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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 15:05:47 UTC

Update Date

2021-09-26 23:10:16 UTC

HMDB ID

HMDB0255456

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Naproxcinod

Description

Naproxcinod, also known as NO-naproxen or nicox, 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 significant number of articles have been published on Naproxcinod. This compound has been identified in human blood as reported by (PMID: 31557052 ). Naproxcinod is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Naproxcinod 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

HMDB0255456
     RDKit          3D
Naproxcinod
 46 47  0  0  0  0  0  0  0  0999 V2000
   -7.8890    0.8950    0.1362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9155   -0.1215    0.0851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5799    0.2320    0.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1938    1.5455    0.4057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8666    1.9076    0.5434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8921    0.9197    0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5580    1.2503    0.6301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5449    0.3086    0.5906 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8757    0.7174    0.7405 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4868    0.0803    1.9674 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6646    0.3861   -0.4968 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2466    1.3143   -1.1540 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7911   -0.8960   -0.9631 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4898   -1.3085   -2.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9370   -1.4629   -2.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8792   -0.4193   -1.6464 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0089   -0.0367   -0.2276 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9742    1.0142   -0.0882 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2915    1.5592    1.1148 N   0  0  0  0  0  4  0  0  0  0  0  0
    7.4673    1.7898    1.4213 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3051    1.8614    2.0079 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.9056   -1.0100    0.4085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2407   -1.3679    0.2707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2411   -0.4123    0.3127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5677   -0.7074    0.1831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6128    1.6796   -0.5928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8958    1.4098    1.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9021    0.5109   -0.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9292    2.3517    0.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5853    2.9422    0.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3400    2.3149    0.7720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9191    1.8084    0.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9393    0.8533    2.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7230   -0.4706    2.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3277   -0.5823    1.6690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0219   -2.2767   -2.4937 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1905   -0.5964   -2.9395 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2341   -2.3991   -1.4199 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2654   -1.8848   -3.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9253   -0.7094   -2.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6915    0.5570   -2.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4240   -0.9526    0.3507 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1434    0.2390    0.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1605   -1.7958    0.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5497   -2.3901    0.1274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8525   -1.7534    0.0386 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  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
  8 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25  3  1  0
 24  6  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  7 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 10 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 22 44  1  0
 23 45  1  0
 25 46  1  0
M  CHG  2  19   1  21  -1
M  END


  Mrv1652309112117062D          

 25 26  0  0  0  0            999 V2000
    0.0000   -3.3000    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
   -0.7145   -2.0625    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
   -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
   -2.1434   -2.0625    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
   -2.8579   -0.8250    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
   -2.1434    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
   -3.5724    0.4125    0.0000 O   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
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   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  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -3.3000    0.0000 O   0  5  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
  3  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  5 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
M  CHG  2  23   1  25  -1
M  END
> <DATABASE_ID>
HMDB0255456

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C=C1)C=C(C=C2)C(C)C(=O)OCCCCO[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H21NO6/c1-13(18(20)24-9-3-4-10-25-19(21)22)14-5-6-16-12-17(23-2)8-7-15(16)11-14/h5-8,11-13H,3-4,9-10H2,1-2H3

> <INCHI_KEY>
AKFJWRDCWYYTIG-UHFFFAOYSA-N

> <FORMULA>
C18H21NO6

> <MOLECULAR_WEIGHT>
347.367

> <EXACT_MASS>
347.1368874

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
36.71973902779386

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(nitrooxy)butyl 2-(6-methoxynaphthalen-2-yl)propanoate

> <ALOGPS_LOGP>
3.79

> <JCHEM_LOGP>
3.7174149699999997

> <ALOGPS_LOGS>
-6.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.801915487543419

> <JCHEM_POLAR_SURFACE_AREA>
87.9

> <JCHEM_REFRACTIVITY>
91.11469999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.81e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(nitrooxy)butyl 2-(6-methoxynaphthalen-2-yl)propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0255456
     RDKit          3D
Naproxcinod
 46 47  0  0  0  0  0  0  0  0999 V2000
   -7.8890    0.8950    0.1362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9155   -0.1215    0.0851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5799    0.2320    0.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1938    1.5455    0.4057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8666    1.9076    0.5434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8921    0.9197    0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5580    1.2503    0.6301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5449    0.3086    0.5906 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8757    0.7174    0.7405 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4868    0.0803    1.9674 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6646    0.3861   -0.4968 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2466    1.3143   -1.1540 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7911   -0.8960   -0.9631 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4898   -1.3085   -2.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9370   -1.4629   -2.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8792   -0.4193   -1.6464 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0089   -0.0367   -0.2276 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9742    1.0142   -0.0882 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2915    1.5592    1.1148 N   0  0  0  0  0  4  0  0  0  0  0  0
    7.4673    1.7898    1.4213 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3051    1.8614    2.0079 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.9056   -1.0100    0.4085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2407   -1.3679    0.2707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2411   -0.4123    0.3127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5677   -0.7074    0.1831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6128    1.6796   -0.5928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8958    1.4098    1.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9021    0.5109   -0.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9292    2.3517    0.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5853    2.9422    0.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3400    2.3149    0.7720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9191    1.8084    0.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9393    0.8533    2.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7230   -0.4706    2.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3277   -0.5823    1.6690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0219   -2.2767   -2.4937 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1905   -0.5964   -2.9395 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2341   -2.3991   -1.4199 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2654   -1.8848   -3.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9253   -0.7094   -2.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6915    0.5570   -2.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4240   -0.9526    0.3507 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1434    0.2390    0.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1605   -1.7958    0.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5497   -2.3901    0.1274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8525   -1.7534    0.0386 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  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
  8 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25  3  1  0
 24  6  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  7 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 10 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 22 44  1  0
 23 45  1  0
 25 46  1  0
M  CHG  2  19   1  21  -1
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       0.000  -6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -4.620   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      -1.334  -2.310   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      -4.001  -3.850   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      -5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -6.668   0.770   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.336  -3.850   0.000  0.00  0.00           O+0
HETATM   23  N   UNK     0      10.669  -4.620   0.000  0.00  0.00           N+1
HETATM   24  O   UNK     0      12.003  -3.850   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      10.669  -6.160   0.000  0.00  0.00           O-1
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3                                                       
CONECT    9    6   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11    5                                                       
CONECT   13   10   14                                                       
CONECT   14   13                                                            
CONECT   15    2   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

COMPND    HMDB0255456
HETATM    1  C1  UNL     1      -7.889   0.895   0.136  1.00  0.00           C  
HETATM    2  O1  UNL     1      -6.916  -0.122   0.085  1.00  0.00           O  
HETATM    3  C2  UNL     1      -5.580   0.232   0.222  1.00  0.00           C  
HETATM    4  C3  UNL     1      -5.194   1.545   0.406  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.867   1.908   0.543  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.892   0.920   0.496  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.558   1.250   0.630  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.545   0.309   0.591  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.876   0.717   0.741  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.487   0.080   1.967  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.665   0.386  -0.497  1.00  0.00           C  
HETATM   12  O2  UNL     1       2.247   1.314  -1.154  1.00  0.00           O  
HETATM   13  O3  UNL     1       1.791  -0.896  -0.963  1.00  0.00           O  
HETATM   14  C11 UNL     1       2.490  -1.308  -2.054  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.937  -1.463  -2.040  1.00  0.00           C  
HETATM   16  C13 UNL     1       4.879  -0.419  -1.646  1.00  0.00           C  
HETATM   17  C14 UNL     1       5.009  -0.037  -0.228  1.00  0.00           C  
HETATM   18  O4  UNL     1       5.974   1.014  -0.088  1.00  0.00           O  
HETATM   19  N1  UNL     1       6.291   1.559   1.115  1.00  0.00           N1+
HETATM   20  O5  UNL     1       7.467   1.790   1.421  1.00  0.00           O  
HETATM   21  O6  UNL     1       5.305   1.861   2.008  1.00  0.00           O1-
HETATM   22  C15 UNL     1      -0.906  -1.010   0.408  1.00  0.00           C  
HETATM   23  C16 UNL     1      -2.241  -1.368   0.271  1.00  0.00           C  
HETATM   24  C17 UNL     1      -3.241  -0.412   0.313  1.00  0.00           C  
HETATM   25  C18 UNL     1      -4.568  -0.707   0.183  1.00  0.00           C  
HETATM   26  H1  UNL     1      -7.613   1.680  -0.593  1.00  0.00           H  
HETATM   27  H2  UNL     1      -7.896   1.410   1.135  1.00  0.00           H  
HETATM   28  H3  UNL     1      -8.902   0.511  -0.074  1.00  0.00           H  
HETATM   29  H4  UNL     1      -5.929   2.352   0.449  1.00  0.00           H  
HETATM   30  H5  UNL     1      -3.585   2.942   0.686  1.00  0.00           H  
HETATM   31  H6  UNL     1      -1.340   2.315   0.772  1.00  0.00           H  
HETATM   32  H7  UNL     1       0.919   1.808   0.873  1.00  0.00           H  
HETATM   33  H8  UNL     1       1.939   0.853   2.647  1.00  0.00           H  
HETATM   34  H9  UNL     1       0.723  -0.471   2.554  1.00  0.00           H  
HETATM   35  H10 UNL     1       2.328  -0.582   1.669  1.00  0.00           H  
HETATM   36  H11 UNL     1       2.022  -2.277  -2.494  1.00  0.00           H  
HETATM   37  H12 UNL     1       2.191  -0.596  -2.939  1.00  0.00           H  
HETATM   38  H13 UNL     1       4.234  -2.399  -1.420  1.00  0.00           H  
HETATM   39  H14 UNL     1       4.265  -1.885  -3.086  1.00  0.00           H  
HETATM   40  H15 UNL     1       5.925  -0.709  -2.030  1.00  0.00           H  
HETATM   41  H16 UNL     1       4.691   0.557  -2.231  1.00  0.00           H  
HETATM   42  H17 UNL     1       5.424  -0.953   0.351  1.00  0.00           H  
HETATM   43  H18 UNL     1       4.143   0.239   0.331  1.00  0.00           H  
HETATM   44  H19 UNL     1      -0.161  -1.796   0.368  1.00  0.00           H  
HETATM   45  H20 UNL     1      -2.550  -2.390   0.127  1.00  0.00           H  
HETATM   46  H21 UNL     1      -4.853  -1.753   0.039  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3
CONECT    3    4    4   25
CONECT    4    5   29
CONECT    5    6    6   30
CONECT    6    7   24
CONECT    7    8    8   31
CONECT    8    9   22
CONECT    9   10   11   32
CONECT   10   33   34   35
CONECT   11   12   12   13
CONECT   13   14
CONECT   14   15   36   37
CONECT   15   16   38   39
CONECT   16   17   40   41
CONECT   17   18   42   43
CONECT   18   19
CONECT   19   20   20   21
CONECT   22   23   23   44
CONECT   23   24   45
CONECT   24   25   25
CONECT   25   46
END

HMDB0255456
     RDKit          3D
Naproxcinod
 46 47  0  0  0  0  0  0  0  0999 V2000
   -7.8890    0.8950    0.1362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9155   -0.1215    0.0851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5799    0.2320    0.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1938    1.5455    0.4057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8666    1.9076    0.5434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8921    0.9197    0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5580    1.2503    0.6301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5449    0.3086    0.5906 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8757    0.7174    0.7405 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4868    0.0803    1.9674 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6646    0.3861   -0.4968 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2466    1.3143   -1.1540 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7911   -0.8960   -0.9631 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4898   -1.3085   -2.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9370   -1.4629   -2.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8792   -0.4193   -1.6464 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0089   -0.0367   -0.2276 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9742    1.0142   -0.0882 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2915    1.5592    1.1148 N   0  0  0  0  0  4  0  0  0  0  0  0
    7.4673    1.7898    1.4213 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3051    1.8614    2.0079 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.9056   -1.0100    0.4085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2407   -1.3679    0.2707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2411   -0.4123    0.3127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5677   -0.7074    0.1831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6128    1.6796   -0.5928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8958    1.4098    1.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9021    0.5109   -0.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9292    2.3517    0.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5853    2.9422    0.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3400    2.3149    0.7720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9191    1.8084    0.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9393    0.8533    2.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7230   -0.4706    2.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3277   -0.5823    1.6690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0219   -2.2767   -2.4937 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1905   -0.5964   -2.9395 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2341   -2.3991   -1.4199 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2654   -1.8848   -3.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9253   -0.7094   -2.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6915    0.5570   -2.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4240   -0.9526    0.3507 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1434    0.2390    0.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1605   -1.7958    0.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5497   -2.3901    0.1274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8525   -1.7534    0.0386 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  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
  8 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25  3  1  0
 24  6  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  7 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 10 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 22 44  1  0
 23 45  1  0
 25 46  1  0
M  CHG  2  19   1  21  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-(Nitrooxy)butyl-(2S)-2-(6-methoxy-2-naphthyl)propanoate	MeSH
Naproxen-N-butyl nitrate	MeSH
Nitric oxide-releasing naproxen	MeSH
Nitric oxide naproxen	MeSH
NO-Naproxen	MeSH
NicOx	MeSH

Chemical Formula

C₁₈H₂₁NO₆

Average Molecular Weight

347.367

Monoisotopic Molecular Weight

347.1368874

IUPAC Name

4-(nitrooxy)butyl 2-(6-methoxynaphthalen-2-yl)propanoate

Traditional Name

4-(nitrooxy)butyl 2-(6-methoxynaphthalen-2-yl)propanoate

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1)C=C(C=C2)C(C)C(=O)OCCCCO[N+]([O-])=O

InChI Identifier

InChI=1S/C18H21NO6/c1-13(18(20)24-9-3-4-10-25-19(21)22)14-5-6-16-12-17(23-2)8-7-15(16)11-14/h5-8,11-13H,3-4,9-10H2,1-2H3

InChI Key

AKFJWRDCWYYTIG-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
Organic nitrate
Alkyl nitrate
Carboxylic acid ester
Organic nitric acid or derivatives
Organic nitro compound
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Allyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Carbonyl group
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

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	3.79	ALOGPS
logP	3.72	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	87.9 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	91.11 m³·mol⁻¹	ChemAxon
Polarizability	36.72 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]+	177.498	30932474
DeepCCS	[M-H]-	175.14	30932474
DeepCCS	[M-2H]-	208.026	30932474
DeepCCS	[M+Na]+	183.591	30932474
AllCCS	[M+H]+	182.0	32859911
AllCCS	[M+H-H2O]+	179.2	32859911
AllCCS	[M+NH4]+	184.7	32859911
AllCCS	[M+Na]+	185.4	32859911
AllCCS	[M-H]-	184.4	32859911
AllCCS	[M+Na-2H]-	184.4	32859911
AllCCS	[M+HCOO]-	184.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Naproxcinod	COC1=CC2=C(C=C1)C=C(C=C2)C(C)C(=O)OCCCCO[N+]([O-])=O	3840.7	Standard polar	33892256
Naproxcinod	COC1=CC2=C(C=C1)C=C(C=C2)C(C)C(=O)OCCCCO[N+]([O-])=O	2633.9	Standard non polar	33892256
Naproxcinod	COC1=CC2=C(C=C1)C=C(C=C2)C(C)C(=O)OCCCCO[N+]([O-])=O	2746.7	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 - Naproxcinod GC-MS (Non-derivatized) - 70eV, Positive	splash10-05nr-3910000000-989fdf0a521591da0a1e	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naproxcinod GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	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

5293510

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Naproxcinod

METLIN ID

Not Available

PubChem Compound

6918304

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 Naproxcinod (HMDB0255456)

MOL for HMDB0255456 (Naproxcinod)

3D MOL for HMDB0255456 (Naproxcinod)

3D SDF for HMDB0255456 (Naproxcinod)

3D-SDF for HMDB0255456 (Naproxcinod)

PDB for HMDB0255456 (Naproxcinod)

3D PDB for HMDB0255456 (Naproxcinod)

SMILES for HMDB0255456 (Naproxcinod)

INCHI for HMDB0255456 (Naproxcinod)

Structure for HMDB0255456 (Naproxcinod)

3D Structure for HMDB0255456 (Naproxcinod)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra