidinooxy)-, L; C00308; (2S)-2-amino-4-(carbamimidamidooxy)butanoic acid; L-Alpha-amino-gamma-[guanidinooxy]-N-butyric acid; Q418408; L-Homoserine, O-((aminoiminomethyl)amino)- (9CI); [Eur.J.Pharmacol. 269:269; 271:87 (1994)]; UNII-QXB6XSA047 component FSBIGDSBMBYOPN-VKHMYHEASA-N; (2s)-2-amino-4-(((diaminomethylidene)amino)oxy)butanoic acid; 56C22C33-8657-4884-BE16-CAF24BF61D77; L-Canavanine, >=98% (TLC), powder, from Canavalia ensiformis
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Species Origin Canavalia ensiformis ...     Click to Show/Hide
Canavalia ensiformis
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Fabales
Family: Fabaceae
Genus: Canavalia
Species: Canavalia ensiformis
Disease Acute lymphoblastic leukemia [ICD-11: 2B33] Investigative [1]
Structure
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2D MOL

3D MOL

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Formula
C5H12N4O3
PubChem CID
439202
Canonical SMILES
C(CON=C(N)N)C(C(=O)O)N
InChI
1S/C5H12N4O3/c6-3(4(10)11)1-2-12-9-5(7)8/h3H,1-2,6H2,(H,10,11)(H4,7,8,9)/t3-/m0/s1
InChIKey
FSBIGDSBMBYOPN-VKHMYHEASA-N
CAS Number
CAS 543-38-4
ChEBI ID
CHEBI:609827
Herb ID
HBIN019533
SymMap ID
SMIT14563
TTD Drug ID
D0V9FZ
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          5-fluorouracil      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
                    In-vitro Model MIA PaCa-2 CVCL_0428 Pancreatic ductal adenocarcinoma Homo sapiens
                    In-vivo Model Male Fishcher rats weighing 150-175 g were used in this study.
                    Experimental
                    Result(s)		 Combination therapy offers a viable means of improving L-canavanine's intrinsic efficacy while decreasing the concentration of 5-FU required to produce the same cytotoxic effect.
Target and Pathway
Target(s) Nitric-oxide synthase endothelial (NOS3)  Molecule Info  [3]
BioCyc Citrulline-nitric oxide cycle Click to Show/Hide
KEGG Pathway Arginine and proline metabolism Click to Show/Hide
2 Metabolic pathways
3 Calcium signaling pathway
4 cGMP-PKG signaling pathway
5 HIF-1 signaling pathway
6 Sphingolipid signaling pathway
7 PI3K-Akt signaling pathway
8 VEGF signaling pathway
9 Platelet activation
10 Estrogen signaling pathway
11 Oxytocin signaling pathway
NetPath Pathway Wnt Signaling Pathway Click to Show/Hide
Panther Pathway Angiogenesis Click to Show/Hide
2 Endothelin signaling pathway
3 Interleukin signaling pathway
4 PI3 kinase pathway
5 VEGF signaling pathway
Pathway Interaction Database Plasma membrane estrogen receptor signaling Click to Show/Hide
2 Validated transcriptional targets of AP1 family members Fra1 and Fra2
3 Angiopoietin receptor Tie2-mediated signaling
4 Thromboxane A2 receptor signaling
5 SHP2 signaling
6 VEGFR1 specific signals
7 Signaling events mediated by VEGFR1 and VEGFR2
8 PAR1-mediated thrombin signaling events
Reactome ROS production in response to bacteria Click to Show/Hide
2 Tetrahydrobiopterin (BH4) synthesis, recycling, salvage and regulation
3 eNOS activation
4 Nitric oxide stimulates guanylate cyclase
5 VEGFR2 mediated vascular permeability
WikiPathways ACE Inhibitor Pathway Click to Show/Hide
2 EGF/EGFR Signaling Pathway
3 Myometrial Relaxation and Contraction Pathways
4 JAK/STAT
5 Corticotropin-releasing hormone
6 AGE/RAGE pathway
7 Endothelin Pathways
8 Leptin signaling pathway
9 Effects of Nitric Oxide
10 Metabolism of nitric oxide
11 Angiogenesis
References
Reference 1 Arginine antimetabolite L-canavanine induces apoptotic cell death in human Jurkat T cells via caspase-3 activation regulated by Bcl-2 or Bcl-xL. Biochem Biophys Res Commun. 2002 Jul 12;295(2):283-8.
Reference 2 Combination therapy with 5-fluorouracil and L-canavanine: in vitro and in vivo studies. Anticancer Drugs. 1995 Aug;6(4):586-93.
Reference 3 How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
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