Compound: L-canavanine
SMILES: O=C(O)[C@@H](N)CCON=C(N)N
InChIKey: FSBIGDSBMBYOPN-VKHMYHEASA-N
Synonyms: L-canavanine, canavanine, 543-38-4, Canavanin, 2-Amino-4-(guanidinooxy)butyric acid, (L)-CANAVANINE, O-((Aminoiminomethyl)amino)-L-homoserine, (2S)-2-amino-4-(diaminomethylideneamino)oxybutanoic acid, 3HZV514J4B, L-Homoserine, O-((aminoiminomethyl)amino)-, Butyric acid, 2-amino-4-(guanidinooxy)-, L-, O-[(Aminoiminomethyl)amino]-L-homoserine, DTXSID5045041, CHEBI:609827, (2S)-2-amino-4-(carbamimidamidooxy)butanoic acid, RefChem:795154, DTXCID3025041, (2S)-2-azaniumyl-4-(diaminomethylideneamino)oxybutanoate, L-Alpha-amino-gamma-[guanidinooxy]-N-butyric acid, CHEMBL443732, (S)-2-Amino-4-(guanidinooxy)butanoic acid, 2-azaniumyl-4-(diaminomethylideneamino)oxybutanoate, (2S)-2-amino-4-guanidinooxy-butanoic acid, GGB, L-Cav;LDN 21810, L-2-AMINO-4-(GUANIDINOOXY)BUTYRIC ACID, L-alpha-Amino-gamma-(guanidinooxy)-n-butyric acid, (+)-CANAVANINE, UNII-3HZV514J4B, HSDB 3471, L(+)-Canavanine, Spectrum_001137, Tocris-0673, CANAVANINE [MI], L-CAV, AI3-52153, Prestwick3_000609, Spectrum2_000800, Spectrum3_001206, Spectrum4_000783, Spectrum5_001884, CANAVANINE [HSDB], Lopac-C-9758, bmse000073, CANAVANINE, (+)-, Lopac0_000320, BSPBio_000518, BSPBio_002592, KBioGR_001226, KBioSS_001617, DivK1c_000360, O-carbamimidamido-L-homoserine, SCHEMBL151097, SCHEMBL151098, SPECTRUM1500833, SPBio_000940, BPBio1_000570, orb1702663, HMS501B22, KBio1_000360, KBio2_001617, KBio2_004185, KBio2_006753, KBio3_002092, FSBIGDSBMBYOPN-VKHMYHEASA-N, NINDS_000360, HMS1921K08, HY-B1581, O-(Carbamimidoylamino)-L-homoserine, BDBM50271982, BDBM50370459, CCG-40178, MFCD00055781, 2-amino-4-(guanidinoxy) butyric acid, AKOS006240676, DB01833, SDCCGMLS-0066683.P001, SDCCGSBI-0050308.P003, IDI1_000360, SMP1_000062, NCGC00015287-01, NCGC00015287-14, NCGC00015287-18, NCGC00015287-19, NCGC00024722-01, NCGC00024722-02, NCGC00024722-03, NCGC00024722-04, AS-87378, FC162286, O-{[Amino(imino)methyl]amino}-L-homoserine, CS-0013477, NS00014863, Butyric acid, 2-amino-4-(guanidinooxy)-, L, C00308, G77710, Q418408, [Eur.J.Pharmacol. 269:269; 271:87 (1994)], (2s)-2-amino-4-(((diaminomethylidene)amino)oxy)butanoic acid, 56C22C33-8657-4884-BE16-CAF24BF61D77, L-Canavanine, >=98% (TLC), powder, from Canavalia ensiformis
Theoretical properties:
molecular_formula: C5H12N4O3
molecular_weight: 176.17 g/mol
exact_mass: 176.09094026 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 4
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 5
heavy_atom_count: 12
topological_polar_surface_area: 137 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals from absolute alcohol
color: Crystals from absolute alcohol
melting_point: 184 °C
solubility: Very soluble in water
Descriptions:
pubchem: L-canavanine is a non-proteinogenic L-alpha-amino acid that is L-homoserine substituted at oxygen with a guanidino (carbamimidamido) group. Although structurally related to L-arginine, it is non-proteinogenic. It has a role as a phytogenic insecticide and a plant metabolite. It is functionally related to a L-homoserine. It is a conjugate base of a L-canavanine(1+). It is a tautomer of a L-canavanine zwitterion.
chebi: <small>L</small>-Canavanine in zwitterionic form.
chembl: CANAVANINE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: L-(+)-(S)-Canavanine is a non-proteinogenic amino acid found in certain leguminous plants. It is structurally related to the proteinogenic α-amino acid L-arginine, the sole difference being the replacement of a methylene bridge (−CH2− unit) in arginine with an oxa group (i.e., an oxygen atom) in canavanine. Canavanine is accumulated primarily in the seeds of the organisms which produce it, where it serves both as a highly deleterious defensive compound against herbivores (due to cells mistaking it for arginine) and a vital source of nitrogen for the growing embryo. The related L-canaline is similar to ornithine.