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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:01:37 UTC

Update Date

2021-09-14 15:39:00 UTC

HMDB ID

HMDB0014256

Secondary Accession Numbers

HMDB14256

Metabolite Identification

Common Name

Tafluprost free acid

Description

Tafluprost free acid 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. Based on a literature review a small amount of articles have been published on Tafluprost free acid.

Structure

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


  Mrv0541 06191311032D          

 29 30  0  0  0  0            999 V2000
    4.8897   -3.6060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6043   -4.0209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6043   -4.8432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3190   -3.6060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0337   -4.0209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7484   -3.6060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7484   -2.7838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4630   -2.3688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1699   -2.7838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8846   -2.3688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9768   -1.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3621   -1.0010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7837   -1.3775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1910   -2.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0131   -2.1767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6377   -2.7069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8144   -3.5137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5982   -3.7673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7672   -4.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5741   -4.4052    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.9363   -5.3812    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.9604   -4.7433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7068   -5.5271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8999   -5.7038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6464   -6.4877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8395   -6.6567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2862   -6.0419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5398   -5.2582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3467   -5.0891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 16  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 29  2  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
M  END

HMDB0014256
     RDKit          3D
Tafluprost free acid
 57 58  0  0  0  0  0  0  0  0999 V2000
   -6.6917    2.9205   -1.3529 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4496    2.8548   -1.2744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6980    3.9715   -1.5983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7311    1.6291   -0.8474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6874    0.5065   -0.5310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8068   -0.6870   -0.1069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0552   -0.2292    1.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7517   -0.1836    1.1036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8951   -0.5834   -0.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0254   -1.7329    0.4964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9364   -2.8853    0.9394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8134   -3.2535   -0.0745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9167   -3.9971    1.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0617   -3.7634   -0.0603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1517   -4.6923   -1.0790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2032   -2.3410   -0.5733 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1097   -1.6701   -0.8133 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5703   -0.6352   -0.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8947   -0.0000   -0.4413 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7779   -0.4381    0.5029 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.3194   -0.3158   -1.7347 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.8009    1.5052   -0.3905 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9332    2.1780   -0.6375 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1660    2.4468   -0.2581 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9159    3.3198   -1.0716 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1959    3.6650   -0.7707 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7845    3.1525    0.3581 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0947    2.3007    1.1791 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8025    1.9629    0.8603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1186    4.8850   -1.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0869    1.3202   -1.6846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0795    1.8978   -0.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2152    0.2503   -1.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3596    0.7514    0.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5348   -1.4757    0.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2511   -0.9555   -0.9965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6613    0.0909    1.9575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2491    0.1692    2.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3623   -0.8141   -0.9625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1659    0.2649   -0.2252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4835   -1.4157    1.3900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4440   -2.6613    1.8876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6403   -2.8346   -0.9322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4035   -3.9685    2.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4181   -4.9851    0.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0845   -3.8457    0.3320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5684   -5.3490   -1.0378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7468   -2.3586   -1.5238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7306   -2.0831   -1.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9738   -0.2102    0.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9152    1.8432   -1.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4242    1.8195    0.6493 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4623    3.7420   -1.9818 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7991    4.3378   -1.3816 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8014    3.4033    0.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5363    1.8789    2.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3111    1.2974    1.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 16 10  1  0
 29 24  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 16 48  1  0
 17 49  1  0
 18 50  1  0
 22 51  1  0
 22 52  1  0
 25 53  1  0
 26 54  1  0
 27 55  1  0
 28 56  1  0
 29 57  1  0
M  END


  Mrv0541 06191311032D          

 29 30  0  0  0  0            999 V2000
    4.8897   -3.6060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6043   -4.0209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6043   -4.8432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3190   -3.6060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0337   -4.0209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7484   -3.6060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7484   -2.7838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4630   -2.3688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1699   -2.7838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8846   -2.3688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9768   -1.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3621   -1.0010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7837   -1.3775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1910   -2.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0131   -2.1767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6377   -2.7069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8144   -3.5137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5982   -3.7673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7672   -4.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5741   -4.4052    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.9363   -5.3812    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.9604   -4.7433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7068   -5.5271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8999   -5.7038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6464   -6.4877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8395   -6.6567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2862   -6.0419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5398   -5.2582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3467   -5.0891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 16  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 29  2  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014256

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1CC(O)C(\C=C\C(F)(F)COC2=CC=CC=C2)C1C\C=C/CCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H28F2O5/c23-22(24,15-29-16-8-4-3-5-9-16)13-12-18-17(19(25)14-20(18)26)10-6-1-2-7-11-21(27)28/h1,3-6,8-9,12-13,17-20,25-26H,2,7,10-11,14-15H2,(H,27,28)/b6-1-,13-12+

> <INCHI_KEY>
KIQXRQVVYTYYAZ-MTNCBHNASA-N

> <FORMULA>
C22H28F2O5

> <MOLECULAR_WEIGHT>
410.4515

> <EXACT_MASS>
410.190480416

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
41.99551226068043

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z)-7-{2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoic acid

> <ALOGPS_LOGP>
3.42

> <JCHEM_LOGP>
3.3730453359999992

> <ALOGPS_LOGS>
-4.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.51387749215359

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.3552935959611325

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8720050891706874

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
106.65280000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.39e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5Z)-7-{2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014256
     RDKit          3D
Tafluprost free acid
 57 58  0  0  0  0  0  0  0  0999 V2000
   -6.6917    2.9205   -1.3529 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4496    2.8548   -1.2744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6980    3.9715   -1.5983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7311    1.6291   -0.8474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6874    0.5065   -0.5310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8068   -0.6870   -0.1069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0552   -0.2292    1.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7517   -0.1836    1.1036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8951   -0.5834   -0.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0254   -1.7329    0.4964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9364   -2.8853    0.9394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8134   -3.2535   -0.0745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9167   -3.9971    1.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0617   -3.7634   -0.0603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1517   -4.6923   -1.0790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2032   -2.3410   -0.5733 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1097   -1.6701   -0.8133 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5703   -0.6352   -0.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8947   -0.0000   -0.4413 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7779   -0.4381    0.5029 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.3194   -0.3158   -1.7347 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.8009    1.5052   -0.3905 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9332    2.1780   -0.6375 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1660    2.4468   -0.2581 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9159    3.3198   -1.0716 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1959    3.6650   -0.7707 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7845    3.1525    0.3581 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0947    2.3007    1.1791 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8025    1.9629    0.8603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1186    4.8850   -1.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0869    1.3202   -1.6846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0795    1.8978   -0.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2152    0.2503   -1.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3596    0.7514    0.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5348   -1.4757    0.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2511   -0.9555   -0.9965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6613    0.0909    1.9575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2491    0.1692    2.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3623   -0.8141   -0.9625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1659    0.2649   -0.2252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4835   -1.4157    1.3900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4440   -2.6613    1.8876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6403   -2.8346   -0.9322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4035   -3.9685    2.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4181   -4.9851    0.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0845   -3.8457    0.3320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5684   -5.3490   -1.0378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7468   -2.3586   -1.5238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7306   -2.0831   -1.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9738   -0.2102    0.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9152    1.8432   -1.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4242    1.8195    0.6493 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4623    3.7420   -1.9818 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7991    4.3378   -1.3816 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8014    3.4033    0.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5363    1.8789    2.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3111    1.2974    1.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 16 10  1  0
 29 24  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 16 48  1  0
 17 49  1  0
 18 50  1  0
 22 51  1  0
 22 52  1  0
 25 53  1  0
 26 54  1  0
 27 55  1  0
 28 56  1  0
 29 57  1  0
M  END

HEADER    PROTEIN                                 19-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-13         0                                  
HETATM    1  O   UNK     0       9.127  -6.731   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      10.461  -7.506   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      10.461  -9.041   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      11.796  -6.731   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.130  -7.506   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.464  -6.731   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.464  -5.196   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.798  -4.422   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.117  -5.196   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.451  -4.422   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.623  -2.901   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      17.476  -1.868   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      20.130  -2.571   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.890  -3.905   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      22.425  -4.063   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      19.857  -5.053   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      20.187  -6.559   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      21.650  -7.032   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      21.966  -8.539   0.000  0.00  0.00           C+0
HETATM   20  F   UNK     0      23.472  -8.223   0.000  0.00  0.00           F+0
HETATM   21  F   UNK     0      22.281 -10.045   0.000  0.00  0.00           F+0
HETATM   22  C   UNK     0      20.459  -8.854   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      19.986 -10.317   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      18.480 -10.647   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      18.007 -12.110   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      16.500 -12.426   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.468 -11.278   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.941  -9.815   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      17.447  -9.500   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   10   14   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   24   28                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   60    0
END

COMPND    HMDB0014256
HETATM    1  O1  UNL     1      -6.692   2.920  -1.353  1.00  0.00           O  
HETATM    2  C1  UNL     1      -5.450   2.855  -1.274  1.00  0.00           C  
HETATM    3  O2  UNL     1      -4.698   3.971  -1.598  1.00  0.00           O  
HETATM    4  C2  UNL     1      -4.731   1.629  -0.847  1.00  0.00           C  
HETATM    5  C3  UNL     1      -5.687   0.507  -0.531  1.00  0.00           C  
HETATM    6  C4  UNL     1      -4.807  -0.687  -0.107  1.00  0.00           C  
HETATM    7  C5  UNL     1      -4.055  -0.229   1.066  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.752  -0.184   1.104  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.895  -0.583  -0.018  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.025  -1.733   0.496  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.936  -2.885   0.939  1.00  0.00           C  
HETATM   12  O3  UNL     1      -2.813  -3.254  -0.074  1.00  0.00           O  
HETATM   13  C10 UNL     1      -0.917  -3.997   1.067  1.00  0.00           C  
HETATM   14  C11 UNL     1       0.062  -3.763  -0.060  1.00  0.00           C  
HETATM   15  O4  UNL     1      -0.152  -4.692  -1.079  1.00  0.00           O  
HETATM   16  C12 UNL     1      -0.203  -2.341  -0.573  1.00  0.00           C  
HETATM   17  C13 UNL     1       1.110  -1.670  -0.813  1.00  0.00           C  
HETATM   18  C14 UNL     1       1.570  -0.635  -0.159  1.00  0.00           C  
HETATM   19  C15 UNL     1       2.895  -0.000  -0.441  1.00  0.00           C  
HETATM   20  F1  UNL     1       3.778  -0.438   0.503  1.00  0.00           F  
HETATM   21  F2  UNL     1       3.319  -0.316  -1.735  1.00  0.00           F  
HETATM   22  C16 UNL     1       2.801   1.505  -0.390  1.00  0.00           C  
HETATM   23  O5  UNL     1       3.933   2.178  -0.638  1.00  0.00           O  
HETATM   24  C17 UNL     1       5.166   2.447  -0.258  1.00  0.00           C  
HETATM   25  C18 UNL     1       5.916   3.320  -1.072  1.00  0.00           C  
HETATM   26  C19 UNL     1       7.196   3.665  -0.771  1.00  0.00           C  
HETATM   27  C20 UNL     1       7.784   3.152   0.358  1.00  0.00           C  
HETATM   28  C21 UNL     1       7.095   2.301   1.179  1.00  0.00           C  
HETATM   29  C22 UNL     1       5.803   1.963   0.860  1.00  0.00           C  
HETATM   30  H1  UNL     1      -5.119   4.885  -1.722  1.00  0.00           H  
HETATM   31  H2  UNL     1      -4.087   1.320  -1.685  1.00  0.00           H  
HETATM   32  H3  UNL     1      -4.079   1.898  -0.005  1.00  0.00           H  
HETATM   33  H4  UNL     1      -6.215   0.250  -1.474  1.00  0.00           H  
HETATM   34  H5  UNL     1      -6.360   0.751   0.302  1.00  0.00           H  
HETATM   35  H6  UNL     1      -5.535  -1.476   0.209  1.00  0.00           H  
HETATM   36  H7  UNL     1      -4.251  -0.956  -0.997  1.00  0.00           H  
HETATM   37  H8  UNL     1      -4.661   0.091   1.958  1.00  0.00           H  
HETATM   38  H9  UNL     1      -2.249   0.169   2.013  1.00  0.00           H  
HETATM   39  H10 UNL     1      -2.362  -0.814  -0.963  1.00  0.00           H  
HETATM   40  H11 UNL     1      -1.166   0.265  -0.225  1.00  0.00           H  
HETATM   41  H12 UNL     1      -0.484  -1.416   1.390  1.00  0.00           H  
HETATM   42  H13 UNL     1      -2.444  -2.661   1.888  1.00  0.00           H  
HETATM   43  H14 UNL     1      -2.640  -2.835  -0.932  1.00  0.00           H  
HETATM   44  H15 UNL     1      -0.403  -3.969   2.056  1.00  0.00           H  
HETATM   45  H16 UNL     1      -1.418  -4.985   0.915  1.00  0.00           H  
HETATM   46  H17 UNL     1       1.085  -3.846   0.332  1.00  0.00           H  
HETATM   47  H18 UNL     1       0.568  -5.349  -1.038  1.00  0.00           H  
HETATM   48  H19 UNL     1      -0.747  -2.359  -1.524  1.00  0.00           H  
HETATM   49  H20 UNL     1       1.731  -2.083  -1.601  1.00  0.00           H  
HETATM   50  H21 UNL     1       0.974  -0.210   0.636  1.00  0.00           H  
HETATM   51  H22 UNL     1       1.915   1.843  -1.031  1.00  0.00           H  
HETATM   52  H23 UNL     1       2.424   1.819   0.649  1.00  0.00           H  
HETATM   53  H24 UNL     1       5.462   3.742  -1.982  1.00  0.00           H  
HETATM   54  H25 UNL     1       7.799   4.338  -1.382  1.00  0.00           H  
HETATM   55  H26 UNL     1       8.801   3.403   0.631  1.00  0.00           H  
HETATM   56  H27 UNL     1       7.536   1.879   2.081  1.00  0.00           H  
HETATM   57  H28 UNL     1       5.311   1.297   1.566  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   30
CONECT    4    5   31   32
CONECT    5    6   33   34
CONECT    6    7   35   36
CONECT    7    8    8   37
CONECT    8    9   38
CONECT    9   10   39   40
CONECT   10   11   16   41
CONECT   11   12   13   42
CONECT   12   43
CONECT   13   14   44   45
CONECT   14   15   16   46
CONECT   15   47
CONECT   16   17   48
CONECT   17   18   18   49
CONECT   18   19   50
CONECT   19   20   21   22
CONECT   22   23   51   52
CONECT   23   24
CONECT   24   25   25   29
CONECT   25   26   53
CONECT   26   27   27   54
CONECT   27   28   55
CONECT   28   29   29   56
CONECT   29   57
END

HMDB0014256
     RDKit          3D
Tafluprost free acid
 57 58  0  0  0  0  0  0  0  0999 V2000
   -6.6917    2.9205   -1.3529 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4496    2.8548   -1.2744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6980    3.9715   -1.5983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7311    1.6291   -0.8474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6874    0.5065   -0.5310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8068   -0.6870   -0.1069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0552   -0.2292    1.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7517   -0.1836    1.1036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8951   -0.5834   -0.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0254   -1.7329    0.4964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9364   -2.8853    0.9394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8134   -3.2535   -0.0745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9167   -3.9971    1.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0617   -3.7634   -0.0603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1517   -4.6923   -1.0790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2032   -2.3410   -0.5733 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1097   -1.6701   -0.8133 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5703   -0.6352   -0.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8947   -0.0000   -0.4413 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7779   -0.4381    0.5029 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.3194   -0.3158   -1.7347 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.8009    1.5052   -0.3905 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9332    2.1780   -0.6375 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1660    2.4468   -0.2581 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9159    3.3198   -1.0716 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1959    3.6650   -0.7707 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7845    3.1525    0.3581 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0947    2.3007    1.1791 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8025    1.9629    0.8603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1186    4.8850   -1.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0869    1.3202   -1.6846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0795    1.8978   -0.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2152    0.2503   -1.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3596    0.7514    0.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5348   -1.4757    0.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2511   -0.9555   -0.9965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6613    0.0909    1.9575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2491    0.1692    2.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3623   -0.8141   -0.9625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1659    0.2649   -0.2252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4835   -1.4157    1.3900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4440   -2.6613    1.8876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6403   -2.8346   -0.9322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4035   -3.9685    2.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4181   -4.9851    0.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0845   -3.8457    0.3320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5684   -5.3490   -1.0378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7468   -2.3586   -1.5238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7306   -2.0831   -1.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9738   -0.2102    0.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9152    1.8432   -1.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4242    1.8195    0.6493 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4623    3.7420   -1.9818 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7991    4.3378   -1.3816 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8014    3.4033    0.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5363    1.8789    2.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3111    1.2974    1.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 16 10  1  0
 29 24  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 16 48  1  0
 17 49  1  0
 18 50  1  0
 22 51  1  0
 22 52  1  0
 25 53  1  0
 26 54  1  0
 27 55  1  0
 28 56  1  0
 29 57  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5Z)-7-{2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoate	HMDB

Chemical Formula

C₂₂H₂₈F₂O₅

Average Molecular Weight

410.4515

Monoisotopic Molecular Weight

410.190480416

IUPAC Name

(5Z)-7-{2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoic acid

Traditional Name

(5Z)-7-{2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoic acid

CAS Registry Number

Not Available

SMILES

OC1CC(O)C(\C=C\C(F)(F)COC2=CC=CC=C2)C1C\C=C/CCCC(O)=O

InChI Identifier

InChI=1S/C22H28F2O5/c23-22(24,15-29-16-8-4-3-5-9-16)13-12-18-17(19(25)14-20(18)26)10-6-1-2-7-11-21(27)28/h1,3-6,8-9,12-13,17-20,25-26H,2,7,10-11,14-15H2,(H,27,28)/b6-1-,13-12+

InChI Key

KIQXRQVVYTYYAZ-MTNCBHNASA-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
Long-chain fatty acid
Phenoxy compound
Phenol ether
Alkyl aryl ether
Halogenated fatty acid
Hydroxy fatty acid
Monocyclic benzene moiety
Fatty acid
Benzenoid
Unsaturated fatty acid
Cyclopentanol
Cyclic alcohol
Secondary alcohol
Ether
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organohalogen compound
Organofluoride
Organooxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Alkyl halide
Alkyl fluoride
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.034 g/L	ALOGPS
logP	3.42	ALOGPS
logP	3.37	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	4.36	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	106.65 m³·mol⁻¹	ChemAxon
Polarizability	42 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]+	197.475	30932474
DeepCCS	[M-H]-	194.875	30932474
DeepCCS	[M-2H]-	229.408	30932474
DeepCCS	[M+Na]+	204.636	30932474
AllCCS	[M+H]+	198.8	32859911
AllCCS	[M+H-H2O]+	196.3	32859911
AllCCS	[M+NH4]+	201.0	32859911
AllCCS	[M+Na]+	201.6	32859911
AllCCS	[M-H]-	196.3	32859911
AllCCS	[M+Na-2H]-	197.4	32859911
AllCCS	[M+HCOO]-	198.8	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.	7.04 minutes	32390414
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.	6.59 minutes	32390414
Predicted by Siyang on May 30, 2022	13.6012 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.39 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2629.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	226.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	187.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	190.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	199.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	602.1 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	505.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	132.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1246.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	536.2 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	1298.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	387.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	409.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	316.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	215.9 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	9.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tafluprost free acid	OC1CC(O)C(\C=C\C(F)(F)COC2=CC=CC=C2)C1C\C=C/CCCC(O)=O	4130.2	Standard polar	33892256
Tafluprost free acid	OC1CC(O)C(\C=C\C(F)(F)COC2=CC=CC=C2)C1C\C=C/CCCC(O)=O	2890.4	Standard non polar	33892256
Tafluprost free acid	OC1CC(O)C(\C=C\C(F)(F)COC2=CC=CC=C2)C1C\C=C/CCCC(O)=O	2960.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tafluprost free acid,1TMS,isomer #1	C[Si](C)(C)OC1CC(O)C(/C=C/C(F)(F)COC2=CC=CC=C2)C1C/C=C\CCCC(=O)O	2946.5	Semi standard non polar	33892256
Tafluprost free acid,1TMS,isomer #2	C[Si](C)(C)OC1CC(O)C(C/C=C\CCCC(=O)O)C1/C=C/C(F)(F)COC1=CC=CC=C1	2938.1	Semi standard non polar	33892256
Tafluprost free acid,1TMS,isomer #3	C[Si](C)(C)OC(=O)CCC/C=C\CC1C(O)CC(O)C1/C=C/C(F)(F)COC1=CC=CC=C1	2939.9	Semi standard non polar	33892256
Tafluprost free acid,2TMS,isomer #1	C[Si](C)(C)OC1CC(O[Si](C)(C)C)C(C/C=C\CCCC(=O)O)C1/C=C/C(F)(F)COC1=CC=CC=C1	2921.5	Semi standard non polar	33892256
Tafluprost free acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)CCC/C=C\CC1C(O[Si](C)(C)C)CC(O)C1/C=C/C(F)(F)COC1=CC=CC=C1	2888.1	Semi standard non polar	33892256
Tafluprost free acid,2TMS,isomer #3	C[Si](C)(C)OC(=O)CCC/C=C\CC1C(O)CC(O[Si](C)(C)C)C1/C=C/C(F)(F)COC1=CC=CC=C1	2879.4	Semi standard non polar	33892256
Tafluprost free acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CCC/C=C\CC1C(O[Si](C)(C)C)CC(O[Si](C)(C)C)C1/C=C/C(F)(F)COC1=CC=CC=C1	2837.7	Semi standard non polar	33892256
Tafluprost free acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CC(O)C(/C=C/C(F)(F)COC2=CC=CC=C2)C1C/C=C\CCCC(=O)O	3181.3	Semi standard non polar	33892256
Tafluprost free acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1CC(O)C(C/C=C\CCCC(=O)O)C1/C=C/C(F)(F)COC1=CC=CC=C1	3169.3	Semi standard non polar	33892256
Tafluprost free acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CCC/C=C\CC1C(O)CC(O)C1/C=C/C(F)(F)COC1=CC=CC=C1	3197.2	Semi standard non polar	33892256
Tafluprost free acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CC(O[Si](C)(C)C(C)(C)C)C(C/C=C\CCCC(=O)O)C1/C=C/C(F)(F)COC1=CC=CC=C1	3339.4	Semi standard non polar	33892256
Tafluprost free acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCC/C=C\CC1C(O[Si](C)(C)C(C)(C)C)CC(O)C1/C=C/C(F)(F)COC1=CC=CC=C1	3339.8	Semi standard non polar	33892256
Tafluprost free acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CCC/C=C\CC1C(O)CC(O[Si](C)(C)C(C)(C)C)C1/C=C/C(F)(F)COC1=CC=CC=C1	3332.9	Semi standard non polar	33892256
Tafluprost free acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC/C=C\CC1C(O[Si](C)(C)C(C)(C)C)CC(O[Si](C)(C)C(C)(C)C)C1/C=C/C(F)(F)COC1=CC=CC=C1	3470.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tafluprost free acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-014r-1219000000-8e1ec65ae01361e172d1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tafluprost free acid GC-MS (3 TMS) - 70eV, Positive	splash10-03di-5500489000-95bafbabe02fb2fdaf57	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tafluprost free acid 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 free acid 10V, Positive-QTOF	splash10-002g-1029100000-204ed18144108c4fbbb2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tafluprost free acid 20V, Positive-QTOF	splash10-002e-1229000000-25077f9e4ce508bf95e3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tafluprost free acid 40V, Positive-QTOF	splash10-000b-9260000000-076c2111abf02e5ae67b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tafluprost free acid 10V, Negative-QTOF	splash10-0006-9002200000-c00792117fdb4db5e3ef	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tafluprost free acid 20V, Negative-QTOF	splash10-0006-9001000000-08fd3ce154d6769f5222	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tafluprost free acid 40V, Negative-QTOF	splash10-0006-9110000000-0e95f48713dae3d60241	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tafluprost free acid 10V, Negative-QTOF	splash10-0006-9001300000-7aec5b4ddcff3ac3f0c2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tafluprost free acid 20V, Negative-QTOF	splash10-0006-9000000000-08485aaf085c13d5129a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tafluprost free acid 40V, Negative-QTOF	splash10-0006-9000000000-08485aaf085c13d5129a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tafluprost free acid 10V, Positive-QTOF	splash10-004l-0049100000-6ef9a55a21ae3bd86e51	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tafluprost free acid 20V, Positive-QTOF	splash10-00nr-2289000000-5abc56977aad023ef4d0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tafluprost free acid 40V, Positive-QTOF	splash10-00pu-9232000000-28994a5f3f961fcc7dbc	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

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

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

21467507

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131750728

PDB ID

Not Available

ChEBI ID

176015

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

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

Enzyme Details

1. Prostaglandin F2-alpha receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Receptor for prostaglandin F2-alpha (PGF2-alpha). The activity of this receptor is mediated by G proteins which activate a phosphatidylinositol-calcium second messenger system. Initiates luteolysis in the corpus luteum
Gene Name:: PTGFR
Uniprot ID:: P43088
Molecular weight:: 40054.1

References

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 ]

Showing metabocard for Tafluprost free acid (HMDB0014256)

MOL for HMDB0014256 (Tafluprost free acid)

3D MOL for HMDB0014256 (Tafluprost free acid)

3D SDF for HMDB0014256 (Tafluprost free acid)

3D-SDF for HMDB0014256 (Tafluprost free acid)

PDB for HMDB0014256 (Tafluprost free acid)

3D PDB for HMDB0014256 (Tafluprost free acid)

SMILES for HMDB0014256 (Tafluprost free acid)

INCHI for HMDB0014256 (Tafluprost free acid)

Structure for HMDB0014256 (Tafluprost free acid)

3D Structure for HMDB0014256 (Tafluprost free acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References