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Showing NP-Card for 2-keto-d-gluconic acid (NP0291222)

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Record Information
Version1.0
Created at2022-09-09 22:13:57 UTC
Updated at2022-09-09 22:13:57 UTC
NP-MRD IDNP0291222
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-keto-d-gluconic acid
Description2-Keto-L-gluconate, also known as 2-dehydro-L-idonate or 2-ketoidonate, belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. 2-keto-d-gluconic acid is found in Burkholderia cepacia. 2-Keto-L-gluconate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0291222 (2-keto-d-gluconic acid)


  Mrv0541 02241201522D          

 13 12  0  0  0  0            999 V2000
   16.2552  -13.5918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2552  -14.4168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5407  -14.8293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8262  -14.4168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1117  -14.8293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1117  -15.6543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5407  -13.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9696  -14.8293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5407  -15.6543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8262  -13.5918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3972  -14.4168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3972  -16.0668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8262  -16.0668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  1  2  1  0  0  0  0
  2  8  1  0  0  0  0
  2  3  1  0  0  0  0
  3  9  1  0  0  0  0
  3  4  1  0  0  0  0
  4 10  1  0  0  0  0
  4  5  1  0  0  0  0
  5 11  2  0  0  0  0
  5  6  1  0  0  0  0
  6 12  1  0  0  0  0
  6 13  2  0  0  0  0
M  END
Download

3D MOL for NP0291222 (2-keto-d-gluconic acid)

     RDKit          3D

 23 22  0  0  0  0  0  0  0  0999 V2000
    2.2819    1.8851   -0.2795 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6475    1.0710    0.5914 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5826    1.4409    1.5259 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0790   -0.2534    0.6031 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4840   -1.0560    1.5104 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0567   -0.6943   -0.3939 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7260   -2.0277   -0.1229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1738    0.1621   -0.1865 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5589    0.0017    1.1422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2879   -0.2529   -1.1387 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5585   -1.5955   -0.8808 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5354    0.5345   -0.7421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7158    0.2678    0.6343 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4539    2.1841    2.2086 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4618   -0.5344   -1.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0077   -2.5681   -0.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0463    1.2336   -0.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4280   -0.9600    1.3660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9967   -0.0648   -2.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8595   -1.6408    0.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4176    0.1628   -1.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3916    1.6236   -0.9038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9038    1.0806    1.1463 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 10  1  0
 10 11  1  0
 10  8  1  0
  8  9  1  0
  8  6  1  0
  6  7  1  0
  6  4  1  0
  4  5  2  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
 13 23  1  0
 12 21  1  0
 12 22  1  0
 10 19  1  6
 11 20  1  0
  8 17  1  1
  9 18  1  0
  6 15  1  6
  7 16  1  0
  3 14  1  0
M  END
Download

3D SDF for NP0291222 (2-keto-d-gluconic acid)


  Mrv0541 02241201522D          

 13 12  0  0  0  0            999 V2000
   16.2552  -13.5918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2552  -14.4168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5407  -14.8293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8262  -14.4168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1117  -14.8293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1117  -15.6543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5407  -13.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9696  -14.8293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5407  -15.6543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8262  -13.5918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3972  -14.4168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3972  -16.0668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8262  -16.0668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  1  2  1  0  0  0  0
  2  8  1  0  0  0  0
  2  3  1  0  0  0  0
  3  9  1  0  0  0  0
  3  4  1  0  0  0  0
  4 10  1  0  0  0  0
  4  5  1  0  0  0  0
  5 11  2  0  0  0  0
  5  6  1  0  0  0  0
  6 12  1  0  0  0  0
  6 13  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0291222

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-4,7-10H,1H2,(H,12,13)

> <INCHI_KEY>
VBUYCZFBVCCYFD-UHFFFAOYSA-N

> <FORMULA>
C6H10O7

> <MOLECULAR_WEIGHT>
194.1394

> <EXACT_MASS>
194.042652674

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
16.301498108280345

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4,5,6-tetrahydroxy-2-oxohexanoic acid

> <ALOGPS_LOGP>
-2.41

> <JCHEM_LOGP>
-2.4901897010000003

> <ALOGPS_LOGS>
-0.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.707347147009507

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.674777431403159

> <JCHEM_PKA_STRONGEST_BASIC>
-2.974510717467533

> <JCHEM_POLAR_SURFACE_AREA>
135.29000000000002

> <JCHEM_REFRACTIVITY>
37.6545

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.01e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-keto-D-gluconic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0291222 (2-keto-d-gluconic acid)

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PDB for NP0291222 (2-keto-d-gluconic acid)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      30.343 -25.371   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      30.343 -26.911   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      29.009 -27.681   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      27.676 -26.911   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      26.342 -27.681   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      26.342 -29.221   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      29.009 -24.601   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      31.677 -27.681   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      29.009 -29.221   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      27.676 -25.371   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      25.008 -26.911   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      25.008 -29.991   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      27.676 -29.991   0.000  0.00  0.00           O+0
CONECT    1    7    2                                                       
CONECT    2    1    8    3                                                  
CONECT    3    2    9    4                                                  
CONECT    4    3   10    5                                                  
CONECT    5    4   11    6                                                  
CONECT    6    5   12   13                                                  
CONECT    7    1                                                            
CONECT    8    2                                                            
CONECT    9    3                                                            
CONECT   10    4                                                            
CONECT   11    5                                                            
CONECT   12    6                                                            
CONECT   13    6                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

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3D PDB for NP0291222 (2-keto-d-gluconic acid)
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SMILES for NP0291222 (2-keto-d-gluconic acid)
OCC(O)C(O)C(O)C(=O)C(O)=O
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INCHI for NP0291222 (2-keto-d-gluconic acid)
InChI=1S/C6H10O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-4,7-10H,1H2,(H,12,13)
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View in JSmol
Synonyms
ValueSource
2-Keto-L-gluconic acidGenerator
2-Dehydro-D-gluconateHMDB
2-Dehydro-L-idonateHMDB
2-Keto-D-gluconateHMDB
2-Keto-L-gulonateHMDB
2-KetoidonateHMDB
2-Oxogluconic acidHMDB
L-KetoidonateHMDB
L-Ketoidonic acidHMDB
L-SorbosonateHMDB
L-Sorbosonic acidHMDB
Provitamin CHMDB
Provitamin C, monosodium saltHMDB
2-Keto-L-gulonic acidHMDB
Provitamin C, (L-xylo)-isomerHMDB
Chemical FormulaC6H10O7
Average Mass194.1394 Da
Monoisotopic Mass194.04265 Da
IUPAC Name3,4,5,6-tetrahydroxy-2-oxohexanoic acid
Traditional Name2-keto-D-gluconic acid
CAS Registry NumberNot Available
SMILES
OCC(O)C(O)C(O)C(=O)C(O)=O
InChI Identifier
InChI=1S/C6H10O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-4,7-10H,1H2,(H,12,13)
InChI KeyVBUYCZFBVCCYFD-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
Burkholderia cepaciaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbohydrates and carbohydrate conjugates  
Direct ParentSugar acids and derivatives  
Alternative Parents
Substituents
  • Hexose monosaccharide
    • 

  • Medium-chain keto acid
    • 

  • Beta-hydroxy acid
    • 

  • Sugar acid
    • 

  • Acyloin
    • 

  • Alpha-keto acid
    • 

  • Beta-hydroxy ketone
    • 

  • Hydroxy acid
    • 

  • Keto acid
    • 

  • Monosaccharide
    • 

  • Alpha-hydroxy ketone
    • 

  • Ketone
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Polyol
    • 

  • Alcohol
    • 

  • Hydrocarbon derivative
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Primary alcohol
    • 

  • 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-2.4ALOGPS
logP-2.5ChemAxon
logS-0.28ALOGPS
pKa (Strongest Acidic)2.67ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area135.29 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity37.65 m³·mol⁻¹ChemAxon
Polarizability16.3 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0011732  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB028412  
KNApSAcK IDNot Available
Chemspider ID49  
KEGG Compound IDC03342  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound50  
PDB IDNot Available
ChEBI ID88378  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]