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Showing NP-Card for Glucaric acid (NP0001222)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-09 22:33:25 UTC
NP-MRD IDNP0001222
Secondary Accession NumbersNone
Natural Product Identification
Common NameGlucaric acid
DescriptionGlucaric acid, also known as glucarate or D-saccharic acid, belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid. Glucaric acid is a sugar acid derived from D-glucose in which both the aldehydic carbon atom and the carbon atom bearing the primary hydroxyl group are oxidized to carboxylic acid groups. D-glucaric acid is found in fruits, vegetables, and mammals. The highest concentrations of glucaric acid are found in grapefruits, apples, oranges, and cruciferous vegetables (PMID: 18772850 ). Glucaric acid is produced through the oxidation of glucose. Cytochrome P450 is thought to be responsible for the production of D-glucaric acid in vivo (PMID: 3779687 ). In mammals, D-glucaric acid and D-glucaro-l,4-lactone are also known end-products of the D-glucuronic acid pathway (PMID: 18772850 ). Glucaric is available as a dietary supplement in the form of calcium D-glucarate and has been studied for therapeutic purposes including cholesterol reduction and cancer chemotherapy (PMID: 9101079 ). D-Glucaric acid has a potential use as a building block for a number of polymers, including new nylons and hyperbranched polyesters. D-glucaric acid produced from D-glucose has been successfully utilized to produce a hydroxylated nylon.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001222 (Glucaric acid)


  Mrv1652309042000052D          

 14 13  0  0  0  0            999 V2000
 9992.3250 9992.8934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9993.0390 9992.4815    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9993.7546 9992.8934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9994.4701 9992.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.1836 9992.8934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.4701 9991.6561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9993.7546 9993.7182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9993.0390 9991.6561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.6103 9992.4815    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9990.8955 9992.8934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.1808 9992.4815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9990.8955 9993.7182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.6103 9991.6561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.3250 9993.7182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  1  0  0  0  0
  1 14  1  1  0  0  0
  2  3  1  0  0  0  0
  2  8  1  1  0  0  0
  3  4  1  0  0  0  0
  3  7  1  6  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  9 10  1  0  0  0  0
  9 13  1  1  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
Download

3D MOL for NP0001222 (Glucaric acid)

HMDB0000663
     RDKit          3D
Glucaric acid
 24 23  0  0  0  0  0  0  0  0999 V2000
   -3.5026    1.1306    1.4568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9640    0.3148    0.6543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5554   -0.9112    0.5094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7305    0.7217   -0.0832 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3754    2.0089    0.2697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6485   -0.2506    0.3020 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0096   -1.5472   -0.0550 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6887    0.1334   -0.3229 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6494    0.0802   -1.6933 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7958   -0.6786    0.2833 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6990   -2.0292   -0.0362 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0986   -0.1152   -0.1822 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9020   -0.8802   -0.7704 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3837    1.2048    0.0400 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4541   -1.4004   -0.3712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9389    0.7176   -1.1667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2085    2.5023    0.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5492   -0.2278    1.4076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0569   -1.6325   -1.0277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8666    1.1951   -0.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7653    0.9508   -2.1374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7219   -0.5996    1.3807 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3914   -2.2043   -0.9450 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0311    1.5166    0.7431 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  2  0
 12 14  1  0
  3 15  1  0
  4 16  1  6
  5 17  1  0
  6 18  1  1
  7 19  1  0
  8 20  1  6
  9 21  1  0
 10 22  1  1
 11 23  1  0
 14 24  1  0
M  END
Download

3D SDF for NP0001222 (Glucaric acid)


  Mrv1652309042000052D          

 14 13  0  0  0  0            999 V2000
 9992.3250 9992.8934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9993.0390 9992.4815    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9993.7546 9992.8934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9994.4701 9992.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.1836 9992.8934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.4701 9991.6561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9993.7546 9993.7182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9993.0390 9991.6561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.6103 9992.4815    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9990.8955 9992.8934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.1808 9992.4815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9990.8955 9993.7182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.6103 9991.6561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.3250 9993.7182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  1  0  0  0  0
  1 14  1  1  0  0  0
  2  3  1  0  0  0  0
  2  8  1  1  0  0  0
  3  4  1  0  0  0  0
  3  7  1  6  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  9 10  1  0  0  0  0
  9 13  1  1  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0001222

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O8/c7-1(3(9)5(11)12)2(8)4(10)6(13)14/h1-4,7-10H,(H,11,12)(H,13,14)/t1-,2-,3-,4+/m0/s1

> <INCHI_KEY>
DSLZVSRJTYRBFB-LLEIAEIESA-N

> <FORMULA>
C6H10O8

> <MOLECULAR_WEIGHT>
210.1388

> <EXACT_MASS>
210.037567296

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
16.8047219717019

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.77

> <JCHEM_LOGP>
-3.089469772666667

> <ALOGPS_LOGS>
-0.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.5410690508784013

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.828604159491

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7307040369214137

> <JCHEM_POLAR_SURFACE_AREA>
155.52

> <JCHEM_REFRACTIVITY>
38.13840000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.31e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
saccharic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0001222 (Glucaric acid)

HMDB0000663
     RDKit          3D
Glucaric acid
 24 23  0  0  0  0  0  0  0  0999 V2000
   -3.5026    1.1306    1.4568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9640    0.3148    0.6543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5554   -0.9112    0.5094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7305    0.7217   -0.0832 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3754    2.0089    0.2697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6485   -0.2506    0.3020 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0096   -1.5472   -0.0550 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6887    0.1334   -0.3229 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6494    0.0802   -1.6933 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7958   -0.6786    0.2833 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6990   -2.0292   -0.0362 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0986   -0.1152   -0.1822 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9020   -0.8802   -0.7704 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3837    1.2048    0.0400 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4541   -1.4004   -0.3712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9389    0.7176   -1.1667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2085    2.5023    0.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5492   -0.2278    1.4076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0569   -1.6325   -1.0277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8666    1.1951   -0.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7653    0.9508   -2.1374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7219   -0.5996    1.3807 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3914   -2.2043   -0.9450 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0311    1.5166    0.7431 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  2  0
 12 14  1  0
  3 15  1  0
  4 16  1  6
  5 17  1  0
  6 18  1  1
  7 19  1  0
  8 20  1  6
  9 21  1  0
 10 22  1  1
 11 23  1  0
 14 24  1  0
M  END
Download

PDB for NP0001222 (Glucaric 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  C   UNK     0    8652.3408653.401   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8653.6738652.632   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8655.0098653.401   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8656.3448652.632   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8657.6768653.401   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8656.3448651.091   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8655.0098654.941   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8653.6738651.091   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    8651.0068652.632   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8649.6728653.401   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8648.3378652.632   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8649.6728654.941   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8651.0068651.091   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    8652.3408654.941   0.000  0.00  0.00           O+0
CONECT    1    2    9   14                                                  
CONECT    2    1    3    8                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    3                                                            
CONECT    8    2                                                            
CONECT    9    1   10   13                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    9                                                            
CONECT   14    1                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END
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3D PDB for NP0001222 (Glucaric acid)

COMPND    HMDB0000663
HETATM    1  O1  UNL     1      -3.503   1.131   1.457  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.964   0.315   0.654  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.555  -0.911   0.509  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.730   0.722  -0.083  1.00  0.00           C  
HETATM    5  O3  UNL     1      -1.375   2.009   0.270  1.00  0.00           O  
HETATM    6  C3  UNL     1      -0.648  -0.251   0.302  1.00  0.00           C  
HETATM    7  O4  UNL     1      -1.010  -1.547  -0.055  1.00  0.00           O  
HETATM    8  C4  UNL     1       0.689   0.133  -0.323  1.00  0.00           C  
HETATM    9  O5  UNL     1       0.649   0.080  -1.693  1.00  0.00           O  
HETATM   10  C5  UNL     1       1.796  -0.679   0.283  1.00  0.00           C  
HETATM   11  O6  UNL     1       1.699  -2.029  -0.036  1.00  0.00           O  
HETATM   12  C6  UNL     1       3.099  -0.115  -0.182  1.00  0.00           C  
HETATM   13  O7  UNL     1       3.902  -0.880  -0.770  1.00  0.00           O  
HETATM   14  O8  UNL     1       3.384   1.205   0.040  1.00  0.00           O  
HETATM   15  H1  UNL     1      -3.454  -1.400  -0.371  1.00  0.00           H  
HETATM   16  H2  UNL     1      -1.939   0.718  -1.167  1.00  0.00           H  
HETATM   17  H3  UNL     1      -2.208   2.502   0.531  1.00  0.00           H  
HETATM   18  H4  UNL     1      -0.549  -0.228   1.408  1.00  0.00           H  
HETATM   19  H5  UNL     1      -1.057  -1.632  -1.028  1.00  0.00           H  
HETATM   20  H6  UNL     1       0.867   1.195  -0.029  1.00  0.00           H  
HETATM   21  H7  UNL     1       0.765   0.951  -2.137  1.00  0.00           H  
HETATM   22  H8  UNL     1       1.722  -0.600   1.381  1.00  0.00           H  
HETATM   23  H9  UNL     1       1.391  -2.204  -0.945  1.00  0.00           H  
HETATM   24  H10 UNL     1       4.031   1.517   0.743  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   15
CONECT    4    5    6   16
CONECT    5   17
CONECT    6    7    8   18
CONECT    7   19
CONECT    8    9   10   20
CONECT    9   21
CONECT   10   11   12   22
CONECT   11   23
CONECT   12   13   13   14
CONECT   14   24
END
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SMILES for NP0001222 (Glucaric acid)

O[C@@H]([C@H](O)[C@@H](O)C(O)=O)[C@H](O)C(O)=O
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INCHI for NP0001222 (Glucaric acid)

InChI=1S/C6H10O8/c7-1(3(9)5(11)12)2(8)4(10)6(13)14/h1-4,7-10H,(H,11,12)(H,13,14)/t1-,2-,3-,4+/m0/s1
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View in JSmol
Synonyms
ValueSource
D-(+)-Saccharic acidChEBI
D-Glucosaccharic acidChEBI
D-Saccharic acidChEBI
L-Gularic acidChEBI
Saccharic acidChEBI
D-Glucaric acidKegg
GlucarateKegg
D-(+)-SaccharateGenerator
D-GlucosaccharateGenerator
D-SaccharateGenerator
L-GularateGenerator
SaccharateGenerator
D-GlucarateGenerator
(2R,3S,4S,5S)-2,3,4,5-TetrahydroxyhexanedioateHMDB
(2R,3S,4S,5S)-2,3,4,5-Tetrahydroxyhexanedioic acidHMDB
D-TetrahydroxyadipateHMDB
D-Tetrahydroxyadipic acidHMDB
DL-Glucaric acidHMDB
GKRHMDB
Glucosaccharic acidHMDB
Tetrahydroxyadipic acidHMDB
Acid, saccharicHMDB
Anhydrous calcium glucarateHMDB
Anhydrous calcium saccharateHMDB
Calcium saccharateHMDB
Glucarate, calciumHMDB
Levo gularic acidHMDB
Levo-gularic acidHMDB
Tetrahydrate, calcium saccharateHMDB
Calcium glucarateHMDB
Calcium glucarate, anhydrousHMDB
Calcium saccharate anhydrousHMDB
Calcium saccharate, anhydrousHMDB
D Glucaric acidHMDB
Saccharate tetrahydrate, calciumHMDB
Saccharate, calciumHMDB
Calcium saccharate tetrahydrateHMDB
D Saccharic acidHMDB
Glucarate, anhydrous calciumHMDB
L Gularic acidHMDB
Saccharate, anhydrous calciumHMDB
Chemical FormulaC6H10O8
Average Mass210.1388 Da
Monoisotopic Mass210.03757 Da
IUPAC Name(2R,3S,4S,5S)-2,3,4,5-tetrahydroxyhexanedioic acid
Traditional Namesaccharic acid
CAS Registry Number25525-21-7
SMILES
O[C@@H]([C@H](O)[C@@H](O)C(O)=O)[C@H](O)C(O)=O
InChI Identifier
InChI=1S/C6H10O8/c7-1(3(9)5(11)12)2(8)4(10)6(13)14/h1-4,7-10H,(H,11,12)(H,13,14)/t1-,2-,3-,4+/m0/s1
InChI KeyDSLZVSRJTYRBFB-LLEIAEIESA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, 5%_DMSO, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 5%_DMSO, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Actinidia chinensisFooDB
Agaricus bisporusFooDB
AgaveFooDB
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosumFooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Aloysia triphyllaFooDB
AmaranthusFooDB
Amelanchier alnifoliaFooDB
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anethum graveolensFooDB
Angelica keiskeiFooDB
Annona cherimolaFooDB
Annona muricataFooDB
Annona reticulataFooDB
Annona squamosaFooDB
Anser anserFooDB
Anthriscus cerefoliumFooDB
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arabidopsis thalianaLOTUS Database
Arachis hypogaeaFooDB
Arctium lappaFooDB
Armoracia rusticanaFooDB
Artemisia dracunculusFooDB
Artemisia vulgarisFooDB
Artocarpus altilisFooDB
Artocarpus heterophyllusFooDB
Asparagus officinalisFooDB
Attalea speciosaFooDB
Auricularia auricula-judaeFooDB
Auricularia polytrichaFooDB
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Basella albaFooDB
Benincasa hispidaFooDB
Bertholletia excelsaFooDB
Beta vulgarisFooDB
Beta vulgaris ssp. ciclaFooDB
Bison bisonFooDB
Borago officinalisFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica alboglabraFooDB
Brassica junceaFooDB
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridisFooDB
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensisFooDB
Brassica rapa var. rapaFooDB
Brassica ruvoFooDB
Brosimum alicastrumFooDB
Bubalus bubalisFooDB
Byrsonima crassifoliaFooDB
Cajanus cajanFooDB
Canarium ovatumFooDB
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Capsicum annuum L.FooDB
Capsicum annuum var. annuumFooDB
Capsicum chinenseFooDB
Capsicum pubescensFooDB
Carica papaya L.FooDB
Carissa macrocarpaFooDB
Carthamus tinctoriusFooDB
Carum carviFooDB
CaryaFooDB
Carya illinoinensisFooDB
CastaneaFooDB
Castanea crenataFooDB
Castanea mollissimaFooDB
Castanea sativaFooDB
Ceratonia siliquaFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chamaemelum nobileFooDB
Chamerion angustifoliumFooDB
Chenopodium albumFooDB
Chenopodium quinoaFooDB
Chrysanthemum coronariumFooDB
Cicer arietinumFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
Cinnamomum aromaticumFooDB
Cinnamomum verumFooDB
CirsiumFooDB
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus latifoliaFooDB
Citrus limonFooDB
Citrus maximaFooDB
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colocasia esculentaFooDB
ColumbaFooDB
ColumbidaeFooDB
Corchorus olitoriusFooDB
Coriandrum sativum L.FooDB
CorylusFooDB
Corylus avellanaFooDB
Crateva religiosaFooDB
Crocus sativusFooDB
Cucumis meloFooDB
Cucumis metuliferusFooDB
Cucumis sativus L.FooDB
CucurbitaFooDB
Cucurbita maximaFooDB
Cucurbita moschataFooDB
Cuminum cyminumFooDB
Curcuma longaFooDB
Cydonia oblongaFooDB
Cymbopogon citratusFooDB
Cynara cardunculusFooDB
Cynara scolymusFooDB
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Dimocarpus longanFooDB
DioscoreaFooDB
Dioscorea pentaphyllaFooDB
DiospyrosFooDB
Diospyros kakiFooDB
Diospyros virginianaFooDB
Dromaius novaehollandiaeFooDB
Durio zibethinusFooDB
Dysphania ambrosioidesFooDB
ElaeisFooDB
Eleocharis dulcisFooDB
Elettaria cardamomumFooDB
Empetrum nigrumFooDB
Equus caballusFooDB
Eragrostis tefFooDB
Eriobotrya japonicaFooDB
Eruca vesicaria subsp. SativaFooDB
Eugenia javanicaFooDB
Eugenia unifloraFooDB
Eutrema japonicumFooDB
Fagopyrum esculentumFooDB
Fagopyrum tataricumFooDB
FagusFooDB
Feijoa sellowianaFooDB
Ficus caricaFooDB
Flammulina velutipesFooDB
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
Gallus gallusFooDB
Garcinia mangostanaFooDB
Gaylussacia baccataFooDB
Ginkgo bilobaFooDB
Glycine maxFooDB
GossypiumFooDB
Grifola frondosaFooDB
Hedysarum alpinumFooDB
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
Hibiscus sabbariffaFooDB
Hippophae rhamnoidesFooDB
Hordeum vulgareFooDB
Hyssopus officinalis L.FooDB
Illicium verumFooDB
Ipomoea aquaticaFooDB
Ipomoea batatasFooDB
JuglansFooDB
Juglans ailanthifoliaFooDB
Juglans cinereaFooDB
Juglans nigra L.FooDB
Juglans regiaFooDB
Lablab purpureusFooDB
Lactuca sativaFooDB
Lagenaria sicerariaFooDB
Lagopus mutaFooDB
Lathyrus sativusFooDB
Laurus nobilis L.FooDB
Lens culinarisFooDB
Lentinus edodesFooDB
Lepidium sativumFooDB
LeporidaeFooDB
Lepus timidusFooDB
Levisticum officinaleFooDB
Linum usitatissimumFooDB
Litchi chinensisFooDB
Lotus corniculatusLOTUS Database
Lotus glaberLOTUS Database
Luffa aegyptiacaFooDB
LupinusFooDB
Lupinus albusFooDB
MacadamiaFooDB
Macadamia tetraphyllaFooDB
Malpighia emarginataFooDB
MalusFooDB
Malus pumilaFooDB
Mammea americanaFooDB
Mangifera indicaFooDB
Manihot esculentaFooDB
Manilkara zapotaFooDB
Maranta arundinaceaFooDB
Matricaria recutitaFooDB
Matteuccia struthiopterisFooDB
Medicago sativaFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Melissa officinalis L.FooDB
MenthaFooDB
Mentha aquaticaFooDB
Mentha arvensisFooDB
Mentha spicataFooDB
Mentha x piperitaFooDB
Mespilus germanicaFooDB
Metroxylon saguFooDB
Momordica charantiaFooDB
MorchellaceaeFooDB
Morella rubraFooDB
Moringa oleiferaFooDB
MorusFooDB
Morus nigraFooDB
Musa acuminataFooDB
Musa x paradisiacaFooDB
MyricaFooDB
Myristica fragransFooDB
NelumboFooDB
Nelumbo nuciferaFooDB
Nephelium lappaceumFooDB
Numida meleagrisFooDB
Nuphar luteaFooDB
Ocimum basilicumFooDB
OdocoileusFooDB
Oenothera biennisFooDB
Olea europaeaFooDB
OpuntiaFooDB
Opuntia cochenilliferaFooDB
Opuntia macrorhizaFooDB
Origanum majoranaFooDB
Origanum onitesFooDB
Origanum vulgareFooDB
Origanum X majoricumFooDB
OryctolagusFooDB
Oryza rufipogonFooDB
Oryza sativaFooDB
Ovis ariesFooDB
Pachyrhizus erosusFooDB
Panax ginsengFooDB
Pangium eduleFooDB
Panicum miliaceumFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
Pediomelum esculentumFooDB
Perideridia oreganaFooDB
Persea americanaFooDB
Petasites japonicusFooDB
Petroselinum crispumFooDB
Phaseolus coccineusFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Phoenix dactyliferaFooDB
Photinia melanocarpaFooDB
Phyllostachys edulisFooDB
PhysalisFooDB
Physalis philadelphica var. immaculataFooDB
Phytolacca americanaFooDB
Pimenta dioicaFooDB
Pimpinella anisumFooDB
PinusFooDB
Pinus edulisFooDB
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
Pleurotus ostreatusFooDB
Pogostemon cablinLOTUS Database
Polygonum alpinumFooDB
Populus tremulaLOTUS Database
Portulaca oleraceaFooDB
Pouteria sapotaFooDB
Prunus armeniacaFooDB
Prunus aviumFooDB
Prunus avium L.FooDB
Prunus cerasusFooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Prunus persica var. persicaFooDB
Prunus tomentosaFooDB
Prunus virginianaFooDB
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Punica granatumFooDB
Pycnandra acuminataLOTUS Database
Pyrus communisFooDB
Pyrus pyrifoliaFooDB
QuercusFooDB
Raphanus sativusFooDB
Raphanus sativus var. longipinnatusFooDB
Raphanus sativus var. sativusFooDB
Rheum rhabarbarumFooDB
Ribes aureumFooDB
Ribes glandulosumFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
RosaFooDB
Rubus arcticusFooDB
Rubus chamaemorusFooDB
Rubus idaeusFooDB
Rubus occidentalisFooDB
Rubus spectabilisFooDB
RumexFooDB
Rumex acetosaFooDB
Rumex articusFooDB
Sagittaria latifoliaFooDB
Salix pulchraFooDB
Salvia elegansFooDB
Salvia hispanicaFooDB
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Satureja hortensis L.FooDB
Satureja montanaFooDB
Scorzonera hispanicaFooDB
Secale cerealeFooDB
Sechium eduleFooDB
Sesamum indicumFooDB
Sesbania bispinosaFooDB
Sinapis albaFooDB
SisymbriumFooDB
Solanum lycopersicumFooDB
Solanum lycopersicum var. cerasiformeFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaFooDB
Solanum quitoenseFooDB
Solanum tuberosumFooDB
Sorbus aucupariaFooDB
Sorghum bicolorFooDB
Spinacia oleraceaFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Syzygium aromaticumFooDB
Syzygium cuminiFooDB
Syzygium jambosFooDB
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
Tetragonia tetragonioidesFooDB
ThelespermaFooDB
Thymus pulegioidesFooDB
Thymus vulgarisFooDB
Tilia cordataFooDB
Tilia L.FooDB
Tragopogon porrifoliusFooDB
Trigonella foenum-graecumFooDB
TriticumFooDB
Triticum aestivumFooDB
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Trypanosoma bruceiLOTUS Database
Typha angustifoliaFooDB
VacciniumFooDB
Vaccinium angustifoliumFooDB
Vaccinium angustifolium X Vaccinium corymbosumFooDB
Vaccinium arboreumFooDB
Vaccinium corymbosumFooDB
Vaccinium deliciosumFooDB
Vaccinium elliottiiFooDB
Vaccinium macrocarponFooDB
Vaccinium myrtilloidesFooDB
Vaccinium myrtillusFooDB
Vaccinium ovalifoliumFooDB
Vaccinium ovatumFooDB
Vaccinium oxycoccosFooDB
Vaccinium parvifoliumFooDB
Vaccinium reticulatumFooDB
Vaccinium stamineumFooDB
Vaccinium uliginosumFooDB
Vaccinium vitis-idaeaFooDB
Valerianella locustaFooDB
VanillaFooDB
Verbena officinalisFooDB
Viburnum eduleFooDB
Vicia fabaFooDB
Vigna aconitifoliaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna umbellataFooDB
Vigna unguiculataFooDB
Vigna unguiculata ssp. cylindricaFooDB
Vigna unguiculata ssp. unguiculataFooDB
Vigna unguiculata var. sesquipedalisFooDB
VitisFooDB
Vitis aestivalisFooDB
Vitis labruscaFooDB
Vitis rotundifoliaFooDB
Vitis vinifera L.FooDB
Xanthosoma sagittifoliumFooDB
Zea mays L.FooDB
Zingiber officinaleFooDB
ZizaniaFooDB
Zizania aquaticaFooDB
Ziziphus zizyphusFooDB
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentGlucuronic acid derivatives
Alternative Parents
Substituents
  • Glucuronic acid or derivatives
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Beta-hydroxy acid
  • Hydroxy fatty acid
  • Monosaccharide
  • Hydroxy acid
  • Dicarboxylic acid or derivatives
  • Alpha-hydroxy acid
  • Fatty acyl
  • Fatty acid
  • Secondary alcohol
  • Polyol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility912 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility63.1 g/LALOGPS
logP-1.8ALOGPS
logP-3.1ChemAxon
logS-0.52ALOGPS
pKa (Strongest Acidic)2.83ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area155.52 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity38.14 m³·mol⁻¹ChemAxon
Polarizability16.8 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000663
DrugBank IDDB03603
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022169
KNApSAcK IDC00052287
Chemspider ID30577
KEGG Compound IDC00818
BioCyc IDD-GLUCARATE
BiGG ID35926
Wikipedia LinkSaccharic_acid
METLIN ID5633
PubChem Compound33037
PDB IDNot Available
ChEBI ID16002
Good Scents IDrw1736771
References
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. Matsushiro T, Suzuki N, Sato T, Maki T: Effects of diet on glucaric acid concentration in bile and the formation of calcium bilirubinate gallstones. Gastroenterology. 1977 Apr;72(4 Pt 1):630-3. [PubMed:320083 ]
  3. Roth B, Heimann G, Gladtke E: [Excretion of D-glucaric-acid in newborns with non-hemolytic hyperbilirubinemia after phenobarbital treatment (author's transl)]. Padiatr Padol. 1977;12(4):385-93. [PubMed:904946 ]
  4. Sorrell MF, Burnett DA, Tuma DJ, Barak AJ: Paradoxical urinary excretion of D-glucaric acid in acute viral hepatitis. Clin Pharmacol Ther. 1976 Sep;20(3):365-8. [PubMed:954355 ]
  5. Levy G, Khanna NN, Soda DM, Tsuzuki O, Stern L: Pharmacokinetics of acetaminophen in the human neonate: formation of acetaminophen glucuronide and sulfate in relation to plasma bilirubin concentration and D-glucaric acid excretion. Pediatrics. 1975 Jun;55(6):818-25. [PubMed:1134883 ]
  6. Traeger A, Horvath T, Rechenbach C, Javor T: Beta-adrenoceptor blocking drugs and cytochrome P-450: the influence of propranolol treatment on caffeine, antipyrine, D-glucaric acid and indocyanine green elimination in patients with hepatic disorders. Int J Clin Pharmacol Res. 1986;6(3):235-9. [PubMed:3744626 ]
  7. Herzberg M, Tenenbaum E, Fishel B, Wiener MH: D-Glucaric acid and gamma-glutamyltransferase as indices of hepatic enzyme induction in pregnancy. Clin Chem. 1977 Mar;23(3):596-8. [PubMed:13946 ]
  8. Zoltaszek R, Hanausek M, Kilianska ZM, Walaszek Z: [The biological role of D-glucaric acid and its derivatives: potential use in medicine]. Postepy Hig Med Dosw (Online). 2008 Sep 5;62:451-62. [PubMed:18772850 ]
  9. Marsh CA: Biosynthesis of D-glucaric acid in mammals: a free-radical mechanism? Carbohydr Res. 1986 Sep 15;153(1):119-31. doi: 10.1016/s0008-6215(00)90201-5. [PubMed:3779687 ]
  10. Walaszek Z, Szemraj J, Narog M, Adams AK, Kilgore J, Sherman U, Hanausek M: Metabolism, uptake, and excretion of a D-glucaric acid salt and its potential use in cancer prevention. Cancer Detect Prev. 1997;21(2):178-90. [PubMed:9101079 ]