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Showing metabocard for Methylacetoacetic acid (HMDB0000310)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:42 UTC
HMDB IDHMDB0000310
Secondary Accession Numbers
  • HMDB00310
Metabolite Identification
Common NameMethylacetoacetic acid
DescriptionMethylacetoacetic acid, also known as 3-oxo-butanoate or methyl acetylacetate, belongs to the class of organic compounds known as beta-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C3 carbon atom. Methylacetoacetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Methylacetoacetic acid is a citrus, fresh, and fruity tasting compound. Methylacetoacetic acid has been identified in the urine of patients with an inherited deficiency of propionyl-CoA carboxylase (PMID 630060 ), and after isoleucine loading in the diagnosis of 2-methylacetoacetyl-CoA thiolase deficiency.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000310 (Methylacetoacetic acid)

  Mrv1652305271900212D          

  8  7  0  0  0  0            999 V2000
   12.3155  -12.6331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0301  -13.8707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4590  -13.8707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7445  -12.6331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6010  -13.0456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1734  -12.6331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0301  -13.0456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4590  -13.0456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1  7  1  0  0  0  0
  2  7  2  0  0  0  0
  3  8  2  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  6  8  1  0  0  0  0
M  END
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3D MOL for HMDB0000310 (Methylacetoacetic acid)

HMDB0000310
     RDKit          3D
Methylacetoacetic acid
 16 15  0  0  0  0  0  0  0  0999 V2000
    3.2553    0.1106   -0.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9970   -0.0975   -0.7506 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8126    0.0373   -0.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9405    0.3588    1.1844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5233   -0.1820   -0.6533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5597    0.0419    0.3837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0153   -0.0964    0.0959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2668    0.3538    1.5356 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1239    0.5052    0.8725 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8206    0.8881   -0.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8453   -0.8279   -0.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6154   -1.2382   -1.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6770    0.4603   -1.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5262    0.8539    0.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2203   -0.2455   -0.9789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3911   -0.9225    0.7242 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  1  0
  6  7  1  0
  6  8  2  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  5 12  1  0
  5 13  1  0
  7 14  1  0
  7 15  1  0
  7 16  1  0
M  END
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3D SDF for HMDB0000310 (Methylacetoacetic acid)

  Mrv1652305271900212D          

  8  7  0  0  0  0            999 V2000
   12.3155  -12.6331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0301  -13.8707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4590  -13.8707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7445  -12.6331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6010  -13.0456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1734  -12.6331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0301  -13.0456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4590  -13.0456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1  7  1  0  0  0  0
  2  7  2  0  0  0  0
  3  8  2  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  6  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000310

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)CC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H8O3/c1-4(6)3-5(7)8-2/h3H2,1-2H3

> <INCHI_KEY>
WRQNANDWMGAFTP-UHFFFAOYSA-N

> <FORMULA>
C5H8O3

> <MOLECULAR_WEIGHT>
116.1152

> <EXACT_MASS>
116.047344122

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
11.268351836130842

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 3-oxobutanoate

> <ALOGPS_LOGP>
-0.29

> <JCHEM_LOGP>
0.14440231033333323

> <ALOGPS_LOGS>
0.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.277379621268754

> <JCHEM_PKA_STRONGEST_BASIC>
-6.953947588641049

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
27.308

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.37e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl acetoacetate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0000310 (Methylacetoacetic acid)

HMDB0000310
     RDKit          3D
Methylacetoacetic acid
 16 15  0  0  0  0  0  0  0  0999 V2000
    3.2553    0.1106   -0.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9970   -0.0975   -0.7506 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8126    0.0373   -0.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9405    0.3588    1.1844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5233   -0.1820   -0.6533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5597    0.0419    0.3837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0153   -0.0964    0.0959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2668    0.3538    1.5356 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1239    0.5052    0.8725 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8206    0.8881   -0.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8453   -0.8279   -0.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6154   -1.2382   -1.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6770    0.4603   -1.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5262    0.8539    0.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2203   -0.2455   -0.9789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3911   -0.9225    0.7242 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  1  0
  6  7  1  0
  6  8  2  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  5 12  1  0
  5 13  1  0
  7 14  1  0
  7 15  1  0
  7 16  1  0
M  END
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PDB for HMDB0000310 (Methylacetoacetic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      22.989 -23.582   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      24.323 -25.892   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      26.990 -25.892   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      25.656 -23.582   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.655 -24.352   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.324 -23.582   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      24.323 -24.352   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      26.990 -24.352   0.000  0.00  0.00           C+0
CONECT    1    5    7                                                       
CONECT    2    7                                                            
CONECT    3    8                                                            
CONECT    4    7    8                                                       
CONECT    5    1                                                            
CONECT    6    8                                                            
CONECT    7    1    2    4                                                  
CONECT    8    3    4    6                                                  
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
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3D PDB for HMDB0000310 (Methylacetoacetic acid)

COMPND    HMDB0000310
HETATM    1  C1  UNL     1       3.255   0.111  -0.160  1.00  0.00           C  
HETATM    2  O1  UNL     1       1.997  -0.098  -0.751  1.00  0.00           O  
HETATM    3  C2  UNL     1       0.813   0.037  -0.033  1.00  0.00           C  
HETATM    4  O2  UNL     1       0.940   0.359   1.184  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.523  -0.182  -0.653  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.560   0.042   0.384  1.00  0.00           C  
HETATM    7  C5  UNL     1      -3.015  -0.096   0.096  1.00  0.00           C  
HETATM    8  O3  UNL     1      -1.267   0.354   1.536  1.00  0.00           O  
HETATM    9  H1  UNL     1       3.124   0.505   0.872  1.00  0.00           H  
HETATM   10  H2  UNL     1       3.821   0.888  -0.727  1.00  0.00           H  
HETATM   11  H3  UNL     1       3.845  -0.828  -0.045  1.00  0.00           H  
HETATM   12  H4  UNL     1      -0.615  -1.238  -1.015  1.00  0.00           H  
HETATM   13  H5  UNL     1      -0.677   0.460  -1.552  1.00  0.00           H  
HETATM   14  H6  UNL     1      -3.526   0.854   0.410  1.00  0.00           H  
HETATM   15  H7  UNL     1      -3.220  -0.245  -0.979  1.00  0.00           H  
HETATM   16  H8  UNL     1      -3.391  -0.922   0.724  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6   12   13
CONECT    6    7    8    8
CONECT    7   14   15   16
END
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SMILES for HMDB0000310 (Methylacetoacetic acid)

COC(=O)CC(C)=O
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INCHI for HMDB0000310 (Methylacetoacetic acid)

InChI=1S/C5H8O3/c1-4(6)3-5(7)8-2/h3H2,1-2H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC5H8O3
Average Molecular Weight116.1152
Monoisotopic Molecular Weight116.047344122
IUPAC Namemethyl 3-oxobutanoate
Traditional Namemethyl acetoacetate
CAS Registry Number105-45-3
SMILES
COC(=O)CC(C)=O
InChI Identifier
InChI=1S/C5H8O3/c1-4(6)3-5(7)8-2/h3H2,1-2H3
InChI KeyWRQNANDWMGAFTP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as beta-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C3 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassBeta-keto acids and derivatives
Direct ParentBeta-keto acids and derivatives
Alternative Parents
Substituents
  • Beta-keto acid
  • Fatty acid ester
  • Fatty acid methyl ester
  • 1,3-dicarbonyl compound
  • Fatty acyl
  • Methyl ester
  • Carboxylic acid ester
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Organoleptic effect
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-80 °CNot Available
Boiling Point169.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility500 mg/mLNot Available
LogP0.185 (est)The Good Scents Company Information System
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 IDFDB021937
KNApSAcK IDNot Available
Chemspider ID13874867
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5299
PubChem Compound7757
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1014971
References
Synthesis ReferenceChan, Tak-Hang; Brownbridge, Peter. Reaction of electrophiles with 1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene, a dianion equivalent of methyl acetoacetate. Journal of the Chemical Society, Chemical Communications (1979), (13), 578-9.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Robinson BH, Sherwood WG, Taylor J, Balfe JW, Mamer OA: Acetoacetyl CoA thiolase deficiency: a cause of severe ketoacidosis in infancy simulating salicylism. J Pediatr. 1979 Aug;95(2):228-33. [PubMed:36452 ]
  2. Aramaki S, Lehotay D, Sweetman L, Nyhan WL, Winter SC, Middleton B: Urinary excretion of 2-methylacetoacetate, 2-methyl-3-hydroxybutyrate and tiglylglycine after isoleucine loading in the diagnosis of 2-methylacetoacetyl-CoA thiolase deficiency. J Inherit Metab Dis. 1991;14(1):63-74. [PubMed:1861461 ]
  3. Sweetman L, Weyler W, Nyhan WL, de Cespedes C, Loria AR, Estrada Y: Abnormal metabolites of isoleucine in a patient with propionyl-CoA carboxylase deficiency. Biomed Mass Spectrom. 1978 Mar;5(3):198-207. [PubMed:630060 ]