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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:05 UTC

HMDB ID

HMDB0015704

Secondary Accession Numbers

HMDB15704

Metabolite Identification

Common Name

Tafluprost

Description

Tafluprost is only found in individuals that have used or taken this drug. It is a prostaglandin analogue used topically (as eye drops) to control the progression of glaucoma and in the management of ocular hypertension. Tafluprost was approved for use in the U.S. on February 10, 2012.Tafluprost is a prostaglandin F2a analogue. Specifically, Tafluprost is a prostanoid selective FP receptor agonist that is believed to reduce the intraocular pressure (IOP) by increasing the outflow of aqueous humor. Studies in animals and man suggest that the main mechanism of action is increased uveoscleral outflow.

Structure

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

[NO NAME]
  Mrv0541 02271202182D          
Created with ChemWriter - http://chemwriter.com
 32 33  0  0  1  0            999 V2000
    2.2540   -0.3771    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

HMDB0015704
     RDKit          3D
Tafluprost
 66 67  0  0  0  0  0  0  0  0999 V2000
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M  END

[NO NAME]
  Mrv0541 02271202182D          
Created with ChemWriter - http://chemwriter.com
 32 33  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
HMDB0015704

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)OC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\C(F)(F)COC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H34F2O5/c1-18(2)32-24(30)13-9-4-3-8-12-20-21(23(29)16-22(20)28)14-15-25(26,27)17-31-19-10-6-5-7-11-19/h3,5-8,10-11,14-15,18,20-23,28-29H,4,9,12-13,16-17H2,1-2H3/b8-3-,15-14+/t20-,21-,22+,23-/m1/s1

> <INCHI_KEY>
WSNODXPBBALQOF-VEJSHDCNSA-N

> <FORMULA>
C25H34F2O5

> <MOLECULAR_WEIGHT>
452.5313

> <EXACT_MASS>
452.237430608

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
48.6535257011762

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
propan-2-yl (5Z)-7-[(1R,2R,3R,5S)-2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl]hept-5-enoate

> <ALOGPS_LOGP>
4.46

> <JCHEM_LOGP>
4.2923223713333325

> <ALOGPS_LOGS>
-4.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.223490488779635

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.513877492123004

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8720050891706874

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
120.58930000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.28e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tafluprost

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015704
     RDKit          3D
Tafluprost
 66 67  0  0  0  0  0  0  0  0999 V2000
   -8.8039    0.9345   -0.9878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7306    1.8029   -0.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6699    3.0737   -1.2271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4746    1.1609   -0.3419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7757    0.9421    0.8068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2510    1.3251    1.9026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4605    0.2614    0.8150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9128    0.1557    2.2427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5500   -0.5610    2.1593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8280   -1.8705    1.5740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3146   -2.3179    0.4467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3913   -1.5060   -0.3362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0317   -2.1446   -0.5125 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0679   -3.4697   -1.2178 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3109   -3.7789   -1.7678 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8868   -3.3364   -2.4028 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8503   -2.2907   -1.8890 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6357   -1.7521   -2.9024 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9080   -1.2633   -1.2988 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6074   -0.2743   -0.4570 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9238   -0.1930   -0.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5837    0.8366    0.5520 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0607    2.0715    0.2997 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.4598    0.4272    1.8508 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.0535    0.8726    0.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7657    1.8243    0.9046 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1111    2.0621    0.7329 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8619    1.3792   -0.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2138    1.6439   -0.3630 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8511    2.5774    0.4159 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1241    3.2661    1.3651 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7731    2.9936    1.5021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6856   -0.1458   -0.7436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9416    1.1089   -2.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7759    1.2350   -0.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0241    2.0837    0.6171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7174    3.4262   -1.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1647    2.9229   -2.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0960    3.8430   -0.6603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5892   -0.8024    0.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7383    0.7586    0.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5823   -0.5448    2.7814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8249    1.1261    2.7300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9033    0.1185    1.6297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2240   -0.6404    3.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5326   -2.5219    2.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6072   -3.3434    0.1013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2500   -0.4738   -0.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8282   -1.4794   -1.3917 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3786   -2.2709    0.5320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3254   -4.3008   -0.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1571   -4.3425   -2.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3689   -4.2843   -2.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3575   -2.8732   -3.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4495   -2.7501   -1.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2617   -2.4643   -3.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3335   -0.8163   -2.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9981    0.4366    0.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5059   -0.9276   -0.8874 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5496   -0.1029    0.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1561    1.1378   -0.9323 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3338    0.6502   -0.8164 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7673    1.0785   -1.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9039    2.7785    0.2974 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6450    3.9879    1.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2107    3.5398    2.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 22 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 19 13  1  0
 32 27  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 11 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  1
 14 51  1  1
 15 52  1  0
 16 53  1  0
 16 54  1  0
 17 55  1  1
 18 56  1  0
 19 57  1  6
 20 58  1  0
 21 59  1  0
 25 60  1  0
 25 61  1  0
 28 62  1  0
 29 63  1  0
 30 64  1  0
 31 65  1  0
 32 66  1  0
M  END

