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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:07:28 UTC

Update Date

2021-09-14 14:58:51 UTC

HMDB ID

HMDB0060923

Secondary Accession Numbers

HMDB60923

Metabolite Identification

Common Name

Naproxen O-glucuronide

Description

Naproxen O-glucuronide is a metabolite of naproxen. Naproxen sodium is a nonsteroidal anti-inflammatory drug (NSAID). Naproxen and naproxen sodium are marketed under various trade names, including: Aleve, Anaprox, Antalgin, Feminax Ultra, Flanax, Inza, Midol Extended Relief, Nalgesin, Naposin, Naprelan, Naprogesic, Naprosyn, Narocin, Proxen, Synflex and Xenobid. Naproxen was originally marketed as the prescription drug Naprosyn by Syntex in 1976, and naproxen sodium was first marketed under the trade name Anaprox in 1980. (Wikipedia)

Structure

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

  Mrv0541 07091309072D          

 29 31  0  0  0  0            999 V2000
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    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
   -3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  5  1  0  0  0  0
  9  1  1  1  0  0  0
 10  3  1  0  0  0  0
 10  7  2  0  0  0  0
 10  9  1  0  0  0  0
 11  5  2  0  0  0  0
 11  7  1  0  0  0  0
 12  4  1  0  0  0  0
 12  8  2  0  0  0  0
 12 11  1  0  0  0  0
 13  6  2  0  0  0  0
 13  8  1  0  0  0  0
 15 14  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 17 18  1  6  0  0  0
 19  9  1  0  0  0  0
 20 16  1  0  0  0  0
 14 21  1  6  0  0  0
 15 22  1  1  0  0  0
 16 23  1  1  0  0  0
 24 18  2  0  0  0  0
 25 18  1  0  0  0  0
 26 19  2  0  0  0  0
 27  2  1  0  0  0  0
 27 13  1  0  0  0  0
 28 17  1  0  0  0  0
 28 20  1  0  0  0  0
 29 19  1  0  0  0  0
 29 20  1  0  0  0  0
M  END

HMDB0060923
     RDKit          3D
Naproxen O-glucuronide
 51 53  0  0  0  0  0  0  0  0999 V2000
    7.0283   -0.7796    1.9437 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6338   -1.7195    0.9898 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4649   -1.6102    0.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1681   -2.6110   -0.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9971   -2.4780   -1.3862 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1286   -1.4198   -1.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9633   -1.3208   -1.9571 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0930   -0.2643   -1.7952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1826   -0.1360   -2.5874 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1164    1.1202   -3.4588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3544   -0.1148   -1.6979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2360   -1.0002   -1.8139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5584    0.8415   -0.7132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6482    0.8925    0.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3261    0.8208    1.4885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4423    0.3525    2.1587 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2950   -1.1406    2.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1717   -1.8437    2.8235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1971   -1.8105    1.7340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7457    0.7578    1.6080 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6809    1.0245    2.6292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7601    1.9139    0.6744 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6977    1.6968   -0.3636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4481    2.1946    0.0063 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7976    3.1938    0.7403 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4374    0.6913   -0.8644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6049    0.5996   -0.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4691   -0.4608   -0.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6338   -0.5430    0.4568 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2099   -0.4224    2.6023 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5169    0.1204    1.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7933   -1.2103    2.6514 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8441   -3.4538   -0.8137 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7503   -3.2363   -2.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7133   -2.0850   -2.6842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2895   -0.9875   -3.2865 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9449    1.3970   -3.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4843    0.8905   -4.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6912    1.9459   -2.9908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3346    0.0521   -0.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3604    0.7208    3.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3249   -2.6065    1.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1844   -0.1252    1.0539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7608    0.2005    3.1516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0958    2.8560    1.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6981    0.7290   -0.5624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5674    2.4655   -1.0540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4743    2.8135    1.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7577    1.5214   -0.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8808    1.3425    0.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8904    0.2246    1.1904 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
  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 28  1  0
 28 29  2  0
 29  3  1  0
 28  6  1  0
 24 14  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  5 34  1  0
  7 35  1  0
  9 36  1  6
 10 37  1  0
 10 38  1  0
 10 39  1  0
 14 40  1  0
 16 41  1  1
 19 42  1  0
 20 43  1  6
 21 44  1  0
 22 45  1  1
 23 46  1  0
 24 47  1  6
 25 48  1  0
 26 49  1  0
 27 50  1  0
 29 51  1  0
M  END

  Mrv0541 07091309072D          

 29 31  0  0  0  0            999 V2000
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    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
   -3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  5  1  0  0  0  0
  9  1  1  1  0  0  0
 10  3  1  0  0  0  0
 10  7  2  0  0  0  0
 10  9  1  0  0  0  0
 11  5  2  0  0  0  0
 11  7  1  0  0  0  0
 12  4  1  0  0  0  0
 12  8  2  0  0  0  0
 12 11  1  0  0  0  0
 13  6  2  0  0  0  0
 13  8  1  0  0  0  0
 15 14  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 17 18  1  6  0  0  0
 19  9  1  0  0  0  0
 20 16  1  0  0  0  0
 14 21  1  6  0  0  0
 15 22  1  1  0  0  0
 16 23  1  1  0  0  0
 24 18  2  0  0  0  0
 25 18  1  0  0  0  0
 26 19  2  0  0  0  0
 27  2  1  0  0  0  0
 27 13  1  0  0  0  0
 28 17  1  0  0  0  0
 28 20  1  0  0  0  0
 29 19  1  0  0  0  0
 29 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060923

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C2C=C(C=CC2=C1)[C@H](C)C(=O)OC1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O9/c1-9(10-3-4-12-8-13(27-2)6-5-11(12)7-10)19(26)29-20-16(23)14(21)15(22)17(28-20)18(24)25/h3-9,14-17,20-23H,1-2H3,(H,24,25)/t9-,14-,15-,16+,17-,20?/m0/s1

> <INCHI_KEY>
XRHIELLXTVJOKM-WDZACEAPSA-N

> <FORMULA>
C20H22O9

> <MOLECULAR_WEIGHT>
406.3833

> <EXACT_MASS>
406.126382302

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
40.48415643186931

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.84

> <JCHEM_LOGP>
1.0379923193333331

> <ALOGPS_LOGS>
-2.66

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.212675282236923

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4355199002465615

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6868988000569836

> <JCHEM_POLAR_SURFACE_AREA>
142.75

> <JCHEM_REFRACTIVITY>
97.15209999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.95e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060923
     RDKit          3D
Naproxen O-glucuronide
 51 53  0  0  0  0  0  0  0  0999 V2000
    7.0283   -0.7796    1.9437 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6338   -1.7195    0.9898 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4649   -1.6102    0.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1681   -2.6110   -0.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9971   -2.4780   -1.3862 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1286   -1.4198   -1.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9633   -1.3208   -1.9571 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0930   -0.2643   -1.7952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1826   -0.1360   -2.5874 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1164    1.1202   -3.4588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3544   -0.1148   -1.6979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2360   -1.0002   -1.8139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5584    0.8415   -0.7132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6482    0.8925    0.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3261    0.8208    1.4885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4423    0.3525    2.1587 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2950   -1.1406    2.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1717   -1.8437    2.8235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1971   -1.8105    1.7340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7457    0.7578    1.6080 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6809    1.0245    2.6292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7601    1.9139    0.6744 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6977    1.6968   -0.3636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4481    2.1946    0.0063 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7976    3.1938    0.7403 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4374    0.6913   -0.8644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6049    0.5996   -0.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4691   -0.4608   -0.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6338   -0.5430    0.4568 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2099   -0.4224    2.6023 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5169    0.1204    1.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7933   -1.2103    2.6514 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8441   -3.4538   -0.8137 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7503   -3.2363   -2.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7133   -2.0850   -2.6842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2895   -0.9875   -3.2865 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9449    1.3970   -3.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4843    0.8905   -4.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6912    1.9459   -2.9908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3346    0.0521   -0.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3604    0.7208    3.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3249   -2.6065    1.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1844   -0.1252    1.0539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7608    0.2005    3.1516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0958    2.8560    1.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6981    0.7290   -0.5624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5674    2.4655   -1.0540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4743    2.8135    1.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7577    1.5214   -0.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8808    1.3425    0.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8904    0.2246    1.1904 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
  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 28  1  0
 28 29  2  0
 29  3  1  0
 28  6  1  0
 24 14  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  5 34  1  0
  7 35  1  0
  9 36  1  6
 10 37  1  0
 10 38  1  0
 10 39  1  0
 14 40  1  0
 16 41  1  1
 19 42  1  0
 20 43  1  6
 21 44  1  0
 22 45  1  1
 23 46  1  0
 24 47  1  6
 25 48  1  0
 26 49  1  0
 27 50  1  0
 29 51  1  0
M  END

HEADER    PROTEIN                                 09-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-13         0                                  
HETATM    1  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   27                                                            
CONECT    3    4   10                                                       
CONECT    4    3   12                                                       
CONECT    5    6   11                                                       
CONECT    6    5   13                                                       
CONECT    7   10   11                                                       
CONECT    8   12   13                                                       
CONECT    9    1   10   19                                                  
CONECT   10    3    7    9                                                  
CONECT   11    5    7   12                                                  
CONECT   12    4    8   11                                                  
CONECT   13    6    8   27                                                  
CONECT   14   15   16   21                                                  
CONECT   15   14   17   22                                                  
CONECT   16   14   20   23                                                  
CONECT   17   15   18   28                                                  
CONECT   18   17   24   25                                                  
CONECT   19    9   26   29                                                  
CONECT   20   16   28   29                                                  
CONECT   21   14                                                            
CONECT   22   15                                                            
CONECT   23   16                                                            
CONECT   24   18                                                            
CONECT   25   18                                                            
CONECT   26   19                                                            
CONECT   27    2   13                                                       
CONECT   28   17   20                                                       
CONECT   29   19   20                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

COMPND    HMDB0060923
HETATM    1  C1  UNL     1       7.028  -0.780   1.944  1.00  0.00           C  
HETATM    2  O1  UNL     1       6.634  -1.719   0.990  1.00  0.00           O  
HETATM    3  C2  UNL     1       5.465  -1.610   0.259  1.00  0.00           C  
HETATM    4  C3  UNL     1       5.168  -2.611  -0.671  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.997  -2.478  -1.386  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.129  -1.420  -1.221  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.963  -1.321  -1.957  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.093  -0.264  -1.795  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.183  -0.136  -2.587  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.116   1.120  -3.459  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.354  -0.115  -1.698  1.00  0.00           C  
HETATM   12  O2  UNL     1      -2.236  -1.000  -1.814  1.00  0.00           O  
HETATM   13  O3  UNL     1      -1.558   0.841  -0.713  1.00  0.00           O  
HETATM   14  C11 UNL     1      -2.648   0.893   0.141  1.00  0.00           C  
HETATM   15  O4  UNL     1      -2.326   0.821   1.489  1.00  0.00           O  
HETATM   16  C12 UNL     1      -3.442   0.353   2.159  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.295  -1.141   2.257  1.00  0.00           C  
HETATM   18  O5  UNL     1      -4.172  -1.844   2.823  1.00  0.00           O  
HETATM   19  O6  UNL     1      -2.197  -1.810   1.734  1.00  0.00           O  
HETATM   20  C14 UNL     1      -4.746   0.758   1.608  1.00  0.00           C  
HETATM   21  O7  UNL     1      -5.681   1.025   2.629  1.00  0.00           O  
HETATM   22  C15 UNL     1      -4.760   1.914   0.674  1.00  0.00           C  
HETATM   23  O8  UNL     1      -5.698   1.697  -0.364  1.00  0.00           O  
HETATM   24  C16 UNL     1      -3.448   2.195   0.006  1.00  0.00           C  
HETATM   25  O9  UNL     1      -2.798   3.194   0.740  1.00  0.00           O  
HETATM   26  C17 UNL     1       1.437   0.691  -0.864  1.00  0.00           C  
HETATM   27  C18 UNL     1       2.605   0.600  -0.121  1.00  0.00           C  
HETATM   28  C19 UNL     1       3.469  -0.461  -0.290  1.00  0.00           C  
HETATM   29  C20 UNL     1       4.634  -0.543   0.457  1.00  0.00           C  
HETATM   30  H1  UNL     1       6.210  -0.422   2.602  1.00  0.00           H  
HETATM   31  H2  UNL     1       7.517   0.120   1.495  1.00  0.00           H  
HETATM   32  H3  UNL     1       7.793  -1.210   2.651  1.00  0.00           H  
HETATM   33  H4  UNL     1       5.844  -3.454  -0.814  1.00  0.00           H  
HETATM   34  H5  UNL     1       3.750  -3.236  -2.107  1.00  0.00           H  
HETATM   35  H6  UNL     1       1.713  -2.085  -2.684  1.00  0.00           H  
HETATM   36  H7  UNL     1      -0.289  -0.988  -3.287  1.00  0.00           H  
HETATM   37  H8  UNL     1       0.945   1.397  -3.537  1.00  0.00           H  
HETATM   38  H9  UNL     1      -0.484   0.890  -4.478  1.00  0.00           H  
HETATM   39  H10 UNL     1      -0.691   1.946  -2.991  1.00  0.00           H  
HETATM   40  H11 UNL     1      -3.335   0.052  -0.083  1.00  0.00           H  
HETATM   41  H12 UNL     1      -3.360   0.721   3.210  1.00  0.00           H  
HETATM   42  H13 UNL     1      -2.325  -2.607   1.123  1.00  0.00           H  
HETATM   43  H14 UNL     1      -5.184  -0.125   1.054  1.00  0.00           H  
HETATM   44  H15 UNL     1      -5.761   0.201   3.152  1.00  0.00           H  
HETATM   45  H16 UNL     1      -5.096   2.856   1.164  1.00  0.00           H  
HETATM   46  H17 UNL     1      -5.698   0.729  -0.562  1.00  0.00           H  
HETATM   47  H18 UNL     1      -3.567   2.465  -1.054  1.00  0.00           H  
HETATM   48  H19 UNL     1      -2.474   2.813   1.585  1.00  0.00           H  
HETATM   49  H20 UNL     1       0.758   1.521  -0.734  1.00  0.00           H  
HETATM   50  H21 UNL     1       2.881   1.342   0.608  1.00  0.00           H  
HETATM   51  H22 UNL     1       4.890   0.225   1.190  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3
CONECT    3    4    4   29
CONECT    4    5   33
CONECT    5    6    6   34
CONECT    6    7   28
CONECT    7    8    8   35
CONECT    8    9   26
CONECT    9   10   11   36
CONECT   10   37   38   39
CONECT   11   12   12   13
CONECT   13   14
CONECT   14   15   24   40
CONECT   15   16
CONECT   16   17   20   41
CONECT   17   18   18   19
CONECT   19   42
CONECT   20   21   22   43
CONECT   21   44
CONECT   22   23   24   45
CONECT   23   46
CONECT   24   25   47
CONECT   25   48
CONECT   26   27   27   49
CONECT   27   28   50
CONECT   28   29   29
CONECT   29   51
END

HMDB0060923
     RDKit          3D
Naproxen O-glucuronide
 51 53  0  0  0  0  0  0  0  0999 V2000
    7.0283   -0.7796    1.9437 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6338   -1.7195    0.9898 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4649   -1.6102    0.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1681   -2.6110   -0.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9971   -2.4780   -1.3862 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1286   -1.4198   -1.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9633   -1.3208   -1.9571 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0930   -0.2643   -1.7952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1826   -0.1360   -2.5874 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1164    1.1202   -3.4588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3544   -0.1148   -1.6979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2360   -1.0002   -1.8139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5584    0.8415   -0.7132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6482    0.8925    0.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3261    0.8208    1.4885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4423    0.3525    2.1587 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2950   -1.1406    2.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1717   -1.8437    2.8235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1971   -1.8105    1.7340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7457    0.7578    1.6080 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6809    1.0245    2.6292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7601    1.9139    0.6744 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6977    1.6968   -0.3636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4481    2.1946    0.0063 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7976    3.1938    0.7403 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4374    0.6913   -0.8644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6049    0.5996   -0.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4691   -0.4608   -0.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6338   -0.5430    0.4568 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2099   -0.4224    2.6023 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5169    0.1204    1.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7933   -1.2103    2.6514 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8441   -3.4538   -0.8137 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7503   -3.2363   -2.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7133   -2.0850   -2.6842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2895   -0.9875   -3.2865 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9449    1.3970   -3.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4843    0.8905   -4.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6912    1.9459   -2.9908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3346    0.0521   -0.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3604    0.7208    3.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3249   -2.6065    1.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1844   -0.1252    1.0539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7608    0.2005    3.1516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0958    2.8560    1.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6981    0.7290   -0.5624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5674    2.4655   -1.0540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4743    2.8135    1.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7577    1.5214   -0.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8808    1.3425    0.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8904    0.2246    1.1904 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
  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 28  1  0
 28 29  2  0
 29  3  1  0
 28  6  1  0
 24 14  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  5 34  1  0
  7 35  1  0
  9 36  1  6
 10 37  1  0
 10 38  1  0
 10 39  1  0
 14 40  1  0
 16 41  1  1
 19 42  1  0
 20 43  1  6
 21 44  1  0
 22 45  1  1
 23 46  1  0
 24 47  1  6
 25 48  1  0
 26 49  1  0
 27 50  1  0
 29 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₀H₂₂O₉

Average Molecular Weight

406.3833

Monoisotopic Molecular Weight

406.126382302

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C=C(C=CC2=C1)[C@H](C)C(=O)OC1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C20H22O9/c1-9(10-3-4-12-8-13(27-2)6-5-11(12)7-10)19(26)29-20-16(23)14(21)15(22)17(28-20)18(24)25/h3-9,14-17,20-23H,1-2H3,(H,24,25)/t9-,14-,15-,16+,17-,20?/m0/s1

InChI Key

XRHIELLXTVJOKM-WDZACEAPSA-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
Naphthalene
Anisole
Alkyl aryl ether
Beta-hydroxy acid
Dicarboxylic acid or derivatives
Hydroxy acid
Monosaccharide
Benzenoid
Oxane
Pyran
Carboxylic acid ester
Secondary alcohol
Ether
Acetal
Carboxylic acid
Carboxylic acid derivative
Organoheterocyclic compound
Polyol
Oxacycle
Organic oxide
Alcohol
Carbonyl group
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060923)

Organ

Kidney (HMDB: HMDB0060923)
Liver (HMDB: HMDB0060923)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060923)

Cellular substructure

Cytoplasm (HMDB: HMDB0060923)

Source

Endogenous

Endogenous (HMDB: HMDB0060923)

Process

Not Available

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	0.9 g/L	ALOGPS
logP	0.84	ALOGPS
logP	1.04	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	3.44	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	142.75 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	97.15 m³·mol⁻¹	ChemAxon
Polarizability	40.48 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	195.049	31661259
DarkChem	[M-H]-	194.221	31661259
DeepCCS	[M+H]+	185.018	30932474
DeepCCS	[M-H]-	182.622	30932474
DeepCCS	[M-2H]-	215.69	30932474
DeepCCS	[M+Na]+	191.574	30932474
AllCCS	[M+H]+	197.1	32859911
AllCCS	[M+H-H2O]+	194.5	32859911
AllCCS	[M+NH4]+	199.5	32859911
AllCCS	[M+Na]+	200.2	32859911
AllCCS	[M-H]-	192.4	32859911
AllCCS	[M+Na-2H]-	192.8	32859911
AllCCS	[M+HCOO]-	193.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Naproxen O-glucuronide	COC1=CC=C2C=C(C=CC2=C1)[C@H](C)C(=O)OC1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O	4692.1	Standard polar	33892256
Naproxen O-glucuronide	COC1=CC=C2C=C(C=CC2=C1)[C@H](C)C(=O)OC1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O	3247.1	Standard non polar	33892256
Naproxen O-glucuronide	COC1=CC=C2C=C(C=CC2=C1)[C@H](C)C(=O)OC1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O	3502.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Naproxen O-glucuronide,1TMS,isomer #1	COC1=CC=C2C=C([C@H](C)C(=O)OC3O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]3O)C=CC2=C1	3289.1	Semi standard non polar	33892256
Naproxen O-glucuronide,1TMS,isomer #2	COC1=CC=C2C=C([C@H](C)C(=O)OC3O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]3O)C=CC2=C1	3301.0	Semi standard non polar	33892256
Naproxen O-glucuronide,1TMS,isomer #3	COC1=CC=C2C=C([C@H](C)C(=O)OC3O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]3O[Si](C)(C)C)C=CC2=C1	3316.0	Semi standard non polar	33892256
Naproxen O-glucuronide,1TMS,isomer #4	COC1=CC=C2C=C([C@H](C)C(=O)OC3O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]3O)C=CC2=C1	3257.8	Semi standard non polar	33892256
Naproxen O-glucuronide,2TMS,isomer #1	COC1=CC=C2C=C([C@H](C)C(=O)OC3O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]3O)C=CC2=C1	3228.0	Semi standard non polar	33892256
Naproxen O-glucuronide,2TMS,isomer #2	COC1=CC=C2C=C([C@H](C)C(=O)OC3O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]3O)C=CC2=C1	3255.2	Semi standard non polar	33892256
Naproxen O-glucuronide,2TMS,isomer #3	COC1=CC=C2C=C([C@H](C)C(=O)OC3O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]3O[Si](C)(C)C)C=CC2=C1	3277.9	Semi standard non polar	33892256
Naproxen O-glucuronide,2TMS,isomer #4	COC1=CC=C2C=C([C@H](C)C(=O)OC3O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]3O)C=CC2=C1	3236.4	Semi standard non polar	33892256
Naproxen O-glucuronide,2TMS,isomer #5	COC1=CC=C2C=C([C@H](C)C(=O)OC3O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]3O[Si](C)(C)C)C=CC2=C1	3276.2	Semi standard non polar	33892256
Naproxen O-glucuronide,2TMS,isomer #6	COC1=CC=C2C=C([C@H](C)C(=O)OC3O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]3O[Si](C)(C)C)C=CC2=C1	3228.2	Semi standard non polar	33892256
Naproxen O-glucuronide,3TMS,isomer #1	COC1=CC=C2C=C([C@H](C)C(=O)OC3O[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]3O)C=CC2=C1	3269.4	Semi standard non polar	33892256
Naproxen O-glucuronide,3TMS,isomer #2	COC1=CC=C2C=C([C@H](C)C(=O)OC3O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]3O[Si](C)(C)C)C=CC2=C1	3282.8	Semi standard non polar	33892256
Naproxen O-glucuronide,3TMS,isomer #3	COC1=CC=C2C=C([C@H](C)C(=O)OC3O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]3O[Si](C)(C)C)C=CC2=C1	3275.9	Semi standard non polar	33892256
Naproxen O-glucuronide,3TMS,isomer #4	COC1=CC=C2C=C([C@H](C)C(=O)OC3O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]3O[Si](C)(C)C)C=CC2=C1	3264.9	Semi standard non polar	33892256
Naproxen O-glucuronide,4TMS,isomer #1	COC1=CC=C2C=C([C@H](C)C(=O)OC3O[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]3O[Si](C)(C)C)C=CC2=C1	3323.7	Semi standard non polar	33892256
Naproxen O-glucuronide,1TBDMS,isomer #1	COC1=CC=C2C=C([C@H](C)C(=O)OC3O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]3O)C=CC2=C1	3569.4	Semi standard non polar	33892256
Naproxen O-glucuronide,1TBDMS,isomer #2	COC1=CC=C2C=C([C@H](C)C(=O)OC3O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]3O)C=CC2=C1	3596.1	Semi standard non polar	33892256
Naproxen O-glucuronide,1TBDMS,isomer #3	COC1=CC=C2C=C([C@H](C)C(=O)OC3O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]3O[Si](C)(C)C(C)(C)C)C=CC2=C1	3602.5	Semi standard non polar	33892256
Naproxen O-glucuronide,1TBDMS,isomer #4	COC1=CC=C2C=C([C@H](C)C(=O)OC3O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]3O)C=CC2=C1	3556.2	Semi standard non polar	33892256
Naproxen O-glucuronide,2TBDMS,isomer #1	COC1=CC=C2C=C([C@H](C)C(=O)OC3O[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]3O)C=CC2=C1	3779.8	Semi standard non polar	33892256
Naproxen O-glucuronide,2TBDMS,isomer #2	COC1=CC=C2C=C([C@H](C)C(=O)OC3O[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]3O)C=CC2=C1	3777.7	Semi standard non polar	33892256
Naproxen O-glucuronide,2TBDMS,isomer #3	COC1=CC=C2C=C([C@H](C)C(=O)OC3O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]3O[Si](C)(C)C(C)(C)C)C=CC2=C1	3800.8	Semi standard non polar	33892256
Naproxen O-glucuronide,2TBDMS,isomer #4	COC1=CC=C2C=C([C@H](C)C(=O)OC3O[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]3O)C=CC2=C1	3777.8	Semi standard non polar	33892256
Naproxen O-glucuronide,2TBDMS,isomer #5	COC1=CC=C2C=C([C@H](C)C(=O)OC3O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]3O[Si](C)(C)C(C)(C)C)C=CC2=C1	3799.0	Semi standard non polar	33892256
Naproxen O-glucuronide,2TBDMS,isomer #6	COC1=CC=C2C=C([C@H](C)C(=O)OC3O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]3O[Si](C)(C)C(C)(C)C)C=CC2=C1	3782.0	Semi standard non polar	33892256
Naproxen O-glucuronide,3TBDMS,isomer #1	COC1=CC=C2C=C([C@H](C)C(=O)OC3O[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]3O)C=CC2=C1	3957.2	Semi standard non polar	33892256
Naproxen O-glucuronide,3TBDMS,isomer #2	COC1=CC=C2C=C([C@H](C)C(=O)OC3O[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]3O[Si](C)(C)C(C)(C)C)C=CC2=C1	3991.4	Semi standard non polar	33892256
Naproxen O-glucuronide,3TBDMS,isomer #3	COC1=CC=C2C=C([C@H](C)C(=O)OC3O[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]3O[Si](C)(C)C(C)(C)C)C=CC2=C1	3951.2	Semi standard non polar	33892256
Naproxen O-glucuronide,3TBDMS,isomer #4	COC1=CC=C2C=C([C@H](C)C(=O)OC3O[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]3O[Si](C)(C)C(C)(C)C)C=CC2=C1	3952.7	Semi standard non polar	33892256
Naproxen O-glucuronide,4TBDMS,isomer #1	COC1=CC=C2C=C([C@H](C)C(=O)OC3O[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]3O[Si](C)(C)C(C)(C)C)C=CC2=C1	4143.8	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 - Naproxen O-glucuronide GC-MS (Non-derivatized) - 70eV, Positive	splash10-052r-9713000000-cf3ebdba5fe932e7aff9	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naproxen O-glucuronide GC-MS (4 TMS) - 70eV, Positive	splash10-005i-3621119000-6d026138e3771cc5bcfb	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naproxen O-glucuronide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naproxen O-glucuronide 10V, Positive-QTOF	splash10-06sr-0492100000-fd65711e4008d1736cf5	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naproxen O-glucuronide 20V, Positive-QTOF	splash10-08gi-0791000000-769169a96916d3dad3d3	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naproxen O-glucuronide 40V, Positive-QTOF	splash10-08gr-1930000000-99f2960fcd430ce9f89d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naproxen O-glucuronide 10V, Negative-QTOF	splash10-06vi-1293400000-9ce8a1a3c979690e8e39	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naproxen O-glucuronide 20V, Negative-QTOF	splash10-01t9-4893000000-6ec9b06cd3e973d924db	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naproxen O-glucuronide 40V, Negative-QTOF	splash10-06vl-9860000000-058f3a2d1cda97ad0cd1	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naproxen O-glucuronide 10V, Positive-QTOF	splash10-06ri-0961600000-6f563c4dbdf9e2a69f4f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naproxen O-glucuronide 20V, Positive-QTOF	splash10-000i-0910000000-734cbc7037a0b7d16575	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naproxen O-glucuronide 40V, Positive-QTOF	splash10-0540-0930000000-4ac14837d813a0b441b1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naproxen O-glucuronide 10V, Negative-QTOF	splash10-0a6r-0940500000-f50c01f1a4f0e171ceb2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naproxen O-glucuronide 20V, Negative-QTOF	splash10-0aor-2921000000-07a2b354d5c94fd3c303	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naproxen O-glucuronide 40V, Negative-QTOF	splash10-07vi-5940100000-f1400518c21630cd576b	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54484412

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)

Not Available

General References

Not Available

Showing metabocard for Naproxen O-glucuronide (HMDB0060923)

MOL for HMDB0060923 (Naproxen O-glucuronide)

3D MOL for HMDB0060923 (Naproxen O-glucuronide)

3D SDF for HMDB0060923 (Naproxen O-glucuronide)

3D-SDF for HMDB0060923 (Naproxen O-glucuronide)

PDB for HMDB0060923 (Naproxen O-glucuronide)

3D PDB for HMDB0060923 (Naproxen O-glucuronide)

SMILES for HMDB0060923 (Naproxen O-glucuronide)

INCHI for HMDB0060923 (Naproxen O-glucuronide)

Structure for HMDB0060923 (Naproxen O-glucuronide)

3D Structure for HMDB0060923 (Naproxen O-glucuronide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra