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Showing NP-Card for 2-hydroxy-2-(2-methylpropyl)butanedioic acid (NP0159416)

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Record Information
Version2.0
Created at2022-09-02 17:10:03 UTC
Updated at2022-09-02 17:10:03 UTC
NP-MRD IDNP0159416
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-hydroxy-2-(2-methylpropyl)butanedioic acid
Description2-Hydroxy-2-(2-methylpropyl)butanedioic acid belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain. 2-hydroxy-2-(2-methylpropyl)butanedioic acid is found in Dactylorhiza hatagirea. 2-Hydroxy-2-(2-methylpropyl)butanedioic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0159416 (2-hydroxy-2-(2-methylpropyl)butanedioic acid)


  Mrv1533004231519552D          

 13 12  0  0  0  0            999 V2000
    1.2375   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914   -2.3645    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
    2.6664   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -1.5395    0.0000 O   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
    1.2375    0.7145    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  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
M  END
Download

3D MOL for NP0159416 (2-hydroxy-2-(2-methylpropyl)butanedioic acid)

     RDKit          3D

 27 26  0  0  0  0  0  0  0  0999 V2000
   -2.2417   -0.4904   -0.2027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2596    0.6296   -0.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0316    1.9286   -0.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1211    0.6136    0.5798 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6874   -0.6561    0.5046 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2412   -1.6881    0.7987 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2043   -0.9553   -0.8570 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0841    0.0476   -1.4500 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5746   -0.1892   -2.6061 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4203    1.2271   -0.8517 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7344   -0.6350    1.5480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6786    0.1834    1.5360 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6889   -1.5468    2.5883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3862   -0.7667    0.8602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2636   -0.1855   -0.5727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9267   -1.3446   -0.8344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8333    0.5728   -1.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1631    2.2176    0.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4981    2.7168   -0.8768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0642    1.7699   -0.6914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5711    0.6463    1.6014 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4606    1.5263    0.4484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1019   -2.4749    0.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3621   -1.1905   -1.5312 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7929   -1.9115   -0.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2654    1.7533   -1.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7498   -1.7982    2.9236 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
  5  6  1  1
  5  7  1  0
  7  8  1  0
  8 10  1  0
  8  9  2  0
  5 11  1  0
 11 13  1  0
 11 12  2  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  3 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
 10 26  1  0
 13 27  1  0
M  END
Download

3D SDF for NP0159416 (2-hydroxy-2-(2-methylpropyl)butanedioic acid)


  Mrv1533004231519552D          

 13 12  0  0  0  0            999 V2000
    1.2375   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914   -2.3645    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
    2.6664   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -1.5395    0.0000 O   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
    1.2375    0.7145    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  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0159416

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H14O5/c1-5(2)3-8(13,7(11)12)4-6(9)10/h5,13H,3-4H2,1-2H3,(H,9,10)(H,11,12)

> <INCHI_KEY>
AOJRRQNPQBDATA-UHFFFAOYSA-N

> <FORMULA>
C8H14O5

> <MOLECULAR_WEIGHT>
190.195

> <EXACT_MASS>
190.084123551

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
18.340230634291892

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-2-(2-methylpropyl)butanedioic acid

> <ALOGPS_LOGP>
-0.10

> <JCHEM_LOGP>
0.573234614333333

> <ALOGPS_LOGS>
-0.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.667144479671144

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.744331655106462

> <JCHEM_PKA_STRONGEST_BASIC>
-4.069351560961864

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
43.262100000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.07e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-2-(2-methylpropyl)butanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0159416 (2-hydroxy-2-(2-methylpropyl)butanedioic acid)

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PDB for NP0159416 (2-hydroxy-2-(2-methylpropyl)butanedioic acid)
HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       2.310  -4.414   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.976  -3.644   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.357  -4.414   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.976  -2.104   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.080  -2.667   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.977  -1.334   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.311  -0.564   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       4.977  -2.874   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.310   1.334   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7   11                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    5   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

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3D PDB for NP0159416 (2-hydroxy-2-(2-methylpropyl)butanedioic acid)
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SMILES for NP0159416 (2-hydroxy-2-(2-methylpropyl)butanedioic acid)
CC(C)CC(O)(CC(O)=O)C(O)=O
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INCHI for NP0159416 (2-hydroxy-2-(2-methylpropyl)butanedioic acid)
InChI=1S/C8H14O5/c1-5(2)3-8(13,7(11)12)4-6(9)10/h5,13H,3-4H2,1-2H3,(H,9,10)(H,11,12)
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View in JSmol
Synonyms
ValueSource
2-Hydroxy-2-(2-methylpropyl)butanedioateGenerator
IsobutylmalateGenerator
Chemical FormulaC8H14O5
Average Mass190.1950 Da
Monoisotopic Mass190.08412 Da
IUPAC Name2-hydroxy-2-(2-methylpropyl)butanedioic acid
Traditional Name2-hydroxy-2-(2-methylpropyl)butanedioic acid
CAS Registry NumberNot Available
SMILES
CC(C)CC(O)(CC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C8H14O5/c1-5(2)3-8(13,7(11)12)4-6(9)10/h5,13H,3-4H2,1-2H3,(H,9,10)(H,11,12)
InChI KeyAOJRRQNPQBDATA-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
Orchis hatagireaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassHydroxy acids and derivatives  
Sub ClassMedium-chain hydroxy acids and derivatives  
Direct ParentMedium-chain hydroxy acids and derivatives  
Alternative Parents
Substituents
  • Medium-chain hydroxy acid
    • 

  • Medium-chain fatty acid
    • 

  • Branched fatty acid
    • 

  • Hydroxy fatty acid
    • 

  • Methyl-branched fatty acid
    • 

  • Alpha-hydroxy acid
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Fatty acid
    • 

  • Fatty acyl
    • 

  • Tertiary alcohol
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Alcohol
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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-0.1ALOGPS
logP0.57ChemAxon
logS-0.25ALOGPS
pKa (Strongest Acidic)3.74ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity43.26 m³·mol⁻¹ChemAxon
Polarizability18.34 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound20563475  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]