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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-15 17:14:09 UTC

Update Date

2019-07-23 07:14:39 UTC

HMDB ID

HMDB0060590

Secondary Accession Numbers

HMDB60590

Metabolite Identification

Common Name

Roflumilast N-oxide

Description

Roflumilast N-oxide belongs to the class of organic compounds known as benzamides. These are organic compounds containing a carboxamido substituent attached to a benzene ring. Roflumilast N-oxide is an extremely weak basic (essentially neutral) compound (based on its pKa). Roflumilast N-oxide is a metabolite of roflumilast. It has antiinflammatory effects and is under development as an orally administered drug for the treatment of inflammatory conditions of the lungs such as asthma, and chronic obstructive pulmonary disease (COPD). Roflumilast (trade names Daxas, Daliresp) is a drug which acts as a selective, long-acting inhibitor of the enzyme PDE-4.

Structure

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


  Mrv0541 06151310142D          

 27 29  0  0  0  0            999 V2000
    1.0164    8.1395    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.3020    7.7270    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.3020    6.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    6.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    5.6645    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    6.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414    6.4895    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414    5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    5.2520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559    5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559    4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2704    4.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2704    3.1895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559    2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559    1.9520    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
   -2.9684    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849    4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6993    4.0145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6993    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849    2.7770    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4138    2.7770    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849    5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2704    5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    7.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414    8.1395    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    8.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 17  1  0  0  0  0
 12 18  2  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
 20 22  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  2  0  0  0  0
 10 24  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
  2 27  1  0  0  0  0
M  CHG  2   1  -1   2   1
M  END

HMDB0060590
     RDKit          3D
Roflumilast N-oxide
 41 43  0  0  0  0  0  0  0  0999 V2000
    1.7143   -0.9485    1.3492 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8525   -0.1410    0.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1447    0.1890   -0.0909 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3249   -0.3802    0.4929 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9793    0.2197    1.5462 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3893    1.7203    2.2233 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.1231   -0.3360    2.1088 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6272   -1.4927    1.6301 N   0  0  0  0  0  4  0  0  0  0  0  0
    7.7537   -2.0410    2.1834 O   0  0  0  0  0  1  0  0  0  0  0  0
    5.9981   -2.1049    0.5893 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8644   -1.5572    0.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0928   -2.3805   -1.3051 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.6707    0.4425   -0.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7037    1.3250   -1.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4515    1.8841   -1.8236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6823    1.5552   -1.3481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8200    2.0883   -1.8926 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9760    2.9854   -2.9357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6436    4.1418   -2.5626 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6725    2.4408   -4.0119 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7398    0.6544   -0.2853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0140    0.3385    0.1779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1944   -0.5718    1.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6797   -0.7027    1.5220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5683   -1.2093    0.4211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2735   -2.0719    1.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6045    0.1157    0.2659 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3329    0.8459   -0.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6484    0.1225    2.9359 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3722   -3.0413    0.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6598    1.6149   -1.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3026    2.5725   -2.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9939    3.2747   -3.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7304   -0.1048    2.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7019   -1.5332    1.0804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1549    0.0787    2.1528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5913   -0.7927    0.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0280   -1.3735   -0.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6302   -2.9511    1.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1309   -2.2854    2.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6679   -0.5903    1.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
  2 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 16 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 21 27  2  0
 11  4  1  0
 27 13  1  0
 26 24  1  0
  3 28  1  0
  7 29  1  0
 10 30  1  0
 14 31  1  0
 15 32  1  0
 18 33  1  0
 23 34  1  0
 23 35  1  0
 24 36  1  0
 25 37  1  0
 25 38  1  0
 26 39  1  0
 26 40  1  0
 27 41  1  0
M  CHG  2   8   1   9  -1
M  END


  Mrv0541 06151310142D          

 27 29  0  0  0  0            999 V2000
    1.0164    8.1395    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.3020    7.7270    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.3020    6.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    6.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    5.6645    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    6.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414    6.4895    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414    5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    5.2520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559    5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559    4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2704    4.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2704    3.1895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559    2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559    1.9520    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
   -2.9684    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849    4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6993    4.0145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6993    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849    2.7770    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4138    2.7770    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849    5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2704    5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    7.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414    8.1395    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    8.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 17  1  0  0  0  0
 12 18  2  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
 20 22  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  2  0  0  0  0
 10 24  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
  2 27  1  0  0  0  0
M  CHG  2   1  -1   2   1
M  END
> <DATABASE_ID>
HMDB0060590

> <DATABASE_NAME>
hmdb

> <SMILES>
[O-][N+]1=CC(Cl)=C(NC(=O)C2=CC(OCC3CC3)=C(OC(F)F)C=C2)C(Cl)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H14Cl2F2N2O4/c18-11-6-23(25)7-12(19)15(11)22-16(24)10-3-4-13(27-17(20)21)14(5-10)26-8-9-1-2-9/h3-7,9,17H,1-2,8H2,(H,22,24)

> <INCHI_KEY>
PCGSQNPMMSALEJ-UHFFFAOYSA-N

> <FORMULA>
C17H14Cl2F2N2O4

> <MOLECULAR_WEIGHT>
419.207

> <EXACT_MASS>
418.02986877

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
36.16614724004185

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5-dichloro-4-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzamido]pyridin-1-ium-1-olate

> <ALOGPS_LOGP>
4.17

> <JCHEM_LOGP>
3.1873836053333333

> <ALOGPS_LOGS>
-5.28

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.261439787737131

> <JCHEM_PKA_STRONGEST_BASIC>
-0.32029914933471104

> <JCHEM_POLAR_SURFACE_AREA>
73.02000000000001

> <JCHEM_REFRACTIVITY>
97.61100000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.20e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,5-dichloro-4-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzamido]pyridin-1-ium-1-olate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060590
     RDKit          3D
Roflumilast N-oxide
 41 43  0  0  0  0  0  0  0  0999 V2000
    1.7143   -0.9485    1.3492 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8525   -0.1410    0.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1447    0.1890   -0.0909 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3249   -0.3802    0.4929 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9793    0.2197    1.5462 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3893    1.7203    2.2233 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.1231   -0.3360    2.1088 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6272   -1.4927    1.6301 N   0  0  0  0  0  4  0  0  0  0  0  0
    7.7537   -2.0410    2.1834 O   0  0  0  0  0  1  0  0  0  0  0  0
    5.9981   -2.1049    0.5893 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8644   -1.5572    0.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0928   -2.3805   -1.3051 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.6707    0.4425   -0.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7037    1.3250   -1.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4515    1.8841   -1.8236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6823    1.5552   -1.3481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8200    2.0883   -1.8926 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9760    2.9854   -2.9357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6436    4.1418   -2.5626 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6725    2.4408   -4.0119 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7398    0.6544   -0.2853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0140    0.3385    0.1779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1944   -0.5718    1.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6797   -0.7027    1.5220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5683   -1.2093    0.4211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2735   -2.0719    1.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6045    0.1157    0.2659 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3329    0.8459   -0.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6484    0.1225    2.9359 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3722   -3.0413    0.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6598    1.6149   -1.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3026    2.5725   -2.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9939    3.2747   -3.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7304   -0.1048    2.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7019   -1.5332    1.0804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1549    0.0787    2.1528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5913   -0.7927    0.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0280   -1.3735   -0.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6302   -2.9511    1.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1309   -2.2854    2.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6679   -0.5903    1.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
  2 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 16 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 21 27  2  0
 11  4  1  0
 27 13  1  0
 26 24  1  0
  3 28  1  0
  7 29  1  0
 10 30  1  0
 14 31  1  0
 15 32  1  0
 18 33  1  0
 23 34  1  0
 23 35  1  0
 24 36  1  0
 25 37  1  0
 25 38  1  0
 26 39  1  0
 26 40  1  0
 27 41  1  0
M  CHG  2   8   1   9  -1
M  END

HEADER    PROTEIN                                 15-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-JUN-13         0                                  
HETATM    1  O   UNK     0       1.897  15.194   0.000  0.00  0.00           O-1
HETATM    2  N   UNK     0       0.564  14.424   0.000  0.00  0.00           N+1
HETATM    3  C   UNK     0       0.564  12.884   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.770  12.114   0.000  0.00  0.00           C+0
HETATM    5 Cl   UNK     0      -0.770  10.574   0.000  0.00  0.00          Cl+0
HETATM    6  C   UNK     0      -2.104  12.884   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -3.437  12.114   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -3.437  10.574   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.104   9.804   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -4.771   9.804   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.771   8.264   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.105   7.494   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -6.105   5.954   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -4.771   5.184   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.771   3.644   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.541   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -7.438   8.264   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -8.772   7.494   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -8.772   5.954   0.000  0.00  0.00           C+0
HETATM   21  F   UNK     0      -7.438   5.184   0.000  0.00  0.00           F+0
HETATM   22  F   UNK     0     -10.106   5.184   0.000  0.00  0.00           F+0
HETATM   23  C   UNK     0      -7.438   9.804   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.105  10.574   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.104  14.424   0.000  0.00  0.00           C+0
HETATM   26 Cl   UNK     0      -3.437  15.194   0.000  0.00  0.00          Cl+0
HETATM   27  C   UNK     0      -0.770  15.194   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   27                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   25                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   24                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15   17                                                       
CONECT   17   16   15                                                       
CONECT   18   12   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   18   24                                                       
CONECT   24   23   10                                                       
CONECT   25    6   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25    2                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

COMPND    HMDB0060590
HETATM    1  O1  UNL     1       1.714  -0.949   1.349  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.853  -0.141   0.390  1.00  0.00           C  
HETATM    3  N1  UNL     1       3.145   0.189  -0.091  1.00  0.00           N  
HETATM    4  C2  UNL     1       4.325  -0.380   0.493  1.00  0.00           C  
HETATM    5  C3  UNL     1       4.979   0.220   1.546  1.00  0.00           C  
HETATM    6 CL1  UNL     1       4.389   1.720   2.223  1.00  0.00          CL  
HETATM    7  C4  UNL     1       6.123  -0.336   2.109  1.00  0.00           C  
HETATM    8  N2  UNL     1       6.627  -1.493   1.630  1.00  0.00           N1+
HETATM    9  O2  UNL     1       7.754  -2.041   2.183  1.00  0.00           O1-
HETATM   10  C5  UNL     1       5.998  -2.105   0.589  1.00  0.00           C  
HETATM   11  C6  UNL     1       4.864  -1.557   0.029  1.00  0.00           C  
HETATM   12 CL2  UNL     1       4.093  -2.380  -1.305  1.00  0.00          CL  
HETATM   13  C7  UNL     1       0.671   0.442  -0.210  1.00  0.00           C  
HETATM   14  C8  UNL     1       0.704   1.325  -1.250  1.00  0.00           C  
HETATM   15  C9  UNL     1      -0.451   1.884  -1.824  1.00  0.00           C  
HETATM   16  C10 UNL     1      -1.682   1.555  -1.348  1.00  0.00           C  
HETATM   17  O3  UNL     1      -2.820   2.088  -1.893  1.00  0.00           O  
HETATM   18  C11 UNL     1      -2.976   2.985  -2.936  1.00  0.00           C  
HETATM   19  F1  UNL     1      -3.644   4.142  -2.563  1.00  0.00           F  
HETATM   20  F2  UNL     1      -3.672   2.441  -4.012  1.00  0.00           F  
HETATM   21  C12 UNL     1      -1.740   0.654  -0.285  1.00  0.00           C  
HETATM   22  O4  UNL     1      -3.014   0.339   0.178  1.00  0.00           O  
HETATM   23  C13 UNL     1      -3.194  -0.572   1.261  1.00  0.00           C  
HETATM   24  C14 UNL     1      -4.680  -0.703   1.522  1.00  0.00           C  
HETATM   25  C15 UNL     1      -5.568  -1.209   0.421  1.00  0.00           C  
HETATM   26  C16 UNL     1      -5.274  -2.072   1.598  1.00  0.00           C  
HETATM   27  C17 UNL     1      -0.604   0.116   0.266  1.00  0.00           C  
HETATM   28  H1  UNL     1       3.333   0.846  -0.877  1.00  0.00           H  
HETATM   29  H2  UNL     1       6.648   0.122   2.936  1.00  0.00           H  
HETATM   30  H3  UNL     1       6.372  -3.041   0.172  1.00  0.00           H  
HETATM   31  H4  UNL     1       1.660   1.615  -1.660  1.00  0.00           H  
HETATM   32  H5  UNL     1      -0.303   2.572  -2.643  1.00  0.00           H  
HETATM   33  H6  UNL     1      -1.994   3.275  -3.347  1.00  0.00           H  
HETATM   34  H7  UNL     1      -2.730  -0.105   2.155  1.00  0.00           H  
HETATM   35  H8  UNL     1      -2.702  -1.533   1.080  1.00  0.00           H  
HETATM   36  H9  UNL     1      -5.155   0.079   2.153  1.00  0.00           H  
HETATM   37  H10 UNL     1      -6.591  -0.793   0.295  1.00  0.00           H  
HETATM   38  H11 UNL     1      -5.028  -1.373  -0.542  1.00  0.00           H  
HETATM   39  H12 UNL     1      -4.630  -2.951   1.398  1.00  0.00           H  
HETATM   40  H13 UNL     1      -6.131  -2.285   2.267  1.00  0.00           H  
HETATM   41  H14 UNL     1      -0.668  -0.590   1.100  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
CONECT    3    4   28
CONECT    4    5    5   11
CONECT    5    6    7
CONECT    7    8    8   29
CONECT    8    9   10
CONECT   10   11   11   30
CONECT   11   12
CONECT   13   14   14   27
CONECT   14   15   31
CONECT   15   16   16   32
CONECT   16   17   21
CONECT   17   18
CONECT   18   19   20   33
CONECT   21   22   27   27
CONECT   22   23
CONECT   23   24   34   35
CONECT   24   25   26   36
CONECT   25   26   37   38
CONECT   26   39   40
CONECT   27   41
END

HMDB0060590
     RDKit          3D
Roflumilast N-oxide
 41 43  0  0  0  0  0  0  0  0999 V2000
    1.7143   -0.9485    1.3492 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8525   -0.1410    0.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1447    0.1890   -0.0909 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3249   -0.3802    0.4929 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9793    0.2197    1.5462 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3893    1.7203    2.2233 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.1231   -0.3360    2.1088 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6272   -1.4927    1.6301 N   0  0  0  0  0  4  0  0  0  0  0  0
    7.7537   -2.0410    2.1834 O   0  0  0  0  0  1  0  0  0  0  0  0
    5.9981   -2.1049    0.5893 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8644   -1.5572    0.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0928   -2.3805   -1.3051 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.6707    0.4425   -0.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7037    1.3250   -1.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4515    1.8841   -1.8236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6823    1.5552   -1.3481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8200    2.0883   -1.8926 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9760    2.9854   -2.9357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6436    4.1418   -2.5626 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6725    2.4408   -4.0119 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7398    0.6544   -0.2853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0140    0.3385    0.1779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1944   -0.5718    1.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6797   -0.7027    1.5220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5683   -1.2093    0.4211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2735   -2.0719    1.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6045    0.1157    0.2659 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3329    0.8459   -0.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6484    0.1225    2.9359 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3722   -3.0413    0.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6598    1.6149   -1.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3026    2.5725   -2.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9939    3.2747   -3.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7304   -0.1048    2.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7019   -1.5332    1.0804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1549    0.0787    2.1528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5913   -0.7927    0.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0280   -1.3735   -0.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6302   -2.9511    1.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1309   -2.2854    2.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6679   -0.5903    1.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
  2 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 16 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 21 27  2  0
 11  4  1  0
 27 13  1  0
 26 24  1  0
  3 28  1  0
  7 29  1  0
 10 30  1  0
 14 31  1  0
 15 32  1  0
 18 33  1  0
 23 34  1  0
 23 35  1  0
 24 36  1  0
 25 37  1  0
 25 38  1  0
 26 39  1  0
 26 40  1  0
 27 41  1  0
M  CHG  2   8   1   9  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₇H₁₄Cl₂F₂N₂O₄

Average Molecular Weight

419.207

Monoisotopic Molecular Weight

418.02986877

IUPAC Name

3,5-dichloro-4-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzamido]pyridin-1-ium-1-olate

Traditional Name

3,5-dichloro-4-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzamido]pyridin-1-ium-1-olate

CAS Registry Number

Not Available

SMILES

[O-][N+]1=CC(Cl)=C(NC(=O)C2=CC(OCC3CC3)=C(OC(F)F)C=C2)C(Cl)=C1

InChI Identifier

InChI=1S/C17H14Cl2F2N2O4/c18-11-6-23(25)7-12(19)15(11)22-16(24)10-3-4-13(27-17(20)21)14(5-10)26-8-9-1-2-9/h3-7,9,17H,1-2,8H2,(H,22,24)

InChI Key

PCGSQNPMMSALEJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzamides. These are organic compounds containing a carboxamido substituent attached to a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzamides

Alternative Parents

Substituents

Benzamide
Phenoxy compound
Benzoyl
Polyhalopyridine
Phenol ether
Alkyl aryl ether
Aryl chloride
Aryl halide
Pyridinium
Pyridine
Heteroaromatic compound
Carboxamide group
Secondary carboxylic acid amide
Azacycle
Carboxylic acid derivative
Ether
Organoheterocyclic compound
Organochloride
Organohalogen compound
Alkyl halide
Alkyl fluoride
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organofluoride
Organonitrogen compound
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060590)
Liver (HMDB: HMDB0060590)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060590)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060590)

Cellular substructure

Cytoplasm (HMDB: HMDB0060590)
Membrane (HMDB: HMDB0060590)

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	0.0022 g/L	ALOGPS
logP	4.17	ALOGPS
logP	3.19	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	7.26	ChemAxon
pKa (Strongest Basic)	-0.32	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	73.02 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	97.61 m³·mol⁻¹	ChemAxon
Polarizability	36.17 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	191.681	30932474
DeepCCS	[M-H]-	189.323	30932474
DeepCCS	[M-2H]-	222.384	30932474
DeepCCS	[M+Na]+	197.774	30932474
AllCCS	[M+H]+	187.0	32859911
AllCCS	[M+H-H2O]+	184.5	32859911
AllCCS	[M+NH4]+	189.3	32859911
AllCCS	[M+Na]+	190.0	32859911
AllCCS	[M-H]-	181.2	32859911
AllCCS	[M+Na-2H]-	180.6	32859911
AllCCS	[M+HCOO]-	180.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Roflumilast N-oxide	[O-][N+]1=CC(Cl)=C(NC(=O)C2=CC(OCC3CC3)=C(OC(F)F)C=C2)C(Cl)=C1	4042.8	Standard polar	33892256
Roflumilast N-oxide	[O-][N+]1=CC(Cl)=C(NC(=O)C2=CC(OCC3CC3)=C(OC(F)F)C=C2)C(Cl)=C1	2960.1	Standard non polar	33892256
Roflumilast N-oxide	[O-][N+]1=CC(Cl)=C(NC(=O)C2=CC(OCC3CC3)=C(OC(F)F)C=C2)C(Cl)=C1	3351.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Roflumilast N-oxide,1TMS,isomer #1	C[Si](C)(C)N(C(=O)C1=CC=C(OC(F)F)C(OCC2CC2)=C1)C1=C(Cl)C=[N+]([O-])C=C1Cl	2809.8	Semi standard non polar	33892256
Roflumilast N-oxide,1TMS,isomer #1	C[Si](C)(C)N(C(=O)C1=CC=C(OC(F)F)C(OCC2CC2)=C1)C1=C(Cl)C=[N+]([O-])C=C1Cl	2750.9	Standard non polar	33892256
Roflumilast N-oxide,1TMS,isomer #1	C[Si](C)(C)N(C(=O)C1=CC=C(OC(F)F)C(OCC2CC2)=C1)C1=C(Cl)C=[N+]([O-])C=C1Cl	3369.3	Standard polar	33892256
Roflumilast N-oxide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C1=CC=C(OC(F)F)C(OCC2CC2)=C1)C1=C(Cl)C=[N+]([O-])C=C1Cl	3082.7	Semi standard non polar	33892256
Roflumilast N-oxide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C1=CC=C(OC(F)F)C(OCC2CC2)=C1)C1=C(Cl)C=[N+]([O-])C=C1Cl	2956.8	Standard non polar	33892256
Roflumilast N-oxide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C1=CC=C(OC(F)F)C(OCC2CC2)=C1)C1=C(Cl)C=[N+]([O-])C=C1Cl	3429.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Roflumilast N-oxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6x-9525100000-026a4326d0cbbb7299dc	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Roflumilast N-oxide 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 - Roflumilast N-oxide 10V, Positive-QTOF	splash10-066r-4033900000-87938499d786f4c329c1	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Roflumilast N-oxide 20V, Positive-QTOF	splash10-0a4l-8395300000-616f098e64736a3e577c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Roflumilast N-oxide 40V, Positive-QTOF	splash10-0a4i-9500000000-b3366d2b2654dc1e8c2a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Roflumilast N-oxide 10V, Negative-QTOF	splash10-014i-0007900000-82c7a6a7e99aec6ee1d9	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Roflumilast N-oxide 20V, Negative-QTOF	splash10-03xr-2219300000-da706abf30181119f4a5	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Roflumilast N-oxide 40V, Negative-QTOF	splash10-004i-4934000000-afc412786cbcb3201d30	2017-10-06	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

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

Not Available

Showing metabocard for Roflumilast N-oxide (HMDB0060590)

MOL for HMDB0060590 (Roflumilast N-oxide)

3D MOL for HMDB0060590 (Roflumilast N-oxide)

3D SDF for HMDB0060590 (Roflumilast N-oxide)

3D-SDF for HMDB0060590 (Roflumilast N-oxide)

PDB for HMDB0060590 (Roflumilast N-oxide)

3D PDB for HMDB0060590 (Roflumilast N-oxide)

SMILES for HMDB0060590 (Roflumilast N-oxide)

INCHI for HMDB0060590 (Roflumilast N-oxide)

Structure for HMDB0060590 (Roflumilast N-oxide)

3D Structure for HMDB0060590 (Roflumilast N-oxide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra