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Showing metabocard for 2-aceto-2-hydroxy-butanoate (HMDB0304056)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-24 06:46:54 UTC
Update Date2021-09-24 06:46:54 UTC
HMDB IDHMDB0304056
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-aceto-2-hydroxy-butanoate
Description 2-aceto-2-hydroxy-butanoate is soluble (in water) and a weakly acidic compound (based on its pKa). 2-aceto-2-hydroxy-butanoate can be found in a number of food items such as white cabbage, pistachio, pepper (c. frutescens), and yautia, which makes 2-aceto-2-hydroxy-butanoate a potential biomarker for the consumption of these food products.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0304056 (2-aceto-2-hydroxy-butanoate)


  Mrv1533005141512322D          

 10  9  0  0  0  0            999 V2000
    0.5230   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.1270    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
    1.6500   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.7145    0.0000 O   0  5  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 C   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  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
M  CHG  1   7  -1
M  END
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3D MOL for HMDB0304056 (2-aceto-2-hydroxy-butanoate)

HMDB0304056
     RDKit          3D
2-aceto-2-hydroxy-butanoate
 19 18  0  0  0  0  0  0  0  0999 V2000
   -1.2669   -1.1133    0.8650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2904   -0.2797   -0.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1488    0.7042   -0.4975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3893    1.3648   -1.7311 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1734    0.0169   -0.5847 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7671   -0.7511    0.5429 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7823    0.0973   -1.6310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1493    1.7354    0.5489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0591    1.4310    1.7367 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3793    3.0507    0.2359 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.5664   -1.9849    0.7631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1416   -0.5498    1.7829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2914   -1.5934    0.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2348    0.2646   -0.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2296   -0.9362   -1.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4388    1.4545   -2.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8693   -0.5094    0.6449 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7659   -1.8284    0.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2319   -0.5733    1.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  2  0
  3  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  4 16  1  0
  6 17  1  0
  6 18  1  0
  6 19  1  0
M  CHG  1  10  -1
M  END
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3D SDF for HMDB0304056 (2-aceto-2-hydroxy-butanoate)


  Mrv1533005141512322D          

 10  9  0  0  0  0            999 V2000
    0.5230   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.1270    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
    1.6500   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.7145    0.0000 O   0  5  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 C   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  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
M  CHG  1   7  -1
M  END
> <DATABASE_ID>
HMDB0304056

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(O)(C(C)=O)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O4/c1-3-6(10,4(2)7)5(8)9/h10H,3H2,1-2H3,(H,8,9)/p-1

> <INCHI_KEY>
VUQLHQFKACOHNZ-UHFFFAOYSA-M

> <FORMULA>
C6H9O4

> <MOLECULAR_WEIGHT>
145.135

> <EXACT_MASS>
145.05063235

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
13.287244233245342

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-ethyl-2-hydroxy-3-oxobutanoate

> <ALOGPS_LOGP>
-0.46

> <JCHEM_LOGP>
0.23863807466666656

> <ALOGPS_LOGS>
-0.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.22864662869457

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.602709116384785

> <JCHEM_PKA_STRONGEST_BASIC>
-4.6693092913361545

> <JCHEM_POLAR_SURFACE_AREA>
77.43

> <JCHEM_REFRACTIVITY>
43.95150000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-aceto-2-hydroxybutanoate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0304056 (2-aceto-2-hydroxy-butanoate)

HMDB0304056
     RDKit          3D
2-aceto-2-hydroxy-butanoate
 19 18  0  0  0  0  0  0  0  0999 V2000
   -1.2669   -1.1133    0.8650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2904   -0.2797   -0.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1488    0.7042   -0.4975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3893    1.3648   -1.7311 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1734    0.0169   -0.5847 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7671   -0.7511    0.5429 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7823    0.0973   -1.6310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1493    1.7354    0.5489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0591    1.4310    1.7367 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3793    3.0507    0.2359 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.5664   -1.9849    0.7631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1416   -0.5498    1.7829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2914   -1.5934    0.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2348    0.2646   -0.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2296   -0.9362   -1.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4388    1.4545   -2.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8693   -0.5094    0.6449 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7659   -1.8284    0.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2319   -0.5733    1.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  2  0
  3  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  4 16  1  0
  6 17  1  0
  6 18  1  0
  6 19  1  0
M  CHG  1  10  -1
M  END
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PDB for HMDB0304056 (2-aceto-2-hydroxy-butanoate)

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       0.976  -3.644   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.976  -2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.080  -2.667   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.644   0.976   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       4.977  -1.334   0.000  0.00  0.00           O-1
HETATM    8  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    8                                             
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    3    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for HMDB0304056 (2-aceto-2-hydroxy-butanoate)

COMPND    HMDB0304056
HETATM    1  C1  UNL     1      -1.267  -1.113   0.865  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.290  -0.280  -0.372  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.149   0.704  -0.497  1.00  0.00           C  
HETATM    4  O1  UNL     1      -0.389   1.365  -1.731  1.00  0.00           O  
HETATM    5  C4  UNL     1       1.173   0.017  -0.585  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.767  -0.751   0.543  1.00  0.00           C  
HETATM    7  O2  UNL     1       1.782   0.097  -1.631  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.149   1.735   0.549  1.00  0.00           C  
HETATM    9  O3  UNL     1       0.059   1.431   1.737  1.00  0.00           O  
HETATM   10  O4  UNL     1      -0.379   3.051   0.236  1.00  0.00           O1-
HETATM   11  H1  UNL     1      -0.566  -1.985   0.763  1.00  0.00           H  
HETATM   12  H2  UNL     1      -1.142  -0.550   1.783  1.00  0.00           H  
HETATM   13  H3  UNL     1      -2.291  -1.593   0.939  1.00  0.00           H  
HETATM   14  H4  UNL     1      -2.235   0.265  -0.449  1.00  0.00           H  
HETATM   15  H5  UNL     1      -1.230  -0.936  -1.276  1.00  0.00           H  
HETATM   16  H6  UNL     1       0.439   1.455  -2.245  1.00  0.00           H  
HETATM   17  H7  UNL     1       2.869  -0.509   0.645  1.00  0.00           H  
HETATM   18  H8  UNL     1       1.766  -1.828   0.261  1.00  0.00           H  
HETATM   19  H9  UNL     1       1.232  -0.573   1.474  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3   14   15
CONECT    3    4    5    8
CONECT    4   16
CONECT    5    6    7    7
CONECT    6   17   18   19
CONECT    8    9    9   10
END
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SMILES for HMDB0304056 (2-aceto-2-hydroxy-butanoate)

CCC(O)(C(C)=O)C([O-])=O
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INCHI for HMDB0304056 (2-aceto-2-hydroxy-butanoate)

InChI=1S/C6H10O4/c1-3-6(10,4(2)7)5(8)9/h10H,3H2,1-2H3,(H,8,9)/p-1
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2-Ethyl-2-hydroxy-3-oxobutanoic acidGenerator
2-Aceto-2-hydroxy-butanoic acidGenerator
Chemical FormulaC6H9O4
Average Molecular Weight145.135
Monoisotopic Molecular Weight145.05063235
IUPAC Name2-ethyl-2-hydroxy-3-oxobutanoate
Traditional Name2-aceto-2-hydroxybutanoate
CAS Registry NumberNot Available
SMILES
CCC(O)(C(C)=O)C([O-])=O
InChI Identifier
InChI=1S/C6H10O4/c1-3-6(10,4(2)7)5(8)9/h10H,3H2,1-2H3,(H,8,9)/p-1
InChI KeyVUQLHQFKACOHNZ-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
  • Beta-keto acid
  • Branched fatty acid
  • Short-chain keto acid
  • Hydroxy fatty acid
  • Acyloin
  • Fatty acyl
  • Alpha-hydroxy ketone
  • Tertiary alcohol
  • Ketone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • 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-0.46ALOGPS
logP0.24ChemAxon
logS-0.08ALOGPS
pKa (Strongest Acidic)3.6ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area77.43 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity43.95 m³·mol⁻¹ChemAxon
Polarizability13.29 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]+132.7532859911
AllCCS[M+H-H2O]+128.61932859911
AllCCS[M+Na]+137.7132859911
AllCCS[M+NH4]+136.632859911
AllCCS[M-H]-122.7132859911
AllCCS[M+Na-2H]-124.87432859911
AllCCS[M+HCOO]-127.29632859911
DeepCCS[M+H]+134.74930932474
DeepCCS[M-H]-131.42630932474
DeepCCS[M-2H]-168.13130932474
DeepCCS[M+Na]+143.48930932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-aceto-2-hydroxy-butanoate,2TMS,isomer #1C=C(O[Si](C)(C)C)C(CC)(O[Si](C)(C)C)C(=O)[O-]1297.0Semi standard non polar33892256
2-aceto-2-hydroxy-butanoate,2TMS,isomer #1C=C(O[Si](C)(C)C)C(CC)(O[Si](C)(C)C)C(=O)[O-]1299.4Standard non polar33892256
2-aceto-2-hydroxy-butanoate,2TMS,isomer #1C=C(O[Si](C)(C)C)C(CC)(O[Si](C)(C)C)C(=O)[O-]1395.4Standard polar33892256
2-aceto-2-hydroxy-butanoate,2TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)C(CC)(O[Si](C)(C)C(C)(C)C)C(=O)[O-]1740.3Semi standard non polar33892256
2-aceto-2-hydroxy-butanoate,2TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)C(CC)(O[Si](C)(C)C(C)(C)C)C(=O)[O-]1757.0Standard non polar33892256
2-aceto-2-hydroxy-butanoate,2TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)C(CC)(O[Si](C)(C)C(C)(C)C)C(=O)[O-]1674.3Standard polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-aceto-2-hydroxy-butanoate 10V, Negative-QTOFsplash10-0udi-1900000000-bd8bf159dfce474821d22019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-aceto-2-hydroxy-butanoate 20V, Negative-QTOFsplash10-0zfr-9600000000-e5eeeeed483bd54b61712019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-aceto-2-hydroxy-butanoate 40V, Negative-QTOFsplash10-0abi-9000000000-b08edd56acc52b3284512019-02-23Wishart 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 IDFDB030318
KNApSAcK IDNot Available
Chemspider ID10607847
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13999771
PDB IDNot Available
ChEBI IDNot Available
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