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Showing NP-Card for L-Canavanine (NP0334853)

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Record Information
Version2.0
Created at2024-09-10 22:47:22 UTC
Updated at2024-09-10 22:47:22 UTC
NP-MRD IDNP0334853
Secondary Accession NumbersNone
Natural Product Identification
Common NameL-Canavanine
DescriptionL-Canavanine belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). L-Canavanine was first documented in 2006 (PMID: 30000890). Based on a literature review a significant number of articles have been published on L-Canavanine (PMID: 33032148) (PMID: 32839635) (PMID: 38941218) (PMID: 38577885) (PMID: 37852416) (PMID: 36173493).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0334853 (L-Canavanine)

Structure #1
  Mrv2104 05262301192D          

 12 11  0  0  0  0            999 V2000
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2 12  1  0  0  0  0
  3  4  1  0  0  0  0
  3  6  1  0  0  0  0
  4 10  1  0  0  0  0
  4 11  2  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  2  0  0  0  0
  9 12  1  0  0  0  0
M  END
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3D MOL for NP0334853 (L-Canavanine)

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3D SDF for NP0334853 (L-Canavanine)
Structure #1
  Mrv2104 05262301192D          

 12 11  0  0  0  0            999 V2000
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2 12  1  0  0  0  0
  3  4  1  0  0  0  0
  3  6  1  0  0  0  0
  4 10  1  0  0  0  0
  4 11  2  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  2  0  0  0  0
  9 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334853

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(CCON=C(N)N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1/C5H12N4O3/c6-3(4(10)11)1-2-12-9-5(7)8/h3H,1-2,6H2,(H,10,11)(H4,7,8,9)

> <INCHI_KEY>
FSBIGDSBMBYOPN-UHFFFAOYNA-N

> <FORMULA>
C5H12N4O3

> <MOLECULAR_WEIGHT>
176.176

> <EXACT_MASS>
176.090940262

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
17.084915791114724

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-4-{[(diaminomethylidene)amino]oxy}butanoic acid

> <JCHEM_LOGP>
-4.252480758127961

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
19.066986457673195

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.103228861610855

> <JCHEM_PKA_STRONGEST_BASIC>
9.115017136083262

> <JCHEM_POLAR_SURFACE_AREA>
136.95

> <JCHEM_REFRACTIVITY>
40.3359

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
DL-canavanine

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0334853 (L-Canavanine)
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PDB for NP0334853 (L-Canavanine)
HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       4.001   2.310   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      -2.667   3.080   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       0.000   3.080   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      -1.334   0.770   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0       6.668   0.770   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       5.335  -1.540   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1   12                                                       
CONECT    3    1    4    6                                                  
CONECT    4    3   10   11                                                  
CONECT    5    7    8    9                                                  
CONECT    6    3                                                            
CONECT    7    5                                                            
CONECT    8    5                                                            
CONECT    9    5   12                                                       
CONECT   10    4                                                            
CONECT   11    4                                                            
CONECT   12    2    9                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

Download
3D PDB for NP0334853 (L-Canavanine)
Download
SMILES for NP0334853 (L-Canavanine)
NC(CCON=C(N)N)C(O)=O
Download
INCHI for NP0334853 (L-Canavanine)
InChI=1/C5H12N4O3/c6-3(4(10)11)1-2-12-9-5(7)8/h3H,1-2,6H2,(H,10,11)(H4,7,8,9)
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View in JSmol
SynonymsNot Available
Chemical FormulaC5H12N4O3
Average Mass176.1760 Da
Monoisotopic Mass176.09094 Da
IUPAC Name2-amino-4-{[(diaminomethylidene)amino]oxy}butanoic acid
Traditional NameDL-canavanine
CAS Registry NumberNot Available
SMILES
NC(CCON=C(N)N)C(O)=O
InChI Identifier
InChI=1/C5H12N4O3/c6-3(4(10)11)1-2-12-9-5(7)8/h3H,1-2,6H2,(H,10,11)(H4,7,8,9)
InChI KeyFSBIGDSBMBYOPN-UHFFFAOYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentAlpha amino acids  
Alternative Parents
Substituents
  • Alpha-amino acid
    • 

  • Fatty acid
    • 

  • Guanidine
    • 

  • Amino acid
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organopnictogen compound
    • 

  • Primary amine
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic nitrogen compound
    • 

  • Primary aliphatic amine
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Amine
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-4.3ChemAxon
pKa (Strongest Acidic)2.1ChemAxon
pKa (Strongest Basic)9.12ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area136.95 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity40.34 m³·mol⁻¹ChemAxon
Polarizability17.08 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCanavanine  
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Almuhayawi MS, Hassan AHA, Al Jaouni SK, Alkhalifah DHM, Hozzein WN, Selim S, AbdElgawad H, Khamis G: Influence of elevated CO2 on nutritive value and health-promoting prospective of three genotypes of Alfalfa sprouts (Medicago Sativa). Food Chem. 2021 Mar 15;340:128147. doi: 10.1016/j.foodchem.2020.128147. Epub 2020 Sep 23. [PubMed:33032148  ] 
  2. Dwarka D, Agoni C, Mellem JJ, Soliman ME, Baijnath H: Identification of potential SARS-CoV-2 inhibitors from South African medicinal plant extracts using molecular modelling approaches. S Afr J Bot. 2020 Sep;133:273-284. doi: 10.1016/j.sajb.2020.07.035. Epub 2020 Aug 19. [PubMed:32839635  ] 
  3. Chiang Wong H, Gonzalez Guzman MDC, Gonzalez Saldana P: [Primary immune thrombocytopenia linked to the ingestion of guinea pigs (Cavia porcellus) causality or coincidence?]. Rev Fac Cien Med Univ Nac Cordoba. 2024 Jun 28;81(2):391-402. doi:  10.31053/1853.0605.v81.n2.44592. [PubMed:38941218  ] 
  4. Chatterjee S, Fellner M, Rankin J, Thomas MG, J S Rifayee SB, Christov CZ, Hu J, Hausinger RP: Structural, Spectroscopic, and Computational Insights from Canavanine-Bound and Two Catalytically Compromised Variants of the Ethylene-Forming Enzyme. Biochemistry. 2024 Apr 16;63(8):1038-1050. doi: 10.1021/acs.biochem.4c00031. Epub  2024 Apr 5. [PubMed:38577885  ] 
  5. Bhowal P, Roy B, Ganguli S, Igloi GL, Banerjee R: Elucidating the structure-function attributes of a trypanosomal arginyl-tRNA synthetase. Mol Biochem Parasitol. 2023 Dec;256:111597. doi:  10.1016/j.molbiopara.2023.111597. Epub 2023 Oct 16. [PubMed:37852416  ] 
  6. Artiles-Ortega E, de la Fe-Rodriguez PY, Reguera-Barreto B, Lima-Orozco R, Fievez V: In vitro rumen degradability of tropical legumes and their secondary metabolites depends on inoculum source. Trop Anim Health Prod. 2022 Sep 29;54(5):330. doi: 10.1007/s11250-022-03327-z. [PubMed:36173493  ] 
  7. Mardani-Korrani H, Nakayasu M, Yamazaki S, Aoki Y, Kaida R, Motobayashi T, Kobayashi M, Ohkama-Ohtsu N, Oikawa Y, Sugiyama A, Fujii Y: L-Canavanine, a Root Exudate From Hairy Vetch (Vicia villosa) Drastically Affecting the Soil Microbial Community and Metabolite Pathways. Front Microbiol. 2021 Sep 27;12:701796. doi: 10.3389/fmicb.2021.701796.  eCollection 2021. [PubMed:34646244  ] 
  8. Authors unspecified: Alfalfa.. 2006. [PubMed:30000890  ] 
  9. Ntuli SSBN, Gelderblom WCA, Katerere DR: The mutagenic and antimutagenic activity of Sutherlandia frutescens extracts and marker compounds. BMC Complement Altern Med. 2018 Mar 15;18(1):93. doi: 10.1186/s12906-018-2159-z. [PubMed:29544492  ] 
  10. Onselen RV, Downing S, Kemp G, Downing T: Investigating beta-N-Methylamino-l-alanine Misincorporation in Human Cell Cultures: A Comparative Study with Known Amino Acid Analogues. Toxins (Basel). 2017 Dec 14;9(12):400. doi: 10.3390/toxins9120400. [PubMed:29240689  ]