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Showing metabocard for A,b-Dihydroxyisobutyric acid (HMDB0002601)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:58 UTC
Update Date2023-02-21 17:16:26 UTC
HMDB IDHMDB0002601
Secondary Accession Numbers
  • HMDB02601
Metabolite Identification
Common NameA,b-Dihydroxyisobutyric acid
DescriptionA,b-Dihydroxyisobutyric acid, also known as 2,3-dihydroxy-2-methylpropionate or alpha,beta-dihydroxyisobutyrate, belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. A,b-Dihydroxyisobutyric acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make a,b-dihydroxyisobutyric acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on A,b-Dihydroxyisobutyric acid.
Structure
Data?1676999786
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0002601 (A,b-Dihydroxyisobutyric acid)

  Mrv0541 02231219332D          

  8  7  0  0  0  0            999 V2000
   14.2781  -11.8306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9926  -11.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7071  -11.8306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4216  -11.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7071  -12.6556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7071  -11.0056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4216  -10.5931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1360  -11.8306    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
  3  6  1  0  0  0  0
  4  7  2  0  0  0  0
  4  8  1  0  0  0  0
M  END
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3D MOL for HMDB0002601 (A,b-Dihydroxyisobutyric acid)

HMDB0002601
     RDKit          3D
A,b-Dihydroxyisobutyric acid
 16 15  0  0  0  0  0  0  0  0999 V2000
   -0.4877    1.0464   -0.9351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0363    0.2921    0.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3069    1.0355    1.4148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7289   -1.0374    0.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0948   -0.8955    0.5863 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4359    0.0102    0.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2279    0.4387    1.0599 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9349   -0.7077   -0.8814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1964    1.8730   -0.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3485    1.5447   -1.4743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0223    0.4219   -1.6879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4871    1.5244    1.7474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3335   -1.4751    1.3943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4691   -1.7645   -0.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6106   -1.6224    0.1590 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8522   -0.6842   -1.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  2  6  1  0
  6  7  2  0
  6  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
  8 16  1  0
M  END
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3D SDF for HMDB0002601 (A,b-Dihydroxyisobutyric acid)

  Mrv0541 02231219332D          

  8  7  0  0  0  0            999 V2000
   14.2781  -11.8306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9926  -11.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7071  -11.8306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4216  -11.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7071  -12.6556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7071  -11.0056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4216  -10.5931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1360  -11.8306    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
  3  6  1  0  0  0  0
  4  7  2  0  0  0  0
  4  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002601

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C4H8O4/c1-4(8,2-5)3(6)7/h5,8H,2H2,1H3,(H,6,7)

> <INCHI_KEY>
DGADNPLBVRLJGD-UHFFFAOYSA-N

> <FORMULA>
C4H8O4

> <MOLECULAR_WEIGHT>
120.1039

> <EXACT_MASS>
120.042258744

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
10.653759540169283

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,3-dihydroxy-2-methylpropanoic acid

> <ALOGPS_LOGP>
-1.25

> <JCHEM_LOGP>
-1.0859735986666668

> <ALOGPS_LOGS>
0.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.345095100532951

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5921284647538427

> <JCHEM_PKA_STRONGEST_BASIC>
-3.172691351130413

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
25.096799999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.40e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methylglyceric acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0002601 (A,b-Dihydroxyisobutyric acid)

HMDB0002601
     RDKit          3D
A,b-Dihydroxyisobutyric acid
 16 15  0  0  0  0  0  0  0  0999 V2000
   -0.4877    1.0464   -0.9351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0363    0.2921    0.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3069    1.0355    1.4148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7289   -1.0374    0.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0948   -0.8955    0.5863 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4359    0.0102    0.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2279    0.4387    1.0599 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9349   -0.7077   -0.8814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1964    1.8730   -0.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3485    1.5447   -1.4743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0223    0.4219   -1.6879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4871    1.5244    1.7474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3335   -1.4751    1.3943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4691   -1.7645   -0.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6106   -1.6224    0.1590 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8522   -0.6842   -1.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  2  6  1  0
  6  7  2  0
  6  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
  8 16  1  0
M  END
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PDB for HMDB0002601 (A,b-Dihydroxyisobutyric acid)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      26.652 -22.084   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      27.986 -21.314   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      29.320 -22.084   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      30.654 -21.314   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      29.320 -23.624   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      29.320 -20.544   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      30.654 -19.774   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      31.987 -22.084   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3    7    8                                                  
CONECT    5    3                                                            
CONECT    6    3                                                            
CONECT    7    4                                                            
CONECT    8    4                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
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3D PDB for HMDB0002601 (A,b-Dihydroxyisobutyric acid)

COMPND    HMDB0002601
HETATM    1  C1  UNL     1      -0.488   1.046  -0.935  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.036   0.292   0.269  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.307   1.035   1.415  1.00  0.00           O  
HETATM    4  C3  UNL     1      -0.729  -1.037   0.438  1.00  0.00           C  
HETATM    5  O2  UNL     1      -2.095  -0.895   0.586  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.436   0.010   0.168  1.00  0.00           C  
HETATM    7  O3  UNL     1       2.228   0.439   1.060  1.00  0.00           O  
HETATM    8  O4  UNL     1       1.935  -0.708  -0.881  1.00  0.00           O  
HETATM    9  H1  UNL     1      -1.196   1.873  -0.640  1.00  0.00           H  
HETATM   10  H2  UNL     1       0.349   1.545  -1.474  1.00  0.00           H  
HETATM   11  H3  UNL     1      -1.022   0.422  -1.688  1.00  0.00           H  
HETATM   12  H4  UNL     1       0.487   1.524   1.747  1.00  0.00           H  
HETATM   13  H5  UNL     1      -0.334  -1.475   1.394  1.00  0.00           H  
HETATM   14  H6  UNL     1      -0.469  -1.764  -0.367  1.00  0.00           H  
HETATM   15  H7  UNL     1      -2.611  -1.622   0.159  1.00  0.00           H  
HETATM   16  H8  UNL     1       2.852  -0.684  -1.251  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3    4    6
CONECT    3   12
CONECT    4    5   13   14
CONECT    5   15
CONECT    6    7    7    8
CONECT    8   16
END
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SMILES for HMDB0002601 (A,b-Dihydroxyisobutyric acid)

CC(O)(CO)C(O)=O
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INCHI for HMDB0002601 (A,b-Dihydroxyisobutyric acid)

InChI=1S/C4H8O4/c1-4(8,2-5)3(6)7/h5,8H,2H2,1H3,(H,6,7)
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Synonyms
Chemical FormulaC4H8O4
Average Molecular Weight120.1039
Monoisotopic Molecular Weight120.042258744
IUPAC Name2,3-dihydroxy-2-methylpropanoic acid
Traditional Name2-methylglyceric acid
CAS Registry Number21620-60-0
SMILES
CC(O)(CO)C(O)=O
InChI Identifier
InChI=1S/C4H8O4/c1-4(8,2-5)3(6)7/h5,8H,2H2,1H3,(H,6,7)
InChI KeyDGADNPLBVRLJGD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassBeta hydroxy acids and derivatives
Direct ParentBeta hydroxy acids and derivatives
Alternative Parents
Substituents
  • Beta-hydroxy acid
  • Alpha-hydroxy acid
  • Tertiary alcohol
  • 1,2-diol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
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
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
 details
UrineDetected and Quantified1.0 (0.0-2.0) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023033
KNApSAcK IDNot Available
Chemspider ID487503
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6723
PubChem Compound560781
PDB IDNot Available
ChEBI ID36532
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 References
  1. Niwa T, Maeda K, Asada H, Shibata M, Ohki T, Saito A, Furukawa H: Gas chromatographic-mass spectrometric analysis of organic acids in renal tissue biopsy: identification of 4-hydroxybutyric acid and 4-hydroxy-2-butenoic acid. J Chromatogr. 1982 Jun 11;230(1):1-6. [PubMed:7107749 ]
  2. Schellenberg KA, Shaeffer J: Formation of methyl ester of 2-methylglyceric acid from thymine glycol residues: a convenient new method for determining radiation damage to DNA. Biochemistry. 1986 Apr 8;25(7):1479-82. [PubMed:3707888 ]