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Showing NP-Card for 2-Methylacetoacetic acid (NP0087080)

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Record Information
Version1.0
Created at2022-05-11 16:39:27 UTC
Updated at2022-05-11 16:39:28 UTC
NP-MRD IDNP0087080
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Methylacetoacetic acid
Description2-Methylacetoacetic acid, also known as 2-methyl-3-oxo-butyric acid, 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. Several isoenzymes are known, which can occur in the cytosol (ACAT2), the mitochondria (ACAT1) , or the peroxisomes(ACAA2). 2-Methylacetoacetic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Methylacetoacetic acid is a potentially toxic compound. Thiolases are ubiquitous and important enzymes. Mitochondrial acetoacetyl-coenzyme A (CoA) thiolase (T2) is important in the pathways for the synthesis and degradation of ketone bodies as well as for the degradation of 2-methylacetoacetyl-CoA. 2-Methylacetoacetic acid is a metabolite that has an increased excretion in patients with acetoacetyl-CoA thiolase (EC2.3.1.9) Deficiency (OMIM 607809 , ACAT1; OMIM 100678 , ACAT2; OMIM 604770 , ACAA2; OMIM 607809 ). Thiolases are CoA-dependent enzymes which catalyze the formation of a carbon-carbon bond in a Claisen condensation step and its reverse reaction via a thiolytic degradation mechanism.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0087080 (2-Methylacetoacetic acid)


  Mrv1652305171803392D          

  8  7  0  0  0  0            999 V2000
    2.0625    0.7145    0.0000 C   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    2.1434    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
    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  0  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  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  2  6  1  0  0  0  0
  6  7  2  0  0  0  0
  8  6  1  0  0  0  0
M  END
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3D MOL for NP0087080 (2-Methylacetoacetic acid)

     RDKit          3D

 16 15  0  0  0  0  0  0  0  0999 V2000
   -2.1729   -0.2455    0.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7875   -0.7633   -0.0537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5638   -1.8469   -0.5087 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3287    0.0879    0.4217 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3777    1.3958   -0.3435 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6223   -0.6120    0.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2506   -0.8899    1.5050 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2119   -1.0009   -0.7583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7348   -0.7786    0.8516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2045    0.8361    0.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7509   -0.3865   -0.8876 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992    0.3625    1.4888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2797    1.3176   -1.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4012    1.6104   -0.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0377    2.2570    0.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1647   -1.3438   -0.8154 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  4  6  1  0
  6  8  1  0
  6  7  2  0
  5 13  1  0
  5 14  1  0
  5 15  1  0
  4 12  1  1
  1  9  1  0
  1 10  1  0
  1 11  1  0
  8 16  1  0
M  END
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3D SDF for NP0087080 (2-Methylacetoacetic acid)


  Mrv1652305171803392D          

  8  7  0  0  0  0            999 V2000
    2.0625    0.7145    0.0000 C   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    2.1434    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
    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  0  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  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  2  6  1  0  0  0  0
  6  7  2  0  0  0  0
  8  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0087080

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H8O3/c1-3(4(2)6)5(7)8/h3H,1-2H3,(H,7,8)

> <INCHI_KEY>
GCXJINGJZAOJHR-UHFFFAOYSA-N

> <FORMULA>
C5H8O3

> <MOLECULAR_WEIGHT>
116.1152

> <EXACT_MASS>
116.047344122

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
11.087058497494908

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methyl-3-oxobutanoic acid

> <ALOGPS_LOGP>
0.20

> <JCHEM_LOGP>
0.5414945326666666

> <ALOGPS_LOGS>
-0.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.76251789577401

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.174423632224775

> <JCHEM_PKA_STRONGEST_BASIC>
-7.532727734312502

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
27.1134

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.49e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetopropionic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0087080 (2-Methylacetoacetic acid)

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PDB for NP0087080 (2-Methylacetoacetic acid)
HEADER    PROTEIN                                 17-MAY-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-MAY-18         0                                  
HETATM    1  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.310   4.001   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.000   2.667   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    2    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END

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3D PDB for NP0087080 (2-Methylacetoacetic acid)
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SMILES for NP0087080 (2-Methylacetoacetic acid)
CC(C(C)=O)C(O)=O
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INCHI for NP0087080 (2-Methylacetoacetic acid)
InChI=1S/C5H8O3/c1-3(4(2)6)5(7)8/h3H,1-2H3,(H,7,8)
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View in JSmol
Synonyms
ValueSource
2-Methyl-3-oxo-butyric acidChEBI
2-Methyl-3-oxo-butyrateGenerator
2-MethylacetoacetateGenerator
(+/-)-2-methyl-3-oxobutanoateHMDB
(+/-)-2-methyl-3-oxobutanoic acidHMDB
2-Acetylpropionic acidHMDB
2-Methyl-3-ketobutyric acidHMDB
2-Methyl-3-oxo-butanoateHMDB
2-Methyl-3-oxo-butanoic acidHMDB
2-Methyl-3-oxobutanoateHMDB
2-Methyl-3-oxobutanoic acidHMDB
2-Methyl-3-oxobutyric acidHMDB
2-Methyl-acetoacetic acidHMDB
3-oxo-2-Methylbutyric acidHMDB
a-Methylacetoacetic acidHMDB
alpha-MethylacetoacetateHMDB, MeSH
alpha-Methylacetoacetic acidHMDB
2Methyl-3-ketovalerateGenerator, HMDB
2-Methylacetoacetic acidMeSH
Chemical FormulaC5H8O3
Average Mass116.1152 Da
Monoisotopic Mass116.04734 Da
IUPAC Name2-methyl-3-oxobutanoic acid
Traditional Nameacetopropionic acid
CAS Registry NumberNot Available
SMILES
CC(C(C)=O)C(O)=O
InChI Identifier
InChI=1S/C5H8O3/c1-3(4(2)6)5(7)8/h3H,1-2H3,(H,7,8)
InChI KeyGCXJINGJZAOJHR-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
  • Beta-keto acid
    • 

  • Branched fatty acid
    • 

  • Methyl-branched fatty acid
    • 

  • Short-chain keto acid
    • 

  • Beta-hydroxy ketone
    • 

  • Fatty acyl
    • 

  • 1,3-dicarbonyl compound
    • 

  • Ketone
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Organic oxide
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.2ALOGPS
logP0.54ChemAxon
logS-0.09ALOGPS
pKa (Strongest Acidic)4.17ChemAxon
pKa (Strongest Basic)-7.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity27.11 m³·mol⁻¹ChemAxon
Polarizability11.09 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0029172  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023226  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound150996  
PDB IDNot Available
ChEBI ID37079  
Good Scents IDNot Available
References
General ReferencesNot Available