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Showing metabocard for L-Canaline (HMDB0012251)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:21:46 UTC
Update Date2023-02-21 17:17:46 UTC
HMDB IDHMDB0012251
Secondary Accession Numbers
  • HMDB12251
Metabolite Identification
Common NameL-Canaline
DescriptionL-Canaline 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. L-Canaline has been detected, but not quantified in, several different foods, such as american cranberries (Vaccinium macrocarpon), garden tomatoes (Solanum lycopersicum), gingers (Zingiber officinale), lentils (Lens culinaris), and brassicas. This could make L-canaline a potential biomarker for the consumption of these foods. L-Canaline is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on L-Canaline.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0012251 (L-Canaline)

  Mrv0541 02241203532D          

  9  8  0  0  1  0            999 V2000
   10.3181  -13.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1430  -13.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9056  -13.9572    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.3181  -14.6717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0807  -13.9572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3804  -12.5281    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9056  -15.3862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1430  -14.6717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5555  -12.5281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  2  1  0  0  0  0
  2  9  1  0  0  0  0
  3  5  1  1  0  0  0
  3  4  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  2  0  0  0  0
  6  9  1  0  0  0  0
M  END
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3D MOL for HMDB0012251 (L-Canaline)

HMDB0012251
     RDKit          3D
L-Canaline
 19 18  0  0  0  0  0  0  0  0999 V2000
    3.5268   -0.1231    0.1818 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3905   -0.6447   -0.3333 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2634   -0.1740    0.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0113   -0.7601   -0.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2528   -0.3342    0.4757 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3596   -0.9510   -0.1597 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4584    1.1141    0.5553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6456    1.9094    1.0906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6080    1.6883    0.0198 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3947    0.8939    0.4320 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2958   -0.2368   -0.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4116   -0.4469    1.4345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2951    0.9377    0.2710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0909   -1.8577   -0.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0420   -0.4700   -1.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2103   -0.7239    1.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2510   -1.8834   -0.5117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2680   -0.5420   -0.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5842    2.6042   -0.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  3 12  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  5 16  1  1
  6 17  1  0
  6 18  1  0
  9 19  1  0
M  END
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3D SDF for HMDB0012251 (L-Canaline)

  Mrv0541 02241203532D          

  9  8  0  0  1  0            999 V2000
   10.3181  -13.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1430  -13.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9056  -13.9572    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.3181  -14.6717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0807  -13.9572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3804  -12.5281    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9056  -15.3862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1430  -14.6717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5555  -12.5281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  2  1  0  0  0  0
  2  9  1  0  0  0  0
  3  5  1  1  0  0  0
  3  4  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  2  0  0  0  0
  6  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012251

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C4H10N2O3/c5-3(4(7)8)1-2-9-6/h3H,1-2,5-6H2,(H,7,8)/t3-/m0/s1

> <INCHI_KEY>
FQPGMQABJNQLLF-VKHMYHEASA-N

> <FORMULA>
C4H10N2O3

> <MOLECULAR_WEIGHT>
134.1338

> <EXACT_MASS>
134.069142196

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
12.913467740284961

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-3.21

> <JCHEM_LOGP>
-3.6742692699487223

> <ALOGPS_LOGS>
0.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.235577728929878

> <JCHEM_PKA_STRONGEST_BASIC>
9.456516363364843

> <JCHEM_POLAR_SURFACE_AREA>
98.57000000000001

> <JCHEM_REFRACTIVITY>
30.976100000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.08e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
canaline

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0012251 (L-Canaline)

HMDB0012251
     RDKit          3D
L-Canaline
 19 18  0  0  0  0  0  0  0  0999 V2000
    3.5268   -0.1231    0.1818 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3905   -0.6447   -0.3333 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2634   -0.1740    0.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0113   -0.7601   -0.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2528   -0.3342    0.4757 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3596   -0.9510   -0.1597 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4584    1.1141    0.5553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6456    1.9094    1.0906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6080    1.6883    0.0198 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3947    0.8939    0.4320 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2958   -0.2368   -0.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4116   -0.4469    1.4345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2951    0.9377    0.2710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0909   -1.8577   -0.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0420   -0.4700   -1.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2103   -0.7239    1.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2510   -1.8834   -0.5117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2680   -0.5420   -0.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5842    2.6042   -0.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  3 12  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  5 16  1  1
  6 17  1  0
  6 18  1  0
  9 19  1  0
M  END
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PDB for HMDB0012251 (L-Canaline)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      19.260 -24.720   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.800 -24.720   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.490 -26.053   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.260 -27.387   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      16.951 -26.053   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      23.110 -23.386   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0      18.490 -28.721   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      20.800 -27.387   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      21.570 -23.386   0.000  0.00  0.00           O+0
CONECT    1    3    2                                                       
CONECT    2    1    9                                                       
CONECT    3    1    5    4                                                  
CONECT    4    3    7    8                                                  
CONECT    5    3                                                            
CONECT    6    9                                                            
CONECT    7    4                                                            
CONECT    8    4                                                            
CONECT    9    2    6                                                       
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for HMDB0012251 (L-Canaline)

COMPND    HMDB0012251
HETATM    1  N1  UNL     1       3.527  -0.123   0.182  1.00  0.00           N  
HETATM    2  O1  UNL     1       2.390  -0.645  -0.333  1.00  0.00           O  
HETATM    3  C1  UNL     1       1.263  -0.174   0.378  1.00  0.00           C  
HETATM    4  C2  UNL     1       0.011  -0.760  -0.204  1.00  0.00           C  
HETATM    5  C3  UNL     1      -1.253  -0.334   0.476  1.00  0.00           C  
HETATM    6  N2  UNL     1      -2.360  -0.951  -0.160  1.00  0.00           N  
HETATM    7  C4  UNL     1      -1.458   1.114   0.555  1.00  0.00           C  
HETATM    8  O2  UNL     1      -0.646   1.909   1.091  1.00  0.00           O  
HETATM    9  O3  UNL     1      -2.608   1.688   0.020  1.00  0.00           O  
HETATM   10  H1  UNL     1       3.395   0.894   0.432  1.00  0.00           H  
HETATM   11  H2  UNL     1       4.296  -0.237  -0.507  1.00  0.00           H  
HETATM   12  H3  UNL     1       1.412  -0.447   1.435  1.00  0.00           H  
HETATM   13  H4  UNL     1       1.295   0.938   0.271  1.00  0.00           H  
HETATM   14  H5  UNL     1       0.091  -1.858  -0.197  1.00  0.00           H  
HETATM   15  H6  UNL     1      -0.042  -0.470  -1.287  1.00  0.00           H  
HETATM   16  H7  UNL     1      -1.210  -0.724   1.533  1.00  0.00           H  
HETATM   17  H8  UNL     1      -2.251  -1.883  -0.512  1.00  0.00           H  
HETATM   18  H9  UNL     1      -3.268  -0.542  -0.050  1.00  0.00           H  
HETATM   19  H10 UNL     1      -2.584   2.604  -0.388  1.00  0.00           H  
CONECT    1    2   10   11
CONECT    2    3
CONECT    3    4   12   13
CONECT    4    5   14   15
CONECT    5    6    7   16
CONECT    6   17   18
CONECT    7    8    8    9
CONECT    9   19
END
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SMILES for HMDB0012251 (L-Canaline)

NOCC[C@H](N)C(O)=O
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INCHI for HMDB0012251 (L-Canaline)

InChI=1S/C4H10N2O3/c5-3(4(7)8)1-2-9-6/h3H,1-2,5-6H2,(H,7,8)/t3-/m0/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(2S)-2-Amino-4-(aminooxy)butanoic acidChEBI
(2S)-2-Amino-4-(aminooxy)butyric acidChEBI
CanalineChEBI
L-2-Amino-4-(aminooxy)butyric acidChEBI
(2S)-2-Amino-4-(aminooxy)butanoateGenerator
(2S)-2-Amino-4-(aminooxy)butyrateGenerator
L-2-Amino-4-(aminooxy)butyrateGenerator
L-a-Amino-g-(aminooxy)-N-butyric acidHMDB
L-alpha-Amino-gamma-(aminooxy)-N-butyric acidHMDB
1-Amino-3-amino-oxybutyric acidHMDB
L-CanalineMeSH
Chemical FormulaC4H10N2O3
Average Molecular Weight134.1338
Monoisotopic Molecular Weight134.069142196
IUPAC Name(2S)-2-amino-4-(aminooxy)butanoic acid
Traditional Namecanaline
CAS Registry Number496-93-5
SMILES
NOCC[C@H](N)C(O)=O
InChI Identifier
InChI=1S/C4H10N2O3/c5-3(4(7)8)1-2-9-6/h3H,1-2,5-6H2,(H,7,8)/t3-/m0/s1
InChI KeyFQPGMQABJNQLLF-VKHMYHEASA-N
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
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Route of exposureSource
ProcessNot Available
Role
Industrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02821
Phenol Explorer Compound IDNot Available
FooDB IDFDB030959
KNApSAcK IDC00001346
Chemspider ID390176
KEGG Compound IDC08270
BioCyc IDL-CANALINE
BiGG IDNot Available
Wikipedia LinkCanaline
METLIN IDNot Available
PubChem Compound441443
PDB IDNot Available
ChEBI ID41401
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Ornithine aminotransferase, mitochondrial
General function:
Involved in transaminase activity
Specific function:
Not Available
Gene Name:
OAT
Uniprot ID:
P04181
Molecular weight:
48534.39
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]