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: [NO NAME]                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  F   UNK     0       4.207  -0.704   0.000  0.00  0.00           F+0
HETATM    2  F   UNK     0       7.287  -0.704   0.000  0.00  0.00           F+0
HETATM    3  O   UNK     0       8.756   6.762   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.370   3.575   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       4.414  -3.014   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      16.290  -1.341   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      17.115   1.196   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.327   4.051   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.081   3.146   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.851   5.516   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.835   4.051   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.311   5.516   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.791   3.575   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.081   1.606   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.936   4.606   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.747   0.836   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.401   4.130   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.747  -0.704   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.721   2.624   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.747  -2.244   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.185   2.148   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.505   0.641   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.970   0.165   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.414  -4.554   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.755  -1.817   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.747  -5.324   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.080  -5.324   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      18.899  -0.786   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      18.075  -3.323   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.747  -6.864   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.080  -6.864   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.414  -7.634   0.000  0.00  0.00           C+0
CONECT    1   18                                                            
CONECT    2   18                                                            
CONECT    3   10                                                            
CONECT    4   11                                                            
CONECT    5   20   24                                                       
CONECT    6   23   25                                                       
CONECT    7   23                                                            
CONECT    8    9   10   13                                                  
CONECT    9    8   11   14                                                  
CONECT   10    3    8   12                                                  
CONECT   11    4    9   12                                                  
CONECT   12   10   11                                                       
CONECT   13    8   15                                                       
CONECT   14    9   16                                                       
CONECT   15   13   17                                                       
CONECT   16   14   18                                                       
CONECT   17   15   19                                                       
CONECT   18    1    2   16   20                                             
CONECT   19   17   21                                                       
CONECT   20    5   18                                                       
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23    6    7   22                                                  
CONECT   24    5   26   27                                                  
CONECT   25    6   28   29                                                  
CONECT   26   24   30                                                       
CONECT   27   24   31                                                       
CONECT   28   25                                                            
CONECT   29   25                                                            
CONECT   30   26   32                                                       
CONECT   31   27   32                                                       
CONECT   32   30   31                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   66    0
END

COMPND    HMDB0015704
HETATM    1  C1  UNL     1      -8.804   0.934  -0.988  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.731   1.803  -0.414  1.00  0.00           C  
HETATM    3  C3  UNL     1      -7.670   3.074  -1.227  1.00  0.00           C  
HETATM    4  O1  UNL     1      -6.475   1.161  -0.342  1.00  0.00           O  
HETATM    5  C4  UNL     1      -5.776   0.942   0.807  1.00  0.00           C  
HETATM    6  O2  UNL     1      -6.251   1.325   1.903  1.00  0.00           O  
HETATM    7  C5  UNL     1      -4.460   0.261   0.815  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.913   0.156   2.243  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.550  -0.561   2.159  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.828  -1.870   1.574  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.315  -2.318   0.447  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.391  -1.506  -0.336  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.032  -2.145  -0.513  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.068  -3.470  -1.218  1.00  0.00           C  
HETATM   15  O3  UNL     1      -1.311  -3.779  -1.768  1.00  0.00           O  
HETATM   16  C13 UNL     1       0.887  -3.336  -2.403  1.00  0.00           C  
HETATM   17  C14 UNL     1       1.850  -2.291  -1.889  1.00  0.00           C  
HETATM   18  O4  UNL     1       2.636  -1.752  -2.902  1.00  0.00           O  
HETATM   19  C15 UNL     1       0.908  -1.263  -1.299  1.00  0.00           C  
HETATM   20  C16 UNL     1       1.607  -0.274  -0.457  1.00  0.00           C  
HETATM   21  C17 UNL     1       2.924  -0.193  -0.321  1.00  0.00           C  
HETATM   22  C18 UNL     1       3.584   0.837   0.552  1.00  0.00           C  
HETATM   23  F1  UNL     1       3.061   2.072   0.300  1.00  0.00           F  
HETATM   24  F2  UNL     1       3.460   0.427   1.851  1.00  0.00           F  
HETATM   25  C19 UNL     1       5.053   0.873   0.130  1.00  0.00           C  
HETATM   26  O5  UNL     1       5.766   1.824   0.905  1.00  0.00           O  
HETATM   27  C20 UNL     1       7.111   2.062   0.733  1.00  0.00           C  
HETATM   28  C21 UNL     1       7.862   1.379  -0.218  1.00  0.00           C  
HETATM   29  C22 UNL     1       9.214   1.644  -0.363  1.00  0.00           C  
HETATM   30  C23 UNL     1       9.851   2.577   0.416  1.00  0.00           C  
HETATM   31  C24 UNL     1       9.124   3.266   1.365  1.00  0.00           C  
HETATM   32  C25 UNL     1       7.773   2.994   1.502  1.00  0.00           C  
HETATM   33  H1  UNL     1      -8.686  -0.146  -0.744  1.00  0.00           H  
HETATM   34  H2  UNL     1      -8.942   1.109  -2.080  1.00  0.00           H  
HETATM   35  H3  UNL     1      -9.776   1.235  -0.520  1.00  0.00           H  
HETATM   36  H4  UNL     1      -8.024   2.084   0.617  1.00  0.00           H  
HETATM   37  H5  UNL     1      -8.717   3.426  -1.370  1.00  0.00           H  
HETATM   38  H6  UNL     1      -7.165   2.923  -2.198  1.00  0.00           H  
HETATM   39  H7  UNL     1      -7.096   3.843  -0.660  1.00  0.00           H  
HETATM   40  H8  UNL     1      -4.589  -0.802   0.462  1.00  0.00           H  
HETATM   41  H9  UNL     1      -3.738   0.759   0.160  1.00  0.00           H  
HETATM   42  H10 UNL     1      -4.582  -0.545   2.781  1.00  0.00           H  
HETATM   43  H11 UNL     1      -3.825   1.126   2.730  1.00  0.00           H  
HETATM   44  H12 UNL     1      -1.903   0.119   1.630  1.00  0.00           H  
HETATM   45  H13 UNL     1      -2.224  -0.640   3.244  1.00  0.00           H  
HETATM   46  H14 UNL     1      -3.533  -2.522   2.146  1.00  0.00           H  
HETATM   47  H15 UNL     1      -2.607  -3.343   0.101  1.00  0.00           H  
HETATM   48  H16 UNL     1      -1.250  -0.474  -0.074  1.00  0.00           H  
HETATM   49  H17 UNL     1      -1.828  -1.479  -1.392  1.00  0.00           H  
HETATM   50  H18 UNL     1       0.379  -2.271   0.532  1.00  0.00           H  
HETATM   51  H19 UNL     1       0.325  -4.301  -0.580  1.00  0.00           H  
HETATM   52  H20 UNL     1      -1.157  -4.342  -2.564  1.00  0.00           H  
HETATM   53  H21 UNL     1       1.369  -4.284  -2.662  1.00  0.00           H  
HETATM   54  H22 UNL     1       0.357  -2.873  -3.269  1.00  0.00           H  
HETATM   55  H23 UNL     1       2.449  -2.750  -1.091  1.00  0.00           H  
HETATM   56  H24 UNL     1       3.262  -2.464  -3.184  1.00  0.00           H  
HETATM   57  H25 UNL     1       0.333  -0.816  -2.127  1.00  0.00           H  
HETATM   58  H26 UNL     1       0.998   0.437   0.089  1.00  0.00           H  
HETATM   59  H27 UNL     1       3.506  -0.928  -0.887  1.00  0.00           H  
HETATM   60  H28 UNL     1       5.550  -0.103   0.284  1.00  0.00           H  
HETATM   61  H29 UNL     1       5.156   1.138  -0.932  1.00  0.00           H  
HETATM   62  H30 UNL     1       7.334   0.650  -0.816  1.00  0.00           H  
HETATM   63  H31 UNL     1       9.767   1.079  -1.129  1.00  0.00           H  
HETATM   64  H32 UNL     1      10.904   2.778   0.297  1.00  0.00           H  
HETATM   65  H33 UNL     1       9.645   3.988   1.959  1.00  0.00           H  
HETATM   66  H34 UNL     1       7.211   3.540   2.250  1.00  0.00           H  
CONECT    1    2   33   34   35
CONECT    2    3    4   36
CONECT    3   37   38   39
CONECT    4    5
CONECT    5    6    6    7
CONECT    7    8   40   41
CONECT    8    9   42   43
CONECT    9   10   44   45
CONECT   10   11   11   46
CONECT   11   12   47
CONECT   12   13   48   49
CONECT   13   14   19   50
CONECT   14   15   16   51
CONECT   15   52
CONECT   16   17   53   54
CONECT   17   18   19   55
CONECT   18   56
CONECT   19   20   57
CONECT   20   21   21   58
CONECT   21   22   59
CONECT   22   23   24   25
CONECT   25   26   60   61
CONECT   26   27
CONECT   27   28   28   32
CONECT   28   29   62
CONECT   29   30   30   63
CONECT   30   31   64
CONECT   31   32   32   65
CONECT   32   66
END

HMDB0015704
     RDKit          3D
Tafluprost
 66 67  0  0  0  0  0  0  0  0999 V2000
   -8.8039    0.9345   -0.9878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7306    1.8029   -0.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6699    3.0737   -1.2271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4746    1.1609   -0.3419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7757    0.9421    0.8068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2510    1.3251    1.9026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4605    0.2614    0.8150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9128    0.1557    2.2427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5500   -0.5610    2.1593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8280   -1.8705    1.5740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3146   -2.3179    0.4467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3913   -1.5060   -0.3362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0317   -2.1446   -0.5125 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0679   -3.4697   -1.2178 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3109   -3.7789   -1.7678 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8868   -3.3364   -2.4028 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8503   -2.2907   -1.8890 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6357   -1.7521   -2.9024 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9080   -1.2633   -1.2988 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6074   -0.2743   -0.4570 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9238   -0.1930   -0.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5837    0.8366    0.5520 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0607    2.0715    0.2997 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.4598    0.4272    1.8508 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.0535    0.8726    0.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7657    1.8243    0.9046 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1111    2.0621    0.7329 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8619    1.3792   -0.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2138    1.6439   -0.3630 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8511    2.5774    0.4159 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1241    3.2661    1.3651 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7731    2.9936    1.5021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6856   -0.1458   -0.7436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9416    1.1089   -2.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7759    1.2350   -0.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0241    2.0837    0.6171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7174    3.4262   -1.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1647    2.9229   -2.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0960    3.8430   -0.6603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5892   -0.8024    0.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7383    0.7586    0.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5823   -0.5448    2.7814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8249    1.1261    2.7300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9033    0.1185    1.6297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2240   -0.6404    3.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5326   -2.5219    2.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6072   -3.3434    0.1013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2500   -0.4738   -0.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8282   -1.4794   -1.3917 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3786   -2.2709    0.5320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3254   -4.3008   -0.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1571   -4.3425   -2.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3689   -4.2843   -2.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3575   -2.8732   -3.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4495   -2.7501   -1.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2617   -2.4643   -3.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3335   -0.8163   -2.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9981    0.4366    0.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5059   -0.9276   -0.8874 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5496   -0.1029    0.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1561    1.1378   -0.9323 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3338    0.6502   -0.8164 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7673    1.0785   -1.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9039    2.7785    0.2974 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6450    3.9879    1.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2107    3.5398    2.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 22 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 19 13  1  0
 32 27  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 11 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  1
 14 51  1  1
 15 52  1  0
 16 53  1  0
 16 54  1  0
 17 55  1  1
 18 56  1  0
 19 57  1  6
 20 58  1  0
 21 59  1  0
 25 60  1  0
 25 61  1  0
 28 62  1  0
 29 63  1  0
 30 64  1  0
 31 65  1  0
 32 66  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Zioptan	ChEBI
AFP-168	HMDB
Saflutan	HMDB
1-Methylethyl (5Z)-7-((1R,2R, 3R,5S)-2-((1E)-3,3-difluoro-4-phenoxy -1-butenyl)-3,5-dihydroxycyclopentyl)-5-heptenoate	HMDB

Chemical Formula

C₂₅H₃₄F₂O₅

Average Molecular Weight

452.5313

Monoisotopic Molecular Weight

452.237430608

IUPAC Name

propan-2-yl (5Z)-7-[(1R,2R,3R,5S)-2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl]hept-5-enoate

Traditional Name

tafluprost

CAS Registry Number

209860-87-7

SMILES

CC(C)OC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\C(F)(F)COC1=CC=CC=C1

InChI Identifier

InChI=1S/C25H34F2O5/c1-18(2)32-24(30)13-9-4-3-8-12-20-21(23(29)16-22(20)28)14-15-25(26,27)17-31-19-10-6-5-7-11-19/h3,5-8,10-11,14-15,18,20-23,28-29H,4,9,12-13,16-17H2,1-2H3/b8-3-,15-14+/t20-,21-,22+,23-/m1/s1

InChI Key

WSNODXPBBALQOF-VEJSHDCNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Prostaglandins and related compounds

Alternative Parents

Substituents

Prostaglandin skeleton
Phenoxy compound
Phenol ether
Alkyl aryl ether
Fatty acid ester
Benzenoid
Monocyclic benzene moiety
Cyclopentanol
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Ether
Organooxygen compound
Alkyl fluoride
Alcohol
Organohalogen compound
Organofluoride
Carbonyl group
Hydrocarbon derivative
Alkyl halide
Organic oxygen compound
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

organofluorine compound (CHEBI:66899 )
carboxylic ester (CHEBI:66899 )
prostaglandins Falpha (CHEBI:66899 )

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: HMDB0015704)

Source

Exogenous

Exogenous (HMDB: HMDB0015704)

Process

Not Available

Role

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0053 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0053 g/L	ALOGPS
logP	4.46	ALOGPS
logP	4.29	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	14.51	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	120.59 m³·mol⁻¹	ChemAxon
Polarizability	48.65 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
DeepCCS	[M+H]+	213.347	30932474
DeepCCS	[M-H]-	211.068	30932474
DeepCCS	[M-2H]-	244.308	30932474
DeepCCS	[M+Na]+	219.259	30932474
AllCCS	[M+H]+	212.1	32859911
AllCCS	[M+H-H2O]+	210.1	32859911
AllCCS	[M+NH4]+	214.0	32859911
AllCCS	[M+Na]+	214.6	32859911
AllCCS	[M-H]-	205.8	32859911
AllCCS	[M+Na-2H]-	207.7	32859911
AllCCS	[M+HCOO]-	209.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tafluprost	CC(C)OC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\C(F)(F)COC1=CC=CC=C1	3913.9	Standard polar	33892256
Tafluprost	CC(C)OC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\C(F)(F)COC1=CC=CC=C1	2953.1	Standard non polar	33892256
Tafluprost	CC(C)OC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\C(F)(F)COC1=CC=CC=C1	3034.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tafluprost,1TMS,isomer #1	CC(C)OC(=O)CCC/C=C\C[C@H]1[C@@H](O[Si](C)(C)C)C[C@@H](O)[C@@H]1/C=C/C(F)(F)COC1=CC=CC=C1	2891.4	Semi standard non polar	33892256
Tafluprost,1TMS,isomer #2	CC(C)OC(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O[Si](C)(C)C)[C@@H]1/C=C/C(F)(F)COC1=CC=CC=C1	2901.4	Semi standard non polar	33892256
Tafluprost,2TMS,isomer #1	CC(C)OC(=O)CCC/C=C\C[C@H]1[C@@H](O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)[C@@H]1/C=C/C(F)(F)COC1=CC=CC=C1	2877.4	Semi standard non polar	33892256
Tafluprost,1TBDMS,isomer #1	CC(C)OC(=O)CCC/C=C\C[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@@H]1/C=C/C(F)(F)COC1=CC=CC=C1	3098.7	Semi standard non polar	33892256
Tafluprost,1TBDMS,isomer #2	CC(C)OC(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1/C=C/C(F)(F)COC1=CC=CC=C1	3111.0	Semi standard non polar	33892256
Tafluprost,2TBDMS,isomer #1	CC(C)OC(=O)CCC/C=C\C[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1/C=C/C(F)(F)COC1=CC=CC=C1	3277.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tafluprost GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-4439700000-5f902e96f572f76cc593	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tafluprost GC-MS (2 TMS) - 70eV, Positive	splash10-001l-7200690000-8373b0788e1ed396a7fa	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tafluprost 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 - Tafluprost 10V, Positive-QTOF	splash10-00kv-3015900000-c886925c3b2c359329fb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tafluprost 20V, Positive-QTOF	splash10-03dj-6119200000-4d3efe181e45c7a457c4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tafluprost 40V, Positive-QTOF	splash10-03dj-9011000000-010b663ce499bf30d948	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tafluprost 10V, Negative-QTOF	splash10-0006-9000200000-0e451520fe294c5b8f6b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tafluprost 20V, Negative-QTOF	splash10-0006-9000000000-36b6f74a5c34571e3a78	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tafluprost 40V, Negative-QTOF	splash10-0a4l-9000000000-921114351b038266dd2e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tafluprost 10V, Positive-QTOF	splash10-0py3-0019500000-5b4599f3f7676f5d531e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tafluprost 20V, Positive-QTOF	splash10-00mo-2119200000-d5684e822eb13b29e9b9	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tafluprost 40V, Positive-QTOF	splash10-0561-9610000000-eb4fe1a3cbe0fdfe9daa	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tafluprost 10V, Negative-QTOF	splash10-0006-9000400000-706df0cdfeceb3c1bf1a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tafluprost 20V, Negative-QTOF	splash10-0006-9000000000-f096008f6b882e68cef4	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tafluprost 40V, Negative-QTOF	splash10-0006-9000000000-08485aaf085c13d5129a	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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 DB08819	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB08819	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB08819

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8044182

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tafluprost

METLIN ID

Not Available

PubChem Compound

9868491

PDB ID

Not Available

ChEBI ID

66899

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1799771

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Takagi Y, Nakajima T, Shimazaki A, Kageyama M, Matsugi T, Matsumura Y, Gabelt BT, Kaufman PL, Hara H: Pharmacological characteristics of AFP-168 (tafluprost), a new prostanoid FP receptor agonist, as an ocular hypotensive drug. Exp Eye Res. 2004 Apr;78(4):767-76. [PubMed:15037111 ]
Pantcheva MB, Seibold LK, Awadallah NS, Kahook MY: Tafluprost: a novel prostaglandin analog for treatment of glaucoma. Adv Ther. 2011 Sep;28(9):707-15. doi: 10.1007/s12325-011-0055-8. Epub 2011 Aug 18. [PubMed:21858491 ]
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Showing metabocard for Tafluprost (HMDB0015704)

MOL for HMDB0015704 (Tafluprost)

3D MOL for HMDB0015704 (Tafluprost)

3D SDF for HMDB0015704 (Tafluprost)

3D-SDF for HMDB0015704 (Tafluprost)

PDB for HMDB0015704 (Tafluprost)

3D PDB for HMDB0015704 (Tafluprost)

SMILES for HMDB0015704 (Tafluprost)

INCHI for HMDB0015704 (Tafluprost)

Structure for HMDB0015704 (Tafluprost)

3D Structure for HMDB0015704 (Tafluprost)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra