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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (7)transporters (2) Show 9 proteins XML

enzymes (7)transporters (2) Show 9 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:00:44 UTC

Update Date

2021-09-14 15:00:47 UTC

HMDB ID

HMDB0013989

Secondary Accession Numbers

HMDB13989

Metabolite Identification

Common Name

O-Desmethylnaproxen

Description

O-Desmethylnaproxen belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position. O-Desmethylnaproxen is an extremely weak basic (essentially neutral) compound (based on its pKa). O-Desmethylnaproxen is only found in individuals that have used or taken Naproxen.

Structure

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

HMDB0013989
     RDKit          3D
O-Desmethylnaproxen
 28 29  0  0  0  0  0  0  0  0999 V2000
   -3.2769    0.8491   -0.5369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5031   -0.3899   -0.0997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1071   -0.8330    1.1771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3646   -0.9090    2.1814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4497   -1.1475    1.2353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0611   -0.0985    0.0301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6925    0.8794    0.9311 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6483    1.1755    1.0760 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6092    0.5138    0.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9593    0.7951    0.4702 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9198    0.1330   -0.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2899    0.4190   -0.1335 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5293   -0.8410   -1.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1893   -1.1406   -1.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2434   -0.4701   -0.5666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0955   -0.7657   -0.7113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1361    0.4995   -1.1396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6101    1.5348   -1.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6005    1.3840    0.3794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6178   -1.1927   -0.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9361   -1.6607    0.4929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4497    1.4159    1.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9269    1.9445    1.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2403    1.5602    1.1759 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5921    1.1315    0.5195 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2854   -1.3574   -1.7354 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9122   -1.8938   -2.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4444   -1.5353   -1.4142 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
  3  5  1  0
  2  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16  6  1  0
 15  9  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  5 21  1  0
  7 22  1  0
  8 23  1  0
 10 24  1  0
 12 25  1  0
 13 26  1  0
 14 27  1  0
 16 28  1  0
M  END


  Mrv0541 09071314342D          

 16 17  0  0  0  0            999 V2000
   13.5998   -7.7449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3156   -6.0949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6011   -7.3324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8867   -6.0949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1722   -6.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7433   -6.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7433   -7.3324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4577   -6.0949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1722   -7.3324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4577   -7.7449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8867   -5.2699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0288   -6.0949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0288   -7.7449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3143   -7.3324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6011   -6.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3143   -6.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  2 15  1  0  0  0  0
  3 15  2  0  0  0  0
  4  5  1  0  0  0  0
  4 11  1  0  0  0  0
  4 15  1  0  0  0  0
  5  8  2  0  0  0  0
  5  9  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  6 12  1  0  0  0  0
  7 10  1  0  0  0  0
  7 13  1  0  0  0  0
  9 10  2  0  0  0  0
 12 16  2  0  0  0  0
 13 14  2  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013989

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C(O)=O)C1=CC2=C(C=C1)C=C(O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C13H12O3/c1-8(13(15)16)9-2-3-11-7-12(14)5-4-10(11)6-9/h2-8,14H,1H3,(H,15,16)

> <INCHI_KEY>
XWJUDDGELKXYNO-UHFFFAOYSA-N

> <FORMULA>
C13H12O3

> <MOLECULAR_WEIGHT>
216.2326

> <EXACT_MASS>
216.07864425

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
22.67718509836941

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.71

> <JCHEM_LOGP>
2.8398918186666666

> <ALOGPS_LOGS>
-3.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.782805110708352

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.339719503612902

> <JCHEM_PKA_STRONGEST_BASIC>
-5.496894643896106

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
60.371200000000016

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.78e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(6-hydroxynaphthalen-2-yl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013989
     RDKit          3D
O-Desmethylnaproxen
 28 29  0  0  0  0  0  0  0  0999 V2000
   -3.2769    0.8491   -0.5369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5031   -0.3899   -0.0997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1071   -0.8330    1.1771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3646   -0.9090    2.1814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4497   -1.1475    1.2353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0611   -0.0985    0.0301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6925    0.8794    0.9311 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6483    1.1755    1.0760 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6092    0.5138    0.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9593    0.7951    0.4702 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9198    0.1330   -0.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2899    0.4190   -0.1335 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5293   -0.8410   -1.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1893   -1.1406   -1.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2434   -0.4701   -0.5666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0955   -0.7657   -0.7113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1361    0.4995   -1.1396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6101    1.5348   -1.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6005    1.3840    0.3794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6178   -1.1927   -0.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9361   -1.6607    0.4929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4497    1.4159    1.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9269    1.9445    1.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2403    1.5602    1.1759 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5921    1.1315    0.5195 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2854   -1.3574   -1.7354 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9122   -1.8938   -2.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4444   -1.5353   -1.4142 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
  3  5  1  0
  2  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16  6  1  0
 15  9  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  5 21  1  0
  7 22  1  0
  8 23  1  0
 10 24  1  0
 12 25  1  0
 13 26  1  0
 14 27  1  0
 16 28  1  0
M  END

HEADER    PROTEIN                                 07-SEP-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-13         0                                  
HETATM    1  O   UNK     0      25.386 -14.457   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      36.056 -11.377   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      34.722 -13.687   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      33.389 -11.377   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      32.055 -12.147   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      29.387 -12.147   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      29.387 -13.687   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      30.721 -11.377   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      32.055 -13.687   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      30.721 -14.457   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      33.389  -9.837   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      28.054 -11.377   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      28.054 -14.457   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      26.720 -13.687   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      34.722 -12.147   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      26.720 -12.147   0.000  0.00  0.00           C+0
CONECT    1   14                                                            
CONECT    2   15                                                            
CONECT    3   15                                                            
CONECT    4    5   11   15                                                  
CONECT    5    4    8    9                                                  
CONECT    6    7    8   12                                                  
CONECT    7    6   10   13                                                  
CONECT    8    5    6                                                       
CONECT    9    5   10                                                       
CONECT   10    7    9                                                       
CONECT   11    4                                                            
CONECT   12    6   16                                                       
CONECT   13    7   14                                                       
CONECT   14    1   13   16                                                  
CONECT   15    2    3    4                                                  
CONECT   16   12   14                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0013989
HETATM    1  C1  UNL     1      -3.277   0.849  -0.537  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.503  -0.390  -0.100  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.107  -0.833   1.177  1.00  0.00           C  
HETATM    4  O1  UNL     1      -2.365  -0.909   2.181  1.00  0.00           O  
HETATM    5  O2  UNL     1      -4.450  -1.148   1.235  1.00  0.00           O  
HETATM    6  C4  UNL     1      -1.061  -0.099   0.030  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.692   0.879   0.931  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.648   1.175   1.076  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.609   0.514   0.340  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.959   0.795   0.470  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.920   0.133  -0.266  1.00  0.00           C  
HETATM   12  O3  UNL     1       5.290   0.419  -0.133  1.00  0.00           O  
HETATM   13  C10 UNL     1       3.529  -0.841  -1.161  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.189  -1.141  -1.309  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.243  -0.470  -0.567  1.00  0.00           C  
HETATM   16  C13 UNL     1      -0.096  -0.766  -0.711  1.00  0.00           C  
HETATM   17  H1  UNL     1      -4.136   0.499  -1.140  1.00  0.00           H  
HETATM   18  H2  UNL     1      -2.610   1.535  -1.108  1.00  0.00           H  
HETATM   19  H3  UNL     1      -3.600   1.384   0.379  1.00  0.00           H  
HETATM   20  H4  UNL     1      -2.618  -1.193  -0.859  1.00  0.00           H  
HETATM   21  H5  UNL     1      -4.936  -1.661   0.493  1.00  0.00           H  
HETATM   22  H6  UNL     1      -1.450   1.416   1.525  1.00  0.00           H  
HETATM   23  H7  UNL     1       0.927   1.944   1.786  1.00  0.00           H  
HETATM   24  H8  UNL     1       3.240   1.560   1.176  1.00  0.00           H  
HETATM   25  H9  UNL     1       5.592   1.131   0.519  1.00  0.00           H  
HETATM   26  H10 UNL     1       4.285  -1.357  -1.735  1.00  0.00           H  
HETATM   27  H11 UNL     1       1.912  -1.894  -2.004  1.00  0.00           H  
HETATM   28  H12 UNL     1      -0.444  -1.535  -1.414  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    6   20
CONECT    3    4    4    5
CONECT    5   21
CONECT    6    7    7   16
CONECT    7    8   22
CONECT    8    9    9   23
CONECT    9   10   15
CONECT   10   11   11   24
CONECT   11   12   13
CONECT   12   25
CONECT   13   14   14   26
CONECT   14   15   27
CONECT   15   16   16
CONECT   16   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Desmethylnaproxen, (S)-isomer	HMDB
Desmethylnaproxen	HMDB
Desmethylnaproxen, (+-)-isomer	HMDB
6-Desmethylnaproxen	HMDB
2-(6-Hydroxynaphthalen-2-yl)propanoate	Generator
6-O-Demethylnaproxen	MeSH

Chemical Formula

C₁₃H₁₂O₃

Average Molecular Weight

216.2326

Monoisotopic Molecular Weight

216.07864425

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(C(O)=O)C1=CC2=C(C=C1)C=C(O)C=C2

InChI Identifier

InChI=1S/C13H12O3/c1-8(13(15)16)9-2-3-11-7-12(14)5-4-10(11)6-9/h2-8,14H,1H3,(H,15,16)

InChI Key

XWJUDDGELKXYNO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Naphthols and derivatives

Direct Parent

Naphthols and derivatives

Alternative Parents

Substituents

2-naphthol
1-hydroxy-2-unsubstituted benzenoid
Monocarboxylic acid or derivatives
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: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0013989)

Organ

Liver (HMDB: HMDB0013989)
Kidney (HMDB: HMDB0013989)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Source

Endogenous

Endogenous (HMDB: HMDB0013989)

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	0.058 g/L	ALOGPS
logP	2.71	ALOGPS
logP	2.84	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	4.34	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	60.37 m³·mol⁻¹	ChemAxon
Polarizability	22.68 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
DarkChem	[M+H]+	151.703	31661259
DarkChem	[M-H]-	147.452	31661259
DeepCCS	[M+H]+	151.286	30932474
DeepCCS	[M-H]-	148.89	30932474
DeepCCS	[M-2H]-	181.9	30932474
DeepCCS	[M+Na]+	157.282	30932474
AllCCS	[M+H]+	147.5	32859911
AllCCS	[M+H-H2O]+	143.4	32859911
AllCCS	[M+NH4]+	151.4	32859911
AllCCS	[M+Na]+	152.5	32859911
AllCCS	[M-H]-	150.1	32859911
AllCCS	[M+Na-2H]-	150.0	32859911
AllCCS	[M+HCOO]-	150.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.4 minutes	32390414
Predicted by Siyang on May 30, 2022	12.0772 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.14 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	33.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1505.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	335.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	153.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	190.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	142.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	564.2 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	485.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	119.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	737.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	436.4 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	1376.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	307.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	348.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	460.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	267.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	72.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
O-Desmethylnaproxen	CC(C(O)=O)C1=CC2=C(C=C1)C=C(O)C=C2	3995.2	Standard polar	33892256
O-Desmethylnaproxen	CC(C(O)=O)C1=CC2=C(C=C1)C=C(O)C=C2	1950.9	Standard non polar	33892256
O-Desmethylnaproxen	CC(C(O)=O)C1=CC2=C(C=C1)C=C(O)C=C2	2220.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
O-Desmethylnaproxen,1TMS,isomer #1	CC(C(=O)O[Si](C)(C)C)C1=CC=C2C=C(O)C=CC2=C1	2174.1	Semi standard non polar	33892256
O-Desmethylnaproxen,1TMS,isomer #2	CC(C(=O)O)C1=CC=C2C=C(O[Si](C)(C)C)C=CC2=C1	2130.1	Semi standard non polar	33892256
O-Desmethylnaproxen,2TMS,isomer #1	CC(C(=O)O[Si](C)(C)C)C1=CC=C2C=C(O[Si](C)(C)C)C=CC2=C1	2125.6	Semi standard non polar	33892256
O-Desmethylnaproxen,1TBDMS,isomer #1	CC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=C2C=C(O)C=CC2=C1	2454.7	Semi standard non polar	33892256
O-Desmethylnaproxen,1TBDMS,isomer #2	CC(C(=O)O)C1=CC=C2C=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1	2418.9	Semi standard non polar	33892256
O-Desmethylnaproxen,2TBDMS,isomer #1	CC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=C2C=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1	2645.8	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 - O-Desmethylnaproxen GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-1910000000-9b71675e07edc0490fe6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Desmethylnaproxen GC-MS (2 TMS) - 70eV, Positive	splash10-00g0-9172000000-ae73c33511c6f4da61f1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Desmethylnaproxen 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 - O-Desmethylnaproxen 10V, Positive-QTOF	splash10-014i-0890000000-dfb443bf49038f199387	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylnaproxen 20V, Positive-QTOF	splash10-00xs-0910000000-0d3c6c99f73d48a4f355	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylnaproxen 40V, Positive-QTOF	splash10-0fft-0900000000-7a47fc9cb1387dd044da	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylnaproxen 10V, Negative-QTOF	splash10-014i-0490000000-7d6218f8744daf19d167	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylnaproxen 20V, Negative-QTOF	splash10-00xr-0940000000-f3b962ae4a733880c005	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylnaproxen 40V, Negative-QTOF	splash10-006x-2900000000-7d28fd097aa9fa24f860	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylnaproxen 10V, Positive-QTOF	splash10-014i-0790000000-28221e5ff8d5e48b4951	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylnaproxen 20V, Positive-QTOF	splash10-00di-0900000000-8f1b3ebca1242812a616	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylnaproxen 40V, Positive-QTOF	splash10-0uxr-0900000000-ca9cb92a9c096dc8793e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylnaproxen 10V, Negative-QTOF	splash10-00xr-0960000000-45e36ed050134c08d482	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylnaproxen 20V, Negative-QTOF	splash10-00di-0920000000-8bd84881af44e2282ce6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylnaproxen 40V, Negative-QTOF	splash10-006x-0900000000-4b04b70fe8ad31e21c18	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Naproxen Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry	21059682	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

143026

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162920

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

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 2B7

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

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]

Enzyme Details

2. UDP-glucuronosyltransferase 1-1

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

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]

Enzyme Details

3. Prostaglandin G/H synthase 2

General function:: Involved in peroxidase activity
Specific function:: Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:: PTGS2
Uniprot ID:: P35354
Molecular weight:: 68995.625

References

Albertini R, Aimbire F, Villaverde AB, Silva JA Jr, Costa MS: COX-2 mRNA expression decreases in the subplantar muscle of rat paw subjected to carrageenan-induced inflammation after low level laser therapy. Inflamm Res. 2007 Jun;56(6):228-9. [PubMed:17607546 ]
Dhir A, Naidu PS, Kulkarni SK: Neuroprotective effect of nimesulide, a preferential COX-2 inhibitor, against pentylenetetrazol (PTZ)-induced chemical kindling and associated biochemical parameters in mice. Seizure. 2007 Dec;16(8):691-7. Epub 2007 Jul 2. [PubMed:17604186 ]
Kumar P, Padi SS, Naidu PS, Kumar A: Cyclooxygenase inhibition attenuates 3-nitropropionic acid-induced neurotoxicity in rats: possible antioxidant mechanisms. Fundam Clin Pharmacol. 2007 Jun;21(3):297-306. [PubMed:17521299 ]
White WB: Cardiovascular effects of the selective cyclooxygenase-2 inhibitors. Subcell Biochem. 2007;42:145-58. [PubMed:17612049 ]
Hassan-Alin M, Naesdal J, Nilsson-Pieschl C, Langstrom G, Andersson T: Lack of Pharmacokinetic Interaction between Esomeprazole and the Nonsteroidal Anti-Inflammatory Drugs Naproxen and Rofecoxib in Healthy Subjects. Clin Drug Investig. 2005;25(11):731-40. [PubMed:17532719 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

4. Prostaglandin G/H synthase 1

General function:: Involved in peroxidase activity
Specific function:: May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:: PTGS1
Uniprot ID:: P23219
Molecular weight:: 68685.82

References

James MJ, Cook-Johnson RJ, Cleland LG: Selective COX-2 inhibitors, eicosanoid synthesis and clinical outcomes: a case study of system failure. Lipids. 2007 Sep;42(9):779-85. Epub 2007 Jun 2. [PubMed:17541796 ]

Enzyme Details

5. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

6. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

7. Cytochrome P450 2C8

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Enzyme Details

1. Solute carrier organic anion transporter family member 1A2

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids
Gene Name:: SLCO1A2
Uniprot ID:: P46721
Molecular weight:: 74144.1

References

Shitara Y, Sugiyama D, Kusuhara H, Kato Y, Abe T, Meier PJ, Itoh T, Sugiyama Y: Comparative inhibitory effects of different compounds on rat oatpl (slc21a1)- and Oatp2 (Slc21a5)-mediated transport. Pharm Res. 2002 Feb;19(2):147-53. [PubMed:11883641 ]

Enzyme Details

2. Solute carrier family 22 member 6

General function:: Involved in ion transmembrane transporter activity
Specific function:: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:: SLC22A6
Uniprot ID:: Q4U2R8
Molecular weight:: 61815.8

References

Mulato AS, Ho ES, Cihlar T: Nonsteroidal anti-inflammatory drugs efficiently reduce the transport and cytotoxicity of adefovir mediated by the human renal organic anion transporter 1. J Pharmacol Exp Ther. 2000 Oct;295(1):10-5. [PubMed:10991954 ]
Apiwattanakul N, Sekine T, Chairoungdua A, Kanai Y, Nakajima N, Sophasan S, Endou H: Transport properties of nonsteroidal anti-inflammatory drugs by organic anion transporter 1 expressed in Xenopus laevis oocytes. Mol Pharmacol. 1999 May;55(5):847-54. [PubMed:10220563 ]

Showing metabocard for O-Desmethylnaproxen (HMDB0013989)

MOL for HMDB0013989 (O-Desmethylnaproxen)

3D MOL for HMDB0013989 (O-Desmethylnaproxen)

3D SDF for HMDB0013989 (O-Desmethylnaproxen)

3D-SDF for HMDB0013989 (O-Desmethylnaproxen)

PDB for HMDB0013989 (O-Desmethylnaproxen)

3D PDB for HMDB0013989 (O-Desmethylnaproxen)

SMILES for HMDB0013989 (O-Desmethylnaproxen)

INCHI for HMDB0013989 (O-Desmethylnaproxen)

Structure for HMDB0013989 (O-Desmethylnaproxen)

3D Structure for HMDB0013989 (O-Desmethylnaproxen)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

References

Transporters

References

References