Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 15:12:44 UTC

Update Date

2022-03-07 02:49:18 UTC

HMDB ID

HMDB0003247

Secondary Accession Numbers

HMDB03247

Metabolite Identification

Common Name

20-Hydroxy-PGE2

Description

20-hydroxy PGE2 is a product of cytochrome P450 metabolism of PGE2. ω-Oxidation at C-20 followed by beta-oxidation and the loss of up to 4 carbons from the lower side chain is a prominent metabolic pathway for PGE2. 20-hydroxy PGE2 is the putative first intermediate in this chain of chemical transformations. -- www.caymanchem.com. Dinoprostone is a naturally occurring prostaglandin E2 (PGE2) and the most common and most biologically active of the mammalian prostaglandins. It has important effects in labour and also stimulates osteoblasts to release factors which stimulate bone resorption by osteoclasts (a type of bone cell that removes bone tissue by removing the bone's mineralized matrix). PGE2 has been shown to increase vasodilation and cAMP production, to enhance the effects of bradykinin and histamine, to induce uterine contractions and to activate platelet aggregation. PGE2 is also responsible for maintaining the open passageway of the fetal ductus arteriosus; decreasing T-cell proliferation and lymphocyte migration and activating the secretion of IL-1alpha and IL-2. PGE2 exhibits both pro- and anti-inflammatory effects, particularly on dendritic cells (DC). Depending on the nature of maturation signals, PGE2 has different and sometimes opposite effects on DC biology. PGE2 exerts an inhibitory action, reducing the maturation of DC and their ability to present antigen. PGE2 has also been shown to stimulate DC and promote IL-12 production when given in combination with TNF-alpha. PGE2 is an environmentally bioactive substance. Its action is prolonged and sustained by other factors especially IL-10. It modulates the activities of professional DC by acting on their differentiation, maturation and their ability to secrete cytokines. PGE2 is a potent inducer of IL-10 in bone marrow-derived DC (BM-DC), and PGE2-induced IL-10 is a key regulator of the BM-DC pro-inflammatory phenotype. (PMID: 16978535 )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


  Mrv0541 02231219402D          

 26 26  0  0  1  0            999 V2000
   30.5593  -13.5256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.4172  -10.2256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.0114  -16.2305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6257  -13.5969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1841  -14.9559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.6619  -17.9376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2738  -13.9381    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   33.4172  -11.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9882  -13.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7028  -11.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9882  -12.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7028  -12.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7533  -15.4658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5818  -14.6587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5380  -15.7207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1072  -16.2305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2267  -16.4856    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   30.5593  -16.0006    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   29.8919  -16.4856    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   30.9718  -17.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7972  -14.4038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7095  -16.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4942  -16.7826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2738  -14.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5593  -15.1756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1468  -17.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  1  0  0  0
  2  8  1  0  0  0  0
 17  3  1  6  0  0  0
  4 21  1  0  0  0  0
  5 21  2  0  0  0  0
  6 26  2  0  0  0  0
  7  9  1  0  0  0  0
  7 24  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 21  1  0  0  0  0
 15 22  1  0  0  0  0
 19 16  1  6  0  0  0
 16 23  1  0  0  0  0
 17 18  1  0  0  0  0
 17 20  1  0  0  0  0
 18 19  1  0  0  0  0
 18 25  1  1  0  0  0
 19 26  1  0  0  0  0
 20 26  1  0  0  0  0
 22 23  2  0  0  0  0
 24 25  2  0  0  0  0
M  END

HMDB0003247
     RDKit          3D
20-Hydroxy-PGE2
 58 58  0  0  0  0  0  0  0  0999 V2000
   -7.1200   -3.5549   -0.3493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3558   -2.3343   -0.2008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6449   -1.8866   -0.0018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2136   -1.3909   -0.2453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6752    0.0404   -0.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3988    0.8976   -0.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5086    0.4544    0.9497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2961   -0.0311    0.7790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6596   -0.1981   -0.5222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3862    0.5765   -0.7120 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5292    2.0417   -0.5864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4687    2.7428   -0.8420 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211    2.5052   -0.0561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0129    1.4739    1.0368 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0057    1.7378    1.9875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3167    0.1897    0.3168 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8170   -0.3844   -0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0537    0.0387   -0.4495 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1310   -0.6428   -1.2416 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0729    0.3074   -1.5862 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7763   -1.7456   -0.4803 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4183   -1.3246    0.7858 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5202   -0.3279    0.6846 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6776   -0.8135   -0.1605 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7557    0.2450   -0.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2662    1.4279   -0.7839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1274   -1.2190   -0.5758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6810   -1.4354   -1.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5263   -1.6690    0.5768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1922    0.1791    0.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3800    0.3420   -0.8481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7846    1.9378    0.1187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0578    0.8165   -1.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8786    0.5309    1.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7363   -0.3319    1.6572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2918    0.0009   -1.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3510   -1.2860   -0.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9843    0.4129   -1.7557 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5318    2.3864   -0.8739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2618    3.5356    0.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9970    1.5221    1.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9053    2.7119    2.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7486   -0.5262    1.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6151   -1.2924   -1.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3116    0.9199    0.1146 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7011   -1.0026   -2.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6836    1.1718   -1.8787 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9961   -2.5062   -0.2579 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5495   -2.2530   -1.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8234   -2.2270    1.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6222   -0.8607    1.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8969   -0.1796    1.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2382    0.6681    0.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1426   -1.7008    0.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3853   -1.1001   -1.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0373    0.4637    0.8359 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6492   -0.1322   -0.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0502    2.0783   -0.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 16 10  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  6
 13 39  1  0
 13 40  1  0
 14 41  1  1
 15 42  1  0
 16 43  1  1
 17 44  1  0
 18 45  1  0
 19 46  1  6
 20 47  1  0
 21 48  1  0
 21 49  1  0
 22 50  1  0
 22 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  0
 24 55  1  0
 25 56  1  0
 25 57  1  0
 26 58  1  0
M  END


  Mrv0541 02231219402D          

 26 26  0  0  1  0            999 V2000
   30.5593  -13.5256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.4172  -10.2256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.0114  -16.2305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6257  -13.5969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1841  -14.9559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.6619  -17.9376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2738  -13.9381    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   33.4172  -11.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9882  -13.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7028  -11.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9882  -12.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7028  -12.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7533  -15.4658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5818  -14.6587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5380  -15.7207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1072  -16.2305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2267  -16.4856    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   30.5593  -16.0006    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   29.8919  -16.4856    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   30.9718  -17.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7972  -14.4038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7095  -16.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4942  -16.7826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2738  -14.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5593  -15.1756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1468  -17.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  1  0  0  0
  2  8  1  0  0  0  0
 17  3  1  6  0  0  0
  4 21  1  0  0  0  0
  5 21  2  0  0  0  0
  6 26  2  0  0  0  0
  7  9  1  0  0  0  0
  7 24  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 21  1  0  0  0  0
 15 22  1  0  0  0  0
 19 16  1  6  0  0  0
 16 23  1  0  0  0  0
 17 18  1  0  0  0  0
 17 20  1  0  0  0  0
 18 19  1  0  0  0  0
 18 25  1  1  0  0  0
 19 26  1  0  0  0  0
 20 26  1  0  0  0  0
 22 23  2  0  0  0  0
 24 25  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003247

> <DATABASE_NAME>
hmdb

> <SMILES>
OCCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O6/c21-13-7-3-4-8-15(22)11-12-17-16(18(23)14-19(17)24)9-5-1-2-6-10-20(25)26/h1,5,11-12,15-17,19,21-22,24H,2-4,6-10,13-14H2,(H,25,26)/b5-1-,12-11+/t15-,16+,17+,19+/m0/s1

> <INCHI_KEY>
AZIGEYVZEVXWAD-NZGURKHLSA-N

> <FORMULA>
C20H32O6

> <MOLECULAR_WEIGHT>
368.4645

> <EXACT_MASS>
368.219888756

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
41.55616853833172

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z)-7-[(1R,2R,3R)-2-[(1E,3S)-3,8-dihydroxyoct-1-en-1-yl]-3-hydroxy-5-oxocyclopentyl]hept-5-enoic acid

> <ALOGPS_LOGP>
2.02

> <JCHEM_LOGP>
1.788591520333332

> <ALOGPS_LOGS>
-3.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.678908140241287

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.30335974551424

> <JCHEM_PKA_STRONGEST_BASIC>
-1.470804554742306

> <JCHEM_POLAR_SURFACE_AREA>
115.06

> <JCHEM_REFRACTIVITY>
101.3638

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.34e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
20-Hydroxy-PGE2

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0003247
     RDKit          3D
20-Hydroxy-PGE2
 58 58  0  0  0  0  0  0  0  0999 V2000
   -7.1200   -3.5549   -0.3493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3558   -2.3343   -0.2008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6449   -1.8866   -0.0018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2136   -1.3909   -0.2453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6752    0.0404   -0.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3988    0.8976   -0.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5086    0.4544    0.9497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2961   -0.0311    0.7790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6596   -0.1981   -0.5222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3862    0.5765   -0.7120 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5292    2.0417   -0.5864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4687    2.7428   -0.8420 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211    2.5052   -0.0561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0129    1.4739    1.0368 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0057    1.7378    1.9875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3167    0.1897    0.3168 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8170   -0.3844   -0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0537    0.0387   -0.4495 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1310   -0.6428   -1.2416 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0729    0.3074   -1.5862 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7763   -1.7456   -0.4803 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4183   -1.3246    0.7858 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5202   -0.3279    0.6846 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6776   -0.8135   -0.1605 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7557    0.2450   -0.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2662    1.4279   -0.7839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1274   -1.2190   -0.5758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6810   -1.4354   -1.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5263   -1.6690    0.5768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1922    0.1791    0.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3800    0.3420   -0.8481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7846    1.9378    0.1187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0578    0.8165   -1.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8786    0.5309    1.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7363   -0.3319    1.6572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2918    0.0009   -1.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3510   -1.2860   -0.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9843    0.4129   -1.7557 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5318    2.3864   -0.8739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2618    3.5356    0.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9970    1.5221    1.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9053    2.7119    2.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7486   -0.5262    1.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6151   -1.2924   -1.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3116    0.9199    0.1146 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7011   -1.0026   -2.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6836    1.1718   -1.8787 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9961   -2.5062   -0.2579 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5495   -2.2530   -1.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8234   -2.2270    1.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6222   -0.8607    1.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8969   -0.1796    1.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2382    0.6681    0.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1426   -1.7008    0.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3853   -1.1001   -1.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0373    0.4637    0.8359 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6492   -0.1322   -0.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0502    2.0783   -0.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 16 10  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  6
 13 39  1  0
 13 40  1  0
 14 41  1  1
 15 42  1  0
 16 43  1  1
 17 44  1  0
 18 45  1  0
 19 46  1  6
 20 47  1  0
 21 48  1  0
 21 49  1  0
 22 50  1  0
 22 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  0
 24 55  1  0
 25 56  1  0
 25 57  1  0
 26 58  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      57.044 -25.248   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      62.379 -19.088   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      59.755 -30.297   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      47.835 -25.381   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      47.010 -27.918   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      55.369 -33.484   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      58.378 -26.018   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      62.379 -20.628   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      59.711 -25.248   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      61.045 -21.398   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      59.711 -23.708   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      61.045 -22.938   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      49.939 -28.869   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      49.619 -27.363   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      51.404 -29.345   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      54.333 -30.297   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      58.290 -30.773   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      57.044 -29.868   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      55.798 -30.773   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      57.814 -32.238   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      48.155 -26.887   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      51.724 -30.852   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      53.189 -31.328   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      58.378 -27.558   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      57.044 -28.328   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      56.274 -32.238   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3   17                                                            
CONECT    4   21                                                            
CONECT    5   21                                                            
CONECT    6   26                                                            
CONECT    7    1    9   24                                                  
CONECT    8    2   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   12                                                       
CONECT   12   10   11                                                       
CONECT   13   14   15                                                       
CONECT   14   13   21                                                       
CONECT   15   13   22                                                       
CONECT   16   19   23                                                       
CONECT   17    3   18   20                                                  
CONECT   18   17   19   25                                                  
CONECT   19   16   18   26                                                  
CONECT   20   17   26                                                       
CONECT   21    4    5   14                                                  
CONECT   22   15   23                                                       
CONECT   23   16   22                                                       
CONECT   24    7   25                                                       
CONECT   25   18   24                                                       
CONECT   26    6   19   20                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   52    0
END

COMPND    HMDB0003247
HETATM    1  O1  UNL     1      -7.120  -3.555  -0.349  1.00  0.00           O  
HETATM    2  C1  UNL     1      -7.356  -2.334  -0.201  1.00  0.00           C  
HETATM    3  O2  UNL     1      -8.645  -1.887  -0.002  1.00  0.00           O  
HETATM    4  C2  UNL     1      -6.214  -1.391  -0.245  1.00  0.00           C  
HETATM    5  C3  UNL     1      -6.675   0.040  -0.049  1.00  0.00           C  
HETATM    6  C4  UNL     1      -5.399   0.898  -0.118  1.00  0.00           C  
HETATM    7  C5  UNL     1      -4.509   0.454   0.950  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.296  -0.031   0.779  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.660  -0.198  -0.522  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.386   0.576  -0.712  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.529   2.042  -0.586  1.00  0.00           C  
HETATM   12  O3  UNL     1      -2.469   2.743  -0.842  1.00  0.00           O  
HETATM   13  C10 UNL     1      -0.221   2.505  -0.056  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.013   1.474   1.037  1.00  0.00           C  
HETATM   15  O4  UNL     1      -1.006   1.738   1.987  1.00  0.00           O  
HETATM   16  C12 UNL     1      -0.317   0.190   0.317  1.00  0.00           C  
HETATM   17  C13 UNL     1       0.817  -0.384  -0.413  1.00  0.00           C  
HETATM   18  C14 UNL     1       2.054   0.039  -0.450  1.00  0.00           C  
HETATM   19  C15 UNL     1       3.131  -0.643  -1.242  1.00  0.00           C  
HETATM   20  O5  UNL     1       4.073   0.307  -1.586  1.00  0.00           O  
HETATM   21  C16 UNL     1       3.776  -1.746  -0.480  1.00  0.00           C  
HETATM   22  C17 UNL     1       4.418  -1.325   0.786  1.00  0.00           C  
HETATM   23  C18 UNL     1       5.520  -0.328   0.685  1.00  0.00           C  
HETATM   24  C19 UNL     1       6.678  -0.813  -0.160  1.00  0.00           C  
HETATM   25  C20 UNL     1       7.756   0.245  -0.222  1.00  0.00           C  
HETATM   26  O6  UNL     1       7.266   1.428  -0.784  1.00  0.00           O  
HETATM   27  H1  UNL     1      -9.127  -1.219  -0.576  1.00  0.00           H  
HETATM   28  H2  UNL     1      -5.681  -1.435  -1.217  1.00  0.00           H  
HETATM   29  H3  UNL     1      -5.526  -1.669   0.577  1.00  0.00           H  
HETATM   30  H4  UNL     1      -7.192   0.179   0.922  1.00  0.00           H  
HETATM   31  H5  UNL     1      -7.380   0.342  -0.848  1.00  0.00           H  
HETATM   32  H6  UNL     1      -5.785   1.938   0.119  1.00  0.00           H  
HETATM   33  H7  UNL     1      -5.058   0.816  -1.140  1.00  0.00           H  
HETATM   34  H8  UNL     1      -4.879   0.531   1.985  1.00  0.00           H  
HETATM   35  H9  UNL     1      -2.736  -0.332   1.657  1.00  0.00           H  
HETATM   36  H10 UNL     1      -3.292   0.001  -1.408  1.00  0.00           H  
HETATM   37  H11 UNL     1      -2.351  -1.286  -0.681  1.00  0.00           H  
HETATM   38  H12 UNL     1      -0.984   0.413  -1.756  1.00  0.00           H  
HETATM   39  H13 UNL     1       0.532   2.386  -0.874  1.00  0.00           H  
HETATM   40  H14 UNL     1      -0.262   3.536   0.336  1.00  0.00           H  
HETATM   41  H15 UNL     1       0.997   1.522   1.487  1.00  0.00           H  
HETATM   42  H16 UNL     1      -0.905   2.712   2.206  1.00  0.00           H  
HETATM   43  H17 UNL     1      -0.749  -0.526   1.060  1.00  0.00           H  
HETATM   44  H18 UNL     1       0.615  -1.292  -1.016  1.00  0.00           H  
HETATM   45  H19 UNL     1       2.312   0.920   0.115  1.00  0.00           H  
HETATM   46  H20 UNL     1       2.701  -1.003  -2.222  1.00  0.00           H  
HETATM   47  H21 UNL     1       3.684   1.172  -1.879  1.00  0.00           H  
HETATM   48  H22 UNL     1       2.996  -2.506  -0.258  1.00  0.00           H  
HETATM   49  H23 UNL     1       4.550  -2.253  -1.127  1.00  0.00           H  
HETATM   50  H24 UNL     1       4.823  -2.227   1.309  1.00  0.00           H  
HETATM   51  H25 UNL     1       3.622  -0.861   1.429  1.00  0.00           H  
HETATM   52  H26 UNL     1       5.897  -0.180   1.742  1.00  0.00           H  
HETATM   53  H27 UNL     1       5.238   0.668   0.347  1.00  0.00           H  
HETATM   54  H28 UNL     1       7.143  -1.701   0.329  1.00  0.00           H  
HETATM   55  H29 UNL     1       6.385  -1.100  -1.180  1.00  0.00           H  
HETATM   56  H30 UNL     1       8.037   0.464   0.836  1.00  0.00           H  
HETATM   57  H31 UNL     1       8.649  -0.132  -0.743  1.00  0.00           H  
HETATM   58  H32 UNL     1       7.050   2.078  -0.078  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   27
CONECT    4    5   28   29
CONECT    5    6   30   31
CONECT    6    7   32   33
CONECT    7    8    8   34
CONECT    8    9   35
CONECT    9   10   36   37
CONECT   10   11   16   38
CONECT   11   12   12   13
CONECT   13   14   39   40
CONECT   14   15   16   41
CONECT   15   42
CONECT   16   17   43
CONECT   17   18   18   44
CONECT   18   19   45
CONECT   19   20   21   46
CONECT   20   47
CONECT   21   22   48   49
CONECT   22   23   50   51
CONECT   23   24   52   53
CONECT   24   25   54   55
CONECT   25   26   56   57
CONECT   26   58
END

HMDB0003247
     RDKit          3D
20-Hydroxy-PGE2
 58 58  0  0  0  0  0  0  0  0999 V2000
   -7.1200   -3.5549   -0.3493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3558   -2.3343   -0.2008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6449   -1.8866   -0.0018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2136   -1.3909   -0.2453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6752    0.0404   -0.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3988    0.8976   -0.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5086    0.4544    0.9497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2961   -0.0311    0.7790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6596   -0.1981   -0.5222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3862    0.5765   -0.7120 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5292    2.0417   -0.5864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4687    2.7428   -0.8420 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211    2.5052   -0.0561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0129    1.4739    1.0368 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0057    1.7378    1.9875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3167    0.1897    0.3168 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8170   -0.3844   -0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0537    0.0387   -0.4495 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1310   -0.6428   -1.2416 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0729    0.3074   -1.5862 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7763   -1.7456   -0.4803 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4183   -1.3246    0.7858 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5202   -0.3279    0.6846 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6776   -0.8135   -0.1605 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7557    0.2450   -0.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2662    1.4279   -0.7839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1274   -1.2190   -0.5758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6810   -1.4354   -1.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5263   -1.6690    0.5768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1922    0.1791    0.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3800    0.3420   -0.8481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7846    1.9378    0.1187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0578    0.8165   -1.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8786    0.5309    1.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7363   -0.3319    1.6572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2918    0.0009   -1.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3510   -1.2860   -0.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9843    0.4129   -1.7557 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5318    2.3864   -0.8739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2618    3.5356    0.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9970    1.5221    1.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9053    2.7119    2.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7486   -0.5262    1.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6151   -1.2924   -1.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3116    0.9199    0.1146 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7011   -1.0026   -2.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6836    1.1718   -1.8787 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9961   -2.5062   -0.2579 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5495   -2.2530   -1.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8234   -2.2270    1.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6222   -0.8607    1.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8969   -0.1796    1.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2382    0.6681    0.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1426   -1.7008    0.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3853   -1.1001   -1.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0373    0.4637    0.8359 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6492   -0.1322   -0.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0502    2.0783   -0.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 16 10  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  6
 13 39  1  0
 13 40  1  0
 14 41  1  1
 15 42  1  0
 16 43  1  1
 17 44  1  0
 18 45  1  0
 19 46  1  6
 20 47  1  0
 21 48  1  0
 21 49  1  0
 22 50  1  0
 22 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  0
 24 55  1  0
 25 56  1  0
 25 57  1  0
 26 58  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5Z,11alpha,13E,15S)-11,15,20-Trihydroxy-9-oxoprosta-5,13-dien-1-Oic acid	ChEBI
20-Hydroxy prostaglandin e2	ChEBI
20-Hydroxy-prostaglandin e2	ChEBI
20-OH-PGE2	ChEBI
9-oxo-11R,15S,20-Trihydroxy-5Z,13E-prostadienoic acid	ChEBI
(5Z,11a,13E,15S)-11,15,20-Trihydroxy-9-oxoprosta-5,13-dien-1-Oate	Generator
(5Z,11a,13E,15S)-11,15,20-Trihydroxy-9-oxoprosta-5,13-dien-1-Oic acid	Generator
(5Z,11alpha,13E,15S)-11,15,20-Trihydroxy-9-oxoprosta-5,13-dien-1-Oate	Generator
(5Z,11Α,13E,15S)-11,15,20-trihydroxy-9-oxoprosta-5,13-dien-1-Oate	Generator
(5Z,11Α,13E,15S)-11,15,20-trihydroxy-9-oxoprosta-5,13-dien-1-Oic acid	Generator
9-oxo-11R,15S,20-Trihydroxy-5Z,13E-prostadienoate	Generator
(5Z,11(alpha),13E,15S)-11,15-Dihydroxy-9-oxo-prosta-5,13-dien-1-Oate	HMDB
(5Z,11(alpha),13E,15S)-11,15-Dihydroxy-9-oxo-prosta-5,13-dien-1-Oic acid	HMDB
20-Hydroxyprostaglandin e2	HMDB
20-Hydroxy-pge2	ChEBI

Chemical Formula

C₂₀H₃₂O₆

Average Molecular Weight

368.4645

Monoisotopic Molecular Weight

368.219888756

IUPAC Name

(5Z)-7-[(1R,2R,3R)-2-[(1E,3S)-3,8-dihydroxyoct-1-en-1-yl]-3-hydroxy-5-oxocyclopentyl]hept-5-enoic acid

Traditional Name

20-Hydroxy-PGE2

CAS Registry Number

57930-95-7

SMILES

OCCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O

InChI Identifier

InChI=1S/C20H32O6/c21-13-7-3-4-8-15(22)11-12-17-16(18(23)14-19(17)24)9-5-1-2-6-10-20(25)26/h1,5,11-12,15-17,19,21-22,24H,2-4,6-10,13-14H2,(H,25,26)/b5-1-,12-11+/t15-,16+,17+,19+/m0/s1

InChI Key

AZIGEYVZEVXWAD-NZGURKHLSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Prostaglandins and related compounds

Alternative Parents

Substituents

Prostaglandin skeleton
Long-chain fatty acid
Hydroxy fatty acid
Cyclopentanol
Fatty acid
Unsaturated fatty acid
Cyclic alcohol
Cyclic ketone
Ketone
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Primary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Prostaglandins (LMFA03010014 )

Ontology

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

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.23 g/L	ALOGPS
logP	2.02	ALOGPS
logP	1.79	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	4.3	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.06 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	101.36 m³·mol⁻¹	ChemAxon
Polarizability	41.56 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]+	191.4	31661259
DarkChem	[M-H]-	192.925	31661259
DeepCCS	[M+H]+	199.546	30932474
DeepCCS	[M-H]-	197.15	30932474
DeepCCS	[M-2H]-	231.131	30932474
DeepCCS	[M+Na]+	206.018	30932474
AllCCS	[M+H]+	193.5	32859911
AllCCS	[M+H-H2O]+	191.0	32859911
AllCCS	[M+NH4]+	195.8	32859911
AllCCS	[M+Na]+	196.5	32859911
AllCCS	[M-H]-	192.8	32859911
AllCCS	[M+Na-2H]-	194.2	32859911
AllCCS	[M+HCOO]-	195.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.6 minutes	32390414
Predicted by Siyang on May 30, 2022	11.7674 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.49 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	109.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2258.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	191.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	149.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	171.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	155.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	411.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	380.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	348.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	981.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	417.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1184.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	290.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	321.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	473.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	194.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	57.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
20-Hydroxy-PGE2	OCCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O	4688.5	Standard polar	33892256
20-Hydroxy-PGE2	OCCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O	2840.8	Standard non polar	33892256
20-Hydroxy-PGE2	OCCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O	3152.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
20-Hydroxy-PGE2,1TMS,isomer #1	C[Si](C)(C)OCCCCC[C@H](O)/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O	3131.1	Semi standard non polar	33892256
20-Hydroxy-PGE2,1TMS,isomer #2	C[Si](C)(C)O[C@H](/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O)CCCCCO	3110.6	Semi standard non polar	33892256
20-Hydroxy-PGE2,1TMS,isomer #3	C[Si](C)(C)O[C@@H]1CC(=O)[C@H](C/C=C\CCCC(=O)O)[C@H]1/C=C/[C@@H](O)CCCCCO	3034.1	Semi standard non polar	33892256
20-Hydroxy-PGE2,1TMS,isomer #4	C[Si](C)(C)OC(=O)CCC/C=C\C[C@H]1C(=O)C[C@@H](O)[C@@H]1/C=C/[C@@H](O)CCCCCO	3059.0	Semi standard non polar	33892256
20-Hydroxy-PGE2,1TMS,isomer #5	C[Si](C)(C)OC1=C(C/C=C\CCCC(=O)O)[C@@H](/C=C/[C@@H](O)CCCCCO)[C@H](O)C1	3010.1	Semi standard non polar	33892256
20-Hydroxy-PGE2,1TMS,isomer #6	C[Si](C)(C)OC1=C[C@@H](O)[C@H](/C=C/[C@@H](O)CCCCCO)[C@H]1C/C=C\CCCC(=O)O	2957.3	Semi standard non polar	33892256
20-Hydroxy-PGE2,2TMS,isomer #1	C[Si](C)(C)OCCCCC[C@@H](/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C	3087.7	Semi standard non polar	33892256
20-Hydroxy-PGE2,2TMS,isomer #10	C[Si](C)(C)OC(=O)CCC/C=C\C[C@H]1C(=O)C[C@@H](O[Si](C)(C)C)[C@@H]1/C=C/[C@@H](O)CCCCCO	2978.5	Semi standard non polar	33892256
20-Hydroxy-PGE2,2TMS,isomer #11	C[Si](C)(C)OC1=C(C/C=C\CCCC(=O)O)[C@@H](/C=C/[C@@H](O)CCCCCO)[C@H](O[Si](C)(C)C)C1	3019.8	Semi standard non polar	33892256
20-Hydroxy-PGE2,2TMS,isomer #12	C[Si](C)(C)OC1=C[C@@H](O[Si](C)(C)C)[C@H](/C=C/[C@@H](O)CCCCCO)[C@H]1C/C=C\CCCC(=O)O	2998.9	Semi standard non polar	33892256
20-Hydroxy-PGE2,2TMS,isomer #13	C[Si](C)(C)OC(=O)CCC/C=C\CC1=C(O[Si](C)(C)C)C[C@@H](O)[C@@H]1/C=C/[C@@H](O)CCCCCO	3020.1	Semi standard non polar	33892256
20-Hydroxy-PGE2,2TMS,isomer #14	C[Si](C)(C)OC(=O)CCC/C=C\C[C@H]1C(O[Si](C)(C)C)=C[C@@H](O)[C@@H]1/C=C/[C@@H](O)CCCCCO	2966.0	Semi standard non polar	33892256
20-Hydroxy-PGE2,2TMS,isomer #2	C[Si](C)(C)OCCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)O	2995.4	Semi standard non polar	33892256
20-Hydroxy-PGE2,2TMS,isomer #3	C[Si](C)(C)OCCCCC[C@H](O)/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C	3031.9	Semi standard non polar	33892256
20-Hydroxy-PGE2,2TMS,isomer #4	C[Si](C)(C)OCCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C)C[C@H]1O	3046.2	Semi standard non polar	33892256
20-Hydroxy-PGE2,2TMS,isomer #5	C[Si](C)(C)OCCCCC[C@H](O)/C=C/[C@H]1[C@H](O)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O	2966.2	Semi standard non polar	33892256
20-Hydroxy-PGE2,2TMS,isomer #6	C[Si](C)(C)O[C@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)O)CCCCCO	2986.0	Semi standard non polar	33892256
20-Hydroxy-PGE2,2TMS,isomer #7	C[Si](C)(C)OC(=O)CCC/C=C\C[C@H]1C(=O)C[C@@H](O)[C@@H]1/C=C/[C@H](CCCCCO)O[Si](C)(C)C	3036.5	Semi standard non polar	33892256
20-Hydroxy-PGE2,2TMS,isomer #8	C[Si](C)(C)OC1=C(C/C=C\CCCC(=O)O)[C@@H](/C=C/[C@H](CCCCCO)O[Si](C)(C)C)[C@H](O)C1	3056.5	Semi standard non polar	33892256
20-Hydroxy-PGE2,2TMS,isomer #9	C[Si](C)(C)OC1=C[C@@H](O)[C@H](/C=C/[C@H](CCCCCO)O[Si](C)(C)C)[C@H]1C/C=C\CCCC(=O)O	2957.9	Semi standard non polar	33892256
20-Hydroxy-PGE2,3TMS,isomer #1	C[Si](C)(C)OCCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C	2955.7	Semi standard non polar	33892256
20-Hydroxy-PGE2,3TMS,isomer #10	C[Si](C)(C)OC(=O)CCC/C=C\C[C@H]1C(=O)C[C@@H](O[Si](C)(C)C)[C@@H]1/C=C/[C@H](CCCCCO)O[Si](C)(C)C	2914.8	Semi standard non polar	33892256
20-Hydroxy-PGE2,3TMS,isomer #11	C[Si](C)(C)OC1=C(C/C=C\CCCC(=O)O)[C@@H](/C=C/[C@H](CCCCCO)O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C1	3006.8	Semi standard non polar	33892256
20-Hydroxy-PGE2,3TMS,isomer #12	C[Si](C)(C)OC1=C[C@@H](O[Si](C)(C)C)[C@H](/C=C/[C@H](CCCCCO)O[Si](C)(C)C)[C@H]1C/C=C\CCCC(=O)O	2973.2	Semi standard non polar	33892256
20-Hydroxy-PGE2,3TMS,isomer #13	C[Si](C)(C)OC(=O)CCC/C=C\CC1=C(O[Si](C)(C)C)C[C@@H](O)[C@@H]1/C=C/[C@H](CCCCCO)O[Si](C)(C)C	3026.5	Semi standard non polar	33892256
20-Hydroxy-PGE2,3TMS,isomer #14	C[Si](C)(C)OC(=O)CCC/C=C\C[C@H]1C(O[Si](C)(C)C)=C[C@@H](O)[C@@H]1/C=C/[C@H](CCCCCO)O[Si](C)(C)C	2955.3	Semi standard non polar	33892256
20-Hydroxy-PGE2,3TMS,isomer #15	C[Si](C)(C)OC(=O)CCC/C=C\CC1=C(O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)[C@@H]1/C=C/[C@@H](O)CCCCCO	3002.1	Semi standard non polar	33892256
20-Hydroxy-PGE2,3TMS,isomer #16	C[Si](C)(C)OC(=O)CCC/C=C\C[C@H]1C(O[Si](C)(C)C)=C[C@@H](O[Si](C)(C)C)[C@@H]1/C=C/[C@@H](O)CCCCCO	2969.2	Semi standard non polar	33892256
20-Hydroxy-PGE2,3TMS,isomer #2	C[Si](C)(C)OCCCCC[C@@H](/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3006.8	Semi standard non polar	33892256
20-Hydroxy-PGE2,3TMS,isomer #3	C[Si](C)(C)OCCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C)C[C@H]1O)O[Si](C)(C)C	3051.5	Semi standard non polar	33892256
20-Hydroxy-PGE2,3TMS,isomer #4	C[Si](C)(C)OCCCCC[C@@H](/C=C/[C@H]1[C@H](O)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C	2964.5	Semi standard non polar	33892256
20-Hydroxy-PGE2,3TMS,isomer #5	C[Si](C)(C)OCCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C	2945.8	Semi standard non polar	33892256
20-Hydroxy-PGE2,3TMS,isomer #6	C[Si](C)(C)OCCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C	3015.2	Semi standard non polar	33892256
20-Hydroxy-PGE2,3TMS,isomer #7	C[Si](C)(C)OCCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O	2966.9	Semi standard non polar	33892256
20-Hydroxy-PGE2,3TMS,isomer #8	C[Si](C)(C)OCCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]1O	3020.1	Semi standard non polar	33892256
20-Hydroxy-PGE2,3TMS,isomer #9	C[Si](C)(C)OCCCCC[C@H](O)/C=C/[C@H]1[C@H](O)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C	2951.4	Semi standard non polar	33892256
20-Hydroxy-PGE2,4TMS,isomer #1	C[Si](C)(C)OCCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2949.8	Semi standard non polar	33892256
20-Hydroxy-PGE2,4TMS,isomer #2	C[Si](C)(C)OCCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C)O[Si](C)(C)C	2998.8	Semi standard non polar	33892256
20-Hydroxy-PGE2,4TMS,isomer #3	C[Si](C)(C)OCCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C	2963.3	Semi standard non polar	33892256
20-Hydroxy-PGE2,4TMS,isomer #4	C[Si](C)(C)OCCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]1O)O[Si](C)(C)C	3022.5	Semi standard non polar	33892256
20-Hydroxy-PGE2,4TMS,isomer #5	C[Si](C)(C)OCCCCC[C@@H](/C=C/[C@H]1[C@H](O)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2968.4	Semi standard non polar	33892256
20-Hydroxy-PGE2,4TMS,isomer #6	C[Si](C)(C)OCCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C	2973.4	Semi standard non polar	33892256
20-Hydroxy-PGE2,4TMS,isomer #7	C[Si](C)(C)OCCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C	2958.5	Semi standard non polar	33892256
20-Hydroxy-PGE2,4TMS,isomer #8	C[Si](C)(C)OC(=O)CCC/C=C\CC1=C(O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)[C@@H]1/C=C/[C@H](CCCCCO)O[Si](C)(C)C	2982.4	Semi standard non polar	33892256
20-Hydroxy-PGE2,4TMS,isomer #9	C[Si](C)(C)OC(=O)CCC/C=C\C[C@H]1C(O[Si](C)(C)C)=C[C@@H](O[Si](C)(C)C)[C@@H]1/C=C/[C@H](CCCCCO)O[Si](C)(C)C	2964.9	Semi standard non polar	33892256
20-Hydroxy-PGE2,5TMS,isomer #1	C[Si](C)(C)OCCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C)O[Si](C)(C)C	3010.3	Semi standard non polar	33892256
20-Hydroxy-PGE2,5TMS,isomer #1	C[Si](C)(C)OCCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C)O[Si](C)(C)C	3052.9	Standard non polar	33892256
20-Hydroxy-PGE2,5TMS,isomer #1	C[Si](C)(C)OCCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C)O[Si](C)(C)C	3054.3	Standard polar	33892256
20-Hydroxy-PGE2,5TMS,isomer #2	C[Si](C)(C)OCCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2994.1	Semi standard non polar	33892256
20-Hydroxy-PGE2,5TMS,isomer #2	C[Si](C)(C)OCCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2857.8	Standard non polar	33892256
20-Hydroxy-PGE2,5TMS,isomer #2	C[Si](C)(C)OCCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3123.2	Standard polar	33892256
20-Hydroxy-PGE2,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCCC[C@H](O)/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O	3378.0	Semi standard non polar	33892256
20-Hydroxy-PGE2,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H](/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O)CCCCCO	3353.1	Semi standard non polar	33892256
20-Hydroxy-PGE2,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1CC(=O)[C@H](C/C=C\CCCC(=O)O)[C@H]1/C=C/[C@@H](O)CCCCCO	3234.0	Semi standard non polar	33892256
20-Hydroxy-PGE2,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)CCC/C=C\C[C@H]1C(=O)C[C@@H](O)[C@@H]1/C=C/[C@@H](O)CCCCCO	3311.0	Semi standard non polar	33892256
20-Hydroxy-PGE2,1TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=C(C/C=C\CCCC(=O)O)[C@@H](/C=C/[C@@H](O)CCCCCO)[C@H](O)C1	3299.5	Semi standard non polar	33892256
20-Hydroxy-PGE2,1TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=C[C@@H](O)[C@H](/C=C/[C@@H](O)CCCCCO)[C@H]1C/C=C\CCCC(=O)O	3198.6	Semi standard non polar	33892256
20-Hydroxy-PGE2,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCCC[C@@H](/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3594.4	Semi standard non polar	33892256
20-Hydroxy-PGE2,2TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC(=O)CCC/C=C\C[C@H]1C(=O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1/C=C/[C@@H](O)CCCCCO	3429.0	Semi standard non polar	33892256
20-Hydroxy-PGE2,2TBDMS,isomer #11	CC(C)(C)[Si](C)(C)OC1=C(C/C=C\CCCC(=O)O)[C@@H](/C=C/[C@@H](O)CCCCCO)[C@H](O[Si](C)(C)C(C)(C)C)C1	3455.5	Semi standard non polar	33892256
20-Hydroxy-PGE2,2TBDMS,isomer #12	CC(C)(C)[Si](C)(C)OC1=C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](/C=C/[C@@H](O)CCCCCO)[C@H]1C/C=C\CCCC(=O)O	3432.0	Semi standard non polar	33892256
20-Hydroxy-PGE2,2TBDMS,isomer #13	CC(C)(C)[Si](C)(C)OC(=O)CCC/C=C\CC1=C(O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@@H]1/C=C/[C@@H](O)CCCCCO	3509.0	Semi standard non polar	33892256
20-Hydroxy-PGE2,2TBDMS,isomer #14	CC(C)(C)[Si](C)(C)OC(=O)CCC/C=C\C[C@H]1C(O[Si](C)(C)C(C)(C)C)=C[C@@H](O)[C@@H]1/C=C/[C@@H](O)CCCCCO	3432.3	Semi standard non polar	33892256
20-Hydroxy-PGE2,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)O	3438.1	Semi standard non polar	33892256
20-Hydroxy-PGE2,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCCCCC[C@H](O)/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	3541.4	Semi standard non polar	33892256
20-Hydroxy-PGE2,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OCCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C(C)(C)C)C[C@H]1O	3530.5	Semi standard non polar	33892256
20-Hydroxy-PGE2,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OCCCCC[C@H](O)/C=C/[C@H]1[C@H](O)C=C(O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O	3421.4	Semi standard non polar	33892256
20-Hydroxy-PGE2,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)O)CCCCCO	3431.7	Semi standard non polar	33892256
20-Hydroxy-PGE2,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC(=O)CCC/C=C\C[C@H]1C(=O)C[C@@H](O)[C@@H]1/C=C/[C@H](CCCCCO)O[Si](C)(C)C(C)(C)C	3534.7	Semi standard non polar	33892256
20-Hydroxy-PGE2,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC1=C(C/C=C\CCCC(=O)O)[C@@H](/C=C/[C@H](CCCCCO)O[Si](C)(C)C(C)(C)C)[C@H](O)C1	3528.2	Semi standard non polar	33892256
20-Hydroxy-PGE2,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1=C[C@@H](O)[C@H](/C=C/[C@H](CCCCCO)O[Si](C)(C)C(C)(C)C)[C@H]1C/C=C\CCCC(=O)O	3415.3	Semi standard non polar	33892256
20-Hydroxy-PGE2,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3674.1	Semi standard non polar	33892256
20-Hydroxy-PGE2,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC(=O)CCC/C=C\C[C@H]1C(=O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1/C=C/[C@H](CCCCCO)O[Si](C)(C)C(C)(C)C	3647.4	Semi standard non polar	33892256
20-Hydroxy-PGE2,3TBDMS,isomer #11	CC(C)(C)[Si](C)(C)OC1=C(C/C=C\CCCC(=O)O)[C@@H](/C=C/[C@H](CCCCCO)O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C1	3652.6	Semi standard non polar	33892256
20-Hydroxy-PGE2,3TBDMS,isomer #12	CC(C)(C)[Si](C)(C)OC1=C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](/C=C/[C@H](CCCCCO)O[Si](C)(C)C(C)(C)C)[C@H]1C/C=C\CCCC(=O)O	3643.7	Semi standard non polar	33892256
20-Hydroxy-PGE2,3TBDMS,isomer #13	CC(C)(C)[Si](C)(C)OC(=O)CCC/C=C\CC1=C(O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@@H]1/C=C/[C@H](CCCCCO)O[Si](C)(C)C(C)(C)C	3733.6	Semi standard non polar	33892256
20-Hydroxy-PGE2,3TBDMS,isomer #14	CC(C)(C)[Si](C)(C)OC(=O)CCC/C=C\C[C@H]1C(O[Si](C)(C)C(C)(C)C)=C[C@@H](O)[C@@H]1/C=C/[C@H](CCCCCO)O[Si](C)(C)C(C)(C)C	3660.4	Semi standard non polar	33892256
20-Hydroxy-PGE2,3TBDMS,isomer #15	CC(C)(C)[Si](C)(C)OC(=O)CCC/C=C\CC1=C(O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1/C=C/[C@@H](O)CCCCCO	3658.7	Semi standard non polar	33892256
20-Hydroxy-PGE2,3TBDMS,isomer #16	CC(C)(C)[Si](C)(C)OC(=O)CCC/C=C\C[C@H]1C(O[Si](C)(C)C(C)(C)C)=C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1/C=C/[C@@H](O)CCCCCO	3647.9	Semi standard non polar	33892256
20-Hydroxy-PGE2,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCCCCC[C@@H](/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3773.5	Semi standard non polar	33892256
20-Hydroxy-PGE2,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C(C)(C)C)C[C@H]1O)O[Si](C)(C)C(C)(C)C	3742.0	Semi standard non polar	33892256
20-Hydroxy-PGE2,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OCCCCC[C@@H](/C=C/[C@H]1[C@H](O)C=C(O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3659.7	Semi standard non polar	33892256
20-Hydroxy-PGE2,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OCCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	3644.7	Semi standard non polar	33892256
20-Hydroxy-PGE2,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OCCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C(C)(C)C)C[C@H]1O[Si](C)(C)C(C)(C)C	3652.6	Semi standard non polar	33892256
20-Hydroxy-PGE2,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OCCCCC[C@H](O)/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]1C/C=C\CCCC(=O)O	3640.1	Semi standard non polar	33892256
20-Hydroxy-PGE2,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OCCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@H]1O	3727.3	Semi standard non polar	33892256
20-Hydroxy-PGE2,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OCCCCC[C@H](O)/C=C/[C@H]1[C@H](O)C=C(O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	3658.4	Semi standard non polar	33892256
20-Hydroxy-PGE2,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3853.8	Semi standard non polar	33892256
20-Hydroxy-PGE2,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=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	3867.9	Semi standard non polar	33892256
20-Hydroxy-PGE2,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCCCCC[C@@H](/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]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3862.1	Semi standard non polar	33892256
20-Hydroxy-PGE2,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OCCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@H]1O)O[Si](C)(C)C(C)(C)C	3932.7	Semi standard non polar	33892256
20-Hydroxy-PGE2,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OCCCCC[C@@H](/C=C/[C@H]1[C@H](O)C=C(O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3867.9	Semi standard non polar	33892256
20-Hydroxy-PGE2,4TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OCCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@H]1O[Si](C)(C)C(C)(C)C	3859.9	Semi standard non polar	33892256
20-Hydroxy-PGE2,4TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OCCCCC[C@H](O)/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]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	3860.4	Semi standard non polar	33892256
20-Hydroxy-PGE2,4TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC(=O)CCC/C=C\CC1=C(O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1/C=C/[C@H](CCCCCO)O[Si](C)(C)C(C)(C)C	3858.9	Semi standard non polar	33892256
20-Hydroxy-PGE2,4TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC(=O)CCC/C=C\C[C@H]1C(O[Si](C)(C)C(C)(C)C)=C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1/C=C/[C@H](CCCCCO)O[Si](C)(C)C(C)(C)C	3849.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 20-Hydroxy-PGE2 GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udv-2496000000-99122637177145628ab2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 20-Hydroxy-PGE2 GC-MS (4 TMS) - 70eV, Positive	splash10-0006-9300368000-b5e56740df85f5d1a0a1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 20-Hydroxy-PGE2 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 - 20-Hydroxy-PGE2 10V, Positive-QTOF	splash10-0f89-0009000000-ebd1464d44ae0ca6b6a9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-Hydroxy-PGE2 20V, Positive-QTOF	splash10-001i-0149000000-230b542bf2b718260276	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-Hydroxy-PGE2 40V, Positive-QTOF	splash10-000i-9531000000-fe0172c7250e86fb8008	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-Hydroxy-PGE2 10V, Negative-QTOF	splash10-014j-0009000000-de1b715838573884563e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-Hydroxy-PGE2 20V, Negative-QTOF	splash10-00kb-0019000000-173f7be02a65564b8220	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-Hydroxy-PGE2 40V, Negative-QTOF	splash10-0a4i-9443000000-589d4f940035f349cf6b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-Hydroxy-PGE2 10V, Positive-QTOF	splash10-001i-0009000000-ab61e9dbf0bdcec01a2b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-Hydroxy-PGE2 20V, Positive-QTOF	splash10-001r-2498000000-dd316fed2942370b1a27	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-Hydroxy-PGE2 40V, Positive-QTOF	splash10-000i-5900000000-a1dd05387d766559f669	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-Hydroxy-PGE2 10V, Negative-QTOF	splash10-00l2-0009000000-34934b7cf26c41e47d90	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-Hydroxy-PGE2 20V, Negative-QTOF	splash10-001j-0049000000-440e860b86a5284b8bcc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-Hydroxy-PGE2 40V, Negative-QTOF	splash10-053r-8973000000-deffc6d4dd2cd22e8a50	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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

FDB023129

KNApSAcK ID

Not Available

Chemspider ID

4446161

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

3814

PubChem Compound

5283034

PDB ID

Not Available

ChEBI ID

137370

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

Oliw EH, Fahlstadius P, Hamberg M: Biosynthesis of 19-hydroxy and 20-hydroxy E prostaglandins in seminal fluids. Adv Prostaglandin Thromboxane Leukot Res. 1987;17A:39-43. [PubMed:2959084 ]
Oliw EH, Johnsen O: Rapid and slow hydroxylators of seminal E prostaglandins. Biochim Biophys Acta. 1988 Nov 25;963(2):295-301. [PubMed:3196735 ]
Harizi H, Gualde N: Pivotal role of PGE2 and IL-10 in the cross-regulation of dendritic cell-derived inflammatory mediators. Cell Mol Immunol. 2006 Aug;3(4):271-7. [PubMed:16978535 ]

Showing metabocard for 20-Hydroxy-PGE2 (HMDB0003247)

MOL for HMDB0003247 (20-Hydroxy-PGE2)

3D MOL for HMDB0003247 (20-Hydroxy-PGE2)

3D SDF for HMDB0003247 (20-Hydroxy-PGE2)

3D-SDF for HMDB0003247 (20-Hydroxy-PGE2)

PDB for HMDB0003247 (20-Hydroxy-PGE2)

3D PDB for HMDB0003247 (20-Hydroxy-PGE2)

SMILES for HMDB0003247 (20-Hydroxy-PGE2)

INCHI for HMDB0003247 (20-Hydroxy-PGE2)

Structure for HMDB0003247 (20-Hydroxy-PGE2)

3D Structure for HMDB0003247 (20-Hydroxy-PGE2)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra