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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (8) Show 8 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2020-02-26 21:41:05 UTC

HMDB ID

HMDB0015159

Secondary Accession Numbers

HMDB15159

Metabolite Identification

Common Name

Mycophenolic acid

Description

Mycophenolic acid, also known as mycophenolate or acide mycophenolique, belongs to the class of organic compounds known as phthalides. Phthalides are compounds containing a 3-hydrocarbylidene-2-benzofuran-1(3H)-one moiety,. Mycophenolic acid is a drug which is used for the prophylaxis of organ rejection in patients receiving allogeneic renal transplants, administered in combination with cyclosporine and corticosteroids. He became Vice President for the research. Mycophenolic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, mycophenolic acid participates in a number of enzymatic reactions. In particular, mycophenolic acid and uridine diphosphate glucuronic acid can be converted into mycophenolic acid O-acyl-glucuronide and uridine 5'-diphosphate through its interaction with the enzyme UDP-glucuronosyltransferase 2B7. In addition, mycophenolic acid and uridine diphosphate glucuronic acid can be converted into mycophenolic acid glucuronide and uridine 5'-diphosphate through its interaction with the enzymes UDP-glucuronosyltransferase 1-8 and UDP-glucuronosyltransferase 1-9. In humans, mycophenolic acid is involved in mycophenolic acid metabolism pathway. Mycophenolic acid is a potentially toxic compound.

Structure

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

HMDB0015159
     RDKit          3D
Mycophenolic acid
 43 44  0  0  0  0  0  0  0  0999 V2000
   -1.9470   -2.8362   -1.4613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0327   -1.4581   -1.7713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1661   -0.4724   -0.8179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4148   -0.0822   -0.4404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6106   -0.7203   -1.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6091    0.8899    0.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5367    1.4771    1.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2184    1.1161    0.7257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1911    1.7519    1.3526 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0415    0.1394   -0.2242 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2285   -0.3625   -0.7397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4520    0.3495   -0.5253 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5091   -0.1920    0.0542 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5059   -1.6075    0.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7474    0.6457    0.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8866    0.0329   -0.4948 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1409    0.8068   -0.3177 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1503    0.4449   -0.9724 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2307    1.9037    0.5398 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9892    2.4760    2.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2535    3.2045    2.7316 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3739    2.4685    2.0046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8231    1.4920    1.0829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4411   -3.1031   -0.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4657   -3.4335   -2.2356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8944   -3.1768   -1.4512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5740   -1.8387   -0.9012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7136   -0.4981   -2.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5500   -0.3910   -0.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7548    1.6456    1.2838 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0923   -0.5608   -1.8615 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3467   -1.4117   -0.3125 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5581    1.4003   -0.8681 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5412   -1.9633    0.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1789   -2.2299   -0.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8269   -1.7658    1.3822 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5891    1.6727   -0.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9324    0.6345    1.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6204    0.1550   -1.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1053   -1.0070   -0.2566 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2938    1.6889    1.5480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4264    0.7334    1.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4182    1.9815    0.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
  7 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 10  3  1  0
 23  6  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  5 28  1  0
  5 29  1  0
  9 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 19 41  1  0
 23 42  1  0
 23 43  1  0
M  END

1024
  Mrv0541 02231215112D          

 23 24  0  0  0  0            999 V2000
    9.7855   -0.1279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799   -0.9529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8089    1.5222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5603    1.3203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    0.6971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.5404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5234   -0.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944    0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5234    0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8089   -0.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944   -0.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8089    0.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799    0.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3041   -0.7918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3041    0.5360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8089   -1.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    1.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799   -1.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  1 15  1  0  0  0  0
  2 11  1  0  0  0  0
  2 22  1  0  0  0  0
  3 12  1  0  0  0  0
  4 15  2  0  0  0  0
  5 23  1  0  0  0  0
  6 23  2  0  0  0  0
  7  9  1  0  0  0  0
  7 10  2  0  0  0  0
  7 14  1  0  0  0  0
  8 11  2  0  0  0  0
  8 12  1  0  0  0  0
  8 13  1  0  0  0  0
  9 12  2  0  0  0  0
  9 15  1  0  0  0  0
 10 11  1  0  0  0  0
 10 17  1  0  0  0  0
 13 16  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 21  1  0  0  0  0
 19 20  1  0  0  0  0
 20 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015159

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(C\C=C(/C)CCC(O)=O)C(O)=C2C(=O)OCC2=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C17H20O6/c1-9(5-7-13(18)19)4-6-11-15(20)14-12(8-23-17(14)21)10(2)16(11)22-3/h4,20H,5-8H2,1-3H3,(H,18,19)/b9-4+

> <INCHI_KEY>
HPNSFSBZBAHARI-RUDMXATFSA-N

> <FORMULA>
C17H20O6

> <MOLECULAR_WEIGHT>
320.3371

> <EXACT_MASS>
320.125988372

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
32.94778056662982

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoic acid

> <ALOGPS_LOGP>
2.36

> <JCHEM_LOGP>
3.5275974476666656

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.758773469703659

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.574787977255424

> <JCHEM_PKA_STRONGEST_BASIC>
-4.068194505368491

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
85.2334

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.55e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
mycophenolic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015159
     RDKit          3D
Mycophenolic acid
 43 44  0  0  0  0  0  0  0  0999 V2000
   -1.9470   -2.8362   -1.4613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0327   -1.4581   -1.7713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1661   -0.4724   -0.8179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4148   -0.0822   -0.4404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6106   -0.7203   -1.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6091    0.8899    0.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5367    1.4771    1.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2184    1.1161    0.7257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1911    1.7519    1.3526 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0415    0.1394   -0.2242 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2285   -0.3625   -0.7397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4520    0.3495   -0.5253 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5091   -0.1920    0.0542 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5059   -1.6075    0.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7474    0.6457    0.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8866    0.0329   -0.4948 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1409    0.8068   -0.3177 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1503    0.4449   -0.9724 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2307    1.9037    0.5398 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9892    2.4760    2.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2535    3.2045    2.7316 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3739    2.4685    2.0046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8231    1.4920    1.0829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4411   -3.1031   -0.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4657   -3.4335   -2.2356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8944   -3.1768   -1.4512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5740   -1.8387   -0.9012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7136   -0.4981   -2.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5500   -0.3910   -0.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7548    1.6456    1.2838 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0923   -0.5608   -1.8615 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3467   -1.4117   -0.3125 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5581    1.4003   -0.8681 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5412   -1.9633    0.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1789   -2.2299   -0.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8269   -1.7658    1.3822 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5891    1.6727   -0.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9324    0.6345    1.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6204    0.1550   -1.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1053   -1.0070   -0.2566 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2938    1.6889    1.5480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4264    0.7334    1.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4182    1.9815    0.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
  7 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 10  3  1  0
 23  6  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  5 28  1  0
  5 29  1  0
  9 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 19 41  1  0
 23 42  1  0
 23 43  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1024                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      18.266  -0.239   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      11.909  -1.779   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      14.577   2.841   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      17.846   2.465   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       3.907   1.301   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       5.241  -1.009   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      15.910  -1.009   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.243   0.531   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.910   0.531   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.577  -1.779   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.243  -1.009   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.577   1.301   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.909   1.301   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.368  -1.478   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.368   1.001   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.576   0.531   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.577  -3.319   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.242   1.301   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.908   0.531   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.574   1.301   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.242   2.841   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.909  -3.319   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.241   0.531   0.000  0.00  0.00           C+0
CONECT    1   14   15                                                       
CONECT    2   11   22                                                       
CONECT    3   12                                                            
CONECT    4   15                                                            
CONECT    5   23                                                            
CONECT    6   23                                                            
CONECT    7    9   10   14                                                  
CONECT    8   11   12   13                                                  
CONECT    9    7   12   15                                                  
CONECT   10    7   11   17                                                  
CONECT   11    2    8   10                                                  
CONECT   12    3    8    9                                                  
CONECT   13    8   16                                                       
CONECT   14    1    7                                                       
CONECT   15    1    4    9                                                  
CONECT   16   13   18                                                       
CONECT   17   10                                                            
CONECT   18   16   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19   23                                                       
CONECT   21   18                                                            
CONECT   22    2                                                            
CONECT   23    5    6   20                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0015159
HETATM    1  C1  UNL     1      -1.947  -2.836  -1.461  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.033  -1.458  -1.771  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.166  -0.472  -0.818  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.415  -0.082  -0.440  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.611  -0.720  -1.055  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.609   0.890   0.502  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.537   1.477   1.073  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.218   1.116   0.726  1.00  0.00           C  
HETATM    9  O2  UNL     1      -0.191   1.752   1.353  1.00  0.00           O  
HETATM   10  C8  UNL     1      -1.042   0.139  -0.224  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.228  -0.363  -0.740  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.452   0.350  -0.525  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.509  -0.192   0.054  1.00  0.00           C  
HETATM   14  C12 UNL     1       2.506  -1.607   0.536  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.747   0.646   0.271  1.00  0.00           C  
HETATM   16  C14 UNL     1       4.887   0.033  -0.495  1.00  0.00           C  
HETATM   17  C15 UNL     1       6.141   0.807  -0.318  1.00  0.00           C  
HETATM   18  O3  UNL     1       7.150   0.445  -0.972  1.00  0.00           O  
HETATM   19  O4  UNL     1       6.231   1.904   0.540  1.00  0.00           O  
HETATM   20  C16 UNL     1      -2.989   2.476   2.026  1.00  0.00           C  
HETATM   21  O5  UNL     1      -2.253   3.204   2.732  1.00  0.00           O  
HETATM   22  O6  UNL     1      -4.374   2.469   2.005  1.00  0.00           O  
HETATM   23  C17 UNL     1      -4.823   1.492   1.083  1.00  0.00           C  
HETATM   24  H1  UNL     1      -2.441  -3.103  -0.501  1.00  0.00           H  
HETATM   25  H2  UNL     1      -2.466  -3.434  -2.236  1.00  0.00           H  
HETATM   26  H3  UNL     1      -0.894  -3.177  -1.451  1.00  0.00           H  
HETATM   27  H4  UNL     1      -4.574  -1.839  -0.901  1.00  0.00           H  
HETATM   28  H5  UNL     1      -4.714  -0.498  -2.123  1.00  0.00           H  
HETATM   29  H6  UNL     1      -5.550  -0.391  -0.561  1.00  0.00           H  
HETATM   30  H7  UNL     1       0.755   1.646   1.284  1.00  0.00           H  
HETATM   31  H8  UNL     1       0.092  -0.561  -1.862  1.00  0.00           H  
HETATM   32  H9  UNL     1       0.347  -1.412  -0.313  1.00  0.00           H  
HETATM   33  H10 UNL     1       1.558   1.400  -0.868  1.00  0.00           H  
HETATM   34  H11 UNL     1       3.541  -1.963   0.737  1.00  0.00           H  
HETATM   35  H12 UNL     1       2.179  -2.230  -0.345  1.00  0.00           H  
HETATM   36  H13 UNL     1       1.827  -1.766   1.382  1.00  0.00           H  
HETATM   37  H14 UNL     1       3.589   1.673  -0.114  1.00  0.00           H  
HETATM   38  H15 UNL     1       3.932   0.634   1.366  1.00  0.00           H  
HETATM   39  H16 UNL     1       4.620   0.155  -1.586  1.00  0.00           H  
HETATM   40  H17 UNL     1       5.105  -1.007  -0.257  1.00  0.00           H  
HETATM   41  H18 UNL     1       6.294   1.689   1.548  1.00  0.00           H  
HETATM   42  H19 UNL     1      -5.426   0.733   1.631  1.00  0.00           H  
HETATM   43  H20 UNL     1      -5.418   1.981   0.293  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4   10
CONECT    4    5    6
CONECT    5   27   28   29
CONECT    6    7    7   23
CONECT    7    8   20
CONECT    8    9   10   10
CONECT    9   30
CONECT   10   11
CONECT   11   12   31   32
CONECT   12   13   13   33
CONECT   13   14   15
CONECT   14   34   35   36
CONECT   15   16   37   38
CONECT   16   17   39   40
CONECT   17   18   18   19
CONECT   19   41
CONECT   20   21   21   22
CONECT   22   23
CONECT   23   42   43
END

HMDB0015159
     RDKit          3D
Mycophenolic acid
 43 44  0  0  0  0  0  0  0  0999 V2000
   -1.9470   -2.8362   -1.4613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0327   -1.4581   -1.7713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1661   -0.4724   -0.8179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4148   -0.0822   -0.4404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6106   -0.7203   -1.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6091    0.8899    0.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5367    1.4771    1.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2184    1.1161    0.7257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1911    1.7519    1.3526 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0415    0.1394   -0.2242 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2285   -0.3625   -0.7397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4520    0.3495   -0.5253 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5091   -0.1920    0.0542 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5059   -1.6075    0.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7474    0.6457    0.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8866    0.0329   -0.4948 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1409    0.8068   -0.3177 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1503    0.4449   -0.9724 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2307    1.9037    0.5398 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9892    2.4760    2.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2535    3.2045    2.7316 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3739    2.4685    2.0046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8231    1.4920    1.0829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4411   -3.1031   -0.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4657   -3.4335   -2.2356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8944   -3.1768   -1.4512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5740   -1.8387   -0.9012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7136   -0.4981   -2.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5500   -0.3910   -0.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7548    1.6456    1.2838 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0923   -0.5608   -1.8615 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3467   -1.4117   -0.3125 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5581    1.4003   -0.8681 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5412   -1.9633    0.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1789   -2.2299   -0.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8269   -1.7658    1.3822 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5891    1.6727   -0.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9324    0.6345    1.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6204    0.1550   -1.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1053   -1.0070   -0.2566 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2938    1.6889    1.5480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4264    0.7334    1.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4182    1.9815    0.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
  7 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 10  3  1  0
 23  6  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  5 28  1  0
  5 29  1  0
  9 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 19 41  1  0
 23 42  1  0
 23 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(e)-6-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoic acid	ChEBI
Acide mycophenolique	ChEBI
Acido micofenolico	ChEBI
Acidum mycophenolicum	ChEBI
Micofenolico acido	ChEBI
Mycophenolate	ChEBI
Mycophenolsaeure	ChEBI
(e)-6-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoate	Generator
Mycophenoic acid	HMDB
Acid, mycophenolic	HMDB
Cellcept	HMDB
Mofetil hydrochloride, mycophenolate	HMDB
Mofetil, mycophenolate	HMDB
Mycophenolate sodium	HMDB
Mycophenolate, sodium	HMDB
Sodium mycophenolate	HMDB
Mycophenolate mofetil	HMDB
Mycophenolate mofetil hydrochloride	HMDB
Mycophenolic acid morpholinoethyl ester	HMDB
Myfortic	HMDB

Chemical Formula

C₁₇H₂₀O₆

Average Molecular Weight

320.3371

Monoisotopic Molecular Weight

320.125988372

IUPAC Name

(4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoic acid

Traditional Name

mycophenolic acid

CAS Registry Number

24280-93-1

SMILES

COC1=C(C\C=C(/C)CCC(O)=O)C(O)=C2C(=O)OCC2=C1C

InChI Identifier

InChI=1S/C17H20O6/c1-9(5-7-13(18)19)4-6-11-15(20)14-12(8-23-17(14)21)10(2)16(11)22-3/h4,20H,5-8H2,1-3H3,(H,18,19)/b9-4+

InChI Key

HPNSFSBZBAHARI-RUDMXATFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phthalides. Phthalides are compounds containing a 3-hydrocarbylidene-2-benzofuran-1(3H)-one moiety,.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isocoumarans

Sub Class

Isobenzofuranones

Direct Parent

Phthalides

Alternative Parents

Substituents

Phthalide
Anisole
Medium-chain fatty acid
Alkyl aryl ether
Branched fatty acid
Methyl-branched fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Dicarboxylic acid or derivatives
Fatty acyl
Fatty acid
Benzenoid
Unsaturated fatty acid
Vinylogous acid
Carboxylic acid ester
Lactone
Ether
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

2-benzofurans (CHEBI:168396 )
monocarboxylic acid (CHEBI:168396 )
phenols (CHEBI:168396 )
gamma-lactone (CHEBI:168396 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	141 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.036 g/L	Not Available
LogP	2.8	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	165.369	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000991

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.036 g/L	ALOGPS
logP	2.36	ALOGPS
logP	3.53	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	3.57	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	85.23 m³·mol⁻¹	ChemAxon
Polarizability	32.95 Å³	ChemAxon
Number of Rings	2	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]+	175.418	31661259
DarkChem	[M-H]-	174.35	31661259
DeepCCS	[M+H]+	173.665	30932474
DeepCCS	[M-H]-	171.307	30932474
DeepCCS	[M-2H]-	205.339	30932474
DeepCCS	[M+Na]+	181.19	30932474
AllCCS	[M+H]+	175.2	32859911
AllCCS	[M+H-H2O]+	172.0	32859911
AllCCS	[M+NH4]+	178.1	32859911
AllCCS	[M+Na]+	179.0	32859911
AllCCS	[M-H]-	178.9	32859911
AllCCS	[M+Na-2H]-	179.0	32859911
AllCCS	[M+HCOO]-	179.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Mycophenolic acid	COC1=C(C\C=C(/C)CCC(O)=O)C(O)=C2C(=O)OCC2=C1C	4217.6	Standard polar	33892256
Mycophenolic acid	COC1=C(C\C=C(/C)CCC(O)=O)C(O)=C2C(=O)OCC2=C1C	2640.4	Standard non polar	33892256
Mycophenolic acid	COC1=C(C\C=C(/C)CCC(O)=O)C(O)=C2C(=O)OCC2=C1C	2803.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Mycophenolic acid,1TMS,isomer #1	COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C/C=C(\C)CCC(=O)O[Si](C)(C)C	2616.1	Semi standard non polar	33892256
Mycophenolic acid,1TMS,isomer #2	COC1=C(C)C2=C(C(=O)OC2)C(O[Si](C)(C)C)=C1C/C=C(\C)CCC(=O)O	2690.8	Semi standard non polar	33892256
Mycophenolic acid,2TMS,isomer #1	COC1=C(C)C2=C(C(=O)OC2)C(O[Si](C)(C)C)=C1C/C=C(\C)CCC(=O)O[Si](C)(C)C	2703.9	Semi standard non polar	33892256
Mycophenolic acid,1TBDMS,isomer #1	COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C/C=C(\C)CCC(=O)O[Si](C)(C)C(C)(C)C	2841.3	Semi standard non polar	33892256
Mycophenolic acid,1TBDMS,isomer #2	COC1=C(C)C2=C(C(=O)OC2)C(O[Si](C)(C)C(C)(C)C)=C1C/C=C(\C)CCC(=O)O	2914.9	Semi standard non polar	33892256
Mycophenolic acid,2TBDMS,isomer #1	COC1=C(C)C2=C(C(=O)OC2)C(O[Si](C)(C)C(C)(C)C)=C1C/C=C(\C)CCC(=O)O[Si](C)(C)C(C)(C)C	3158.1	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 - Mycophenolic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0bvm-0091000000-bb41ce2ccd5996f6c67c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mycophenolic acid GC-MS (2 TMS) - 70eV, Positive	splash10-002b-3128900000-5379558b00ac276e7fc2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mycophenolic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mycophenolic acid LC-ESI-ITFT , negative-QTOF	splash10-002r-0490000000-99420edc8894323b59c3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mycophenolic acid LC-ESI-ITFT , negative-QTOF	splash10-014i-0009000000-b99d88ff2ddeb6977c4a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mycophenolic acid LC-ESI-ITFT , negative-QTOF	splash10-014i-0149000000-ed6b854b4f9af495c8d8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mycophenolic acid LC-ESI-ITFT , negative-QTOF	splash10-0006-0972000000-12d0e80f109d1fa6eb11	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mycophenolic acid LC-ESI-ITFT , negative-QTOF	splash10-0006-0950000000-2e6c3543fe3f9f4e0790	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mycophenolic acid LC-ESI-ITFT , negative-QTOF	splash10-0006-0930000000-e7a74fbe76e7141ec5f3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mycophenolic acid LC-ESI-ITFT , negative-QTOF	splash10-022c-0910000000-27f7c0023a8b7e5b4d66	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mycophenolic acid LC-ESI-ITFT , negative-QTOF	splash10-014i-0009000000-4aba5ee4ba77899b36fb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mycophenolic acid LC-ESI-ITFT , negative-QTOF	splash10-014i-0149000000-497b49ab395f3319c943	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mycophenolic acid LC-ESI-ITFT , negative-QTOF	splash10-0006-0971000000-68634f04b665bb0e68a3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mycophenolic acid LC-ESI-ITFT , negative-QTOF	splash10-0006-0950000000-37f2ee0320d2ec560b93	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mycophenolic acid LC-ESI-ITFT , negative-QTOF	splash10-0f6x-0930000000-500359a3fd82c686ff99	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mycophenolic acid LC-ESI-ITFT , negative-QTOF	splash10-006x-0900000000-6d04c3395aae26f88529	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mycophenolic acid LC-ESI-ITFT , negative-QTOF	splash10-002r-0590000000-fe2f27357ba775714c5a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mycophenolic acid LC-ESI-ITFT , negative-QTOF	splash10-014i-0009000000-8f75c9bc48b5eb019974	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mycophenolic acid LC-ESI-ITFT , negative-QTOF	splash10-014i-0009000000-57a06531623d00c32d13	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mycophenolic acid LC-ESI-ITFT , negative-QTOF	splash10-002r-0490000000-700501110e03f998e99b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mycophenolic acid LC-ESI-ITFT , negative-QTOF	splash10-002r-0490000000-d857a6e047fc52e09e65	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mycophenolic acid LC-ESI-QFT , negative-QTOF	splash10-014i-0659000000-ba96d820001d9e786c8d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mycophenolic acid 45V, Negative-QTOF	splash10-0006-0971000000-68634f04b665bb0e68a3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mycophenolic acid 35V, Negative-QTOF	splash10-014i-0559000000-5d1229819b582c483b43	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mycophenolic acid 60V, Negative-QTOF	splash10-0006-0950000000-37f2ee0320d2ec560b93	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mycophenolic acid 75V, Negative-QTOF	splash10-0f6x-0930000000-500359a3fd82c686ff99	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mycophenolic acid 30V, Negative-QTOF	splash10-014i-0149000000-2cca0f75c30a5b601440	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mycophenolic acid 30V, Negative-QTOF	splash10-014i-0149000000-ed6b854b4f9af495c8d8	2021-09-20	HMDB team, MONA	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Mycophenolic 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	Taking drug identified by DrugBank entry DB01024	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01024	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01024

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

393865

KEGG Compound ID

C20380

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Mycophenolic_acid

METLIN ID

Not Available

PubChem Compound

446541

PDB ID

MOA

ChEBI ID

168396

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Woodroffe R, Yao GL, Meads C, Bayliss S, Ready A, Raftery J, Taylor RS: Clinical and cost-effectiveness of newer immunosuppressive regimens in renal transplantation: a systematic review and modelling study. Health Technol Assess. 2005 May;9(21):1-179, iii-iv. [PubMed:15899149 ]

Enzymes

Enzyme Details

1. 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

Dostalek M, Court MH, Hazarika S, Akhlaghi F: Diabetes mellitus reduces activity of human UDP-glucuronosyltransferase 2B7 in liver and kidney leading to decreased formation of mycophenolic acid acyl-glucuronide metabolite. Drug Metab Dispos. 2011 Mar;39(3):448-55. doi: 10.1124/dmd.110.036608. Epub 2010 Dec 1. [PubMed:21123165 ]
Picard N, Ratanasavanh D, Premaud A, Le Meur Y, Marquet P: Identification of the UDP-glucuronosyltransferase isoforms involved in mycophenolic acid phase II metabolism. Drug Metab Dispos. 2005 Jan;33(1):139-46. Epub 2004 Oct 6. [PubMed:15470161 ]

Enzyme Details

2. 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

References

Dostalek M, Court MH, Hazarika S, Akhlaghi F: Diabetes mellitus reduces activity of human UDP-glucuronosyltransferase 2B7 in liver and kidney leading to decreased formation of mycophenolic acid acyl-glucuronide metabolite. Drug Metab Dispos. 2011 Mar;39(3):448-55. doi: 10.1124/dmd.110.036608. Epub 2010 Dec 1. [PubMed:21123165 ]
Miles KK, Kessler FK, Smith PC, Ritter JK: Characterization of rat intestinal microsomal UDP-glucuronosyltransferase activity toward mycophenolic acid. Drug Metab Dispos. 2006 Sep;34(9):1632-9. Epub 2006 Jun 21. [PubMed:16790558 ]

Enzyme Details

3. 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

Dostalek M, Court MH, Hazarika S, Akhlaghi F: Diabetes mellitus reduces activity of human UDP-glucuronosyltransferase 2B7 in liver and kidney leading to decreased formation of mycophenolic acid acyl-glucuronide metabolite. Drug Metab Dispos. 2011 Mar;39(3):448-55. doi: 10.1124/dmd.110.036608. Epub 2010 Dec 1. [PubMed:21123165 ]
Picard N, Ratanasavanh D, Premaud A, Le Meur Y, Marquet P: Identification of the UDP-glucuronosyltransferase isoforms involved in mycophenolic acid phase II metabolism. Drug Metab Dispos. 2005 Jan;33(1):139-46. Epub 2004 Oct 6. [PubMed:15470161 ]

Enzyme Details

4. UDP-glucuronosyltransferase 1-6

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:: UGT1A6
Uniprot ID:: P19224
Molecular weight:: 60750.215

References

Miles KK, Kessler FK, Smith PC, Ritter JK: Characterization of rat intestinal microsomal UDP-glucuronosyltransferase activity toward mycophenolic acid. Drug Metab Dispos. 2006 Sep;34(9):1632-9. Epub 2006 Jun 21. [PubMed:16790558 ]

Enzyme Details

5. UDP-glucuronosyltransferase 1-7

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:: UGT1A7
Uniprot ID:: Q9HAW7
Molecular weight:: 59818.315

References

Miles KK, Kessler FK, Smith PC, Ritter JK: Characterization of rat intestinal microsomal UDP-glucuronosyltransferase activity toward mycophenolic acid. Drug Metab Dispos. 2006 Sep;34(9):1632-9. Epub 2006 Jun 21. [PubMed:16790558 ]

Enzyme Details

6. Inosine-5'-monophosphate dehydrogenase 2

General function:: Involved in catalytic activity
Specific function:: Catalyzes the conversion of inosine 5'-phosphate (IMP) to xanthosine 5'-phosphate (XMP), the first committed and rate-limiting step in the de novo synthesis of guanine nucleotides, and therefore plays an important role in the regulation of cell growth. Could also have a single-stranded nucleic acid-binding activity and could play a role in RNA and/or DNA metabolism. It may also have a role in the development of malignancy and the growth progression of some tumors.
Gene Name:: IMPDH2
Uniprot ID:: P12268
Molecular weight:: 55804.495

References

Vannozzi F, Filipponi F, Di Paolo A, Danesi R, Urbani L, Bocci G, Catalano G, De Simone P, Mosca F, Del Tacca M: An exploratory study on pharmacogenetics of inosine-monophosphate dehydrogenase II in peripheral mononuclear cells from liver-transplant recipients. Transplant Proc. 2004 Nov;36(9):2787-90. [PubMed:15621150 ]
Wang J, Zeevi A, Webber S, Girnita DM, Addonizio L, Selby R, Hutchinson IV, Burckart GJ: A novel variant L263F in human inosine 5'-monophosphate dehydrogenase 2 is associated with diminished enzyme activity. Pharmacogenet Genomics. 2007 Apr;17(4):283-90. [PubMed:17496727 ]
Penuelas S, Noe V, Morales R, Ciudad CJ: Sensitization of human erythroleukemia K562 cells resistant to methotrexate by inhibiting IMPDH. Med Sci Monit. 2005 Jan;11(1):BR6-12. [PubMed:15614187 ]
Yam P, Jensen M, Akkina R, Anderson J, Villacres MC, Wu J, Zaia JA, Yee JK: Ex vivo selection and expansion of cells based on expression of a mutated inosine monophosphate dehydrogenase 2 after HIV vector transduction: effects on lymphocytes, monocytes, and CD34+ stem cells. Mol Ther. 2006 Aug;14(2):236-44. Epub 2006 May 2. [PubMed:16647299 ]
Dzidic A, Prgomet C, Mohr A, Meyer K, Bauer J, Meyer HH, Pfaffl MW: Effects of mycophenolic acid on inosine monophosphate dehydrogenase I and II mRNA expression in white blood cells and various tissues in sheep. J Vet Med A Physiol Pathol Clin Med. 2006 May;53(4):163-9. [PubMed:16629948 ]
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

7. Inosine-5'-monophosphate dehydrogenase 1

General function:: Involved in catalytic activity
Specific function:: Catalyzes the conversion of inosine 5'-phosphate (IMP) to xanthosine 5'-phosphate (XMP), the first committed and rate-limiting step in the de novo synthesis of guanine nucleotides, and therefore plays an important role in the regulation of cell growth. Could also have a single-stranded nucleic acid-binding activity and could play a role in RNA and/or DNA metabolism. It may also have a role in the development of malignancy and the growth progression of some tumors.
Gene Name:: IMPDH1
Uniprot ID:: P20839
Molecular weight:: 63252.24

References

Dzidic A, Prgomet C, Mohr A, Meyer K, Bauer J, Meyer HH, Pfaffl MW: Effects of mycophenolic acid on inosine monophosphate dehydrogenase I and II mRNA expression in white blood cells and various tissues in sheep. J Vet Med A Physiol Pathol Clin Med. 2006 May;53(4):163-9. [PubMed:16629948 ]

Enzyme Details

8. Mycophenolic acid acyl-glucuronide esterase, mitochondrial

General function:: Not Available
Specific function:: Catalyzes the deglucuronidation of mycophenolic acid acyl-glucuronide, a metabolite of the immunosuppressant drug mycophenolate.
Gene Name:: ABHD10
Uniprot ID:: Q9NUJ1
Molecular weight:: 33932.165

Reactions

Mycophenolic acid O-acyl-glucuronide + Water → Mycophenolic acid + D-Glucuronic acid	details

Showing metabocard for Mycophenolic acid (HMDB0015159)

MOL for HMDB0015159 (Mycophenolic acid)

3D MOL for HMDB0015159 (Mycophenolic acid)

3D SDF for HMDB0015159 (Mycophenolic acid)

3D-SDF for HMDB0015159 (Mycophenolic acid)

PDB for HMDB0015159 (Mycophenolic acid)

3D PDB for HMDB0015159 (Mycophenolic acid)

SMILES for HMDB0015159 (Mycophenolic acid)

INCHI for HMDB0015159 (Mycophenolic acid)

Structure for HMDB0015159 (Mycophenolic acid)

3D Structure for HMDB0015159 (Mycophenolic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

References

Reactions