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Showing metabocard for (2S)-1,2-Dimethyl-3,4-dioxoazetidine-2-carboxylic acid (HMDB0257875)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 18:58:41 UTC
Update Date2021-09-26 23:14:28 UTC
HMDB IDHMDB0257875
Secondary Accession NumbersNone
Metabolite Identification
Common Name(2S)-1,2-Dimethyl-3,4-dioxoazetidine-2-carboxylic acid
Description1,2-dimethyl-3,4-dioxoazetidine-2-carboxylic acid belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Based on a literature review a significant number of articles have been published on 1,2-dimethyl-3,4-dioxoazetidine-2-carboxylic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). (2s)-1,2-dimethyl-3,4-dioxoazetidine-2-carboxylic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (2S)-1,2-Dimethyl-3,4-dioxoazetidine-2-carboxylic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0257875 ((2S)-1,2-Dimethyl-3,4-dioxoazetidine-2-carboxylic acid)


  Mrv1652309112120592D          

 11 11  0  0  0  0            999 V2000
   -0.1709    1.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.9959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9959    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8209    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.1709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.9959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1709    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9959    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9959    1.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7823    2.3761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7928    1.3657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
M  END
Download

3D MOL for HMDB0257875 ((2S)-1,2-Dimethyl-3,4-dioxoazetidine-2-carboxylic acid)

HMDB0257875
     RDKit          3D
(2S)-1,2-Dimethyl-3,4-dioxoazetidine-2-carboxylic acid
 18 18  0  0  0  0  0  0  0  0999 V2000
   -1.1487    0.5021    1.8788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8988    0.1271    0.5294 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7222   -0.1897   -0.5654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8757   -0.6617   -0.8046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6557    0.2705   -1.4276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4807    0.7494   -2.5581 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2376   -0.0943   -0.3101 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6433   -1.5544   -0.4609 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3871    0.8145   -0.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3378    1.6989    0.7654 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5302    0.6767   -0.8586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2276    0.2683    2.4815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0368   -0.0087    2.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3386    1.6100    1.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9204   -1.9765    0.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4799   -1.5725   -1.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1829   -2.1276   -0.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0314    1.4681   -1.2483 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
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
  7  2  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  8 15  1  0
  8 16  1  0
  8 17  1  0
 11 18  1  0
M  END
Download

3D SDF for HMDB0257875 ((2S)-1,2-Dimethyl-3,4-dioxoazetidine-2-carboxylic acid)


  Mrv1652309112120592D          

 11 11  0  0  0  0            999 V2000
   -0.1709    1.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.9959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9959    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8209    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.1709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.9959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1709    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9959    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9959    1.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7823    2.3761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7928    1.3657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0257875

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C(=O)C(=O)C1(C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H7NO4/c1-6(5(10)11)3(8)4(9)7(6)2/h1-2H3,(H,10,11)

> <INCHI_KEY>
QKNVJGOKVSAVSL-UHFFFAOYSA-N

> <FORMULA>
C6H7NO4

> <MOLECULAR_WEIGHT>
157.125

> <EXACT_MASS>
157.037507709

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
13.908319320932918

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,2-dimethyl-3,4-dioxoazetidine-2-carboxylic acid

> <ALOGPS_LOGP>
-0.65

> <JCHEM_LOGP>
-0.16530358900000003

> <ALOGPS_LOGS>
-0.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.210545335409271

> <JCHEM_PKA_STRONGEST_BASIC>
-5.396012461864533

> <JCHEM_POLAR_SURFACE_AREA>
74.68

> <JCHEM_REFRACTIVITY>
33.7396

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.00e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,2-dimethyl-3,4-dioxoazetidine-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0257875 ((2S)-1,2-Dimethyl-3,4-dioxoazetidine-2-carboxylic acid)

HMDB0257875
     RDKit          3D
(2S)-1,2-Dimethyl-3,4-dioxoazetidine-2-carboxylic acid
 18 18  0  0  0  0  0  0  0  0999 V2000
   -1.1487    0.5021    1.8788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8988    0.1271    0.5294 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7222   -0.1897   -0.5654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8757   -0.6617   -0.8046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6557    0.2705   -1.4276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4807    0.7494   -2.5581 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2376   -0.0943   -0.3101 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6433   -1.5544   -0.4609 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3871    0.8145   -0.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3378    1.6989    0.7654 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5302    0.6767   -0.8586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2276    0.2683    2.4815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0368   -0.0087    2.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3386    1.6100    1.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9204   -1.9765    0.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4799   -1.5725   -1.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1829   -2.1276   -0.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0314    1.4681   -1.2483 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
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
  7  2  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  8 15  1  0
  8 16  1  0
  8 17  1  0
 11 18  1  0
M  END
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PDB for HMDB0257875 ((2S)-1,2-Dimethyl-3,4-dioxoazetidine-2-carboxylic acid)

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      -0.319   2.948   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.770   1.859   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.859   0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.399   0.770   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.770  -0.319   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.770  -1.859   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0      -0.319   0.770   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -1.859   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.859   2.948   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.460   4.435   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       3.346   2.549   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7    9                                             
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    2    8                                                  
CONECT    8    7                                                            
CONECT    9    2   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0257875 ((2S)-1,2-Dimethyl-3,4-dioxoazetidine-2-carboxylic acid)

COMPND    HMDB0257875
HETATM    1  C1  UNL     1      -1.149   0.502   1.879  1.00  0.00           C  
HETATM    2  N1  UNL     1      -0.899   0.127   0.529  1.00  0.00           N  
HETATM    3  C2  UNL     1      -1.722  -0.190  -0.565  1.00  0.00           C  
HETATM    4  O1  UNL     1      -2.876  -0.662  -0.805  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.656   0.270  -1.428  1.00  0.00           C  
HETATM    6  O2  UNL     1      -0.481   0.749  -2.558  1.00  0.00           O  
HETATM    7  C4  UNL     1       0.238  -0.094  -0.310  1.00  0.00           C  
HETATM    8  C5  UNL     1       0.643  -1.554  -0.461  1.00  0.00           C  
HETATM    9  C6  UNL     1       1.387   0.815  -0.094  1.00  0.00           C  
HETATM   10  O3  UNL     1       1.338   1.699   0.765  1.00  0.00           O  
HETATM   11  O4  UNL     1       2.530   0.677  -0.859  1.00  0.00           O  
HETATM   12  H1  UNL     1      -0.228   0.268   2.482  1.00  0.00           H  
HETATM   13  H2  UNL     1      -2.037  -0.009   2.313  1.00  0.00           H  
HETATM   14  H3  UNL     1      -1.339   1.610   1.945  1.00  0.00           H  
HETATM   15  H4  UNL     1       0.920  -1.976   0.524  1.00  0.00           H  
HETATM   16  H5  UNL     1       1.480  -1.572  -1.190  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.183  -2.128  -0.920  1.00  0.00           H  
HETATM   18  H7  UNL     1       3.031   1.468  -1.248  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    7
CONECT    3    4    4    5
CONECT    5    6    6    7
CONECT    7    8    9
CONECT    8   15   16   17
CONECT    9   10   10   11
CONECT   11   18
END
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SMILES for HMDB0257875 ((2S)-1,2-Dimethyl-3,4-dioxoazetidine-2-carboxylic acid)

CN1C(=O)C(=O)C1(C)C(O)=O
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INCHI for HMDB0257875 ((2S)-1,2-Dimethyl-3,4-dioxoazetidine-2-carboxylic acid)

InChI=1S/C6H7NO4/c1-6(5(10)11)3(8)4(9)7(6)2/h1-2H3,(H,10,11)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
1,2-Dimethyl-3,4-dioxoazetidine-2-carboxylateGenerator
(2S)-1,2-Dimethyl-3,4-dioxoazetidine-2-carboxylateGenerator
Chemical FormulaC6H7NO4
Average Molecular Weight157.125
Monoisotopic Molecular Weight157.037507709
IUPAC Name1,2-dimethyl-3,4-dioxoazetidine-2-carboxylic acid
Traditional Name1,2-dimethyl-3,4-dioxoazetidine-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CN1C(=O)C(=O)C1(C)C(O)=O
InChI Identifier
InChI=1S/C6H7NO4/c1-6(5(10)11)3(8)4(9)7(6)2/h1-2H3,(H,10,11)
InChI KeyQKNVJGOKVSAVSL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids and derivatives
Alternative Parents
Substituents
  • Alpha-amino acid or derivatives
  • Azetidinecarboxylic acid
  • Beta-lactam
  • Tertiary carboxylic acid amide
  • Azetidine
  • Carboxamide group
  • Ketone
  • Cyclic ketone
  • Lactam
  • Azacycle
  • Carboxylic acid
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
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
PropertyValueSource
logP-0.65ALOGPS
logP-0.17ChemAxon
logS-0.19ALOGPS
pKa (Strongest Acidic)3.21ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area74.68 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity33.74 m³·mol⁻¹ChemAxon
Polarizability13.91 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+132.02730932474
DeepCCS[M-H]-128.230932474
DeepCCS[M-2H]-165.80530932474
DeepCCS[M+Na]+141.34430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(2S)-1,2-Dimethyl-3,4-dioxoazetidine-2-carboxylic acidCN1C(=O)C(=O)C1(C)C(O)=O2148.6Standard polar33892256
(2S)-1,2-Dimethyl-3,4-dioxoazetidine-2-carboxylic acidCN1C(=O)C(=O)C1(C)C(O)=O1087.3Standard non polar33892256
(2S)-1,2-Dimethyl-3,4-dioxoazetidine-2-carboxylic acidCN1C(=O)C(=O)C1(C)C(O)=O1233.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (2S)-1,2-Dimethyl-3,4-dioxoazetidine-2-carboxylic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6u-9300000000-e5c447efc50a50b1c2a22021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (2S)-1,2-Dimethyl-3,4-dioxoazetidine-2-carboxylic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (2S)-1,2-Dimethyl-3,4-dioxoazetidine-2-carboxylic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (2S)-1,2-Dimethyl-3,4-dioxoazetidine-2-carboxylic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID57373334
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound67288555
PDB IDNot Available
ChEBI IDNot Available
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. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]