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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 18:11:39 UTC

Update Date

2021-09-26 23:13:33 UTC

HMDB ID

HMDB0257288

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Roflumilast

Description

Roflumilast, also known as daliresp, belongs to the class of organic compounds known as benzamides. These are organic compounds containing a carboxamido substituent attached to a benzene ring. Based on a literature review a significant number of articles have been published on Roflumilast. This compound has been identified in human blood as reported by (PMID: 31557052 ). Roflumilast is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Roflumilast 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

1656
  Mrv0541 02231215372D          

 26 28  0  0  0  0            999 V2000
    7.4765    2.0625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.6185    2.0625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.7620   -2.4751    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.0475   -3.7126    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.9041   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3330   -2.4751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6185    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0475    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0475    3.7126    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6185   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3330   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6185   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3330    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0475   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0475   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3330    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0475    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0475   -2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7620    2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3330    2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7620    3.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3330    3.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 23  1  0  0  0  0
  2 24  1  0  0  0  0
  3 22  1  0  0  0  0
  4 22  1  0  0  0  0
  5 13  1  0  0  0  0
  5 14  1  0  0  0  0
  6 15  1  0  0  0  0
  6 22  1  0  0  0  0
  7 20  2  0  0  0  0
  8 20  1  0  0  0  0
  8 21  1  0  0  0  0
  9 25  2  0  0  0  0
  9 26  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
 11 12  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 15 18  1  0  0  0  0
 16 17  2  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 18 19  2  0  0  0  0
 21 23  2  0  0  0  0
 21 24  1  0  0  0  0
 23 25  1  0  0  0  0
 24 26  2  0  0  0  0
M  END

HMDB0257288
     RDKit          3D
Roflumilast
 40 42  0  0  0  0  0  0  0  0999 V2000
    3.2897    1.2308   -0.8871 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3573    0.4716   -0.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6831   -0.8109   -0.0107 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0732   -1.1635    0.0392 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6405   -1.7833   -1.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6312   -2.1078   -2.4493 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.9839   -2.1451   -1.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7326   -1.8775    0.0425 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2242   -1.2750    1.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8717   -0.9126    1.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1568   -0.1246    2.5236 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.9765    0.9686   -0.6229 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7560    2.2255   -1.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5483    2.6929   -1.2242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5997    1.8965   -0.8278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8791    2.3681   -0.9339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3175    3.5894   -1.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0346    4.2766   -0.4092 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2346    3.4356   -2.4568 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3741    0.6120   -0.3183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4715   -0.1152    0.0529 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4148   -1.4248    0.5840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7888   -1.9650    0.8976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5840   -1.1329    1.9313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0145   -1.2427    0.5347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0752    0.1730   -0.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9614   -1.5039    0.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3820   -2.6268   -1.9321 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8569   -1.0794    1.9890 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6054    2.8299   -1.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6627    3.7031   -1.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5604    4.3015   -1.7447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9130   -2.1370   -0.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8656   -1.3788    1.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8496   -3.0611    1.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1288   -0.1961    2.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1108   -1.7070    2.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9198   -0.3371   -0.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9206   -1.8394    0.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0856   -0.8275    0.1710 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
  9 10  2  0
 10 11  1  0
  2 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 15 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 20 26  2  0
 10  4  1  0
 26 12  1  0
 25 23  1  0
  3 27  1  0
  7 28  1  0
  9 29  1  0
 13 30  1  0
 14 31  1  0
 17 32  1  0
 22 33  1  0
 22 34  1  0
 23 35  1  0
 24 36  1  0
 24 37  1  0
 25 38  1  0
 25 39  1  0
 26 40  1  0
M  END

1656
  Mrv0541 02231215372D          

 26 28  0  0  0  0            999 V2000
    7.4765    2.0625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.6185    2.0625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.7620   -2.4751    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.0475   -3.7126    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.9041   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3330   -2.4751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6185    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0475    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0475    3.7126    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6185   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3330   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6185   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3330    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0475   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0475   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3330    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0475    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0475   -2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7620    2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3330    2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7620    3.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3330    3.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 23  1  0  0  0  0
  2 24  1  0  0  0  0
  3 22  1  0  0  0  0
  4 22  1  0  0  0  0
  5 13  1  0  0  0  0
  5 14  1  0  0  0  0
  6 15  1  0  0  0  0
  6 22  1  0  0  0  0
  7 20  2  0  0  0  0
  8 20  1  0  0  0  0
  8 21  1  0  0  0  0
  9 25  2  0  0  0  0
  9 26  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
 11 12  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 15 18  1  0  0  0  0
 16 17  2  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 18 19  2  0  0  0  0
 21 23  2  0  0  0  0
 21 24  1  0  0  0  0
 23 25  1  0  0  0  0
 24 26  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0257288

> <DATABASE_NAME>
hmdb

> <SMILES>
FC(F)OC1=C(OCC2CC2)C=C(C=C1)C(=O)NC1=C(Cl)C=NC=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C17H14Cl2F2N2O3/c18-11-6-22-7-12(19)15(11)23-16(24)10-3-4-13(26-17(20)21)14(5-10)25-8-9-1-2-9/h3-7,9,17H,1-2,8H2,(H,22,23,24)

> <INCHI_KEY>
MNDBXUUTURYVHR-UHFFFAOYSA-N

> <FORMULA>
C17H14Cl2F2N2O3

> <MOLECULAR_WEIGHT>
403.207

> <EXACT_MASS>
402.034954148

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
35.900799313481286

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(cyclopropylmethoxy)-N-(3,5-dichloropyridin-4-yl)-4-(difluoromethoxy)benzamide

> <ALOGPS_LOGP>
4.47

> <JCHEM_LOGP>
4.447540533

> <ALOGPS_LOGS>
-4.81

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.18230224536616

> <JCHEM_PKA_STRONGEST_BASIC>
2.3996089915454157

> <JCHEM_POLAR_SURFACE_AREA>
60.45

> <JCHEM_REFRACTIVITY>
93.92149999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.20e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
roflumilast

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0257288
     RDKit          3D
Roflumilast
 40 42  0  0  0  0  0  0  0  0999 V2000
    3.2897    1.2308   -0.8871 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3573    0.4716   -0.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6831   -0.8109   -0.0107 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0732   -1.1635    0.0392 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6405   -1.7833   -1.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6312   -2.1078   -2.4493 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.9839   -2.1451   -1.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7326   -1.8775    0.0425 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2242   -1.2750    1.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8717   -0.9126    1.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1568   -0.1246    2.5236 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.9765    0.9686   -0.6229 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7560    2.2255   -1.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5483    2.6929   -1.2242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5997    1.8965   -0.8278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8791    2.3681   -0.9339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3175    3.5894   -1.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0346    4.2766   -0.4092 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2346    3.4356   -2.4568 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3741    0.6120   -0.3183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4715   -0.1152    0.0529 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4148   -1.4248    0.5840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7888   -1.9650    0.8976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5840   -1.1329    1.9313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0145   -1.2427    0.5347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0752    0.1730   -0.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9614   -1.5039    0.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3820   -2.6268   -1.9321 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8569   -1.0794    1.9890 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6054    2.8299   -1.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6627    3.7031   -1.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5604    4.3015   -1.7447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9130   -2.1370   -0.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8656   -1.3788    1.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8496   -3.0611    1.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1288   -0.1961    2.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1108   -1.7070    2.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9198   -0.3371   -0.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9206   -1.8394    0.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0856   -0.8275    0.1710 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
  9 10  2  0
 10 11  1  0
  2 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 15 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 20 26  2  0
 10  4  1  0
 26 12  1  0
 25 23  1  0
  3 27  1  0
  7 28  1  0
  9 29  1  0
 13 30  1  0
 14 31  1  0
 17 32  1  0
 22 33  1  0
 22 34  1  0
 23 35  1  0
 24 36  1  0
 24 37  1  0
 25 38  1  0
 25 39  1  0
 26 40  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1656                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0      13.956   3.850   0.000  0.00  0.00          Cl+0
HETATM    2 Cl   UNK     0       8.621   3.850   0.000  0.00  0.00          Cl+0
HETATM    3  F   UNK     0      12.622  -4.620   0.000  0.00  0.00           F+0
HETATM    4  F   UNK     0      11.289  -6.930   0.000  0.00  0.00           F+0
HETATM    5  O   UNK     0       7.288  -3.080   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       9.955  -4.620   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       8.621   2.310   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      11.289   2.310   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      11.289   6.930   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       4.620  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.850  -4.414   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.080  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.954  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.621  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.955  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.621  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.955   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.289  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.289  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.955   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.289   3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.289  -5.390   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.622   4.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.955   4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.622   6.160   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.955   6.160   0.000  0.00  0.00           C+0
CONECT    1   23                                                            
CONECT    2   24                                                            
CONECT    3   22                                                            
CONECT    4   22                                                            
CONECT    5   13   14                                                       
CONECT    6   15   22                                                       
CONECT    7   20                                                            
CONECT    8   20   21                                                       
CONECT    9   25   26                                                       
CONECT   10   11   12   13                                                  
CONECT   11   10   12                                                       
CONECT   12   10   11                                                       
CONECT   13    5   10                                                       
CONECT   14    5   15   16                                                  
CONECT   15    6   14   18                                                  
CONECT   16   14   17                                                       
CONECT   17   16   19   20                                                  
CONECT   18   15   19                                                       
CONECT   19   17   18                                                       
CONECT   20    7    8   17                                                  
CONECT   21    8   23   24                                                  
CONECT   22    3    4    6                                                  
CONECT   23    1   21   25                                                  
CONECT   24    2   21   26                                                  
CONECT   25    9   23                                                       
CONECT   26    9   24                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

COMPND    HMDB0257288
HETATM    1  O1  UNL     1       3.290   1.231  -0.887  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.357   0.472  -0.513  1.00  0.00           C  
HETATM    3  N1  UNL     1       2.683  -0.811  -0.011  1.00  0.00           N  
HETATM    4  C2  UNL     1       4.073  -1.163   0.039  1.00  0.00           C  
HETATM    5  C3  UNL     1       4.641  -1.783  -1.054  1.00  0.00           C  
HETATM    6 CL1  UNL     1       3.631  -2.108  -2.449  1.00  0.00          CL  
HETATM    7  C4  UNL     1       5.984  -2.145  -1.055  1.00  0.00           C  
HETATM    8  N2  UNL     1       6.733  -1.878   0.042  1.00  0.00           N  
HETATM    9  C5  UNL     1       6.224  -1.275   1.133  1.00  0.00           C  
HETATM   10  C6  UNL     1       4.872  -0.913   1.129  1.00  0.00           C  
HETATM   11 CL2  UNL     1       4.157  -0.125   2.524  1.00  0.00          CL  
HETATM   12  C7  UNL     1       0.976   0.969  -0.623  1.00  0.00           C  
HETATM   13  C8  UNL     1       0.756   2.225  -1.121  1.00  0.00           C  
HETATM   14  C9  UNL     1      -0.548   2.693  -1.224  1.00  0.00           C  
HETATM   15  C10 UNL     1      -1.600   1.896  -0.828  1.00  0.00           C  
HETATM   16  O2  UNL     1      -2.879   2.368  -0.934  1.00  0.00           O  
HETATM   17  C11 UNL     1      -3.318   3.589  -1.403  1.00  0.00           C  
HETATM   18  F1  UNL     1      -4.035   4.277  -0.409  1.00  0.00           F  
HETATM   19  F2  UNL     1      -4.235   3.436  -2.457  1.00  0.00           F  
HETATM   20  C12 UNL     1      -1.374   0.612  -0.318  1.00  0.00           C  
HETATM   21  O3  UNL     1      -2.472  -0.115   0.053  1.00  0.00           O  
HETATM   22  C13 UNL     1      -2.415  -1.425   0.584  1.00  0.00           C  
HETATM   23  C14 UNL     1      -3.789  -1.965   0.898  1.00  0.00           C  
HETATM   24  C15 UNL     1      -4.584  -1.133   1.931  1.00  0.00           C  
HETATM   25  C16 UNL     1      -5.014  -1.243   0.535  1.00  0.00           C  
HETATM   26  C17 UNL     1      -0.075   0.173  -0.227  1.00  0.00           C  
HETATM   27  H1  UNL     1       1.961  -1.504   0.322  1.00  0.00           H  
HETATM   28  H2  UNL     1       6.382  -2.627  -1.932  1.00  0.00           H  
HETATM   29  H3  UNL     1       6.857  -1.079   1.989  1.00  0.00           H  
HETATM   30  H4  UNL     1       1.605   2.830  -1.426  1.00  0.00           H  
HETATM   31  H5  UNL     1      -0.663   3.703  -1.629  1.00  0.00           H  
HETATM   32  H6  UNL     1      -2.560   4.302  -1.745  1.00  0.00           H  
HETATM   33  H7  UNL     1      -1.913  -2.137  -0.087  1.00  0.00           H  
HETATM   34  H8  UNL     1      -1.866  -1.379   1.564  1.00  0.00           H  
HETATM   35  H9  UNL     1      -3.850  -3.061   1.041  1.00  0.00           H  
HETATM   36  H10 UNL     1      -4.129  -0.196   2.274  1.00  0.00           H  
HETATM   37  H11 UNL     1      -5.111  -1.707   2.713  1.00  0.00           H  
HETATM   38  H12 UNL     1      -4.920  -0.337  -0.104  1.00  0.00           H  
HETATM   39  H13 UNL     1      -5.921  -1.839   0.299  1.00  0.00           H  
HETATM   40  H14 UNL     1       0.086  -0.828   0.171  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   12
CONECT    3    4   27
CONECT    4    5    5   10
CONECT    5    6    7
CONECT    7    8    8   28
CONECT    8    9
CONECT    9   10   10   29
CONECT   10   11
CONECT   12   13   13   26
CONECT   13   14   30
CONECT   14   15   15   31
CONECT   15   16   20
CONECT   16   17
CONECT   17   18   19   32
CONECT   20   21   26   26
CONECT   21   22
CONECT   22   23   33   34
CONECT   23   24   25   35
CONECT   24   25   36   37
CONECT   25   38   39
CONECT   26   40
END

HMDB0257288
     RDKit          3D
Roflumilast
 40 42  0  0  0  0  0  0  0  0999 V2000
    3.2897    1.2308   -0.8871 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3573    0.4716   -0.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6831   -0.8109   -0.0107 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0732   -1.1635    0.0392 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6405   -1.7833   -1.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6312   -2.1078   -2.4493 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.9839   -2.1451   -1.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7326   -1.8775    0.0425 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2242   -1.2750    1.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8717   -0.9126    1.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1568   -0.1246    2.5236 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.9765    0.9686   -0.6229 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7560    2.2255   -1.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5483    2.6929   -1.2242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5997    1.8965   -0.8278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8791    2.3681   -0.9339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3175    3.5894   -1.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0346    4.2766   -0.4092 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2346    3.4356   -2.4568 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3741    0.6120   -0.3183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4715   -0.1152    0.0529 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4148   -1.4248    0.5840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7888   -1.9650    0.8976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5840   -1.1329    1.9313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0145   -1.2427    0.5347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0752    0.1730   -0.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9614   -1.5039    0.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3820   -2.6268   -1.9321 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8569   -1.0794    1.9890 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6054    2.8299   -1.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6627    3.7031   -1.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5604    4.3015   -1.7447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9130   -2.1370   -0.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8656   -1.3788    1.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8496   -3.0611    1.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1288   -0.1961    2.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1108   -1.7070    2.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9198   -0.3371   -0.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9206   -1.8394    0.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0856   -0.8275    0.1710 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
  9 10  2  0
 10 11  1  0
  2 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 15 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 20 26  2  0
 10  4  1  0
 26 12  1  0
 25 23  1  0
  3 27  1  0
  7 28  1  0
  9 29  1  0
 13 30  1  0
 14 31  1  0
 17 32  1  0
 22 33  1  0
 22 34  1  0
 23 35  1  0
 24 36  1  0
 24 37  1  0
 25 38  1  0
 25 39  1  0
 26 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Daliresp	ChEBI
Roflumilastum	ChEBI
3-Cyclopropylmethoxy-4-difluoromethoxy-N-(3,5-di-chloropyrid-4-yl)benzamide	MeSH

Chemical Formula

C₁₇H₁₄Cl₂F₂N₂O₃

Average Molecular Weight

403.207

Monoisotopic Molecular Weight

402.034954148

IUPAC Name

3-(cyclopropylmethoxy)-N-(3,5-dichloropyridin-4-yl)-4-(difluoromethoxy)benzamide

Traditional Name

roflumilast

CAS Registry Number

Not Available

SMILES

FC(F)OC1=C(OCC2CC2)C=C(C=C1)C(=O)NC1=C(Cl)C=NC=C1Cl

InChI Identifier

InChI=1S/C17H14Cl2F2N2O3/c18-11-6-22-7-12(19)15(11)23-16(24)10-3-4-13(26-17(20)21)14(5-10)25-8-9-1-2-9/h3-7,9,17H,1-2,8H2,(H,22,23,24)

InChI Key

MNDBXUUTURYVHR-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
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

organofluorine compound (CHEBI:47657 )
aromatic ether (CHEBI:47657 )
benzamides (CHEBI:47657 )
cyclopropanes (CHEBI:47657 )
chloropyridine (CHEBI:47657 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	4.47	ALOGPS
logP	4.45	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	8.18	ChemAxon
pKa (Strongest Basic)	2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	60.45 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	93.92 m³·mol⁻¹	ChemAxon
Polarizability	35.9 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]+	178.977	30932474
DeepCCS	[M-H]-	176.619	30932474
DeepCCS	[M-2H]-	210.783	30932474
DeepCCS	[M+Na]+	186.01	30932474
AllCCS	[M+H]+	184.6	32859911
AllCCS	[M+H-H2O]+	181.9	32859911
AllCCS	[M+NH4]+	187.0	32859911
AllCCS	[M+Na]+	187.7	32859911
AllCCS	[M-H]-	179.5	32859911
AllCCS	[M+Na-2H]-	178.8	32859911
AllCCS	[M+HCOO]-	178.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Roflumilast	FC(F)OC1=C(OCC2CC2)C=C(C=C1)C(=O)NC1=C(Cl)C=NC=C1Cl	3817.6	Standard polar	33892256
Roflumilast	FC(F)OC1=C(OCC2CC2)C=C(C=C1)C(=O)NC1=C(Cl)C=NC=C1Cl	2840.0	Standard non polar	33892256
Roflumilast	FC(F)OC1=C(OCC2CC2)C=C(C=C1)C(=O)NC1=C(Cl)C=NC=C1Cl	2712.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Roflumilast,1TMS,isomer #1	C[Si](C)(C)N(C(=O)C1=CC=C(OC(F)F)C(OCC2CC2)=C1)C1=C(Cl)C=NC=C1Cl	2603.7	Semi standard non polar	33892256
Roflumilast,1TMS,isomer #1	C[Si](C)(C)N(C(=O)C1=CC=C(OC(F)F)C(OCC2CC2)=C1)C1=C(Cl)C=NC=C1Cl	2568.3	Standard non polar	33892256
Roflumilast,1TMS,isomer #1	C[Si](C)(C)N(C(=O)C1=CC=C(OC(F)F)C(OCC2CC2)=C1)C1=C(Cl)C=NC=C1Cl	3420.6	Standard polar	33892256
Roflumilast,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=NC=C1Cl	2803.1	Semi standard non polar	33892256
Roflumilast,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=NC=C1Cl	2759.1	Standard non polar	33892256
Roflumilast,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=NC=C1Cl	3483.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Roflumilast GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udu-8954000000-6f95e21dc2650f78ee74	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Roflumilast 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Roflumilast , positive-QTOF	splash10-0f76-0950700000-9d3dc26457cb82e9e2af	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Roflumilast 10V, Positive-QTOF	splash10-0udi-4143900000-204e321c2bda7d5dfedc	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Roflumilast 20V, Positive-QTOF	splash10-052f-5291200000-4e08a8a2842ed5354d3f	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Roflumilast 40V, Positive-QTOF	splash10-0a4i-9800000000-71b3796368c34787a297	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Roflumilast 10V, Negative-QTOF	splash10-0udi-0106900000-398b518b9346477bbe00	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Roflumilast 20V, Negative-QTOF	splash10-0udj-0439400000-b34905ea512386c7ad78	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Roflumilast 40V, Negative-QTOF	splash10-08g0-1931000000-00d43026562c376dee06	2017-07-26	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

DB01656

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

395793

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Roflumilast

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

47657

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 Roflumilast (HMDB0257288)

MOL for HMDB0257288 (Roflumilast)

3D MOL for HMDB0257288 (Roflumilast)

3D SDF for HMDB0257288 (Roflumilast)

3D-SDF for HMDB0257288 (Roflumilast)

PDB for HMDB0257288 (Roflumilast)

3D PDB for HMDB0257288 (Roflumilast)

SMILES for HMDB0257288 (Roflumilast)

INCHI for HMDB0257288 (Roflumilast)

Structure for HMDB0257288 (Roflumilast)

3D Structure for HMDB0257288 (Roflumilast)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra