Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (7) Show 7 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:56 UTC

HMDB ID

HMDB0015297

Secondary Accession Numbers

HMDB15297

Metabolite Identification

Common Name

Cilostazol

Description

Cilostazol, also known as pletal, belongs to the class of organic compounds known as hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group. Cilostazol is an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, cilostazol participates in a number of enzymatic reactions. In particular, cilostazol can be converted into 4-hydroxycilostazol; which is mediated by the enzyme cytochrome P450 3A4. In addition, cilostazol can be converted into 4-cis-hydroxy cilostazol through its interaction with the enzymes cytochrome P450 2C19 and cytochrome P450 3A5. In humans, cilostazol is involved in cilostazol action pathway. A lactam that is 3,4-dihydroquinolin-2(1H)-one in which the hydrogen at position 6 is substituted by a 4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy group.

Structure

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

1166
  Mrv0541 02231215172D          

 27 30  0  0  0  0            999 V2000
    5.9913   -0.0906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.7606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3176   -0.1509    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8720   -0.7618    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6546   -1.3094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4622   -1.4779    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.7606    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4860    0.6568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8708    1.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2697    0.9148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0392    2.0141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4380    1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8228    2.2721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5652   -0.4893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8492   -0.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1363   -0.4948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4202   -0.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7073   -0.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -0.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2784   -0.5058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5309   -0.0819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5309   -1.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2784   -1.3652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  1 23  1  0  0  0  0
  2 25  2  0  0  0  0
  3  4  1  0  0  0  0
  3  8  1  0  0  0  0
  3 14  1  0  0  0  0
  4  6  2  0  0  0  0
  5  6  1  0  0  0  0
  5 14  2  0  0  0  0
  7 21  1  0  0  0  0
  7 25  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 19 24  1  0  0  0  0
 20 22  1  0  0  0  0
 21 26  1  0  0  0  0
 22 25  1  0  0  0  0
 23 24  2  0  0  0  0
 23 27  1  0  0  0  0
 26 27  2  0  0  0  0
M  END

HMDB0015297
     RDKit          3D
Cilostazol
 54 57  0  0  0  0  0  0  0  0999 V2000
    9.6717    0.4699   -0.5152 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4986    0.2232   -0.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9119    0.7664    1.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5874    1.4007    0.7659 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7542    0.5151   -0.0752 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3786    0.6676   -0.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5606   -0.1364   -0.8081 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1861    0.0335   -0.7576 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5788    1.0246    0.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0674    0.8772   -0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2858   -0.5146    0.2358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7337   -0.8639    0.0769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6362   -0.0164    0.8862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2456    0.9622    1.7002 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3239    1.4822    2.2408 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3778    0.8417    1.7751 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9680   -0.0857    0.9381 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8355   -0.9852    0.2325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9877   -0.5324   -1.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4089   -0.2527   -1.5823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0167    0.6373   -0.5200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0889   -0.0489    0.8185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1455   -1.2118    0.9362 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0589   -1.1116   -1.6321 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4419   -1.2568   -1.6602 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2684   -0.4582   -0.8964 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6932   -0.6196   -0.9359 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5477    1.5717    1.5454 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7135   -0.0404    1.8484 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7357    2.3817    0.2732 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0851    1.6335    1.7487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9669    1.4268    0.5996 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7332    0.8127    1.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9106    2.0386   -0.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4914    1.6821    0.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0423    1.0270   -1.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3822   -1.2010   -0.3209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0355   -0.7086    1.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9621   -0.7926   -1.0146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9471   -1.9141    0.3615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3138   -1.9829    0.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3534    0.3733   -1.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6000   -1.2957   -1.9191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9333   -1.2139   -1.6566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4170    0.2826   -2.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3517    1.5262   -0.4386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0182    0.9433   -0.8899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1210   -0.4387    0.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9271    0.6833    1.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6169   -2.1548    0.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9166   -1.3445    2.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3993   -1.7364   -2.2307 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8849   -2.0054   -2.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0845   -1.3611   -1.5615 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  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
  7 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27  2  1  0
 26  5  1  0
 17 13  1  0
 23 18  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  6 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
 21 47  1  0
 22 48  1  0
 22 49  1  0
 23 50  1  0
 23 51  1  0
 24 52  1  0
 25 53  1  0
 27 54  1  0
M  END

1166
  Mrv0541 02231215172D          

 27 30  0  0  0  0            999 V2000
    5.9913   -0.0906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.7606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3176   -0.1509    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8720   -0.7618    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6546   -1.3094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4622   -1.4779    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.7606    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4860    0.6568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8708    1.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2697    0.9148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0392    2.0141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4380    1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8228    2.2721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5652   -0.4893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8492   -0.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1363   -0.4948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4202   -0.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7073   -0.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -0.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2784   -0.5058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5309   -0.0819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5309   -1.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2784   -1.3652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  1 23  1  0  0  0  0
  2 25  2  0  0  0  0
  3  4  1  0  0  0  0
  3  8  1  0  0  0  0
  3 14  1  0  0  0  0
  4  6  2  0  0  0  0
  5  6  1  0  0  0  0
  5 14  2  0  0  0  0
  7 21  1  0  0  0  0
  7 25  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 19 24  1  0  0  0  0
 20 22  1  0  0  0  0
 21 26  1  0  0  0  0
 22 25  1  0  0  0  0
 23 24  2  0  0  0  0
 23 27  1  0  0  0  0
 26 27  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015297

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C1CCC2=C(N1)C=CC(OCCCCC1=NN=NN1C1CCCCC1)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C20H27N5O2/c26-20-12-9-15-14-17(10-11-18(15)21-20)27-13-5-4-8-19-22-23-24-25(19)16-6-2-1-3-7-16/h10-11,14,16H,1-9,12-13H2,(H,21,26)

> <INCHI_KEY>
RRGUKTPIGVIEKM-UHFFFAOYSA-N

> <FORMULA>
C20H27N5O2

> <MOLECULAR_WEIGHT>
369.4607

> <EXACT_MASS>
369.216475133

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
41.145193045735425

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-[4-(1-cyclohexyl-1H-1,2,3,4-tetrazol-5-yl)butoxy]-1,2,3,4-tetrahydroquinolin-2-one

> <ALOGPS_LOGP>
3.38

> <JCHEM_LOGP>
3.3055661830000007

> <ALOGPS_LOGS>
-4.06

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.416320514141503

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5136977923869409

> <JCHEM_POLAR_SURFACE_AREA>
81.93

> <JCHEM_REFRACTIVITY>
117.13489999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.24e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cilostazol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015297
     RDKit          3D
Cilostazol
 54 57  0  0  0  0  0  0  0  0999 V2000
    9.6717    0.4699   -0.5152 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4986    0.2232   -0.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9119    0.7664    1.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5874    1.4007    0.7659 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7542    0.5151   -0.0752 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3786    0.6676   -0.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5606   -0.1364   -0.8081 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1861    0.0335   -0.7576 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5788    1.0246    0.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0674    0.8772   -0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2858   -0.5146    0.2358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7337   -0.8639    0.0769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6362   -0.0164    0.8862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2456    0.9622    1.7002 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3239    1.4822    2.2408 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3778    0.8417    1.7751 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9680   -0.0857    0.9381 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8355   -0.9852    0.2325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9877   -0.5324   -1.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4089   -0.2527   -1.5823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0167    0.6373   -0.5200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0889   -0.0489    0.8185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1455   -1.2118    0.9362 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0589   -1.1116   -1.6321 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4419   -1.2568   -1.6602 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2684   -0.4582   -0.8964 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6932   -0.6196   -0.9359 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5477    1.5717    1.5454 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7135   -0.0404    1.8484 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7357    2.3817    0.2732 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0851    1.6335    1.7487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9669    1.4268    0.5996 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7332    0.8127    1.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9106    2.0386   -0.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4914    1.6821    0.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0423    1.0270   -1.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3822   -1.2010   -0.3209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0355   -0.7086    1.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9621   -0.7926   -1.0146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9471   -1.9141    0.3615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3138   -1.9829    0.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3534    0.3733   -1.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6000   -1.2957   -1.9191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9333   -1.2139   -1.6566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4170    0.2826   -2.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3517    1.5262   -0.4386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0182    0.9433   -0.8899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1210   -0.4387    0.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9271    0.6833    1.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6169   -2.1548    0.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9166   -1.3445    2.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3993   -1.7364   -2.2307 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8849   -2.0054   -2.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0845   -1.3611   -1.5615 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  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
  7 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27  2  1  0
 26  5  1  0
 17 13  1  0
 23 18  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  6 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
 21 47  1  0
 22 48  1  0
 22 49  1  0
 23 50  1  0
 23 51  1  0
 24 52  1  0
 25 53  1  0
 27 54  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1166                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      11.184  -0.169   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.080  -3.286   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      19.260  -0.282   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      20.294  -1.422   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      18.022  -2.444   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      19.529  -2.759   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       5.747  -3.286   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      19.574   1.226   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.425   2.252   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.037   1.708   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.740   3.760   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.351   3.215   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      20.203   4.241   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.855  -0.913   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.519  -0.149   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.188  -0.924   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.851  -0.159   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.520  -0.934   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.081  -0.976   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.747  -0.206   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.081  -2.516   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.414  -0.976   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.853  -0.944   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.458  -0.153   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.414  -2.516   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.458  -3.340   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.853  -2.548   0.000  0.00  0.00           C+0
CONECT    1   18   23                                                       
CONECT    2   25                                                            
CONECT    3    4    8   14                                                  
CONECT    4    3    6                                                       
CONECT    5    6   14                                                       
CONECT    6    4    5                                                       
CONECT    7   21   25                                                       
CONECT    8    3    9   10                                                  
CONECT    9    8   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   13                                                       
CONECT   13   11   12                                                       
CONECT   14    3    5   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18    1   17                                                       
CONECT   19   20   21   24                                                  
CONECT   20   19   22                                                       
CONECT   21    7   19   26                                                  
CONECT   22   20   25                                                       
CONECT   23    1   24   27                                                  
CONECT   24   19   23                                                       
CONECT   25    2    7   22                                                  
CONECT   26   21   27                                                       
CONECT   27   23   26                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

COMPND    HMDB0015297
HETATM    1  O1  UNL     1       9.672   0.470  -0.515  1.00  0.00           O  
HETATM    2  C1  UNL     1       8.499   0.223  -0.135  1.00  0.00           C  
HETATM    3  C2  UNL     1       7.912   0.766   1.108  1.00  0.00           C  
HETATM    4  C3  UNL     1       6.587   1.401   0.766  1.00  0.00           C  
HETATM    5  C4  UNL     1       5.754   0.515  -0.075  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.379   0.668  -0.040  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.561  -0.136  -0.808  1.00  0.00           C  
HETATM    8  O2  UNL     1       2.186   0.034  -0.758  1.00  0.00           O  
HETATM    9  C7  UNL     1       1.579   1.025   0.072  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.067   0.877  -0.167  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.286  -0.515   0.236  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.734  -0.864   0.077  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.636  -0.016   0.886  1.00  0.00           C  
HETATM   14  N1  UNL     1      -2.246   0.962   1.700  1.00  0.00           N  
HETATM   15  N2  UNL     1      -3.324   1.482   2.241  1.00  0.00           N  
HETATM   16  N3  UNL     1      -4.378   0.842   1.775  1.00  0.00           N  
HETATM   17  N4  UNL     1      -3.968  -0.086   0.938  1.00  0.00           N  
HETATM   18  C12 UNL     1      -4.835  -0.985   0.233  1.00  0.00           C  
HETATM   19  C13 UNL     1      -4.988  -0.532  -1.182  1.00  0.00           C  
HETATM   20  C14 UNL     1      -6.409  -0.253  -1.582  1.00  0.00           C  
HETATM   21  C15 UNL     1      -7.017   0.637  -0.520  1.00  0.00           C  
HETATM   22  C16 UNL     1      -7.089  -0.049   0.818  1.00  0.00           C  
HETATM   23  C17 UNL     1      -6.146  -1.212   0.936  1.00  0.00           C  
HETATM   24  C18 UNL     1       4.059  -1.112  -1.632  1.00  0.00           C  
HETATM   25  C19 UNL     1       5.442  -1.257  -1.660  1.00  0.00           C  
HETATM   26  C20 UNL     1       6.268  -0.458  -0.896  1.00  0.00           C  
HETATM   27  N5  UNL     1       7.693  -0.620  -0.936  1.00  0.00           N  
HETATM   28  H1  UNL     1       8.548   1.572   1.545  1.00  0.00           H  
HETATM   29  H2  UNL     1       7.713  -0.040   1.848  1.00  0.00           H  
HETATM   30  H3  UNL     1       6.736   2.382   0.273  1.00  0.00           H  
HETATM   31  H4  UNL     1       6.085   1.633   1.749  1.00  0.00           H  
HETATM   32  H5  UNL     1       3.967   1.427   0.600  1.00  0.00           H  
HETATM   33  H6  UNL     1       1.733   0.813   1.149  1.00  0.00           H  
HETATM   34  H7  UNL     1       1.911   2.039  -0.195  1.00  0.00           H  
HETATM   35  H8  UNL     1      -0.491   1.682   0.303  1.00  0.00           H  
HETATM   36  H9  UNL     1      -0.042   1.027  -1.274  1.00  0.00           H  
HETATM   37  H10 UNL     1       0.382  -1.201  -0.321  1.00  0.00           H  
HETATM   38  H11 UNL     1      -0.036  -0.709   1.319  1.00  0.00           H  
HETATM   39  H12 UNL     1      -1.962  -0.793  -1.015  1.00  0.00           H  
HETATM   40  H13 UNL     1      -1.947  -1.914   0.362  1.00  0.00           H  
HETATM   41  H14 UNL     1      -4.314  -1.983   0.209  1.00  0.00           H  
HETATM   42  H15 UNL     1      -4.353   0.373  -1.377  1.00  0.00           H  
HETATM   43  H16 UNL     1      -4.600  -1.296  -1.919  1.00  0.00           H  
HETATM   44  H17 UNL     1      -6.933  -1.214  -1.657  1.00  0.00           H  
HETATM   45  H18 UNL     1      -6.417   0.283  -2.537  1.00  0.00           H  
HETATM   46  H19 UNL     1      -6.352   1.526  -0.439  1.00  0.00           H  
HETATM   47  H20 UNL     1      -8.018   0.943  -0.890  1.00  0.00           H  
HETATM   48  H21 UNL     1      -8.121  -0.439   0.938  1.00  0.00           H  
HETATM   49  H22 UNL     1      -6.927   0.683   1.636  1.00  0.00           H  
HETATM   50  H23 UNL     1      -6.617  -2.155   0.593  1.00  0.00           H  
HETATM   51  H24 UNL     1      -5.917  -1.345   2.017  1.00  0.00           H  
HETATM   52  H25 UNL     1       3.399  -1.736  -2.231  1.00  0.00           H  
HETATM   53  H26 UNL     1       5.885  -2.005  -2.288  1.00  0.00           H  
HETATM   54  H27 UNL     1       8.084  -1.361  -1.561  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   27
CONECT    3    4   28   29
CONECT    4    5   30   31
CONECT    5    6    6   26
CONECT    6    7   32
CONECT    7    8   24   24
CONECT    8    9
CONECT    9   10   33   34
CONECT   10   11   35   36
CONECT   11   12   37   38
CONECT   12   13   39   40
CONECT   13   14   14   17
CONECT   14   15
CONECT   15   16   16
CONECT   16   17
CONECT   17   18
CONECT   18   19   23   41
CONECT   19   20   42   43
CONECT   20   21   44   45
CONECT   21   22   46   47
CONECT   22   23   48   49
CONECT   23   50   51
CONECT   24   25   52
CONECT   25   26   26   53
CONECT   26   27
CONECT   27   54
END

HMDB0015297
     RDKit          3D
Cilostazol
 54 57  0  0  0  0  0  0  0  0999 V2000
    9.6717    0.4699   -0.5152 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4986    0.2232   -0.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9119    0.7664    1.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5874    1.4007    0.7659 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7542    0.5151   -0.0752 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3786    0.6676   -0.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5606   -0.1364   -0.8081 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1861    0.0335   -0.7576 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5788    1.0246    0.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0674    0.8772   -0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2858   -0.5146    0.2358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7337   -0.8639    0.0769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6362   -0.0164    0.8862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2456    0.9622    1.7002 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3239    1.4822    2.2408 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3778    0.8417    1.7751 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9680   -0.0857    0.9381 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8355   -0.9852    0.2325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9877   -0.5324   -1.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4089   -0.2527   -1.5823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0167    0.6373   -0.5200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0889   -0.0489    0.8185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1455   -1.2118    0.9362 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0589   -1.1116   -1.6321 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4419   -1.2568   -1.6602 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2684   -0.4582   -0.8964 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6932   -0.6196   -0.9359 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5477    1.5717    1.5454 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7135   -0.0404    1.8484 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7357    2.3817    0.2732 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0851    1.6335    1.7487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9669    1.4268    0.5996 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7332    0.8127    1.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9106    2.0386   -0.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4914    1.6821    0.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0423    1.0270   -1.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3822   -1.2010   -0.3209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0355   -0.7086    1.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9621   -0.7926   -1.0146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9471   -1.9141    0.3615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3138   -1.9829    0.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3534    0.3733   -1.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6000   -1.2957   -1.9191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9333   -1.2139   -1.6566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4170    0.2826   -2.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3517    1.5262   -0.4386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0182    0.9433   -0.8899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1210   -0.4387    0.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9271    0.6833    1.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6169   -2.1548    0.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9166   -1.3445    2.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3993   -1.7364   -2.2307 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8849   -2.0054   -2.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0845   -1.3611   -1.5615 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  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
  7 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27  2  1  0
 26  5  1  0
 17 13  1  0
 23 18  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  6 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
 21 47  1  0
 22 48  1  0
 22 49  1  0
 23 50  1  0
 23 51  1  0
 24 52  1  0
 25 53  1  0
 27 54  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,4-Dihydro-6-(4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy)-2(1H)-quinolinone	ChEBI
6-(4-(1-Cyclohexyl-1H-tetrazol-5-yl)butoxy)-3,4-dihydro-2(1H)-quinolinone	ChEBI
6-(4-(1-Cyclohexyl-1H-tetrazol-5-yl)butoxy)-3,4-dihydrocarbostyril	ChEBI
6-[4-(1-Cyclohexyl-1H-tetrazol-5-yl)-butoxy]-3,4-dihydro-1H-quinolin-2-one	ChEBI
Cilostazolum	ChEBI
Pletal	Kegg
Cilostazole	HMDB

Chemical Formula

C₂₀H₂₇N₅O₂

Average Molecular Weight

369.4607

Monoisotopic Molecular Weight

369.216475133

IUPAC Name

6-[4-(1-cyclohexyl-1H-1,2,3,4-tetrazol-5-yl)butoxy]-1,2,3,4-tetrahydroquinolin-2-one

Traditional Name

cilostazol

CAS Registry Number

73963-72-1

SMILES

O=C1CCC2=C(N1)C=CC(OCCCCC1=NN=NN1C1CCCCC1)=C2

InChI Identifier

InChI=1S/C20H27N5O2/c26-20-12-9-15-14-17(10-11-18(15)21-20)27-13-5-4-8-19-22-23-24-25(19)16-6-2-1-3-7-16/h10-11,14,16H,1-9,12-13H2,(H,21,26)

InChI Key

RRGUKTPIGVIEKM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinolones and derivatives

Direct Parent

Hydroquinolones

Alternative Parents

Substituents

Tetrahydroquinolone
Tetrahydroquinoline
Alkyl aryl ether
Benzenoid
Azole
Heteroaromatic compound
Tetrazole
Carboxamide group
Lactam
Secondary carboxylic acid amide
Carboxylic acid derivative
Ether
Azacycle
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tetrazoles (CHEBI:31401 )
lactam (CHEBI:31401 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015297)

Source

Exogenous

Exogenous (HMDB: HMDB0015297)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Cilostazol Action Pathway (PathBank: SMP0000263)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	160 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.032 g/L	Not Available
LogP	2.3	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.032 g/L	ALOGPS
logP	3.38	ALOGPS
logP	3.31	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	14.42	ChemAxon
pKa (Strongest Basic)	-0.51	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	81.93 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	117.13 m³·mol⁻¹	ChemAxon
Polarizability	41.15 Å³	ChemAxon
Number of Rings	4	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
DarkChem	[M+H]+	186.608	31661259
DarkChem	[M-H]-	184.074	31661259
DeepCCS	[M+H]+	188.498	30932474
DeepCCS	[M-H]-	186.14	30932474
DeepCCS	[M-2H]-	219.152	30932474
DeepCCS	[M+Na]+	194.591	30932474
AllCCS	[M+H]+	191.0	32859911
AllCCS	[M+H-H2O]+	188.5	32859911
AllCCS	[M+NH4]+	193.3	32859911
AllCCS	[M+Na]+	194.0	32859911
AllCCS	[M-H]-	187.8	32859911
AllCCS	[M+Na-2H]-	188.1	32859911
AllCCS	[M+HCOO]-	188.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.83 minutes	32390414
Predicted by Siyang on May 30, 2022	14.6053 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.93 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	38.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2654.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	259.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	193.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	174.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	242.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	554.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	634.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	130.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1321.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	489.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1514.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	408.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	404.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	303.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	200.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	83.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cilostazol	O=C1CCC2=C(N1)C=CC(OCCCCC1=NN=NN1C1CCCCC1)=C2	4079.7	Standard polar	33892256
Cilostazol	O=C1CCC2=C(N1)C=CC(OCCCCC1=NN=NN1C1CCCCC1)=C2	3418.4	Standard non polar	33892256
Cilostazol	O=C1CCC2=C(N1)C=CC(OCCCCC1=NN=NN1C1CCCCC1)=C2	3674.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cilostazol,1TMS,isomer #1	C[Si](C)(C)N1C(=O)CCC2=CC(OCCCCC3=NN=NN3C3CCCCC3)=CC=C21	3478.0	Semi standard non polar	33892256
Cilostazol,1TMS,isomer #1	C[Si](C)(C)N1C(=O)CCC2=CC(OCCCCC3=NN=NN3C3CCCCC3)=CC=C21	3295.5	Standard non polar	33892256
Cilostazol,1TMS,isomer #1	C[Si](C)(C)N1C(=O)CCC2=CC(OCCCCC3=NN=NN3C3CCCCC3)=CC=C21	4513.0	Standard polar	33892256
Cilostazol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)CCC2=CC(OCCCCC3=NN=NN3C3CCCCC3)=CC=C21	3695.2	Semi standard non polar	33892256
Cilostazol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)CCC2=CC(OCCCCC3=NN=NN3C3CCCCC3)=CC=C21	3516.0	Standard non polar	33892256
Cilostazol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)CCC2=CC(OCCCCC3=NN=NN3C3CCCCC3)=CC=C21	4583.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cilostazol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fal-8947000000-2a45c02fa8163a7e214e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cilostazol 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 - Cilostazol LC-ESI-qTof , Positive-QTOF	splash10-0fc3-2900000000-aeed8cd6efbb3b93af8e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cilostazol , positive-QTOF	splash10-00dr-1698000000-05ddf5c1a046516bae11	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cilostazol , positive-QTOF	splash10-01t9-3920000000-86a7d65313952e9a8d3f	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cilostazol 10V, Positive-QTOF	splash10-00di-0129000000-f672b81f1eae1e02bf26	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cilostazol 20V, Positive-QTOF	splash10-06za-7679000000-3558d68d922f50a245e5	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cilostazol 40V, Positive-QTOF	splash10-001i-9600000000-a29f6d9a47bb72fd9433	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cilostazol 10V, Negative-QTOF	splash10-014i-0529000000-1054f4f0e8e908b32dc8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cilostazol 20V, Negative-QTOF	splash10-03di-2913000000-c486550cc7475c61e6e3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cilostazol 40V, Negative-QTOF	splash10-01ox-5900000000-285688ae4185c24bab91	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cilostazol 10V, Positive-QTOF	splash10-00di-0029000000-dcfc288c1d5ecab73a27	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cilostazol 20V, Positive-QTOF	splash10-0089-9018000000-77173424302a7aea56fe	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cilostazol 40V, Positive-QTOF	splash10-004i-0970000000-ddeea9f213a26978e589	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cilostazol 10V, Negative-QTOF	splash10-014i-0109000000-55bee19f6f547c13b3b2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cilostazol 20V, Negative-QTOF	splash10-014i-0109000000-ad4dbc3d4880ce468bb5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cilostazol 40V, Negative-QTOF	splash10-03di-1921000000-c6d1a1ca29c9d4653634	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Cilostazol Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01166	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01166	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01166

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2652

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cilostazol

METLIN ID

Not Available

PubChem Compound

2754

PDB ID

Not Available

ChEBI ID

31401

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. cGMP-inhibited 3',5'-cyclic phosphodiesterase A

General function:: Involved in catalytic activity
Specific function:: Cyclic nucleotide phosphodiesterase with a dual-specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes (By similarity).
Gene Name:: PDE3A
Uniprot ID:: Q14432
Molecular weight:: 124978.06

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Hong KW, Lee JH, Kima KY, Park SY, Lee WS: Cilostazol: therapeutic potential against focal cerebral ischemic damage. Curr Pharm Des. 2006;12(5):565-73. [PubMed:16472148 ]
Schror K: The pharmacology of cilostazol. Diabetes Obes Metab. 2002 Mar;4 Suppl 2:S14-9. [PubMed:12180353 ]
Mokry J, Mokra D, Nosalova G, Beharkova M, Feherova Z: Influence of selective inhibitors of phosphodiesterase 3 and 4 on cough and airway reactivity. J Physiol Pharmacol. 2008 Dec;59 Suppl 6:473-82. [PubMed:19218671 ]
Parkkonen J, Hasala H, Moilanen E, Giembycz MA, Kankaanranta H: Phosphodiesterase 4 inhibitors delay human eosinophil and neutrophil apoptosis in the absence and presence of salbutamol. Pulm Pharmacol Ther. 2008;21(3):499-506. doi: 10.1016/j.pupt.2007.11.003. Epub 2007 Nov 22. [PubMed:18282775 ]

Enzyme Details

2. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Suri A, Forbes WP, Bramer SL: Effects of CYP3A inhibition on the metabolism of cilostazol. Clin Pharmacokinet. 1999;37 Suppl 2:61-8. [PubMed:10702888 ]

Enzyme Details

3. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

Suri A, Forbes WP, Bramer SL: Effects of CYP3A inhibition on the metabolism of cilostazol. Clin Pharmacokinet. 1999;37 Suppl 2:61-8. [PubMed:10702888 ]

Enzyme Details

4. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Suri A, Forbes WP, Bramer SL: Effects of CYP3A inhibition on the metabolism of cilostazol. Clin Pharmacokinet. 1999;37 Suppl 2:61-8. [PubMed:10702888 ]

Enzyme Details

5. Cytochrome P450 3A5

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

References

Suri A, Forbes WP, Bramer SL: Effects of CYP3A inhibition on the metabolism of cilostazol. Clin Pharmacokinet. 1999;37 Suppl 2:61-8. [PubMed:10702888 ]

Enzyme Details

6. Cytochrome P450 3A7

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A7
Uniprot ID:: P24462
Molecular weight:: 57525.03

References

Suri A, Forbes WP, Bramer SL: Effects of CYP3A inhibition on the metabolism of cilostazol. Clin Pharmacokinet. 1999;37 Suppl 2:61-8. [PubMed:10702888 ]

Enzyme Details

7. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Suri A, Forbes WP, Bramer SL: Effects of CYP3A inhibition on the metabolism of cilostazol. Clin Pharmacokinet. 1999;37 Suppl 2:61-8. [PubMed:10702888 ]

Showing metabocard for Cilostazol (HMDB0015297)

MOL for HMDB0015297 (Cilostazol)

3D MOL for HMDB0015297 (Cilostazol)

3D SDF for HMDB0015297 (Cilostazol)

3D-SDF for HMDB0015297 (Cilostazol)

PDB for HMDB0015297 (Cilostazol)

3D PDB for HMDB0015297 (Cilostazol)

SMILES for HMDB0015297 (Cilostazol)

INCHI for HMDB0015297 (Cilostazol)

Structure for HMDB0015297 (Cilostazol)

3D Structure for HMDB0015297 (Cilostazol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

References