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Showing metabocard for Gluconic acid (HMDB0000625)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
enzymes (2) Show 2 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-11-15 21:04:31 UTC
HMDB IDHMDB0000625
Secondary Accession Numbers
  • HMDB0003373
  • HMDB00625
  • HMDB03373
Metabolite Identification
Common NameGluconic acid
DescriptionGluconic acid, also known as D-gluconic acid, D-gluconate or (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid (also named dextronic acid), is the C1-oxidized form of D-glucose where the aldehyde group has become oxidized to the corresponding carboxylic acid. Gluconic acid 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. In aqueous solution, gluconic acid exists in equilibrium with the cyclic ester glucono delta-lactone. Gluconic acid occurs naturally in fruit, honey, kombucha tea and wine. The salts of gluconic acid are known as "gluconates". Gluconic acid, gluconate salts, and gluconate esters occur widely in nature because such species arise from the oxidation of glucose. Gluconic acid exists in all living species, ranging from bacteria to plants to humans. The metabolism of gluconate is well characterized in prokaryotes where it is known to be degraded following phosphorylation by gluconokinase. Glucokinase activity has also been detected in mammals, including humans (PMID: 24896608 ). Gluconic acid is produced in the gluconate shunt pathway. In the gluconate shunt, glucose is oxidized by glucose dehydrogenase (also called glucose oxidase) to furnish gluconate, the form in which D-gluconic acid is present at physiological pH. Subsequently, gluconate is phosphorylated by the action of gluconate kinase to produce 6-phosphogluconate, which is the second intermediate of the pentose phosphate pathway. This gluconate shunt is mainly found in plants, algae, cyanobacteria and some bacteria, which all use the Entner-Doudoroff pathway to degrade glucose or gluconate; this generates 2-keto-3-deoxygluconate-6-phosphate, which is then cleaved to generate pyruvate and glyceraldehyde 3-phosphate. Glucose dehydrogenase and gluconate kinase activities are also present in mammals, fission yeast, and flies. Gluconic acid has many industrial uses. It is used as a drug as part of electrolyte supplementation in total parenteral nutrition. It is also used in cleaning products where it helps cleaning up mineral deposits. Gluconic acid or Gluconic acid is used to maintain the cation-anion balance on electrolyte solutions. In humans, gluconic acid is involved in the metabolic disorder called the transaldolase deficiency. Gluconic acid has been found to be a metabolite in Aspergillus (Hugo Vanden Bossche, D.W.R. Mackenzie and G. Cauwenbergh. Aspergillus and Aspergillosis, 1987).
Structure
Data?1582752144
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000625 (Gluconic acid)


  Mrv1652309042000042D          

 13 12  0  0  1  0            999 V2000
   22.2164  -15.6487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5020  -17.7111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9309  -17.7111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7876  -15.6487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3597  -16.8862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3587  -16.4736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0732  -17.7111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2164  -16.4736    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   21.5020  -16.8862    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.9309  -16.8862    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.7876  -16.4736    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.6452  -16.4736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0732  -16.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  6  0  0  0
  9  2  1  6  0  0  0
 10  3  1  1  0  0  0
 11  4  1  6  0  0  0
  5 12  1  0  0  0  0
  6 13  1  0  0  0  0
  7 13  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
M  END
Download

3D MOL for HMDB0000625 (Gluconic acid)

HMDB0000625
     RDKit          3D
Gluconic acid
 25 24  0  0  0  0  0  0  0  0999 V2000
    3.6956   -0.0617    1.4192 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5956   -0.4739    0.9694 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7514   -1.1292    1.8494 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1738   -0.2922   -0.4342 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2409    0.3674   -1.0906 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9210    0.5609   -0.5741 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7175    0.6694   -1.9739 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2928   -0.1346    0.0078 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4042   -1.4053   -0.5694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5558    0.6361   -0.3337 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4740    1.8921    0.2223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7755   -0.0604    0.1943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7480   -0.2007    1.5752 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5806   -0.7331    2.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0014   -1.2224   -0.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9173    1.1407   -1.6089 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0530    1.5784   -0.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7787   -0.2843   -2.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2472   -0.2529    1.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8161   -1.3337   -1.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5977    0.7092   -1.4268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3097    1.8432    1.1927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8617   -1.0869   -0.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6700    0.5266   -0.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6742   -0.1997    1.9317 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
  3 14  1  0
  4 15  1  6
  5 16  1  0
  6 17  1  1
  7 18  1  0
  8 19  1  1
  9 20  1  0
 10 21  1  6
 11 22  1  0
 12 23  1  0
 12 24  1  0
 13 25  1  0
M  END
Download

3D SDF for HMDB0000625 (Gluconic acid)


  Mrv1652309042000042D          

 13 12  0  0  1  0            999 V2000
   22.2164  -15.6487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5020  -17.7111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9309  -17.7111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7876  -15.6487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3597  -16.8862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3587  -16.4736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0732  -17.7111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2164  -16.4736    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   21.5020  -16.8862    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.9309  -16.8862    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.7876  -16.4736    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.6452  -16.4736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0732  -16.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  6  0  0  0
  9  2  1  6  0  0  0
 10  3  1  1  0  0  0
 11  4  1  6  0  0  0
  5 12  1  0  0  0  0
  6 13  1  0  0  0  0
  7 13  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000625

> <DATABASE_NAME>
hmdb

> <SMILES>
OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H12O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-5,7-11H,1H2,(H,12,13)/t2-,3-,4+,5-/m1/s1

> <INCHI_KEY>
RGHNJXZEOKUKBD-SQOUGZDYSA-N

> <FORMULA>
C6H12O7

> <MOLECULAR_WEIGHT>
196.1553

> <EXACT_MASS>
196.058302738

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
17.148802962823897

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid

> <ALOGPS_LOGP>
-2.57

> <JCHEM_LOGP>
-3.4097443106666665

> <ALOGPS_LOGS>
-0.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.593710458724516

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.388205574321856

> <JCHEM_PKA_STRONGEST_BASIC>
-2.974220927705365

> <JCHEM_POLAR_SURFACE_AREA>
138.45000000000002

> <JCHEM_REFRACTIVITY>
38.27100000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.59e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gluconate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0000625 (Gluconic acid)

HMDB0000625
     RDKit          3D
Gluconic acid
 25 24  0  0  0  0  0  0  0  0999 V2000
    3.6956   -0.0617    1.4192 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5956   -0.4739    0.9694 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7514   -1.1292    1.8494 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1738   -0.2922   -0.4342 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2409    0.3674   -1.0906 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9210    0.5609   -0.5741 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7175    0.6694   -1.9739 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2928   -0.1346    0.0078 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4042   -1.4053   -0.5694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5558    0.6361   -0.3337 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4740    1.8921    0.2223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7755   -0.0604    0.1943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7480   -0.2007    1.5752 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5806   -0.7331    2.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0014   -1.2224   -0.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9173    1.1407   -1.6089 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0530    1.5784   -0.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7787   -0.2843   -2.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2472   -0.2529    1.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8161   -1.3337   -1.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5977    0.7092   -1.4268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3097    1.8432    1.1927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8617   -1.0869   -0.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6700    0.5266   -0.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6742   -0.1997    1.9317 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
  3 14  1  0
  4 15  1  6
  5 16  1  0
  6 17  1  1
  7 18  1  0
  8 19  1  1
  9 20  1  0
 10 21  1  6
 11 22  1  0
 12 23  1  0
 12 24  1  0
 13 25  1  0
M  END
Download

PDB for HMDB0000625 (Gluconic acid)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  O   UNK     0      41.471 -29.211   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      40.137 -33.061   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      42.804 -33.061   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      38.804 -29.211   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      45.471 -31.521   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      36.136 -30.751   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      37.470 -33.061   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      41.471 -30.751   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      40.137 -31.521   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      42.804 -31.521   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      38.804 -30.751   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      44.138 -30.751   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      37.470 -31.521   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4   11                                                            
CONECT    5   12                                                            
CONECT    6   13                                                            
CONECT    7   13                                                            
CONECT    8    1    9   10                                                  
CONECT    9    2    8   11                                                  
CONECT   10    3    8   12                                                  
CONECT   11    4    9   13                                                  
CONECT   12    5   10                                                       
CONECT   13    6    7   11                                                  
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END
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3D PDB for HMDB0000625 (Gluconic acid)

COMPND    HMDB0000625
HETATM    1  O1  UNL     1       3.696  -0.062   1.419  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.596  -0.474   0.969  1.00  0.00           C  
HETATM    3  O2  UNL     1       1.751  -1.129   1.849  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.174  -0.292  -0.434  1.00  0.00           C  
HETATM    5  O3  UNL     1       3.241   0.367  -1.091  1.00  0.00           O  
HETATM    6  C3  UNL     1       0.921   0.561  -0.574  1.00  0.00           C  
HETATM    7  O4  UNL     1       0.717   0.669  -1.974  1.00  0.00           O  
HETATM    8  C4  UNL     1      -0.293  -0.135   0.008  1.00  0.00           C  
HETATM    9  O5  UNL     1      -0.404  -1.405  -0.569  1.00  0.00           O  
HETATM   10  C5  UNL     1      -1.556   0.636  -0.334  1.00  0.00           C  
HETATM   11  O6  UNL     1      -1.474   1.892   0.222  1.00  0.00           O  
HETATM   12  C6  UNL     1      -2.775  -0.060   0.194  1.00  0.00           C  
HETATM   13  O7  UNL     1      -2.748  -0.201   1.575  1.00  0.00           O  
HETATM   14  H1  UNL     1       1.581  -0.733   2.778  1.00  0.00           H  
HETATM   15  H2  UNL     1       2.001  -1.222  -0.979  1.00  0.00           H  
HETATM   16  H3  UNL     1       2.917   1.141  -1.609  1.00  0.00           H  
HETATM   17  H4  UNL     1       1.053   1.578  -0.184  1.00  0.00           H  
HETATM   18  H5  UNL     1       0.779  -0.284  -2.297  1.00  0.00           H  
HETATM   19  H6  UNL     1      -0.247  -0.253   1.096  1.00  0.00           H  
HETATM   20  H7  UNL     1      -0.816  -1.334  -1.446  1.00  0.00           H  
HETATM   21  H8  UNL     1      -1.598   0.709  -1.427  1.00  0.00           H  
HETATM   22  H9  UNL     1      -1.310   1.843   1.193  1.00  0.00           H  
HETATM   23  H10 UNL     1      -2.862  -1.087  -0.257  1.00  0.00           H  
HETATM   24  H11 UNL     1      -3.670   0.527  -0.061  1.00  0.00           H  
HETATM   25  H12 UNL     1      -3.674  -0.200   1.932  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   14
CONECT    4    5    6   15
CONECT    5   16
CONECT    6    7    8   17
CONECT    7   18
CONECT    8    9   10   19
CONECT    9   20
CONECT   10   11   12   21
CONECT   11   22
CONECT   12   13   23   24
CONECT   13   25
END
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SMILES for HMDB0000625 (Gluconic acid)

OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O
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INCHI for HMDB0000625 (Gluconic acid)

InChI=1S/C6H12O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-5,7-11H,1H2,(H,12,13)/t2-,3-,4+,5-/m1/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(2R,3S,4R,5R)-2,3,4,5,6-Pentahydroxyhexanoic acidChEBI
D-Gluco-hexonic acidChEBI
D-GluconsaeureChEBI
D-GlukonsaeureChEBI
Dextronic acidChEBI
Glycogenic acidChEBI
Hexonic acidChEBI
Maltonic acidChEBI
D-GluconateKegg
(2R,3S,4R,5R)-2,3,4,5,6-PentahydroxyhexanoateGenerator
D-Gluco-hexonateGenerator
DextronateGenerator
GlycogenateGenerator
HexonateGenerator
MaltonateGenerator
D-Gluconic acidGenerator
GluconateGenerator
2,3,4,5,6-Pentahydroxy-hexanoateHMDB
2,3,4,5,6-Pentahydroxy-hexanoic acidHMDB
2,3,4,5,6-PentahydroxyhexanoateHMDB
2,3,4,5,6-Pentahydroxyhexanoic acidHMDB
GCOHMDB
GlosantoHMDB
GlyconateHMDB
Glyconic acidHMDB
PentahydroxycaproateHMDB
Pentahydroxycaproic acidHMDB
Boron gluconateHMDB
Gluconic acid, (113)indium-labeledHMDB
Gluconic acid, calcium saltHMDB
Gluconic acid, cesium(+3) saltHMDB
Gluconic acid, lanthanum(+3) saltHMDB
Gluconic acid, sodium saltHMDB
Gluconic acid, strontium (2:1) saltHMDB
MagnerotHMDB
Manganese gluconateHMDB
Sodium gluconateHMDB
Zinc gluconateHMDB
Gluconic acid, (159)dysprosium-labeled saltHMDB
Gluconic acid, aluminum (3:1) saltHMDB
Gluconic acid, ammonium saltHMDB
Gluconic acid, magnesium (2:1) saltHMDB
Gluconic acid, (14)C-labeledHMDB
Gluconic acid, 1-(14)C-labeledHMDB
Gluconic acid, 6-(14)C-labeledHMDB
Gluconic acid, cobalt (2:1) saltHMDB
Gluconic acid, copper saltHMDB
Gluconic acid, manganese (2:1) saltHMDB
Gluconic acid, potassium saltHMDB
Gluconic acid, tin(+2) saltHMDB
Gluconic acid, zinc saltHMDB
Lithium gluconateHMDB
Magnesium gluconateHMDB
Gluconic acid, (99)technecium (5+) saltHMDB
Gluconic acid, fe(+2) salt, dihydrateHMDB
Gluconic acid, monolithium saltHMDB
Gluconic acid, monopotassium saltHMDB
Gluconic acid, monosodium saltHMDB
Chemical FormulaC6H12O7
Average Molecular Weight196.1553
Monoisotopic Molecular Weight196.058302738
IUPAC Name(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid
Traditional Namegluconate
CAS Registry Number526-95-4
SMILES
OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O
InChI Identifier
InChI=1S/C6H12O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-5,7-11H,1H2,(H,12,13)/t2-,3-,4+,5-/m1/s1
InChI KeyRGHNJXZEOKUKBD-SQOUGZDYSA-N
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
  • Gluconic_acid
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Beta-hydroxy acid
  • Hydroxy fatty acid
  • Alpha-hydroxy acid
  • Fatty acyl
  • Fatty acid
  • Hydroxy acid
  • Monosaccharide
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Polyol
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Carbonyl group
  • Primary alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point113 - 118 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility316 mg/mL at 25 °CMERCK INDEX (1996)
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Astarita_neg131.730932474
[M-H]-Baker135.15630932474
[M+H]+Baker141.89230932474
[M-H]-Not Available132.9http://allccs.zhulab.cn/database/detail?ID=AllCCS00000412
[M+H]+Not Available141.892http://allccs.zhulab.cn/database/detail?ID=AllCCS00000412
Predicted Molecular Properties
PropertyValueSource
Water Solubility159 g/LALOGPS
logP-2.6ALOGPS
logP-3.4ChemAxon
logS-0.09ALOGPS
pKa (Strongest Acidic)3.39ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area138.45 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity38.27 m³·mol⁻¹ChemAxon
Polarizability17.15 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+144.25431661259
DarkChem[M-H]-137.5331661259
AllCCS[M+H]+143.86932859911
AllCCS[M-H]-134.09132859911
DeepCCS[M+H]+149.03730932474
DeepCCS[M-H]-146.64130932474
DeepCCS[M-2H]-179.8730932474
DeepCCS[M+Na]+154.9530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Gluconic acidOC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O3328.4Standard polar33892256
Gluconic acidOC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O1773.7Standard non polar33892256
Gluconic acidOC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O1797.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Gluconic acid,1TMS,isomer #1C[Si](C)(C)OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(=O)O1796.7Semi standard non polar33892256
Gluconic acid,1TMS,isomer #2C[Si](C)(C)O[C@H](CO)[C@@H](O)[C@H](O)[C@@H](O)C(=O)O1788.4Semi standard non polar33892256
Gluconic acid,1TMS,isomer #3C[Si](C)(C)O[C@H]([C@H](O)CO)[C@H](O)[C@@H](O)C(=O)O1752.9Semi standard non polar33892256
Gluconic acid,1TMS,isomer #4C[Si](C)(C)O[C@H]([C@@H](O)C(=O)O)[C@H](O)[C@H](O)CO1757.3Semi standard non polar33892256
Gluconic acid,1TMS,isomer #5C[Si](C)(C)O[C@@H](C(=O)O)[C@@H](O)[C@H](O)[C@H](O)CO1754.6Semi standard non polar33892256
Gluconic acid,1TMS,isomer #6C[Si](C)(C)OC(=O)[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO1778.3Semi standard non polar33892256
Gluconic acid,2TMS,isomer #1C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@@H](O)C(=O)O1868.4Semi standard non polar33892256
Gluconic acid,2TMS,isomer #10C[Si](C)(C)O[C@H]([C@H](O)CO)[C@H](O[Si](C)(C)C)[C@@H](O)C(=O)O1819.9Semi standard non polar33892256
Gluconic acid,2TMS,isomer #11C[Si](C)(C)O[C@@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H](O)CO1830.8Semi standard non polar33892256
Gluconic acid,2TMS,isomer #12C[Si](C)(C)OC(=O)[C@H](O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H](O)CO1835.9Semi standard non polar33892256
Gluconic acid,2TMS,isomer #13C[Si](C)(C)O[C@H]([C@@H](O[Si](C)(C)C)C(=O)O)[C@H](O)[C@H](O)CO1826.5Semi standard non polar33892256
Gluconic acid,2TMS,isomer #14C[Si](C)(C)OC(=O)[C@H](O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H](O)CO1825.1Semi standard non polar33892256
Gluconic acid,2TMS,isomer #15C[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H](O)CO1823.3Semi standard non polar33892256
Gluconic acid,2TMS,isomer #2C[Si](C)(C)OC[C@@H](O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](O)C(=O)O1836.6Semi standard non polar33892256
Gluconic acid,2TMS,isomer #3C[Si](C)(C)OC[C@@H](O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](O)C(=O)O1832.5Semi standard non polar33892256
Gluconic acid,2TMS,isomer #4C[Si](C)(C)OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C)C(=O)O1851.7Semi standard non polar33892256
Gluconic acid,2TMS,isomer #5C[Si](C)(C)OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(=O)O[Si](C)(C)C1857.7Semi standard non polar33892256
Gluconic acid,2TMS,isomer #6C[Si](C)(C)O[C@H]([C@@H](CO)O[Si](C)(C)C)[C@H](O)[C@@H](O)C(=O)O1849.6Semi standard non polar33892256
Gluconic acid,2TMS,isomer #7C[Si](C)(C)O[C@H]([C@@H](O)C(=O)O)[C@H](O)[C@@H](CO)O[Si](C)(C)C1840.6Semi standard non polar33892256
Gluconic acid,2TMS,isomer #8C[Si](C)(C)O[C@H](CO)[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C)C(=O)O1849.4Semi standard non polar33892256
Gluconic acid,2TMS,isomer #9C[Si](C)(C)OC(=O)[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O[Si](C)(C)C1850.8Semi standard non polar33892256
Gluconic acid,3TMS,isomer #1C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](O)C(=O)O1886.7Semi standard non polar33892256
Gluconic acid,3TMS,isomer #10C[Si](C)(C)OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C1883.7Semi standard non polar33892256
Gluconic acid,3TMS,isomer #11C[Si](C)(C)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O)C(=O)O1885.0Semi standard non polar33892256
Gluconic acid,3TMS,isomer #12C[Si](C)(C)O[C@@H]([C@H](O)[C@@H](O[Si](C)(C)C)C(=O)O)[C@@H](CO)O[Si](C)(C)C1903.9Semi standard non polar33892256
Gluconic acid,3TMS,isomer #13C[Si](C)(C)OC(=O)[C@H](O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C1895.8Semi standard non polar33892256
Gluconic acid,3TMS,isomer #14C[Si](C)(C)O[C@H]([C@@H](O[Si](C)(C)C)C(=O)O)[C@H](O)[C@@H](CO)O[Si](C)(C)C1891.7Semi standard non polar33892256
Gluconic acid,3TMS,isomer #15C[Si](C)(C)OC(=O)[C@H](O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](CO)O[Si](C)(C)C1897.5Semi standard non polar33892256
Gluconic acid,3TMS,isomer #16C[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@@H](CO)O[Si](C)(C)C1893.7Semi standard non polar33892256
Gluconic acid,3TMS,isomer #17C[Si](C)(C)O[C@H]([C@@H](O[Si](C)(C)C)C(=O)O)[C@H](O[Si](C)(C)C)[C@H](O)CO1874.5Semi standard non polar33892256
Gluconic acid,3TMS,isomer #18C[Si](C)(C)OC(=O)[C@H](O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)CO1878.4Semi standard non polar33892256
Gluconic acid,3TMS,isomer #19C[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H](O)CO1883.4Semi standard non polar33892256
Gluconic acid,3TMS,isomer #2C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](O)C(=O)O1890.1Semi standard non polar33892256
Gluconic acid,3TMS,isomer #20C[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H](O)CO1854.0Semi standard non polar33892256
Gluconic acid,3TMS,isomer #3C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C)C(=O)O1909.4Semi standard non polar33892256
Gluconic acid,3TMS,isomer #4C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@@H](O)C(=O)O[Si](C)(C)C1900.3Semi standard non polar33892256
Gluconic acid,3TMS,isomer #5C[Si](C)(C)OC[C@@H](O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O)C(=O)O1884.4Semi standard non polar33892256
Gluconic acid,3TMS,isomer #6C[Si](C)(C)OC[C@@H](O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C)C(=O)O1902.7Semi standard non polar33892256
Gluconic acid,3TMS,isomer #7C[Si](C)(C)OC[C@@H](O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](O)C(=O)O[Si](C)(C)C1898.4Semi standard non polar33892256
Gluconic acid,3TMS,isomer #8C[Si](C)(C)OC[C@@H](O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O1883.2Semi standard non polar33892256
Gluconic acid,3TMS,isomer #9C[Si](C)(C)OC[C@@H](O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C1892.5Semi standard non polar33892256
Gluconic acid,4TMS,isomer #1C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O)C(=O)O1919.5Semi standard non polar33892256
Gluconic acid,4TMS,isomer #10C[Si](C)(C)OC[C@@H](O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C1926.6Semi standard non polar33892256
Gluconic acid,4TMS,isomer #11C[Si](C)(C)O[C@H]([C@@H](O[Si](C)(C)C)C(=O)O)[C@H](O[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C1919.4Semi standard non polar33892256
Gluconic acid,4TMS,isomer #12C[Si](C)(C)OC(=O)[C@H](O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C1938.2Semi standard non polar33892256
Gluconic acid,4TMS,isomer #13C[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C1940.0Semi standard non polar33892256
Gluconic acid,4TMS,isomer #14C[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](CO)O[Si](C)(C)C1931.9Semi standard non polar33892256
Gluconic acid,4TMS,isomer #15C[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)CO1922.1Semi standard non polar33892256
Gluconic acid,4TMS,isomer #2C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C)C(=O)O1939.4Semi standard non polar33892256
Gluconic acid,4TMS,isomer #3C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](O)C(=O)O[Si](C)(C)C1948.7Semi standard non polar33892256
Gluconic acid,4TMS,isomer #4C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O1931.8Semi standard non polar33892256
Gluconic acid,4TMS,isomer #5C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C1936.2Semi standard non polar33892256
Gluconic acid,4TMS,isomer #6C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C1945.3Semi standard non polar33892256
Gluconic acid,4TMS,isomer #7C[Si](C)(C)OC[C@@H](O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O1928.6Semi standard non polar33892256
Gluconic acid,4TMS,isomer #8C[Si](C)(C)OC[C@@H](O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C1936.7Semi standard non polar33892256
Gluconic acid,4TMS,isomer #9C[Si](C)(C)OC[C@@H](O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C1943.0Semi standard non polar33892256
Gluconic acid,5TMS,isomer #1C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O1927.2Semi standard non polar33892256
Gluconic acid,5TMS,isomer #2C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C1942.2Semi standard non polar33892256
Gluconic acid,5TMS,isomer #3C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C1935.7Semi standard non polar33892256
Gluconic acid,5TMS,isomer #4C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C1931.0Semi standard non polar33892256
Gluconic acid,5TMS,isomer #5C[Si](C)(C)OC[C@@H](O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C1910.7Semi standard non polar33892256
Gluconic acid,5TMS,isomer #6C[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C1935.9Semi standard non polar33892256
Gluconic acid,6TMS,isomer #1C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C1983.7Semi standard non polar33892256
Gluconic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(=O)O2088.9Semi standard non polar33892256
Gluconic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H](CO)[C@@H](O)[C@H](O)[C@@H](O)C(=O)O2075.2Semi standard non polar33892256
Gluconic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@H]([C@H](O)CO)[C@H](O)[C@@H](O)C(=O)O2032.4Semi standard non polar33892256
Gluconic acid,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)O[C@H]([C@@H](O)C(=O)O)[C@H](O)[C@H](O)CO2021.7Semi standard non polar33892256
Gluconic acid,1TBDMS,isomer #5CC(C)(C)[Si](C)(C)O[C@@H](C(=O)O)[C@@H](O)[C@H](O)[C@H](O)CO2056.9Semi standard non polar33892256
Gluconic acid,1TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO2063.9Semi standard non polar33892256
Gluconic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@@H](O)C(=O)O2316.2Semi standard non polar33892256
Gluconic acid,2TBDMS,isomer #10CC(C)(C)[Si](C)(C)O[C@H]([C@H](O)CO)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O2267.6Semi standard non polar33892256
Gluconic acid,2TBDMS,isomer #11CC(C)(C)[Si](C)(C)O[C@@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)CO2303.5Semi standard non polar33892256
Gluconic acid,2TBDMS,isomer #12CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)CO2304.4Semi standard non polar33892256
Gluconic acid,2TBDMS,isomer #13CC(C)(C)[Si](C)(C)O[C@H]([C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O)[C@H](O)[C@H](O)CO2284.7Semi standard non polar33892256
Gluconic acid,2TBDMS,isomer #14CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](O)CO2293.5Semi standard non polar33892256
Gluconic acid,2TBDMS,isomer #15CC(C)(C)[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H](O)CO2298.2Semi standard non polar33892256
Gluconic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O)C(=O)O2288.5Semi standard non polar33892256
Gluconic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O2282.6Semi standard non polar33892256
Gluconic acid,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O2329.8Semi standard non polar33892256
Gluconic acid,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C2319.3Semi standard non polar33892256
Gluconic acid,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)O[C@H]([C@@H](CO)O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O)C(=O)O2311.2Semi standard non polar33892256
Gluconic acid,2TBDMS,isomer #7CC(C)(C)[Si](C)(C)O[C@H]([C@@H](O)C(=O)O)[C@H](O)[C@@H](CO)O[Si](C)(C)C(C)(C)C2291.1Semi standard non polar33892256
Gluconic acid,2TBDMS,isomer #8CC(C)(C)[Si](C)(C)O[C@H](CO)[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O2325.5Semi standard non polar33892256
Gluconic acid,2TBDMS,isomer #9CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O[Si](C)(C)C(C)(C)C2319.9Semi standard non polar33892256
Gluconic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O)C(=O)O2520.2Semi standard non polar33892256
Gluconic acid,3TBDMS,isomer #10CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2551.5Semi standard non polar33892256
Gluconic acid,3TBDMS,isomer #11CC(C)(C)[Si](C)(C)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O2532.1Semi standard non polar33892256
Gluconic acid,3TBDMS,isomer #12CC(C)(C)[Si](C)(C)O[C@@H]([C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O)[C@@H](CO)O[Si](C)(C)C(C)(C)C2578.3Semi standard non polar33892256
Gluconic acid,3TBDMS,isomer #13CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O[Si](C)(C)C(C)(C)C2575.3Semi standard non polar33892256
Gluconic acid,3TBDMS,isomer #14CC(C)(C)[Si](C)(C)O[C@H]([C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O)[C@H](O)[C@@H](CO)O[Si](C)(C)C(C)(C)C2566.0Semi standard non polar33892256
Gluconic acid,3TBDMS,isomer #15CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](CO)O[Si](C)(C)C(C)(C)C2577.8Semi standard non polar33892256
Gluconic acid,3TBDMS,isomer #16CC(C)(C)[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@@H](CO)O[Si](C)(C)C(C)(C)C2570.6Semi standard non polar33892256
Gluconic acid,3TBDMS,isomer #17CC(C)(C)[Si](C)(C)O[C@H]([C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)CO2534.1Semi standard non polar33892256
Gluconic acid,3TBDMS,isomer #18CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)CO2550.2Semi standard non polar33892256
Gluconic acid,3TBDMS,isomer #19CC(C)(C)[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)CO2555.9Semi standard non polar33892256
Gluconic acid,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O2532.8Semi standard non polar33892256
Gluconic acid,3TBDMS,isomer #20CC(C)(C)[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](O)CO2526.3Semi standard non polar33892256
Gluconic acid,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O2578.0Semi standard non polar33892256
Gluconic acid,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C2559.8Semi standard non polar33892256
Gluconic acid,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O2521.4Semi standard non polar33892256
Gluconic acid,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O2586.8Semi standard non polar33892256
Gluconic acid,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C2568.6Semi standard non polar33892256
Gluconic acid,3TBDMS,isomer #8CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O2562.1Semi standard non polar33892256
Gluconic acid,3TBDMS,isomer #9CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C2563.4Semi standard non polar33892256
Gluconic acid,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O2766.5Semi standard non polar33892256
Gluconic acid,4TBDMS,isomer #10CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2773.7Semi standard non polar33892256
Gluconic acid,4TBDMS,isomer #11CC(C)(C)[Si](C)(C)O[C@H]([C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O[Si](C)(C)C(C)(C)C2798.7Semi standard non polar33892256
Gluconic acid,4TBDMS,isomer #12CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O[Si](C)(C)C(C)(C)C2799.5Semi standard non polar33892256
Gluconic acid,4TBDMS,isomer #13CC(C)(C)[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O[Si](C)(C)C(C)(C)C2790.9Semi standard non polar33892256
Gluconic acid,4TBDMS,isomer #14CC(C)(C)[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](CO)O[Si](C)(C)C(C)(C)C2786.9Semi standard non polar33892256
Gluconic acid,4TBDMS,isomer #15CC(C)(C)[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)CO2762.0Semi standard non polar33892256
Gluconic acid,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O2821.6Semi standard non polar33892256
Gluconic acid,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C2802.6Semi standard non polar33892256
Gluconic acid,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O2810.2Semi standard non polar33892256
Gluconic acid,4TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C2802.1Semi standard non polar33892256
Gluconic acid,4TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2793.9Semi standard non polar33892256
Gluconic acid,4TBDMS,isomer #7CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O2803.2Semi standard non polar33892256
Gluconic acid,4TBDMS,isomer #8CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C2798.2Semi standard non polar33892256
Gluconic acid,4TBDMS,isomer #9CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2792.2Semi standard non polar33892256
Gluconic acid,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O3009.4Semi standard non polar33892256
Gluconic acid,5TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C3005.2Semi standard non polar33892256
Gluconic acid,5TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2991.5Semi standard non polar33892256
Gluconic acid,5TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2988.2Semi standard non polar33892256
Gluconic acid,5TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2988.3Semi standard non polar33892256
Gluconic acid,5TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O[Si](C)(C)C(C)(C)C2997.1Semi standard non polar33892256
Gluconic acid,6TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3213.8Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Placenta
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified<5 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified3.295 +/- 0.534 uMAdult (>18 years old)Both
Normal		 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
 details
SalivaDetected and Quantified45.49 +/- 24.12 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
 details
UrineDetected and Quantified13.3 (8.2-26.4) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified35.0+/-29.0 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified21.5 (8.1-38.8) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified63.463 +/- 28.036 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified3.732 +/- 0.687 uMAdult (>18 years old)Both
Schizophrenia		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Cryptosporidium infection		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
UrineDetected and Quantified65.277 +/- 47.794 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
Associated Disorders and Diseases
Disease References
Schizophrenia
  1. Koike S, Bundo M, Iwamoto K, Suga M, Kuwabara H, Ohashi Y, Shinoda K, Takano Y, Iwashiro N, Satomura Y, Nagai T, Natsubori T, Tada M, Yamasue H, Kasai K: A snapshot of plasma metabolites in first-episode schizophrenia: a capillary electrophoresis time-of-flight mass spectrometry study. Transl Psychiatry. 2014 Apr 8;4:e379. doi: 10.1038/tp.2014.19. [PubMed:24713860 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDDB13180
Phenol Explorer Compound IDNot Available
FooDB IDFDB001980
KNApSAcK IDC00007303
Chemspider ID10240
KEGG Compound IDC00257
BioCyc IDGLUCONATE
BiGG IDNot Available
Wikipedia LinkGluconic_acid
METLIN ID345
PubChem Compound10690
PDB IDNot Available
ChEBI ID33198
Food Biomarker OntologyNot Available
VMH IDGLCN
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceAnastassiadis, Savas; Morgunov, Igor G. Gluconic acid production. Recent Patents on Biotechnology (2007), 1(2), 167-180.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. Harkness RA, Purkiss P, Duffy S, Chalmers RA, Jones M: The effects of fetal energy depletion on amniotic fluid concentrations of amino acids, organic acids and related metabolites. J Inherit Metab Dis. 1988;11(1):103-13. [PubMed:3128683 ]
  3. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
  4. Rohatgi N, Nielsen TK, Bjorn SP, Axelsson I, Paglia G, Voldborg BG, Palsson BO, Rolfsson O: Biochemical characterization of human gluconokinase and the proposed metabolic impact of gluconic acid as determined by constraint based metabolic network analysis. PLoS One. 2014 Jun 4;9(6):e98760. doi: 10.1371/journal.pone.0098760. eCollection 2014. [PubMed:24896608 ]

Enzymes

Enzyme Details
1. Regucalcin
General function:
Involved in calcium ion binding
Specific function:
Gluconolactonase with low activity towards other sugar lactones, including gulonolactone and galactonolactone. Can also hydrolyze diisopropyl phosphorofluoridate and phenylacetate (in vitro). Calcium-binding protein. Modulates Ca(2+) signaling, and Ca(2+)-dependent cellular processes and enzyme activities (By similarity).
Gene Name:
RGN
Uniprot ID:
Q15493
Molecular weight:
33252.53
Reactions
Gluconolactone + Water → Gluconic aciddetails
Enzyme Details
2. Probable gluconokinase
General function:
Involved in shikimate kinase activity
Specific function:
Not Available
Gene Name:
IDNK
Uniprot ID:
Q5T6J7
Molecular weight:
20577.63
Reactions
Adenosine triphosphate + Gluconic acid → ADP + 6-Phosphogluconic aciddetails