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Showing NP-Card for 2,3-dihydroxyisovaleric acid (NP0323367)

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Record Information
Version2.0
Created at2022-09-12 02:44:22 UTC
Updated at2022-09-12 02:44:22 UTC
NP-MRD IDNP0323367
Secondary Accession NumbersNone
Natural Product Identification
Common Name2,3-dihydroxyisovaleric acid
Description2,3-Dihydroxyisovaleric acid, also known as 2,3-dihydroxy-3-methylbutyrate or a,b-dihydroxyisovalerate, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. 2,3-Dihydroxyisovaleric acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0323367 (2,3-dihydroxyisovaleric acid)


  Mrv1652309121709242D          

  9  8  0  0  0  0            999 V2000
    0.8250   -0.8250    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
    1.6500   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.2375    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  4  8  1  0  0  0  0
  2  9  1  0  0  0  0
M  END
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3D MOL for NP0323367 (2,3-dihydroxyisovaleric acid)

     RDKit          3D

 19 18  0  0  0  0  0  0  0  0999 V2000
   -1.1976   -1.0767   -0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4488    0.0942    0.4987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3313    1.3241    0.5053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1540   -0.1722    1.8456 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8569    0.3474   -0.2174 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6895    0.6203   -1.5546 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8101   -0.7559   -0.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3186   -1.2798   -1.0740 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1541   -1.2260    1.1664 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0010   -2.0254    0.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0037   -1.1028   -1.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3093   -0.8988    0.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9953    1.9962    1.3366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3519    0.9876    0.8048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3917    1.8315   -0.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0437   -0.1184    2.3177 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2963    1.2895    0.2324 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9991    1.5082   -1.8364 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1038   -1.3429    1.5044 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
  2  5  1  0
  5  6  1  0
  5  7  1  0
  7  9  1  0
  7  8  2  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  3 14  1  0
  3 15  1  0
  4 16  1  0
  5 17  1  1
  6 18  1  0
  9 19  1  0
M  END
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3D SDF for NP0323367 (2,3-dihydroxyisovaleric acid)


  Mrv1652309121709242D          

  9  8  0  0  0  0            999 V2000
    0.8250   -0.8250    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
    1.6500   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.2375    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  4  8  1  0  0  0  0
  2  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0323367

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H10O4/c1-5(2,9)3(6)4(7)8/h3,6,9H,1-2H3,(H,7,8)

> <INCHI_KEY>
JTEYKUFKXGDTEU-UHFFFAOYSA-N

> <FORMULA>
C5H10O4

> <MOLECULAR_WEIGHT>
134.1305

> <EXACT_MASS>
134.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
12.4676669606666

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.83

> <JCHEM_LOGP>
-0.8215877916666663

> <ALOGPS_LOGS>
0.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.137895474801091

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7976532415810835

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2052703412545993

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
29.4405

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.29e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,3-dihydroxyisovaleric acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0323367 (2,3-dihydroxyisovaleric acid)

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PDB for NP0323367 (2,3-dihydroxyisovaleric acid)
HEADER    PROTEIN                                 12-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-17         0                                  
HETATM    1  C   UNK     0       1.540  -1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.080  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.540   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.874   2.310   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.874   3.850   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       4.207   1.540   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.206   2.310   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    9                                             
CONECT    3    2                                                            
CONECT    4    2    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    4                                                            
CONECT    9    2                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END

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3D PDB for NP0323367 (2,3-dihydroxyisovaleric acid)
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SMILES for NP0323367 (2,3-dihydroxyisovaleric acid)
CC(C)(O)C(O)C(O)=O
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INCHI for NP0323367 (2,3-dihydroxyisovaleric acid)
InChI=1S/C5H10O4/c1-5(2,9)3(6)4(7)8/h3,6,9H,1-2H3,(H,7,8)
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Synonyms
ValueSource
2,3-Dihydroxy-3-methylbutyric acidChEBI
2,3-Dihydroxy-isovaleric acidChEBI
alpha,beta-Dihydroxyisovaleric acidChEBI
2,3-Dihydroxy-isovalerateKegg
2,3-Dihydroxy-3-methylbutyrateGenerator
a,b-DihydroxyisovalerateGenerator
a,b-Dihydroxyisovaleric acidGenerator
alpha,beta-DihydroxyisovalerateGenerator
Α,β-dihydroxyisovalerateGenerator
Α,β-dihydroxyisovaleric acidGenerator
2,3-DihydroxyisovalerateGenerator
alpha,beta-Dihydroxyisovaleric acid, (+-)-isomerMeSH
alpha,beta-Dihydroxyisovaleric acid, (R)-isomerMeSH
alpha,beta-Dihydroxyisovaleric acid, monosodium saltMeSH
Chemical FormulaC5H10O4
Average Mass134.1305 Da
Monoisotopic Mass134.05791 Da
IUPAC Name2,3-dihydroxy-3-methylbutanoic acid
Traditional Name2,3-dihydroxyisovaleric acid
CAS Registry NumberNot Available
SMILES
CC(C)(O)C(O)C(O)=O
InChI Identifier
InChI=1S/C5H10O4/c1-5(2,9)3(6)4(7)8/h3,6,9H,1-2H3,(H,7,8)
InChI KeyJTEYKUFKXGDTEU-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 OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty acids and conjugates  
Direct ParentHydroxy fatty acids  
Alternative Parents
Substituents
  • Branched fatty acid
    • 

  • Methyl-branched fatty acid
    • 

  • Short-chain hydroxy acid
    • 

  • Hydroxy fatty acid
    • 

  • Alpha-hydroxy acid
    • 

  • Hydroxy acid
    • 

  • Monosaccharide
    • 

  • Tertiary alcohol
    • 

  • 1,2-diol
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Alcohol
    • 

  • Organooxygen compound
    • 

  • 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-0.83ALOGPS
logP-0.82ChemAxon
logS0.6ALOGPS
pKa (Strongest Acidic)3.8ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity29.44 m³·mol⁻¹ChemAxon
Polarizability12.47 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 IDNot Available
KNApSAcK IDC00019678  
Chemspider IDNot Available
KEGG Compound IDC04039  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound677  
PDB IDNot Available
ChEBI ID15689  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]