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Showing NP-Card for D-Glucuronic acid (NP0001381)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2022-01-20 19:14:06 UTC
NP-MRD IDNP0001381
Secondary Accession NumbersNone
Natural Product Identification
Common NameD-Glucuronic acid
DescriptionGlucuronic acid is a carboxylic acid that has the structure of a glucose molecule that has had its sixth carbon atom (of six total) oxidized. The salts of glucuronic acid are known as glucuronates. Glucuronic acid is highly soluble in water. In humans, glucuronic acid is often linked to toxic or poisonous substances to allow for subsequent elimination, and to hormones to allow for easier transport. These linkages involve O-glycosidic bonds. The process is known as glucuronidation, and the resulting substances are known as glucuronides (or glucuronosides). Glucuronidation uses UDP-glucuronic acid (glucuronic acid linked via a glycosidic bond to uridine diphosphate) as an intermediate. UDP-glucuronic acid is formed in the liver of all animals.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001381 (D-Glucuronic acid)


  Mrv1652307152023542D          

 13 13  0  0  0  0            999 V2000
10000.0389 9999.3044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.037610000.1293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.7535 9998.8918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.0385 9997.6535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6093 9996.8284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1802 9999.3037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1802 9997.6535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6089 9999.3036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8945 9998.8911    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.8945 9998.0661    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.6089 9997.6538    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.3234 9998.0661    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.3234 9998.8911    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8  9  1  0  0  0  0
  8 13  1  0  0  0  0
 13  1  1  6  0  0  0
 12  4  1  1  0  0  0
 11  5  1  6  0  0  0
  9  6  1  1  0  0  0
 10  7  1  1  0  0  0
M  END
Download

3D MOL for NP0001381 (D-Glucuronic acid)

HMDB0000127
     RDKit          3D
D-Glucuronic acid
 23 23  0  0  0  0  0  0  0  0999 V2000
    2.6832    1.6808   -0.3715 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4606    0.4517   -0.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3375   -0.5096   -0.7436 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1944    0.0343    0.4138 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4496    1.1083    0.8242 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5310    1.4789   -0.0935 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1435    2.6343    0.4348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6025    0.4444   -0.2559 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5956    0.6081    0.7068 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9919   -0.9352   -0.0471 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6775   -1.8139   -0.8794 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4345   -0.8466   -0.5746 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0127   -2.1014   -0.6804 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2191   -0.6984   -0.2811 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4461   -0.5933    1.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0693    1.6655   -1.0744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4935    3.3832    0.4317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0394    0.5070   -1.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2673   -0.0969    0.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0236   -1.2342    1.0045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5135   -2.0720   -0.4409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4221   -0.3230   -1.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2889   -2.7720   -0.7060 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
  5  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
 12  4  1  0
  3 14  1  0
  4 15  1  1
  6 16  1  6
  7 17  1  0
  8 18  1  6
  9 19  1  0
 10 20  1  1
 11 21  1  0
 12 22  1  6
 13 23  1  0
M  END
Download

3D SDF for NP0001381 (D-Glucuronic acid)


  Mrv1652307152023542D          

 13 13  0  0  0  0            999 V2000
10000.0389 9999.3044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.037610000.1293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.7535 9998.8918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.0385 9997.6535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6093 9996.8284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1802 9999.3037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1802 9997.6535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6089 9999.3036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8945 9998.8911    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.8945 9998.0661    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.6089 9997.6538    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.3234 9998.0661    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.3234 9998.8911    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8  9  1  0  0  0  0
  8 13  1  0  0  0  0
 13  1  1  6  0  0  0
 12  4  1  1  0  0  0
 11  5  1  6  0  0  0
  9  6  1  1  0  0  0
 10  7  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0001381

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O7/c7-1-2(8)4(5(10)11)13-6(12)3(1)9/h1-4,6-9,12H,(H,10,11)/t1-,2-,3+,4-,6-/m0/s1

> <INCHI_KEY>
AEMOLEFTQBMNLQ-WAXACMCWSA-N

> <FORMULA>
C6H10O7

> <MOLECULAR_WEIGHT>
194.1394

> <EXACT_MASS>
194.042652674

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
16.324382634506076

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.30

> <JCHEM_LOGP>
-2.61226468

> <ALOGPS_LOGS>
0.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.309229286068723

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.207791058651709

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6863365702254773

> <JCHEM_POLAR_SURFACE_AREA>
127.45000000000002

> <JCHEM_REFRACTIVITY>
35.790800000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.95e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
glucuronic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0001381 (D-Glucuronic acid)

HMDB0000127
     RDKit          3D
D-Glucuronic acid
 23 23  0  0  0  0  0  0  0  0999 V2000
    2.6832    1.6808   -0.3715 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4606    0.4517   -0.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3375   -0.5096   -0.7436 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1944    0.0343    0.4138 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4496    1.1083    0.8242 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5310    1.4789   -0.0935 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1435    2.6343    0.4348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6025    0.4444   -0.2559 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5956    0.6081    0.7068 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9919   -0.9352   -0.0471 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6775   -1.8139   -0.8794 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4345   -0.8466   -0.5746 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0127   -2.1014   -0.6804 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2191   -0.6984   -0.2811 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4461   -0.5933    1.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0693    1.6655   -1.0744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4935    3.3832    0.4317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0394    0.5070   -1.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2673   -0.0969    0.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0236   -1.2342    1.0045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5135   -2.0720   -0.4409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4221   -0.3230   -1.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2889   -2.7720   -0.7060 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
  5  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
 12  4  1  0
  3 14  1  0
  4 15  1  1
  6 16  1  6
  7 17  1  0
  8 18  1  6
  9 19  1  0
 10 20  1  1
 11 21  1  0
 12 22  1  6
 13 23  1  0
M  END
Download

PDB for NP0001381 (D-Glucuronic acid)

HEADER    PROTEIN                                 15-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-JUL-20         0                                  
HETATM    1  C   UNK     0    8666.7398665.368   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8666.7378666.908   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8668.0738664.598   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8666.7388662.286   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8664.0718660.746   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8661.4038665.367   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8661.4038662.286   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8664.0708665.367   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    8662.7368664.597   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8662.7368663.057   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8664.0708662.287   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8665.4048663.057   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.4048664.597   0.000  0.00  0.00           C+0
CONECT    1    2    3   13                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4   12                                                            
CONECT    5   11                                                            
CONECT    6    9                                                            
CONECT    7   10                                                            
CONECT    8    9   13                                                       
CONECT    9   10    8    6                                                  
CONECT   10    9   11    7                                                  
CONECT   11   10   12    5                                                  
CONECT   12   11   13    4                                                  
CONECT   13   12    8    1                                                  
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END
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3D PDB for NP0001381 (D-Glucuronic acid)

COMPND    HMDB0000127
HETATM    1  O1  UNL     1       2.683   1.681  -0.371  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.461   0.452  -0.263  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.338  -0.510  -0.744  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.194   0.034   0.414  1.00  0.00           C  
HETATM    5  O3  UNL     1       0.450   1.108   0.824  1.00  0.00           O  
HETATM    6  C3  UNL     1      -0.531   1.479  -0.093  1.00  0.00           C  
HETATM    7  O4  UNL     1      -1.144   2.634   0.435  1.00  0.00           O  
HETATM    8  C4  UNL     1      -1.602   0.444  -0.256  1.00  0.00           C  
HETATM    9  O5  UNL     1      -2.596   0.608   0.707  1.00  0.00           O  
HETATM   10  C5  UNL     1      -0.992  -0.935  -0.047  1.00  0.00           C  
HETATM   11  O6  UNL     1      -1.678  -1.814  -0.879  1.00  0.00           O  
HETATM   12  C6  UNL     1       0.434  -0.847  -0.575  1.00  0.00           C  
HETATM   13  O7  UNL     1       1.013  -2.101  -0.680  1.00  0.00           O  
HETATM   14  H1  UNL     1       4.219  -0.698  -0.281  1.00  0.00           H  
HETATM   15  H2  UNL     1       1.446  -0.593   1.297  1.00  0.00           H  
HETATM   16  H3  UNL     1      -0.069   1.666  -1.074  1.00  0.00           H  
HETATM   17  H4  UNL     1      -0.494   3.383   0.432  1.00  0.00           H  
HETATM   18  H5  UNL     1      -2.039   0.507  -1.269  1.00  0.00           H  
HETATM   19  H6  UNL     1      -3.267  -0.097   0.536  1.00  0.00           H  
HETATM   20  H7  UNL     1      -1.024  -1.234   1.004  1.00  0.00           H  
HETATM   21  H8  UNL     1      -2.513  -2.072  -0.441  1.00  0.00           H  
HETATM   22  H9  UNL     1       0.422  -0.323  -1.537  1.00  0.00           H  
HETATM   23  H10 UNL     1       0.289  -2.772  -0.706  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   14
CONECT    4    5   12   15
CONECT    5    6
CONECT    6    7    8   16
CONECT    7   17
CONECT    8    9   10   18
CONECT    9   19
CONECT   10   11   12   20
CONECT   11   21
CONECT   12   13   22
CONECT   13   23
END
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SMILES for NP0001381 (D-Glucuronic acid)

O[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O
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INCHI for NP0001381 (D-Glucuronic acid)

InChI=1S/C6H10O7/c7-1-2(8)4(5(10)11)13-6(12)3(1)9/h1-4,6-9,12H,(H,10,11)/t1-,2-,3+,4-,6-/m0/s1
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View in JSmol
Synonyms
ValueSource
GlcAaChEBI
GlcAalphaChEBI
D-GlucuronateGenerator
alpha-D-Glucopyranuronic acidHMDB
alpha-D-Glucuronic acidHMDB
D-(+)-GlucuronateHMDB
D-(+)-Glucuronic acidHMDB
GCUHMDB
GlucosiduronateHMDB
Glucosiduronic acidHMDB
GlucuronateHMDB
Glucuronic acidHMDB
D-Glucopyranuronic acidHMDB
alpha-D-Glucopyranosyluronic acidHMDB
Α-D-glucopyranosyluronic acidHMDB
Α-D-glucopyranuronic acidHMDB
Chemical FormulaC6H10O7
Average Mass194.1394 Da
Monoisotopic Mass194.04265 Da
IUPAC Name(2S,3S,4S,5R,6S)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid
Traditional Nameglucuronic acid
CAS Registry Number6556-12-3
SMILES
O[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O
InChI Identifier
InChI=1S/C6H10O7/c7-1-2(8)4(5(10)11)13-6(12)3(1)9/h1-4,6-9,12H,(H,10,11)/t1-,2-,3+,4-,6-/m0/s1
InChI KeyAEMOLEFTQBMNLQ-WAXACMCWSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-01-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)v.dorna83@yahoo.comNot AvailableNot Available2021-08-11View Spectrum
Species
Species of Origin
Species NameSourceReference
Annona squamosaKNApSAcK Database
Gaultheria miquelianaKNApSAcK Database
Glycyrrhiza glabraLOTUS Database
Moringa oleiferaFooDB
Primula verisLOTUS Database
Prunus dulcisFooDB
Prunus persicaFooDB
Taraxacum officinaleFooDB
Zea mays L.FooDB
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
  • Beta-hydroxy acid
  • Hydroxy acid
  • Pyran
  • Monosaccharide
  • Oxane
  • Hemiacetal
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point143 - 144 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility485 mg/mLNot Available
LogP-2.57Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility295 g/LALOGPS
logP-2.3ALOGPS
logP-2.6ChemAxon
logS0.18ALOGPS
pKa (Strongest Acidic)3.21ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area127.45 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.79 m³·mol⁻¹ChemAxon
Polarizability16.32 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000127
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021897
KNApSAcK IDC00001123
Chemspider ID392615
KEGG Compound IDC00191
BioCyc IDNot Available
BiGG ID34196
Wikipedia LinkGlucuronic acid
METLIN ID161
PubChem Compound444791
PDB IDNot Available
ChEBI ID42717
Good Scents IDNot Available
References
General References
  1. Nishida T, Gatmaitan Z, Roy-Chowdhry J, Arias IM: Two distinct mechanisms for bilirubin glucuronide transport by rat bile canalicular membrane vesicles. Demonstration of defective ATP-dependent transport in rats (TR-) with inherited conjugated hyperbilirubinemia. J Clin Invest. 1992 Nov;90(5):2130-5. [PubMed:1430236 ]
  2. Jowett TP, Slater JD: A radioimmunoassay for the measurement of tetrahydroaldosterone 3-glucosiduronic acid in human plasma. Clin Chim Acta. 1981 Jan 22;109(2):133-44. [PubMed:7193539 ]
  3. Schmitt G, Aderjan R, Keller T, Wu M: Ethyl glucuronide: an unusual ethanol metabolite in humans. Synthesis, analytical data, and determination in serum and urine. J Anal Toxicol. 1995 Mar-Apr;19(2):91-4. [PubMed:7769794 ]
  4. Karasawa E: [Supplementary findings on urinary glucuronic acid excretion in pediatrics. I. Total glucuronic acid in 24-hour urine of normal infants determined by the modified Fishman's method with NaBH4]. Nihon Shonika Gakkai Zasshi. 1968 Aug 1;72(8):1122-7. [PubMed:5755643 ]
  5. Carpenter PC, Mattox VR: Isolation, determination of structure and synthesis of the acid-labile conjugate of aldosterone. Biochem J. 1976 Jul 1;157(1):1-14. [PubMed:962850 ]
  6. Raju U, Sklarew RJ, Post J, Levitz M: Steroid metabolism in human breast cancer cell lines. Steroids. 1978 Dec;32(5):669-80. [PubMed:734701 ]
  7. Stearns RA, Miller RR, Doss GA, Chakravarty PK, Rosegay A, Gatto GJ, Chiu SH: The metabolism of DuP 753, a nonpeptide angiotensin II receptor antagonist, by rat, monkey, and human liver slices. Drug Metab Dispos. 1992 Mar-Apr;20(2):281-7. [PubMed:1352222 ]
  8. Little JM, St Pyrek J, Lester R: Hepatic metabolism of 3 alpha-hydroxy-5 beta-etianic acid (3 alpha-hydroxy-5 beta-androstan-17 beta-carboxylic acid) in the adult rat. J Clin Invest. 1983 Jan;71(1):73-80. [PubMed:6848561 ]
  9. Pfeiffer E, Graf E, Gerstner S, Metzler M: Stimulation of estradiol glucuronidation: a protective mechanism against estradiol-mediated carcinogenesis? Mol Nutr Food Res. 2006 Apr;50(4-5):385-9. [PubMed:16598814 ]
  10. McDonagh AF, Palma LA, Lauff JJ, Wu TW: Origin of mammalian biliprotein and rearrangement of bilirubin glucuronides in vivo in the rat. J Clin Invest. 1984 Sep;74(3):763-70. [PubMed:6470139 ]
  11. Murano PS, Robichaud VY, Webb RE: Urinary excretion of sulfate and glucuronate conjugates in a free living population of adult males. Bull Environ Contam Toxicol. 1989 Jul;43(1):13-6. [PubMed:2758129 ]
  12. Tejero R, Bierbaum S, Douglas T, Reinstorf A, Worch H, Scharnweber D: Glucuronic acid and phosphoserine act as mineralization mediators of collagen I based biomimetic substrates. J Mater Sci Mater Med. 2010 Feb;21(2):407-18. doi: 10.1007/s10856-009-3879-x. Epub 2009 Nov 26. [PubMed:19941043 ]