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Showing NP-Card for Acetoacetate (NP0044224)

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Record Information
Version1.0
Created at2022-01-19 18:59:13 UTC
Updated at2022-01-19 19:00:44 UTC
NP-MRD IDNP0044224
Secondary Accession NumbersNone
Natural Product Identification
Common NameAcetoacetate
DescriptionAcetoacetate, also known as acetoacetic 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. A 3-oxo monocarboxylic acid anion that is the conjugate base of acetoacetic acid, arising from deprotonation of the carboxy group. Acetoacetate is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, acetoacetate is involved in phenylalanine and tyrosine metabolism. Outside of the human body, acetoacetate has been detected, but not quantified in, several different foods, such as cascade huckleberries, hazelnuts, cherimoya, adzuki beans, and broccoli. It was first documented in 2021 (PMID: 33857328). This could make acetoacetate a potential biomarker for the consumption of these foods.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0044224 (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 NP0044224 (Acetoacetate)

     RDKit          3D

 12 11  0  0  0  0  0  0  0  0999 V2000
   -1.6976    0.2168    0.3227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5616   -0.3119   -0.4801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7812   -0.5069   -1.6741 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7751   -0.5988    0.0946 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7496    0.4818   -0.1700 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4575    1.5162   -0.8118 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0374    0.3426    0.3124 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.4505    0.0619    1.4041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6662   -0.2471    0.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7454    1.3204    0.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1605   -1.5466   -0.3551 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7223   -0.7284    1.1936 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  7  1  0
  5  6  2  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 NP0044224 (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>
NP0044224

> <DATABASE_NAME>
NP-MRD

> <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 NP0044224 (Acetoacetate)

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PDB for NP0044224 (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 NP0044224 (Acetoacetate)
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SMILES for NP0044224 (Acetoacetate)
CC(=O)CC([O-])=O
Download
INCHI for NP0044224 (Acetoacetate)
InChI=1S/C4H6O3/c1-3(5)2-4(6)7/h2H2,1H3,(H,6,7)/p-1
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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 Mass101.0820 Da
Monoisotopic Mass101.02442 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-01-19View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, experimental)Ahselim2022-01-19View Spectrum
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 OriginNot Available
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
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
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
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030645  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc ID3-KETOBUTYRATE  
BiGG IDNot Available
Wikipedia LinkAcetoacetic acid  
METLIN IDNot Available
PubChem Compound6971017  
PDB IDNot Available
ChEBI ID13705  
Good Scents IDNot Available
References
General References
  1. Shaheen A: Can ketone bodies inactivate coronavirus spike protein? The potential of biocidal agents against SARS-CoV-2. Bioessays. 2021 Jun;43(6):e2000312. doi: 10.1002/bies.202000312. Epub 2021 Apr 15. [PubMed:33857328  ]