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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (9) Show 9 proteins XML

enzymes (9) Show 9 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:45 UTC

HMDB ID

HMDB0014826

Secondary Accession Numbers

HMDB14826

Metabolite Identification

Common Name

Mycophenolate mofetil

Description

Mycophenolate mofetil is only found in individuals that have used or taken this drug. It is the 2-morpholinoethyl ester of mycophenolic acid (MPA), an immunosuppressive agent, inosine monophosphate dehydrogenase (IMPDH) inhibitor.Mycophenolate mofetil is hydrolyzed to form mycophenolic acid (MPA), which is the active metabolite. MPA is a potent, selective, uncompetitive, and reversible inhibitor of inosine monophosphate dehydrogenase (IMPDH), and therefore inhibits the de novo pathway of guanosine nucleotide synthesis without incorporation into DNA. Because T- and B-lymphocytes are critically dependent for their proliferation on de novo synthesis of purines, whereas other cell types can utilize salvage pathways, MPA has potent cytostatic effects on lymphocytes. MPA inhibits proliferative responses of T- and B-lymphocytes to both mitogenic and allospecific stimulation. Addition of guanosine or deoxyguanosine reverses the cytostatic effects of MPA on lymphocytes. MPA also suppresses antibody formation by B-lymphocytes. MPA prevents the glycosylation of lymphocyte and monocyte glycoproteins that are involved in intercellular adhesion to endothelial cells and may inhibit recruitment of leukocytes into sites of inflammation and graft rejection. Mycophenolate mofetil did not inhibit early events in the activation of human peripheral blood mononuclear cells, such as the production of interleukin-1 (IL-1) and interleukin-2 (IL-2), but did block the coupling of these events to DNA synthesis and proliferation.

Structure

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

688
  Mrv0541 02231214562D          

 31 33  0  0  0  0            999 V2000
    1.6500   -0.5404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9150   -0.1279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.6971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5094   -0.9529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9383    1.5222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6898    1.3203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.5404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.2846    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6529   -0.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2239    0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6529    0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9383   -0.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2239   -0.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9383    0.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5094    0.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4335   -0.7918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949    0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4335    0.5360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    0.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9383   -1.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    1.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5094   -1.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  1 13  1  0  0  0  0
  2 22  1  0  0  0  0
  2 24  1  0  0  0  0
  3 18  1  0  0  0  0
  3 29  1  0  0  0  0
  4 19  1  0  0  0  0
  4 31  1  0  0  0  0
  5 20  1  0  0  0  0
  6 24  2  0  0  0  0
  7 29  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  0  0  0  0
 10 13  1  0  0  0  0
 11 18  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  2  0  0  0  0
 14 22  1  0  0  0  0
 15 19  2  0  0  0  0
 15 20  1  0  0  0  0
 15 21  1  0  0  0  0
 16 20  2  0  0  0  0
 16 24  1  0  0  0  0
 17 19  1  0  0  0  0
 17 27  1  0  0  0  0
 21 23  1  0  0  0  0
 23 26  2  0  0  0  0
 25 26  1  0  0  0  0
 25 28  1  0  0  0  0
 26 30  1  0  0  0  0
 28 29  1  0  0  0  0
M  END

