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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:47 UTC

HMDB ID

HMDB0014913

Secondary Accession Numbers

HMDB14913

Metabolite Identification

Common Name

Tirofiban

Description

Tirofiban, also known as agrastat, belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Tirofiban is a drug which is used for treatment, in combination with heparin, of acute coronary syndrome, including patients who are to be managed medically and those undergoing ptca or atherectomy. In humans, tirofiban is involved in the tirofiban action pathway. Tirofiban is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Tirofiban.

Structure

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

775
  Mrv0541 02231214592D          

 30 31  0  0  1  0            999 V2000
    7.0944    3.3001    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5069    2.5856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6819    4.0145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8089    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -5.3626    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799    2.8876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -4.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -5.3626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -4.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -4.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -5.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -4.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -3.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6655    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8089    3.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8089    4.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5234    4.9501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5234    5.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  2  0  0  0  0
  1  4  2  0  0  0  0
  1  8  1  0  0  0  0
  1 20  1  0  0  0  0
  2 17  1  0  0  0  0
  2 21  1  0  0  0  0
  5 29  1  0  0  0  0
  6 29  2  0  0  0  0
  7 13  1  0  0  0  0
  7 14  1  0  0  0  0
 18  8  1  6  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 10 13  1  0  0  0  0
 11 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 19  1  0  0  0  0
 18 29  1  0  0  0  0
 19 23  1  0  0  0  0
 20 22  1  0  0  0  0
 21 25  2  0  0  0  0
 21 26  1  0  0  0  0
 22 24  1  0  0  0  0
 23 27  2  0  0  0  0
 23 28  1  0  0  0  0
 24 30  1  0  0  0  0
 25 27  1  0  0  0  0
 26 28  2  0  0  0  0
M  END

HMDB0014913
     RDKit          3D
Tirofiban
 66 67  0  0  0  0  0  0  0  0999 V2000
    6.5494    1.2333   -0.1610 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1342   -0.0379   -0.7041 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1861   -1.1949    0.1808 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0036   -1.9422    0.6493 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0953   -2.7942   -0.5731 S   0  0  0  0  0  6  0  0  0  0  0  0
    6.1387   -3.6333   -1.3558 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2586   -3.8780    0.1177 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2007   -1.9642   -1.6935 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0721   -1.2085   -1.3264 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2937    0.2800   -1.4556 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0653    1.0387   -1.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2480    1.4837   -2.1536 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0677    2.1562   -1.9037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3273    2.4019   -0.5685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4791    3.0612   -0.3721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1170    3.3950    0.7889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5889    2.1769    1.5375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5633    1.4397    0.6054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0386    0.2201    1.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0242   -0.6103    0.5414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1932    0.2892    0.2370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4245   -0.4564   -0.1696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5393   -1.7902    0.3610 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8704   -1.9166    1.6346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3878   -1.8048    1.3744 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4984    1.9539    0.4114 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7052    1.2665    0.1533 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7979   -1.6755   -1.9187 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7934   -2.6825   -2.7065 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5619   -1.1050   -1.6891 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4042    1.9000    0.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9487    1.0503    0.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9636    1.7741   -0.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4670   -0.3075   -1.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1697    0.1655   -1.1078 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6976   -0.8245    1.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9928   -1.9456   -0.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3604   -1.1980    1.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3614   -2.6944    1.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4102   -2.0688   -2.6909 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280   -1.4136   -0.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7387    0.5997   -2.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0645    0.4920   -0.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4917    1.3267   -3.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5756    2.5065   -2.6910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4107    3.9538    1.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0308    4.0208    0.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8405    1.4937    1.9021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1659    2.5270    2.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3770    2.0868    0.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9807    1.0749   -0.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6011    0.5021    2.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2060   -0.4035    1.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5050   -0.8623   -0.4005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9015    0.9347   -0.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3869    0.9761    1.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5707   -0.4950   -1.2763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2956    0.1441    0.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5467   -2.0556    0.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0882   -2.9504    1.9951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1557   -1.1524    2.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8041   -1.8642    2.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0840   -2.7016    0.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2591    2.1336    1.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2686    0.9620    1.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1156   -1.3887   -1.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  2  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  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
 23 24  1  0
 24 25  1  0
 14 26  1  0
 26 27  2  0
  9 28  1  0
 28 29  2  0
 28 30  1  0
 27 11  1  0
 25 20  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  8 40  1  0
  9 41  1  1
 10 42  1  0
 10 43  1  0
 12 44  1  0
 13 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 18 50  1  0
 18 51  1  0
 19 52  1  0
 19 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 22 57  1  0
 22 58  1  0
 23 59  1  0
 24 60  1  0
 24 61  1  0
 25 62  1  0
 25 63  1  0
 26 64  1  0
 27 65  1  0
 30 66  1  0
M  END

775
  Mrv0541 02231214592D          

 30 31  0  0  1  0            999 V2000
    7.0944    3.3001    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5069    2.5856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6819    4.0145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8089    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -5.3626    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799    2.8876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -4.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -5.3626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -4.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -4.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -5.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -4.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -3.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6655    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8089    3.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8089    4.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5234    4.9501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5234    5.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  2  0  0  0  0
  1  4  2  0  0  0  0
  1  8  1  0  0  0  0
  1 20  1  0  0  0  0
  2 17  1  0  0  0  0
  2 21  1  0  0  0  0
  5 29  1  0  0  0  0
  6 29  2  0  0  0  0
  7 13  1  0  0  0  0
  7 14  1  0  0  0  0
 18  8  1  6  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 10 13  1  0  0  0  0
 11 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 19  1  0  0  0  0
 18 29  1  0  0  0  0
 19 23  1  0  0  0  0
 20 22  1  0  0  0  0
 21 25  2  0  0  0  0
 21 26  1  0  0  0  0
 22 24  1  0  0  0  0
 23 27  2  0  0  0  0
 23 28  1  0  0  0  0
 24 30  1  0  0  0  0
 25 27  1  0  0  0  0
 26 28  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014913

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCS(=O)(=O)N[C@@H](CC1=CC=C(OCCCCC2CCNCC2)C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H36N2O5S/c1-2-3-16-30(27,28)24-21(22(25)26)17-19-7-9-20(10-8-19)29-15-5-4-6-18-11-13-23-14-12-18/h7-10,18,21,23-24H,2-6,11-17H2,1H3,(H,25,26)/t21-/m0/s1

> <INCHI_KEY>
COKMIXFXJJXBQG-NRFANRHFSA-N

> <FORMULA>
C22H36N2O5S

> <MOLECULAR_WEIGHT>
440.597

> <EXACT_MASS>
440.234492962

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
49.27271964129321

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-(butane-1-sulfonamido)-3-{4-[4-(piperidin-4-yl)butoxy]phenyl}propanoic acid

> <ALOGPS_LOGP>
1.78

> <JCHEM_LOGP>
0.5982969923702584

> <ALOGPS_LOGS>
-5.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.894182081926783

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1721346854705534

> <JCHEM_PKA_STRONGEST_BASIC>
10.207444726493483

> <JCHEM_POLAR_SURFACE_AREA>
104.73000000000002

> <JCHEM_REFRACTIVITY>
117.4761

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.17e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tirofiban

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014913
     RDKit          3D
Tirofiban
 66 67  0  0  0  0  0  0  0  0999 V2000
    6.5494    1.2333   -0.1610 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1342   -0.0379   -0.7041 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1861   -1.1949    0.1808 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0036   -1.9422    0.6493 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0953   -2.7942   -0.5731 S   0  0  0  0  0  6  0  0  0  0  0  0
    6.1387   -3.6333   -1.3558 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2586   -3.8780    0.1177 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2007   -1.9642   -1.6935 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0721   -1.2085   -1.3264 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2937    0.2800   -1.4556 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0653    1.0387   -1.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2480    1.4837   -2.1536 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0677    2.1562   -1.9037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3273    2.4019   -0.5685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4791    3.0612   -0.3721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1170    3.3950    0.7889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5889    2.1769    1.5375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5633    1.4397    0.6054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0386    0.2201    1.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0242   -0.6103    0.5414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1932    0.2892    0.2370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4245   -0.4564   -0.1696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5393   -1.7902    0.3610 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8704   -1.9166    1.6346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3878   -1.8048    1.3744 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4984    1.9539    0.4114 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7052    1.2665    0.1533 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7979   -1.6755   -1.9187 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7934   -2.6825   -2.7065 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5619   -1.1050   -1.6891 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4042    1.9000    0.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9487    1.0503    0.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9636    1.7741   -0.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4670   -0.3075   -1.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1697    0.1655   -1.1078 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6976   -0.8245    1.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9928   -1.9456   -0.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3604   -1.1980    1.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3614   -2.6944    1.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4102   -2.0688   -2.6909 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280   -1.4136   -0.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7387    0.5997   -2.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0645    0.4920   -0.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4917    1.3267   -3.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5756    2.5065   -2.6910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4107    3.9538    1.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0308    4.0208    0.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8405    1.4937    1.9021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1659    2.5270    2.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3770    2.0868    0.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9807    1.0749   -0.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6011    0.5021    2.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2060   -0.4035    1.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5050   -0.8623   -0.4005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9015    0.9347   -0.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3869    0.9761    1.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5707   -0.4950   -1.2763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2956    0.1441    0.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5467   -2.0556    0.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0882   -2.9504    1.9951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1557   -1.1524    2.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8041   -1.8642    2.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0840   -2.7016    0.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2591    2.1336    1.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2686    0.9620    1.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1156   -1.3887   -1.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  2  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  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
 23 24  1  0
 24 25  1  0
 14 26  1  0
 26 27  2  0
  9 28  1  0
 28 29  2  0
 28 30  1  0
 27 11  1  0
 25 20  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  8 40  1  0
  9 41  1  1
 10 42  1  0
 10 43  1  0
 12 44  1  0
 13 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 18 50  1  0
 18 51  1  0
 19 52  1  0
 19 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 22 57  1  0
 22 58  1  0
 23 59  1  0
 24 60  1  0
 24 61  1  0
 25 62  1  0
 25 63  1  0
 26 64  1  0
 27 65  1  0
 30 66  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 775                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      13.243   6.160   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0      10.576  -3.080   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      14.013   4.826   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      12.473   7.494   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      14.577   3.850   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      13.243   1.540   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       3.907 -10.010   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      11.909   5.390   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       6.574  -8.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.574 -10.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.241  -7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.908  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.241 -10.780   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.907  -8.470   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.908  -6.160   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.242  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.242  -3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.909   3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.576   3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.577   6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.576  -1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.577   8.470   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.576   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.910   9.240   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.909  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.242  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.909   0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.242   0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.243   3.080   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      15.910  10.780   0.000  0.00  0.00           C+0
CONECT    1    3    4    8   20                                             
CONECT    2   17   21                                                       
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5   29                                                            
CONECT    6   29                                                            
CONECT    7   13   14                                                       
CONECT    8    1   18                                                       
CONECT    9   10   11   12                                                  
CONECT   10    9   13                                                       
CONECT   11    9   14                                                       
CONECT   12    9   15                                                       
CONECT   13    7   10                                                       
CONECT   14    7   11                                                       
CONECT   15   12   16                                                       
CONECT   16   15   17                                                       
CONECT   17    2   16                                                       
CONECT   18    8   19   29                                                  
CONECT   19   18   23                                                       
CONECT   20    1   22                                                       
CONECT   21    2   25   26                                                  
CONECT   22   20   24                                                       
CONECT   23   19   27   28                                                  
CONECT   24   22   30                                                       
CONECT   25   21   27                                                       
CONECT   26   21   28                                                       
CONECT   27   23   25                                                       
CONECT   28   23   26                                                       
CONECT   29    5    6   18                                                  
CONECT   30   24                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

COMPND    HMDB0014913
HETATM    1  C1  UNL     1       6.549   1.233  -0.161  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.134  -0.038  -0.704  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.186  -1.195   0.181  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.004  -1.942   0.649  1.00  0.00           C  
HETATM    5  S1  UNL     1       5.095  -2.794  -0.573  1.00  0.00           S  
HETATM    6  O1  UNL     1       6.139  -3.633  -1.356  1.00  0.00           O  
HETATM    7  O2  UNL     1       4.259  -3.878   0.118  1.00  0.00           O  
HETATM    8  N1  UNL     1       4.201  -1.964  -1.694  1.00  0.00           N  
HETATM    9  C5  UNL     1       3.072  -1.209  -1.326  1.00  0.00           C  
HETATM   10  C6  UNL     1       3.294   0.280  -1.456  1.00  0.00           C  
HETATM   11  C7  UNL     1       2.065   1.039  -1.148  1.00  0.00           C  
HETATM   12  C8  UNL     1       1.248   1.484  -2.154  1.00  0.00           C  
HETATM   13  C9  UNL     1       0.068   2.156  -1.904  1.00  0.00           C  
HETATM   14  C10 UNL     1      -0.327   2.402  -0.568  1.00  0.00           C  
HETATM   15  O3  UNL     1      -1.479   3.061  -0.372  1.00  0.00           O  
HETATM   16  C11 UNL     1      -2.117   3.395   0.789  1.00  0.00           C  
HETATM   17  C12 UNL     1      -2.589   2.177   1.537  1.00  0.00           C  
HETATM   18  C13 UNL     1      -3.563   1.440   0.605  1.00  0.00           C  
HETATM   19  C14 UNL     1      -4.039   0.220   1.362  1.00  0.00           C  
HETATM   20  C15 UNL     1      -5.024  -0.610   0.541  1.00  0.00           C  
HETATM   21  C16 UNL     1      -6.193   0.289   0.237  1.00  0.00           C  
HETATM   22  C17 UNL     1      -7.424  -0.456  -0.170  1.00  0.00           C  
HETATM   23  N2  UNL     1      -7.539  -1.790   0.361  1.00  0.00           N  
HETATM   24  C18 UNL     1      -6.870  -1.917   1.635  1.00  0.00           C  
HETATM   25  C19 UNL     1      -5.388  -1.805   1.374  1.00  0.00           C  
HETATM   26  C20 UNL     1       0.498   1.954   0.411  1.00  0.00           C  
HETATM   27  C21 UNL     1       1.705   1.267   0.153  1.00  0.00           C  
HETATM   28  C22 UNL     1       1.798  -1.675  -1.919  1.00  0.00           C  
HETATM   29  O4  UNL     1       1.793  -2.682  -2.707  1.00  0.00           O  
HETATM   30  O5  UNL     1       0.562  -1.105  -1.689  1.00  0.00           O  
HETATM   31  H1  UNL     1       7.404   1.900   0.163  1.00  0.00           H  
HETATM   32  H2  UNL     1       5.949   1.050   0.732  1.00  0.00           H  
HETATM   33  H3  UNL     1       5.964   1.774  -0.961  1.00  0.00           H  
HETATM   34  H4  UNL     1       6.467  -0.308  -1.585  1.00  0.00           H  
HETATM   35  H5  UNL     1       8.170   0.165  -1.108  1.00  0.00           H  
HETATM   36  H6  UNL     1       7.698  -0.825   1.155  1.00  0.00           H  
HETATM   37  H7  UNL     1       7.993  -1.946  -0.161  1.00  0.00           H  
HETATM   38  H8  UNL     1       5.360  -1.198   1.220  1.00  0.00           H  
HETATM   39  H9  UNL     1       6.361  -2.694   1.399  1.00  0.00           H  
HETATM   40  H10 UNL     1       4.410  -2.069  -2.691  1.00  0.00           H  
HETATM   41  H11 UNL     1       2.928  -1.414  -0.188  1.00  0.00           H  
HETATM   42  H12 UNL     1       3.739   0.600  -2.399  1.00  0.00           H  
HETATM   43  H13 UNL     1       4.065   0.492  -0.648  1.00  0.00           H  
HETATM   44  H14 UNL     1       1.492   1.327  -3.213  1.00  0.00           H  
HETATM   45  H15 UNL     1      -0.576   2.506  -2.691  1.00  0.00           H  
HETATM   46  H16 UNL     1      -1.411   3.954   1.470  1.00  0.00           H  
HETATM   47  H17 UNL     1      -3.031   4.021   0.609  1.00  0.00           H  
HETATM   48  H18 UNL     1      -1.841   1.494   1.902  1.00  0.00           H  
HETATM   49  H19 UNL     1      -3.166   2.527   2.441  1.00  0.00           H  
HETATM   50  H20 UNL     1      -4.377   2.087   0.285  1.00  0.00           H  
HETATM   51  H21 UNL     1      -2.981   1.075  -0.262  1.00  0.00           H  
HETATM   52  H22 UNL     1      -4.601   0.502   2.281  1.00  0.00           H  
HETATM   53  H23 UNL     1      -3.206  -0.404   1.685  1.00  0.00           H  
HETATM   54  H24 UNL     1      -4.505  -0.862  -0.400  1.00  0.00           H  
HETATM   55  H25 UNL     1      -5.902   0.935  -0.619  1.00  0.00           H  
HETATM   56  H26 UNL     1      -6.387   0.976   1.087  1.00  0.00           H  
HETATM   57  H27 UNL     1      -7.571  -0.495  -1.276  1.00  0.00           H  
HETATM   58  H28 UNL     1      -8.296   0.144   0.218  1.00  0.00           H  
HETATM   59  H29 UNL     1      -8.547  -2.056   0.395  1.00  0.00           H  
HETATM   60  H30 UNL     1      -7.088  -2.950   1.995  1.00  0.00           H  
HETATM   61  H31 UNL     1      -7.156  -1.152   2.359  1.00  0.00           H  
HETATM   62  H32 UNL     1      -4.804  -1.864   2.334  1.00  0.00           H  
HETATM   63  H33 UNL     1      -5.084  -2.702   0.797  1.00  0.00           H  
HETATM   64  H34 UNL     1       0.259   2.134   1.454  1.00  0.00           H  
HETATM   65  H35 UNL     1       2.269   0.962   1.019  1.00  0.00           H  
HETATM   66  H36 UNL     1      -0.116  -1.389  -1.016  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3   34   35
CONECT    3    4   36   37
CONECT    4    5   38   39
CONECT    5    6    6    7    7
CONECT    5    8
CONECT    8    9   40
CONECT    9   10   28   41
CONECT   10   11   42   43
CONECT   11   12   12   27
CONECT   12   13   44
CONECT   13   14   14   45
CONECT   14   15   26
CONECT   15   16
CONECT   16   17   46   47
CONECT   17   18   48   49
CONECT   18   19   50   51
CONECT   19   20   52   53
CONECT   20   21   25   54
CONECT   21   22   55   56
CONECT   22   23   57   58
CONECT   23   24   59
CONECT   24   25   60   61
CONECT   25   62   63
CONECT   26   27   27   64
CONECT   27   65
CONECT   28   29   29   30
CONECT   30   66
END

HMDB0014913
     RDKit          3D
Tirofiban
 66 67  0  0  0  0  0  0  0  0999 V2000
    6.5494    1.2333   -0.1610 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1342   -0.0379   -0.7041 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1861   -1.1949    0.1808 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0036   -1.9422    0.6493 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0953   -2.7942   -0.5731 S   0  0  0  0  0  6  0  0  0  0  0  0
    6.1387   -3.6333   -1.3558 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2586   -3.8780    0.1177 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2007   -1.9642   -1.6935 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0721   -1.2085   -1.3264 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2937    0.2800   -1.4556 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0653    1.0387   -1.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2480    1.4837   -2.1536 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0677    2.1562   -1.9037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3273    2.4019   -0.5685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4791    3.0612   -0.3721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1170    3.3950    0.7889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5889    2.1769    1.5375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5633    1.4397    0.6054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0386    0.2201    1.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0242   -0.6103    0.5414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1932    0.2892    0.2370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4245   -0.4564   -0.1696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5393   -1.7902    0.3610 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8704   -1.9166    1.6346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3878   -1.8048    1.3744 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4984    1.9539    0.4114 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7052    1.2665    0.1533 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7979   -1.6755   -1.9187 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7934   -2.6825   -2.7065 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5619   -1.1050   -1.6891 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4042    1.9000    0.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9487    1.0503    0.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9636    1.7741   -0.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4670   -0.3075   -1.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1697    0.1655   -1.1078 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6976   -0.8245    1.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9928   -1.9456   -0.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3604   -1.1980    1.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3614   -2.6944    1.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4102   -2.0688   -2.6909 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280   -1.4136   -0.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7387    0.5997   -2.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0645    0.4920   -0.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4917    1.3267   -3.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5756    2.5065   -2.6910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4107    3.9538    1.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0308    4.0208    0.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8405    1.4937    1.9021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1659    2.5270    2.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3770    2.0868    0.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9807    1.0749   -0.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6011    0.5021    2.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2060   -0.4035    1.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5050   -0.8623   -0.4005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9015    0.9347   -0.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3869    0.9761    1.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5707   -0.4950   -1.2763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2956    0.1441    0.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5467   -2.0556    0.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0882   -2.9504    1.9951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1557   -1.1524    2.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8041   -1.8642    2.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0840   -2.7016    0.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2591    2.1336    1.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2686    0.9620    1.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1156   -1.3887   -1.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  2  0
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  8  9  1  0
  9 10  1  0
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  9 28  1  0
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 30 66  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2S)-2-(Butylsulfonylamino)-3-[4-(4-piperidin-4-ylbutoxy)phenyl]propanoic acid	ChEBI
N-(Butylsulfonyl)-O-(4-(4-piperidyl)butyl)-L-tyrosine	ChEBI
Tirofibanum	ChEBI
Agrastat	Kegg
(2S)-2-(Butylsulfonylamino)-3-[4-(4-piperidin-4-ylbutoxy)phenyl]propanoate	Generator
(2S)-2-(Butylsulphonylamino)-3-[4-(4-piperidin-4-ylbutoxy)phenyl]propanoate	Generator
(2S)-2-(Butylsulphonylamino)-3-[4-(4-piperidin-4-ylbutoxy)phenyl]propanoic acid	Generator
N-(Butylsulphonyl)-O-(4-(4-piperidyl)butyl)-L-tyrosine	Generator
Merck sharp and dohme brand OF tirofiban hydrochloride monohydrate	HMDB
Tirofiban hydrochloride	HMDB
Merck frosst brand OF tirofiban hydrochloride monohydrate	HMDB
Merck brand OF tirofiban hydrochloride monohydrate	HMDB
Tirofiban hydrochloride monohydrate	HMDB
Aggrastat	HMDB
Cahill may roberts brand OF tirofiban hydrochloride monohydrate	HMDB
MSD Brand OF tirofiban hydrochloride monohydrate	HMDB

Chemical Formula

C₂₂H₃₆N₂O₅S

Average Molecular Weight

440.597

Monoisotopic Molecular Weight

440.234492962

IUPAC Name

(2S)-2-(butane-1-sulfonamido)-3-{4-[4-(piperidin-4-yl)butoxy]phenyl}propanoic acid

Traditional Name

tirofiban

CAS Registry Number

144494-65-5

SMILES

CCCCS(=O)(=O)N[C@@H](CC1=CC=C(OCCCCC2CCNCC2)C=C1)C(O)=O

InChI Identifier

InChI=1S/C22H36N2O5S/c1-2-3-16-30(27,28)24-21(22(25)26)17-19-7-9-20(10-8-19)29-15-5-4-6-18-11-13-23-14-12-18/h7-10,18,21,23-24H,2-6,11-17H2,1H3,(H,25,26)/t21-/m0/s1

InChI Key

COKMIXFXJJXBQG-NRFANRHFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Phenylalanine and derivatives

Alternative Parents

Substituents

Phenylalanine or derivatives
3-phenylpropanoic-acid
Amphetamine or derivatives
Phenoxy compound
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Piperidine
Benzenoid
Organosulfonic acid amide
Organic sulfonic acid amide
Organic sulfonic acid or derivatives
Aminosulfonyl compound
Sulfonyl
Organosulfonic acid or derivatives
Amino acid
Carboxylic acid
Secondary aliphatic amine
Ether
Monocarboxylic acid or derivatives
Azacycle
Secondary amine
Organoheterocyclic compound
Organonitrogen compound
Organic oxygen compound
Amine
Organooxygen compound
Organosulfur compound
Organic oxide
Hydrocarbon derivative
Organopnictogen compound
Carbonyl group
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

piperidines (CHEBI:9605 )
sulfonamide (CHEBI:9605 )
L-tyrosine derivative (CHEBI:9605 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014913)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Tirofiban Action Pathway (PathBank: SMP0000267)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0032 g/L	Not Available
LogP	1.4	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0032 g/L	ALOGPS
logP	1.78	ALOGPS
logP	0.6	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	3.17	ChemAxon
pKa (Strongest Basic)	10.21	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.73 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	117.48 m³·mol⁻¹	ChemAxon
Polarizability	49.27 Å³	ChemAxon
Number of Rings	2	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
DarkChem	[M+H]+	199.882	31661259
DarkChem	[M-H]-	200.972	31661259
DeepCCS	[M+H]+	208.827	30932474
DeepCCS	[M-H]-	206.469	30932474
DeepCCS	[M-2H]-	240.73	30932474
DeepCCS	[M+Na]+	215.957	30932474
AllCCS	[M+H]+	204.3	32859911
AllCCS	[M+H-H2O]+	202.4	32859911
AllCCS	[M+NH4]+	206.0	32859911
AllCCS	[M+Na]+	206.5	32859911
AllCCS	[M-H]-	196.1	32859911
AllCCS	[M+Na-2H]-	197.6	32859911
AllCCS	[M+HCOO]-	199.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tirofiban	CCCCS(=O)(=O)N[C@@H](CC1=CC=C(OCCCCC2CCNCC2)C=C1)C(O)=O	5101.8	Standard polar	33892256
Tirofiban	CCCCS(=O)(=O)N[C@@H](CC1=CC=C(OCCCCC2CCNCC2)C=C1)C(O)=O	3476.1	Standard non polar	33892256
Tirofiban	CCCCS(=O)(=O)N[C@@H](CC1=CC=C(OCCCCC2CCNCC2)C=C1)C(O)=O	3633.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tirofiban,1TMS,isomer #1	CCCCS(=O)(=O)N[C@@H](CC1=CC=C(OCCCCC2CCNCC2)C=C1)C(=O)O[Si](C)(C)C	3562.2	Semi standard non polar	33892256
Tirofiban,1TMS,isomer #2	CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCNCC2)C=C1)C(=O)O)[Si](C)(C)C	3594.4	Semi standard non polar	33892256
Tirofiban,1TMS,isomer #3	CCCCS(=O)(=O)N[C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C)CC2)C=C1)C(=O)O	3649.8	Semi standard non polar	33892256
Tirofiban,2TMS,isomer #1	CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCNCC2)C=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	3571.5	Semi standard non polar	33892256
Tirofiban,2TMS,isomer #1	CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCNCC2)C=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	3709.8	Standard non polar	33892256
Tirofiban,2TMS,isomer #1	CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCNCC2)C=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	4626.9	Standard polar	33892256
Tirofiban,2TMS,isomer #2	CCCCS(=O)(=O)N[C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C)CC2)C=C1)C(=O)O[Si](C)(C)C	3604.1	Semi standard non polar	33892256
Tirofiban,2TMS,isomer #2	CCCCS(=O)(=O)N[C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C)CC2)C=C1)C(=O)O[Si](C)(C)C	3762.8	Standard non polar	33892256
Tirofiban,2TMS,isomer #2	CCCCS(=O)(=O)N[C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C)CC2)C=C1)C(=O)O[Si](C)(C)C	4763.1	Standard polar	33892256
Tirofiban,2TMS,isomer #3	CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C)CC2)C=C1)C(=O)O)[Si](C)(C)C	3623.7	Semi standard non polar	33892256
Tirofiban,2TMS,isomer #3	CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C)CC2)C=C1)C(=O)O)[Si](C)(C)C	3790.3	Standard non polar	33892256
Tirofiban,2TMS,isomer #3	CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C)CC2)C=C1)C(=O)O)[Si](C)(C)C	4785.1	Standard polar	33892256
Tirofiban,3TMS,isomer #1	CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C)CC2)C=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	3645.8	Semi standard non polar	33892256
Tirofiban,3TMS,isomer #1	CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C)CC2)C=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	3893.9	Standard non polar	33892256
Tirofiban,3TMS,isomer #1	CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C)CC2)C=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	4507.0	Standard polar	33892256
Tirofiban,1TBDMS,isomer #1	CCCCS(=O)(=O)N[C@@H](CC1=CC=C(OCCCCC2CCNCC2)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	3775.2	Semi standard non polar	33892256
Tirofiban,1TBDMS,isomer #2	CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCNCC2)C=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3806.3	Semi standard non polar	33892256
Tirofiban,1TBDMS,isomer #3	CCCCS(=O)(=O)N[C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C(C)(C)C)CC2)C=C1)C(=O)O	3870.7	Semi standard non polar	33892256
Tirofiban,2TBDMS,isomer #1	CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCNCC2)C=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4029.4	Semi standard non polar	33892256
Tirofiban,2TBDMS,isomer #1	CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCNCC2)C=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4206.3	Standard non polar	33892256
Tirofiban,2TBDMS,isomer #1	CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCNCC2)C=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4604.6	Standard polar	33892256
Tirofiban,2TBDMS,isomer #2	CCCCS(=O)(=O)N[C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C(C)(C)C)CC2)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	4054.2	Semi standard non polar	33892256
Tirofiban,2TBDMS,isomer #2	CCCCS(=O)(=O)N[C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C(C)(C)C)CC2)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	4240.5	Standard non polar	33892256
Tirofiban,2TBDMS,isomer #2	CCCCS(=O)(=O)N[C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C(C)(C)C)CC2)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	4805.0	Standard polar	33892256
Tirofiban,2TBDMS,isomer #3	CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C(C)(C)C)CC2)C=C1)C(=O)O)[Si](C)(C)C(C)(C)C	4104.6	Semi standard non polar	33892256
Tirofiban,2TBDMS,isomer #3	CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C(C)(C)C)CC2)C=C1)C(=O)O)[Si](C)(C)C(C)(C)C	4250.9	Standard non polar	33892256
Tirofiban,2TBDMS,isomer #3	CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C(C)(C)C)CC2)C=C1)C(=O)O)[Si](C)(C)C(C)(C)C	4813.3	Standard polar	33892256
Tirofiban,3TBDMS,isomer #1	CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C(C)(C)C)CC2)C=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4341.4	Semi standard non polar	33892256
Tirofiban,3TBDMS,isomer #1	CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C(C)(C)C)CC2)C=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4601.2	Standard non polar	33892256
Tirofiban,3TBDMS,isomer #1	CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C(C)(C)C)CC2)C=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4551.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tirofiban GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9233000000-449c9f26afd8b05e7422	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tirofiban GC-MS (1 TMS) - 70eV, Positive	splash10-0a4j-9241200000-c8cce3f0150c49c7b4b9	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tirofiban 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 - Tirofiban 10V, Positive-QTOF	splash10-006y-0549500000-2974f1cff243a2edea70	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tirofiban 20V, Positive-QTOF	splash10-05fr-8978100000-c82b954a66a21d7b7b16	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tirofiban 40V, Positive-QTOF	splash10-052f-4960000000-99f01b2e16edac7fb882	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tirofiban 10V, Negative-QTOF	splash10-000i-0417900000-2def9a867e11bd4431b8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tirofiban 20V, Negative-QTOF	splash10-00di-2947100000-e78108adb072e11a5add	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tirofiban 40V, Negative-QTOF	splash10-024u-6940000000-5ebd43e473a27543a015	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tirofiban 10V, Positive-QTOF	splash10-0006-0016900000-2cd3d85cb7f7753eceb7	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tirofiban 20V, Positive-QTOF	splash10-004i-1096000000-d6ff280138c0c8f31cb8	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tirofiban 40V, Positive-QTOF	splash10-0006-8910000000-a1aaa15fb128bd3ad5a3	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tirofiban 10V, Negative-QTOF	splash10-00kr-1502900000-6b2945d27bec9c418749	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tirofiban 20V, Negative-QTOF	splash10-00di-9024000000-1371a4b5fb1f8011211d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tirofiban 40V, Negative-QTOF	splash10-022a-9431100000-8c15bfa5f044a4504b3f	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
Tirofiban 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 DB00775	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00775	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00775

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

54912

KEGG Compound ID

C07965

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tirofiban

METLIN ID

Not Available

PubChem Compound

60947

PDB ID

Not Available

ChEBI ID

9605

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. Integrin alpha-IIb

General function:: Involved in cell adhesion
Specific function:: Integrin alpha-IIb/beta-3 is a receptor for fibronectin, fibrinogen, plasminogen, prothrombin, thrombospondin and vitronectin. It recognizes the sequence R-G-D in a wide array of ligands. It recognizes the sequence H-H-L-G-G-G-A-K-Q-A-G-D-V in fibrinogen gamma chain. Following activation integrin alpha- IIb/beta-3 brings about platelet/platelet interaction through binding of soluble fibrinogen. This step leads to rapid platelet aggregation which physically plugs ruptured endothelial cell surface
Gene Name:: ITGA2B
Uniprot ID:: P08514
Molecular weight:: 113376.0

References

Theroux P, Alexander J Jr, Pharand C, Barr E, Snapinn S, Ghannam AF, Sax FL: Glycoprotein IIb/IIIa receptor blockade improves outcomes in diabetic patients presenting with unstable angina/non-ST-elevation myocardial infarction: results from the Platelet Receptor Inhibition in Ischemic Syndrome Management in Patients Limited by Unstable Signs and Symptoms (PRISM-PLUS) study. Circulation. 2000 Nov 14;102(20):2466-72. [PubMed:11076818 ]
Dickfeld T, Ruf A, Pogatsa-Murray G, Muller I, Engelmann B, Taubitz W, Fischer J, Meier O, Gawaz M: Differential antiplatelet effects of various glycoprotein IIb-IIIa antagonists. Thromb Res. 2001 Jan 15;101(2):53-64. [PubMed:11342206 ]
von Segesser LK, Mueller X, Marty B, Horisberger J, Corno A: Alternatives to unfractionated heparin for anticoagulation in cardiopulmonary bypass. Perfusion. 2001 Sep;16(5):411-6. [PubMed:11565896 ]
Kondo K, Umemura K: Clinical pharmacokinetics of tirofiban, a nonpeptide glycoprotein IIb/IIIa receptor antagonist: comparison with the monoclonal antibody abciximab. Clin Pharmacokinet. 2002;41(3):187-95. [PubMed:11929319 ]
Roffi M, Moliterno DJ, Meier B, Powers ER, Grines CL, DiBattiste PM, Herrmann HC, Bertrand M, Harris KE, Demopoulos LA, Topol EJ: Impact of different platelet glycoprotein IIb/IIIa receptor inhibitors among diabetic patients undergoing percutaneous coronary intervention: : Do Tirofiban and ReoPro Give Similar Efficacy Outcomes Trial (TARGET) 1-year follow-up. Circulation. 2002 Jun 11;105(23):2730-6. [PubMed:12057986 ]
Juwana YB, Suryapranata H, Ottervanger JP, van 't Hof AW: Tirofiban for myocardial infarction. Expert Opin Pharmacother. 2010 Apr;11(5):861-6. doi: 10.1517/14656561003690005. [PubMed:20210689 ]

Showing metabocard for Tirofiban (HMDB0014913)

MOL for HMDB0014913 (Tirofiban)

3D MOL for HMDB0014913 (Tirofiban)

3D SDF for HMDB0014913 (Tirofiban)

3D-SDF for HMDB0014913 (Tirofiban)

PDB for HMDB0014913 (Tirofiban)

3D PDB for HMDB0014913 (Tirofiban)

SMILES for HMDB0014913 (Tirofiban)

INCHI for HMDB0014913 (Tirofiban)

Structure for HMDB0014913 (Tirofiban)

3D Structure for HMDB0014913 (Tirofiban)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References