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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 17:02:41 UTC

Update Date

2021-09-26 23:12:15 UTC

HMDB ID

HMDB0256530

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Piclamilast

Description

Piclamilast, also known as RP 73-401, 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 Piclamilast. This compound has been identified in human blood as reported by (PMID: 31557052 ). Piclamilast is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Piclamilast 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

HMDB0256530
     RDKit          3D
Piclamilast
 43 45  0  0  0  0  0  0  0  0999 V2000
   -3.2158   -3.7306    1.2641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7781   -2.4414    0.9333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4561   -2.1008    0.7379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4253   -2.9972    0.8482 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8836   -2.6211    0.6458 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1415   -1.2992    0.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4981   -0.8216    0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4170   -1.5960    0.5208 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8378    0.3964   -0.5275 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1940    0.7379   -0.6780 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8392    1.4540    0.2994 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9868    1.9541    1.7480 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.1856    1.7682    0.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8757    1.4076   -0.9857 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2507    0.7091   -1.9417 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9186    0.3762   -1.7890 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0799   -0.5388   -3.0295 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.1023   -0.3838    0.2100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1894   -0.7545    0.4096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2213    0.1375    0.3003 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0945    1.4662   -0.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8554    2.2859    1.0409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2784    1.8077    0.8352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3633    1.3956   -0.6265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0146    1.7458   -1.2204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5156   -4.2957    1.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4520   -4.3195    0.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1847   -3.6575    1.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6525   -4.0424    1.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7106   -3.3196    0.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0923    1.0201   -0.8720 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6903    2.3324    0.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7680    0.4002   -2.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3468    0.6384   -0.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1101    1.8830   -0.1960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4451    2.0014    2.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7982    3.3572    0.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0175    2.6269    1.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4516    0.9124    1.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1875    1.9200   -1.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4581    0.2805   -0.7227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9028    2.8193   -1.4321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7509    1.0857   -2.0643 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
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
  6 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 19  3  1  0
 25 21  1  0
 16 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  9 31  1  0
 13 32  1  0
 15 33  1  0
 18 34  1  0
 21 35  1  0
 22 36  1  0
 22 37  1  0
 23 38  1  0
 23 39  1  0
 24 40  1  0
 24 41  1  0
 25 42  1  0
 25 43  1  0
M  END

PIL
  Mrv0541 02231215432D          

 25 27  0  0  0  0            999 V2000
   -1.9469   -0.9110    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6614   -0.4985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3758   -0.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0903   -0.4985    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0903    0.3265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3758    0.7390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3758    1.5640    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6614    0.3265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9469    0.7390    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2324    0.3265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2324   -0.4985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5180    0.7390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5180    1.5640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1965    1.9765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9110    1.5640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6255    1.9765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3399    1.5640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9110    0.7390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1965    0.3265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6255    0.3265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6255   -0.4985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2929   -0.9834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0380   -1.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2130   -1.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9580   -0.9834    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
  2  8  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 19  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 18  1  0  0  0  0
 16 17  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 25  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0256530

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C(C=C1OC1CCCC1)C(=O)NC1=C(Cl)C=NC=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C18H18Cl2N2O3/c1-24-15-7-6-11(8-16(15)25-12-4-2-3-5-12)18(23)22-17-13(19)9-21-10-14(17)20/h6-10,12H,2-5H2,1H3,(H,21,22,23)

> <INCHI_KEY>
RRRUXBQSQLKHEL-UHFFFAOYSA-N

> <FORMULA>
C18H18Cl2N2O3

> <MOLECULAR_WEIGHT>
381.253

> <EXACT_MASS>
380.069447866

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
37.227570122928434

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(cyclopentyloxy)-N-(3,5-dichloropyridin-4-yl)-4-methoxybenzamide

> <ALOGPS_LOGP>
4.65

> <JCHEM_LOGP>
4.094906882666667

> <ALOGPS_LOGS>
-4.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.248246776135781

> <JCHEM_PKA_STRONGEST_BASIC>
2.399654380859954

> <JCHEM_POLAR_SURFACE_AREA>
60.45

> <JCHEM_REFRACTIVITY>
98.38380000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.10e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
piclamilast

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0256530
     RDKit          3D
Piclamilast
 43 45  0  0  0  0  0  0  0  0999 V2000
   -3.2158   -3.7306    1.2641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7781   -2.4414    0.9333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4561   -2.1008    0.7379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4253   -2.9972    0.8482 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8836   -2.6211    0.6458 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1415   -1.2992    0.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4981   -0.8216    0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4170   -1.5960    0.5208 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8378    0.3964   -0.5275 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1940    0.7379   -0.6780 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8392    1.4540    0.2994 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9868    1.9541    1.7480 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.1856    1.7682    0.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8757    1.4076   -0.9857 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2507    0.7091   -1.9417 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9186    0.3762   -1.7890 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0799   -0.5388   -3.0295 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.1023   -0.3838    0.2100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1894   -0.7545    0.4096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2213    0.1375    0.3003 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0945    1.4662   -0.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8554    2.2859    1.0409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2784    1.8077    0.8352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3633    1.3956   -0.6265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0146    1.7458   -1.2204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5156   -4.2957    1.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4520   -4.3195    0.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1847   -3.6575    1.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6525   -4.0424    1.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7106   -3.3196    0.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0923    1.0201   -0.8720 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6903    2.3324    0.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7680    0.4002   -2.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3468    0.6384   -0.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1101    1.8830   -0.1960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4451    2.0014    2.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7982    3.3572    0.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0175    2.6269    1.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4516    0.9124    1.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1875    1.9200   -1.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4581    0.2805   -0.7227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9028    2.8193   -1.4321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7509    1.0857   -2.0643 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
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
  6 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 19  3  1  0
 25 21  1  0
 16 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  9 31  1  0
 13 32  1  0
 15 33  1  0
 18 34  1  0
 21 35  1  0
 22 36  1  0
 22 37  1  0
 23 38  1  0
 23 39  1  0
 24 40  1  0
 24 41  1  0
 25 42  1  0
 25 43  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: PIL                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0      -3.634  -1.701   0.000  0.00  0.00          Cl+0
HETATM    2  C   UNK     0      -4.968  -0.931   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.301  -1.701   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      -7.635  -0.931   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -7.635   0.609   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.301   1.379   0.000  0.00  0.00           C+0
HETATM    7 Cl   UNK     0      -6.301   2.919   0.000  0.00  0.00          Cl+0
HETATM    8  C   UNK     0      -4.968   0.609   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -3.634   1.379   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -2.300   0.609   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.300  -0.931   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.967   1.379   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.967   2.919   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.367   3.689   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.701   2.919   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.034   3.689   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.368   2.919   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.701   1.379   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.367   0.609   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.034   0.609   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.034  -0.931   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.280  -1.836   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.804  -3.300   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.264  -3.300   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.788  -1.836   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    2    6    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19   20                                                  
CONECT   19   12   18                                                       
CONECT   20   18   21                                                       
CONECT   21   20   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   21   24                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0256530
HETATM    1  C1  UNL     1      -3.216  -3.731   1.264  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.778  -2.441   0.933  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.456  -2.101   0.738  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.425  -2.997   0.848  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.884  -2.621   0.646  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.141  -1.299   0.324  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.498  -0.822   0.101  1.00  0.00           C  
HETATM    8  O2  UNL     1       3.417  -1.596   0.521  1.00  0.00           O  
HETATM    9  N1  UNL     1       2.838   0.396  -0.528  1.00  0.00           N  
HETATM   10  C7  UNL     1       4.194   0.738  -0.678  1.00  0.00           C  
HETATM   11  C8  UNL     1       4.839   1.454   0.299  1.00  0.00           C  
HETATM   12 CL1  UNL     1       3.987   1.954   1.748  1.00  0.00          CL  
HETATM   13  C9  UNL     1       6.186   1.768   0.103  1.00  0.00           C  
HETATM   14  N2  UNL     1       6.876   1.408  -0.986  1.00  0.00           N  
HETATM   15  C10 UNL     1       6.251   0.709  -1.942  1.00  0.00           C  
HETATM   16  C11 UNL     1       4.919   0.376  -1.789  1.00  0.00           C  
HETATM   17 CL2  UNL     1       4.080  -0.539  -3.029  1.00  0.00          CL  
HETATM   18  C12 UNL     1       0.102  -0.384   0.210  1.00  0.00           C  
HETATM   19  C13 UNL     1      -1.189  -0.755   0.410  1.00  0.00           C  
HETATM   20  O3  UNL     1      -2.221   0.138   0.300  1.00  0.00           O  
HETATM   21  C14 UNL     1      -2.095   1.466  -0.012  1.00  0.00           C  
HETATM   22  C15 UNL     1      -2.855   2.286   1.041  1.00  0.00           C  
HETATM   23  C16 UNL     1      -4.278   1.808   0.835  1.00  0.00           C  
HETATM   24  C17 UNL     1      -4.363   1.396  -0.626  1.00  0.00           C  
HETATM   25  C18 UNL     1      -3.015   1.746  -1.220  1.00  0.00           C  
HETATM   26  H1  UNL     1      -2.516  -4.296   1.899  1.00  0.00           H  
HETATM   27  H2  UNL     1      -3.452  -4.319   0.339  1.00  0.00           H  
HETATM   28  H3  UNL     1      -4.185  -3.657   1.829  1.00  0.00           H  
HETATM   29  H4  UNL     1      -0.652  -4.042   1.105  1.00  0.00           H  
HETATM   30  H5  UNL     1       1.711  -3.320   0.730  1.00  0.00           H  
HETATM   31  H6  UNL     1       2.092   1.020  -0.872  1.00  0.00           H  
HETATM   32  H7  UNL     1       6.690   2.332   0.875  1.00  0.00           H  
HETATM   33  H8  UNL     1       6.768   0.400  -2.831  1.00  0.00           H  
HETATM   34  H9  UNL     1       0.347   0.638  -0.039  1.00  0.00           H  
HETATM   35  H10 UNL     1      -1.110   1.883  -0.196  1.00  0.00           H  
HETATM   36  H11 UNL     1      -2.445   2.001   2.016  1.00  0.00           H  
HETATM   37  H12 UNL     1      -2.798   3.357   0.849  1.00  0.00           H  
HETATM   38  H13 UNL     1      -5.017   2.627   1.044  1.00  0.00           H  
HETATM   39  H14 UNL     1      -4.452   0.912   1.442  1.00  0.00           H  
HETATM   40  H15 UNL     1      -5.188   1.920  -1.150  1.00  0.00           H  
HETATM   41  H16 UNL     1      -4.458   0.280  -0.723  1.00  0.00           H  
HETATM   42  H17 UNL     1      -2.903   2.819  -1.432  1.00  0.00           H  
HETATM   43  H18 UNL     1      -2.751   1.086  -2.064  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3
CONECT    3    4    4   19
CONECT    4    5   29
CONECT    5    6    6   30
CONECT    6    7   18
CONECT    7    8    8    9
CONECT    9   10   31
CONECT   10   11   11   16
CONECT   11   12   13
CONECT   13   14   14   32
CONECT   14   15
CONECT   15   16   16   33
CONECT   16   17
CONECT   18   19   19   34
CONECT   19   20
CONECT   20   21
CONECT   21   22   25   35
CONECT   22   23   36   37
CONECT   23   24   38   39
CONECT   24   25   40   41
CONECT   25   42   43
END

HMDB0256530
     RDKit          3D
Piclamilast
 43 45  0  0  0  0  0  0  0  0999 V2000
   -3.2158   -3.7306    1.2641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7781   -2.4414    0.9333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4561   -2.1008    0.7379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4253   -2.9972    0.8482 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8836   -2.6211    0.6458 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1415   -1.2992    0.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4981   -0.8216    0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4170   -1.5960    0.5208 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8378    0.3964   -0.5275 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1940    0.7379   -0.6780 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8392    1.4540    0.2994 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9868    1.9541    1.7480 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.1856    1.7682    0.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8757    1.4076   -0.9857 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2507    0.7091   -1.9417 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9186    0.3762   -1.7890 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0799   -0.5388   -3.0295 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.1023   -0.3838    0.2100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1894   -0.7545    0.4096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2213    0.1375    0.3003 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0945    1.4662   -0.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8554    2.2859    1.0409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2784    1.8077    0.8352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3633    1.3956   -0.6265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0146    1.7458   -1.2204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5156   -4.2957    1.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4520   -4.3195    0.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1847   -3.6575    1.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6525   -4.0424    1.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7106   -3.3196    0.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0923    1.0201   -0.8720 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6903    2.3324    0.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7680    0.4002   -2.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3468    0.6384   -0.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1101    1.8830   -0.1960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4451    2.0014    2.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7982    3.3572    0.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0175    2.6269    1.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4516    0.9124    1.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1875    1.9200   -1.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4581    0.2805   -0.7227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9028    2.8193   -1.4321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7509    1.0857   -2.0643 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
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
  6 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 19  3  1  0
 25 21  1  0
 16 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  9 31  1  0
 13 32  1  0
 15 33  1  0
 18 34  1  0
 21 35  1  0
 22 36  1  0
 22 37  1  0
 23 38  1  0
 23 39  1  0
 24 40  1  0
 24 41  1  0
 25 42  1  0
 25 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-(Cyclopentyloxy)-N-(3,5-dichloro-4-pyridinyl)-4-methoxybenzamide	ChEBI
3-(Cyclopentyloxy)-N-(3,5-dichloro-4-pyridyl)-p-anisamide	ChEBI
Piclamilastum	ChEBI
RP 73-401	ChEBI
RP 73401	ChEBI
RP-73-401	ChEBI
3-(Cyclopentyloxy)-N-(3,5-dichloro-4-pyridyl)-4-methoxybenzamide	MeSH
3-Cyclopentyloxy-N-(3,5-dichloro-4-pyridyl)-4-methoxybenzamide	MeSH

Chemical Formula

C₁₈H₁₈Cl₂N₂O₃

Average Molecular Weight

381.253

Monoisotopic Molecular Weight

380.069447866

IUPAC Name

3-(cyclopentyloxy)-N-(3,5-dichloropyridin-4-yl)-4-methoxybenzamide

Traditional Name

piclamilast

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1OC1CCCC1)C(=O)NC1=C(Cl)C=NC=C1Cl

InChI Identifier

InChI=1S/C18H18Cl2N2O3/c1-24-15-7-6-11(8-16(15)25-12-4-2-3-5-12)18(23)22-17-13(19)9-21-10-14(17)20/h6-10,12H,2-5H2,1H3,(H,21,22,23)

InChI Key

RRRUXBQSQLKHEL-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
Anisole
Benzoyl
Phenol ether
Methoxybenzene
Polyhalopyridine
Alkyl aryl ether
Aryl chloride
Aryl halide
Pyridine
Heteroaromatic compound
Carboxamide group
Secondary carboxylic acid amide
Organoheterocyclic compound
Azacycle
Ether
Carboxylic acid derivative
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

aromatic ether (CHEBI:47619 )
monocarboxylic acid amide (CHEBI:47619 )
benzamides (CHEBI:47619 )
chloropyridine (CHEBI:47619 )

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	4.65	ALOGPS
logP	4.09	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	8.25	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	5	ChemAxon
Refractivity	98.38 m³·mol⁻¹	ChemAxon
Polarizability	37.23 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	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	181.323	30932474
DeepCCS	[M-H]-	178.965	30932474
DeepCCS	[M-2H]-	212.983	30932474
DeepCCS	[M+Na]+	188.335	30932474
AllCCS	[M+H]+	184.7	32859911
AllCCS	[M+H-H2O]+	181.9	32859911
AllCCS	[M+NH4]+	187.2	32859911
AllCCS	[M+Na]+	187.9	32859911
AllCCS	[M-H]-	183.2	32859911
AllCCS	[M+Na-2H]-	183.3	32859911
AllCCS	[M+HCOO]-	183.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Piclamilast	COC1=CC=C(C=C1OC1CCCC1)C(=O)NC1=C(Cl)C=NC=C1Cl	4241.3	Standard polar	33892256
Piclamilast	COC1=CC=C(C=C1OC1CCCC1)C(=O)NC1=C(Cl)C=NC=C1Cl	3042.2	Standard non polar	33892256
Piclamilast	COC1=CC=C(C=C1OC1CCCC1)C(=O)NC1=C(Cl)C=NC=C1Cl	3083.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Piclamilast,1TMS,isomer #1	COC1=CC=C(C(=O)N(C2=C(Cl)C=NC=C2Cl)[Si](C)(C)C)C=C1OC1CCCC1	2894.1	Semi standard non polar	33892256
Piclamilast,1TMS,isomer #1	COC1=CC=C(C(=O)N(C2=C(Cl)C=NC=C2Cl)[Si](C)(C)C)C=C1OC1CCCC1	2727.7	Standard non polar	33892256
Piclamilast,1TMS,isomer #1	COC1=CC=C(C(=O)N(C2=C(Cl)C=NC=C2Cl)[Si](C)(C)C)C=C1OC1CCCC1	3760.7	Standard polar	33892256
Piclamilast,1TBDMS,isomer #1	COC1=CC=C(C(=O)N(C2=C(Cl)C=NC=C2Cl)[Si](C)(C)C(C)(C)C)C=C1OC1CCCC1	3073.6	Semi standard non polar	33892256
Piclamilast,1TBDMS,isomer #1	COC1=CC=C(C(=O)N(C2=C(Cl)C=NC=C2Cl)[Si](C)(C)C(C)(C)C)C=C1OC1CCCC1	2902.7	Standard non polar	33892256
Piclamilast,1TBDMS,isomer #1	COC1=CC=C(C(=O)N(C2=C(Cl)C=NC=C2Cl)[Si](C)(C)C(C)(C)C)C=C1OC1CCCC1	3836.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Piclamilast GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gb9-6934000000-f53ab83801cc440b678c	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Piclamilast 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 - Piclamilast 10V, Positive-QTOF	splash10-00lr-2129000000-e8c4556f20f54631ff10	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piclamilast 20V, Positive-QTOF	splash10-014i-5595000000-44ad192d5af359043793	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piclamilast 40V, Positive-QTOF	splash10-0gb9-9400000000-6cdb01548f4f49681bd8	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piclamilast 10V, Negative-QTOF	splash10-004i-0109000000-1340a0c23ec7c25b069b	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piclamilast 20V, Negative-QTOF	splash10-01t9-0449000000-708b674f4de447be9477	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piclamilast 40V, Negative-QTOF	splash10-03di-2940000000-60f96ccb1996b1eb3080	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

DB01791

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

136184

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Piclamilast

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

47619

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 Piclamilast (HMDB0256530)

MOL for HMDB0256530 (Piclamilast)

3D MOL for HMDB0256530 (Piclamilast)

3D SDF for HMDB0256530 (Piclamilast)

3D-SDF for HMDB0256530 (Piclamilast)

PDB for HMDB0256530 (Piclamilast)

3D PDB for HMDB0256530 (Piclamilast)

SMILES for HMDB0256530 (Piclamilast)

INCHI for HMDB0256530 (Piclamilast)

Structure for HMDB0256530 (Piclamilast)

3D Structure for HMDB0256530 (Piclamilast)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra