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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (7)transporters (3) Show 10 proteins XML

enzymes (7)transporters (3) Show 10 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:54 UTC

HMDB ID

HMDB0015220

Secondary Accession Numbers

HMDB15220

Metabolite Identification

Common Name

Iloprost

Description

Iloprost is only found in individuals that have used or taken this drug. It is a synthetic analogue of prostacyclin PGI2. Iloprost dilates systemic and pulmonary arterial vascular beds. It is used to treat pulmonary arterial hypertension (PAH).Iloprost is a second generation structural analog of prostacyclin (PGI) with about ten-fold greater potency than the first generation stable analogs, such as carbaprostacyclin. Iloprost binds with equal affinity to human prostacyclin (Prostanoid IP) and prostaglandin EP1 receptors. Iloprost constricts the ilium and fundus circular smooth muscle as strongly as prostaglandin E2 (PGE2) itself. Iloprost inhibits the ADP, thrombin, and collagen-induced aggregation of human platelets. In whole animals, iloprost acts as a vasodilator, hypotensive, antidiuretic, and prolongs bleeding time. All of these properties help to antagonize the pathological changes that take place in the small pulmonary arteries of patients with pulmonary hypertension.

Structure

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

1088
  Mrv0541 02231215142D          

 35 37  0  0  1  0            999 V2000
    5.1399   -1.6058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6850    1.4156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2092    0.5377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2092   -0.8913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0342    1.9667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2344   -1.1933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

HMDB0015220
     RDKit          3D
Iloprost
 73 75  0  0  0  0  0  0  0  0999 V2000
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M  END

1088
  Mrv0541 02231215142D          

 35 37  0  0  1  0            999 V2000
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 26 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 31 33  1  0  0  0  0
 32 34  2  0  0  0  0
 33 35  2  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015220

> <DATABASE_NAME>
hmdb

> <SMILES>
CC#CCC(C)C(O)\C=C\C1C(O)CC2C\C(CC12)=C\CCCC(=O)OCC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H38O5/c1-3-4-10-21(2)27(31)16-15-25-26-18-22(17-24(26)19-28(25)32)11-8-9-14-30(34)35-20-29(33)23-12-6-5-7-13-23/h5-7,11-13,15-16,21,24-28,31-32H,8-10,14,17-20H2,1-2H3/b16-15+,22-11-

> <INCHI_KEY>
CZUMMMDKQYRZDP-JCAXBLPDSA-N

> <FORMULA>
C30H38O5

> <MOLECULAR_WEIGHT>
478.6197

> <EXACT_MASS>
478.271924326

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
55.39956290836293

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-oxo-2-phenylethyl 5-[(2Z)-5-hydroxy-4-[(1E)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl]-octahydropentalen-2-ylidene]pentanoate

> <ALOGPS_LOGP>
5.04

> <JCHEM_LOGP>
4.942494925

> <ALOGPS_LOGS>
-5.38

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.153434881599377

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.723217762466295

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8733197738520245

> <JCHEM_POLAR_SURFACE_AREA>
83.82999999999998

> <JCHEM_REFRACTIVITY>
139.85299999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.00e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
iloprost

