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

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2008-09-15 17:42:30 UTC

Update Date

2022-09-22 17:43:57 UTC

HMDB ID

HMDB0010343

Secondary Accession Numbers

HMDB0060919
HMDB10343
HMDB60919

Metabolite Identification

Common Name

Ibuprofen glucuronide

Description

Ibuprofen glucuronide (CAS: 115075-59-7) is a natural human metabolite of ibuprofen generated in the liver by UDP glucuonyltransferase. Glucuronidation is used to assist in the excretion of toxic substances, drugs, or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys.

Structure

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


  Mrv1652306261919022D          

 27 28  0  0  0  0            999 V2000
 9997.6795 9998.1072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.3943 9998.5191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1091 9998.1072    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.1091 9997.2818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.9690 9999.7575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.6829 9999.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.3968 9999.7575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.6829 9998.5191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.3943 9999.3448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.250110000.5828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.535210000.9955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.964810000.9955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.2501 9997.2818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.8205 9998.1072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.8205 9999.7575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.2501 9999.7571    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9995.5356 9999.3446    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9995.5356 9998.5196    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9996.2501 9998.1072    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.9645 9998.5196    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9996.9645 9999.3446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.2534 9999.3446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.5391 9999.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.8245 9999.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.8245 9998.5196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.5390 9998.1071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.2534 9998.5196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  9  2  0  0  0  0
  3  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 16 21  1  0  0  0  0
 20 21  1  0  0  0  0
 20  1  1  1  0  0  0
 16 10  1  1  0  0  0
 17 15  1  6  0  0  0
 18 14  1  1  0  0  0
 19 13  1  6  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 22  1  0  0  0  0
  3 25  1  0  0  0  0
 22  5  1  0  0  0  0
M  END

HMDB0010343
     RDKit          3D
Ibuprofen glucuronide
 53 54  0  0  0  0  0  0  0  0999 V2000
   -4.6881    2.0192   -0.7617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4728    0.9209   -1.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9041    1.3556   -1.5957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4565   -0.3590   -0.6131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0585   -0.8350   -0.4371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5035   -1.6944   -1.3554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1931   -2.1419   -1.1924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4642   -1.7208   -0.1140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0640   -2.1360    0.1531 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0368   -2.8818    1.4493 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7626   -0.9001    0.1845 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2666    0.2552    0.0039 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1406   -0.9247    0.4146 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9066    0.2825    0.4384 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7957    0.1885   -0.6358 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7484    1.1910   -0.6257 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5777    1.0253   -1.8487 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5386    1.8043   -2.1139 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3489    0.0065   -2.7738 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6953    1.0720    0.5653 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6989    2.2639    1.2824 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0967    0.0062    1.4761 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0286   -1.1837    0.7326 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6519    0.4532    1.7171 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7134    1.8046    2.0301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0486   -0.8595    0.7887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3447   -0.3961    0.6581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9585    2.0648    0.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9266    2.9784   -1.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6078    1.8054   -0.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0585    0.7271   -2.4444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3062    0.9973   -2.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5185    0.9765   -0.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9273    2.4800   -1.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0192   -1.1173   -1.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9772   -0.1772    0.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0567   -2.0468   -2.2222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7345   -2.8187   -1.9021 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2402   -2.8209   -0.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5192   -3.8498    1.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3942   -2.2460    2.2493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0618   -3.1534    1.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2827    1.1654    0.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2918    2.2012   -0.6818 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5180   -0.0822   -3.3214 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7231    0.8202    0.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8843    3.0402    0.6889 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6574   -0.1082    2.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9322   -1.5021    0.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2059   -0.0805    2.5746 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0384    2.3376    1.5080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5077   -0.4928    1.6688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7629    0.2856    1.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 16 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
  8 26  1  0
 26 27  2  0
 27  5  1  0
 24 14  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  6 37  1  0
  7 38  1  0
  9 39  1  6
 10 40  1  0
 10 41  1  0
 10 42  1  0
 14 43  1  6
 16 44  1  6
 19 45  1  0
 20 46  1  6
 21 47  1  0
 22 48  1  1
 23 49  1  0
 24 50  1  1
 25 51  1  0
 26 52  1  0
 27 53  1  0
M  END


  Mrv1652306261919022D          

 27 28  0  0  0  0            999 V2000
 9997.6795 9998.1072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.3943 9998.5191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1091 9998.1072    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.1091 9997.2818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.9690 9999.7575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.6829 9999.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.3968 9999.7575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.6829 9998.5191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.3943 9999.3448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.250110000.5828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.535210000.9955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.964810000.9955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.2501 9997.2818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.8205 9998.1072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.8205 9999.7575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.2501 9999.7571    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9995.5356 9999.3446    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9995.5356 9998.5196    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9996.2501 9998.1072    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.9645 9998.5196    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9996.9645 9999.3446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.2534 9999.3446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.5391 9999.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.8245 9999.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.8245 9998.5196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.5390 9998.1071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.2534 9998.5196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  9  2  0  0  0  0
  3  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 16 21  1  0  0  0  0
 20 21  1  0  0  0  0
 20  1  1  1  0  0  0
 16 10  1  1  0  0  0
 17 15  1  6  0  0  0
 18 14  1  1  0  0  0
 19 13  1  6  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 22  1  0  0  0  0
  3 25  1  0  0  0  0
 22  5  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0010343

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CC1=CC=C(C=C1)[C@H](C)C(=O)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O8/c1-9(2)8-11-4-6-12(7-5-11)10(3)18(25)27-19-15(22)13(20)14(21)16(26-19)17(23)24/h4-7,9-10,13-16,19-22H,8H2,1-3H3,(H,23,24)/t10-,13-,14-,15+,16-,19-/m0/s1

> <INCHI_KEY>
ABOLXXZAJIAUGR-LEBSGKMFSA-N

> <FORMULA>
C19H26O8

> <MOLECULAR_WEIGHT>
382.409

> <EXACT_MASS>
382.162767797

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
38.40568434630554

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2S)-2-[4-(2-methylpropyl)phenyl]propanoyl]oxy}oxane-2-carboxylic acid

> <ALOGPS_LOGP>
1.37

> <JCHEM_LOGP>
1.895764644000001

> <ALOGPS_LOGS>
-2.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.212675282186826

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3988247089487853

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6868988000569773

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
93.0305

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.59e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2S)-2-[4-(2-methylpropyl)phenyl]propanoyl]oxy}oxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0010343
     RDKit          3D
Ibuprofen glucuronide
 53 54  0  0  0  0  0  0  0  0999 V2000
   -4.6881    2.0192   -0.7617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4728    0.9209   -1.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9041    1.3556   -1.5957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4565   -0.3590   -0.6131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0585   -0.8350   -0.4371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5035   -1.6944   -1.3554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1931   -2.1419   -1.1924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4642   -1.7208   -0.1140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0640   -2.1360    0.1531 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0368   -2.8818    1.4493 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7626   -0.9001    0.1845 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2666    0.2552    0.0039 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1406   -0.9247    0.4146 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9066    0.2825    0.4384 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7957    0.1885   -0.6358 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7484    1.1910   -0.6257 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5777    1.0253   -1.8487 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5386    1.8043   -2.1139 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3489    0.0065   -2.7738 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6953    1.0720    0.5653 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6989    2.2639    1.2824 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0967    0.0062    1.4761 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0286   -1.1837    0.7326 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6519    0.4532    1.7171 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7134    1.8046    2.0301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0486   -0.8595    0.7887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3447   -0.3961    0.6581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9585    2.0648    0.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9266    2.9784   -1.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6078    1.8054   -0.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0585    0.7271   -2.4444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3062    0.9973   -2.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5185    0.9765   -0.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9273    2.4800   -1.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0192   -1.1173   -1.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9772   -0.1772    0.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0567   -2.0468   -2.2222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7345   -2.8187   -1.9021 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2402   -2.8209   -0.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5192   -3.8498    1.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3942   -2.2460    2.2493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0618   -3.1534    1.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2827    1.1654    0.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2918    2.2012   -0.6818 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5180   -0.0822   -3.3214 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7231    0.8202    0.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8843    3.0402    0.6889 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6574   -0.1082    2.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9322   -1.5021    0.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2059   -0.0805    2.5746 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0384    2.3376    1.5080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5077   -0.4928    1.6688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7629    0.2856    1.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 16 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
  8 26  1  0
 26 27  2  0
 27  5  1  0
 24 14  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  6 37  1  0
  7 38  1  0
  9 39  1  6
 10 40  1  0
 10 41  1  0
 10 42  1  0
 14 43  1  6
 16 44  1  6
 19 45  1  0
 20 46  1  6
 21 47  1  0
 22 48  1  1
 23 49  1  0
 24 50  1  1
 25 51  1  0
 26 52  1  0
 27 53  1  0
M  END

HEADER    PROTEIN                                 26-JUN-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-JUN-19         0                                  
HETATM    1  O   UNK     0    8662.3358663.133   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8663.6698663.902   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8665.0048663.133   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8665.0048661.593   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8670.3428666.214   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8671.6758665.444   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8673.0078666.214   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8671.6758663.902   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    8663.6698665.444   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8659.6678667.755   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8658.3328668.525   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8661.0018668.525   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8659.6678661.593   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    8656.9988663.133   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0    8656.9988666.214   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0    8659.6678666.213   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8658.3338665.443   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8658.3338663.903   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8659.6678663.133   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8661.0008663.903   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0    8661.0008665.443   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0    8669.0068665.443   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8667.6738666.213   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8666.3398665.443   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8666.3398663.903   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8667.6738663.133   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8669.0068663.903   0.000  0.00  0.00           C+0
CONECT    1    2   20                                                       
CONECT    2    1    3    9                                                  
CONECT    3    2    4   25                                                  
CONECT    4    3                                                            
CONECT    5    6   22                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    2                                                            
CONECT   10   11   12   16                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   19                                                            
CONECT   14   18                                                            
CONECT   15   17                                                            
CONECT   16   17   21   10                                                  
CONECT   17   16   18   15                                                  
CONECT   18   17   19   14                                                  
CONECT   19   18   20   13                                                  
CONECT   20   19   21    1                                                  
CONECT   21   16   20                                                       
CONECT   22   23   27    5                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26    3                                                  
CONECT   26   25   27                                                       
CONECT   27   26   22                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

COMPND    HMDB0010343
HETATM    1  C1  UNL     1      -4.688   2.019  -0.762  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.473   0.921  -1.430  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.904   1.356  -1.596  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.456  -0.359  -0.613  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.059  -0.835  -0.437  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.504  -1.694  -1.355  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.193  -2.142  -1.192  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.464  -1.721  -0.114  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.064  -2.136   0.153  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.037  -2.882   1.449  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.763  -0.900   0.184  1.00  0.00           C  
HETATM   12  O1  UNL     1       0.267   0.255   0.004  1.00  0.00           O  
HETATM   13  O2  UNL     1       2.141  -0.925   0.415  1.00  0.00           O  
HETATM   14  C12 UNL     1       2.907   0.283   0.438  1.00  0.00           C  
HETATM   15  O3  UNL     1       3.796   0.188  -0.636  1.00  0.00           O  
HETATM   16  C13 UNL     1       4.748   1.191  -0.626  1.00  0.00           C  
HETATM   17  C14 UNL     1       5.578   1.025  -1.849  1.00  0.00           C  
HETATM   18  O4  UNL     1       6.539   1.804  -2.114  1.00  0.00           O  
HETATM   19  O5  UNL     1       5.349   0.007  -2.774  1.00  0.00           O  
HETATM   20  C15 UNL     1       5.695   1.072   0.565  1.00  0.00           C  
HETATM   21  O6  UNL     1       5.699   2.264   1.282  1.00  0.00           O  
HETATM   22  C16 UNL     1       5.097   0.006   1.476  1.00  0.00           C  
HETATM   23  O7  UNL     1       5.029  -1.184   0.733  1.00  0.00           O  
HETATM   24  C17 UNL     1       3.652   0.453   1.717  1.00  0.00           C  
HETATM   25  O8  UNL     1       3.713   1.805   2.030  1.00  0.00           O  
HETATM   26  C18 UNL     1      -2.049  -0.860   0.789  1.00  0.00           C  
HETATM   27  C19 UNL     1      -3.345  -0.396   0.658  1.00  0.00           C  
HETATM   28  H1  UNL     1      -4.958   2.065   0.321  1.00  0.00           H  
HETATM   29  H2  UNL     1      -4.927   2.978  -1.251  1.00  0.00           H  
HETATM   30  H3  UNL     1      -3.608   1.805  -0.817  1.00  0.00           H  
HETATM   31  H4  UNL     1      -5.059   0.727  -2.444  1.00  0.00           H  
HETATM   32  H5  UNL     1      -7.306   0.997  -2.560  1.00  0.00           H  
HETATM   33  H6  UNL     1      -7.519   0.976  -0.779  1.00  0.00           H  
HETATM   34  H7  UNL     1      -6.927   2.480  -1.566  1.00  0.00           H  
HETATM   35  H8  UNL     1      -6.019  -1.117  -1.199  1.00  0.00           H  
HETATM   36  H9  UNL     1      -5.977  -0.177   0.333  1.00  0.00           H  
HETATM   37  H10 UNL     1      -4.057  -2.047  -2.222  1.00  0.00           H  
HETATM   38  H11 UNL     1      -1.735  -2.819  -1.902  1.00  0.00           H  
HETATM   39  H12 UNL     1       0.240  -2.821  -0.665  1.00  0.00           H  
HETATM   40  H13 UNL     1       0.519  -3.850   1.379  1.00  0.00           H  
HETATM   41  H14 UNL     1       0.394  -2.246   2.249  1.00  0.00           H  
HETATM   42  H15 UNL     1      -1.062  -3.153   1.777  1.00  0.00           H  
HETATM   43  H16 UNL     1       2.283   1.165   0.260  1.00  0.00           H  
HETATM   44  H17 UNL     1       4.292   2.201  -0.682  1.00  0.00           H  
HETATM   45  H18 UNL     1       4.518  -0.082  -3.321  1.00  0.00           H  
HETATM   46  H19 UNL     1       6.723   0.820   0.258  1.00  0.00           H  
HETATM   47  H20 UNL     1       5.884   3.040   0.689  1.00  0.00           H  
HETATM   48  H21 UNL     1       5.657  -0.108   2.403  1.00  0.00           H  
HETATM   49  H22 UNL     1       5.932  -1.502   0.484  1.00  0.00           H  
HETATM   50  H23 UNL     1       3.206  -0.080   2.575  1.00  0.00           H  
HETATM   51  H24 UNL     1       3.038   2.338   1.508  1.00  0.00           H  
HETATM   52  H25 UNL     1      -1.508  -0.493   1.669  1.00  0.00           H  
HETATM   53  H26 UNL     1      -3.763   0.286   1.400  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3    4   31
CONECT    3   32   33   34
CONECT    4    5   35   36
CONECT    5    6    6   27
CONECT    6    7   37
CONECT    7    8    8   38
CONECT    8    9   26
CONECT    9   10   11   39
CONECT   10   40   41   42
CONECT   11   12   12   13
CONECT   13   14
CONECT   14   15   24   43
CONECT   15   16
CONECT   16   17   20   44
CONECT   17   18   18   19
CONECT   19   45
CONECT   20   21   22   46
CONECT   21   47
CONECT   22   23   24   48
CONECT   23   49
CONECT   24   25   50
CONECT   25   51
CONECT   26   27   27   52
CONECT   27   53
END

HMDB0010343
     RDKit          3D
Ibuprofen glucuronide
 53 54  0  0  0  0  0  0  0  0999 V2000
   -4.6881    2.0192   -0.7617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4728    0.9209   -1.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9041    1.3556   -1.5957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4565   -0.3590   -0.6131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0585   -0.8350   -0.4371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5035   -1.6944   -1.3554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1931   -2.1419   -1.1924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4642   -1.7208   -0.1140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0640   -2.1360    0.1531 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0368   -2.8818    1.4493 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7626   -0.9001    0.1845 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2666    0.2552    0.0039 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1406   -0.9247    0.4146 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9066    0.2825    0.4384 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7957    0.1885   -0.6358 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7484    1.1910   -0.6257 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5777    1.0253   -1.8487 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5386    1.8043   -2.1139 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3489    0.0065   -2.7738 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6953    1.0720    0.5653 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6989    2.2639    1.2824 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0967    0.0062    1.4761 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0286   -1.1837    0.7326 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6519    0.4532    1.7171 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7134    1.8046    2.0301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0486   -0.8595    0.7887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3447   -0.3961    0.6581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9585    2.0648    0.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9266    2.9784   -1.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6078    1.8054   -0.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0585    0.7271   -2.4444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3062    0.9973   -2.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5185    0.9765   -0.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9273    2.4800   -1.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0192   -1.1173   -1.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9772   -0.1772    0.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0567   -2.0468   -2.2222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7345   -2.8187   -1.9021 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2402   -2.8209   -0.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5192   -3.8498    1.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3942   -2.2460    2.2493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0618   -3.1534    1.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2827    1.1654    0.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2918    2.2012   -0.6818 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5180   -0.0822   -3.3214 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7231    0.8202    0.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8843    3.0402    0.6889 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6574   -0.1082    2.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9322   -1.5021    0.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2059   -0.0805    2.5746 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0384    2.3376    1.5080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5077   -0.4928    1.6688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7629    0.2856    1.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 16 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
  8 26  1  0
 26 27  2  0
 27  5  1  0
 24 14  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  6 37  1  0
  7 38  1  0
  9 39  1  6
 10 40  1  0
 10 41  1  0
 10 42  1  0
 14 43  1  6
 16 44  1  6
 19 45  1  0
 20 46  1  6
 21 47  1  0
 22 48  1  1
 23 49  1  0
 24 50  1  1
 25 51  1  0
 26 52  1  0
 27 53  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(S)-Ibuprofen glucuronide	HMDB
1-(alpha-Methyl-4-(2-methylpropyl)benzeneacetate)-beta-D-glucopyranuronic acid	HMDB
Ibuprofen-beta-D-glucuronide	HMDB
Ibuprofen-β-D-glucuronide	HMDB
Ibuprofen glucuronide	HMDB

Chemical Formula

C₁₉H₂₆O₈

Average Molecular Weight

382.409

Monoisotopic Molecular Weight

382.162767797

IUPAC Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2S)-2-[4-(2-methylpropyl)phenyl]propanoyl]oxy}oxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2S)-2-[4-(2-methylpropyl)phenyl]propanoyl]oxy}oxane-2-carboxylic acid

CAS Registry Number

98649-76-4

SMILES

CC(C)CC1=CC=C(C=C1)[C@H](C)C(=O)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C19H26O8/c1-9(2)8-11-4-6-12(7-5-11)10(3)18(25)27-19-15(22)13(20)14(21)16(26-19)17(23)24/h4-7,9-10,13-16,19-22H,8H2,1-3H3,(H,23,24)/t10-,13-,14-,15+,16-,19-/m0/s1

InChI Key

ABOLXXZAJIAUGR-LEBSGKMFSA-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
P-cymene
Aromatic monoterpenoid
Monocyclic monoterpenoid
Monoterpenoid
Phenylpropane
Beta-hydroxy acid
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Hydroxy acid
Monosaccharide
Benzenoid
Pyran
Oxane
Carboxylic acid ester
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Organoheterocyclic compound
Acetal
Oxacycle
Polyol
Alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 8496270)

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0010343)

Organ

Kidney (HMDB: HMDB0010343)
Liver (HMDB: HMDB0010343)

Source

Endogenous

Endogenous (HMDB: HMDB0010343)

Exogenous

Exogenous (HMDB: HMDB0010343)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Ibuprofen Action Pathway (PathBank: SMP0000086)

Metabolic pathway

Ibuprofen Metabolism Pathway (PathBank: SMP0000590)

Role

Biological role

Drug metabolite (HMDB: HMDB0010343)

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.59 g/L	ALOGPS
logP	1.37	ALOGPS
logP	1.9	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	3.4	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	93.03 m³·mol⁻¹	ChemAxon
Polarizability	38.41 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	184.555	30932474
DeepCCS	[M-H]-	182.16	30932474
DeepCCS	[M-2H]-	215.358	30932474
DeepCCS	[M+Na]+	190.328	30932474

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.	5.91 minutes	32390414
Predicted by Siyang on May 30, 2022	13.9114 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.99 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	39.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2349.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	247.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	146.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	169.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	111.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	559.0 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	629.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	76.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1013.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	550.1 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	1612.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	333.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	388.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	252.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	136.8 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	11.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ibuprofen glucuronide	CC(C)CC1=CC=C(C=C1)[C@H](C)C(=O)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O	3843.6	Standard polar	33892256
Ibuprofen glucuronide	CC(C)CC1=CC=C(C=C1)[C@H](C)C(=O)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O	2794.6	Standard non polar	33892256
Ibuprofen glucuronide	CC(C)CC1=CC=C(C=C1)[C@H](C)C(=O)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O	2957.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ibuprofen glucuronide,1TMS,isomer #1	CC(C)CC1=CC=C([C@H](C)C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O)C=C1	2751.9	Semi standard non polar	33892256
Ibuprofen glucuronide,1TMS,isomer #2	CC(C)CC1=CC=C([C@H](C)C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O)C=C1	2748.0	Semi standard non polar	33892256
Ibuprofen glucuronide,1TMS,isomer #3	CC(C)CC1=CC=C([C@H](C)C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C)C=C1	2745.3	Semi standard non polar	33892256
Ibuprofen glucuronide,1TMS,isomer #4	CC(C)CC1=CC=C([C@H](C)C(=O)O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]2O)C=C1	2722.6	Semi standard non polar	33892256
Ibuprofen glucuronide,2TMS,isomer #1	CC(C)CC1=CC=C([C@H](C)C(=O)O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O)C=C1	2746.6	Semi standard non polar	33892256
Ibuprofen glucuronide,2TMS,isomer #2	CC(C)CC1=CC=C([C@H](C)C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O)C=C1	2753.5	Semi standard non polar	33892256
Ibuprofen glucuronide,2TMS,isomer #3	CC(C)CC1=CC=C([C@H](C)C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C)C=C1	2753.8	Semi standard non polar	33892256
Ibuprofen glucuronide,2TMS,isomer #4	CC(C)CC1=CC=C([C@H](C)C(=O)O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O)C=C1	2738.5	Semi standard non polar	33892256
Ibuprofen glucuronide,2TMS,isomer #5	CC(C)CC1=CC=C([C@H](C)C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=C1	2739.7	Semi standard non polar	33892256
Ibuprofen glucuronide,2TMS,isomer #6	CC(C)CC1=CC=C([C@H](C)C(=O)O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C)C=C1	2727.3	Semi standard non polar	33892256
Ibuprofen glucuronide,3TMS,isomer #1	CC(C)CC1=CC=C([C@H](C)C(=O)O[C@@H]2O[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]2O)C=C1	2783.1	Semi standard non polar	33892256
Ibuprofen glucuronide,3TMS,isomer #2	CC(C)CC1=CC=C([C@H](C)C(=O)O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C)C=C1	2797.2	Semi standard non polar	33892256
Ibuprofen glucuronide,3TMS,isomer #3	CC(C)CC1=CC=C([C@H](C)C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=C1	2780.2	Semi standard non polar	33892256
Ibuprofen glucuronide,3TMS,isomer #4	CC(C)CC1=CC=C([C@H](C)C(=O)O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=C1	2773.2	Semi standard non polar	33892256
Ibuprofen glucuronide,4TMS,isomer #1	CC(C)CC1=CC=C([C@H](C)C(=O)O[C@@H]2O[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]2O[Si](C)(C)C)C=C1	2828.7	Semi standard non polar	33892256
Ibuprofen glucuronide,1TBDMS,isomer #1	CC(C)CC1=CC=C([C@H](C)C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]2O)C=C1	3017.7	Semi standard non polar	33892256
Ibuprofen glucuronide,1TBDMS,isomer #2	CC(C)CC1=CC=C([C@H](C)C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=C1	3018.3	Semi standard non polar	33892256
Ibuprofen glucuronide,1TBDMS,isomer #3	CC(C)CC1=CC=C([C@H](C)C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1	3021.5	Semi standard non polar	33892256
Ibuprofen glucuronide,1TBDMS,isomer #4	CC(C)CC1=CC=C([C@H](C)C(=O)O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]2O)C=C1	3001.4	Semi standard non polar	33892256
Ibuprofen glucuronide,2TBDMS,isomer #1	CC(C)CC1=CC=C([C@H](C)C(=O)O[C@@H]2O[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]2O)C=C1	3257.1	Semi standard non polar	33892256
Ibuprofen glucuronide,2TBDMS,isomer #2	CC(C)CC1=CC=C([C@H](C)C(=O)O[C@@H]2O[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]2O)C=C1	3235.6	Semi standard non polar	33892256
Ibuprofen glucuronide,2TBDMS,isomer #3	CC(C)CC1=CC=C([C@H](C)C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1	3243.4	Semi standard non polar	33892256
Ibuprofen glucuronide,2TBDMS,isomer #4	CC(C)CC1=CC=C([C@H](C)C(=O)O[C@@H]2O[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]2O)C=C1	3253.0	Semi standard non polar	33892256
Ibuprofen glucuronide,2TBDMS,isomer #5	CC(C)CC1=CC=C([C@H](C)C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1	3232.8	Semi standard non polar	33892256
Ibuprofen glucuronide,2TBDMS,isomer #6	CC(C)CC1=CC=C([C@H](C)C(=O)O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1	3254.3	Semi standard non polar	33892256
Ibuprofen glucuronide,3TBDMS,isomer #1	CC(C)CC1=CC=C([C@H](C)C(=O)O[C@@H]2O[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]2O)C=C1	3454.8	Semi standard non polar	33892256
Ibuprofen glucuronide,3TBDMS,isomer #2	CC(C)CC1=CC=C([C@H](C)C(=O)O[C@@H]2O[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]2O[Si](C)(C)C(C)(C)C)C=C1	3479.5	Semi standard non polar	33892256
Ibuprofen glucuronide,3TBDMS,isomer #3	CC(C)CC1=CC=C([C@H](C)C(=O)O[C@@H]2O[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]2O[Si](C)(C)C(C)(C)C)C=C1	3444.9	Semi standard non polar	33892256
Ibuprofen glucuronide,3TBDMS,isomer #4	CC(C)CC1=CC=C([C@H](C)C(=O)O[C@@H]2O[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]2O[Si](C)(C)C(C)(C)C)C=C1	3447.7	Semi standard non polar	33892256
Ibuprofen glucuronide,4TBDMS,isomer #1	CC(C)CC1=CC=C([C@H](C)C(=O)O[C@@H]2O[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]2O[Si](C)(C)C(C)(C)C)C=C1	3659.3	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Ibuprofen Action Pathway		Not Available
Ibuprofen Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	13.0 (0.26-26.16) uM	Adult (>18 years old)	Both	Normal	8496270	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

58994670

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

92278491

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Castillo M, Smith PC: Disposition and reactivity of ibuprofen and ibufenac acyl glucuronides in vivo in the rhesus monkey and in vitro with human serum albumin. Drug Metab Dispos. 1995 May;23(5):566-72. [PubMed:7587932 ]
Castillo M, Lam YW, Dooley MA, Stahl E, Smith PC: Disposition and covalent binding of ibuprofen and its acyl glucuronide in the elderly. Clin Pharmacol Ther. 1995 Jun;57(6):636-44. [PubMed:7781263 ]
Castillo M, Smith PC: Direct determination of ibuprofen and ibuprofen acyl glucuronide in plasma by high-performance liquid chromatography using solid-phase extraction. J Chromatogr. 1993 Apr 21;614(1):109-16. [PubMed:8496270 ]

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

Show all enzymes and transporters

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 2B28

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

Enzyme Details

2. UDP-glucuronosyltransferase 2B4

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

References

Kuehl GE, Lampe JW, Potter JD, Bigler J: Glucuronidation of nonsteroidal anti-inflammatory drugs: identifying the enzymes responsible in human liver microsomes. Drug Metab Dispos. 2005 Jul;33(7):1027-35. Epub 2005 Apr 20. [PubMed:15843492 ]

Enzyme Details

3. UDP-glucuronosyltransferase 1-4

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

Enzyme Details

4. UDP-glucuronosyltransferase 2B7

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

References

Kuehl GE, Lampe JW, Potter JD, Bigler J: Glucuronidation of nonsteroidal anti-inflammatory drugs: identifying the enzymes responsible in human liver microsomes. Drug Metab Dispos. 2005 Jul;33(7):1027-35. Epub 2005 Apr 20. [PubMed:15843492 ]

Enzyme Details

5. UDP-glucuronosyltransferase 2B15

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

Enzyme Details

6. UDP-glucuronosyltransferase 2A1

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

Enzyme Details

7. UDP-glucuronosyltransferase 1-1

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

References

Kuehl GE, Lampe JW, Potter JD, Bigler J: Glucuronidation of nonsteroidal anti-inflammatory drugs: identifying the enzymes responsible in human liver microsomes. Drug Metab Dispos. 2005 Jul;33(7):1027-35. Epub 2005 Apr 20. [PubMed:15843492 ]

Enzyme Details

8. UDP-glucuronosyltransferase 1-9

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

References

Kuehl GE, Lampe JW, Potter JD, Bigler J: Glucuronidation of nonsteroidal anti-inflammatory drugs: identifying the enzymes responsible in human liver microsomes. Drug Metab Dispos. 2005 Jul;33(7):1027-35. Epub 2005 Apr 20. [PubMed:15843492 ]

Enzyme Details

9. UDP-glucuronosyltransferase 1-3

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

References

Kuehl GE, Lampe JW, Potter JD, Bigler J: Glucuronidation of nonsteroidal anti-inflammatory drugs: identifying the enzymes responsible in human liver microsomes. Drug Metab Dispos. 2005 Jul;33(7):1027-35. Epub 2005 Apr 20. [PubMed:15843492 ]

Enzyme Details

10. UDP-glucuronosyltransferase 2B17

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

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

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Showing metabocard for Ibuprofen glucuronide (HMDB0010343)

MOL for HMDB0010343 (Ibuprofen glucuronide)

3D MOL for HMDB0010343 (Ibuprofen glucuronide)

3D SDF for HMDB0010343 (Ibuprofen glucuronide)

3D-SDF for HMDB0010343 (Ibuprofen glucuronide)

PDB for HMDB0010343 (Ibuprofen glucuronide)

3D PDB for HMDB0010343 (Ibuprofen glucuronide)

SMILES for HMDB0010343 (Ibuprofen glucuronide)

INCHI for HMDB0010343 (Ibuprofen glucuronide)

Structure for HMDB0010343 (Ibuprofen glucuronide)

3D Structure for HMDB0010343 (Ibuprofen glucuronide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

References

References

References

References

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