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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:51 UTC

HMDB ID

HMDB0015064

Secondary Accession Numbers

HMDB15064

Metabolite Identification

Common Name

Misoprostol

Description

Misoprostol is only found in individuals that have used or taken this drug. It is a synthetic analog of natural prostaglandin E1. It produces a dose-related inhibition of gastric acid and pepsin secretion, and enhances mucosal resistance to injury. It is an effective anti-ulcer agent and also has oxytocic properties. [PubChem]Misoprostol seems to inhibit gastric acid secretion by a direct action on the parietal cells through binding to the prostaglandin receptor. The activity of this receptor is mediated by G proteins which normally activate adenylate cyclase. The indirect inhibition of adenylate cyclase by Misoprostol may be dependent on guanosine-5’-triphosphate (GTP). The significant cytoprotective actions of misoprostol are related to several mechanisms. These include: 1. Increased secretion of bicarbonate, 2. Considerable decrease in the volume and pepsin content of the gastric secretions, 3. It prevents harmful agents from disrupting the tight junctions between the epithelial cells which stops the subsequent back diffusion of H⁺ ions into the gastric mucosa, 4. Increased thickness of mucus layer, 5. Enhanced mucosal blood flow as a result of direct vasodilatation, 6. Stabilization of tissue lysozymes/vascular endothelium, 7. Improvement of mucosal regeneration capacity, and 8. Replacement of prostaglandins that have been depleted as a result of various insults to the area. Misoprostol has also been shown to increase the amplitude and frequency of uterine contractions during pregnancy via selective binding to the EP-2/EP-3 prostanoid receptors.

Structure

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

929
  Mrv0541 02231215062D          

 27 27  0  0  1  0            999 V2000
   10.1452   -1.7365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7957   -3.4435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7096    1.6830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4347   -3.1799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8763   -1.8208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0257   -1.9915    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6931   -1.5066    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.3606   -1.9915    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.1056   -2.7761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2410   -1.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2806   -2.7761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6931   -0.6815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6279   -2.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8433   -2.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4076   -0.2690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1221    0.9685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4076    0.5560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2302   -2.5857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8366    1.3810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5346    0.2540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4455   -2.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8366    2.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5511    2.6185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8325   -2.8828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5511    3.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0478   -2.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.9249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  6  0  0  0
  2 11  2  0  0  0  0
  3 16  1  0  0  0  0
  4 26  1  0  0  0  0
  4 27  1  0  0  0  0
  5 26  2  0  0  0  0
  6  7  1  0  0  0  0
  6 10  1  6  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  7 12  1  1  0  0  0
  8  9  1  0  0  0  0
  9 11  1  0  0  0  0
 10 13  1  0  0  0  0
 12 15  2  0  0  0  0
 13 14  1  0  0  0  0
 14 18  1  0  0  0  0
 15 17  1  0  0  0  0
 16 17  1  0  0  0  0
 16 19  1  0  0  0  0
 16 20  1  0  0  0  0
 18 21  1  0  0  0  0
 19 22  1  0  0  0  0
 21 24  1  0  0  0  0
 22 23  1  0  0  0  0
 23 25  1  0  0  0  0
 24 26  1  0  0  0  0
M  END

HMDB0015064
     RDKit          3D
Misoprostol
 65 65  0  0  0  0  0  0  0  0999 V2000
   -8.1306   -0.1375   -0.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3393    0.5601   -1.4959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9355    0.8842   -1.0768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1301   -0.3196   -0.7153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7186    0.1012   -0.3011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9128    1.0143    0.9042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1880    0.7976   -1.3578 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9232   -1.0919    0.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5351   -0.8077    0.5159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9498    0.3684    0.5457 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4410    0.6488    0.9590 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3424    1.4853    2.2435 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3213    2.4671    2.2842 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4366    0.5034    3.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6640   -0.8313    2.7445 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4498   -1.9153    3.2115 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2318   -0.5341    1.3800 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6878   -0.2567    1.5092 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3595    0.2041    0.2589 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2738   -0.7719   -0.8771 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8779   -2.0883   -0.6310 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3216   -2.1855   -0.3121 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2958   -1.7633   -1.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2833   -0.3778   -1.8163 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8940   -0.0096   -2.9714 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7251    0.6455   -0.9626 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7047    1.9681   -1.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7523    0.0964    0.5805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1919    0.1989   -0.4864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1445   -1.2265   -0.6479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8436    1.5227   -1.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3829   -0.0369   -2.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4468    1.3520   -1.9815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9331    1.6488   -0.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0799   -1.0185   -1.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6265   -0.8837    0.1165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9517    0.9473    1.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7474    2.0611    0.6488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2686    0.6534    1.7484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4702    1.7601   -1.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8726   -1.7731   -0.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4798   -1.6724    0.8833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8857   -1.6429    0.8388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5425    1.2352    0.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9018    1.2646    0.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6371    2.0086    2.2844 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1220    3.1770    1.6504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5183    0.4382    3.9460 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2796    0.7513    4.0562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1252   -1.4122    0.7109 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8215    0.5684    2.2655 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1775   -1.1408    1.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4276    0.4585    0.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8961    1.1548   -0.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6123   -0.3342   -1.8147 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1580   -0.9766   -1.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2506   -2.7336    0.0590 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7549   -2.6645   -1.6151 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5899   -1.5961    0.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5868   -3.2685   -0.0461 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1270   -2.3981   -2.2840 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3517   -2.0446   -1.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1024    2.6152   -0.6300 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6387    2.2411   -1.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3044    2.1116   -2.3629 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
  5  7  1  0
  5  8  1  0
  8  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  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 17 11  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  6 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  0
 10 44  1  0
 11 45  1  6
 12 46  1  6
 13 47  1  0
 14 48  1  0
 14 49  1  0
 17 50  1  6
 18 51  1  0
 18 52  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 21 57  1  0
 21 58  1  0
 22 59  1  0
 22 60  1  0
 23 61  1  0
 23 62  1  0
 27 63  1  0
 27 64  1  0
 27 65  1  0
M  END

929
  Mrv0541 02231215062D          

 27 27  0  0  1  0            999 V2000
   10.1452   -1.7365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7957   -3.4435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7096    1.6830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4347   -3.1799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8763   -1.8208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0257   -1.9915    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6931   -1.5066    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.3606   -1.9915    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.1056   -2.7761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2410   -1.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2806   -2.7761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6931   -0.6815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6279   -2.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8433   -2.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4076   -0.2690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1221    0.9685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4076    0.5560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2302   -2.5857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8366    1.3810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5346    0.2540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4455   -2.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8366    2.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5511    2.6185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8325   -2.8828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5511    3.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0478   -2.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.9249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  6  0  0  0
  2 11  2  0  0  0  0
  3 16  1  0  0  0  0
  4 26  1  0  0  0  0
  4 27  1  0  0  0  0
  5 26  2  0  0  0  0
  6  7  1  0  0  0  0
  6 10  1  6  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  7 12  1  1  0  0  0
  8  9  1  0  0  0  0
  9 11  1  0  0  0  0
 10 13  1  0  0  0  0
 12 15  2  0  0  0  0
 13 14  1  0  0  0  0
 14 18  1  0  0  0  0
 15 17  1  0  0  0  0
 16 17  1  0  0  0  0
 16 19  1  0  0  0  0
 16 20  1  0  0  0  0
 18 21  1  0  0  0  0
 19 22  1  0  0  0  0
 21 24  1  0  0  0  0
 22 23  1  0  0  0  0
 23 25  1  0  0  0  0
 24 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015064

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H38O5/c1-4-5-14-22(2,26)15-10-12-18-17(19(23)16-20(18)24)11-8-6-7-9-13-21(25)27-3/h10,12,17-18,20,24,26H,4-9,11,13-16H2,1-3H3/b12-10+/t17-,18-,20-,22?/m1/s1

> <INCHI_KEY>
OJLOPKGSLYJEMD-URPKTTJQSA-N

> <FORMULA>
C22H38O5

> <MOLECULAR_WEIGHT>
382.5341

> <EXACT_MASS>
382.271924326

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
45.377895510563874

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 7-[(1R,2R,3R)-3-hydroxy-2-[(1E)-4-hydroxy-4-methyloct-1-en-1-yl]-5-oxocyclopentyl]heptanoate

> <ALOGPS_LOGP>
3.88

> <JCHEM_LOGP>
3.8577550579999986

> <ALOGPS_LOGS>
-4.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.426349684612113

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.680622594807385

> <JCHEM_PKA_STRONGEST_BASIC>
-0.950334136392576

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
107.87979999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.64e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
misoprostol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015064
     RDKit          3D
Misoprostol
 65 65  0  0  0  0  0  0  0  0999 V2000
   -8.1306   -0.1375   -0.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3393    0.5601   -1.4959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9355    0.8842   -1.0768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1301   -0.3196   -0.7153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7186    0.1012   -0.3011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9128    1.0143    0.9042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1880    0.7976   -1.3578 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9232   -1.0919    0.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5351   -0.8077    0.5159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9498    0.3684    0.5457 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4410    0.6488    0.9590 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3424    1.4853    2.2435 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3213    2.4671    2.2842 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4366    0.5034    3.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6640   -0.8313    2.7445 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4498   -1.9153    3.2115 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2318   -0.5341    1.3800 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6878   -0.2567    1.5092 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3595    0.2041    0.2589 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2738   -0.7719   -0.8771 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8779   -2.0883   -0.6310 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3216   -2.1855   -0.3121 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2958   -1.7633   -1.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2833   -0.3778   -1.8163 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8940   -0.0096   -2.9714 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7251    0.6455   -0.9626 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7047    1.9681   -1.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7523    0.0964    0.5805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1919    0.1989   -0.4864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1445   -1.2265   -0.6479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8436    1.5227   -1.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3829   -0.0369   -2.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4468    1.3520   -1.9815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9331    1.6488   -0.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0799   -1.0185   -1.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6265   -0.8837    0.1165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9517    0.9473    1.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7474    2.0611    0.6488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2686    0.6534    1.7484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4702    1.7601   -1.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8726   -1.7731   -0.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4798   -1.6724    0.8833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8857   -1.6429    0.8388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5425    1.2352    0.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9018    1.2646    0.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6371    2.0086    2.2844 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1220    3.1770    1.6504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5183    0.4382    3.9460 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2796    0.7513    4.0562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1252   -1.4122    0.7109 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8215    0.5684    2.2655 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1775   -1.1408    1.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4276    0.4585    0.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8961    1.1548   -0.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6123   -0.3342   -1.8147 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1580   -0.9766   -1.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2506   -2.7336    0.0590 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7549   -2.6645   -1.6151 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5899   -1.5961    0.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5868   -3.2685   -0.0461 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1270   -2.3981   -2.2840 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3517   -2.0446   -1.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1024    2.6152   -0.6300 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6387    2.2411   -1.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3044    2.1116   -2.3629 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
  5  7  1  0
  5  8  1  0
  8  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  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 17 11  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  6 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  0
 10 44  1  0
 11 45  1  6
 12 46  1  6
 13 47  1  0
 14 48  1  0
 14 49  1  0
 17 50  1  6
 18 51  1  0
 18 52  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 21 57  1  0
 21 58  1  0
 22 59  1  0
 22 60  1  0
 23 61  1  0
 23 62  1  0
 27 63  1  0
 27 64  1  0
 27 65  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 929                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      18.938  -3.241   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      14.552  -6.428   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      18.125   3.142   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.545  -5.936   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       5.369  -3.399   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      14.981  -3.717   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.227  -2.812   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.473  -3.717   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.997  -5.182   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.517  -3.241   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.457  -5.182   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.227  -1.272   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.372  -4.272   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.907  -3.796   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.561  -0.502   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      18.895   1.808   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.561   1.038   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.763  -4.827   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      20.228   2.578   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      19.665   0.474   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.298  -4.351   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      20.228   4.118   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      21.562   4.888   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.154  -5.381   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      21.562   6.428   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.689  -4.905   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.080  -5.460   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2   11                                                            
CONECT    3   16                                                            
CONECT    4   26   27                                                       
CONECT    5   26                                                            
CONECT    6    7   10   11                                                  
CONECT    7    6    8   12                                                  
CONECT    8    1    7    9                                                  
CONECT    9    8   11                                                       
CONECT   10    6   13                                                       
CONECT   11    2    6    9                                                  
CONECT   12    7   15                                                       
CONECT   13   10   14                                                       
CONECT   14   13   18                                                       
CONECT   15   12   17                                                       
CONECT   16    3   17   19   20                                             
CONECT   17   15   16                                                       
CONECT   18   14   21                                                       
CONECT   19   16   22                                                       
CONECT   20   16                                                            
CONECT   21   18   24                                                       
CONECT   22   19   23                                                       
CONECT   23   22   25                                                       
CONECT   24   21   26                                                       
CONECT   25   23                                                            
CONECT   26    4    5   24                                                  
CONECT   27    4                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   54    0
END

COMPND    HMDB0015064
HETATM    1  C1  UNL     1      -8.131  -0.138  -0.434  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.339   0.560  -1.496  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.936   0.884  -1.077  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.130  -0.320  -0.715  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.719   0.101  -0.301  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.913   1.014   0.904  1.00  0.00           C  
HETATM    7  O1  UNL     1      -3.188   0.798  -1.358  1.00  0.00           O  
HETATM    8  C7  UNL     1      -2.923  -1.092   0.105  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.535  -0.808   0.516  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.950   0.368   0.546  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.441   0.649   0.959  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.342   1.485   2.243  1.00  0.00           C  
HETATM   13  O2  UNL     1       1.321   2.467   2.284  1.00  0.00           O  
HETATM   14  C12 UNL     1       0.437   0.503   3.363  1.00  0.00           C  
HETATM   15  C13 UNL     1       0.664  -0.831   2.745  1.00  0.00           C  
HETATM   16  O3  UNL     1       0.450  -1.915   3.212  1.00  0.00           O  
HETATM   17  C14 UNL     1       1.232  -0.534   1.380  1.00  0.00           C  
HETATM   18  C15 UNL     1       2.688  -0.257   1.509  1.00  0.00           C  
HETATM   19  C16 UNL     1       3.360   0.204   0.259  1.00  0.00           C  
HETATM   20  C17 UNL     1       3.274  -0.772  -0.877  1.00  0.00           C  
HETATM   21  C18 UNL     1       3.878  -2.088  -0.631  1.00  0.00           C  
HETATM   22  C19 UNL     1       5.322  -2.185  -0.312  1.00  0.00           C  
HETATM   23  C20 UNL     1       6.296  -1.763  -1.349  1.00  0.00           C  
HETATM   24  C21 UNL     1       6.283  -0.378  -1.816  1.00  0.00           C  
HETATM   25  O4  UNL     1       5.894  -0.010  -2.971  1.00  0.00           O  
HETATM   26  O5  UNL     1       6.725   0.645  -0.963  1.00  0.00           O  
HETATM   27  C22 UNL     1       6.705   1.968  -1.437  1.00  0.00           C  
HETATM   28  H1  UNL     1      -7.752   0.096   0.581  1.00  0.00           H  
HETATM   29  H2  UNL     1      -9.192   0.199  -0.486  1.00  0.00           H  
HETATM   30  H3  UNL     1      -8.144  -1.226  -0.648  1.00  0.00           H  
HETATM   31  H4  UNL     1      -7.844   1.523  -1.727  1.00  0.00           H  
HETATM   32  H5  UNL     1      -7.383  -0.037  -2.429  1.00  0.00           H  
HETATM   33  H6  UNL     1      -5.447   1.352  -1.982  1.00  0.00           H  
HETATM   34  H7  UNL     1      -5.933   1.649  -0.301  1.00  0.00           H  
HETATM   35  H8  UNL     1      -5.080  -1.019  -1.573  1.00  0.00           H  
HETATM   36  H9  UNL     1      -5.626  -0.884   0.116  1.00  0.00           H  
HETATM   37  H10 UNL     1      -4.952   0.947   1.321  1.00  0.00           H  
HETATM   38  H11 UNL     1      -3.747   2.061   0.649  1.00  0.00           H  
HETATM   39  H12 UNL     1      -3.269   0.653   1.748  1.00  0.00           H  
HETATM   40  H13 UNL     1      -3.470   1.760  -1.282  1.00  0.00           H  
HETATM   41  H14 UNL     1      -2.873  -1.773  -0.772  1.00  0.00           H  
HETATM   42  H15 UNL     1      -3.480  -1.672   0.883  1.00  0.00           H  
HETATM   43  H16 UNL     1      -0.886  -1.643   0.839  1.00  0.00           H  
HETATM   44  H17 UNL     1      -1.542   1.235   0.230  1.00  0.00           H  
HETATM   45  H18 UNL     1       0.902   1.265   0.148  1.00  0.00           H  
HETATM   46  H19 UNL     1      -0.637   2.009   2.284  1.00  0.00           H  
HETATM   47  H20 UNL     1       1.122   3.177   1.650  1.00  0.00           H  
HETATM   48  H21 UNL     1      -0.518   0.438   3.946  1.00  0.00           H  
HETATM   49  H22 UNL     1       1.280   0.751   4.056  1.00  0.00           H  
HETATM   50  H23 UNL     1       1.125  -1.412   0.711  1.00  0.00           H  
HETATM   51  H24 UNL     1       2.821   0.568   2.266  1.00  0.00           H  
HETATM   52  H25 UNL     1       3.177  -1.141   1.973  1.00  0.00           H  
HETATM   53  H26 UNL     1       4.428   0.459   0.447  1.00  0.00           H  
HETATM   54  H27 UNL     1       2.896   1.155  -0.066  1.00  0.00           H  
HETATM   55  H28 UNL     1       3.612  -0.334  -1.815  1.00  0.00           H  
HETATM   56  H29 UNL     1       2.158  -0.977  -1.069  1.00  0.00           H  
HETATM   57  H30 UNL     1       3.251  -2.734   0.059  1.00  0.00           H  
HETATM   58  H31 UNL     1       3.755  -2.664  -1.615  1.00  0.00           H  
HETATM   59  H32 UNL     1       5.590  -1.596   0.617  1.00  0.00           H  
HETATM   60  H33 UNL     1       5.587  -3.269  -0.046  1.00  0.00           H  
HETATM   61  H34 UNL     1       6.127  -2.398  -2.284  1.00  0.00           H  
HETATM   62  H35 UNL     1       7.352  -2.045  -1.067  1.00  0.00           H  
HETATM   63  H36 UNL     1       7.102   2.615  -0.630  1.00  0.00           H  
HETATM   64  H37 UNL     1       5.639   2.241  -1.606  1.00  0.00           H  
HETATM   65  H38 UNL     1       7.304   2.112  -2.363  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3   31   32
CONECT    3    4   33   34
CONECT    4    5   35   36
CONECT    5    6    7    8
CONECT    6   37   38   39
CONECT    7   40
CONECT    8    9   41   42
CONECT    9   10   10   43
CONECT   10   11   44
CONECT   11   12   17   45
CONECT   12   13   14   46
CONECT   13   47
CONECT   14   15   48   49
CONECT   15   16   16   17
CONECT   17   18   50
CONECT   18   19   51   52
CONECT   19   20   53   54
CONECT   20   21   55   56
CONECT   21   22   57   58
CONECT   22   23   59   60
CONECT   23   24   61   62
CONECT   24   25   25   26
CONECT   26   27
CONECT   27   63   64   65
END

HMDB0015064
     RDKit          3D
Misoprostol
 65 65  0  0  0  0  0  0  0  0999 V2000
   -8.1306   -0.1375   -0.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3393    0.5601   -1.4959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9355    0.8842   -1.0768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1301   -0.3196   -0.7153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7186    0.1012   -0.3011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9128    1.0143    0.9042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1880    0.7976   -1.3578 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9232   -1.0919    0.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5351   -0.8077    0.5159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9498    0.3684    0.5457 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4410    0.6488    0.9590 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3424    1.4853    2.2435 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3213    2.4671    2.2842 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4366    0.5034    3.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6640   -0.8313    2.7445 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4498   -1.9153    3.2115 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2318   -0.5341    1.3800 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6878   -0.2567    1.5092 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3595    0.2041    0.2589 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2738   -0.7719   -0.8771 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8779   -2.0883   -0.6310 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3216   -2.1855   -0.3121 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2958   -1.7633   -1.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2833   -0.3778   -1.8163 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8940   -0.0096   -2.9714 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7251    0.6455   -0.9626 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7047    1.9681   -1.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7523    0.0964    0.5805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1919    0.1989   -0.4864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1445   -1.2265   -0.6479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8436    1.5227   -1.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3829   -0.0369   -2.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4468    1.3520   -1.9815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9331    1.6488   -0.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0799   -1.0185   -1.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6265   -0.8837    0.1165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9517    0.9473    1.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7474    2.0611    0.6488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2686    0.6534    1.7484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4702    1.7601   -1.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8726   -1.7731   -0.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4798   -1.6724    0.8833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8857   -1.6429    0.8388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5425    1.2352    0.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9018    1.2646    0.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6371    2.0086    2.2844 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1220    3.1770    1.6504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5183    0.4382    3.9460 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2796    0.7513    4.0562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1252   -1.4122    0.7109 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8215    0.5684    2.2655 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1775   -1.1408    1.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4276    0.4585    0.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8961    1.1548   -0.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6123   -0.3342   -1.8147 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1580   -0.9766   -1.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2506   -2.7336    0.0590 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7549   -2.6645   -1.6151 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5899   -1.5961    0.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5868   -3.2685   -0.0461 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1270   -2.3981   -2.2840 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3517   -2.0446   -1.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1024    2.6152   -0.6300 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6387    2.2411   -1.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3044    2.1116   -2.3629 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
  5  7  1  0
  5  8  1  0
  8  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  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 17 11  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  6 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  0
 10 44  1  0
 11 45  1  6
 12 46  1  6
 13 47  1  0
 14 48  1  0
 14 49  1  0
 17 50  1  6
 18 51  1  0
 18 52  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 21 57  1  0
 21 58  1  0
 22 59  1  0
 22 60  1  0
 23 61  1  0
 23 62  1  0
 27 63  1  0
 27 64  1  0
 27 65  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Cytotec	Kegg
Apo-misoprostol	HMDB
Apotex brand OF misoprostol	HMDB
Glefos	HMDB
Misoprostol pfizer brand	HMDB
Misoprostol, (11alpha,13E,16R)-isomer	HMDB
Misoprostol, (11alpha.13E,16S)-isomer	HMDB
Misoprostol, (11beta,13E,16S)-isomer	HMDB
Apo misoprostol	HMDB
Grunenthal brand OF misoprostol	HMDB
Misoprostol grunenthal brand	HMDB
Misoprostol novopharm brand	HMDB
Misoprostol, (11alpha,13Z)-(+-)-isomer	HMDB
Misoprostol, (11beta,13E,16R)-isomer	HMDB
Misoprostol apotex brand	HMDB
Misoprostol, (11alpha,13E)-isomer	HMDB
Misoprostol, (11beta,13E)-(+-)-isomer	HMDB
Novo misoprostol	HMDB
Novo-misoprostol	HMDB
Novopharm brand OF misoprostol	HMDB
Pfizer brand OF misoprostol	HMDB

Chemical Formula

C₂₂H₃₈O₅

Average Molecular Weight

382.5341

Monoisotopic Molecular Weight

382.271924326

IUPAC Name

methyl 7-[(1R,2R,3R)-3-hydroxy-2-[(1E)-4-hydroxy-4-methyloct-1-en-1-yl]-5-oxocyclopentyl]heptanoate

Traditional Name

misoprostol

CAS Registry Number

59122-46-2

SMILES

CCCCC(C)(O)C\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC

InChI Identifier

InChI=1S/C22H38O5/c1-4-5-14-22(2,26)15-10-12-18-17(19(23)16-20(18)24)11-8-6-7-9-13-21(25)27-3/h10,12,17-18,20,24,26H,4-9,11,13-16H2,1-3H3/b12-10+/t17-,18-,20-,22?/m1/s1

InChI Key

OJLOPKGSLYJEMD-URPKTTJQSA-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 acid ester
Fatty acid methyl ester
Cyclopentanol
Cyclic alcohol
Tertiary alcohol
Methyl ester
Secondary alcohol
Ketone
Carboxylic acid ester
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015064)
Extracellular (HMDB: HMDB0015064)

Process

Not Available

Role

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.016 g/L	Not Available
LogP	3.6	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.016 g/L	ALOGPS
logP	3.88	ALOGPS
logP	3.86	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	14.68	ChemAxon
pKa (Strongest Basic)	-0.95	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	14	ChemAxon
Refractivity	107.88 m³·mol⁻¹	ChemAxon
Polarizability	45.38 Å³	ChemAxon
Number of Rings	1	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]+	195.549	31661259
DarkChem	[M-H]-	192.617	31661259
DeepCCS	[M+H]+	208.187	30932474
DeepCCS	[M-H]-	205.829	30932474
DeepCCS	[M-2H]-	239.346	30932474
DeepCCS	[M+Na]+	214.576	30932474
AllCCS	[M+H]+	201.9	32859911
AllCCS	[M+H-H2O]+	199.5	32859911
AllCCS	[M+NH4]+	204.1	32859911
AllCCS	[M+Na]+	204.7	32859911
AllCCS	[M-H]-	198.8	32859911
AllCCS	[M+Na-2H]-	200.7	32859911
AllCCS	[M+HCOO]-	203.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Misoprostol	CCCCC(C)(O)C\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC	3319.3	Standard polar	33892256
Misoprostol	CCCCC(C)(O)C\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC	2681.5	Standard non polar	33892256
Misoprostol	CCCCC(C)(O)C\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC	2861.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Misoprostol,1TMS,isomer #1	CCCCC(C)(C/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC)O[Si](C)(C)C	2818.4	Semi standard non polar	33892256
Misoprostol,1TMS,isomer #2	CCCCC(C)(O)C/C=C/[C@H]1[C@H](O[Si](C)(C)C)CC(=O)[C@@H]1CCCCCCC(=O)OC	2732.1	Semi standard non polar	33892256
Misoprostol,1TMS,isomer #3	CCCCC(C)(O)C/C=C/[C@@H]1C(CCCCCCC(=O)OC)=C(O[Si](C)(C)C)C[C@H]1O	2817.4	Semi standard non polar	33892256
Misoprostol,1TMS,isomer #4	CCCCC(C)(O)C/C=C/[C@H]1[C@H](O)C=C(O[Si](C)(C)C)[C@@H]1CCCCCCC(=O)OC	2741.8	Semi standard non polar	33892256
Misoprostol,2TMS,isomer #1	CCCCC(C)(C/C=C/[C@H]1[C@H](O[Si](C)(C)C)CC(=O)[C@@H]1CCCCCCC(=O)OC)O[Si](C)(C)C	2786.7	Semi standard non polar	33892256
Misoprostol,2TMS,isomer #2	CCCCC(C)(C/C=C/[C@@H]1C(CCCCCCC(=O)OC)=C(O[Si](C)(C)C)C[C@H]1O)O[Si](C)(C)C	2891.5	Semi standard non polar	33892256
Misoprostol,2TMS,isomer #3	CCCCC(C)(C/C=C/[C@H]1[C@H](O)C=C(O[Si](C)(C)C)[C@@H]1CCCCCCC(=O)OC)O[Si](C)(C)C	2815.3	Semi standard non polar	33892256
Misoprostol,2TMS,isomer #4	CCCCC(C)(O)C/C=C/[C@@H]1C(CCCCCCC(=O)OC)=C(O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C	2794.9	Semi standard non polar	33892256
Misoprostol,2TMS,isomer #5	CCCCC(C)(O)C/C=C/[C@H]1[C@H](O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@@H]1CCCCCCC(=O)OC	2772.8	Semi standard non polar	33892256
Misoprostol,3TMS,isomer #1	CCCCC(C)(C/C=C/[C@@H]1C(CCCCCCC(=O)OC)=C(O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C)O[Si](C)(C)C	2869.0	Semi standard non polar	33892256
Misoprostol,3TMS,isomer #1	CCCCC(C)(C/C=C/[C@@H]1C(CCCCCCC(=O)OC)=C(O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C)O[Si](C)(C)C	2858.2	Standard non polar	33892256
Misoprostol,3TMS,isomer #1	CCCCC(C)(C/C=C/[C@@H]1C(CCCCCCC(=O)OC)=C(O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C)O[Si](C)(C)C	3028.9	Standard polar	33892256
Misoprostol,3TMS,isomer #2	CCCCC(C)(C/C=C/[C@H]1[C@H](O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@@H]1CCCCCCC(=O)OC)O[Si](C)(C)C	2856.3	Semi standard non polar	33892256
Misoprostol,3TMS,isomer #2	CCCCC(C)(C/C=C/[C@H]1[C@H](O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@@H]1CCCCCCC(=O)OC)O[Si](C)(C)C	2708.3	Standard non polar	33892256
Misoprostol,3TMS,isomer #2	CCCCC(C)(C/C=C/[C@H]1[C@H](O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@@H]1CCCCCCC(=O)OC)O[Si](C)(C)C	3111.1	Standard polar	33892256
Misoprostol,1TBDMS,isomer #1	CCCCC(C)(C/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC)O[Si](C)(C)C(C)(C)C	3059.9	Semi standard non polar	33892256
Misoprostol,1TBDMS,isomer #2	CCCCC(C)(O)C/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)CC(=O)[C@@H]1CCCCCCC(=O)OC	2945.9	Semi standard non polar	33892256
Misoprostol,1TBDMS,isomer #3	CCCCC(C)(O)C/C=C/[C@@H]1C(CCCCCCC(=O)OC)=C(O[Si](C)(C)C(C)(C)C)C[C@H]1O	3033.5	Semi standard non polar	33892256
Misoprostol,1TBDMS,isomer #4	CCCCC(C)(O)C/C=C/[C@H]1[C@H](O)C=C(O[Si](C)(C)C(C)(C)C)[C@@H]1CCCCCCC(=O)OC	2970.5	Semi standard non polar	33892256
Misoprostol,2TBDMS,isomer #1	CCCCC(C)(C/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)CC(=O)[C@@H]1CCCCCCC(=O)OC)O[Si](C)(C)C(C)(C)C	3242.5	Semi standard non polar	33892256
Misoprostol,2TBDMS,isomer #2	CCCCC(C)(C/C=C/[C@@H]1C(CCCCCCC(=O)OC)=C(O[Si](C)(C)C(C)(C)C)C[C@H]1O)O[Si](C)(C)C(C)(C)C	3339.9	Semi standard non polar	33892256
Misoprostol,2TBDMS,isomer #3	CCCCC(C)(C/C=C/[C@H]1[C@H](O)C=C(O[Si](C)(C)C(C)(C)C)[C@@H]1CCCCCCC(=O)OC)O[Si](C)(C)C(C)(C)C	3268.3	Semi standard non polar	33892256
Misoprostol,2TBDMS,isomer #4	CCCCC(C)(O)C/C=C/[C@@H]1C(CCCCCCC(=O)OC)=C(O[Si](C)(C)C(C)(C)C)C[C@H]1O[Si](C)(C)C(C)(C)C	3235.5	Semi standard non polar	33892256
Misoprostol,2TBDMS,isomer #5	CCCCC(C)(O)C/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)[C@@H]1CCCCCCC(=O)OC	3225.1	Semi standard non polar	33892256
Misoprostol,3TBDMS,isomer #1	CCCCC(C)(C/C=C/[C@@H]1C(CCCCCCC(=O)OC)=C(O[Si](C)(C)C(C)(C)C)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3523.7	Semi standard non polar	33892256
Misoprostol,3TBDMS,isomer #1	CCCCC(C)(C/C=C/[C@@H]1C(CCCCCCC(=O)OC)=C(O[Si](C)(C)C(C)(C)C)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3327.9	Standard non polar	33892256
Misoprostol,3TBDMS,isomer #1	CCCCC(C)(C/C=C/[C@@H]1C(CCCCCCC(=O)OC)=C(O[Si](C)(C)C(C)(C)C)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3241.1	Standard polar	33892256
Misoprostol,3TBDMS,isomer #2	CCCCC(C)(C/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)[C@@H]1CCCCCCC(=O)OC)O[Si](C)(C)C(C)(C)C	3523.9	Semi standard non polar	33892256
Misoprostol,3TBDMS,isomer #2	CCCCC(C)(C/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)[C@@H]1CCCCCCC(=O)OC)O[Si](C)(C)C(C)(C)C	3059.4	Standard non polar	33892256
Misoprostol,3TBDMS,isomer #2	CCCCC(C)(C/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)[C@@H]1CCCCCCC(=O)OC)O[Si](C)(C)C(C)(C)C	3278.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Misoprostol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zgl-7669000000-5ba5f8c705e7fe123902	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Misoprostol GC-MS (2 TMS) - 70eV, Positive	splash10-03di-8401960000-4f4e8e532189a747dc22	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Misoprostol 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 - Misoprostol 10V, Positive-QTOF	splash10-015a-0009000000-c605e40ea4ceb467e6ed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Misoprostol 20V, Positive-QTOF	splash10-05ng-5279000000-ca00a188c62568615a83	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Misoprostol 40V, Positive-QTOF	splash10-0006-9320000000-392c189929e030f4922b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Misoprostol 10V, Negative-QTOF	splash10-001i-0009000000-9a82f88089f5b6631e26	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Misoprostol 20V, Negative-QTOF	splash10-01q9-1019000000-8d92776885f140f8b37d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Misoprostol 40V, Negative-QTOF	splash10-05fu-9544000000-f3c86ea095acacec08ba	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Misoprostol 10V, Positive-QTOF	splash10-00l2-0019000000-a30a015b55a7d64d4e49	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Misoprostol 20V, Positive-QTOF	splash10-0002-9376000000-a19eba8dafb15c38a80a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Misoprostol 40V, Positive-QTOF	splash10-052e-7900000000-ae532ea752261cff1c63	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Misoprostol 10V, Negative-QTOF	splash10-03e9-0009000000-9a1f646784188d0f175d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Misoprostol 20V, Negative-QTOF	splash10-01pk-0029000000-7b266207147b4e586bdc	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Misoprostol 40V, Negative-QTOF	splash10-0ufv-8689000000-1772fe79b59691de0087	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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 DB00929	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00929	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00929

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4445541

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Misoprostol

METLIN ID

Not Available

PubChem Compound

5282381

PDB ID

Not Available

ChEBI ID

122391

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

Rocha J: Brazil investigates drug's possible link with birth defects. BMJ. 1994 Sep 24;309(6957):757-8. [PubMed:7950553 ]
Costa SH, Vessey MP: Misoprostol and illegal abortion in Rio de Janeiro, Brazil. Lancet. 1993 May 15;341(8855):1258-61. [PubMed:8098402 ]
Coelho HL, Teixeira AC, Cruz Mde F, Gonzaga SL, Arrais PS, Luchini L, La Vecchia C, Tognoni G: Misoprostol: the experience of women in Fortaleza, Brazil. Contraception. 1994 Feb;49(2):101-10. [PubMed:8143449 ]
Barbosa RM, Arilha M: The Brazilian experience with Cytotec. Stud Fam Plann. 1993 Jul-Aug;24(4):236-40. [PubMed:8212093 ]
Gonzalez CH, Vargas FR, Perez AB, Kim CA, Brunoni D, Marques-Dias MJ, Leone CR, Correa Neto J, Llerena Junior JC, de Almeida JC: Limb deficiency with or without Mobius sequence in seven Brazilian children associated with misoprostol use in the first trimester of pregnancy. Am J Med Genet. 1993 Aug 1;47(1):59-64. [PubMed:8368254 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

Enzyme Details

1. Prostaglandin E2 receptor EP4 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(s) proteins that stimulate adenylate cyclase. Has a relaxing effect on smooth muscle. May play an important role in regulating renal hemodynamics, intestinal epithelial transport, adrenal aldosterone secretion, and uterine function
Gene Name:: PTGER4
Uniprot ID:: P35408
Molecular weight:: 53118.8

References

Nakae K, Hayashi F, Hayashi M, Yamamoto N, Iino T, Yoshikawa S, Gupta J: Functional role of prostacyclin receptor in rat dorsal root ganglion neurons. Neurosci Lett. 2005 Nov 18;388(3):132-7. [PubMed:16039053 ]
Li J, Liang X, Wang Q, Breyer RM, McCullough L, Andreasson K: Misoprostol, an anti-ulcer agent and PGE2 receptor agonist, protects against cerebral ischemia. Neurosci Lett. 2008 Jun 20;438(2):210-5. doi: 10.1016/j.neulet.2008.04.054. Epub 2008 Apr 20. [PubMed:18472336 ]
Guan Y, Stillman BA, Zhang Y, Schneider A, Saito O, Davis LS, Redha R, Breyer RM, Breyer MD: Cloning and expression of the rabbit prostaglandin EP2 receptor. BMC Pharmacol. 2002 Jun 27;2:14. [PubMed:12097143 ]
Kiriyama M, Ushikubi F, Kobayashi T, Hirata M, Sugimoto Y, Narumiya S: Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells. Br J Pharmacol. 1997 Sep;122(2):217-24. [PubMed:9313928 ]
Nataraj C, Thomas DW, Tilley SL, Nguyen MT, Mannon R, Koller BH, Coffman TM: Receptors for prostaglandin E(2) that regulate cellular immune responses in the mouse. J Clin Invest. 2001 Oct;108(8):1229-35. [PubMed:11602631 ]
Crider JY, Xu SX, Sharif NA: Pharmacology of functional endogenous IP prostanoid receptors in NCB-20 cells: comparison with binding data from human platelets. Prostaglandins Leukot Essent Fatty Acids. 2001 Nov-Dec;65(5-6):253-8. [PubMed:11993717 ]

Enzyme Details

2. Prostaglandin E2 receptor EP3 subtype

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Receptor for prostaglandin E2 (PGE2); the EP3 receptor may be involved in inhibition of gastric acid secretion, modulation of neurotransmitter release in central and peripheral neurons, inhibition of sodium and water reabsorption in kidney tubulus and contraction in uterine smooth muscle. The activity of this receptor can couple to both the inhibition of adenylate cyclase mediated by G-I proteins, and to an elevation of intracellular calcium. The various isoforms have identical ligand binding properties but can interact with different second messenger systems
Gene Name:: PTGER3
Uniprot ID:: P43115
Molecular weight:: 43309.3

References

Nakae K, Hayashi F, Hayashi M, Yamamoto N, Iino T, Yoshikawa S, Gupta J: Functional role of prostacyclin receptor in rat dorsal root ganglion neurons. Neurosci Lett. 2005 Nov 18;388(3):132-7. [PubMed:16039053 ]
Li J, Liang X, Wang Q, Breyer RM, McCullough L, Andreasson K: Misoprostol, an anti-ulcer agent and PGE2 receptor agonist, protects against cerebral ischemia. Neurosci Lett. 2008 Jun 20;438(2):210-5. doi: 10.1016/j.neulet.2008.04.054. Epub 2008 Apr 20. [PubMed:18472336 ]
Guan Y, Stillman BA, Zhang Y, Schneider A, Saito O, Davis LS, Redha R, Breyer RM, Breyer MD: Cloning and expression of the rabbit prostaglandin EP2 receptor. BMC Pharmacol. 2002 Jun 27;2:14. [PubMed:12097143 ]
Kiriyama M, Ushikubi F, Kobayashi T, Hirata M, Sugimoto Y, Narumiya S: Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells. Br J Pharmacol. 1997 Sep;122(2):217-24. [PubMed:9313928 ]
Nataraj C, Thomas DW, Tilley SL, Nguyen MT, Mannon R, Koller BH, Coffman TM: Receptors for prostaglandin E(2) that regulate cellular immune responses in the mouse. J Clin Invest. 2001 Oct;108(8):1229-35. [PubMed:11602631 ]

Enzyme Details

3. Prostaglandin E2 receptor EP2 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(s) proteins that stimulate adenylate cyclase. The subsequent raise in intracellular cAMP is responsible for the relaxing effect of this receptor on smooth muscle
Gene Name:: PTGER2
Uniprot ID:: P43116
Molecular weight:: 39759.9

References

Nakae K, Hayashi F, Hayashi M, Yamamoto N, Iino T, Yoshikawa S, Gupta J: Functional role of prostacyclin receptor in rat dorsal root ganglion neurons. Neurosci Lett. 2005 Nov 18;388(3):132-7. [PubMed:16039053 ]
Li J, Liang X, Wang Q, Breyer RM, McCullough L, Andreasson K: Misoprostol, an anti-ulcer agent and PGE2 receptor agonist, protects against cerebral ischemia. Neurosci Lett. 2008 Jun 20;438(2):210-5. doi: 10.1016/j.neulet.2008.04.054. Epub 2008 Apr 20. [PubMed:18472336 ]
Guan Y, Stillman BA, Zhang Y, Schneider A, Saito O, Davis LS, Redha R, Breyer RM, Breyer MD: Cloning and expression of the rabbit prostaglandin EP2 receptor. BMC Pharmacol. 2002 Jun 27;2:14. [PubMed:12097143 ]
Kiriyama M, Ushikubi F, Kobayashi T, Hirata M, Sugimoto Y, Narumiya S: Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells. Br J Pharmacol. 1997 Sep;122(2):217-24. [PubMed:9313928 ]
Nataraj C, Thomas DW, Tilley SL, Nguyen MT, Mannon R, Koller BH, Coffman TM: Receptors for prostaglandin E(2) that regulate cellular immune responses in the mouse. J Clin Invest. 2001 Oct;108(8):1229-35. [PubMed:11602631 ]

Showing metabocard for Misoprostol (HMDB0015064)

MOL for HMDB0015064 (Misoprostol)

3D MOL for HMDB0015064 (Misoprostol)

3D SDF for HMDB0015064 (Misoprostol)

3D-SDF for HMDB0015064 (Misoprostol)

PDB for HMDB0015064 (Misoprostol)

3D PDB for HMDB0015064 (Misoprostol)

SMILES for HMDB0015064 (Misoprostol)

INCHI for HMDB0015064 (Misoprostol)

Structure for HMDB0015064 (Misoprostol)

3D Structure for HMDB0015064 (Misoprostol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References