Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 01:24:38 UTC

Update Date

2021-09-14 15:42:59 UTC

HMDB ID

HMDB0060491

Secondary Accession Numbers

HMDB60491

Metabolite Identification

Common Name

Mycophenolic acid O-acyl-glucuronide

Description

Mycophenolic acid O-acyl-glucuronide, also known as acmpag, belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond. Mycophenolic acid O-acyl-glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, mycophenolic acid O-acyl-glucuronide participates in a number of enzymatic reactions. In particular, mycophenolic acid O-acyl-glucuronide and uridine 5'-diphosphate can be biosynthesized from mycophenolic acid and uridine diphosphate glucuronic acid; which is catalyzed by the enzyme UDP-glucuronosyltransferase 2B7. In addition, mycophenolic acid O-acyl-glucuronide and uridine 5'-diphosphate can be biosynthesized from mycophenolic acid and uridine diphosphate glucuronic acid; which is mediated by the enzyme UDP-glucuronosyltransferase 2B7. Mycophenolic acid O-acyl-glucuronide is a metabolite of mycophenolate mofetil. In humans, mycophenolic acid O-acyl-glucuronide is involved in mycophenolic acid metabolism pathway. Other cells are able to recover purines via a separate, scavenger, pathway and are, thus, able to escape the effect. It is a reversible inhibitor of inosine monophosphate dehydrogenase (IMPDH) in purine biosynthesis which is necessary for the growth of T cells and B cells. MMF is a less toxic alternative to azathioprine. Mycophenolate mofetil (MMF) (brand names CellCept, Myfortic) is an immunosuppressant and prodrug of mycophenolic acid, used extensively in transplant medicine.

Structure

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


  Mrv0541 05161318242D          

 35 37  0  0  0  0            999 V2000
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5004    6.0299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5004    4.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7553    3.9104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9853    5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  9  1  1  0  0  0  0
  9  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  2  1  0  0  0  0
 11  6  1  0  0  0  0
 12  8  1  0  0  0  0
 12 10  1  0  0  0  0
 13  7  1  0  0  0  0
 14 12  2  0  0  0  0
 15 11  2  0  0  0  0
 15 14  1  0  0  0  0
 17 16  1  0  0  0  0
 18 16  1  0  0  0  0
 19 10  2  0  0  0  0
 19 11  1  0  0  0  0
 20 17  1  0  0  0  0
 20 21  1  6  0  0  0
 22 14  1  0  0  0  0
 23 18  1  0  0  0  0
 24 13  2  0  0  0  0
 25 15  1  0  0  0  0
 16 26  1  6  0  0  0
 17 27  1  1  0  0  0
 18 28  1  1  0  0  0
 29 21  2  0  0  0  0
 30 21  1  0  0  0  0
 31 22  2  0  0  0  0
 32  3  1  0  0  0  0
 32 19  1  0  0  0  0
 33  8  1  0  0  0  0
 33 22  1  0  0  0  0
 34 13  1  0  0  0  0
 23 34  1  6  0  0  0
 35 20  1  0  0  0  0
 35 23  1  0  0  0  0
M  END

HMDB0060491
     RDKit          3D
Mycophenolic acid O-acyl-glucuronide
 63 65  0  0  0  0  0  0  0  0999 V2000
   -2.1437    0.9755    1.6855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7561    1.5209    0.5011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9516    0.8589    0.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1495    1.2966    0.7410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1935    2.4052    1.6828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3155    0.6333    0.3912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2618   -0.4100   -0.4992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0545   -0.8466   -1.0876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0660   -1.8880   -1.9620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8957   -0.1824   -0.7391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6393   -0.6211   -1.3687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7819   -1.4969   -0.5755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4801   -1.3161   -0.3844 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1638   -0.1493   -1.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2630   -2.3134    0.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9373   -1.7830    1.6445 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9336   -0.7539    1.3645 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7124    0.4678    1.5713 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1728   -1.1049    0.8527 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2079   -0.1769    0.5559 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4684   -0.1760   -0.8352 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1710    1.0005   -1.1169 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4792    1.1005   -2.5663 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1037    2.0722   -3.0489 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0608    0.0898   -3.4096 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4513    1.0743   -0.3166 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5146    2.2378    0.4618 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6678   -0.1422    0.5271 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2266   -1.1966   -0.2226 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4608   -0.6584    1.2353 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4127   -0.2624    2.5718 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6041   -0.9307   -0.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9185   -1.8987   -1.4401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4261   -0.1637    0.1231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7086    0.8354    0.8081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5442    1.5144    2.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3770   -0.0966    1.8208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0634    1.1200    1.6431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3457    2.0860    2.7308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2168    2.9513    1.6603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9489    3.1545    1.3472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2981   -2.2470   -2.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8076   -1.0466   -2.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0613    0.3478   -1.6207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2395   -2.3833   -0.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1628   -0.0975   -2.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0975    0.7696   -0.4691 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2733   -0.2436   -1.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9925   -2.8883   -0.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4323   -3.1153    0.7769 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4942   -2.6286    2.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1565   -1.4611    2.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9021    0.8446    0.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5315    1.8438   -0.7922 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1123    0.1157   -3.8141 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3094    1.1356   -1.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3878    2.3635    0.8695 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4030    0.1480    1.3319 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9988   -1.1061   -1.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4133   -1.7917    1.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4814    0.0160    2.8340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0828    1.8382    0.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8396    0.7590    1.9094 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  2  0
 23 25  1  0
 22 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
  7 32  1  0
 32 33  2  0
 32 34  1  0
 34 35  1  0
 10  3  1  0
 30 20  1  0
 35  6  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  5 39  1  0
  5 40  1  0
  5 41  1  0
  9 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 14 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  0
 15 50  1  0
 16 51  1  0
 16 52  1  0
 20 53  1  1
 22 54  1  1
 25 55  1  0
 26 56  1  6
 27 57  1  0
 28 58  1  1
 29 59  1  0
 30 60  1  1
 31 61  1  0
 35 62  1  0
 35 63  1  0
M  END


  Mrv0541 05161318242D          

 35 37  0  0  0  0            999 V2000
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5004    6.0299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5004    4.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7553    3.9104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9853    5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  9  1  1  0  0  0  0
  9  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  2  1  0  0  0  0
 11  6  1  0  0  0  0
 12  8  1  0  0  0  0
 12 10  1  0  0  0  0
 13  7  1  0  0  0  0
 14 12  2  0  0  0  0
 15 11  2  0  0  0  0
 15 14  1  0  0  0  0
 17 16  1  0  0  0  0
 18 16  1  0  0  0  0
 19 10  2  0  0  0  0
 19 11  1  0  0  0  0
 20 17  1  0  0  0  0
 20 21  1  6  0  0  0
 22 14  1  0  0  0  0
 23 18  1  0  0  0  0
 24 13  2  0  0  0  0
 25 15  1  0  0  0  0
 16 26  1  6  0  0  0
 17 27  1  1  0  0  0
 18 28  1  1  0  0  0
 29 21  2  0  0  0  0
 30 21  1  0  0  0  0
 31 22  2  0  0  0  0
 32  3  1  0  0  0  0
 32 19  1  0  0  0  0
 33  8  1  0  0  0  0
 33 22  1  0  0  0  0
 34 13  1  0  0  0  0
 23 34  1  6  0  0  0
 35 20  1  0  0  0  0
 35 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060491

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C\C=C(/C)CCC(=O)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H28O12/c1-9(4-6-11-15(25)14-12(8-33-22(14)31)10(2)19(11)32-3)5-7-13(24)34-23-18(28)16(26)17(27)20(35-23)21(29)30/h4,16-18,20,23,25-28H,5-8H2,1-3H3,(H,29,30)/b9-4+/t16-,17-,18+,20-,23+/m0/s1

> <INCHI_KEY>
QBMSTEZXAMABFF-UEARNRKISA-N

> <FORMULA>
C23H28O12

> <MOLECULAR_WEIGHT>
496.4612

> <EXACT_MASS>
496.15807636

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
49.23745704607755

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoyl]oxy}oxane-2-carboxylic acid

> <ALOGPS_LOGP>
0.91

> <JCHEM_LOGP>
1.5798038923333328

> <ALOGPS_LOGS>
-2.84

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.757248896557277

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.261496203828545

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6868985921238897

> <JCHEM_POLAR_SURFACE_AREA>
189.27999999999994

> <JCHEM_REFRACTIVITY>
117.53199999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.23e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methylhex-4-enoyl]oxy}oxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060491
     RDKit          3D
Mycophenolic acid O-acyl-glucuronide
 63 65  0  0  0  0  0  0  0  0999 V2000
   -2.1437    0.9755    1.6855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7561    1.5209    0.5011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9516    0.8589    0.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1495    1.2966    0.7410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1935    2.4052    1.6828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3155    0.6333    0.3912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2618   -0.4100   -0.4992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0545   -0.8466   -1.0876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0660   -1.8880   -1.9620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8957   -0.1824   -0.7391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6393   -0.6211   -1.3687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7819   -1.4969   -0.5755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4801   -1.3161   -0.3844 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1638   -0.1493   -1.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2630   -2.3134    0.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9373   -1.7830    1.6445 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9336   -0.7539    1.3645 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7124    0.4678    1.5713 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1728   -1.1049    0.8527 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2079   -0.1769    0.5559 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4684   -0.1760   -0.8352 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1710    1.0005   -1.1169 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4792    1.1005   -2.5663 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1037    2.0722   -3.0489 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0608    0.0898   -3.4096 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4513    1.0743   -0.3166 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5146    2.2378    0.4618 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6678   -0.1422    0.5271 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2266   -1.1966   -0.2226 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4608   -0.6584    1.2353 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4127   -0.2624    2.5718 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6041   -0.9307   -0.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9185   -1.8987   -1.4401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4261   -0.1637    0.1231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7086    0.8354    0.8081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5442    1.5144    2.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3770   -0.0966    1.8208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0634    1.1200    1.6431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3457    2.0860    2.7308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2168    2.9513    1.6603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9489    3.1545    1.3472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2981   -2.2470   -2.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8076   -1.0466   -2.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0613    0.3478   -1.6207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2395   -2.3833   -0.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1628   -0.0975   -2.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0975    0.7696   -0.4691 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2733   -0.2436   -1.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9925   -2.8883   -0.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4323   -3.1153    0.7769 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4942   -2.6286    2.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1565   -1.4611    2.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9021    0.8446    0.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5315    1.8438   -0.7922 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1123    0.1157   -3.8141 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3094    1.1356   -1.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3878    2.3635    0.8695 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4030    0.1480    1.3319 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9988   -1.1061   -1.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4133   -1.7917    1.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4814    0.0160    2.8340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0828    1.8382    0.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8396    0.7590    1.9094 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  2  0
 23 25  1  0
 22 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
  7 32  1  0
 32 33  2  0
 32 34  1  0
 34 35  1  0
 10  3  1  0
 30 20  1  0
 35  6  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  5 39  1  0
  5 40  1  0
  5 41  1  0
  9 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 14 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  0
 15 50  1  0
 16 51  1  0
 16 52  1  0
 20 53  1  1
 22 54  1  1
 25 55  1  0
 26 56  1  6
 27 57  1  0
 28 58  1  1
 29 59  1  0
 30 60  1  1
 31 61  1  0
 35 62  1  0
 35 63  1  0
M  END

HEADER    PROTEIN                                 16-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-MAY-13         0                                  
HETATM    1  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.336  13.090   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.335  10.780   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.668   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -12.134  11.256   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -9.336  11.550   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.002   9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -10.669  10.780   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -10.669   9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -9.336   8.470   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  10.780   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -8.002  10.780   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  11.550   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  13.090   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -12.134   8.764   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.000  10.780   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -9.336   6.930   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       6.668   8.470   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       6.668  11.550   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       4.001   6.930   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       2.667  13.860   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       5.335  13.860   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0     -12.610   7.299   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -6.668  11.550   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0     -13.039  10.010   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       1.334   8.470   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       2.667  10.780   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   32                                                            
CONECT    4    6    9                                                       
CONECT    5    7    9                                                       
CONECT    6    4   11                                                       
CONECT    7    5   13                                                       
CONECT    8   12   33                                                       
CONECT    9    1    4    5                                                  
CONECT   10    2   12   19                                                  
CONECT   11    6   15   19                                                  
CONECT   12    8   10   14                                                  
CONECT   13    7   24   34                                                  
CONECT   14   12   15   22                                                  
CONECT   15   11   14   25                                                  
CONECT   16   17   18   26                                                  
CONECT   17   16   20   27                                                  
CONECT   18   16   23   28                                                  
CONECT   19   10   11   32                                                  
CONECT   20   17   21   35                                                  
CONECT   21   20   29   30                                                  
CONECT   22   14   31   33                                                  
CONECT   23   18   34   35                                                  
CONECT   24   13                                                            
CONECT   25   15                                                            
CONECT   26   16                                                            
CONECT   27   17                                                            
CONECT   28   18                                                            
CONECT   29   21                                                            
CONECT   30   21                                                            
CONECT   31   22                                                            
CONECT   32    3   19                                                       
CONECT   33    8   22                                                       
CONECT   34   13   23                                                       
CONECT   35   20   23                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

COMPND    HMDB0060491
HETATM    1  C1  UNL     1      -2.144   0.975   1.685  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.756   1.521   0.501  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.952   0.859   0.154  1.00  0.00           C  
HETATM    4  C3  UNL     1      -5.150   1.297   0.741  1.00  0.00           C  
HETATM    5  C4  UNL     1      -5.193   2.405   1.683  1.00  0.00           C  
HETATM    6  C5  UNL     1      -6.315   0.633   0.391  1.00  0.00           C  
HETATM    7  C6  UNL     1      -6.262  -0.410  -0.499  1.00  0.00           C  
HETATM    8  C7  UNL     1      -5.054  -0.847  -1.088  1.00  0.00           C  
HETATM    9  O2  UNL     1      -5.066  -1.888  -1.962  1.00  0.00           O  
HETATM   10  C8  UNL     1      -3.896  -0.182  -0.739  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.639  -0.621  -1.369  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.782  -1.497  -0.575  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.480  -1.316  -0.384  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.164  -0.149  -1.015  1.00  0.00           C  
HETATM   15  C13 UNL     1       0.263  -2.313   0.420  1.00  0.00           C  
HETATM   16  C14 UNL     1       0.937  -1.783   1.645  1.00  0.00           C  
HETATM   17  C15 UNL     1       1.934  -0.754   1.364  1.00  0.00           C  
HETATM   18  O3  UNL     1       1.712   0.468   1.571  1.00  0.00           O  
HETATM   19  O4  UNL     1       3.173  -1.105   0.853  1.00  0.00           O  
HETATM   20  C16 UNL     1       4.208  -0.177   0.556  1.00  0.00           C  
HETATM   21  O5  UNL     1       4.468  -0.176  -0.835  1.00  0.00           O  
HETATM   22  C17 UNL     1       5.171   1.001  -1.117  1.00  0.00           C  
HETATM   23  C18 UNL     1       5.479   1.100  -2.566  1.00  0.00           C  
HETATM   24  O6  UNL     1       6.104   2.072  -3.049  1.00  0.00           O  
HETATM   25  O7  UNL     1       5.061   0.090  -3.410  1.00  0.00           O  
HETATM   26  C19 UNL     1       6.451   1.074  -0.317  1.00  0.00           C  
HETATM   27  O8  UNL     1       6.515   2.238   0.462  1.00  0.00           O  
HETATM   28  C20 UNL     1       6.668  -0.142   0.527  1.00  0.00           C  
HETATM   29  O9  UNL     1       7.227  -1.197  -0.223  1.00  0.00           O  
HETATM   30  C21 UNL     1       5.461  -0.658   1.235  1.00  0.00           C  
HETATM   31  O10 UNL     1       5.413  -0.262   2.572  1.00  0.00           O  
HETATM   32  C22 UNL     1      -7.604  -0.931  -0.682  1.00  0.00           C  
HETATM   33  O11 UNL     1      -7.918  -1.899  -1.440  1.00  0.00           O  
HETATM   34  O12 UNL     1      -8.426  -0.164   0.123  1.00  0.00           O  
HETATM   35  C23 UNL     1      -7.709   0.835   0.808  1.00  0.00           C  
HETATM   36  H1  UNL     1      -2.544   1.514   2.588  1.00  0.00           H  
HETATM   37  H2  UNL     1      -2.377  -0.097   1.821  1.00  0.00           H  
HETATM   38  H3  UNL     1      -1.063   1.120   1.643  1.00  0.00           H  
HETATM   39  H4  UNL     1      -5.346   2.086   2.731  1.00  0.00           H  
HETATM   40  H5  UNL     1      -4.217   2.951   1.660  1.00  0.00           H  
HETATM   41  H6  UNL     1      -5.949   3.155   1.347  1.00  0.00           H  
HETATM   42  H7  UNL     1      -4.298  -2.247  -2.447  1.00  0.00           H  
HETATM   43  H8  UNL     1      -2.808  -1.047  -2.371  1.00  0.00           H  
HETATM   44  H9  UNL     1      -2.061   0.348  -1.621  1.00  0.00           H  
HETATM   45  H10 UNL     1      -2.239  -2.383  -0.090  1.00  0.00           H  
HETATM   46  H11 UNL     1      -0.163  -0.098  -2.097  1.00  0.00           H  
HETATM   47  H12 UNL     1      -0.098   0.770  -0.469  1.00  0.00           H  
HETATM   48  H13 UNL     1       1.273  -0.244  -1.061  1.00  0.00           H  
HETATM   49  H14 UNL     1       0.992  -2.888  -0.231  1.00  0.00           H  
HETATM   50  H15 UNL     1      -0.432  -3.115   0.777  1.00  0.00           H  
HETATM   51  H16 UNL     1       1.494  -2.629   2.147  1.00  0.00           H  
HETATM   52  H17 UNL     1       0.156  -1.461   2.370  1.00  0.00           H  
HETATM   53  H18 UNL     1       3.902   0.845   0.836  1.00  0.00           H  
HETATM   54  H19 UNL     1       4.531   1.844  -0.792  1.00  0.00           H  
HETATM   55  H20 UNL     1       4.112   0.116  -3.814  1.00  0.00           H  
HETATM   56  H21 UNL     1       7.309   1.136  -1.015  1.00  0.00           H  
HETATM   57  H22 UNL     1       7.388   2.363   0.869  1.00  0.00           H  
HETATM   58  H23 UNL     1       7.403   0.148   1.332  1.00  0.00           H  
HETATM   59  H24 UNL     1       6.999  -1.106  -1.173  1.00  0.00           H  
HETATM   60  H25 UNL     1       5.413  -1.792   1.184  1.00  0.00           H  
HETATM   61  H26 UNL     1       4.481   0.016   2.834  1.00  0.00           H  
HETATM   62  H27 UNL     1      -8.083   1.838   0.461  1.00  0.00           H  
HETATM   63  H28 UNL     1      -7.840   0.759   1.909  1.00  0.00           H  
CONECT    1    2   36   37   38
CONECT    2    3
CONECT    3    4    4   10
CONECT    4    5    6
CONECT    5   39   40   41
CONECT    6    7    7   35
CONECT    7    8   32
CONECT    8    9   10   10
CONECT    9   42
CONECT   10   11
CONECT   11   12   43   44
CONECT   12   13   13   45
CONECT   13   14   15
CONECT   14   46   47   48
CONECT   15   16   49   50
CONECT   16   17   51   52
CONECT   17   18   18   19
CONECT   19   20
CONECT   20   21   30   53
CONECT   21   22
CONECT   22   23   26   54
CONECT   23   24   24   25
CONECT   25   55
CONECT   26   27   28   56
CONECT   27   57
CONECT   28   29   30   58
CONECT   29   59
CONECT   30   31   60
CONECT   31   61
CONECT   32   33   33   34
CONECT   34   35
CONECT   35   62   63
END

HMDB0060491
     RDKit          3D
Mycophenolic acid O-acyl-glucuronide
 63 65  0  0  0  0  0  0  0  0999 V2000
   -2.1437    0.9755    1.6855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7561    1.5209    0.5011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9516    0.8589    0.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1495    1.2966    0.7410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1935    2.4052    1.6828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3155    0.6333    0.3912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2618   -0.4100   -0.4992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0545   -0.8466   -1.0876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0660   -1.8880   -1.9620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8957   -0.1824   -0.7391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6393   -0.6211   -1.3687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7819   -1.4969   -0.5755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4801   -1.3161   -0.3844 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1638   -0.1493   -1.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2630   -2.3134    0.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9373   -1.7830    1.6445 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9336   -0.7539    1.3645 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7124    0.4678    1.5713 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1728   -1.1049    0.8527 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2079   -0.1769    0.5559 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4684   -0.1760   -0.8352 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1710    1.0005   -1.1169 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4792    1.1005   -2.5663 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1037    2.0722   -3.0489 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0608    0.0898   -3.4096 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4513    1.0743   -0.3166 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5146    2.2378    0.4618 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6678   -0.1422    0.5271 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2266   -1.1966   -0.2226 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4608   -0.6584    1.2353 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4127   -0.2624    2.5718 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6041   -0.9307   -0.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9185   -1.8987   -1.4401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4261   -0.1637    0.1231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7086    0.8354    0.8081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5442    1.5144    2.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3770   -0.0966    1.8208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0634    1.1200    1.6431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3457    2.0860    2.7308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2168    2.9513    1.6603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9489    3.1545    1.3472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2981   -2.2470   -2.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8076   -1.0466   -2.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0613    0.3478   -1.6207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2395   -2.3833   -0.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1628   -0.0975   -2.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0975    0.7696   -0.4691 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2733   -0.2436   -1.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9925   -2.8883   -0.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4323   -3.1153    0.7769 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4942   -2.6286    2.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1565   -1.4611    2.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9021    0.8446    0.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5315    1.8438   -0.7922 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1123    0.1157   -3.8141 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3094    1.1356   -1.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3878    2.3635    0.8695 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4030    0.1480    1.3319 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9988   -1.1061   -1.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4133   -1.7917    1.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4814    0.0160    2.8340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0828    1.8382    0.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8396    0.7590    1.9094 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  2  0
 23 25  1  0
 22 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
  7 32  1  0
 32 33  2  0
 32 34  1  0
 34 35  1  0
 10  3  1  0
 30 20  1  0
 35  6  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  5 39  1  0
  5 40  1  0
  5 41  1  0
  9 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 14 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  0
 15 50  1  0
 16 51  1  0
 16 52  1  0
 20 53  1  1
 22 54  1  1
 25 55  1  0
 26 56  1  6
 27 57  1  0
 28 58  1  1
 29 59  1  0
 30 60  1  1
 31 61  1  0
 35 62  1  0
 35 63  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
AcMPAG	ChEBI
Mycophenolic acid acyl glucuronide	ChEBI
Mycophenolic acid acyl-glucuronide	ChEBI
Mycophenolic acid-O-acyl-beta-D-glucopyranuronoside	ChEBI
Mycophenolate acyl glucuronide	Generator
Mycophenolate acyl-glucuronide	Generator
Mycophenolate-O-acyl-b-D-glucopyranuronoside	Generator
Mycophenolate-O-acyl-beta-D-glucopyranuronoside	Generator
Mycophenolate-O-acyl-β-D-glucopyranuronoside	Generator
Mycophenolic acid-O-acyl-b-D-glucopyranuronoside	Generator
Mycophenolic acid-O-acyl-β-D-glucopyranuronoside	Generator
Mycophenolate O-acyl-glucuronide	Generator

Chemical Formula

C₂₃H₂₈O₁₂

Average Molecular Weight

496.4612

Monoisotopic Molecular Weight

496.15807636

IUPAC Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoyl]oxy}oxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methylhex-4-enoyl]oxy}oxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C\C=C(/C)CCC(=O)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C23H28O12/c1-9(4-6-11-15(25)14-12(8-33-22(14)31)10(2)19(11)32-3)5-7-13(24)34-23-18(28)16(26)17(27)20(35-23)21(29)30/h4,16-18,20,23,25-28H,5-8H2,1-3H3,(H,29,30)/b9-4+/t16-,17-,18+,20-,23+/m0/s1

InChI Key

QBMSTEZXAMABFF-UEARNRKISA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glucuronides

Alternative Parents

Substituents

1-o-glucuronide
O-glucuronide
Isobenzofuranone
Phthalide
Isocoumaran
Tricarboxylic acid or derivatives
Anisole
Alkyl aryl ether
Beta-hydroxy acid
Fatty acid ester
Fatty acyl
Hydroxy acid
Benzenoid
Monosaccharide
Pyran
Oxane
Vinylogous acid
Secondary alcohol
Lactone
Carboxylic acid ester
Acetal
Organoheterocyclic compound
Ether
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Polyol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

carboxylic ester (CHEBI:64689 )
phenols (CHEBI:64689 )
gamma-lactone (CHEBI:64689 )
beta-D-glucosiduronic acid (CHEBI:64689 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060491)

Organ

Liver (HMDB: HMDB0060491)
Kidney (HMDB: HMDB0060491)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060491)

Cellular substructure

Cytoplasm (HMDB: HMDB0060491)

Source

Endogenous

Endogenous (HMDB: HMDB0060491)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Mycophenolic Acid Metabolism Pathway (PathBank: SMP0000652)

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.72 g/L	ALOGPS
logP	0.91	ALOGPS
logP	1.58	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.26	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	189.28 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	117.53 m³·mol⁻¹	ChemAxon
Polarizability	49.24 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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
DeepCCS	[M+H]+	204.797	30932474
DeepCCS	[M-H]-	202.972	30932474
DeepCCS	[M-2H]-	236.213	30932474
DeepCCS	[M+Na]+	211.03	30932474
AllCCS	[M+H]+	214.9	32859911
AllCCS	[M+H-H2O]+	212.9	32859911
AllCCS	[M+NH4]+	216.7	32859911
AllCCS	[M+Na]+	217.2	32859911
AllCCS	[M-H]-	212.2	32859911
AllCCS	[M+Na-2H]-	213.6	32859911
AllCCS	[M+HCOO]-	215.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.08 minutes	32390414
Predicted by Siyang on May 30, 2022	12.9613 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.88 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2443.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	185.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	136.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	157.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	89.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	458.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	525.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	109.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	970.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	491.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1491.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	330.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	375.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	267.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	144.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	59.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Mycophenolic acid O-acyl-glucuronide	COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C\C=C(/C)CCC(=O)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O	5129.2	Standard polar	33892256
Mycophenolic acid O-acyl-glucuronide	COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C\C=C(/C)CCC(=O)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O	3509.9	Standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide	COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C\C=C(/C)CCC(=O)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O	4009.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Mycophenolic acid O-acyl-glucuronide,1TMS,isomer #1	COC1=C(C)C2=C(C(=O)OC2)C(O[Si](C)(C)C)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O	3718.3	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,1TMS,isomer #2	COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	3701.5	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,1TMS,isomer #3	COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	3689.3	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,1TMS,isomer #4	COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	3698.0	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,1TMS,isomer #5	COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]1O	3681.2	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,2TMS,isomer #1	COC1=C(C)C2=C(C(=O)OC2)C(O[Si](C)(C)C)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]1O	3696.4	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,2TMS,isomer #10	COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	3667.9	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,2TMS,isomer #2	COC1=C(C)C2=C(C(=O)OC2)C(O[Si](C)(C)C)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	3712.2	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,2TMS,isomer #3	COC1=C(C)C2=C(C(=O)OC2)C(O[Si](C)(C)C)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	3697.7	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,2TMS,isomer #4	COC1=C(C)C2=C(C(=O)OC2)C(O[Si](C)(C)C)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	3705.7	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,2TMS,isomer #5	COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	3678.3	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,2TMS,isomer #6	COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	3676.4	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,2TMS,isomer #7	COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	3692.4	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,2TMS,isomer #8	COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	3657.0	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,2TMS,isomer #9	COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	3682.2	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,3TMS,isomer #1	COC1=C(C)C2=C(C(=O)OC2)C(O[Si](C)(C)C)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	3694.9	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,3TMS,isomer #10	COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	3650.1	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,3TMS,isomer #2	COC1=C(C)C2=C(C(=O)OC2)C(O[Si](C)(C)C)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	3678.2	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,3TMS,isomer #3	COC1=C(C)C2=C(C(=O)OC2)C(O[Si](C)(C)C)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	3686.0	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,3TMS,isomer #4	COC1=C(C)C2=C(C(=O)OC2)C(O[Si](C)(C)C)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	3693.4	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,3TMS,isomer #5	COC1=C(C)C2=C(C(=O)OC2)C(O[Si](C)(C)C)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	3700.0	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,3TMS,isomer #6	COC1=C(C)C2=C(C(=O)OC2)C(O[Si](C)(C)C)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	3686.3	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,3TMS,isomer #7	COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	3654.3	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,3TMS,isomer #8	COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	3677.4	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,3TMS,isomer #9	COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	3679.3	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,4TMS,isomer #1	COC1=C(C)C2=C(C(=O)OC2)C(O[Si](C)(C)C)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	3682.6	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,4TMS,isomer #2	COC1=C(C)C2=C(C(=O)OC2)C(O[Si](C)(C)C)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	3699.1	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,4TMS,isomer #3	COC1=C(C)C2=C(C(=O)OC2)C(O[Si](C)(C)C)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	3680.7	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,4TMS,isomer #4	COC1=C(C)C2=C(C(=O)OC2)C(O[Si](C)(C)C)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	3689.9	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,4TMS,isomer #5	COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	3678.1	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,5TMS,isomer #1	COC1=C(C)C2=C(C(=O)OC2)C(O[Si](C)(C)C)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	3697.2	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,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)O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O	3955.5	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,1TBDMS,isomer #2	COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O	3910.8	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,1TBDMS,isomer #3	COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	3901.1	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,1TBDMS,isomer #4	COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3914.3	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,1TBDMS,isomer #5	COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]1O	3907.8	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,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[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]1O	4136.6	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,2TBDMS,isomer #10	COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	4107.0	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,2TBDMS,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[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O	4146.0	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,2TBDMS,isomer #3	COC1=C(C)C2=C(C(=O)OC2)C(O[Si](C)(C)C(C)(C)C)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	4139.7	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,2TBDMS,isomer #4	COC1=C(C)C2=C(C(=O)OC2)C(O[Si](C)(C)C(C)(C)C)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	4146.9	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,2TBDMS,isomer #5	COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O	4106.1	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,2TBDMS,isomer #6	COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	4097.3	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,2TBDMS,isomer #7	COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	4115.1	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,2TBDMS,isomer #8	COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	4091.3	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,2TBDMS,isomer #9	COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	4105.6	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,3TBDMS,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[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O	4324.1	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,3TBDMS,isomer #10	COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	4293.1	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,3TBDMS,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[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	4316.5	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,3TBDMS,isomer #3	COC1=C(C)C2=C(C(=O)OC2)C(O[Si](C)(C)C(C)(C)C)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	4320.8	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,3TBDMS,isomer #4	COC1=C(C)C2=C(C(=O)OC2)C(O[Si](C)(C)C(C)(C)C)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	4310.9	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,3TBDMS,isomer #5	COC1=C(C)C2=C(C(=O)OC2)C(O[Si](C)(C)C(C)(C)C)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	4320.1	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,3TBDMS,isomer #6	COC1=C(C)C2=C(C(=O)OC2)C(O[Si](C)(C)C(C)(C)C)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	4311.7	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,3TBDMS,isomer #7	COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	4287.7	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,3TBDMS,isomer #8	COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	4322.6	Semi standard non polar	33892256
Mycophenolic acid O-acyl-glucuronide,3TBDMS,isomer #9	COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C/C=C(\C)CCC(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	4302.4	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 O-acyl-glucuronide GC-MS (Non-derivatized) - 70eV, Positive	splash10-056r-9132400000-8d1d445b5c92387b8fdd	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mycophenolic acid O-acyl-glucuronide GC-MS (2 TMS) - 70eV, Positive	splash10-004i-9807007000-7f6173b63131c0199045	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mycophenolic acid O-acyl-glucuronide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mycophenolic acid O-acyl-glucuronide GC-MS (TBDMS_3_6) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mycophenolic acid O-acyl-glucuronide GC-MS ("Mycophenolic acid O-acyl-glucuronide,3TBDMS,#6" TMS) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mycophenolic acid O-acyl-glucuronide 10V, Positive-QTOF	splash10-0fi1-0539500000-bfc6fff89aeca9bc0aeb	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mycophenolic acid O-acyl-glucuronide 20V, Positive-QTOF	splash10-0kk9-1898200000-2b4abbcf7a3d676e09ff	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mycophenolic acid O-acyl-glucuronide 40V, Positive-QTOF	splash10-004i-3951000000-bf27b3a68a384eb61846	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mycophenolic acid O-acyl-glucuronide 10V, Negative-QTOF	splash10-0udi-1229400000-a00fd0b14652a8a073e4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mycophenolic acid O-acyl-glucuronide 20V, Negative-QTOF	splash10-0v00-3927200000-b03a15a97c3652e63eb5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mycophenolic acid O-acyl-glucuronide 40V, Negative-QTOF	splash10-0miy-9725000000-7d44f74d3818db669d41	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mycophenolic acid O-acyl-glucuronide 10V, Positive-QTOF	splash10-0002-0032900000-688e9215c56e8c6bc792	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mycophenolic acid O-acyl-glucuronide 20V, Positive-QTOF	splash10-0a4i-0091000000-e2000425e22fefbd07ad	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mycophenolic acid O-acyl-glucuronide 40V, Positive-QTOF	splash10-014j-0091100000-9d561f09ce0219cf3eaa	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mycophenolic acid O-acyl-glucuronide 10V, Negative-QTOF	splash10-0002-0001900000-3a9bf5cebae751792dee	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mycophenolic acid O-acyl-glucuronide 20V, Negative-QTOF	splash10-0ktb-2054900000-3d6868acf21096f78353	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mycophenolic acid O-acyl-glucuronide 40V, Negative-QTOF	splash10-052g-1192200000-4eb5e92df9f368cdbdd2	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

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	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C20383

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10028772

PDB ID

Not Available

ChEBI ID

64689

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

Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

Enzyme Details

1. 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 O-acyl-glucuronide (HMDB0060491)

MOL for HMDB0060491 (Mycophenolic acid O-acyl-glucuronide)

3D MOL for HMDB0060491 (Mycophenolic acid O-acyl-glucuronide)

3D SDF for HMDB0060491 (Mycophenolic acid O-acyl-glucuronide)

3D-SDF for HMDB0060491 (Mycophenolic acid O-acyl-glucuronide)

PDB for HMDB0060491 (Mycophenolic acid O-acyl-glucuronide)

3D PDB for HMDB0060491 (Mycophenolic acid O-acyl-glucuronide)

SMILES for HMDB0060491 (Mycophenolic acid O-acyl-glucuronide)

INCHI for HMDB0060491 (Mycophenolic acid O-acyl-glucuronide)

Structure for HMDB0060491 (Mycophenolic acid O-acyl-glucuronide)

3D Structure for HMDB0060491 (Mycophenolic acid O-acyl-glucuronide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions