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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:09 UTC

HMDB ID

HMDB0001335

Secondary Accession Numbers

HMDB01335

Metabolite Identification

Common Name

Prostaglandin I2

Description

Prostaglandin I2 or prostacyclin (or PGI2) is a member of the family of lipid molecules known as eicosanoids. It is produced in endothelial cells from prostaglandin H2 (PGH2) by the action of the enzyme prostacyclin synthase. It is a powerful vasodilator and inhibits platelet aggregation. Prostaglandin I2 is the main prostaglandin synthesized by the blood vessel wall. This suggests that it may play an important role in limiting platelet-mediated thrombosis. In particular, prostacyclin (PGI2) chiefly prevents formation of the platelet plug involved in primary hemostasis (a part of blood clot formation). The sodium salt (known as epoprostenol) has been used to treat primary pulmonary hypertension. Prostacyclin (PGI2) is released by healthy endothelial cells and performs its function through a paracrine signaling cascade that involves G protein-coupled receptors on nearby platelets and endothelial cells. The platelet Gs protein-coupled receptor (prostacyclin receptor) is activated when it binds to PGI2. This activation, in turn, signals adenylyl cyclase to produce cAMP. cAMP goes on to inhibit any undue platelet activation (in order to promote circulation) and also counteracts any increase in cytosolic calcium levels which would result from thromboxane A2 (TXA2) binding (leading to platelet activation and subsequent coagulation). PGI2 also binds to endothelial prostacyclin receptors and in the same manner raise cAMP levels in the cytosol. This cAMP then goes on to activate protein kinase A (PKA). PKA then continues the cascade by inhibiting myosin light-chain kinase which leads to smooth muscle relaxation and vasodilation. Notably, PGI2 and TXA2 work as antagonists. PGI2 is stable in basic buffers (pH=8), but it is rapidly hydrolyzed to 6-keto PGF1alpha in neutral or acidic solutions. The half-life is short both in vivo and in vitro, ranging from 30 seconds to a few minutes. PGI2 is administered by continuous infusion in humans for the treatment of idiopathic pulmonary hypertension.Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways.

Structure

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

HMDB0001335
     RDKit          3D
Prostaglandin I2
 57 58  0  0  0  0  0  0  0  0999 V2000
   -7.6138   -0.3843    1.3345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0215    0.2175    0.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8245   -0.5175   -0.4288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6858   -0.5997    0.5176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0997    0.6778    0.9886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5363    1.5420   -0.1040 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4509    1.9349   -1.0593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3257    0.9159   -0.7367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2898    0.6709    0.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0248    0.0537   -0.4581 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0124    0.0269   -1.9760 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7278   -1.0069   -2.5020 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4926   -0.1157   -2.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1185    0.7819   -1.2359 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1346    0.1393   -0.4910 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1392    0.5204    0.8216 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1145    0.6619    1.6902 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5369    0.3992    1.3435 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7317   -0.0243   -0.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1878   -0.2718   -0.3450 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6877   -1.3859    0.4704 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9068   -2.0719    1.1643 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0450   -1.7210    0.5030 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6930    0.7818    1.1555 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0886    1.0691   -0.1747 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.6669    0.4348    2.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6572   -0.7302    1.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0439   -1.1967    1.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8112    0.1549   -0.7056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7880    1.2814    0.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1341   -1.5630   -0.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5169   -0.0659   -1.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8957   -1.3011    1.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8560   -1.1408   -0.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2289    0.4096    1.6515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7891    1.2863    1.6117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1832    2.4842    0.4152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2333    2.8181   -1.4490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2755    0.6636   -1.7871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3446    0.9258    1.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1841   -0.9303   -0.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3313    1.0075   -2.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2411   -1.8684   -2.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7191    0.2092   -3.3051 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8194   -1.1698   -2.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5423    1.7035   -1.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8952    0.9841    2.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9482   -0.3046    2.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0955    1.3580    1.5080 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1562   -0.9689   -0.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3386    0.7860   -0.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2845   -0.4702   -1.4387 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7267    0.6631   -0.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4379   -1.8673    1.4199 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2254   -0.0940    1.6191 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6229    1.6943    1.7905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7123    2.0871   -0.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  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
 15 16  1  0
 16 17  2  3
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 16 24  1  0
 24 25  1  0
 25 10  1  0
 25 14  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  1
  7 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  1
 11 42  1  6
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  6
 17 47  1  0
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 23 54  1  0
 24 55  1  0
 24 56  1  0
 25 57  1  1
M  END

 
  Mrv0541 02231219042D          
 
 25 26  0  0  0  0            999 V2000
    6.5528   -6.7485    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7722   -6.4987    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5494   -7.5743    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9692   -6.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7653   -5.6522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2934   -7.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7826   -7.8311    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2641   -7.9803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5390   -5.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5190   -8.6360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9719   -7.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2710   -4.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6797   -7.9803    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.3875   -7.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6797   -8.7957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0953   -7.9803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8135   -7.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5109   -7.9803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2291   -7.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2775   -4.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9997   -3.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9970   -2.7671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7146   -2.3498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4372   -2.7639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7119   -1.5219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  6  0  0  0
  2  5  1  6  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  1  0  0  0
  4  9  1  0  0  0  0
  7 10  1  6  0  0  0
  8 11  2  0  0  0  0
  9 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  5  9  1  0  0  0  0
  6  7  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001335

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@@H]2OC(C[C@H]12)=CCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O5/c1-2-3-4-7-14(21)10-11-16-17-12-15(8-5-6-9-20(23)24)25-19(17)13-18(16)22/h8,10-11,14,16-19,21-22H,2-7,9,12-13H2,1H3,(H,23,24)/b11-10+,15-8-/t14-,16+,17+,18+,19-/m0/s1

> <INCHI_KEY>
KAQKFAOMNZTLHT-OZUDYXHBSA-N

> <FORMULA>
C20H32O5

> <MOLECULAR_WEIGHT>
352.4651

> <EXACT_MASS>
352.224974134

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
41.46702176830266

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(3aR,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-hexahydro-2H-cyclopenta[b]furan-2-ylidene]pentanoic acid

> <ALOGPS_LOGP>
3.83

> <JCHEM_LOGP>
2.415704516333332

> <ALOGPS_LOGS>
-3.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.796424142187195

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.429290512385807

> <JCHEM_PKA_STRONGEST_BASIC>
-1.626006643085781

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
99.00689999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
epoprostenol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001335
     RDKit          3D
Prostaglandin I2
 57 58  0  0  0  0  0  0  0  0999 V2000
   -7.6138   -0.3843    1.3345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0215    0.2175    0.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8245   -0.5175   -0.4288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6858   -0.5997    0.5176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0997    0.6778    0.9886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5363    1.5420   -0.1040 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4509    1.9349   -1.0593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3257    0.9159   -0.7367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2898    0.6709    0.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0248    0.0537   -0.4581 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0124    0.0269   -1.9760 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7278   -1.0069   -2.5020 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4926   -0.1157   -2.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1185    0.7819   -1.2359 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1346    0.1393   -0.4910 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1392    0.5204    0.8216 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1145    0.6619    1.6902 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5369    0.3992    1.3435 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7317   -0.0243   -0.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1878   -0.2718   -0.3450 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6877   -1.3859    0.4704 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9068   -2.0719    1.1643 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0450   -1.7210    0.5030 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6930    0.7818    1.1555 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0886    1.0691   -0.1747 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.6669    0.4348    2.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6572   -0.7302    1.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0439   -1.1967    1.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8112    0.1549   -0.7056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7880    1.2814    0.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1341   -1.5630   -0.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5169   -0.0659   -1.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8957   -1.3011    1.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8560   -1.1408   -0.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2289    0.4096    1.6515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7891    1.2863    1.6117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1832    2.4842    0.4152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2333    2.8181   -1.4490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2755    0.6636   -1.7871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3446    0.9258    1.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1841   -0.9303   -0.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3313    1.0075   -2.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2411   -1.8684   -2.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7191    0.2092   -3.3051 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8194   -1.1698   -2.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5423    1.7035   -1.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8952    0.9841    2.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9482   -0.3046    2.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0955    1.3580    1.5080 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1562   -0.9689   -0.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3386    0.7860   -0.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2845   -0.4702   -1.4387 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7267    0.6631   -0.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4379   -1.8673    1.4199 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2254   -0.0940    1.6191 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6229    1.6943    1.7905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7123    2.0871   -0.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  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
 15 16  1  0
 16 17  2  3
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 16 24  1  0
 24 25  1  0
 25 10  1  0
 25 14  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  1
  7 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  1
 11 42  1  6
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  6
 17 47  1  0
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 23 54  1  0
 24 55  1  0
 24 56  1  0
 25 57  1  1
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      12.232 -12.597   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.775 -12.131   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.226 -14.139   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.009 -11.224   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      10.762 -10.551   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       9.881 -13.381   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.794 -14.618   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.560 -14.897   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.206  -9.858   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      10.302 -16.121   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      14.881 -14.139   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.573  -9.055   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.202 -14.897   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.523 -14.139   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      16.202 -16.419   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      18.845 -14.897   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      20.185 -14.139   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      21.487 -14.897   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      22.828 -14.139   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.585  -7.490   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.933  -6.725   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.928  -5.165   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.267  -4.386   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      17.616  -5.159   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      16.262  -2.841   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2    9                                                       
CONECT    6    2    7                                                       
CONECT    7    3   10    6                                                  
CONECT    8    3   11                                                       
CONECT    9    4   12    5                                                  
CONECT   10    7                                                            
CONECT   11    8   13                                                       
CONECT   12    9   20                                                       
CONECT   13   11   14   15                                                  
CONECT   14   13   16                                                       
CONECT   15   13                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   12   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

COMPND    HMDB0001335
HETATM    1  C1  UNL     1      -7.614  -0.384   1.334  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.021   0.218   0.100  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.825  -0.518  -0.429  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.686  -0.600   0.518  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.100   0.678   0.989  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.536   1.542  -0.104  1.00  0.00           C  
HETATM    7  O1  UNL     1      -4.451   1.935  -1.059  1.00  0.00           O  
HETATM    8  C7  UNL     1      -2.326   0.916  -0.737  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.290   0.671   0.037  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.025   0.054  -0.458  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.012   0.027  -1.976  1.00  0.00           C  
HETATM   12  O2  UNL     1      -0.728  -1.007  -2.502  1.00  0.00           O  
HETATM   13  C11 UNL     1       1.493  -0.116  -2.256  1.00  0.00           C  
HETATM   14  C12 UNL     1       2.118   0.782  -1.236  1.00  0.00           C  
HETATM   15  O3  UNL     1       3.135   0.139  -0.491  1.00  0.00           O  
HETATM   16  C13 UNL     1       3.139   0.520   0.822  1.00  0.00           C  
HETATM   17  C14 UNL     1       4.115   0.662   1.690  1.00  0.00           C  
HETATM   18  C15 UNL     1       5.537   0.399   1.344  1.00  0.00           C  
HETATM   19  C16 UNL     1       5.732  -0.024  -0.082  1.00  0.00           C  
HETATM   20  C17 UNL     1       7.188  -0.272  -0.345  1.00  0.00           C  
HETATM   21  C18 UNL     1       7.688  -1.386   0.470  1.00  0.00           C  
HETATM   22  O4  UNL     1       6.907  -2.072   1.164  1.00  0.00           O  
HETATM   23  O5  UNL     1       9.045  -1.721   0.503  1.00  0.00           O  
HETATM   24  C19 UNL     1       1.693   0.782   1.155  1.00  0.00           C  
HETATM   25  C20 UNL     1       1.089   1.069  -0.175  1.00  0.00           C  
HETATM   26  H1  UNL     1      -7.667   0.435   2.106  1.00  0.00           H  
HETATM   27  H2  UNL     1      -8.657  -0.730   1.199  1.00  0.00           H  
HETATM   28  H3  UNL     1      -7.044  -1.197   1.780  1.00  0.00           H  
HETATM   29  H4  UNL     1      -7.811   0.155  -0.706  1.00  0.00           H  
HETATM   30  H5  UNL     1      -6.788   1.281   0.212  1.00  0.00           H  
HETATM   31  H6  UNL     1      -6.134  -1.563  -0.671  1.00  0.00           H  
HETATM   32  H7  UNL     1      -5.517  -0.066  -1.376  1.00  0.00           H  
HETATM   33  H8  UNL     1      -4.896  -1.301   1.378  1.00  0.00           H  
HETATM   34  H9  UNL     1      -3.856  -1.141  -0.033  1.00  0.00           H  
HETATM   35  H10 UNL     1      -3.229   0.410   1.652  1.00  0.00           H  
HETATM   36  H11 UNL     1      -4.789   1.286   1.612  1.00  0.00           H  
HETATM   37  H12 UNL     1      -3.183   2.484   0.415  1.00  0.00           H  
HETATM   38  H13 UNL     1      -4.233   2.818  -1.449  1.00  0.00           H  
HETATM   39  H14 UNL     1      -2.275   0.664  -1.787  1.00  0.00           H  
HETATM   40  H15 UNL     1      -1.345   0.926   1.087  1.00  0.00           H  
HETATM   41  H16 UNL     1       0.184  -0.930  -0.043  1.00  0.00           H  
HETATM   42  H17 UNL     1      -0.331   1.007  -2.368  1.00  0.00           H  
HETATM   43  H18 UNL     1      -0.241  -1.868  -2.431  1.00  0.00           H  
HETATM   44  H19 UNL     1       1.719   0.209  -3.305  1.00  0.00           H  
HETATM   45  H20 UNL     1       1.819  -1.170  -2.174  1.00  0.00           H  
HETATM   46  H21 UNL     1       2.542   1.703  -1.676  1.00  0.00           H  
HETATM   47  H22 UNL     1       3.895   0.984   2.714  1.00  0.00           H  
HETATM   48  H23 UNL     1       5.948  -0.305   2.063  1.00  0.00           H  
HETATM   49  H24 UNL     1       6.095   1.358   1.508  1.00  0.00           H  
HETATM   50  H25 UNL     1       5.156  -0.969  -0.271  1.00  0.00           H  
HETATM   51  H26 UNL     1       5.339   0.786  -0.739  1.00  0.00           H  
HETATM   52  H27 UNL     1       7.284  -0.470  -1.439  1.00  0.00           H  
HETATM   53  H28 UNL     1       7.727   0.663  -0.066  1.00  0.00           H  
HETATM   54  H29 UNL     1       9.438  -1.867   1.420  1.00  0.00           H  
HETATM   55  H30 UNL     1       1.225  -0.094   1.619  1.00  0.00           H  
HETATM   56  H31 UNL     1       1.623   1.694   1.790  1.00  0.00           H  
HETATM   57  H32 UNL     1       0.712   2.087  -0.300  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4   31   32
CONECT    4    5   33   34
CONECT    5    6   35   36
CONECT    6    7    8   37
CONECT    7   38
CONECT    8    9    9   39
CONECT    9   10   40
CONECT   10   11   25   41
CONECT   11   12   13   42
CONECT   12   43
CONECT   13   14   44   45
CONECT   14   15   25   46
CONECT   15   16
CONECT   16   17   17   24
CONECT   17   18   47
CONECT   18   19   48   49
CONECT   19   20   50   51
CONECT   20   21   52   53
CONECT   21   22   22   23
CONECT   23   54
CONECT   24   25   55   56
CONECT   25   57
END

HMDB0001335
     RDKit          3D
Prostaglandin I2
 57 58  0  0  0  0  0  0  0  0999 V2000
   -7.6138   -0.3843    1.3345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0215    0.2175    0.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8245   -0.5175   -0.4288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6858   -0.5997    0.5176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0997    0.6778    0.9886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5363    1.5420   -0.1040 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4509    1.9349   -1.0593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3257    0.9159   -0.7367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2898    0.6709    0.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0248    0.0537   -0.4581 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0124    0.0269   -1.9760 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7278   -1.0069   -2.5020 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4926   -0.1157   -2.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1185    0.7819   -1.2359 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1346    0.1393   -0.4910 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1392    0.5204    0.8216 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1145    0.6619    1.6902 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5369    0.3992    1.3435 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7317   -0.0243   -0.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1878   -0.2718   -0.3450 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6877   -1.3859    0.4704 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9068   -2.0719    1.1643 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0450   -1.7210    0.5030 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6930    0.7818    1.1555 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0886    1.0691   -0.1747 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.6669    0.4348    2.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6572   -0.7302    1.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0439   -1.1967    1.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8112    0.1549   -0.7056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7880    1.2814    0.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1341   -1.5630   -0.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5169   -0.0659   -1.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8957   -1.3011    1.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8560   -1.1408   -0.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2289    0.4096    1.6515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7891    1.2863    1.6117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1832    2.4842    0.4152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2333    2.8181   -1.4490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2755    0.6636   -1.7871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3446    0.9258    1.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1841   -0.9303   -0.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3313    1.0075   -2.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2411   -1.8684   -2.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7191    0.2092   -3.3051 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8194   -1.1698   -2.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5423    1.7035   -1.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8952    0.9841    2.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9482   -0.3046    2.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0955    1.3580    1.5080 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1562   -0.9689   -0.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3386    0.7860   -0.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2845   -0.4702   -1.4387 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7267    0.6631   -0.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4379   -1.8673    1.4199 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2254   -0.0940    1.6191 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6229    1.6943    1.7905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7123    2.0871   -0.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  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
 15 16  1  0
 16 17  2  3
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 16 24  1  0
 24 25  1  0
 25 10  1  0
 25 14  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  1
  7 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  1
 11 42  1  6
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  6
 17 47  1  0
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 23 54  1  0
 24 55  1  0
 24 56  1  0
 25 57  1  1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5Z,13E)-(15S)-6,9alpha-Epoxy-11alpha,15-dihydroxyprosta-5,13-dienoate	ChEBI
(5Z,9alpha,11alpha,13E,15S)-6,9-Epoxy-11,15-dihydroxyprosta-5,13-dien-1-Oic acid	ChEBI
Epoprostenol	ChEBI
Flolan	ChEBI
PGI2	ChEBI
PGX	ChEBI
Prostacyclin	ChEBI
Prostaglandin X	ChEBI
Vasocyclin	ChEBI
(5Z,13E)-(15S)-6,9a-Epoxy-11a,15-dihydroxyprosta-5,13-dienoate	Generator
(5Z,13E)-(15S)-6,9a-Epoxy-11a,15-dihydroxyprosta-5,13-dienoic acid	Generator
(5Z,13E)-(15S)-6,9alpha-Epoxy-11alpha,15-dihydroxyprosta-5,13-dienoic acid	Generator
(5Z,13E)-(15S)-6,9Α-epoxy-11α,15-dihydroxyprosta-5,13-dienoate	Generator
(5Z,13E)-(15S)-6,9Α-epoxy-11α,15-dihydroxyprosta-5,13-dienoic acid	Generator
(5Z,9a,11a,13E,15S)-6,9-Epoxy-11,15-dihydroxyprosta-5,13-dien-1-Oate	Generator
(5Z,9a,11a,13E,15S)-6,9-Epoxy-11,15-dihydroxyprosta-5,13-dien-1-Oic acid	Generator
(5Z,9alpha,11alpha,13E,15S)-6,9-Epoxy-11,15-dihydroxyprosta-5,13-dien-1-Oate	Generator
(5Z,9Α,11α,13E,15S)-6,9-epoxy-11,15-dihydroxyprosta-5,13-dien-1-Oate	Generator
(5Z,9Α,11α,13E,15S)-6,9-epoxy-11,15-dihydroxyprosta-5,13-dien-1-Oic acid	Generator
(5Z,13E)-(15S)-6,9-alpha-Epoxy-11-alpha,15-dihydroxyprosta-5,13-dienoate	HMDB
(5Z,13E)-(15S)-6,9-alpha-Epoxy-11-alpha,15-dihydroxyprosta-5,13-dienoic acid	HMDB
(5Z,13E)-(15S)-6,9-Epoxy-11,15-dihydroxyprosta-5,13-dienoate	HMDB
(5Z,13E)-(15S)-6,9-Epoxy-11,15-dihydroxyprosta-5,13-dienoic acid	HMDB
(5Z,13E,15S)-6,9a-Epoxy-11a,15-dihydroxyprosta-5,13-dienoate	HMDB
(5Z,13E,15S)-6,9a-Epoxy-11a,15-dihydroxyprosta-5,13-dienoic acid	HMDB
Prostacycline	HMDB
Epoprostanol	HMDB
Epoprostenol sodium	HMDB
Epoprostenol sodium salt, (5Z,9alpha,11alpha,13E,15S)-isomer	HMDB
Prostaglandin I(2)	HMDB
Veletri	MeSH

Chemical Formula

C₂₀H₃₂O₅

Average Molecular Weight

352.4651

Monoisotopic Molecular Weight

352.224974134

IUPAC Name

5-[(3aR,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-hexahydro-2H-cyclopenta[b]furan-2-ylidene]pentanoic acid

Traditional Name

epoprostenol

CAS Registry Number

35121-78-9

SMILES

CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@@H]2OC(C[C@H]12)=CCCCC(O)=O

InChI Identifier

InChI=1S/C20H32O5/c1-2-3-4-7-14(21)10-11-16-17-12-15(8-5-6-9-20(23)24)25-19(17)13-18(16)22/h8,10-11,14,16-19,21-22H,2-7,9,12-13H2,1H3,(H,23,24)/b11-10+,15-8-/t14-,16+,17+,18+,19-/m0/s1

InChI Key

KAQKFAOMNZTLHT-OZUDYXHBSA-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
Fatty alcohol
Medium-chain hydroxy acid
Medium-chain fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Cyclic alcohol
Tetrahydrofuran
Secondary alcohol
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

prostaglandins I (CHEBI:15552 )
Prostaglandins (C01312 )
Prostaglandins (LMFA03010087 )

Ontology

Not Available

Adipose Tissue (HMDB: HMDB0001335)

Organ

Biofluid or Excreta

Non-excretory biofluid

Blood (HMDB: HMDB0001335)

Cell

Fibroblasts (HMDB: HMDB0001335)
Neuron (HMDB: HMDB0001335)

Hematocyte

Platelet (HMDB: HMDB0001335)

Cellular substructure

Membrane (HMDB: HMDB0001335)
Extracellular (HMDB: HMDB0001335)

Organelle

Endoplasmic reticulum (HMDB: HMDB0001335)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Arachidonic Acid Metabolism (HMDB: HMDB0001335)

Disease pathway

Leukotriene C4 Synthesis Deficiency (PathBank: SMP0000353)

Drug action pathway

Piroxicam Action Pathway (PathBank: SMP0000077)
Acetylsalicylic Acid Action Pathway (PathBank: SMP0000083)
Etodolac Action Pathway (PathBank: SMP0000084)
Ketoprofen Action Pathway (PathBank: SMP0000085)
Ibuprofen Action Pathway (PathBank: SMP0000086)
Rofecoxib Action Pathway (PathBank: SMP0000087)
Diclofenac Action Pathway (PathBank: SMP0000093)
Sulindac Action Pathway (PathBank: SMP0000094)
Celecoxib Action Pathway (PathBank: SMP0000096)
Ketorolac Action Pathway (PathBank: SMP0000098)
Suprofen Action Pathway (PathBank: SMP0000101)
Bromfenac Action Pathway (PathBank: SMP0000102)
Indomethacin Action Pathway (PathBank: SMP0000104)
Mefenamic Acid Action Pathway (PathBank: SMP0000109)
Oxaprozin Action Pathway (PathBank: SMP0000113)
Nabumetone Action Pathway (PathBank: SMP0000114)
Naproxen Action Pathway (PathBank: SMP0000120)
Diflunisal Action Pathway (PathBank: SMP0000289)
Meloxicam Action Pathway (PathBank: SMP0000106)
Valdecoxib Action Pathway (PathBank: SMP0000116)
Antipyrine Action Pathway (PathBank: SMP0000692)
Antrafenine Action Pathway (PathBank: SMP0000693)
Carprofen Action Pathway (PathBank: SMP0000694)
Etoricoxib Action Pathway (PathBank: SMP0000695)
Fenoprofen Action Pathway (PathBank: SMP0000696)
Flurbiprofen Action Pathway (PathBank: SMP0000697)
Magnesium Salicylate Action Pathway (PathBank: SMP0000698)
Lumiracoxib Action Pathway (PathBank: SMP0000699)
Lornoxicam Action Pathway (PathBank: SMP0000700)
Phenylbutazone Action Pathway (PathBank: SMP0000701)
Nepafenac Action Pathway (PathBank: SMP0000702)
Trisalicylate-Choline Action Pathway (PathBank: SMP0000703)
Tolmetin Action Pathway (PathBank: SMP0000704)
Tiaprofenic Acid Action Pathway (PathBank: SMP0000705)
Tenoxicam Action Pathway (PathBank: SMP0000706)
Salsalate Action Pathway (PathBank: SMP0000707)
Salicylate-Sodium Action Pathway (PathBank: SMP0000708)
Salicylic Acid Action Pathway (PathBank: SMP0000709)
Acetaminophen Action Pathway (PathBank: SMP0000710)

Signaling pathway

Intracellular Signalling Through Prostacyclin Receptor and Prostacyclin (PathBank: SMP0000354)

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	186.843	30932474
[M+H]+	MetCCS_train_pos	198.567	30932474
[M-H]-	Not Available	186.843	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000243
[M+H]+	Not Available	199.137	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000243

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	3.83	ALOGPS
logP	2.42	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	4.43	ChemAxon
pKa (Strongest Basic)	-1.6	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	10	ChemAxon
Refractivity	99.01 m³·mol⁻¹	ChemAxon
Polarizability	41.47 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	186.746	31661259
DarkChem	[M-H]-	190.476	31661259
AllCCS	[M+H]+	193.225	32859911
AllCCS	[M-H]-	192.259	32859911
DeepCCS	[M-2H]-	230.84	30932474
DeepCCS	[M+Na]+	205.968	30932474
AllCCS	[M+H]+	193.2	32859911
AllCCS	[M+H-H2O]+	190.6	32859911
AllCCS	[M+NH4]+	195.7	32859911
AllCCS	[M+Na]+	196.4	32859911
AllCCS	[M-H]-	192.3	32859911
AllCCS	[M+Na-2H]-	193.3	32859911
AllCCS	[M+HCOO]-	194.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Prostaglandin I2	CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@@H]2OC(C[C@H]12)=CCCCC(O)=O	4472.2	Standard polar	33892256
Prostaglandin I2	CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@@H]2OC(C[C@H]12)=CCCCC(O)=O	2766.3	Standard non polar	33892256
Prostaglandin I2	CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@@H]2OC(C[C@H]12)=CCCCC(O)=O	2962.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Prostaglandin I2,1TMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@@H]2OC(=CCCCC(=O)O)C[C@@H]21)O[Si](C)(C)C	2836.0	Semi standard non polar	33892256
Prostaglandin I2,1TMS,isomer #2	CCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C)C[C@@H]2OC(=CCCCC(=O)O)C[C@@H]21	2827.3	Semi standard non polar	33892256
Prostaglandin I2,1TMS,isomer #3	CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)C[C@@H]2OC(=CCCCC(=O)O[Si](C)(C)C)C[C@@H]21	2790.5	Semi standard non polar	33892256
Prostaglandin I2,2TMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C)C[C@@H]2OC(=CCCCC(=O)O)C[C@@H]21)O[Si](C)(C)C	2842.8	Semi standard non polar	33892256
Prostaglandin I2,2TMS,isomer #2	CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@@H]2OC(=CCCCC(=O)O[Si](C)(C)C)C[C@@H]21)O[Si](C)(C)C	2854.0	Semi standard non polar	33892256
Prostaglandin I2,2TMS,isomer #3	CCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C)C[C@@H]2OC(=CCCCC(=O)O[Si](C)(C)C)C[C@@H]21	2810.0	Semi standard non polar	33892256
Prostaglandin I2,3TMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C)C[C@@H]2OC(=CCCCC(=O)O[Si](C)(C)C)C[C@@H]21)O[Si](C)(C)C	2816.6	Semi standard non polar	33892256
Prostaglandin I2,1TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@@H]2OC(=CCCCC(=O)O)C[C@@H]21)O[Si](C)(C)C(C)(C)C	3051.8	Semi standard non polar	33892256
Prostaglandin I2,1TBDMS,isomer #2	CCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C[C@@H]2OC(=CCCCC(=O)O)C[C@@H]21	3046.0	Semi standard non polar	33892256
Prostaglandin I2,1TBDMS,isomer #3	CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)C[C@@H]2OC(=CCCCC(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]21	3018.7	Semi standard non polar	33892256
Prostaglandin I2,2TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C[C@@H]2OC(=CCCCC(=O)O)C[C@@H]21)O[Si](C)(C)C(C)(C)C	3294.2	Semi standard non polar	33892256
Prostaglandin I2,2TBDMS,isomer #2	CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@@H]2OC(=CCCCC(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]21)O[Si](C)(C)C(C)(C)C	3299.5	Semi standard non polar	33892256
Prostaglandin I2,2TBDMS,isomer #3	CCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C[C@@H]2OC(=CCCCC(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]21	3262.6	Semi standard non polar	33892256
Prostaglandin I2,3TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C[C@@H]2OC(=CCCCC(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]21)O[Si](C)(C)C(C)(C)C	3541.5	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 - Prostaglandin I2 GC-MS (Non-derivatized) - 70eV, Positive	splash10-0159-5693000000-d4cdd32893c86bb9479a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin I2 GC-MS (3 TMS) - 70eV, Positive	splash10-0ug0-9253570000-9f0d8bdb642b0c32f40b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin I2 GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin I2 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 - Prostaglandin I2 10V, Positive-QTOF	splash10-00kr-0029000000-6c6186798558c5d1611f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin I2 20V, Positive-QTOF	splash10-00y0-1093000000-eacafc8768142dba71da	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin I2 40V, Positive-QTOF	splash10-00du-9450000000-e3b550dcd32e28648707	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin I2 10V, Negative-QTOF	splash10-0udi-0009000000-34a4a3eaa1abb59e8245	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin I2 20V, Negative-QTOF	splash10-0f89-2139000000-efe90037816a750cfeee	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin I2 40V, Negative-QTOF	splash10-0a59-9871000000-f961005fef0ef2363ce4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin I2 10V, Negative-QTOF	splash10-0udi-0009000000-39b83b5b9b932bb2f6a1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin I2 20V, Negative-QTOF	splash10-0ue9-0089000000-7141693b6303cf4e2e29	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin I2 40V, Negative-QTOF	splash10-003s-2391000000-22e55e30c5e2afce8cc2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin I2 10V, Positive-QTOF	splash10-014r-0009000000-fcc9a31a4c60d564196f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin I2 20V, Positive-QTOF	splash10-014i-6359000000-d638f048af6abdb45cbf	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin I2 40V, Positive-QTOF	splash10-05tf-9610000000-8baf1f1acd84f0ed7ba8	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)
Endoplasmic reticulum

Biospecimen Locations

Not Available

Tissue Locations

Adipose Tissue
Bladder
Blood
Brain
Fibroblasts
Kidney
Liver
Neuron
Placenta
Platelet

Pathways

Name	SMPDB/PathBank	KEGG
Arachidonic Acid Metabolism
Leukotriene C4 Synthesis Deficiency		Not Available
Piroxicam Action Pathway		Not Available
Acetylsalicylic Acid Action Pathway		Not Available
Etodolac Action Pathway		Not Available

Normal Concentrations

Not Available

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

FDB022560

KNApSAcK ID

Not Available

Chemspider ID

4445566

KEGG Compound ID

C01312

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15552

Food Biomarker Ontology

Not Available

VMH ID

PROSTGI2

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Walsh SW, Wang Y, Killian A: AA-2414, an antioxidant and thromboxane receptor blocker, completely inhibits peroxide-induced vasoconstriction in the human placenta. J Pharmacol Exp Ther. 1999 Jul;290(1):220-6. [PubMed:10381779 ]
Brinkmann A, Seeling W, Wolf CF, Kneitinger E, Junger S, Rockemann M, Oettinger W, Georgieff M: [The effect of thoracic epidural anesthesia on the pathophysiology of the eventration syndrome]. Anaesthesist. 1994 Apr;43(4):235-44. [PubMed:8179173 ]
Kearney D, Byrne A, Crean P, Cox D, Fitzgerald DJ: Optimal suppression of thromboxane A(2) formation by aspirin during percutaneous transluminal coronary angioplasty: no additional effect of a selective cyclooxygenase-2 inhibitor. J Am Coll Cardiol. 2004 Feb 18;43(4):526-31. [PubMed:14975458 ]
De La Cruz JP, Arrebola MM, Villalobos MA, Pinacho A, Guerrero A, Gonzalez-Correa JA, Sanchez de la Cuesta F: Influence of glucose concentration on the effects of aspirin, ticlopidine and clopidogrel on platelet function and platelet-subendothelium interaction. Eur J Pharmacol. 2004 Jan 19;484(1):19-27. [PubMed:14729378 ]
Cruz-Gervis R, Stecenko AA, Dworski R, Lane KB, Loyd JE, Pierson R, King G, Brigham KL: Altered prostanoid production by fibroblasts cultured from the lungs of human subjects with idiopathic pulmonary fibrosis. Respir Res. 2002;3:17. Epub 2002 Feb 23. [PubMed:11980586 ]
den Dekker E, Gorter G, Heemskerk JW, Akkerman JW: Development of platelet inhibition by cAMP during megakaryocytopoiesis. J Biol Chem. 2002 Aug 9;277(32):29321-9. Epub 2002 May 7. [PubMed:11997386 ]
McAdam BF, Byrne D, Morrow JD, Oates JA: Contribution of cyclooxygenase-2 to elevated biosynthesis of thromboxane A2 and prostacyclin in cigarette smokers. Circulation. 2005 Aug 16;112(7):1024-9. Epub 2005 Aug 8. [PubMed:16087791 ]
Hei ZQ, Huang HQ, Luo CF, Li SR, Luo GJ: Changes of nitric oxide and endothelin, thromboxane A2 and prostaglandin in cirrhotic patients undergoing liver transplantation. World J Gastroenterol. 2006 Jul 7;12(25):4049-51. [PubMed:16810757 ]
Nadar S, Lip GY: Platelet activation in the hypertensive disorders of pregnancy. Expert Opin Investig Drugs. 2004 May;13(5):523-9. [PubMed:15155127 ]
Fruzzetti F, Giannessi D, Ricci C, Bernini W, Puntoni R, Genazzani AR, De Caterina R: Platelet-vessel wall interactions with third-generation oral contraceptives: no evidence of detrimental effects. Thromb Haemost. 1999 Sep;82(3):1164-70. [PubMed:10494782 ]
Cheng Y, Austin SC, Rocca B, Koller BH, Coffman TM, Grosser T, Lawson JA, FitzGerald GA: Role of prostacyclin in the cardiovascular response to thromboxane A2. Science. 2002 Apr 19;296(5567):539-41. [PubMed:11964481 ]
Okamoto M, Abe T, Shouno M, Kitabata Y, Narukawa N, Kobata H, Akizawa T: A case of thrombotic thrombocytopenic purpura refractory to plasma exchange. Ther Apher. 2001 Feb;5(1):49-53. [PubMed:11258611 ]
Li J, Dai G, Feng Z, Wang C, Yang Y, Wei W, Zhou B: Effect of low HDL combined with hypertriglyceridemia in coronary artery disease patients on PGI2 biological activity in relation to lipid regulating treatment. J Tongji Med Univ. 1998;18(2):87-9, 93. [PubMed:10806831 ]
Vassaux G, Gaillard D, Darimont C, Ailhaud G, Negrel R: Differential response of preadipocytes and adipocytes to prostacyclin and prostaglandin E2: physiological implications. Endocrinology. 1992 Nov;131(5):2393-8. [PubMed:1330499 ]
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Enzymes

Enzyme Details

1. Prostaglandin G/H synthase 2

General function:: Involved in peroxidase activity
Specific function:: Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:: PTGS2
Uniprot ID:: P35354
Molecular weight:: 68995.625

Enzyme Details

2. Prostacyclin synthase

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the isomerization of prostaglandin H2 to prostacyclin (= prostaglandin I2).
Gene Name:: PTGIS
Uniprot ID:: Q16647
Molecular weight:: 57103.385

Reactions

Prostaglandin H2 → Prostaglandin I2	details

Enzyme Details

3. 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

Showing metabocard for Prostaglandin I2 (HMDB0001335)

MOL for HMDB0001335 (Prostaglandin I2)

3D MOL for HMDB0001335 (Prostaglandin I2)

3D SDF for HMDB0001335 (Prostaglandin I2)

3D-SDF for HMDB0001335 (Prostaglandin I2)

PDB for HMDB0001335 (Prostaglandin I2)

3D PDB for HMDB0001335 (Prostaglandin I2)

SMILES for HMDB0001335 (Prostaglandin I2)

INCHI for HMDB0001335 (Prostaglandin I2)

Structure for HMDB0001335 (Prostaglandin I2)

3D Structure for HMDB0001335 (Prostaglandin I2)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions