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Showing NP-Card for 2-(benzoyloxy)-3-hydroxybutanedioic acid (NP0271967)

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Record Information
Version2.0
Created at2022-09-08 18:25:57 UTC
Updated at2022-09-08 18:25:57 UTC
NP-MRD IDNP0271967
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-(benzoyloxy)-3-hydroxybutanedioic acid
DescriptionBenzoyl meso-tartaric acid belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Benzoyl meso-tartaric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Benzoyl meso-tartaric acid has been detected, but not quantified in, pulses. 2-(benzoyloxy)-3-hydroxybutanedioic acid is found in Medicago sativa. This could make benzoyl meso-tartaric acid a potential biomarker for the consumption of these foods.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0271967 (2-(benzoyloxy)-3-hydroxybutanedioic acid)


  Mrv0541 05061311112D          

 18 18  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
  6  5  1  0  0  0  0
  8  7  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 13  9  2  0  0  0  0
 14  9  1  0  0  0  0
 15 10  2  0  0  0  0
 16 10  1  0  0  0  0
 17 11  2  0  0  0  0
 18  8  1  0  0  0  0
 18 11  1  0  0  0  0
M  END
Download

3D MOL for NP0271967 (2-(benzoyloxy)-3-hydroxybutanedioic acid)

     RDKit          3D

 28 28  0  0  0  0  0  0  0  0999 V2000
   -0.1557    0.3747    1.8260 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5420    0.2315    0.6386 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4386    0.1516   -0.3378 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8246    0.2316    0.0197 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4286    1.4096   -0.6135 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5974    1.8224   -0.4723 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6018    2.1667   -1.4816 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5001   -1.0873   -0.3015 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7589   -2.0277    0.4781 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8949   -1.0503    0.1760 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2137   -1.6720    1.2206 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8741   -0.3533   -0.4915 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9533    0.1600    0.3644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4425    0.0014   -0.9361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7927   -0.0681   -1.2079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7091    0.0202   -0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2160    0.1758    1.1001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8829    0.2449    1.3728 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8752    0.3550    1.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9410    2.8239   -1.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3818   -1.3595   -1.3536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7239   -2.8990    0.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    0.0279    0.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7121   -0.0655   -1.7310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1546   -0.1917   -2.2268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7575   -0.0380   -0.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9228    0.2466    1.9231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4789    0.3685    2.3804 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  4  5  1  0
  5  7  1  0
  5  6  2  0
  8 10  1  0
 10 12  1  0
 10 11  2  0
 18 13  1  0
  9 22  1  0
  8 21  1  6
  4 19  1  1
 14 24  1  0
 15 25  1  0
 16 26  1  0
 17 27  1  0
 18 28  1  0
  7 20  1  0
 12 23  1  0
M  END
Download

3D SDF for NP0271967 (2-(benzoyloxy)-3-hydroxybutanedioic acid)


  Mrv0541 05061311112D          

 18 18  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
  6  5  1  0  0  0  0
  8  7  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 13  9  2  0  0  0  0
 14  9  1  0  0  0  0
 15 10  2  0  0  0  0
 16 10  1  0  0  0  0
 17 11  2  0  0  0  0
 18  8  1  0  0  0  0
 18 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0271967

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(C(OC(=O)C1=CC=CC=C1)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H10O7/c12-7(9(13)14)8(10(15)16)18-11(17)6-4-2-1-3-5-6/h1-5,7-8,12H,(H,13,14)(H,15,16)

> <INCHI_KEY>
JXXURQWKKCNUBH-UHFFFAOYSA-N

> <FORMULA>
C11H10O7

> <MOLECULAR_WEIGHT>
254.1929

> <EXACT_MASS>
254.042652674

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
22.731903634211413

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(benzoyloxy)-3-hydroxybutanedioic acid

> <ALOGPS_LOGP>
0.86

> <JCHEM_LOGP>
0.66649996

> <ALOGPS_LOGS>
-1.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.4850144453094165

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.028609064248597

> <JCHEM_PKA_STRONGEST_BASIC>
-4.345626274564384

> <JCHEM_POLAR_SURFACE_AREA>
121.13000000000001

> <JCHEM_REFRACTIVITY>
56.03540000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.67e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(benzoyloxy)-3-hydroxybutanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0271967 (2-(benzoyloxy)-3-hydroxybutanedioic acid)

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PDB for NP0271967 (2-(benzoyloxy)-3-hydroxybutanedioic acid)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      10.669   3.080   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       9.336   0.770   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.001   0.770   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.335   3.080   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    6                                                       
CONECT    6    4    5   11                                                  
CONECT    7    8    9   12                                                  
CONECT    8    7   10   18                                                  
CONECT    9    7   13   14                                                  
CONECT   10    8   15   16                                                  
CONECT   11    6   17   18                                                  
CONECT   12    7                                                            
CONECT   13    9                                                            
CONECT   14    9                                                            
CONECT   15   10                                                            
CONECT   16   10                                                            
CONECT   17   11                                                            
CONECT   18    8   11                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

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3D PDB for NP0271967 (2-(benzoyloxy)-3-hydroxybutanedioic acid)
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SMILES for NP0271967 (2-(benzoyloxy)-3-hydroxybutanedioic acid)
OC(C(OC(=O)C1=CC=CC=C1)C(O)=O)C(O)=O
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INCHI for NP0271967 (2-(benzoyloxy)-3-hydroxybutanedioic acid)
InChI=1S/C11H10O7/c12-7(9(13)14)8(10(15)16)18-11(17)6-4-2-1-3-5-6/h1-5,7-8,12H,(H,13,14)(H,15,16)
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View in JSmol
Synonyms
ValueSource
Benzoyl meso-tartarateGenerator
2-(Benzoyloxy)-3-hydroxybutanedioateGenerator
Chemical FormulaC11H10O7
Average Mass254.1929 Da
Monoisotopic Mass254.04265 Da
IUPAC Name2-(benzoyloxy)-3-hydroxybutanedioic acid
Traditional Name2-(benzoyloxy)-3-hydroxybutanedioic acid
CAS Registry NumberNot Available
SMILES
OC(C(OC(=O)C1=CC=CC=C1)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C11H10O7/c12-7(9(13)14)8(10(15)16)18-11(17)6-4-2-1-3-5-6/h1-5,7-8,12H,(H,13,14)(H,15,16)
InChI KeyJXXURQWKKCNUBH-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
Medicago sativaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassBenzoic acids and derivatives  
Direct ParentBenzoic acid esters  
Alternative Parents
Substituents
  • Benzoate ester
    • 

  • Tricarboxylic acid or derivatives
    • 

  • Benzoyl
    • 

  • Sugar acid
    • 

  • Beta-hydroxy acid
    • 

  • Alpha-hydroxy acid
    • 

  • Hydroxy acid
    • 

  • Monosaccharide
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid ester
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Alcohol
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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
logP0.86ALOGPS
logP0.67ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)3.03ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area121.13 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity56.04 m³·mol⁻¹ChemAxon
Polarizability22.73 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0039511  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB019121  
KNApSAcK IDNot Available
Chemspider ID15302874  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13708642  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]