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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 07:13:49 UTC

Update Date

2021-09-26 23:01:35 UTC

HMDB ID

HMDB0250246

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Cilomilast

Description

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

HMDB0250246
     RDKit          3D
Cilomilast
 50 52  0  0  0  0  0  0  0  0999 V2000
   -2.6854   -3.4570   -1.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6347   -2.1011   -0.8348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4504   -1.4896   -0.4740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2929   -2.2321   -0.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9151   -1.6531   -0.0684 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9532   -0.2997    0.2465 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2239    0.3692    0.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8567    1.3909    1.6457 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5854    2.1991    2.4370 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2408   -0.5334    1.2330 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3506   -0.9572    0.3332 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9378    0.1257   -0.5046 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3796    0.3393   -0.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9272   -0.3694    0.6991 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1608    1.2907   -0.8003 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2208    1.4297   -0.4200 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7415    1.1508   -0.5534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2280    0.4261    0.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4510   -0.1284   -0.1641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5298    0.6809   -0.1787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8538    0.4798   -0.4971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5424    1.6437   -1.1664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9616    1.5307   -0.6234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7187    1.2971    0.8395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5862    0.3300    0.8644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5493   -4.0231   -0.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6507   -3.7267   -1.6383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8344   -3.6915   -1.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2541   -3.2858   -0.6567 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8046   -2.2499   -0.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7020   -0.0465    2.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7302   -1.4399    1.6157 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1696   -1.3447    1.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1232   -1.8251   -0.3157 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9310   -0.1595   -1.5988 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2743    2.2344   -0.4614 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4620    2.0107    0.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5165    2.0536   -1.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5725    0.5817   -1.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2176    2.1255   -0.6394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2261    1.4946    0.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0961   -0.4240   -1.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0949    2.5681   -0.7385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5154    1.6030   -2.2656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4747    0.6461   -1.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5173    2.4752   -0.7978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4450    2.2580    1.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5972    0.8568    1.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9144    0.5762    1.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8924   -0.7301    0.9937 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  1  0
  8  9  3  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 12 16  1  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
 17  7  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 21 42  1  0
 22 43  1  0
 22 44  1  0
 23 45  1  0
 23 46  1  0
 24 47  1  0
 24 48  1  0
 25 49  1  0
 25 50  1  0
M  END

  Mrv1652309112109142D          

 25 27  0  0  0  0            999 V2000
   -0.2929    0.5097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2929   -0.3153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0073   -0.7278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0073   -1.5528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7218   -1.9653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4363   -1.5528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4363   -0.7278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7218   -0.3153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1507   -1.9653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6810   -2.5973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4935   -2.4540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7757   -1.6788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2454   -1.0468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4329   -1.1901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5881   -1.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8703   -0.7603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1184   -2.1675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6204   -2.5973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0901   -3.2293    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2929   -1.9653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2929   -2.7903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3746   -3.2752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1196   -4.0598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7054   -4.0598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9603   -3.2752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  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
  9 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  3  0  0  0  0
  4 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0250246

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OC2CCCC2)C=C(C=C1)C1(CCC(CC1)C(O)=O)C#N

> <INCHI_IDENTIFIER>
InChI=1S/C20H25NO4/c1-24-17-7-6-15(12-18(17)25-16-4-2-3-5-16)20(13-21)10-8-14(9-11-20)19(22)23/h6-7,12,14,16H,2-5,8-11H2,1H3,(H,22,23)

> <INCHI_KEY>
CFBUZOUXXHZCFB-UHFFFAOYSA-N

> <FORMULA>
C20H25NO4

> <MOLECULAR_WEIGHT>
343.423

> <EXACT_MASS>
343.178358289

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
37.27838403201292

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]cyclohexane-1-carboxylic acid

> <ALOGPS_LOGP>
3.91

> <JCHEM_LOGP>
3.9000274933333348

> <ALOGPS_LOGS>
-4.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.327759063297154

> <JCHEM_PKA_STRONGEST_BASIC>
-4.608520197977659

> <JCHEM_POLAR_SURFACE_AREA>
79.55

> <JCHEM_REFRACTIVITY>
93.0007

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.55e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cilomilast

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0250246
     RDKit          3D
Cilomilast
 50 52  0  0  0  0  0  0  0  0999 V2000
   -2.6854   -3.4570   -1.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6347   -2.1011   -0.8348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4504   -1.4896   -0.4740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2929   -2.2321   -0.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9151   -1.6531   -0.0684 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9532   -0.2997    0.2465 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2239    0.3692    0.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8567    1.3909    1.6457 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5854    2.1991    2.4370 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2408   -0.5334    1.2330 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3506   -0.9572    0.3332 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9378    0.1257   -0.5046 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3796    0.3393   -0.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9272   -0.3694    0.6991 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1608    1.2907   -0.8003 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2208    1.4297   -0.4200 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7415    1.1508   -0.5534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2280    0.4261    0.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4510   -0.1284   -0.1641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5298    0.6809   -0.1787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8538    0.4798   -0.4971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5424    1.6437   -1.1664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9616    1.5307   -0.6234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7187    1.2971    0.8395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5862    0.3300    0.8644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5493   -4.0231   -0.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6507   -3.7267   -1.6383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8344   -3.6915   -1.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2541   -3.2858   -0.6567 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8046   -2.2499   -0.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7020   -0.0465    2.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7302   -1.4399    1.6157 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1696   -1.3447    1.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1232   -1.8251   -0.3157 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9310   -0.1595   -1.5988 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2743    2.2344   -0.4614 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4620    2.0107    0.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5165    2.0536   -1.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5725    0.5817   -1.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2176    2.1255   -0.6394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2261    1.4946    0.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0961   -0.4240   -1.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0949    2.5681   -0.7385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5154    1.6030   -2.2656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4747    0.6461   -1.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5173    2.4752   -0.7978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4450    2.2580    1.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5972    0.8568    1.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9144    0.5762    1.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8924   -0.7301    0.9937 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  1  0
  8  9  3  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 12 16  1  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
 17  7  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 21 42  1  0
 22 43  1  0
 22 44  1  0
 23 45  1  0
 23 46  1  0
 24 47  1  0
 24 48  1  0
 25 49  1  0
 25 50  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      -0.547   0.951   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.547  -0.589   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.880  -1.359   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.880  -2.899   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.214  -3.669   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.548  -2.899   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.548  -1.359   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.214  -0.589   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.881  -3.669   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.871  -4.848   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.388  -4.581   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -8.915  -3.134   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -7.925  -1.954   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.408  -2.221   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -10.431  -2.866   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0     -10.958  -1.419   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0     -11.421  -4.046   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -4.891  -4.848   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      -3.902  -6.028   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0      -0.547  -3.669   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.547  -5.209   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.699  -6.114   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.223  -7.578   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.317  -7.578   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.793  -6.114   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5   20                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3                                                       
CONECT    9    6   10   14   18                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    9   19                                                       
CONECT   19   18                                                            
CONECT   20    4   21                                                       
CONECT   21   20   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   21                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0250246
HETATM    1  C1  UNL     1      -2.685  -3.457  -1.150  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.635  -2.101  -0.835  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.450  -1.490  -0.474  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.293  -2.232  -0.426  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.915  -1.653  -0.068  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.953  -0.300   0.247  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.224   0.369   0.637  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.857   1.391   1.646  1.00  0.00           C  
HETATM    9  N1  UNL     1       1.585   2.199   2.437  1.00  0.00           N  
HETATM   10  C8  UNL     1       3.241  -0.533   1.233  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.351  -0.957   0.333  1.00  0.00           C  
HETATM   12  C10 UNL     1       4.938   0.126  -0.505  1.00  0.00           C  
HETATM   13  C11 UNL     1       6.380   0.339  -0.179  1.00  0.00           C  
HETATM   14  O2  UNL     1       6.927  -0.369   0.699  1.00  0.00           O  
HETATM   15  O3  UNL     1       7.161   1.291  -0.800  1.00  0.00           O  
HETATM   16  C12 UNL     1       4.221   1.430  -0.420  1.00  0.00           C  
HETATM   17  C13 UNL     1       2.742   1.151  -0.553  1.00  0.00           C  
HETATM   18  C14 UNL     1      -0.228   0.426   0.191  1.00  0.00           C  
HETATM   19  C15 UNL     1      -1.451  -0.128  -0.164  1.00  0.00           C  
HETATM   20  O4  UNL     1      -2.530   0.681  -0.179  1.00  0.00           O  
HETATM   21  C16 UNL     1      -3.854   0.480  -0.497  1.00  0.00           C  
HETATM   22  C17 UNL     1      -4.542   1.644  -1.166  1.00  0.00           C  
HETATM   23  C18 UNL     1      -5.962   1.531  -0.623  1.00  0.00           C  
HETATM   24  C19 UNL     1      -5.719   1.297   0.839  1.00  0.00           C  
HETATM   25  C20 UNL     1      -4.586   0.330   0.864  1.00  0.00           C  
HETATM   26  H1  UNL     1      -2.549  -4.023  -0.194  1.00  0.00           H  
HETATM   27  H2  UNL     1      -3.651  -3.727  -1.638  1.00  0.00           H  
HETATM   28  H3  UNL     1      -1.834  -3.691  -1.821  1.00  0.00           H  
HETATM   29  H4  UNL     1      -0.254  -3.286  -0.657  1.00  0.00           H  
HETATM   30  H5  UNL     1       1.805  -2.250  -0.037  1.00  0.00           H  
HETATM   31  H6  UNL     1       3.702  -0.047   2.143  1.00  0.00           H  
HETATM   32  H7  UNL     1       2.730  -1.440   1.616  1.00  0.00           H  
HETATM   33  H8  UNL     1       5.170  -1.345   1.008  1.00  0.00           H  
HETATM   34  H9  UNL     1       4.123  -1.825  -0.316  1.00  0.00           H  
HETATM   35  H10 UNL     1       4.931  -0.160  -1.599  1.00  0.00           H  
HETATM   36  H11 UNL     1       7.274   2.234  -0.461  1.00  0.00           H  
HETATM   37  H12 UNL     1       4.462   2.011   0.495  1.00  0.00           H  
HETATM   38  H13 UNL     1       4.517   2.054  -1.289  1.00  0.00           H  
HETATM   39  H14 UNL     1       2.572   0.582  -1.474  1.00  0.00           H  
HETATM   40  H15 UNL     1       2.218   2.126  -0.639  1.00  0.00           H  
HETATM   41  H16 UNL     1      -0.226   1.495   0.436  1.00  0.00           H  
HETATM   42  H17 UNL     1      -4.096  -0.424  -1.096  1.00  0.00           H  
HETATM   43  H18 UNL     1      -4.095   2.568  -0.739  1.00  0.00           H  
HETATM   44  H19 UNL     1      -4.515   1.603  -2.266  1.00  0.00           H  
HETATM   45  H20 UNL     1      -6.475   0.646  -1.040  1.00  0.00           H  
HETATM   46  H21 UNL     1      -6.517   2.475  -0.798  1.00  0.00           H  
HETATM   47  H22 UNL     1      -5.445   2.258   1.334  1.00  0.00           H  
HETATM   48  H23 UNL     1      -6.597   0.857   1.361  1.00  0.00           H  
HETATM   49  H24 UNL     1      -3.914   0.576   1.706  1.00  0.00           H  
HETATM   50  H25 UNL     1      -4.892  -0.730   0.994  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   10   17
CONECT    8    9    9    9
CONECT   10   11   31   32
CONECT   11   12   33   34
CONECT   12   13   16   35
CONECT   13   14   14   15
CONECT   15   36
CONECT   16   17   37   38
CONECT   17   39   40
CONECT   18   19   19   41
CONECT   19   20
CONECT   20   21
CONECT   21   22   25   42
CONECT   22   23   43   44
CONECT   23   24   45   46
CONECT   24   25   47   48
CONECT   25   49   50
END

HMDB0250246
     RDKit          3D
Cilomilast
 50 52  0  0  0  0  0  0  0  0999 V2000
   -2.6854   -3.4570   -1.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6347   -2.1011   -0.8348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4504   -1.4896   -0.4740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2929   -2.2321   -0.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9151   -1.6531   -0.0684 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9532   -0.2997    0.2465 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2239    0.3692    0.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8567    1.3909    1.6457 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5854    2.1991    2.4370 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2408   -0.5334    1.2330 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3506   -0.9572    0.3332 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9378    0.1257   -0.5046 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3796    0.3393   -0.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9272   -0.3694    0.6991 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1608    1.2907   -0.8003 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2208    1.4297   -0.4200 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7415    1.1508   -0.5534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2280    0.4261    0.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4510   -0.1284   -0.1641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5298    0.6809   -0.1787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8538    0.4798   -0.4971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5424    1.6437   -1.1664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9616    1.5307   -0.6234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7187    1.2971    0.8395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5862    0.3300    0.8644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5493   -4.0231   -0.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6507   -3.7267   -1.6383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8344   -3.6915   -1.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2541   -3.2858   -0.6567 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8046   -2.2499   -0.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7020   -0.0465    2.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7302   -1.4399    1.6157 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1696   -1.3447    1.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1232   -1.8251   -0.3157 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9310   -0.1595   -1.5988 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2743    2.2344   -0.4614 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4620    2.0107    0.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5165    2.0536   -1.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5725    0.5817   -1.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2176    2.1255   -0.6394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2261    1.4946    0.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0961   -0.4240   -1.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0949    2.5681   -0.7385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5154    1.6030   -2.2656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4747    0.6461   -1.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5173    2.4752   -0.7978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4450    2.2580    1.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5972    0.8568    1.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9144    0.5762    1.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8924   -0.7301    0.9937 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  1  0
  8  9  3  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 12 16  1  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
 17  7  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 21 42  1  0
 22 43  1  0
 22 44  1  0
 23 45  1  0
 23 46  1  0
 24 47  1  0
 24 48  1  0
 25 49  1  0
 25 50  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Ariflo	HMDB

Chemical Formula

C₂₀H₂₅NO₄

Average Molecular Weight

343.423

Monoisotopic Molecular Weight

343.178358289

IUPAC Name

4-cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]cyclohexane-1-carboxylic acid

Traditional Name

cilomilast

CAS Registry Number

Not Available

SMILES

COC1=C(OC2CCCC2)C=C(C=C1)C1(CCC(CC1)C(O)=O)C#N

InChI Identifier

InChI=1S/C20H25NO4/c1-24-17-7-6-15(12-18(17)25-16-4-2-3-5-16)20(13-21)10-8-14(9-11-20)19(22)23/h6-7,12,14,16H,2-5,8-11H2,1H3,(H,22,23)

InChI Key

CFBUZOUXXHZCFB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Phenoxy compound
Anisole
Methoxybenzene
Alkyl aryl ether
Monocyclic benzene moiety
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Carbonitrile
Nitrile
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0250246)

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	3.91	ALOGPS
logP	3.9	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	2.33	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	79.55 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	93 m³·mol⁻¹	ChemAxon
Polarizability	37.28 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]+	183.785	30932474
DeepCCS	[M-H]-	181.427	30932474
DeepCCS	[M-2H]-	215.591	30932474
DeepCCS	[M+Na]+	191.2	30932474
AllCCS	[M+H]+	183.5	32859911
AllCCS	[M+H-H2O]+	180.6	32859911
AllCCS	[M+NH4]+	186.1	32859911
AllCCS	[M+Na]+	186.9	32859911
AllCCS	[M-H]-	185.2	32859911
AllCCS	[M+Na-2H]-	185.4	32859911
AllCCS	[M+HCOO]-	185.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cilomilast	COC1=C(OC2CCCC2)C=C(C=C1)C1(CCC(CC1)C(O)=O)C#N	3068.9	Standard polar	33892256
Cilomilast	COC1=C(OC2CCCC2)C=C(C=C1)C1(CCC(CC1)C(O)=O)C#N	2755.6	Standard non polar	33892256
Cilomilast	COC1=C(OC2CCCC2)C=C(C=C1)C1(CCC(CC1)C(O)=O)C#N	2858.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cilomilast GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6s-1091000000-15917b04ce96eadc7544	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cilomilast GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cilomilast GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cilomilast GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	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 - Cilomilast 10V, Positive-QTOF	splash10-0006-2159000000-fb3033de5b75d0fd9b47	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cilomilast 20V, Positive-QTOF	splash10-06dm-1290000000-d5f8b472839fd052da22	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cilomilast 40V, Positive-QTOF	splash10-014l-9450000000-cfac3e8f96922ba5aa0a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cilomilast 10V, Negative-QTOF	splash10-0006-0009000000-67609b6585e8919a2e87	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cilomilast 20V, Negative-QTOF	splash10-054o-1097000000-508309fedbf9cbef3f58	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cilomilast 40V, Negative-QTOF	splash10-0f92-1593000000-5824a6d1b0bb56ca3472	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

133238

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cilomilast

METLIN ID

Not Available

PubChem Compound

151170

PDB ID

Not Available

ChEBI ID

94683

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 Cilomilast (HMDB0250246)

MOL for HMDB0250246 (Cilomilast)

3D MOL for HMDB0250246 (Cilomilast)

3D SDF for HMDB0250246 (Cilomilast)

3D-SDF for HMDB0250246 (Cilomilast)

PDB for HMDB0250246 (Cilomilast)

3D PDB for HMDB0250246 (Cilomilast)

SMILES for HMDB0250246 (Cilomilast)

INCHI for HMDB0250246 (Cilomilast)

Structure for HMDB0250246 (Cilomilast)

3D Structure for HMDB0250246 (Cilomilast)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra