Np mrd loader

Showing NP-Card for alpha,beta-Dihydroxyisobutyric acid (NP0086995)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-05-11 16:36:49 UTC
Updated at2022-05-11 16:36:49 UTC
NP-MRD IDNP0086995
Secondary Accession NumbersNone
Natural Product Identification
Common Namealpha,beta-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. alpha,beta-Dihydroxyisobutyric acid was first documented in 1986 (PMID: 3707888). A,b-Dihydroxyisobutyric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0086995 (alpha,beta-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
Download

3D MOL for NP0086995 (alpha,beta-Dihydroxyisobutyric acid)

     RDKit          3D

 16 15  0  0  0  0  0  0  0  0999 V2000
   -0.0189   -1.4265    0.6317 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1974    0.0420    0.2739 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7256    0.7019    1.3810 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1844    0.6406    0.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7043   -0.0375   -1.0821 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0613    0.1797   -0.9129 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7238   -0.3577   -1.9877 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2430    0.8907   -0.8739 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4515   -1.6444    1.6107 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3989   -2.0957   -0.1527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0924   -1.6779    0.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7036    1.6753    1.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8100    0.3356    0.9042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1506    1.7296   -0.1166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5017    0.5147   -1.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9572    0.5297   -0.2217 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  1
  2  4  1  0
  4  5  1  0
  2  6  1  0
  6  8  1  0
  6  7  2  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
Download

3D SDF for NP0086995 (alpha,beta-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>
NP0086995

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
Download

3D-SDF for NP0086995 (alpha,beta-Dihydroxyisobutyric acid)

Download
PDB for NP0086995 (alpha,beta-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

Download
3D PDB for NP0086995 (alpha,beta-Dihydroxyisobutyric acid)
Download
SMILES for NP0086995 (alpha,beta-Dihydroxyisobutyric acid)
CC(O)(CO)C(O)=O
Download
INCHI for NP0086995 (alpha,beta-Dihydroxyisobutyric acid)
InChI=1S/C4H8O4/c1-4(8,2-5)3(6)7/h5,8H,2H2,1H3,(H,6,7)
Download
View in JSmol
Synonyms
ValueSource
2,3-Dihydroxy-2-methylpropionic acidChEBI
alpha,beta-Dihydroxyisobutyric acidChEBI
2,3-Dihydroxy-2-methylpropionateGenerator
a,b-DihydroxyisobutyrateGenerator
alpha,beta-DihydroxyisobutyrateGenerator
Α,β-dihydroxyisobutyrateGenerator
Α,β-dihydroxyisobutyric acidGenerator
2,3-Dihydroxy-2-methyl-propanoateHMDB
2,3-Dihydroxy-2-methyl-propanoic acidHMDB
2,3-Dihydroxy-2-methylpropanoateHMDB
2,3-Dihydroxy-2-methylpropanoic acidHMDB
2-C-MethylglycerateHMDB
2-C-Methylglyceric acidHMDB
2-Methyl-2,3-dihydroxypropionateHMDB
2-Methyl-2,3-dihydroxypropionic acidHMDB
2-MethylglycerateHMDB
2-Methylglyceric acidHMDB
2-MethylglyceronateHMDB
2-Methylglyceronic acidHMDB
a-MethylglycerateHMDB
a-Methylglyceric acidHMDB
alpha-MethylglycerateHMDB
alpha-Methylglyceric acidHMDB
a,b-Dihydroxy-isobutyrateHMDB
a,b-Dihydroxyisobutyric acidGenerator
Chemical FormulaC4H8O4
Average Mass120.1039 Da
Monoisotopic Mass120.04226 Da
IUPAC Name2,3-dihydroxy-2-methylpropanoic acid
Traditional Name2-methylglyceric acid
CAS Registry NumberNot Available
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
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 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
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-1.2ALOGPS
logP-1.1ChemAxon
logS0.65ALOGPS
pKa (Strongest Acidic)3.59ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity25.1 m³·mol⁻¹ChemAxon
Polarizability10.65 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002601  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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  
Good Scents IDNot Available
References
General References
  1. 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. doi: 10.1021/bi00355a002. [PubMed:3707888  ]