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Showing metabocard for acetoacetate (HMDB0304256)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-24 08:24:17 UTC
Update Date2021-09-24 08:24:17 UTC
HMDB IDHMDB0304256
Secondary Accession NumbersNone
Metabolite Identification
Common Nameacetoacetate
DescriptionAcetoacetate, also known as acetoacetic acid or oxobutyrate, belongs to short-chain keto acids and derivatives class of compounds. Those are keto acids with an alkyl chain the contains less than 6 carbon atoms. Acetoacetate is soluble (in water) and a weakly acidic compound (based on its pKa). Acetoacetate can be found in a number of food items such as plains prickly pear, daikon radish, papaya, and common chokecherry, which makes acetoacetate a potential biomarker for the consumption of these food products. Acetoacetic acid (also diacetic acid) is the organic compound with the formula CH3COCH2COOH. It is the simplest beta-keto acid group, and like other members of this class, it is unstable. The methyl and ethyl esters, which are quite stable, are produced on a large scale industrially as precursors to dyes. Acetoacetic acid is a weak acid .
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0304256 (acetoacetate)


  Mrv1533005141521412D          

  7  6  0  0  0  0            999 V2000
    1.2375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    1.4289    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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
M  CHG  1   6  -1
M  END
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3D MOL for HMDB0304256 (acetoacetate)

HMDB0304256
     RDKit          3D
acetoacetate
 12 11  0  0  0  0  0  0  0  0999 V2000
   -1.5049    0.5731    0.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5928   -0.4258   -0.4599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8934   -0.9552   -1.5145 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6970   -0.8182    0.1479 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6843    0.3052    0.0597 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8401    0.0460    0.4934 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3672    1.5496   -0.4595 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.2433    1.6137   -0.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5329    0.3976   -0.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5584    0.5246    1.2570 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1388   -1.6354   -0.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5984   -1.1752    1.2116 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
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  4 11  1  0
  4 12  1  0
M  CHG  1   7  -1
M  END
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3D SDF for HMDB0304256 (acetoacetate)


  Mrv1533005141521412D          

  7  6  0  0  0  0            999 V2000
    1.2375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    1.4289    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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
M  CHG  1   6  -1
M  END
> <DATABASE_ID>
HMDB0304256

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)CC([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H6O3/c1-3(5)2-4(6)7/h2H2,1H3,(H,6,7)/p-1

> <INCHI_KEY>
WDJHALXBUFZDSR-UHFFFAOYSA-M

> <FORMULA>
C4H5O3

> <MOLECULAR_WEIGHT>
101.082

> <EXACT_MASS>
101.024417601

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
8.78250785025398

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-oxobutanoate

> <ALOGPS_LOGP>
-0.50

> <JCHEM_LOGP>
-0.0014917456666668494

> <ALOGPS_LOGS>
0.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.223356862546826

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.024917062647246

> <JCHEM_PKA_STRONGEST_BASIC>
-7.473176600242656

> <JCHEM_POLAR_SURFACE_AREA>
57.199999999999996

> <JCHEM_REFRACTIVITY>
33.376000000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.49e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetoacetate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0304256 (acetoacetate)

HMDB0304256
     RDKit          3D
acetoacetate
 12 11  0  0  0  0  0  0  0  0999 V2000
   -1.5049    0.5731    0.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5928   -0.4258   -0.4599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8934   -0.9552   -1.5145 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6970   -0.8182    0.1479 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6843    0.3052    0.0597 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8401    0.0460    0.4934 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3672    1.5496   -0.4595 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.2433    1.6137   -0.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5329    0.3976   -0.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5584    0.5246    1.2570 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1388   -1.6354   -0.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5984   -1.1752    1.2116 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
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  4 11  1  0
  4 12  1  0
M  CHG  1   7  -1
M  END
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PDB for HMDB0304256 (acetoacetate)

HEADER    PROTEIN                                 14-MAY-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-MAY-15         0                                  
HETATM    1  C   UNK     0       2.310   4.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.000   2.667   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O-1
HETATM    7  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    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 HMDB0304256 (acetoacetate)

COMPND    HMDB0304256
HETATM    1  C1  UNL     1      -1.505   0.573   0.175  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.593  -0.426  -0.460  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.893  -0.955  -1.515  1.00  0.00           O  
HETATM    4  C3  UNL     1       0.697  -0.818   0.148  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.684   0.305   0.060  1.00  0.00           C  
HETATM    6  O2  UNL     1       2.840   0.046   0.493  1.00  0.00           O  
HETATM    7  O3  UNL     1       1.367   1.550  -0.459  1.00  0.00           O1-
HETATM    8  H1  UNL     1      -1.243   1.614  -0.190  1.00  0.00           H  
HETATM    9  H2  UNL     1      -2.533   0.398  -0.218  1.00  0.00           H  
HETATM   10  H3  UNL     1      -1.558   0.525   1.257  1.00  0.00           H  
HETATM   11  H4  UNL     1       1.139  -1.635  -0.503  1.00  0.00           H  
HETATM   12  H5  UNL     1       0.598  -1.175   1.212  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3    3    4
CONECT    4    5   11   12
CONECT    5    6    6    7
END
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SMILES for HMDB0304256 (acetoacetate)

CC(=O)CC([O-])=O
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INCHI for HMDB0304256 (acetoacetate)

InChI=1S/C4H6O3/c1-3(5)2-4(6)7/h2H2,1H3,(H,6,7)/p-1
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View in JSmolView Stereo Labels
Synonyms
ValueSource
Acetoacetate ion(1-)ChEBI
Butanoic acid, 3-oxo-, ion(1-)ChEBI
Acetoacetic acid ion(1-)Generator
Butanoate, 3-oxo-, ion(1-)Generator
Acetoacetic acidGenerator
Acetoacetic acid, lithium saltMeSH
Sodium acetoacetateMeSH
3-KetobutyrateMeSH
Acetoacetic acid, calcium saltMeSH
OxobutyrateMeSH
3-Oxobutyric acidMeSH
Acetoacetic acid, sodium saltMeSH
Chemical FormulaC4H5O3
Average Molecular Weight101.082
Monoisotopic Molecular Weight101.024417601
IUPAC Name3-oxobutanoate
Traditional Nameacetoacetate
CAS Registry NumberNot Available
SMILES
CC(=O)CC([O-])=O
InChI Identifier
InChI=1S/C4H6O3/c1-3(5)2-4(6)7/h2H2,1H3,(H,6,7)/p-1
InChI KeyWDJHALXBUFZDSR-UHFFFAOYSA-M
Chemical Taxonomy
Description Belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassShort-chain keto acids and derivatives
Direct ParentShort-chain keto acids and derivatives
Alternative Parents
Substituents
  • Short-chain keto acid
  • Beta-keto acid
  • 1,3-dicarbonyl compound
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Organic anion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Source
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
logP-0.5ALOGPS
logP-0.0015ChemAxon
logS0.47ALOGPS
pKa (Strongest Acidic)4.02ChemAxon
pKa (Strongest Basic)-7.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area57.2 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity33.38 m³·mol⁻¹ChemAxon
Polarizability8.78 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
AllCCS[M+H]+124.77532859911
AllCCS[M+H-H2O]+120.37632859911
AllCCS[M+Na]+130.06732859911
AllCCS[M+NH4]+128.88132859911
AllCCS[M-H]-119.53132859911
AllCCS[M+Na-2H]-123.30732859911
AllCCS[M+HCOO]-127.4732859911
DeepCCS[M+H]+131.73130932474
DeepCCS[M-H]-128.96130932474
DeepCCS[M-2H]-165.81930932474
DeepCCS[M+Na]+140.36530932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
acetoacetate,1TMS,isomer #1CC(=CC(=O)[O-])O[Si](C)(C)C1046.8Semi standard non polar33892256
acetoacetate,1TMS,isomer #1CC(=CC(=O)[O-])O[Si](C)(C)C977.6Standard non polar33892256
acetoacetate,1TMS,isomer #1CC(=CC(=O)[O-])O[Si](C)(C)C1275.9Standard polar33892256
acetoacetate,1TMS,isomer #2C=C(CC(=O)[O-])O[Si](C)(C)C993.7Semi standard non polar33892256
acetoacetate,1TMS,isomer #2C=C(CC(=O)[O-])O[Si](C)(C)C982.1Standard non polar33892256
acetoacetate,1TMS,isomer #2C=C(CC(=O)[O-])O[Si](C)(C)C1261.5Standard polar33892256
acetoacetate,1TBDMS,isomer #1CC(=CC(=O)[O-])O[Si](C)(C)C(C)(C)C1274.6Semi standard non polar33892256
acetoacetate,1TBDMS,isomer #1CC(=CC(=O)[O-])O[Si](C)(C)C(C)(C)C1172.5Standard non polar33892256
acetoacetate,1TBDMS,isomer #1CC(=CC(=O)[O-])O[Si](C)(C)C(C)(C)C1436.5Standard polar33892256
acetoacetate,1TBDMS,isomer #2C=C(CC(=O)[O-])O[Si](C)(C)C(C)(C)C1190.7Semi standard non polar33892256
acetoacetate,1TBDMS,isomer #2C=C(CC(=O)[O-])O[Si](C)(C)C(C)(C)C1177.6Standard non polar33892256
acetoacetate,1TBDMS,isomer #2C=C(CC(=O)[O-])O[Si](C)(C)C(C)(C)C1427.2Standard polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - acetoacetate 10V, Positive-QTOFsplash10-0udr-7900000000-89b2e3830a8a06a2e37a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - acetoacetate 20V, Positive-QTOFsplash10-0udr-9400000000-9c5ed4c05378002a816f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - acetoacetate 40V, Positive-QTOFsplash10-00dl-9000000000-5a73f1085adb822540de2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - acetoacetate 10V, Negative-QTOFsplash10-0zfr-8900000000-f57e425bf957e0370f162016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - acetoacetate 20V, Negative-QTOFsplash10-0a4i-9200000000-adbf3b18584991c67b722016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - acetoacetate 40V, Negative-QTOFsplash10-0a4i-9000000000-20c62cb1ee0c3a49eaca2016-08-03Wishart LabView Spectrum
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 IDFDB030645
KNApSAcK IDNot Available
Chemspider ID5341896
KEGG Compound IDNot Available
BioCyc ID3-KETOBUTYRATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6971017
PDB IDNot Available
ChEBI ID13705
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