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015220
     RDKit          3D
Iloprost
 73 75  0  0  0  0  0  0  0  0999 V2000
    9.4062    1.3075   -3.5526 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3093    0.3557   -3.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4039   -0.4265   -3.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3080   -1.3637   -2.9206 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8133   -1.2051   -1.4802 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9024   -1.4813   -0.4915 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5948   -2.0705   -1.2346 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9231   -3.3792   -1.4511 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2031   -1.8135    0.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7569   -0.6708    0.6268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3394   -0.2617    1.9602 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2887    3.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9995   -2.5524    2.7014 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4546   -0.8197    4.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3461   -0.7751    3.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1271    0.0027    3.4007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2693    0.3108    1.9865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4729    0.6535    1.5614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7540    0.9398    0.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2554    2.3256   -0.0909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5246    2.6659    0.6275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6664    1.8483    0.2303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5981    0.9924   -0.6506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8838    2.0580    0.8885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0239    1.3181    0.5691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4172    1.4982   -0.8440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7173    2.2622   -1.5568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5762    0.8210   -1.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9059    1.0176   -2.7365 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0001    0.3843   -3.2926 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7670   -0.4464   -2.5288 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4372   -0.6412   -1.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3438   -0.0144   -0.6371 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9535    0.1654    1.0904 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9904    0.2092    2.1306 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1533    2.3108   -3.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3503    0.9645   -3.0778 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5729    1.3796   -4.6466 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6270   -2.4173   -3.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5008   -1.1111   -3.6272 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5475   -0.1162   -1.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7795   -2.5300   -0.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8363   -0.8378    0.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9132   -1.3178   -0.9104 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7889   -1.7872   -1.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7096   -4.0064   -0.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3156   -2.6337    0.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6892    0.1076   -0.1643 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0261    0.5913    2.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5108   -1.3322    3.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5249   -3.2842    3.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7865    0.1772    4.3981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3758   -1.5543    4.9096 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1664   -1.7511    2.6455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4151    0.9675    3.8794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6691   -0.5207    3.9536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2616    0.7220    2.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5136    0.2170   -0.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8484    0.7109   -0.5048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4619    3.0262    0.2717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3724    2.5685   -1.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7585    3.7256    0.3573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3729    2.5616    1.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7736    0.2360    0.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8727    1.6461    1.1908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2812    1.6785   -3.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2056    0.5802   -4.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6253   -0.9404   -2.9729 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0425   -1.2982   -0.6040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0640   -0.1513    0.3968 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9106   -0.7754    0.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9666    1.0719    0.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9161    1.1965    2.6444 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  3  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 17 34  1  0
 34 35  1  0
 35 11  1  0
 35 15  1  0
 33 28  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
  6 42  1  0
  6 43  1  0
  6 44  1  0
  7 45  1  0
  8 46  1  0
  9 47  1  0
 10 48  1  0
 11 49  1  0
 12 50  1  0
 13 51  1  0
 14 52  1  0
 14 53  1  0
 15 54  1  0
 16 55  1  0
 16 56  1  0
 18 57  1  0
 19 58  1  0
 19 59  1  0
 20 60  1  0
 20 61  1  0
 21 62  1  0
 21 63  1  0
 25 64  1  0
 25 65  1  0
 29 66  1  0
 30 67  1  0
 31 68  1  0
 32 69  1  0
 33 70  1  0
 34 71  1  0
 34 72  1  0
 35 73  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1088                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       9.594  -2.997   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      10.612   2.642   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      22.791   1.004   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      22.791  -1.664   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      24.331   3.671   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      13.504  -2.227   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.504  -3.767   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.040  -1.751   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.040  -4.243   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.134  -2.997   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.962  -1.758   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.962  -4.237   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.860  -2.997   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.564  -0.287   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.400  -2.997   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.057   0.033   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      18.170  -1.664   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.581   1.498   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      19.711  -1.664   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.075   1.818   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      20.481  -0.330   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.599   3.283   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.045   0.674   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      22.021  -0.330   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.093   3.603   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.586   3.923   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      24.331   1.004   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.080   4.243   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      25.101   2.337   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      26.641   2.337   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      27.411   3.671   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      27.411   1.004   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      28.951   3.671   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      28.951   1.004   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      29.721   2.337   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2   18                                                            
CONECT    3   24   27                                                       
CONECT    4   24                                                            
CONECT    5   29                                                            
CONECT    6    7    8   11                                                  
CONECT    7    6    9   12                                                  
CONECT    8    6   10   14                                                  
CONECT    9    7   10                                                       
CONECT   10    1    8    9                                                  
CONECT   11    6   13                                                       
CONECT   12    7   13                                                       
CONECT   13   11   12   15                                                  
CONECT   14    8   16                                                       
CONECT   15   13   17                                                       
CONECT   16   14   18                                                       
CONECT   17   15   19                                                       
CONECT   18    2   16   20                                                  
CONECT   19   17   21                                                       
CONECT   20   18   22   23                                                  
CONECT   21   19   24                                                       
CONECT   22   20   25                                                       
CONECT   23   20                                                            
CONECT   24    3    4   21                                                  
CONECT   25   22   26                                                       
CONECT   26   25   28                                                       
CONECT   27    3   29                                                       
CONECT   28   26                                                            
CONECT   29    5   27   30                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30   33                                                       
CONECT   32   30   34                                                       
CONECT   33   31   35                                                       
CONECT   34   32   35                                                       
CONECT   35   33   34                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

