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Showing NP-Card for Canavanine (NP0001308)

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Record Information
Version2.0
Created at2006-05-22 15:12:04 UTC
Updated at2021-06-29 00:47:37 UTC
NP-MRD IDNP0001308
Secondary Accession NumbersNone
Natural Product Identification
Common NameCanavanine
DescriptionL-Canavanine, a non-protein amino acid of certain leguminous plants, is related structurally to the protein amino acid, L-arginine. Canavanine is accumulated primarily in the seeds where it serves both as a defensive compound against herbivores and a vital source of nitrogen for the growing embryo. Organisms that consume it can mistakenly incorporate it into their own proteins, in the place of arginine thereby producing structurally aberrant proteins that may not function properly or not at all. Some specialized herbivores tolerate L-canavanine either because they metabolize it efficiently or avoid its incorporation into their own nascent proteins.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001308 (Canavanine)


  Mrv1652305271900052D          

 12 11  0  0  1  0            999 V2000
    7.2849    3.3809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    1.3184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
Download

3D MOL for NP0001308 (Canavanine)

HMDB0002706
     RDKit          3D
Canavanine
 24 23  0  0  0  0  0  0  0  0999 V2000
    4.0966    0.7373    0.9524 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3478    0.0610   -0.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8592   -0.1187   -1.2510 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0108   -0.2380    0.4632 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9526   -0.6513   -0.1829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0429   -0.6006    0.9236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2257    0.1219    0.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4035   -0.4062   -0.2392 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2344   -1.3346   -1.3944 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9942    0.8604   -0.8719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3423    0.6129   -2.1883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2584    2.0717   -0.5148 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9958    1.0708    0.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1367    0.6603   -1.8646 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9862   -1.1109   -1.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7786    0.0657    1.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3400   -1.7627    1.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3784   -0.3837    1.8174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7368    0.9299   -0.3019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6182    0.8609    1.2391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1543   -0.8048    0.4218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4890   -2.3205   -0.9683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0811   -1.2098   -2.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6217    2.8891   -0.5676 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
  1 13  1  0
  3 14  1  0
  3 15  1  0
  4 16  1  0
  6 17  1  0
  6 18  1  0
  7 19  1  0
  7 20  1  0
  8 21  1  1
  9 22  1  0
  9 23  1  0
 12 24  1  0
M  END
Download

3D SDF for NP0001308 (Canavanine)


  Mrv1652305271900052D          

 12 11  0  0  1  0            999 V2000
    7.2849    3.3809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    1.3184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0001308

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H](CCONC(N)=N)C(O)=O

> <INCHI_IDENTIFIER>
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

> <INCHI_KEY>
FSBIGDSBMBYOPN-VKHMYHEASA-N

> <FORMULA>
C5H12N4O3

> <MOLECULAR_WEIGHT>
176.1738

> <EXACT_MASS>
176.09094027

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
17.023159241488404

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-4-(carbamimidamidooxy)butanoic acid

> <ALOGPS_LOGP>
-3.86

> <JCHEM_LOGP>
-3.7018804133845005

> <ALOGPS_LOGS>
-1.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.1032409501189444

> <JCHEM_PKA_STRONGEST_BASIC>
10.343629284146132

> <JCHEM_POLAR_SURFACE_AREA>
134.45000000000002

> <JCHEM_REFRACTIVITY>
61.2436

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.77e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
canavanine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0001308 (Canavanine)

HMDB0002706
     RDKit          3D
Canavanine
 24 23  0  0  0  0  0  0  0  0999 V2000
    4.0966    0.7373    0.9524 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3478    0.0610   -0.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8592   -0.1187   -1.2510 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0108   -0.2380    0.4632 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9526   -0.6513   -0.1829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0429   -0.6006    0.9236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2257    0.1219    0.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4035   -0.4062   -0.2392 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2344   -1.3346   -1.3944 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9942    0.8604   -0.8719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3423    0.6129   -2.1883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2584    2.0717   -0.5148 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9958    1.0708    0.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1367    0.6603   -1.8646 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9862   -1.1109   -1.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7786    0.0657    1.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3400   -1.7627    1.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3784   -0.3837    1.8174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7368    0.9299   -0.3019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6182    0.8609    1.2391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1543   -0.8048    0.4218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4890   -2.3205   -0.9683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0811   -1.2098   -2.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6217    2.8891   -0.5676 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
  1 13  1  0
  3 14  1  0
  3 15  1  0
  4 16  1  0
  6 17  1  0
  6 18  1  0
  7 19  1  0
  7 20  1  0
  8 21  1  1
  9 22  1  0
  9 23  1  0
 12 24  1  0
M  END
Download

PDB for NP0001308 (Canavanine)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  N   UNK     0      13.598   6.311   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       9.597   4.001   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       8.264   4.771   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       5.596   4.771   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       6.930   2.461   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      16.266   4.771   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      14.932   2.461   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    2   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END
Download

3D PDB for NP0001308 (Canavanine)

COMPND    HMDB0002706
HETATM    1  N1  UNL     1       4.097   0.737   0.952  1.00  0.00           N  
HETATM    2  C1  UNL     1       3.348   0.061  -0.021  1.00  0.00           C  
HETATM    3  N2  UNL     1       3.859  -0.119  -1.251  1.00  0.00           N  
HETATM    4  N3  UNL     1       2.011  -0.238   0.463  1.00  0.00           N  
HETATM    5  O1  UNL     1       0.953  -0.651  -0.183  1.00  0.00           O  
HETATM    6  C2  UNL     1      -0.043  -0.601   0.924  1.00  0.00           C  
HETATM    7  C3  UNL     1      -1.226   0.122   0.419  1.00  0.00           C  
HETATM    8  C4  UNL     1      -2.404  -0.406  -0.239  1.00  0.00           C  
HETATM    9  N4  UNL     1      -2.234  -1.335  -1.394  1.00  0.00           N  
HETATM   10  C5  UNL     1      -2.994   0.860  -0.872  1.00  0.00           C  
HETATM   11  O2  UNL     1      -3.342   0.613  -2.188  1.00  0.00           O  
HETATM   12  O3  UNL     1      -3.258   2.072  -0.515  1.00  0.00           O  
HETATM   13  H1  UNL     1       4.996   1.071   0.633  1.00  0.00           H  
HETATM   14  H2  UNL     1       4.137   0.660  -1.865  1.00  0.00           H  
HETATM   15  H3  UNL     1       3.986  -1.111  -1.565  1.00  0.00           H  
HETATM   16  H4  UNL     1       1.779   0.066   1.503  1.00  0.00           H  
HETATM   17  H5  UNL     1      -0.340  -1.763   1.066  1.00  0.00           H  
HETATM   18  H6  UNL     1       0.378  -0.384   1.817  1.00  0.00           H  
HETATM   19  H7  UNL     1      -0.737   0.930  -0.302  1.00  0.00           H  
HETATM   20  H8  UNL     1      -1.618   0.861   1.239  1.00  0.00           H  
HETATM   21  H9  UNL     1      -3.154  -0.805   0.422  1.00  0.00           H  
HETATM   22  H10 UNL     1      -2.489  -2.320  -0.968  1.00  0.00           H  
HETATM   23  H11 UNL     1      -3.081  -1.210  -2.059  1.00  0.00           H  
HETATM   24  H12 UNL     1      -2.622   2.889  -0.568  1.00  0.00           H  
CONECT    1    2    2   13
CONECT    2    3    4
CONECT    3   14   15
CONECT    4    5   16
CONECT    5    6
CONECT    6    7   17   18
CONECT    7    8   19   20
CONECT    8    9   10   21
CONECT    9   22   23
CONECT   10   11   11   12
CONECT   12   24
END
Download

SMILES for NP0001308 (Canavanine)

N[C@@H](CCONC(N)=N)C(O)=O
Download

INCHI for NP0001308 (Canavanine)

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
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View in JSmol
Synonyms
ValueSource
(2S)-2-Ammonio-4-(carbamimidamidooxy)butanoateChEBI
L-CanavanineChEBI
2-Amino-4-(guanidinooxy)butyric acidKegg
(2S)-2-Ammonio-4-(carbamimidamidooxy)butanoic acidGenerator
2-Amino-4-(guanidinooxy)butyrateGenerator
CanavaninHMDB
O-((Aminoiminomethyl)amino)homoserineHMDB
L-2-Amino-4-(guanidinooxy)butyrateHMDB
CanavanineMeSH
Chemical FormulaC5H12N4O3
Average Mass176.1738 Da
Monoisotopic Mass176.09094 Da
IUPAC Name(2S)-2-amino-4-(carbamimidamidooxy)butanoic acid
Traditional Namecanavanine
CAS Registry Number543-38-4
SMILES
N[C@@H](CCONC(N)=N)C(O)=O
InChI Identifier
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
InChI KeyFSBIGDSBMBYOPN-VKHMYHEASA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Canavalia ensiformisKNApSAcK Database
Canavalia gladiataLOTUS Database
Canavalia lineataLOTUS Database
Colutea arborescensLOTUS Database
Indigofera hirsutaLOTUS Database
Medicago intertextaKNApSAcK Database
Medicago sativaLOTUS Database
Peteria glandulosaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Fatty acid
  • Guanidine
  • Amino acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Amine
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point184 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-3.324Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.77 g/LALOGPS
logP-3.9ALOGPS
logP-3.7ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)2.1ChemAxon
pKa (Strongest Basic)10.34ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area134.45 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity61.24 m³·mol⁻¹ChemAxon
Polarizability17.02 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002706
DrugBank IDDB01833
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000505
KNApSAcK IDC00001347
Chemspider ID388342
KEGG Compound IDC00308
BioCyc IDCANAVANINE
BiGG IDNot Available
Wikipedia LinkCanavanine
METLIN ID3238
PubChem Compound439202
PDB IDNot Available
ChEBI ID405237
Good Scents IDNot Available
References
General References
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