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Showing metabocard for 2,3-Butanedione monoxime (HMDB0245382)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-10 22:27:26 UTC
Update Date2021-09-26 22:53:49 UTC
HMDB IDHMDB0245382
Secondary Accession NumbersNone
Metabolite Identification
Common Name2,3-Butanedione monoxime
Description2,3-Butanedione monoxime, also known as diacetyl monooxime or 2,3-bdmo, belongs to the class of organic compounds known as ketoximes. These are organic compounds with the general formula RC(R')=NOH (R,R' = organyl). Based on a literature review very few articles have been published on 2,3-Butanedione monoxime. This compound has been identified in human blood as reported by (PMID: 31557052 ). 2,3-butanedione monoxime is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2,3-Butanedione monoxime 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 HMDB0245382 (2,3-Butanedione monoxime)


  Mrv1652309112100272D          

  7  6  0  0  0  0            999 V2000
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  4  0  0  0
  2  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
M  END
Download

3D MOL for HMDB0245382 (2,3-Butanedione monoxime)

HMDB0245382
     RDKit          3D
2,3-Butanedione monoxime
 14 13  0  0  0  0  0  0  0  0999 V2000
    2.1733    0.0085   -0.4285 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9395   -0.7353   -0.0812 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0223   -1.9526    0.1968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3467   -0.0589   -0.0643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6095   -0.7637    0.2777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4391    1.1958   -0.3498 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6088    1.8842   -0.3519 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3803    0.7605    0.3719 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0673    0.5149   -1.4316 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0393   -0.6545   -0.5125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1404   -0.2270    1.1101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3524   -1.7630    0.6864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2790   -0.8635   -0.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8462    2.6546    0.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  4  6  2  3
  6  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  5 11  1  0
  5 12  1  0
  5 13  1  0
  7 14  1  0
M  END
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3D SDF for HMDB0245382 (2,3-Butanedione monoxime)


  Mrv1652309112100272D          

  7  6  0  0  0  0            999 V2000
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  4  0  0  0
  2  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0245382

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)C(C)=NO

> <INCHI_IDENTIFIER>
InChI=1S/C4H7NO2/c1-3(5-7)4(2)6/h7H,1-2H3

> <INCHI_KEY>
FSEUPUDHEBLWJY-UHFFFAOYSA-N

> <FORMULA>
C4H7NO2

> <MOLECULAR_WEIGHT>
101.105

> <EXACT_MASS>
101.047678469

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
9.818542535927602

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(hydroxyimino)butan-2-one

> <ALOGPS_LOGP>
0.11

> <JCHEM_LOGP>
0.404979262

> <ALOGPS_LOGS>
-0.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.504974831235494

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5444876021343629

> <JCHEM_POLAR_SURFACE_AREA>
49.660000000000004

> <JCHEM_REFRACTIVITY>
25.362500000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,3-butanedione monoxime

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0245382 (2,3-Butanedione monoxime)

HMDB0245382
     RDKit          3D
2,3-Butanedione monoxime
 14 13  0  0  0  0  0  0  0  0999 V2000
    2.1733    0.0085   -0.4285 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9395   -0.7353   -0.0812 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0223   -1.9526    0.1968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3467   -0.0589   -0.0643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6095   -0.7637    0.2777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4391    1.1958   -0.3498 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6088    1.8842   -0.3519 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3803    0.7605    0.3719 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0673    0.5149   -1.4316 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0393   -0.6545   -0.5125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1404   -0.2270    1.1101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3524   -1.7630    0.6864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2790   -0.8635   -0.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8462    2.6546    0.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  4  6  2  3
  6  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  5 11  1  0
  5 12  1  0
  5 13  1  0
  7 14  1  0
M  END
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PDB for HMDB0245382 (2,3-Butanedione monoxime)

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       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    4  O   UNK     0      -0.770  -1.334   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.540   2.667   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for HMDB0245382 (2,3-Butanedione monoxime)

COMPND    HMDB0245382
HETATM    1  C1  UNL     1       2.173   0.008  -0.428  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.940  -0.735  -0.081  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.022  -1.953   0.197  1.00  0.00           O  
HETATM    4  C3  UNL     1      -0.347  -0.059  -0.064  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.609  -0.764   0.278  1.00  0.00           C  
HETATM    6  N1  UNL     1      -0.439   1.196  -0.350  1.00  0.00           N  
HETATM    7  O2  UNL     1      -1.609   1.884  -0.352  1.00  0.00           O  
HETATM    8  H1  UNL     1       2.380   0.761   0.372  1.00  0.00           H  
HETATM    9  H2  UNL     1       2.067   0.515  -1.432  1.00  0.00           H  
HETATM   10  H3  UNL     1       3.039  -0.655  -0.513  1.00  0.00           H  
HETATM   11  H4  UNL     1      -2.140  -0.227   1.110  1.00  0.00           H  
HETATM   12  H5  UNL     1      -1.352  -1.763   0.686  1.00  0.00           H  
HETATM   13  H6  UNL     1      -2.279  -0.864  -0.594  1.00  0.00           H  
HETATM   14  H7  UNL     1      -1.846   2.655   0.221  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3    3    4
CONECT    4    5    6    6
CONECT    5   11   12   13
CONECT    6    7
CONECT    7   14
END
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SMILES for HMDB0245382 (2,3-Butanedione monoxime)

CC(=O)C(C)=NO
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INCHI for HMDB0245382 (2,3-Butanedione monoxime)

InChI=1S/C4H7NO2/c1-3(5-7)4(2)6/h7H,1-2H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
2,3-BDMOHMDB
2,3-Butanedione monooximeHMDB
KBDOHMDB
Butanedione monoximeHMDB
Diacetyl monooximeHMDB
Diacetyl monoximeHMDB
DiacetylmonoximeHMDB
Potassium 2,3-butanedione monoximateHMDB
Chemical FormulaC4H7NO2
Average Molecular Weight101.105
Monoisotopic Molecular Weight101.047678469
IUPAC Name3-(hydroxyimino)butan-2-one
Traditional Name2,3-butanedione monoxime
CAS Registry NumberNot Available
SMILES
CC(=O)C(C)=NO
InChI Identifier
InChI=1S/C4H7NO2/c1-3(5-7)4(2)6/h7H,1-2H3
InChI KeyFSEUPUDHEBLWJY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ketoximes. These are organic compounds with the general formula RC(R')=NOH (R,R' = organyl).
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassOximes
Direct ParentKetoximes
Alternative Parents
Substituents
  • Ketoxime
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological location
ProcessNot Available
RoleNot 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
logP0.11ALOGPS
logP0.4ChemAxon
logS-0.99ALOGPS
pKa (Strongest Acidic)6.5ChemAxon
pKa (Strongest Basic)-0.54ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.66 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity25.36 m³·mol⁻¹ChemAxon
Polarizability9.82 ųChemAxon
Number of Rings0ChemAxon
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]+121.01730932474
DeepCCS[M-H]-118.58730932474
DeepCCS[M-2H]-154.89530932474
DeepCCS[M+Na]+129.48530932474
AllCCS[M+H]+125.932859911
AllCCS[M+H-H2O]+121.632859911
AllCCS[M+NH4]+129.932859911
AllCCS[M+Na]+131.132859911
AllCCS[M-H]-123.632859911
AllCCS[M+Na-2H]-127.532859911
AllCCS[M+HCOO]-131.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2,3-Butanedione monoximeCC(=O)C(C)=NO1287.7Standard polar33892256
2,3-Butanedione monoximeCC(=O)C(C)=NO982.7Standard non polar33892256
2,3-Butanedione monoximeCC(=O)C(C)=NO894.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2,3-Butanedione monoxime,1TMS,isomer #1C=C(O[Si](C)(C)C)C(C)=NO1104.4Semi standard non polar33892256
2,3-Butanedione monoxime,1TMS,isomer #1C=C(O[Si](C)(C)C)C(C)=NO1022.2Standard non polar33892256
2,3-Butanedione monoxime,1TMS,isomer #1C=C(O[Si](C)(C)C)C(C)=NO1769.1Standard polar33892256
2,3-Butanedione monoxime,1TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)C(C)=NO1304.3Semi standard non polar33892256
2,3-Butanedione monoxime,1TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)C(C)=NO1216.8Standard non polar33892256
2,3-Butanedione monoxime,1TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)C(C)=NO1890.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2,3-Butanedione monoxime GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9000000000-0ae61c80523b369f00122021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,3-Butanedione monoxime GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Butanedione monoxime 10V, Positive-QTOFsplash10-0006-9100000000-e8f7cf12225b5a16644a2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Butanedione monoxime 20V, Positive-QTOFsplash10-0006-9000000000-db15a804dc61430ea8f62021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Butanedione monoxime 40V, Positive-QTOFsplash10-0006-9000000000-39a1996b6efbc076acb12021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Butanedione monoxime 10V, Negative-QTOFsplash10-0udi-6900000000-321d395340f72b1826502021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Butanedione monoxime 20V, Negative-QTOFsplash10-014i-9200000000-12ffacc3ef4c64a9f7362021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Butanedione monoxime 40V, Negative-QTOFsplash10-0006-9000000000-f796ba68f1900cd9a85d2021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-10-12Wishart 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 ID4911363
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6398969
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 ]