COMPND    HMDB0015220
HETATM    1  C1  UNL     1       9.406   1.307  -3.553  1.00  0.00           C  
HETATM    2  C2  UNL     1       8.309   0.356  -3.353  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.404  -0.426  -3.168  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.308  -1.364  -2.921  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.813  -1.205  -1.480  1.00  0.00           C  
HETATM    6  C6  UNL     1       6.902  -1.481  -0.492  1.00  0.00           C  
HETATM    7  C7  UNL     1       4.595  -2.071  -1.235  1.00  0.00           C  
HETATM    8  O1  UNL     1       4.923  -3.379  -1.451  1.00  0.00           O  
HETATM    9  C8  UNL     1       4.203  -1.814   0.201  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.757  -0.671   0.627  1.00  0.00           C  
HETATM   11  C10 UNL     1       3.339  -0.262   1.960  1.00  0.00           C  
HETATM   12  C11 UNL     1       3.522  -1.289   3.063  1.00  0.00           C  
HETATM   13  O2  UNL     1       3.000  -2.552   2.701  1.00  0.00           O  
HETATM   14  C12 UNL     1       2.455  -0.820   4.114  1.00  0.00           C  
HETATM   15  C13 UNL     1       1.346  -0.775   3.134  1.00  0.00           C  
HETATM   16  C14 UNL     1       0.127   0.003   3.401  1.00  0.00           C  
HETATM   17  C15 UNL     1      -0.269   0.311   1.987  1.00  0.00           C  
HETATM   18  C16 UNL     1      -1.473   0.653   1.561  1.00  0.00           C  
HETATM   19  C17 UNL     1      -1.754   0.940   0.115  1.00  0.00           C  
HETATM   20  C18 UNL     1      -2.255   2.326  -0.091  1.00  0.00           C  
HETATM   21  C19 UNL     1      -3.525   2.666   0.627  1.00  0.00           C  
HETATM   22  C20 UNL     1      -4.666   1.848   0.230  1.00  0.00           C  
HETATM   23  O3  UNL     1      -4.598   0.992  -0.651  1.00  0.00           O  
HETATM   24  O4  UNL     1      -5.884   2.058   0.888  1.00  0.00           O  
HETATM   25  C21 UNL     1      -7.024   1.318   0.569  1.00  0.00           C  
HETATM   26  C22 UNL     1      -7.417   1.498  -0.844  1.00  0.00           C  
HETATM   27  O5  UNL     1      -6.717   2.262  -1.557  1.00  0.00           O  
HETATM   28  C23 UNL     1      -8.576   0.821  -1.413  1.00  0.00           C  
HETATM   29  C24 UNL     1      -8.906   1.018  -2.736  1.00  0.00           C  
HETATM   30  C25 UNL     1     -10.000   0.384  -3.293  1.00  0.00           C  
HETATM   31  C26 UNL     1     -10.767  -0.446  -2.529  1.00  0.00           C  
HETATM   32  C27 UNL     1     -10.437  -0.641  -1.211  1.00  0.00           C  
HETATM   33  C28 UNL     1      -9.344  -0.014  -0.637  1.00  0.00           C  
HETATM   34  C29 UNL     1       0.953   0.165   1.090  1.00  0.00           C  
HETATM   35  C30 UNL     1       1.990   0.209   2.131  1.00  0.00           C  
HETATM   36  H1  UNL     1       9.153   2.311  -3.147  1.00  0.00           H  
HETATM   37  H2  UNL     1      10.350   0.964  -3.078  1.00  0.00           H  
HETATM   38  H3  UNL     1       9.573   1.380  -4.647  1.00  0.00           H  
HETATM   39  H4  UNL     1       6.627  -2.417  -3.070  1.00  0.00           H  
HETATM   40  H5  UNL     1       5.501  -1.111  -3.627  1.00  0.00           H  
HETATM   41  H6  UNL     1       5.547  -0.116  -1.387  1.00  0.00           H  
HETATM   42  H7  UNL     1       6.780  -2.530  -0.114  1.00  0.00           H  
HETATM   43  H8  UNL     1       6.836  -0.838   0.422  1.00  0.00           H  
HETATM   44  H9  UNL     1       7.913  -1.318  -0.910  1.00  0.00           H  
HETATM   45  H10 UNL     1       3.789  -1.787  -1.929  1.00  0.00           H  
HETATM   46  H11 UNL     1       4.710  -4.006  -0.744  1.00  0.00           H  
HETATM   47  H12 UNL     1       4.316  -2.634   0.887  1.00  0.00           H  
HETATM   48  H13 UNL     1       3.689   0.108  -0.164  1.00  0.00           H  
HETATM   49  H14 UNL     1       4.026   0.591   2.309  1.00  0.00           H  
HETATM   50  H15 UNL     1       4.511  -1.332   3.495  1.00  0.00           H  
HETATM   51  H16 UNL     1       3.525  -3.284   3.087  1.00  0.00           H  
HETATM   52  H17 UNL     1       2.786   0.177   4.398  1.00  0.00           H  
HETATM   53  H18 UNL     1       2.376  -1.554   4.910  1.00  0.00           H  
HETATM   54  H19 UNL     1       1.166  -1.751   2.645  1.00  0.00           H  
HETATM   55  H20 UNL     1       0.415   0.968   3.879  1.00  0.00           H  
HETATM   56  H21 UNL     1      -0.669  -0.521   3.954  1.00  0.00           H  
HETATM   57  H22 UNL     1      -2.262   0.722   2.299  1.00  0.00           H  
HETATM   58  H23 UNL     1      -2.514   0.217  -0.213  1.00  0.00           H  
HETATM   59  H24 UNL     1      -0.848   0.711  -0.505  1.00  0.00           H  
HETATM   60  H25 UNL     1      -1.462   3.026   0.272  1.00  0.00           H  
HETATM   61  H26 UNL     1      -2.372   2.568  -1.175  1.00  0.00           H  
HETATM   62  H27 UNL     1      -3.759   3.726   0.357  1.00  0.00           H  
HETATM   63  H28 UNL     1      -3.373   2.562   1.728  1.00  0.00           H  
HETATM   64  H29 UNL     1      -6.774   0.236   0.764  1.00  0.00           H  
HETATM   65  H30 UNL     1      -7.873   1.646   1.191  1.00  0.00           H  
HETATM   66  H31 UNL     1      -8.281   1.678  -3.312  1.00  0.00           H  
HETATM   67  H32 UNL     1     -10.206   0.580  -4.337  1.00  0.00           H  
HETATM   68  H33 UNL     1     -11.625  -0.940  -2.973  1.00  0.00           H  
HETATM   69  H34 UNL     1     -11.043  -1.298  -0.604  1.00  0.00           H  
HETATM   70  H35 UNL     1      -9.064  -0.151   0.397  1.00  0.00           H  
HETATM   71  H36 UNL     1       0.911  -0.775   0.524  1.00  0.00           H  
HETATM   72  H37 UNL     1       0.967   1.072   0.467  1.00  0.00           H  
HETATM   73  H38 UNL     1       1.916   1.196   2.644  1.00  0.00           H  
CONECT    1    2   36   37   38
CONECT    2    3    3    3
CONECT    3    4
CONECT    4    5   39   40
CONECT    5    6    7   41
CONECT    6   42   43   44
CONECT    7    8    9   45
CONECT    8   46
CONECT    9   10   10   47
CONECT   10   11   48
CONECT   11   12   35   49
CONECT   12   13   14   50
CONECT   13   51
CONECT   14   15   52   53
CONECT   15   16   35   54
CONECT   16   17   55   56
CONECT   17   18   18   34
CONECT   18   19   57
CONECT   19   20   58   59
CONECT   20   21   60   61
CONECT   21   22   62   63
CONECT   22   23   23   24
CONECT   24   25
CONECT   25   26   64   65
CONECT   26   27   27   28
CONECT   28   29   29   33
CONECT   29   30   66
CONECT   30   31   31   67
CONECT   31   32   68
CONECT   32   33   33   69
CONECT   33   70
CONECT   34   35   71   72
CONECT   35   73
END

HMDB0015220
     RDKit          3D
Iloprost
 73 75  0  0  0  0  0  0  0  0999 V2000
    9.4062    1.3075   -3.5526 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3093    0.3557   -3.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4039   -0.4265   -3.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3080   -1.3637   -2.9206 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8133   -1.2051   -1.4802 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9024   -1.4813   -0.4915 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5948   -2.0705   -1.2346 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9231   -3.3792   -1.4511 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2031   -1.8135    0.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7569   -0.6708    0.6268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3394   -0.2617    1.9602 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2887    3.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9995   -2.5524    2.7014 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4546   -0.8197    4.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3461   -0.7751    3.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1271    0.0027    3.4007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2693    0.3108    1.9865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4729    0.6535    1.5614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7540    0.9398    0.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2554    2.3256   -0.0909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5246    2.6659    0.6275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6664    1.8483    0.2303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5981    0.9924   -0.6506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8838    2.0580    0.8885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0239    1.3181    0.5691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4172    1.4982   -0.8440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7173    2.2622   -1.5568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5762    0.8210   -1.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9059    1.0176   -2.7365 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0001    0.3843   -3.2926 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7670   -0.4464   -2.5288 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4372   -0.6412   -1.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3438   -0.0144   -0.6371 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9535    0.1654    1.0904 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9904    0.2092    2.1306 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1533    2.3108   -3.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3503    0.9645   -3.0778 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5729    1.3796   -4.6466 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6270   -2.4173   -3.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5008   -1.1111   -3.6272 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5475   -0.1162   -1.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7795   -2.5300   -0.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8363   -0.8378    0.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9132   -1.3178   -0.9104 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7889   -1.7872   -1.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7096   -4.0064   -0.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3156   -2.6337    0.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6892    0.1076   -0.1643 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0261    0.5913    2.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5108   -1.3322    3.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5249   -3.2842    3.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7865    0.1772    4.3981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3758   -1.5543    4.9096 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1664   -1.7511    2.6455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4151    0.9675    3.8794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6691   -0.5207    3.9536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2616    0.7220    2.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5136    0.2170   -0.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8484    0.7109   -0.5048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4619    3.0262    0.2717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3724    2.5685   -1.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7585    3.7256    0.3573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3729    2.5616    1.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7736    0.2360    0.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8727    1.6461    1.1908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2812    1.6785   -3.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2056    0.5802   -4.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6253   -0.9404   -2.9729 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0425   -1.2982   -0.6040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0640   -0.1513    0.3968 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9106   -0.7754    0.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9666    1.0719    0.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9161    1.1965    2.6444 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  3  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 17 34  1  0
 34 35  1  0
 35 11  1  0
 35 15  1  0
 33 28  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
  6 42  1  0
  6 43  1  0
  6 44  1  0
  7 45  1  0
  8 46  1  0
  9 47  1  0
 10 48  1  0
 11 49  1  0
 12 50  1  0
 13 51  1  0
 14 52  1  0
 14 53  1  0
 15 54  1  0
 16 55  1  0
 16 56  1  0
 18 57  1  0
 19 58  1  0
 19 59  1  0
 20 60  1  0
 20 61  1  0
 21 62  1  0
 21 63  1  0
 25 64  1  0
 25 65  1  0
 29 66  1  0
 30 67  1  0
 31 68  1  0
 32 69  1  0
 33 70  1  0
 34 71  1  0
 34 72  1  0
 35 73  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Iloprost-pe	HMDB
2-oxo-2-Phenylethyl 5-[(2Z)-5-hydroxy-4-[(1E)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl]-octahydropentalen-2-ylidene]pentanoic acid	HMDB
Iloprost phenacyl ester	HMDB

Chemical Formula

C₃₀H₃₈O₅

Average Molecular Weight

478.6197

Monoisotopic Molecular Weight

478.271924326

IUPAC Name

2-oxo-2-phenylethyl 5-[(2Z)-5-hydroxy-4-[(1E)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl]-octahydropentalen-2-ylidene]pentanoate

Traditional Name

iloprost

CAS Registry Number

78919-13-8

SMILES

CC#CCC(C)C(O)\C=C\C1C(O)CC2C\C(CC12)=C\CCCC(=O)OCC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C30H38O5/c1-3-4-10-21(2)27(31)16-15-25-26-18-22(17-24(26)19-28(25)32)11-8-9-14-30(34)35-20-29(33)23-12-6-5-7-13-23/h5-7,11-13,15-16,21,24-28,31-32H,8-10,14,17-20H2,1-2H3/b16-15+,22-11-

InChI Key

CZUMMMDKQYRZDP-JCAXBLPDSA-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
Alkyl-phenylketone
Aromatic monoterpenoid
Monoterpenoid
Bicyclic monoterpenoid
Phenylketone
Fatty alcohol
Benzoyl
Aryl alkyl ketone
Aryl ketone
Fatty acid ester
Alpha-acyloxy ketone
Monocyclic benzene moiety
Benzenoid
Cyclic alcohol
Ketone
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

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

Source

Exogenous

Exogenous (HMDB: HMDB0015220)

Process

Not Available

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	0.002 g/L	Not Available
LogP	4.8	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.002 g/L	ALOGPS
logP	5.04	ALOGPS
logP	4.94	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	13.72	ChemAxon
pKa (Strongest Basic)	-0.87	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	139.85 m³·mol⁻¹	ChemAxon
Polarizability	55.4 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	215.505	31661259
DarkChem	[M-H]-	213.255	31661259
DeepCCS	[M-2H]-	243.208	30932474
DeepCCS	[M+Na]+	218.773	30932474
AllCCS	[M+H]+	223.7	32859911
AllCCS	[M+H-H2O]+	221.8	32859911
AllCCS	[M+NH4]+	225.4	32859911
AllCCS	[M+Na]+	225.9	32859911
AllCCS	[M-H]-	215.9	32859911
AllCCS	[M+Na-2H]-	218.3	32859911
AllCCS	[M+HCOO]-	221.2	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.	8.47 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.	8.16 minutes	32390414
Predicted by Siyang on May 30, 2022	17.5803 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.51 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	46.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3343.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	272.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	238.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	181.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	252.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	801.4 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	707.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	86.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1556.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	665.2 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	1729.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	477.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	453.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	222.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	298.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Iloprost	CC#CCC(C)C(O)\C=C\C1C(O)CC2C\C(CC12)=C\CCCC(=O)OCC(=O)C1=CC=CC=C1	4801.0	Standard polar	33892256
Iloprost	CC#CCC(C)C(O)\C=C\C1C(O)CC2C\C(CC12)=C\CCCC(=O)OCC(=O)C1=CC=CC=C1	3438.1	Standard non polar	33892256
Iloprost	CC#CCC(C)C(O)\C=C\C1C(O)CC2C\C(CC12)=C\CCCC(=O)OCC(=O)C1=CC=CC=C1	3910.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Iloprost,1TMS,isomer #1	CC#CCC(C)C(/C=C/C1C(O)CC2C/C(=C/CCCC(=O)OCC(=O)C3=CC=CC=C3)CC21)O[Si](C)(C)C	3960.3	Semi standard non polar	33892256
Iloprost,1TMS,isomer #2	CC#CCC(C)C(O)/C=C/C1C(O[Si](C)(C)C)CC2C/C(=C/CCCC(=O)OCC(=O)C3=CC=CC=C3)CC21	3895.7	Semi standard non polar	33892256
Iloprost,2TMS,isomer #1	CC#CCC(C)C(/C=C/C1C(O[Si](C)(C)C)CC2C/C(=C/CCCC(=O)OCC(=O)C3=CC=CC=C3)CC21)O[Si](C)(C)C	3835.6	Semi standard non polar	33892256
Iloprost,1TBDMS,isomer #1	CC#CCC(C)C(/C=C/C1C(O)CC2C/C(=C/CCCC(=O)OCC(=O)C3=CC=CC=C3)CC21)O[Si](C)(C)C(C)(C)C	4186.1	Semi standard non polar	33892256
Iloprost,1TBDMS,isomer #2	CC#CCC(C)C(O)/C=C/C1C(O[Si](C)(C)C(C)(C)C)CC2C/C(=C/CCCC(=O)OCC(=O)C3=CC=CC=C3)CC21	4126.1	Semi standard non polar	33892256
Iloprost,2TBDMS,isomer #1	CC#CCC(C)C(/C=C/C1C(O[Si](C)(C)C(C)(C)C)CC2C/C(=C/CCCC(=O)OCC(=O)C3=CC=CC=C3)CC21)O[Si](C)(C)C(C)(C)C	4269.9	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 - Iloprost GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-3953200000-b443b1bda7d785ac5d30	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Iloprost GC-MS (2 TMS) - 70eV, Positive	splash10-0a4i-1900210000-4e1ef34a133a2751758b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Iloprost GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Iloprost 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 - Iloprost 10V, Positive-QTOF	splash10-03fu-0002900000-6a96f6c0e27208aa18ae	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iloprost 20V, Positive-QTOF	splash10-01yc-5455900000-87ae1678bc484e678de9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iloprost 40V, Positive-QTOF	splash10-057i-9483100000-98e240ce9fc267005932	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iloprost 10V, Negative-QTOF	splash10-004l-0105900000-bd6afd767ba75381c69a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iloprost 20V, Negative-QTOF	splash10-056u-5509500000-2084dc240e0f75394853	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iloprost 40V, Negative-QTOF	splash10-004i-9413000000-b2178e58ccb54de33168	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iloprost 10V, Positive-QTOF	splash10-004i-0017900000-5e1366159937b37e0b05	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iloprost 20V, Positive-QTOF	splash10-0aor-5308900000-271908350c9d4b1e9c90	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iloprost 40V, Positive-QTOF	splash10-0udu-9204300000-168e9fb8385284dbfa8a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iloprost 10V, Negative-QTOF	splash10-056r-0102900000-10e1eb3ea58023970cd4	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iloprost 20V, Negative-QTOF	splash10-014i-7903300000-97e90a9cce893500efab	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iloprost 40V, Negative-QTOF	splash10-054k-7194400000-f7eb359410db7895850e	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
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 DB01088	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01088	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

4947911

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Iloprost

METLIN ID

Not Available

PubChem Compound

6443959

PDB ID

Not Available

ChEBI ID

Not Available

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. cAMP-specific 3',5'-cyclic phosphodiesterase 4B

General function:: Involved in catalytic activity
Specific function:: Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes. May be involved in mediating central nervous system effects of therapeutic agents ranging from antidepressants to antiasthmatic and anti-inflammatory agents.
Gene Name:: PDE4B
Uniprot ID:: Q07343
Molecular weight:: 64351.765

References

Wilkens H, Guth A, Konig J, Forestier N, Cremers B, Hennen B, Bohm M, Sybrecht GW: Effect of inhaled iloprost plus oral sildenafil in patients with primary pulmonary hypertension. Circulation. 2001 Sep 11;104(11):1218-22. [PubMed:11551870 ]
Ghofrani HA, Rose F, Schermuly RT, Olschewski H, Wiedemann R, Weissmann N, Schudt C, Tenor H, Seeger W, Grimminger F: Amplification of the pulmonary vasodilatory response to inhaled iloprost by subthreshold phosphodiesterase types 3 and 4 inhibition in severe pulmonary hypertension. Crit Care Med. 2002 Nov;30(11):2489-92. [PubMed:12441759 ]
Schermuly RT, Leuchte H, Ghofrani HA, Weissmann N, Rose F, Kohstall M, Olschewski H, Schudt C, Grimminger F, Seeger W, Walmrath D: Zardaverine and aerosolised iloprost in a model of acute respiratory failure. Eur Respir J. 2003 Aug;22(2):342-7. [PubMed:12952271 ]
Grant PG, Mannarino AF, Colman RW: cAMP-mediated phosphorylation of the low-Km cAMP phosphodiesterase markedly stimulates its catalytic activity. Proc Natl Acad Sci U S A. 1988 Dec;85(23):9071-5. [PubMed:2461561 ]

Enzyme Details

2. cAMP-specific 3',5'-cyclic phosphodiesterase 4C

General function:: Involved in catalytic activity
Specific function:: Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
Gene Name:: PDE4C
Uniprot ID:: Q08493
Molecular weight:: 79900.795

References

Wilkens H, Guth A, Konig J, Forestier N, Cremers B, Hennen B, Bohm M, Sybrecht GW: Effect of inhaled iloprost plus oral sildenafil in patients with primary pulmonary hypertension. Circulation. 2001 Sep 11;104(11):1218-22. [PubMed:11551870 ]
Ghofrani HA, Rose F, Schermuly RT, Olschewski H, Wiedemann R, Weissmann N, Schudt C, Tenor H, Seeger W, Grimminger F: Amplification of the pulmonary vasodilatory response to inhaled iloprost by subthreshold phosphodiesterase types 3 and 4 inhibition in severe pulmonary hypertension. Crit Care Med. 2002 Nov;30(11):2489-92. [PubMed:12441759 ]
Schermuly RT, Leuchte H, Ghofrani HA, Weissmann N, Rose F, Kohstall M, Olschewski H, Schudt C, Grimminger F, Seeger W, Walmrath D: Zardaverine and aerosolised iloprost in a model of acute respiratory failure. Eur Respir J. 2003 Aug;22(2):342-7. [PubMed:12952271 ]
Grant PG, Mannarino AF, Colman RW: cAMP-mediated phosphorylation of the low-Km cAMP phosphodiesterase markedly stimulates its catalytic activity. Proc Natl Acad Sci U S A. 1988 Dec;85(23):9071-5. [PubMed:2461561 ]

Enzyme Details

3. cAMP-specific 3',5'-cyclic phosphodiesterase 4D

General function:: Involved in catalytic activity
Specific function:: Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
Gene Name:: PDE4D
Uniprot ID:: Q08499
Molecular weight:: 91114.1

References

Wilkens H, Guth A, Konig J, Forestier N, Cremers B, Hennen B, Bohm M, Sybrecht GW: Effect of inhaled iloprost plus oral sildenafil in patients with primary pulmonary hypertension. Circulation. 2001 Sep 11;104(11):1218-22. [PubMed:11551870 ]
Ghofrani HA, Rose F, Schermuly RT, Olschewski H, Wiedemann R, Weissmann N, Schudt C, Tenor H, Seeger W, Grimminger F: Amplification of the pulmonary vasodilatory response to inhaled iloprost by subthreshold phosphodiesterase types 3 and 4 inhibition in severe pulmonary hypertension. Crit Care Med. 2002 Nov;30(11):2489-92. [PubMed:12441759 ]
Schermuly RT, Leuchte H, Ghofrani HA, Weissmann N, Rose F, Kohstall M, Olschewski H, Schudt C, Grimminger F, Seeger W, Walmrath D: Zardaverine and aerosolised iloprost in a model of acute respiratory failure. Eur Respir J. 2003 Aug;22(2):342-7. [PubMed:12952271 ]
Grant PG, Mannarino AF, Colman RW: cAMP-mediated phosphorylation of the low-Km cAMP phosphodiesterase markedly stimulates its catalytic activity. Proc Natl Acad Sci U S A. 1988 Dec;85(23):9071-5. [PubMed:2461561 ]

Enzyme Details

4. cAMP-specific 3',5'-cyclic phosphodiesterase 4A

General function:: Involved in 3',5'-cyclic-nucleotide phosphodiesterase activity
Specific function:: Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
Gene Name:: PDE4A
Uniprot ID:: P27815
Molecular weight:: 98142.155

References

Wilkens H, Guth A, Konig J, Forestier N, Cremers B, Hennen B, Bohm M, Sybrecht GW: Effect of inhaled iloprost plus oral sildenafil in patients with primary pulmonary hypertension. Circulation. 2001 Sep 11;104(11):1218-22. [PubMed:11551870 ]
Ghofrani HA, Rose F, Schermuly RT, Olschewski H, Wiedemann R, Weissmann N, Schudt C, Tenor H, Seeger W, Grimminger F: Amplification of the pulmonary vasodilatory response to inhaled iloprost by subthreshold phosphodiesterase types 3 and 4 inhibition in severe pulmonary hypertension. Crit Care Med. 2002 Nov;30(11):2489-92. [PubMed:12441759 ]
Schermuly RT, Leuchte H, Ghofrani HA, Weissmann N, Rose F, Kohstall M, Olschewski H, Schudt C, Grimminger F, Seeger W, Walmrath D: Zardaverine and aerosolised iloprost in a model of acute respiratory failure. Eur Respir J. 2003 Aug;22(2):342-7. [PubMed:12952271 ]
Grant PG, Mannarino AF, Colman RW: cAMP-mediated phosphorylation of the low-Km cAMP phosphodiesterase markedly stimulates its catalytic activity. Proc Natl Acad Sci U S A. 1988 Dec;85(23):9071-5. [PubMed:2461561 ]

Enzyme Details

5. Tissue-type plasminogen activator

General function:: Involved in serine-type endopeptidase activity
Specific function:: Converts the abundant, but inactive, zymogen plasminogen to plasmin by hydrolyzing a single Arg-Val bond in plasminogen. By controlling plasmin-mediated proteolysis, it plays an important role in tissue remodeling and degradation, in cell migration and many other physiopathological events. Play a direct role in facilitating neuronal migration
Gene Name:: PLAT
Uniprot ID:: P00750
Molecular weight:: 62916.5

References

Kerins DM, Roy L, Kunitada S, Adedoyin A, FitzGerald GA, Fitzgerald DJ: Pharmacokinetics of tissue-type plasminogen activator during acute myocardial infarction in men. Effect of a prostacyclin analogue. Circulation. 1992 Feb;85(2):526-32. [PubMed:1370924 ]
Nicolini FA, Mehta JL, Nichols WW, Saldeen TG, Grant M: Prostacyclin analogue iloprost decreases thrombolytic potential of tissue-type plasminogen activator in canine coronary thrombosis. Circulation. 1990 Mar;81(3):1115-22. [PubMed:1689620 ]
Nichols WW, Nicolini FA, Saldeen TG, Mehta JL: Combined thrombolytic effects of tissue-plasminogen activator and a fibrinogen-degradation product peptide 6A or iloprost. J Cardiovasc Pharmacol. 1991 Aug;18(2):231-6. [PubMed:1717784 ]
Nizankowski R, Krzanowski M, Musial J, Szczeklik A: [Effect of thromboxane A2 synthetase inhibitor and prostacyclin analogue on arterial blood pressure, fibrinolysis and platelet function in patients with hypertension]. Pol Tyg Lek. 1991 Jan 7-14;46(1-3):18-21. [PubMed:1726988 ]
Herczenik E, Bouma B, Korporaal SJ, Strangi R, Zeng Q, Gros P, Van Eck M, Van Berkel TJ, Gebbink MF, Akkerman JW: Activation of human platelets by misfolded proteins. Arterioscler Thromb Vasc Biol. 2007 Jul;27(7):1657-65. Epub 2007 May 17. [PubMed:17510465 ]

Enzyme Details

6. Prostaglandin E2 receptor EP1 subtype

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Receptor for prostaglandin E2 (PGE2). The activity of this receptor is mediated by G(q) proteins which activate a phosphatidylinositol-calcium second messenger system. May play a role as an important modulator of renal function. Implicated the smooth muscle contractile response to PGE2 in various tissues
Gene Name:: PTGER1
Uniprot ID:: P34995
Molecular weight:: 41800.7

References

Sharif NA, Davis TL: Cloned human EP1 prostanoid receptor pharmacology characterized using radioligand binding techniques. J Pharm Pharmacol. 2002 Apr;54(4):539-47. [PubMed:11999132 ]
Walch L, de Montpreville V, Brink C, Norel X: Prostanoid EP(1)- and TP-receptors involved in the contraction of human pulmonary veins. Br J Pharmacol. 2001 Dec;134(8):1671-8. [PubMed:11739243 ]

Enzyme Details

7. Prostacyclin receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Receptor for prostacyclin (prostaglandin I2 or PGI2). The activity of this receptor is mediated by G(s) proteins which activate adenylate cyclase
Gene Name:: PTGIR
Uniprot ID:: P43119
Molecular weight:: 40955.5

References

Takamatsu H, Tsukada H, Watanabe Y, Cui Y, Kataoka Y, Hosoya T, Suzuki M, Watanabe Y: Specific ligand for a central type prostacyclin receptor attenuates neuronal damage in a rat model of focal cerebral ischemia. Brain Res. 2002 Jan 25;925(2):176-82. [PubMed:11792366 ]
Crutchley DJ, Solomon DE, Conanan LB: Prostacyclin analogues inhibit tissue factor expression in the human monocytic cell line THP-1 via a cyclic AMP-dependent mechanism. Arterioscler Thromb. 1992 Jun;12(6):664-70. [PubMed:1375507 ]
Schermuly RT, Pullamsetti SS, Breitenbach SC, Weissmann N, Ghofrani HA, Grimminger F, Nilius SM, Schror K, Kirchrath JM, Seeger W, Rose F: Iloprost-induced desensitization of the prostacyclin receptor in isolated rabbit lungs. Respir Res. 2007 Jan 26;8:4. [PubMed:17257398 ]
Idzko M, Hammad H, van Nimwegen M, Kool M, Vos N, Hoogsteden HC, Lambrecht BN: Inhaled iloprost suppresses the cardinal features of asthma via inhibition of airway dendritic cell function. J Clin Invest. 2007 Feb;117(2):464-72. [PubMed:17273558 ]
Tsai AL, Vijjeswarapu H, Wu KK: Interaction between platelet receptor and iloprost isomers. Biochim Biophys Acta. 1988 Jul 21;942(2):220-6. [PubMed:2456096 ]
Olschewski H, Rose F, Schermuly R, Ghofrani HA, Enke B, Olschewski A, Seeger W: Prostacyclin and its analogues in the treatment of pulmonary hypertension. Pharmacol Ther. 2004 May;102(2):139-53. [PubMed:15163595 ]
Anderson JR, Nawarskas JJ: Pharmacotherapeutic management of pulmonary arterial hypertension. Cardiol Rev. 2010 May-Jun;18(3):148-62. doi: 10.1097/CRD.0b013e3181d4e921. [PubMed:20395700 ]
Mubarak KK: A review of prostaglandin analogs in the management of patients with pulmonary arterial hypertension. Respir Med. 2010 Jan;104(1):9-21. doi: 10.1016/j.rmed.2009.07.015. Epub 2009 Aug 15. [PubMed:19683911 ]
Krug S, Sablotzki A, Hammerschmidt S, Wirtz H, Seyfarth HJ: Inhaled iloprost for the control of pulmonary hypertension. Vasc Health Risk Manag. 2009;5(1):465-74. [PubMed:19475782 ]

Transporters

Enzyme Details

1. Solute carrier organic anion transporter family member 2B1

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost
Gene Name:: SLCO2B1
Uniprot ID:: O94956
Molecular weight:: 76697.9

References

Nishio T, Adachi H, Nakagomi R, Tokui T, Sato E, Tanemoto M, Fujiwara K, Okabe M, Onogawa T, Suzuki T, Nakai D, Shiiba K, Suzuki M, Ohtani H, Kondo Y, Unno M, Ito S, Iinuma K, Nunoki K, Matsuno S, Abe T: Molecular identification of a rat novel organic anion transporter moat1, which transports prostaglandin D(2), leukotriene C(4), and taurocholate. Biochem Biophys Res Commun. 2000 Sep 7;275(3):831-8. [PubMed:10973807 ]

Enzyme Details

2. Solute carrier organic anion transporter family member 2A1

General function:: Not Available
Specific function:: May mediate the release of newly synthesized prostaglandins from cells, the transepithelial transport of prostaglandins, and the clearance of prostaglandins from the circulation. Transports PGD2, as well as PGE1, PGE2 and PGF2A
Gene Name:: SLCO2A1
Uniprot ID:: Q92959
Molecular weight:: 70117.0

References

Lu R, Kanai N, Bao Y, Schuster VL: Cloning, in vitro expression, and tissue distribution of a human prostaglandin transporter cDNA(hPGT). J Clin Invest. 1996 Sep 1;98(5):1142-9. [PubMed:8787677 ]
Kanai N, Lu R, Satriano JA, Bao Y, Wolkoff AW, Schuster VL: Identification and characterization of a prostaglandin transporter. Science. 1995 May 12;268(5212):866-9. [PubMed:7754369 ]

Enzyme Details

3. Solute carrier organic anion transporter family member 3A1

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as estrone-3-sulfate (PubMed:10873595). Mediates transport of prostaglandins (PG) E1 and E2, thyroxine (T4), deltorphin II, BQ-123 and vasopressin, but not DPDPE (a derivative of enkephalin lacking an N-terminal tyrosine residue), estrone-3- sulfate, taurocholate, digoxin nor DHEAS (PubMed:16971491)
Gene Name:: SLCO3A1
Uniprot ID:: Q9UIG8
Molecular weight:: 76552.1

References

Adachi H, Suzuki T, Abe M, Asano N, Mizutamari H, Tanemoto M, Nishio T, Onogawa T, Toyohara T, Kasai S, Satoh F, Suzuki M, Tokui T, Unno M, Shimosegawa T, Matsuno S, Ito S, Abe T: Molecular characterization of human and rat organic anion transporter OATP-D. Am J Physiol Renal Physiol. 2003 Dec;285(6):F1188-97. [PubMed:14631946 ]

Showing metabocard for Iloprost (HMDB0015220)

MOL for HMDB0015220 (Iloprost)

3D MOL for HMDB0015220 (Iloprost)

3D SDF for HMDB0015220 (Iloprost)

3D-SDF for HMDB0015220 (Iloprost)

PDB for HMDB0015220 (Iloprost)

3D PDB for HMDB0015220 (Iloprost)

SMILES for HMDB0015220 (Iloprost)

INCHI for HMDB0015220 (Iloprost)

Structure for HMDB0015220 (Iloprost)

3D Structure for HMDB0015220 (Iloprost)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

References

Transporters

References

References

References