HMDB0014826
     RDKit          3D
Mycophenolate mofetil
 62 64  0  0  0  0  0  0  0  0999 V2000
   -3.9512    2.2017    0.8314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3565    1.3993   -0.2356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6633    0.0604   -0.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9843   -0.2530    0.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9972    0.7904    0.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3597   -1.5757    0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4299   -2.5606    0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1180   -2.2469   -0.2846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2373   -3.2938   -0.5173 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7429   -0.9007   -0.3907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3353   -0.7135   -0.8013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8472    0.6287   -0.9702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8012    1.1278   -0.3248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0233    0.3417    0.6510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3846    2.5606   -0.5943 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9828    2.6447   -1.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1006    2.1697   -0.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1942    2.3929    0.8458 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1368    1.4209   -0.9664 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2125    0.9539   -0.1798 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1854    0.1527   -1.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2925   -0.3770   -0.3345 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0697   -1.4031    0.6153 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4439   -1.9500    1.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2244   -0.9882    1.6250 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9596    0.3018    1.2309 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4561    0.4137   -0.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0875   -3.8461    0.2549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5031   -4.9756    0.1056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3986   -3.6244    0.6079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6336   -2.2552    0.6516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9662    1.6686    1.8179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9560    2.6638    0.7307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6450    3.0983    0.9526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6152    1.7074    0.9150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4568    1.0608   -0.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7823    0.3659    1.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2735   -3.2013   -0.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2470   -1.2138   -1.8378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7420   -1.3868   -0.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3549    1.2890   -1.6651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1121    0.9529    1.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5605   -0.5623    1.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9977    0.0692    0.3178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0978    2.9925   -1.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3613    3.0707    0.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1734    3.7486   -1.3576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0430    2.1976   -2.2019 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7919    0.2280    0.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6776    1.7561    0.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6702   -0.6577   -1.5746 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5664    0.8587   -1.7995 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5168   -2.2243    0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5776   -1.0922    1.5561 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9557   -2.2517    0.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3424   -2.8668    1.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9111    0.8844    1.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2047    0.7214    1.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2512   -0.0331   -0.8329 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3018    1.4743   -0.4094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9922   -1.9162    1.6610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4470   -1.9991   -0.0587 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
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
  7 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  1  0
 10  3  1  0
 27 22  1  0
 31  6  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  5 35  1  0
  5 36  1  0
  5 37  1  0
  9 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 14 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 23 53  1  0
 23 54  1  0
 24 55  1  0
 24 56  1  0
 26 57  1  0
 26 58  1  0
 27 59  1  0
 27 60  1  0
 31 61  1  0
 31 62  1  0
M  END

688
  Mrv0541 02231214562D          

 31 33  0  0  0  0            999 V2000
    1.6500   -0.5404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9150   -0.1279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.6971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5094   -0.9529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9383    1.5222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6898    1.3203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.5404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.2846    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6529   -0.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2239    0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6529    0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9383   -0.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2239   -0.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9383    0.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5094    0.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4335   -0.7918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949    0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4335    0.5360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    0.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9383   -1.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    1.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5094   -1.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  1 13  1  0  0  0  0
  2 22  1  0  0  0  0
  2 24  1  0  0  0  0
  3 18  1  0  0  0  0
  3 29  1  0  0  0  0
  4 19  1  0  0  0  0
  4 31  1  0  0  0  0
  5 20  1  0  0  0  0
  6 24  2  0  0  0  0
  7 29  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  0  0  0  0
 10 13  1  0  0  0  0
 11 18  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  2  0  0  0  0
 14 22  1  0  0  0  0
 15 19  2  0  0  0  0
 15 20  1  0  0  0  0
 15 21  1  0  0  0  0
 16 20  2  0  0  0  0
 16 24  1  0  0  0  0
 17 19  1  0  0  0  0
 17 27  1  0  0  0  0
 21 23  1  0  0  0  0
 23 26  2  0  0  0  0
 25 26  1  0  0  0  0
 25 28  1  0  0  0  0
 26 30  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014826

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(C\C=C(/C)CCC(=O)OCCN2CCOCC2)C(O)=C2C(=O)OCC2=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C23H31NO7/c1-15(5-7-19(25)30-13-10-24-8-11-29-12-9-24)4-6-17-21(26)20-18(14-31-23(20)27)16(2)22(17)28-3/h4,26H,5-14H2,1-3H3/b15-4+

> <INCHI_KEY>
RTGDFNSFWBGLEC-SYZQJQIISA-N

> <FORMULA>
C23H31NO7

> <MOLECULAR_WEIGHT>
433.4947

> <EXACT_MASS>
433.210052351

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
45.55005955684284

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.17

> <JCHEM_LOGP>
3.4736355743333323

> <ALOGPS_LOGS>
-3.66

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.674685074330249

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.75889164079593

> <JCHEM_PKA_STRONGEST_BASIC>
6.194606743423789

> <JCHEM_POLAR_SURFACE_AREA>
94.52999999999999

> <JCHEM_REFRACTIVITY>
117.0961

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.50e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
mycophenolate mofetil

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014826
     RDKit          3D
Mycophenolate mofetil
 62 64  0  0  0  0  0  0  0  0999 V2000
   -3.9512    2.2017    0.8314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3565    1.3993   -0.2356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6633    0.0604   -0.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9843   -0.2530    0.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9972    0.7904    0.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3597   -1.5757    0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4299   -2.5606    0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1180   -2.2469   -0.2846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2373   -3.2938   -0.5173 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7429   -0.9007   -0.3907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3353   -0.7135   -0.8013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8472    0.6287   -0.9702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8012    1.1278   -0.3248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0233    0.3417    0.6510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3846    2.5606   -0.5943 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9828    2.6447   -1.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1006    2.1697   -0.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1942    2.3929    0.8458 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1368    1.4209   -0.9664 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2125    0.9539   -0.1798 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1854    0.1527   -1.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2925   -0.3770   -0.3345 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0697   -1.4031    0.6153 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4439   -1.9500    1.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2244   -0.9882    1.6250 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9596    0.3018    1.2309 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4561    0.4137   -0.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0875   -3.8461    0.2549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5031   -4.9756    0.1056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3986   -3.6244    0.6079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6336   -2.2552    0.6516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9662    1.6686    1.8179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9560    2.6638    0.7307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6450    3.0983    0.9526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6152    1.7074    0.9150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4568    1.0608   -0.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7823    0.3659    1.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2735   -3.2013   -0.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2470   -1.2138   -1.8378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7420   -1.3868   -0.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3549    1.2890   -1.6651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1121    0.9529    1.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5605   -0.5623    1.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9977    0.0692    0.3178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0978    2.9925   -1.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3613    3.0707    0.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1734    3.7486   -1.3576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0430    2.1976   -2.2019 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7919    0.2280    0.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6776    1.7561    0.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6702   -0.6577   -1.5746 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5664    0.8587   -1.7995 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5168   -2.2243    0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5776   -1.0922    1.5561 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9557   -2.2517    0.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3424   -2.8668    1.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9111    0.8844    1.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2047    0.7214    1.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2512   -0.0331   -0.8329 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3018    1.4743   -0.4094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9922   -1.9162    1.6610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4470   -1.9991   -0.0587 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
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
  7 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  1  0
 10  3  1  0
 27 22  1  0
 31  6  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  5 35  1  0
  5 36  1  0
  5 37  1  0
  9 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 14 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 23 53  1  0
 23 54  1  0
 24 55  1  0
 24 56  1  0
 26 57  1  0
 26 58  1  0
 27 59  1  0
 27 60  1  0
 31 61  1  0
 31 62  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 688                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       3.080  -1.009   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      24.108  -0.239   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       9.748   1.301   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      17.751  -1.779   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      20.418   2.841   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      23.688   2.465   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      11.082  -1.009   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       5.748   0.531   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       5.748  -1.009   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414   1.301   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081   1.301   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414  -1.779   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.080   0.531   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      21.752  -1.009   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      19.085   0.531   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      21.752   0.531   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      20.418  -1.779   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.415   0.531   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      19.085  -1.009   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      20.418   1.301   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.751   1.301   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      23.209  -1.478   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.417   0.531   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      23.209   1.001   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.750   0.531   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      15.083   1.301   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      20.418  -3.319   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.416   1.301   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.082   0.531   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      15.083   2.841   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      17.751  -3.319   0.000  0.00  0.00           C+0
CONECT    1   12   13                                                       
CONECT    2   22   24                                                       
CONECT    3   18   29                                                       
CONECT    4   19   31                                                       
CONECT    5   20                                                            
CONECT    6   24                                                            
CONECT    7   29                                                            
CONECT    8    9   10   11                                                  
CONECT    9    8   12                                                       
CONECT   10    8   13                                                       
CONECT   11    8   18                                                       
CONECT   12    1    9                                                       
CONECT   13    1   10                                                       
CONECT   14   16   17   22                                                  
CONECT   15   19   20   21                                                  
CONECT   16   14   20   24                                                  
CONECT   17   14   19   27                                                  
CONECT   18    3   11                                                       
CONECT   19    4   15   17                                                  
CONECT   20    5   15   16                                                  
CONECT   21   15   23                                                       
CONECT   22    2   14                                                       
CONECT   23   21   26                                                       
CONECT   24    2    6   16                                                  
CONECT   25   26   28                                                       
CONECT   26   23   25   30                                                  
CONECT   27   17                                                            
CONECT   28   25   29                                                       
CONECT   29    3    7   28                                                  
CONECT   30   26                                                            
CONECT   31    4                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

COMPND    HMDB0014826
HETATM    1  C1  UNL     1      -3.951   2.202   0.831  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.356   1.399  -0.236  1.00  0.00           O  
HETATM    3  C2  UNL     1      -4.663   0.060  -0.148  1.00  0.00           C  
HETATM    4  C3  UNL     1      -5.984  -0.253   0.206  1.00  0.00           C  
HETATM    5  C4  UNL     1      -6.997   0.790   0.472  1.00  0.00           C  
HETATM    6  C5  UNL     1      -6.360  -1.576   0.313  1.00  0.00           C  
HETATM    7  C6  UNL     1      -5.430  -2.561   0.069  1.00  0.00           C  
HETATM    8  C7  UNL     1      -4.118  -2.247  -0.285  1.00  0.00           C  
HETATM    9  O2  UNL     1      -3.237  -3.294  -0.517  1.00  0.00           O  
HETATM   10  C8  UNL     1      -3.743  -0.901  -0.391  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.335  -0.714  -0.801  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.847   0.629  -0.970  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.801   1.128  -0.325  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.023   0.342   0.651  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.385   2.561  -0.594  1.00  0.00           C  
HETATM   16  C14 UNL     1       0.983   2.645  -1.176  1.00  0.00           C  
HETATM   17  C15 UNL     1       2.101   2.170  -0.377  1.00  0.00           C  
HETATM   18  O3  UNL     1       2.194   2.393   0.846  1.00  0.00           O  
HETATM   19  O4  UNL     1       3.137   1.421  -0.966  1.00  0.00           O  
HETATM   20  C16 UNL     1       4.213   0.954  -0.180  1.00  0.00           C  
HETATM   21  C17 UNL     1       5.185   0.153  -1.023  1.00  0.00           C  
HETATM   22  N1  UNL     1       6.293  -0.377  -0.334  1.00  0.00           N  
HETATM   23  C18 UNL     1       6.070  -1.403   0.615  1.00  0.00           C  
HETATM   24  C19 UNL     1       7.444  -1.950   1.017  1.00  0.00           C  
HETATM   25  O5  UNL     1       8.224  -0.988   1.625  1.00  0.00           O  
HETATM   26  C20 UNL     1       7.960   0.302   1.231  1.00  0.00           C  
HETATM   27  C21 UNL     1       7.456   0.414  -0.195  1.00  0.00           C  
HETATM   28  C22 UNL     1      -6.088  -3.846   0.255  1.00  0.00           C  
HETATM   29  O6  UNL     1      -5.503  -4.976   0.106  1.00  0.00           O  
HETATM   30  O7  UNL     1      -7.399  -3.624   0.608  1.00  0.00           O  
HETATM   31  C23 UNL     1      -7.634  -2.255   0.652  1.00  0.00           C  
HETATM   32  H1  UNL     1      -3.966   1.669   1.818  1.00  0.00           H  
HETATM   33  H2  UNL     1      -2.956   2.664   0.731  1.00  0.00           H  
HETATM   34  H3  UNL     1      -4.645   3.098   0.953  1.00  0.00           H  
HETATM   35  H4  UNL     1      -6.615   1.707   0.915  1.00  0.00           H  
HETATM   36  H5  UNL     1      -7.457   1.061  -0.520  1.00  0.00           H  
HETATM   37  H6  UNL     1      -7.782   0.366   1.157  1.00  0.00           H  
HETATM   38  H7  UNL     1      -2.274  -3.201  -0.784  1.00  0.00           H  
HETATM   39  H8  UNL     1      -2.247  -1.214  -1.838  1.00  0.00           H  
HETATM   40  H9  UNL     1      -1.742  -1.387  -0.138  1.00  0.00           H  
HETATM   41  H10 UNL     1      -2.355   1.289  -1.665  1.00  0.00           H  
HETATM   42  H11 UNL     1       0.112   0.953   1.588  1.00  0.00           H  
HETATM   43  H12 UNL     1      -0.560  -0.562   1.044  1.00  0.00           H  
HETATM   44  H13 UNL     1       0.998   0.069   0.318  1.00  0.00           H  
HETATM   45  H14 UNL     1      -1.098   2.992  -1.294  1.00  0.00           H  
HETATM   46  H15 UNL     1      -0.361   3.071   0.394  1.00  0.00           H  
HETATM   47  H16 UNL     1       1.173   3.749  -1.358  1.00  0.00           H  
HETATM   48  H17 UNL     1       1.043   2.198  -2.202  1.00  0.00           H  
HETATM   49  H18 UNL     1       3.792   0.228   0.566  1.00  0.00           H  
HETATM   50  H19 UNL     1       4.678   1.756   0.389  1.00  0.00           H  
HETATM   51  H20 UNL     1       4.670  -0.658  -1.575  1.00  0.00           H  
HETATM   52  H21 UNL     1       5.566   0.859  -1.799  1.00  0.00           H  
HETATM   53  H22 UNL     1       5.517  -2.224   0.128  1.00  0.00           H  
HETATM   54  H23 UNL     1       5.578  -1.092   1.556  1.00  0.00           H  
HETATM   55  H24 UNL     1       7.956  -2.252   0.059  1.00  0.00           H  
HETATM   56  H25 UNL     1       7.342  -2.867   1.618  1.00  0.00           H  
HETATM   57  H26 UNL     1       8.911   0.884   1.283  1.00  0.00           H  
HETATM   58  H27 UNL     1       7.205   0.721   1.915  1.00  0.00           H  
HETATM   59  H28 UNL     1       8.251  -0.033  -0.833  1.00  0.00           H  
HETATM   60  H29 UNL     1       7.302   1.474  -0.409  1.00  0.00           H  
HETATM   61  H30 UNL     1      -7.992  -1.916   1.661  1.00  0.00           H  
HETATM   62  H31 UNL     1      -8.447  -1.999  -0.059  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3
CONECT    3    4    4   10
CONECT    4    5    6
CONECT    5   35   36   37
CONECT    6    7    7   31
CONECT    7    8   28
CONECT    8    9   10   10
CONECT    9   38
CONECT   10   11
CONECT   11   12   39   40
CONECT   12   13   13   41
CONECT   13   14   15
CONECT   14   42   43   44
CONECT   15   16   45   46
CONECT   16   17   47   48
CONECT   17   18   18   19
CONECT   19   20
CONECT   20   21   49   50
CONECT   21   22   51   52
CONECT   22   23   27
CONECT   23   24   53   54
CONECT   24   25   55   56
CONECT   25   26
CONECT   26   27   57   58
CONECT   27   59   60
CONECT   28   29   29   30
CONECT   30   31
CONECT   31   61   62
END

HMDB0014826
     RDKit          3D
Mycophenolate mofetil
 62 64  0  0  0  0  0  0  0  0999 V2000
   -3.9512    2.2017    0.8314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3565    1.3993   -0.2356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6633    0.0604   -0.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9843   -0.2530    0.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9972    0.7904    0.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3597   -1.5757    0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4299   -2.5606    0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1180   -2.2469   -0.2846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2373   -3.2938   -0.5173 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7429   -0.9007   -0.3907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3353   -0.7135   -0.8013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8472    0.6287   -0.9702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8012    1.1278   -0.3248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0233    0.3417    0.6510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3846    2.5606   -0.5943 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9828    2.6447   -1.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1006    2.1697   -0.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1942    2.3929    0.8458 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1368    1.4209   -0.9664 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2125    0.9539   -0.1798 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1854    0.1527   -1.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2925   -0.3770   -0.3345 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0697   -1.4031    0.6153 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4439   -1.9500    1.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2244   -0.9882    1.6250 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9596    0.3018    1.2309 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4561    0.4137   -0.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0875   -3.8461    0.2549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5031   -4.9756    0.1056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3986   -3.6244    0.6079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6336   -2.2552    0.6516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9662    1.6686    1.8179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9560    2.6638    0.7307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6450    3.0983    0.9526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6152    1.7074    0.9150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4568    1.0608   -0.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7823    0.3659    1.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2735   -3.2013   -0.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2470   -1.2138   -1.8378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7420   -1.3868   -0.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3549    1.2890   -1.6651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1121    0.9529    1.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5605   -0.5623    1.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9977    0.0692    0.3178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0978    2.9925   -1.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3613    3.0707    0.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1734    3.7486   -1.3576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0430    2.1976   -2.2019 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7919    0.2280    0.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6776    1.7561    0.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6702   -0.6577   -1.5746 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5664    0.8587   -1.7995 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5168   -2.2243    0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5776   -1.0922    1.5561 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9557   -2.2517    0.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3424   -2.8668    1.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9111    0.8844    1.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2047    0.7214    1.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2512   -0.0331   -0.8329 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3018    1.4743   -0.4094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9922   -1.9162    1.6610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4470   -1.9991   -0.0587 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
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
  7 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  1  0
 10  3  1  0
 27 22  1  0
 31  6  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  5 35  1  0
  5 36  1  0
  5 37  1  0
  9 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 14 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 23 53  1  0
 23 54  1  0
 24 55  1  0
 24 56  1  0
 26 57  1  0
 26 58  1  0
 27 59  1  0
 27 60  1  0
 31 61  1  0
 31 62  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Morpholinoethyl (e)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoate	ChEBI
Cellcept	ChEBI
MMF	ChEBI
Mycophenolic acid morpholinoethyl ester	ChEBI
RS 61443	ChEBI
2-Morpholinoethyl (e)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoic acid	Generator
Mycophenolate morpholinoethyl ester	Generator
Mycophenolic acid mofetil	Generator
Mycophenylate mofetil	HMDB
Mycophenolate sodium	HMDB
Myfortic	HMDB
Sodium mycophenolate	HMDB
Mycophenolate mofetil hydrochloride	HMDB
Mofetil hydrochloride, mycophenolate	HMDB
Mofetil, mycophenolate	HMDB
Mycophenolate, sodium	HMDB
Mycophenolic acid	HMDB

Chemical Formula

C₂₃H₃₁NO₇

Average Molecular Weight

433.4947

Monoisotopic Molecular Weight

433.210052351

IUPAC Name

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

Traditional Name

mycophenolate mofetil

CAS Registry Number

128794-94-5

SMILES

COC1=C(C\C=C(/C)CCC(=O)OCCN2CCOCC2)C(O)=C2C(=O)OCC2=C1C

InChI Identifier

InChI=1S/C23H31NO7/c1-15(5-7-19(25)30-13-10-24-8-11-29-12-9-24)4-6-17-21(26)20-18(14-31-23(20)27)16(2)22(17)28-3/h4,26H,5-14H2,1-3H3/b15-4+

InChI Key

RTGDFNSFWBGLEC-SYZQJQIISA-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
Alkyl aryl ether
Fatty acid ester
Dicarboxylic acid or derivatives
Morpholine
Oxazinane
Fatty acyl
Benzenoid
Vinylogous acid
Amino acid or derivatives
Carboxylic acid ester
Lactone
Tertiary amine
Tertiary aliphatic amine
Ether
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Azacycle
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Amine
Carbonyl group
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary amino compound (CHEBI:8764 )
carboxylic ester (CHEBI:8764 )
phenols (CHEBI:8764 )
ether (CHEBI:8764 )
gamma-lactone (CHEBI:8764 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014826)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Mycophenolic Acid Metabolism Pathway (PathBank: SMP0000652)

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	0.095 g/L	Not Available
LogP	2.5	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	197.319	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000923

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.095 g/L	ALOGPS
logP	2.17	ALOGPS
logP	3.47	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	9.76	ChemAxon
pKa (Strongest Basic)	6.19	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	94.53 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	117.1 m³·mol⁻¹	ChemAxon
Polarizability	45.55 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	203.342	31661259
DarkChem	[M-H]-	197.423	31661259
DeepCCS	[M+H]+	198.57	30932474
DeepCCS	[M-H]-	196.036	30932474
DeepCCS	[M-2H]-	230.97	30932474
DeepCCS	[M+Na]+	207.135	30932474
AllCCS	[M+H]+	203.4	32859911
AllCCS	[M+H-H2O]+	201.0	32859911
AllCCS	[M+NH4]+	205.6	32859911
AllCCS	[M+Na]+	206.3	32859911
AllCCS	[M-H]-	205.4	32859911
AllCCS	[M+Na-2H]-	206.5	32859911
AllCCS	[M+HCOO]-	208.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Mycophenolate mofetil	COC1=C(C\C=C(/C)CCC(=O)OCCN2CCOCC2)C(O)=C2C(=O)OCC2=C1C	3905.1	Standard polar	33892256
Mycophenolate mofetil	COC1=C(C\C=C(/C)CCC(=O)OCCN2CCOCC2)C(O)=C2C(=O)OCC2=C1C	3180.0	Standard non polar	33892256
Mycophenolate mofetil	COC1=C(C\C=C(/C)CCC(=O)OCCN2CCOCC2)C(O)=C2C(=O)OCC2=C1C	3452.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Mycophenolate mofetil,1TMS,isomer #1	COC1=C(C)C2=C(C(=O)OC2)C(O[Si](C)(C)C)=C1C/C=C(\C)CCC(=O)OCCN1CCOCC1	3321.6	Semi standard non polar	33892256
Mycophenolate mofetil,1TBDMS,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)OCCN1CCOCC1	3527.0	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 - Mycophenolate mofetil GC-MS (Non-derivatized) - 70eV, Positive	splash10-0w4i-2393200000-d549469b4d276b82f0a4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mycophenolate mofetil GC-MS (1 TMS) - 70eV, Positive	splash10-0itd-4629600000-670072fd9bb0a49d7de1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mycophenolate mofetil 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 - Mycophenolate mofetil , positive-QTOF	splash10-0019-1741900000-022d7009668cda105e50	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mycophenolate mofetil 10V, Positive-QTOF	splash10-01q9-0743900000-133a311844263f919bdd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mycophenolate mofetil 20V, Positive-QTOF	splash10-03di-1961100000-5da439d2a9f8cae8f445	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mycophenolate mofetil 40V, Positive-QTOF	splash10-03xr-9740100000-6af6a8b42b2977762a4c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mycophenolate mofetil 10V, Negative-QTOF	splash10-0f89-0419700000-cbea334d70b0f1f93d90	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mycophenolate mofetil 20V, Negative-QTOF	splash10-0ue9-2859500000-742b323b12fbfbe7a502	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mycophenolate mofetil 40V, Negative-QTOF	splash10-0fe3-9564000000-dd2d4e0510f30a121c4e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mycophenolate mofetil 10V, Positive-QTOF	splash10-001i-0020900000-038b179f46cd4955dd10	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mycophenolate mofetil 20V, Positive-QTOF	splash10-0a4i-0291200000-8369d80f2ca22af88fba	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mycophenolate mofetil 40V, Positive-QTOF	splash10-03di-0960100000-828ad4ec3f0767246892	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mycophenolate mofetil 10V, Negative-QTOF	splash10-001i-0501900000-6ec023ec52bc4a8e5ea1	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mycophenolate mofetil 20V, Negative-QTOF	splash10-004l-2921100000-7173e63d30a5885f9a87	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mycophenolate mofetil 40V, Negative-QTOF	splash10-00or-1590000000-77b54540de37ccf344ec	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

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 DB00688	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00688	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00688

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4444535

KEGG Compound ID

C07908

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Mycophenolate_mofetil

METLIN ID

Not Available

PubChem Compound

5281078

PDB ID

Not Available

ChEBI ID

8764

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)

Not Available

General References

Picard N, Cresteil T, Premaud A, Marquet P: Characterization of a phase 1 metabolite of mycophenolic acid produced by CYP3A4/5. Ther Drug Monit. 2004 Dec;26(6):600-8. [PubMed:15570183 ]
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 ]
(). FDA label . .

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

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

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

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 1-8

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:: UGT1A8
Uniprot ID:: Q9HAW9
Molecular weight:: 59741.035

References

Thervet E, Anglicheau D, Legendre C: [Pharmacology of mycophenolate mofetil: recent data and clinical consequences]. Nephrologie. 2001;22(7):331-7. [PubMed:11817210 ]

Enzyme Details

5. UDP-glucuronosyltransferase 1-10

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:: UGT1A10
Uniprot ID:: Q9HAW8
Molecular weight:: 59809.075

References

Thervet E, Anglicheau D, Legendre C: [Pharmacology of mycophenolate mofetil: recent data and clinical consequences]. Nephrologie. 2001;22(7):331-7. [PubMed:11817210 ]

Enzyme Details

6. 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

7. 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

8. 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 ]
Bremer S, Rootwelt H, Bergan S: Real-time PCR determination of IMPDH1 and IMPDH2 expression in blood cells. Clin Chem. 2007 Jun;53(6):1023-9. Epub 2007 Apr 26. [PubMed:17463174 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

9. 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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Bremer S, Rootwelt H, Bergan S: Real-time PCR determination of IMPDH1 and IMPDH2 expression in blood cells. Clin Chem. 2007 Jun;53(6):1023-9. Epub 2007 Apr 26. [PubMed:17463174 ]
Wang J, Yang JW, Zeevi A, Webber SA, Girnita DM, Selby R, Fu J, Shah T, Pravica V, Hutchinson IV, Burckart GJ: IMPDH1 gene polymorphisms and association with acute rejection in renal transplant patients. Clin Pharmacol Ther. 2008 May;83(5):711-7. Epub 2007 Sep 12. [PubMed:17851563 ]
Sanquer S, Maison P, Tomkiewicz C, Macquin-Mavier I, Legendre C, Barouki R, Lang P: Expression of inosine monophosphate dehydrogenase type I and type II after mycophenolate mofetil treatment: a 2-year follow-up in kidney transplantation. Clin Pharmacol Ther. 2008 Feb;83(2):328-35. Epub 2007 Aug 22. [PubMed:17713475 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Mycophenolate mofetil (HMDB0014826)

MOL for HMDB0014826 (Mycophenolate mofetil)

3D MOL for HMDB0014826 (Mycophenolate mofetil)

3D SDF for HMDB0014826 (Mycophenolate mofetil)

3D-SDF for HMDB0014826 (Mycophenolate mofetil)

PDB for HMDB0014826 (Mycophenolate mofetil)

3D PDB for HMDB0014826 (Mycophenolate mofetil)

SMILES for HMDB0014826 (Mycophenolate mofetil)

INCHI for HMDB0014826 (Mycophenolate mofetil)

Structure for HMDB0014826 (Mycophenolate mofetil)

3D Structure for HMDB0014826 (Mycophenolate mofetil)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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