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Showing NP-Card for 2-acetyllactic acid (NP0255567)

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Record Information
Version2.0
Created at2022-09-07 20:06:48 UTC
Updated at2022-09-07 20:06:48 UTC
NP-MRD IDNP0255567
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-acetyllactic acid
Description2-Acetolactate 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. 2-Acetolactate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Acetolactate exists in all living species, ranging from bacteria to humans. 2-acetyllactic acid is found in Trypanosoma brucei. In the butanoate metabolism pathway, 2-Acetolactate is created from 2-(alpha-Hydroxyethyl)thiamine diphosphate by acetolactate synthase.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0255567 (2-acetyllactic acid)

 
  Mrv0541 02231220532D          
 
  9  8  0  0  0  0            999 V2000
   12.8398   -9.6468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5093   -9.1512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8398  -10.4715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1249   -9.2345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6379  -10.1197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5093   -8.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2205   -9.5635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1249  -10.8801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5927  -10.9217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  0  0  0  0
  2  6  1  0  0  0  0
  2  7  2  0  0  0  0
  3  8  1  0  0  0  0
  3  9  2  0  0  0  0
M  END
Download

3D MOL for NP0255567 (2-acetyllactic acid)

     RDKit          3D

 17 16  0  0  0  0  0  0  0  0999 V2000
    2.1276   -0.4138    0.4270 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6976   -0.1597    0.6368 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2471   -0.2479    1.7675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2656    0.2035   -0.4375 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3275   -0.8925   -0.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3437    0.2782   -1.6835 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9524    1.4663   -0.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9256    2.4074   -0.9334 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6278    1.6265    1.0632 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6925    0.0439    1.2860 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3847   -1.4951    0.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4959    0.1061   -0.4850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9367   -1.8393   -0.8144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1861   -0.5161   -1.0277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6314   -1.0227    0.6272 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0209   -0.4372   -1.8133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1567    0.8923    1.5330 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  1  6
  4  7  1  0
  7  9  1  0
  7  8  2  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  5 13  1  0
  5 14  1  0
  5 15  1  0
  6 16  1  0
  9 17  1  0
M  END
Download

3D SDF for NP0255567 (2-acetyllactic acid)

 
  Mrv0541 02231220532D          
 
  9  8  0  0  0  0            999 V2000
   12.8398   -9.6468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5093   -9.1512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8398  -10.4715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1249   -9.2345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6379  -10.1197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5093   -8.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2205   -9.5635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1249  -10.8801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5927  -10.9217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  0  0  0  0
  2  6  1  0  0  0  0
  2  7  2  0  0  0  0
  3  8  1  0  0  0  0
  3  9  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0255567

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H8O4/c1-3(6)5(2,9)4(7)8/h9H,1-2H3,(H,7,8)

> <INCHI_KEY>
NMDWGEGFJUBKLB-UHFFFAOYSA-N

> <FORMULA>
C5H8O4

> <MOLECULAR_WEIGHT>
132.1146

> <EXACT_MASS>
132.042258744

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
11.81763978867469

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.65

> <JCHEM_LOGP>
-0.2838843203333333

> <ALOGPS_LOGS>
0.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.416069462259802

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4493929439633346

> <JCHEM_PKA_STRONGEST_BASIC>
-4.591623143588905

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
28.590400000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.86e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-acetyllactic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0255567 (2-acetyllactic acid)

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PDB for NP0255567 (2-acetyllactic acid)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      23.968 -18.007   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      25.217 -17.082   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      23.968 -19.547   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      22.633 -17.238   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      25.457 -18.890   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      25.217 -15.550   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      26.545 -17.852   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      22.633 -20.310   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      25.373 -20.387   0.000  0.00  0.00           O+0
CONECT    1    2    3    4    5                                             
CONECT    2    1    6    7                                                  
CONECT    3    1    8    9                                                  
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    2                                                            
CONECT    7    2                                                            
CONECT    8    3                                                            
CONECT    9    3                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END

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3D PDB for NP0255567 (2-acetyllactic acid)
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SMILES for NP0255567 (2-acetyllactic acid)
CC(=O)C(C)(O)C(O)=O
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INCHI for NP0255567 (2-acetyllactic acid)
InChI=1S/C5H8O4/c1-3(6)5(2,9)4(7)8/h9H,1-2H3,(H,7,8)
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View in JSmol
Synonyms
ValueSource
2-Acetolactic acidGenerator
2-AcetolactateChEBI
Chemical FormulaC5H8O4
Average Mass132.1146 Da
Monoisotopic Mass132.04226 Da
IUPAC Name2-hydroxy-2-methyl-3-oxobutanoic acid
Traditional Name2-acetyllactic acid
CAS Registry NumberNot Available
SMILES
CC(=O)C(C)(O)C(O)=O
InChI Identifier
InChI=1S/C5H8O4/c1-3(6)5(2,9)4(7)8/h9H,1-2H3,(H,7,8)
InChI KeyNMDWGEGFJUBKLB-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Trypanosoma bruceiLOTUS Database
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
    • 

  • Hydroxy fatty acid
    • 

  • Short-chain keto acid
    • 

  • Methyl-branched fatty acid
    • 

  • Alpha-hydroxy acid
    • 

  • Fatty acyl
    • 

  • Acyloin
    • 

  • Beta-hydroxy ketone
    • 

  • Hydroxy acid
    • 

  • Tertiary alcohol
    • 

  • Alpha-hydroxy ketone
    • 

  • Ketone
    • 

  • Carboxylic acid derivative
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carbonyl group
    • 

  • Alcohol
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • 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
logP-0.65ALOGPS
logP-0.28ChemAxon
logS0.33ALOGPS
pKa (Strongest Acidic)3.45ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity28.59 m³·mol⁻¹ChemAxon
Polarizability11.82 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0006833  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB024109  
KNApSAcK IDC00019658  
Chemspider IDNot Available
KEGG Compound IDC00900  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAcetolactic acid  
METLIN IDNot Available
PubChem Compound22  
PDB IDNot Available
ChEBI ID16444  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]