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Showing metabocard for 3-Oxoalanine (HMDB0011602)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-01-29 12:43:59 UTC
Update Date2023-02-21 17:17:29 UTC
HMDB IDHMDB0011602
Secondary Accession Numbers
  • HMDB11602
Metabolite Identification
Common Name3-Oxoalanine
Description3-Oxoalanine, also known as C-formylglycine or fgly, 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). 3-Oxoalanine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 3-oxoalanine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-Oxoalanine.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0011602 (3-Oxoalanine)

  Mrv0541 02241201472D          

  7  6  0  0  0  0            999 V2000
    8.3594  -10.3772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1844  -10.3772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5969  -11.0916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5969   -9.6627    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9469   -9.6627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9469  -11.0916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1844  -11.8061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  5  1  1  0  0  0  0
  6  1  2  0  0  0  0
  7  3  2  0  0  0  0
M  END
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3D MOL for HMDB0011602 (3-Oxoalanine)

HMDB0011602
     RDKit          3D
3-Oxoalanine
 12 11  0  0  0  0  0  0  0  0999 V2000
   -0.7450   -1.2084    0.1222 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1995    0.0607    0.4912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0808    1.1298   -0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0732    0.8085   -0.6455 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1635    0.2757   -0.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7873    1.3388    0.1897 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7898   -0.6834   -0.8059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7868   -1.2203    0.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3099   -1.5156   -0.7859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1407    0.1026    1.6056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8846    2.1785    0.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4800   -1.2668   -0.3198 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  2  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  2 10  1  0
  3 11  1  0
  7 12  1  0
M  END
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3D SDF for HMDB0011602 (3-Oxoalanine)

  Mrv0541 02241201472D          

  7  6  0  0  0  0            999 V2000
    8.3594  -10.3772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1844  -10.3772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5969  -11.0916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5969   -9.6627    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9469   -9.6627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9469  -11.0916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1844  -11.8061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  5  1  1  0  0  0  0
  6  1  2  0  0  0  0
  7  3  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0011602

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C3H5NO3/c4-2(1-5)3(6)7/h1-2H,4H2,(H,6,7)

> <INCHI_KEY>
XMTCKNXTTXDPJX-UHFFFAOYSA-N

> <FORMULA>
C3H5NO3

> <MOLECULAR_WEIGHT>
103.0767

> <EXACT_MASS>
103.026943031

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
8.592981726643526

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-3-oxopropanoic acid

> <ALOGPS_LOGP>
-2.78

> <JCHEM_LOGP>
-3.5556656946363905

> <ALOGPS_LOGS>
0.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.720415685624044

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.657152128565897

> <JCHEM_PKA_STRONGEST_BASIC>
7.183752655408849

> <JCHEM_POLAR_SURFACE_AREA>
80.39

> <JCHEM_REFRACTIVITY>
21.058100000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.42e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-formylglycine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0011602 (3-Oxoalanine)

HMDB0011602
     RDKit          3D
3-Oxoalanine
 12 11  0  0  0  0  0  0  0  0999 V2000
   -0.7450   -1.2084    0.1222 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1995    0.0607    0.4912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0808    1.1298   -0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0732    0.8085   -0.6455 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1635    0.2757   -0.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7873    1.3388    0.1897 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7898   -0.6834   -0.8059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7868   -1.2203    0.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3099   -1.5156   -0.7859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1407    0.1026    1.6056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8846    2.1785    0.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4800   -1.2668   -0.3198 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  2  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  2 10  1  0
  3 11  1  0
  7 12  1  0
M  END
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PDB for HMDB0011602 (3-Oxoalanine)

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      15.604 -19.371   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.144 -19.371   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.914 -20.704   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      17.914 -18.037   0.000  0.00  0.00           N+0
HETATM    5  O   UNK     0      14.834 -18.037   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      14.834 -20.704   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      17.144 -22.038   0.000  0.00  0.00           O+0
CONECT    1    2    5    6                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2    7                                                       
CONECT    4    2                                                            
CONECT    5    1                                                            
CONECT    6    1                                                            
CONECT    7    3                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for HMDB0011602 (3-Oxoalanine)

COMPND    HMDB0011602
HETATM    1  N1  UNL     1      -0.745  -1.208   0.122  1.00  0.00           N  
HETATM    2  C1  UNL     1      -0.199   0.061   0.491  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.081   1.130  -0.025  1.00  0.00           C  
HETATM    4  O1  UNL     1      -2.073   0.809  -0.646  1.00  0.00           O  
HETATM    5  C3  UNL     1       1.163   0.276  -0.041  1.00  0.00           C  
HETATM    6  O2  UNL     1       1.787   1.339   0.190  1.00  0.00           O  
HETATM    7  O3  UNL     1       1.790  -0.683  -0.806  1.00  0.00           O  
HETATM    8  H1  UNL     1      -1.787  -1.220   0.093  1.00  0.00           H  
HETATM    9  H2  UNL     1      -0.310  -1.516  -0.786  1.00  0.00           H  
HETATM   10  H3  UNL     1      -0.141   0.103   1.606  1.00  0.00           H  
HETATM   11  H4  UNL     1      -0.885   2.178   0.122  1.00  0.00           H  
HETATM   12  H5  UNL     1       2.480  -1.267  -0.320  1.00  0.00           H  
CONECT    1    2    8    9
CONECT    2    3    5   10
CONECT    3    4    4   11
CONECT    5    6    6    7
CONECT    7   12
END
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SMILES for HMDB0011602 (3-Oxoalanine)

NC(C=O)C(O)=O
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INCHI for HMDB0011602 (3-Oxoalanine)

InChI=1S/C3H5NO3/c4-2(1-5)3(6)7/h1-2H,4H2,(H,6,7)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
alpha-FormylglycineChEBI
C(alpha)-FormylglycineChEBI
C-FormylglycineChEBI
FGlyChEBI
a-FormylglycineGenerator
Α-formylglycineGenerator
C(a)-FormylglycineGenerator
C(Α)-formylglycineGenerator
2-amino-3-oxo-PropanoateHMDB
2-amino-3-oxo-Propanoic acidHMDB
2-FormylglycineHMDB
3-oxo-(9CI)-alanineHMDB
amino-(8CI)malonaldehydic acidHMDB
L-alpha-FormylglycineMeSH, HMDB
2-amino-3-Oxopropanoic acidMeSH, HMDB
3-oxo-L-AlanineMeSH, HMDB
Chemical FormulaC3H5NO3
Average Molecular Weight103.0767
Monoisotopic Molecular Weight103.026943031
IUPAC Name2-amino-3-oxopropanoic acid
Traditional Nameα-formylglycine
CAS Registry Number5735-66-0
SMILES
NC(C=O)C(O)=O
InChI Identifier
InChI=1S/C3H5NO3/c4-2(1-5)3(6)7/h1-2H,4H2,(H,6,7)
InChI KeyXMTCKNXTTXDPJX-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • 1,3-dicarbonyl compound
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Aldehyde
  • Hydrocarbon derivative
  • Organic oxide
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
RoleNot Available
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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028313
KNApSAcK IDNot Available
Chemspider ID28
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound29
PDB IDNot Available
ChEBI ID17740
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 References
  1. Lukatela G, Krauss N, Theis K, Selmer T, Gieselmann V, von Figura K, Saenger W: Crystal structure of human arylsulfatase A: the aldehyde function and the metal ion at the active site suggest a novel mechanism for sulfate ester hydrolysis. Biochemistry. 1998 Mar 17;37(11):3654-64. [PubMed:9521684 ]