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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 22:42:41 UTC

Update Date

2021-09-26 22:54:14 UTC

HMDB ID

HMDB0245654

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(R)-Naproxen

Description

2-(6-methoxynaphthalen-2-yl)propanoic acid belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. Based on a literature review a small amount of articles have been published on 2-(6-methoxynaphthalen-2-yl)propanoic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). (r)-naproxen is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (R)-Naproxen is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0245654
     RDKit          3D
(R)-Naproxen
 31 32  0  0  0  0  0  0  0  0999 V2000
    5.2307    0.2338    0.9918 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7276   -0.4295   -0.1525 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3528   -0.4606   -0.3459 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8391   -1.1040   -1.4586 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4565   -1.1385   -1.6584 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5810   -0.5561   -0.7897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7981   -0.6055   -1.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6733   -0.0134   -0.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1359   -0.0685   -0.3711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8286   -0.7636    0.7896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6529    1.3047   -0.5363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8621    2.2681   -0.4587 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0190    1.4870   -0.7758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1489    0.6167    0.9629 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2131    0.6797    1.2073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0896    0.0877    0.3231 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4523    0.1232    0.5224 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3021    0.0252    1.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6783   -0.1899    1.8716 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0419    1.3056    0.9742 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4900   -1.5825   -2.1793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0364   -1.6392   -2.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1679   -1.1148   -1.8906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3693   -0.6186   -1.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0104   -0.0047    1.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2369   -1.5917    1.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8208   -1.1424    0.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3517    1.9937   -1.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8601    1.0804    1.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5738    1.1911    2.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8708    0.6266    1.3947 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
  8 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17  3  1  0
 16  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  0
  7 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
 10 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
M  END


  Mrv1533004171517102D          

 17 18  0  0  0  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   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   -0.4125    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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  2  0  0  0  0
  3 12  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0245654

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C2C=C(C=CC2=C1)C(C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H14O3/c1-9(14(15)16)10-3-4-12-8-13(17-2)6-5-11(12)7-10/h3-9H,1-2H3,(H,15,16)

> <INCHI_KEY>
CMWTZPSULFXXJA-UHFFFAOYSA-N

> <FORMULA>
C14H14O3

> <MOLECULAR_WEIGHT>
230.263

> <EXACT_MASS>
230.094294311

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
24.778328322829125

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(6-methoxynaphthalen-2-yl)propanoic acid

> <ALOGPS_LOGP>
3.29

> <JCHEM_LOGP>
2.985785874666666

> <ALOGPS_LOGS>
-3.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.190353313973411

> <JCHEM_PKA_STRONGEST_BASIC>
-4.828411505428834

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
64.85350000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.11e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
naprosyn

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0245654
     RDKit          3D
(R)-Naproxen
 31 32  0  0  0  0  0  0  0  0999 V2000
    5.2307    0.2338    0.9918 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7276   -0.4295   -0.1525 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3528   -0.4606   -0.3459 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8391   -1.1040   -1.4586 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4565   -1.1385   -1.6584 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5810   -0.5561   -0.7897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7981   -0.6055   -1.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6733   -0.0134   -0.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1359   -0.0685   -0.3711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8286   -0.7636    0.7896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6529    1.3047   -0.5363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8621    2.2681   -0.4587 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0190    1.4870   -0.7758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1489    0.6167    0.9629 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2131    0.6797    1.2073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0896    0.0877    0.3231 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4523    0.1232    0.5224 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3021    0.0252    1.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6783   -0.1899    1.8716 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0419    1.3056    0.9742 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4900   -1.5825   -2.1793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0364   -1.6392   -2.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1679   -1.1148   -1.8906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3693   -0.6186   -1.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0104   -0.0047    1.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2369   -1.5917    1.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8208   -1.1424    0.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3517    1.9937   -1.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8601    1.0804    1.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5738    1.1911    2.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8708    0.6266    1.3947 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
  8 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17  3  1  0
 16  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  0
  7 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
 10 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
M  END

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.669  -0.000   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   12                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6   12                                                  
CONECT   12   11    3                                                       
CONECT   13    8   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0245654
HETATM    1  C1  UNL     1       5.231   0.234   0.992  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.728  -0.429  -0.153  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.353  -0.461  -0.346  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.839  -1.104  -1.459  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.456  -1.139  -1.658  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.581  -0.556  -0.790  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.798  -0.605  -1.014  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.673  -0.013  -0.129  1.00  0.00           C  
HETATM    9  C8  UNL     1      -3.136  -0.068  -0.371  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.829  -0.764   0.790  1.00  0.00           C  
HETATM   11  C10 UNL     1      -3.653   1.305  -0.536  1.00  0.00           C  
HETATM   12  O2  UNL     1      -2.862   2.268  -0.459  1.00  0.00           O  
HETATM   13  O3  UNL     1      -5.019   1.487  -0.776  1.00  0.00           O  
HETATM   14  C11 UNL     1      -1.149   0.617   0.963  1.00  0.00           C  
HETATM   15  C12 UNL     1       0.213   0.680   1.207  1.00  0.00           C  
HETATM   16  C13 UNL     1       1.090   0.088   0.323  1.00  0.00           C  
HETATM   17  C14 UNL     1       2.452   0.123   0.522  1.00  0.00           C  
HETATM   18  H1  UNL     1       6.302   0.025   1.161  1.00  0.00           H  
HETATM   19  H2  UNL     1       4.678  -0.190   1.872  1.00  0.00           H  
HETATM   20  H3  UNL     1       5.042   1.306   0.974  1.00  0.00           H  
HETATM   21  H4  UNL     1       3.490  -1.583  -2.179  1.00  0.00           H  
HETATM   22  H5  UNL     1       1.036  -1.639  -2.526  1.00  0.00           H  
HETATM   23  H6  UNL     1      -1.168  -1.115  -1.891  1.00  0.00           H  
HETATM   24  H7  UNL     1      -3.369  -0.619  -1.301  1.00  0.00           H  
HETATM   25  H8  UNL     1      -4.010  -0.005   1.591  1.00  0.00           H  
HETATM   26  H9  UNL     1      -3.237  -1.592   1.177  1.00  0.00           H  
HETATM   27  H10 UNL     1      -4.821  -1.142   0.461  1.00  0.00           H  
HETATM   28  H11 UNL     1      -5.352   1.994  -1.580  1.00  0.00           H  
HETATM   29  H12 UNL     1      -1.860   1.080   1.653  1.00  0.00           H  
HETATM   30  H13 UNL     1       0.574   1.191   2.087  1.00  0.00           H  
HETATM   31  H14 UNL     1       2.871   0.627   1.395  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3
CONECT    3    4    4   17
CONECT    4    5   21
CONECT    5    6    6   22
CONECT    6    7   16
CONECT    7    8    8   23
CONECT    8    9   14
CONECT    9   10   11   24
CONECT   10   25   26   27
CONECT   11   12   12   13
CONECT   13   28
CONECT   14   15   15   29
CONECT   15   16   30
CONECT   16   17   17
CONECT   17   31
END

HMDB0245654
     RDKit          3D
(R)-Naproxen
 31 32  0  0  0  0  0  0  0  0999 V2000
    5.2307    0.2338    0.9918 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7276   -0.4295   -0.1525 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3528   -0.4606   -0.3459 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8391   -1.1040   -1.4586 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4565   -1.1385   -1.6584 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5810   -0.5561   -0.7897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7981   -0.6055   -1.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6733   -0.0134   -0.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1359   -0.0685   -0.3711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8286   -0.7636    0.7896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6529    1.3047   -0.5363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8621    2.2681   -0.4587 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0190    1.4870   -0.7758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1489    0.6167    0.9629 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2131    0.6797    1.2073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0896    0.0877    0.3231 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4523    0.1232    0.5224 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3021    0.0252    1.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6783   -0.1899    1.8716 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0419    1.3056    0.9742 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4900   -1.5825   -2.1793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0364   -1.6392   -2.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1679   -1.1148   -1.8906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3693   -0.6186   -1.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0104   -0.0047    1.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2369   -1.5917    1.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8208   -1.1424    0.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3517    1.9937   -1.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8601    1.0804    1.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5738    1.1911    2.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8708    0.6266    1.3947 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
  8 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17  3  1  0
 16  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  0
  7 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
 10 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(6-Methoxynaphthalen-2-yl)propanoate	Generator

Chemical Formula

C₁₄H₁₄O₃

Average Molecular Weight

230.263

Monoisotopic Molecular Weight

230.094294311

IUPAC Name

2-(6-methoxynaphthalen-2-yl)propanoic acid

Traditional Name

naprosyn

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C=C(C=CC2=C1)C(C)C(O)=O

InChI Identifier

InChI=1S/C14H14O3/c1-9(14(15)16)10-3-4-12-8-13(17-2)6-5-11(12)7-10/h3-9H,1-2H3,(H,15,16)

InChI Key

CMWTZPSULFXXJA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Not Available

Direct Parent

Naphthalenes

Alternative Parents

Substituents

Naphthalene
Anisole
Alkyl aryl ether
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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
logP	3.29	ALOGPS
logP	2.99	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	4.19	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	64.85 m³·mol⁻¹	ChemAxon
Polarizability	24.78 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]+	151.839	30932474
DeepCCS	[M-H]-	149.481	30932474
DeepCCS	[M-2H]-	182.746	30932474
DeepCCS	[M+Na]+	157.933	30932474
AllCCS	[M+H]+	153.1	32859911
AllCCS	[M+H-H2O]+	149.3	32859911
AllCCS	[M+NH4]+	156.6	32859911
AllCCS	[M+Na]+	157.6	32859911
AllCCS	[M-H]-	156.1	32859911
AllCCS	[M+Na-2H]-	156.0	32859911
AllCCS	[M+HCOO]-	156.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	13.6573 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.07 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1784.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	406.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	184.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	219.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	107.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	613.9 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	656.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	112.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	936.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	548.5 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	1451.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	362.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	408.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	421.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	315.0 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	21.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(R)-Naproxen	COC1=CC=C2C=C(C=CC2=C1)C(C)C(O)=O	3671.0	Standard polar	33892256
(R)-Naproxen	COC1=CC=C2C=C(C=CC2=C1)C(C)C(O)=O	2000.9	Standard non polar	33892256
(R)-Naproxen	COC1=CC=C2C=C(C=CC2=C1)C(C)C(O)=O	2145.5	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 - (R)-Naproxen GC-MS (Non-derivatized) - 70eV, Positive	splash10-0019-0910000000-631a642d16ff24528dc1	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Naproxen GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Naproxen GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Naproxen GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Naproxen 90V, Positive-QTOF	splash10-0v4l-0900000000-7c3ec52c4ec57de8d04a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Naproxen 55V, Positive-QTOF	splash10-000i-0900000000-859217409a0e77896e90	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Naproxen 35V, Positive-QTOF	splash10-000i-0900000000-feef1dbdd596121834a0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Naproxen 30V, Positive-QTOF	splash10-000i-0900000000-242d308afe63e2491fb5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Naproxen 15V, Positive-QTOF	splash10-001r-0890000000-2132063ccbdfea9b53af	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Naproxen 80V, Positive-QTOF	splash10-0fk9-0900000000-8b5177ddbc0142164e2f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Naproxen 60V, Positive-QTOF	splash10-000i-0900000000-a4d84fe6d9919a3177aa	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Naproxen 75V, Positive-QTOF	splash10-0fki-0900000000-614c23cac777212edae0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Naproxen 35V, Positive-QTOF	splash10-000i-0900000000-4a20ba476cee17d7c1be	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Naproxen 75V, Positive-QTOF	splash10-0fki-0900000000-dd28182b88ffd934383a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Naproxen 60V, Positive-QTOF	splash10-000i-0900000000-1a4b555cc86ceec738c6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Naproxen 45V, Positive-QTOF	splash10-000i-0900000000-0efdb86c5956d7d207b9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Naproxen 30V, Positive-QTOF	splash10-000i-0900000000-bcc647c2703015bbdbb1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Naproxen 45V, Positive-QTOF	splash10-000i-0900000000-1de3e9a98bd725992f1c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Naproxen 50V, Positive-QTOF	splash10-0fr6-0900000000-30d5d1f1b34f0d286dea	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Naproxen 20V, Positive-QTOF	splash10-000i-0900000000-4ecf3c63ab05db8e0b52	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Naproxen 10V, Positive-QTOF	splash10-0019-0940000000-1eb69130990467962355	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Naproxen 30V, Positive-QTOF	splash10-0fe0-0900000000-5fd6b1971b0523a79260	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Naproxen 40V, Positive-QTOF	splash10-0ukc-0900000000-f6421e93ba111f02f3de	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Naproxen 15V, Positive-QTOF	splash10-001r-0790000000-10490b731c2c72b53099	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Naproxen 35V, Negative-QTOF	splash10-000i-0900000000-6c6f993054fa0e44d5a6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Naproxen 35V, Negative-QTOF	splash10-000i-0900000000-35388b797846ade97ee0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Naproxen 90V, Positive-QTOF	splash10-0v4l-0900000000-f6bf2c675f1ba47c4b5e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Naproxen 55V, Positive-QTOF	splash10-000i-0900000000-c2d0dabdf2c525935b95	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Naproxen 35V, Positive-QTOF	splash10-000i-0900000000-8487dbbcc0a131ca2038	2021-09-20	HMDB team, MONA	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	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

1262

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for (R)-Naproxen (HMDB0245654)

MOL for HMDB0245654 ((R)-Naproxen)

3D MOL for HMDB0245654 ((R)-Naproxen)

3D SDF for HMDB0245654 ((R)-Naproxen)

3D-SDF for HMDB0245654 ((R)-Naproxen)

PDB for HMDB0245654 ((R)-Naproxen)

3D PDB for HMDB0245654 ((R)-Naproxen)

SMILES for HMDB0245654 ((R)-Naproxen)

INCHI for HMDB0245654 ((R)-Naproxen)

Structure for HMDB0245654 ((R)-Naproxen)

3D Structure for HMDB0245654 ((R)-Naproxen)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra