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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (18) Show 18 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 14:58:03 UTC

HMDB ID

HMDB0000901

Secondary Accession Numbers

HMDB00901

Metabolite Identification

Common Name

Valproic acid glucuronide

Description

Valproic acid glucuronide is the glucuronidation product of valproic acid. Valproic acid, or 2-Propylpentanoic acid, is a chemical compound that has found clinical use as an anticonvulsant and mood-stabilizing drug, primarily in the treatment of epilepsy and bipolar disorder, but also used to treat migraine headaches and schizophrenia. In epileptics, valproic acid is used to control absence seizures, tonic-clonic seizures (grand mal), complex partial seizures, and the seizures associated with Lennox-Gastaut syndrome. Glucuronidation is a vital phase 2 metabolic (conjugative) process by which a wide range of drugs and other xenobiotics may be rendered water-soluble, detoxified and excreted. Acyl (ester) glucuronides (AGs) of carboxylic acids are potentially reactive metabolites. In particular, AGs are important phase 2 metabolites for a wide range of carboxylic acid-containing drugs. (PMID: 18201150 , 17496767 , 17496206 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0000901
     RDKit          3D
Valproic acid glucuronide
 46 46  0  0  0  0  0  0  0  0999 V2000
   -4.6989    1.7370   -0.7628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4240    1.5931    0.7377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9588    1.6066    1.0075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1203    0.6040    0.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2640   -0.8340    0.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5036   -1.5536    0.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1904   -3.0540    0.5046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6386    0.9134    0.5754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2880    1.9101    1.2467 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3508    0.1104    0.0497 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7197    0.3932    0.2553 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2760    0.6850   -0.9635 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6530    0.7383   -0.9742 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1238    1.3110   -2.2342 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2942    1.6764   -3.1283 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4631    1.4977   -2.5502 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1433   -0.6855   -0.7463 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4852   -0.8261   -0.9647 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7817   -0.9822    0.7108 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1410   -2.3111    1.0126 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3628   -0.7049    1.0243 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2307   -0.4663    2.4122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5569    2.4327   -0.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8160    2.0674   -1.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0128    0.7513   -1.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8258    2.5634    1.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9577    0.7482    1.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7534    1.6982    2.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6057    2.6354    0.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2226    0.8051   -0.7770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4373   -1.3259   -0.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9814   -1.1625    1.5929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3755   -1.2996    0.7906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7666   -1.5295   -0.8826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7496   -3.0384    1.5178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3862   -3.3264   -0.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0988   -3.6531    0.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7664    1.3142    0.8723 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9678    1.3909   -0.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9731    2.3429   -2.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5406   -1.3943   -1.3582 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6071   -1.4912   -1.7074 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4570   -0.3475    1.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4243   -2.4160    1.9455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7786   -1.6402    0.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0927    0.5163    2.5050 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  4  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  7 36  1  0
  7 37  1  0
 11 38  1  1
 13 39  1  1
 16 40  1  0
 17 41  1  6
 18 42  1  0
 19 43  1  1
 20 44  1  0
 21 45  1  1
 22 46  1  0
M  END


  Mrv0541 10181215142D          

 22 22  0  0  1  0            999 V2000
    5.9216   -9.0924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2303   -6.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6590   -8.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7072   -7.8988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4929   -6.7051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4447   -7.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4155  -10.5368    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1528  -10.1668    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7264  -10.0832    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.2011   -9.3433    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.9383   -8.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1338   -7.9824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7747   -9.2595    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.3672  -11.3604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8419  -10.6205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9891  -10.4531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6274   -9.4271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9866   -8.1498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8711   -7.6123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5120   -8.8896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0855   -8.8059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2785   -5.5115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  2  5  1  0  0  0  0
  3  4  1  0  0  0  0
  4  6  1  0  0  0  0
  5  6  1  0  0  0  0
  6 12  1  0  0  0  0
  7  9  1  0  0  0  0
  7 14  1  6  0  0  0
  7  8  1  0  0  0  0
  8 15  1  1  0  0  0
  8 10  1  0  0  0  0
  9 13  1  0  0  0  0
  9 16  1  1  0  0  0
 10 20  1  0  0  0  0
 10 11  1  6  0  0  0
 11 17  1  0  0  0  0
 11 18  2  0  0  0  0
 12 19  2  0  0  0  0
 12 21  1  0  0  0  0
 13 21  1  6  0  0  0
 13 20  1  0  0  0  0
 22  2  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000901

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H24O8/c1-3-5-7(6-4-2)13(20)22-14-10(17)8(15)9(16)11(21-14)12(18)19/h7-11,14-17H,3-6H2,1-2H3,(H,18,19)/t8-,9-,10+,11-,14-/m0/s1

> <INCHI_KEY>
XXKSYIHWRBBHIC-JVWRJRKNSA-N

> <FORMULA>
C14H24O8

> <MOLECULAR_WEIGHT>
320.3356

> <EXACT_MASS>
320.147117744

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
32.517595287103035

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-propylpentanoyl)oxy]oxane-2-carboxylic acid

> <ALOGPS_LOGP>
0.20

> <JCHEM_LOGP>
0.8506575156666667

> <ALOGPS_LOGS>
-1.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.212687196677269

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4090017108579356

> <JCHEM_PKA_STRONGEST_BASIC>
-3.686898691688546

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
72.5477

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.22e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-propylpentanoyl)oxy]oxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000901
     RDKit          3D
Valproic acid glucuronide
 46 46  0  0  0  0  0  0  0  0999 V2000
   -4.6989    1.7370   -0.7628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4240    1.5931    0.7377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9588    1.6066    1.0075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1203    0.6040    0.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2640   -0.8340    0.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5036   -1.5536    0.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1904   -3.0540    0.5046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6386    0.9134    0.5754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2880    1.9101    1.2467 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3508    0.1104    0.0497 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7197    0.3932    0.2553 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2760    0.6850   -0.9635 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6530    0.7383   -0.9742 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1238    1.3110   -2.2342 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2942    1.6764   -3.1283 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4631    1.4977   -2.5502 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1433   -0.6855   -0.7463 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4852   -0.8261   -0.9647 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7817   -0.9822    0.7108 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1410   -2.3111    1.0126 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3628   -0.7049    1.0243 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2307   -0.4663    2.4122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5569    2.4327   -0.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8160    2.0674   -1.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0128    0.7513   -1.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8258    2.5634    1.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9577    0.7482    1.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7534    1.6982    2.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6057    2.6354    0.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2226    0.8051   -0.7770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4373   -1.3259   -0.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9814   -1.1625    1.5929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3755   -1.2996    0.7906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7666   -1.5295   -0.8826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7496   -3.0384    1.5178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3862   -3.3264   -0.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0988   -3.6531    0.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7664    1.3142    0.8723 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9678    1.3909   -0.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9731    2.3429   -2.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5406   -1.3943   -1.3582 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6071   -1.4912   -1.7074 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4570   -0.3475    1.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4243   -2.4160    1.9455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7786   -1.6402    0.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0927    0.5163    2.5050 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  4  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  7 36  1  0
  7 37  1  0
 11 38  1  1
 13 39  1  1
 16 40  1  0
 17 41  1  6
 18 42  1  0
 19 43  1  1
 20 44  1  0
 21 45  1  1
 22 46  1  0
M  END

HEADER    PROTEIN                                 18-OCT-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-OCT-12         0                                  
HETATM    1  C   UNK     0      11.054 -16.972   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.363 -11.826   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.430 -16.282   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.520 -14.744   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.987 -12.516   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.897 -14.054   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.576 -19.669   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.952 -18.978   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.289 -18.822   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.042 -17.441   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      20.418 -16.750   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.183 -14.900   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.379 -17.284   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      17.485 -21.206   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      20.238 -19.825   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      14.913 -19.512   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      21.704 -17.597   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      20.508 -15.213   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      16.559 -14.210   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      17.756 -16.594   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      15.093 -16.438   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      15.453 -10.288   0.000  0.00  0.00           C+0
CONECT    1    3                                                            
CONECT    2    5   22                                                       
CONECT    3    1    4                                                       
CONECT    4    3    6                                                       
CONECT    5    2    6                                                       
CONECT    6    4    5   12                                                  
CONECT    7    9   14    8                                                  
CONECT    8    7   15   10                                                  
CONECT    9    7   13   16                                                  
CONECT   10    8   20   11                                                  
CONECT   11   10   17   18                                                  
CONECT   12    6   19   21                                                  
CONECT   13    9   21   20                                                  
CONECT   14    7                                                            
CONECT   15    8                                                            
CONECT   16    9                                                            
CONECT   17   11                                                            
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20   10   13                                                       
CONECT   21   12   13                                                       
CONECT   22    2                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

COMPND    HMDB0000901
HETATM    1  C1  UNL     1      -4.699   1.737  -0.763  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.424   1.593   0.738  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.959   1.607   1.008  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.120   0.604   0.350  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.264  -0.834   0.545  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.504  -1.554   0.196  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.190  -3.054   0.505  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.639   0.913   0.575  1.00  0.00           C  
HETATM    9  O1  UNL     1      -0.288   1.910   1.247  1.00  0.00           O  
HETATM   10  O2  UNL     1       0.351   0.110   0.050  1.00  0.00           O  
HETATM   11  C9  UNL     1       1.720   0.393   0.255  1.00  0.00           C  
HETATM   12  O3  UNL     1       2.276   0.685  -0.964  1.00  0.00           O  
HETATM   13  C10 UNL     1       3.653   0.738  -0.974  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.124   1.311  -2.234  1.00  0.00           C  
HETATM   15  O4  UNL     1       3.294   1.676  -3.128  1.00  0.00           O  
HETATM   16  O5  UNL     1       5.463   1.498  -2.550  1.00  0.00           O  
HETATM   17  C12 UNL     1       4.143  -0.685  -0.746  1.00  0.00           C  
HETATM   18  O6  UNL     1       5.485  -0.826  -0.965  1.00  0.00           O  
HETATM   19  C13 UNL     1       3.782  -0.982   0.711  1.00  0.00           C  
HETATM   20  O7  UNL     1       4.141  -2.311   1.013  1.00  0.00           O  
HETATM   21  C14 UNL     1       2.363  -0.705   1.024  1.00  0.00           C  
HETATM   22  O8  UNL     1       2.231  -0.466   2.412  1.00  0.00           O  
HETATM   23  H1  UNL     1      -5.557   2.433  -0.936  1.00  0.00           H  
HETATM   24  H2  UNL     1      -3.816   2.067  -1.313  1.00  0.00           H  
HETATM   25  H3  UNL     1      -5.013   0.751  -1.184  1.00  0.00           H  
HETATM   26  H4  UNL     1      -4.826   2.563   1.223  1.00  0.00           H  
HETATM   27  H5  UNL     1      -4.958   0.748   1.120  1.00  0.00           H  
HETATM   28  H6  UNL     1      -2.753   1.698   2.118  1.00  0.00           H  
HETATM   29  H7  UNL     1      -2.606   2.635   0.639  1.00  0.00           H  
HETATM   30  H8  UNL     1      -2.223   0.805  -0.777  1.00  0.00           H  
HETATM   31  H9  UNL     1      -1.437  -1.326  -0.078  1.00  0.00           H  
HETATM   32  H10 UNL     1      -1.981  -1.163   1.593  1.00  0.00           H  
HETATM   33  H11 UNL     1      -4.375  -1.300   0.791  1.00  0.00           H  
HETATM   34  H12 UNL     1      -3.767  -1.529  -0.883  1.00  0.00           H  
HETATM   35  H13 UNL     1      -2.750  -3.038   1.518  1.00  0.00           H  
HETATM   36  H14 UNL     1      -2.386  -3.326  -0.211  1.00  0.00           H  
HETATM   37  H15 UNL     1      -4.099  -3.653   0.408  1.00  0.00           H  
HETATM   38  H16 UNL     1       1.766   1.314   0.872  1.00  0.00           H  
HETATM   39  H17 UNL     1       3.968   1.391  -0.126  1.00  0.00           H  
HETATM   40  H18 UNL     1       5.973   2.343  -2.302  1.00  0.00           H  
HETATM   41  H19 UNL     1       3.541  -1.394  -1.358  1.00  0.00           H  
HETATM   42  H20 UNL     1       5.607  -1.491  -1.707  1.00  0.00           H  
HETATM   43  H21 UNL     1       4.457  -0.347   1.324  1.00  0.00           H  
HETATM   44  H22 UNL     1       4.424  -2.416   1.945  1.00  0.00           H  
HETATM   45  H23 UNL     1       1.779  -1.640   0.849  1.00  0.00           H  
HETATM   46  H24 UNL     1       2.093   0.516   2.505  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26   27
CONECT    3    4   28   29
CONECT    4    5    8   30
CONECT    5    6   31   32
CONECT    6    7   33   34
CONECT    7   35   36   37
CONECT    8    9    9   10
CONECT   10   11
CONECT   11   12   21   38
CONECT   12   13
CONECT   13   14   17   39
CONECT   14   15   15   16
CONECT   16   40
CONECT   17   18   19   41
CONECT   18   42
CONECT   19   20   21   43
CONECT   20   44
CONECT   21   22   45
CONECT   22   46
END

HMDB0000901
     RDKit          3D
Valproic acid glucuronide
 46 46  0  0  0  0  0  0  0  0999 V2000
   -4.6989    1.7370   -0.7628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4240    1.5931    0.7377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9588    1.6066    1.0075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1203    0.6040    0.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2640   -0.8340    0.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5036   -1.5536    0.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1904   -3.0540    0.5046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6386    0.9134    0.5754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2880    1.9101    1.2467 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3508    0.1104    0.0497 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7197    0.3932    0.2553 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2760    0.6850   -0.9635 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6530    0.7383   -0.9742 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1238    1.3110   -2.2342 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2942    1.6764   -3.1283 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4631    1.4977   -2.5502 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1433   -0.6855   -0.7463 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4852   -0.8261   -0.9647 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7817   -0.9822    0.7108 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1410   -2.3111    1.0126 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3628   -0.7049    1.0243 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2307   -0.4663    2.4122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5569    2.4327   -0.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8160    2.0674   -1.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0128    0.7513   -1.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8258    2.5634    1.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9577    0.7482    1.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7534    1.6982    2.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6057    2.6354    0.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2226    0.8051   -0.7770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4373   -1.3259   -0.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9814   -1.1625    1.5929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3755   -1.2996    0.7906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7666   -1.5295   -0.8826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7496   -3.0384    1.5178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3862   -3.3264   -0.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0988   -3.6531    0.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7664    1.3142    0.8723 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9678    1.3909   -0.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9731    2.3429   -2.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5406   -1.3943   -1.3582 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6071   -1.4912   -1.7074 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4570   -0.3475    1.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4243   -2.4160    1.9455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7786   -1.6402    0.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0927    0.5163    2.5050 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  4  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  7 36  1  0
  7 37  1  0
 11 38  1  1
 13 39  1  1
 16 40  1  0
 17 41  1  6
 18 42  1  0
 19 43  1  1
 20 44  1  0
 21 45  1  1
 22 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Valproate glucuronide	Generator
1-(2-Propylpentanoate	HMDB
1-(2-Propylpentanoate) beta-D-glucopyranuronate	HMDB
1-(2-Propylpentanoate) beta-D-glucopyranuronic acid	HMDB
1-(2-Propylpentanoate) beta-delta-glucopyranuronate	HMDB
1-(2-Propylpentanoate) beta-delta-glucopyranuronic acid	HMDB
1-(2-Propylpentanoic acid	HMDB
1-O-Valproyl-b-D-glucopyranuronic acid	HMDB
1-O-Valproyl-beta-delta-glucopyranuronic acid	HMDB
3,4,5-Trihydroxy-6-(2-propyl-pentanoyloxy)-tetrahydro-pyran-2-carboxylate	HMDB
3,4,5-Trihydroxy-6-(2-propyl-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid	HMDB
Dipropylacetate glucuronide	HMDB
Myproate	HMDB
Myproic acid	HMDB
Valproate	HMDB
Valproic acid	HMDB
VPA-g	HMDB
VPAG	HMDB

Chemical Formula

C₁₄H₂₄O₈

Average Molecular Weight

320.3356

Monoisotopic Molecular Weight

320.147117744

IUPAC Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-propylpentanoyl)oxy]oxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-propylpentanoyl)oxy]oxane-2-carboxylic acid

CAS Registry Number

60113-83-9

SMILES

CCCC(CCC)C(=O)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C14H24O8/c1-3-5-7(6-4-2)13(20)22-14-10(17)8(15)9(16)11(21-14)12(18)19/h7-11,14-17H,3-6H2,1-2H3,(H,18,19)/t8-,9-,10+,11-,14-/m0/s1

InChI Key

XXKSYIHWRBBHIC-JVWRJRKNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glucuronides

Alternative Parents

Substituents

1-o-glucuronide
O-glucuronide
Beta-hydroxy acid
Fatty acid ester
Dicarboxylic acid or derivatives
Hydroxy acid
Monosaccharide
Fatty acyl
Oxane
Pyran
Carboxylic acid ester
Secondary alcohol
Oxacycle
Acetal
Carboxylic acid
Polyol
Carboxylic acid derivative
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Tissue

Connective tissue

Adipose Tissue (HMDB: HMDB0000901)

Organ

Cell

Hematocyte

Platelet (HMDB: HMDB0000901)

Biofluid or Excreta

Non-excretory biofluid

Blood (HMDB: HMDB0000901)

Excreta

Urine (HMDB: HMDB0000901)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Valproic Acid Metabolism Pathway (PathBank: SMP0000635)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	0.85	Extrapolated

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	22.2 g/L	ALOGPS
logP	0.2	ALOGPS
logP	0.85	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	3.41	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	72.55 m³·mol⁻¹	ChemAxon
Polarizability	32.52 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	178.185	31661259
DarkChem	[M-H]-	174.494	31661259
AllCCS	[M+H]+	177.603	32859911
AllCCS	[M-H]-	174.222	32859911
DeepCCS	[M+H]+	182.037	30932474
DeepCCS	[M-H]-	179.641	30932474
DeepCCS	[M-2H]-	212.774	30932474
DeepCCS	[M+Na]+	187.977	30932474
AllCCS	[M+H]+	177.6	32859911
AllCCS	[M+H-H2O]+	174.7	32859911
AllCCS	[M+NH4]+	180.3	32859911
AllCCS	[M+Na]+	181.1	32859911
AllCCS	[M-H]-	174.2	32859911
AllCCS	[M+Na-2H]-	174.6	32859911
AllCCS	[M+HCOO]-	175.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Valproic acid glucuronide	CCCC(CCC)C(=O)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O	3259.3	Standard polar	33892256
Valproic acid glucuronide	CCCC(CCC)C(=O)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O	2222.8	Standard non polar	33892256
Valproic acid glucuronide	CCCC(CCC)C(=O)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O	2309.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Valproic acid glucuronide,1TMS,isomer #1	CCCC(CCC)C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	2217.1	Semi standard non polar	33892256
Valproic acid glucuronide,1TMS,isomer #2	CCCC(CCC)C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	2226.3	Semi standard non polar	33892256
Valproic acid glucuronide,1TMS,isomer #3	CCCC(CCC)C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	2206.4	Semi standard non polar	33892256
Valproic acid glucuronide,1TMS,isomer #4	CCCC(CCC)C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]1O	2197.7	Semi standard non polar	33892256
Valproic acid glucuronide,2TMS,isomer #1	CCCC(CCC)C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	2218.3	Semi standard non polar	33892256
Valproic acid glucuronide,2TMS,isomer #2	CCCC(CCC)C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	2247.8	Semi standard non polar	33892256
Valproic acid glucuronide,2TMS,isomer #3	CCCC(CCC)C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	2255.4	Semi standard non polar	33892256
Valproic acid glucuronide,2TMS,isomer #4	CCCC(CCC)C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	2256.7	Semi standard non polar	33892256
Valproic acid glucuronide,2TMS,isomer #5	CCCC(CCC)C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2247.1	Semi standard non polar	33892256
Valproic acid glucuronide,2TMS,isomer #6	CCCC(CCC)C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	2212.5	Semi standard non polar	33892256
Valproic acid glucuronide,3TMS,isomer #1	CCCC(CCC)C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	2290.7	Semi standard non polar	33892256
Valproic acid glucuronide,3TMS,isomer #2	CCCC(CCC)C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	2323.0	Semi standard non polar	33892256
Valproic acid glucuronide,3TMS,isomer #3	CCCC(CCC)C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2275.8	Semi standard non polar	33892256
Valproic acid glucuronide,3TMS,isomer #4	CCCC(CCC)C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2292.0	Semi standard non polar	33892256
Valproic acid glucuronide,4TMS,isomer #1	CCCC(CCC)C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2320.3	Semi standard non polar	33892256
Valproic acid glucuronide,1TBDMS,isomer #1	CCCC(CCC)C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O	2461.4	Semi standard non polar	33892256
Valproic acid glucuronide,1TBDMS,isomer #2	CCCC(CCC)C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	2468.3	Semi standard non polar	33892256
Valproic acid glucuronide,1TBDMS,isomer #3	CCCC(CCC)C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	2468.7	Semi standard non polar	33892256
Valproic acid glucuronide,1TBDMS,isomer #4	CCCC(CCC)C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]1O	2462.8	Semi standard non polar	33892256
Valproic acid glucuronide,2TBDMS,isomer #1	CCCC(CCC)C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O	2715.8	Semi standard non polar	33892256
Valproic acid glucuronide,2TBDMS,isomer #2	CCCC(CCC)C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	2710.9	Semi standard non polar	33892256
Valproic acid glucuronide,2TBDMS,isomer #3	CCCC(CCC)C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	2719.9	Semi standard non polar	33892256
Valproic acid glucuronide,2TBDMS,isomer #4	CCCC(CCC)C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	2730.3	Semi standard non polar	33892256
Valproic acid glucuronide,2TBDMS,isomer #5	CCCC(CCC)C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	2714.5	Semi standard non polar	33892256
Valproic acid glucuronide,2TBDMS,isomer #6	CCCC(CCC)C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	2721.8	Semi standard non polar	33892256
Valproic acid glucuronide,3TBDMS,isomer #1	CCCC(CCC)C(=O)O[C@@H]1O[C@H](C(=O)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]1O	2959.7	Semi standard non polar	33892256
Valproic acid glucuronide,3TBDMS,isomer #2	CCCC(CCC)C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	2994.6	Semi standard non polar	33892256
Valproic acid glucuronide,3TBDMS,isomer #3	CCCC(CCC)C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	2943.4	Semi standard non polar	33892256
Valproic acid glucuronide,3TBDMS,isomer #4	CCCC(CCC)C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	2966.7	Semi standard non polar	33892256
Valproic acid glucuronide,4TBDMS,isomer #1	CCCC(CCC)C(=O)O[C@@H]1O[C@H](C(=O)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]1O[Si](C)(C)C(C)(C)C	3200.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Valproic acid glucuronide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0pds-9221000000-c4a088ea62b38f27162d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Valproic acid glucuronide GC-MS (4 TMS) - 70eV, Positive	splash10-0006-7101290000-cfd964bab66e1a7f52c7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Valproic acid glucuronide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Valproic acid glucuronide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Valproic acid glucuronide GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Valproic acid glucuronide GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Valproic acid glucuronide GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Valproic acid glucuronide GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Valproic acid glucuronide GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Valproic acid glucuronide GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Valproic acid glucuronide GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Valproic acid glucuronide GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Valproic acid glucuronide GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Valproic acid glucuronide GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Valproic acid glucuronide GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Valproic acid glucuronide GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Valproic acid glucuronide GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Valproic acid glucuronide GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Valproic acid glucuronide GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Valproic acid glucuronide GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Valproic acid glucuronide GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Valproic acid glucuronide GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Valproic acid glucuronide GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Valproic acid glucuronide GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Valproic acid glucuronide GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valproic acid glucuronide 10V, Positive-QTOF	splash10-004j-0902000000-2aede4223010fbfa28cd	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valproic acid glucuronide 20V, Positive-QTOF	splash10-004j-4900000000-8d4033ca0760506b6c4e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valproic acid glucuronide 40V, Positive-QTOF	splash10-002e-9700000000-9b150785b1449fefe60e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valproic acid glucuronide 10V, Negative-QTOF	splash10-00mo-2913000000-c1208d610d940b866f24	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valproic acid glucuronide 20V, Negative-QTOF	splash10-002f-4910000000-881718af4775dafc78f3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valproic acid glucuronide 40V, Negative-QTOF	splash10-0006-9700000000-2d69130ba045cf068e49	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valproic acid glucuronide 10V, Positive-QTOF	splash10-00di-1209000000-1fe9a50772ce5d04154f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valproic acid glucuronide 20V, Positive-QTOF	splash10-0a4s-9301000000-7e6b8c6eaca54df62353	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valproic acid glucuronide 40V, Positive-QTOF	splash10-0a4r-9100000000-b293f27db4ba83db2396	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valproic acid glucuronide 10V, Negative-QTOF	splash10-014i-0109000000-980c74ef8113693a80e1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valproic acid glucuronide 20V, Negative-QTOF	splash10-00mp-3901000000-192aebcbdfefe9b795c9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valproic acid glucuronide 40V, Negative-QTOF	splash10-052e-9400000000-1078233b81443bce6776	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Adipose Tissue
Brain
Kidney
Liver
Pancreas
Placenta
Platelet

Pathways

Name	SMPDB/PathBank	KEGG
Valproic Acid Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022308

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

2991

PubChem Compound

88111

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Yamamura, Naotoshi; Muramatsu, Shigeki; Suzuki, Kanae; Uchiyama, Minoru; Nakajima, Eiichi. High-yield, enzymic synthesis of 14C- or 3H-labeled 1-O-valproyl-b-D-glucopyranuronic acid, the main metabolite of valproic acid in human. Radioisotopes (1999), 48(

Material Safety Data Sheet (MSDS)

Not Available

General References

Nemeroff CB: The role of GABA in the pathophysiology and treatment of anxiety disorders. Psychopharmacol Bull. 2003;37(4):133-46. [PubMed:15131523 ]
Bell EC, Willson MC, Wilman AH, Dave S, Silverstone PH: Differential effects of chronic lithium and valproate on brain activation in healthy volunteers. Hum Psychopharmacol. 2005 Aug;20(6):415-24. [PubMed:16106488 ]
Sztajnkrycer MD: Valproic acid toxicity: overview and management. J Toxicol Clin Toxicol. 2002;40(6):789-801. [PubMed:12475192 ]
Yoshida H, Hirozane K, Kimoto H, Hayashi T, Akiyama T, Katayama H, Watanabe M, Yoshitomi H, Kamiya A: Valproic acid elimination rate and urinary excretion of its glucuronide conjugate in patients with epilepsy. Biol Pharm Bull. 1999 Jul;22(7):716-20. [PubMed:10443469 ]
Seyfert S, Bernarding J, Braun J: Volume-selective 1H MR spectroscopy for in vivo detection of valproate in patients with epilepsy. Neuroradiology. 2003 May;45(5):295-9. Epub 2003 Mar 27. [PubMed:12669157 ]
Eyal S, Lamb JG, Smith-Yockman M, Yagen B, Fibach E, Altschuler Y, White HS, Bialer M: The antiepileptic and anticancer agent, valproic acid, induces P-glycoprotein in human tumour cell lines and in rat liver. Br J Pharmacol. 2006 Oct;149(3):250-60. Epub 2006 Aug 7. [PubMed:16894351 ]
Bailey DN, Briggs JR: Valproic acid binding to human serum and human placenta in vitro. Ther Drug Monit. 2005 Jun;27(3):375-7. [PubMed:15905810 ]
Safford KM, Hicok KC, Safford SD, Halvorsen YD, Wilkison WO, Gimble JM, Rice HE: Neurogenic differentiation of murine and human adipose-derived stromal cells. Biochem Biophys Res Commun. 2002 Jun 7;294(2):371-9. [PubMed:12051722 ]
Queizan A, Hernandez F, Rivas S: Pancreatic pseudocyst caused by valproic acid: case report and review of the literature. Eur J Pediatr Surg. 2003 Feb;13(1):60-2. [PubMed:12664419 ]
Loscher W: Basic pharmacology of valproate: a review after 35 years of clinical use for the treatment of epilepsy. CNS Drugs. 2002;16(10):669-94. [PubMed:12269861 ]
Fowler DW, Eadie MJ, Dickinson RG: Transplacental transfer and biotransformation studies of valproic acid and its glucuronide(s) in the perfused human placenta. J Pharmacol Exp Ther. 1989 Apr;249(1):318-23. [PubMed:2496226 ]
Serdaroglu G, Erhan E, Tekgul H, Oksel F, Erermis S, Uyar M, Tutuncuoglu S: Sodium valproate prophylaxis in childhood migraine. Headache. 2002 Sep;42(8):819-22. [PubMed:12390647 ]
Kim JM, Jung KY, Choi CM: Changes in brain complexity during valproate treatment in patients with partial epilepsy. Neuropsychobiology. 2002;45(2):106-12. [PubMed:11893868 ]
Huang YL, Hong HS, Wang ZW, Kuo TT: Fatal sodium valproate-induced hypersensitivity syndrome with lichenoid dermatitis and fulminant hepatitis. J Am Acad Dermatol. 2003 Aug;49(2):316-9. [PubMed:12894087 ]
Dickinson RG, Kluck RM, Hooper WD, Patterson M, Chalk JB, Eadie MJ: Rearrangement of valproate glucuronide in a patient with drug-associated hepatobiliary and renal dysfunction. Epilepsia. 1985 Nov-Dec;26(6):589-93. [PubMed:3935422 ]
Williams AM, Worrall S, de Jersey J, Dickinson RG: Studies on the reactivity of acyl glucuronides--III. Glucuronide-derived adducts of valproic acid and plasma protein and anti-adduct antibodies in humans. Biochem Pharmacol. 1992 Feb 18;43(4):745-55. [PubMed:1540228 ]
Nakamura H, Ushigome F, Koyabu N, Satoh S, Tsukimori K, Nakano H, Ohtani H, Sawada Y: Proton gradient-dependent transport of valproic acid in human placental brush-border membrane vesicles. Pharm Res. 2002 Feb;19(2):154-61. [PubMed:11883642 ]
De Berardis D, Campanella D, Matera V, Gambi F, La Rovere R, Sepede G, Grimaldi MR, Pacilli AM, Salerno RM, Ferro FM: Thrombocytopenia during valproic acid treatment in young patients with new-onset bipolar disorder. J Clin Psychopharmacol. 2003 Oct;23(5):451-8. [PubMed:14520121 ]
Anderson GD, Temkin NR, Chandler WL, Winn HR: Effect of valproate on hemostatic function in patients with traumatic brain injury. Epilepsy Res. 2003 Dec;57(2-3):111-9. [PubMed:15013052 ]
Mallet L, Babin S, Morais JA: Valproic acid-induced hyperammonemia and thrombocytopenia in an elderly woman. Ann Pharmacother. 2004 Oct;38(10):1643-7. Epub 2004 Aug 17. [PubMed:15316109 ]
Wong H, Tong V, Riggs KW, Rurak DW, Abbott FS, Kumar S: Kinetics of valproic acid glucuronidation: evidence for in vivo autoactivation. Drug Metab Dispos. 2007 Aug;35(8):1380-6. Epub 2007 May 11. [PubMed:17496206 ]
Gerstner T, Bell N, Konig S: Oral valproic acid for epilepsy--long-term experience in therapy and side effects. Expert Opin Pharmacother. 2008 Feb;9(2):285-92. doi: 10.1517/14656566.9.2.285 . [PubMed:18201150 ]
Russell S: Carnitine as an antidote for acute valproate toxicity in children. Curr Opin Pediatr. 2007 Apr;19(2):206-10. [PubMed:17496767 ]

Only showing the first 10 proteins. There are 18 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 2B28

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.
Gene Name:: UGT2B28
Uniprot ID:: Q9BY64
Molecular weight:: 38742.9

Enzyme Details

2. UDP-glucuronosyltransferase 2B4

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
Gene Name:: UGT2B4
Uniprot ID:: P06133
Molecular weight:: 60512.035

Enzyme Details

3. UDP-glucuronosyltransferase 1-4

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
Gene Name:: UGT1A4
Uniprot ID:: P22310
Molecular weight:: 60024.535

Enzyme Details

4. UDP-glucuronosyltransferase 2B7

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:: UGT2B7
Uniprot ID:: P16662
Molecular weight:: 60720.15

References

Ethell BT, Anderson GD, Burchell B: The effect of valproic acid on drug and steroid glucuronidation by expressed human UDP-glucuronosyltransferases. Biochem Pharmacol. 2003 May 1;65(9):1441-9. [PubMed:12732356 ]

Enzyme Details

5. UDP-glucuronosyltransferase 2B15

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xenobiotic substrates, including simple phenolic compounds, 7-hydroxylated coumarins, flavonoids, anthraquinones, and certain drugs and their hydroxylated metabolites. It also catalyzes the glucuronidation of endogenous estrogens and androgens.
Gene Name:: UGT2B15
Uniprot ID:: P54855
Molecular weight:: 61035.815

Enzyme Details

6. UDP-glucuronosyltransferase 2A1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Active on odorants and seems to be involved in olfaction; it could help clear lipophilic odorant molecules from the sensory epithelium.
Gene Name:: UGT2A1
Uniprot ID:: Q9Y4X1
Molecular weight:: 60771.605

Enzyme Details

7. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Enzyme Details

8. UDP-glucuronosyltransferase 1-9

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:: UGT1A9
Uniprot ID:: O60656
Molecular weight:: 59940.495

References

Ethell BT, Anderson GD, Burchell B: The effect of valproic acid on drug and steroid glucuronidation by expressed human UDP-glucuronosyltransferases. Biochem Pharmacol. 2003 May 1;65(9):1441-9. [PubMed:12732356 ]

Enzyme Details

9. UDP-glucuronosyltransferase 1-3

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:: UGT1A3
Uniprot ID:: P35503
Molecular weight:: 60337.835

Enzyme Details

10. UDP-glucuronosyltransferase 2B17

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. The major substrates of this isozyme are eugenol > 4-methylumbelliferone > dihydrotestosterone (DHT) > androstane-3-alpha,17-beta-diol (3-alpha-diol) > testosterone > androsterone (ADT).
Gene Name:: UGT2B17
Uniprot ID:: O75795
Molecular weight:: 61094.915

Only showing the first 10 proteins. There are 18 proteins in total.

Show all enzymes and transporters

Showing metabocard for Valproic acid glucuronide (HMDB0000901)

MOL for HMDB0000901 (Valproic acid glucuronide)

3D MOL for HMDB0000901 (Valproic acid glucuronide)

3D SDF for HMDB0000901 (Valproic acid glucuronide)

3D-SDF for HMDB0000901 (Valproic acid glucuronide)

PDB for HMDB0000901 (Valproic acid glucuronide)

3D PDB for HMDB0000901 (Valproic acid glucuronide)

SMILES for HMDB0000901 (Valproic acid glucuronide)

INCHI for HMDB0000901 (Valproic acid glucuronide)

Structure for HMDB0000901 (Valproic acid glucuronide)

3D Structure for HMDB0000901 (Valproic acid glucuronide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References