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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 15:12:02 UTC

Update Date

2022-03-07 02:49:16 UTC

HMDB ID

HMDB0002664

Secondary Accession Numbers

HMDB02664

Metabolite Identification

Common Name

Prostaglandin E3

Description

Prostaglandin E3 is from the cyclooxygenase metabolism of eicosapentaenoic acid.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

HMDB0002664
     RDKit          3D
Prostaglandin E3
 55 55  0  0  0  0  0  0  0  0999 V2000
   -7.8550    1.3627    1.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0656    0.6498    0.2165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7784   -0.7449    0.5507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5657   -1.2232    0.6647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3539   -0.4608    0.4824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4759   -1.0184   -0.6582 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1556   -2.3381   -0.3007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2592   -0.1574   -0.6608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0500   -0.6425   -0.8237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2198    0.1148   -0.8437 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0933    1.5652   -0.4690 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1547    2.3255   -0.9660 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0375    1.5963    1.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4540    0.2397    1.4750 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3482   -0.2711    2.5738 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0527   -0.4302    0.2959 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5116   -0.0092    0.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1713   -0.4463   -0.9877 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2144   -1.2250   -1.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8954   -1.7908    0.1385 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3561   -1.3033    0.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3047    0.1981    0.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6389    0.8159    0.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6884    0.1406    0.1549 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7424    2.1828    0.2504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3358    2.2462    0.7928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2405    1.6993    2.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6105    0.6644    1.6699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8053    0.6005   -0.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2370    1.2356   -0.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6692   -1.4112    0.7104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4778   -2.2853    0.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4730    0.6008    0.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6917   -0.5607    1.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0087   -1.0308   -1.6088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6112   -3.0019   -0.8837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3994    0.9008   -0.5187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0289   -1.7463   -0.9565 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7490    0.0275   -1.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8092    1.9720   -0.9644 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8997    3.2327   -1.2140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6264    2.4055    1.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0430    1.7438    1.3074 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0341   -1.5304    0.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9757   -0.4353    1.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5879    1.1047    0.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7761   -0.1035   -1.9653 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6492   -1.5037   -2.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4985   -1.5138    1.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9946   -2.9033    0.0577 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8132   -1.6846    1.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8785   -1.6751   -0.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7979    0.4746    1.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6583    0.5958   -0.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1781    2.7512   -0.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 16 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  6
  7 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  6
 11 40  1  6
 12 41  1  0
 13 42  1  0
 13 43  1  0
 16 44  1  1
 17 45  1  0
 17 46  1  0
 18 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 25 55  1  0
M  END


  Mrv0541 02231219342D          

 25 25  0  0  1  0            999 V2000
   45.3710  -28.2135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   46.8232  -30.9185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.4373  -28.2848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.9957  -29.6438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   44.4736  -32.6255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   46.0855  -28.6260    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   41.5650  -30.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3935  -29.3467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.8000  -28.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3497  -30.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   48.2290  -27.3885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.9189  -30.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   48.9435  -26.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.0385  -31.1735    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   45.3710  -30.6886    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   44.7036  -31.1735    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   45.7835  -31.9581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6089  -29.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.8000  -27.3885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.5145  -26.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.5212  -31.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.3059  -31.4706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.0855  -29.4510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.3710  -29.8635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.9585  -31.9581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  1  0  0  0
 14  2  1  6  0  0  0
  3 18  1  0  0  0  0
  4 18  2  0  0  0  0
  5 25  2  0  0  0  0
  6  9  1  0  0  0  0
  6 23  1  0  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8 18  1  0  0  0  0
  9 19  1  0  0  0  0
 10 21  1  0  0  0  0
 11 13  1  0  0  0  0
 11 20  1  0  0  0  0
 16 12  1  6  0  0  0
 12 22  1  0  0  0  0
 14 15  1  0  0  0  0
 14 17  1  0  0  0  0
 15 16  1  0  0  0  0
 15 24  1  1  0  0  0
 16 25  1  0  0  0  0
 17 25  1  0  0  0  0
 19 20  2  0  0  0  0
 21 22  2  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002664

> <DATABASE_NAME>
hmdb

> <SMILES>
CC\C=C/C[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/C20H30O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h3-4,6-7,12-13,15-17,19,21,23H,2,5,8-11,14H2,1H3,(H,24,25)/b6-3-,7-4-,13-12+/t15-,16+,17+,19+/m0/s1

> <INCHI_KEY>
CBOMORHDRONZRN-QLOYDKTKSA-N

> <FORMULA>
C20H30O5

> <MOLECULAR_WEIGHT>
350.4492

> <EXACT_MASS>
350.20932407

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
39.43553882304386

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.88

> <JCHEM_LOGP>
2.8633484803333324

> <ALOGPS_LOGS>
-3.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.678907861244504

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.303359481832455

> <JCHEM_PKA_STRONGEST_BASIC>
-1.665276589103597

> <JCHEM_POLAR_SURFACE_AREA>
94.82999999999998

> <JCHEM_REFRACTIVITY>
100.5517

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.78e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-prostaglandin E3

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002664
     RDKit          3D
Prostaglandin E3
 55 55  0  0  0  0  0  0  0  0999 V2000
   -7.8550    1.3627    1.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0656    0.6498    0.2165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7784   -0.7449    0.5507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5657   -1.2232    0.6647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3539   -0.4608    0.4824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4759   -1.0184   -0.6582 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1556   -2.3381   -0.3007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2592   -0.1574   -0.6608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0500   -0.6425   -0.8237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2198    0.1148   -0.8437 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0933    1.5652   -0.4690 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1547    2.3255   -0.9660 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0375    1.5963    1.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4540    0.2397    1.4750 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3482   -0.2711    2.5738 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0527   -0.4302    0.2959 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5116   -0.0092    0.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1713   -0.4463   -0.9877 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2144   -1.2250   -1.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8954   -1.7908    0.1385 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3561   -1.3033    0.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3047    0.1981    0.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6389    0.8159    0.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6884    0.1406    0.1549 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7424    2.1828    0.2504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3358    2.2462    0.7928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2405    1.6993    2.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6105    0.6644    1.6699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8053    0.6005   -0.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2370    1.2356   -0.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6692   -1.4112    0.7104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4778   -2.2853    0.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4730    0.6008    0.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6917   -0.5607    1.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0087   -1.0308   -1.6088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6112   -3.0019   -0.8837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3994    0.9008   -0.5187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0289   -1.7463   -0.9565 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7490    0.0275   -1.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8092    1.9720   -0.9644 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8997    3.2327   -1.2140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6264    2.4055    1.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0430    1.7438    1.3074 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0341   -1.5304    0.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9757   -0.4353    1.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5879    1.1047    0.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7761   -0.1035   -1.9653 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6492   -1.5037   -2.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4985   -1.5138    1.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9946   -2.9033    0.0577 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8132   -1.6846    1.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8785   -1.6751   -0.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7979    0.4746    1.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6583    0.5958   -0.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1781    2.7512   -0.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 16 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  6
  7 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  6
 11 40  1  6
 12 41  1  0
 13 42  1  0
 13 43  1  0
 16 44  1  1
 17 45  1  0
 17 46  1  0
 18 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 25 55  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      84.693 -52.665   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      87.403 -57.715   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      75.483 -52.798   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      74.659 -55.335   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      83.017 -60.901   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      86.026 -53.435   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      77.588 -56.287   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      77.268 -54.781   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      87.360 -52.665   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      79.053 -56.763   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      90.027 -51.125   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      81.982 -57.715   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      91.361 -50.355   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      85.939 -58.191   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      84.693 -57.285   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      83.447 -58.191   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      85.463 -59.655   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      75.803 -54.305   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      87.360 -51.125   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      88.694 -50.355   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      79.373 -58.269   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      80.838 -58.745   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      86.026 -54.975   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      84.693 -55.745   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      83.923 -59.655   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2   14                                                            
CONECT    3   18                                                            
CONECT    4   18                                                            
CONECT    5   25                                                            
CONECT    6    1    9   23                                                  
CONECT    7    8   10                                                       
CONECT    8    7   18                                                       
CONECT    9    6   19                                                       
CONECT   10    7   21                                                       
CONECT   11   13   20                                                       
CONECT   12   16   22                                                       
CONECT   13   11                                                            
CONECT   14    2   15   17                                                  
CONECT   15   14   16   24                                                  
CONECT   16   12   15   25                                                  
CONECT   17   14   25                                                       
CONECT   18    3    4    8                                                  
CONECT   19    9   20                                                       
CONECT   20   11   19                                                       
CONECT   21   10   22                                                       
CONECT   22   12   21                                                       
CONECT   23    6   24                                                       
CONECT   24   15   23                                                       
CONECT   25    5   16   17                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

COMPND    HMDB0002664
HETATM    1  C1  UNL     1      -7.855   1.363   1.299  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.066   0.650   0.217  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.778  -0.745   0.551  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.566  -1.223   0.665  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.354  -0.461   0.482  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.476  -1.018  -0.658  1.00  0.00           C  
HETATM    7  O1  UNL     1      -3.156  -2.338  -0.301  1.00  0.00           O  
HETATM    8  C7  UNL     1      -2.259  -0.157  -0.661  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.050  -0.642  -0.824  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.220   0.115  -0.844  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.093   1.565  -0.469  1.00  0.00           C  
HETATM   12  O2  UNL     1       1.155   2.326  -0.966  1.00  0.00           O  
HETATM   13  C11 UNL     1       0.038   1.596   1.035  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.454   0.240   1.475  1.00  0.00           C  
HETATM   15  O3  UNL     1       0.348  -0.271   2.574  1.00  0.00           O  
HETATM   16  C13 UNL     1       1.053  -0.430   0.296  1.00  0.00           C  
HETATM   17  C14 UNL     1       2.512  -0.009   0.221  1.00  0.00           C  
HETATM   18  C15 UNL     1       3.171  -0.446  -0.988  1.00  0.00           C  
HETATM   19  C16 UNL     1       4.214  -1.225  -1.044  1.00  0.00           C  
HETATM   20  C17 UNL     1       4.895  -1.791   0.138  1.00  0.00           C  
HETATM   21  C18 UNL     1       6.356  -1.303   0.135  1.00  0.00           C  
HETATM   22  C19 UNL     1       6.305   0.198   0.195  1.00  0.00           C  
HETATM   23  C20 UNL     1       7.639   0.816   0.198  1.00  0.00           C  
HETATM   24  O4  UNL     1       8.688   0.141   0.155  1.00  0.00           O  
HETATM   25  O5  UNL     1       7.742   2.183   0.250  1.00  0.00           O  
HETATM   26  H1  UNL     1      -8.336   2.246   0.793  1.00  0.00           H  
HETATM   27  H2  UNL     1      -7.240   1.699   2.135  1.00  0.00           H  
HETATM   28  H3  UNL     1      -8.611   0.664   1.670  1.00  0.00           H  
HETATM   29  H4  UNL     1      -7.805   0.600  -0.655  1.00  0.00           H  
HETATM   30  H5  UNL     1      -6.237   1.236  -0.191  1.00  0.00           H  
HETATM   31  H6  UNL     1      -7.669  -1.411   0.710  1.00  0.00           H  
HETATM   32  H7  UNL     1      -5.478  -2.285   0.918  1.00  0.00           H  
HETATM   33  H8  UNL     1      -4.473   0.601   0.222  1.00  0.00           H  
HETATM   34  H9  UNL     1      -3.692  -0.561   1.404  1.00  0.00           H  
HETATM   35  H10 UNL     1      -4.009  -1.031  -1.609  1.00  0.00           H  
HETATM   36  H11 UNL     1      -3.611  -3.002  -0.884  1.00  0.00           H  
HETATM   37  H12 UNL     1      -2.399   0.901  -0.519  1.00  0.00           H  
HETATM   38  H13 UNL     1      -1.029  -1.746  -0.956  1.00  0.00           H  
HETATM   39  H14 UNL     1       0.749   0.027  -1.819  1.00  0.00           H  
HETATM   40  H15 UNL     1      -0.809   1.972  -0.964  1.00  0.00           H  
HETATM   41  H16 UNL     1       0.900   3.233  -1.214  1.00  0.00           H  
HETATM   42  H17 UNL     1       0.626   2.405   1.477  1.00  0.00           H  
HETATM   43  H18 UNL     1      -1.043   1.744   1.307  1.00  0.00           H  
HETATM   44  H19 UNL     1       1.034  -1.530   0.356  1.00  0.00           H  
HETATM   45  H20 UNL     1       2.976  -0.435   1.122  1.00  0.00           H  
HETATM   46  H21 UNL     1       2.588   1.105   0.376  1.00  0.00           H  
HETATM   47  H22 UNL     1       2.776  -0.103  -1.965  1.00  0.00           H  
HETATM   48  H23 UNL     1       4.649  -1.504  -2.045  1.00  0.00           H  
HETATM   49  H24 UNL     1       4.498  -1.514   1.116  1.00  0.00           H  
HETATM   50  H25 UNL     1       4.995  -2.903   0.058  1.00  0.00           H  
HETATM   51  H26 UNL     1       6.813  -1.685   1.071  1.00  0.00           H  
HETATM   52  H27 UNL     1       6.878  -1.675  -0.760  1.00  0.00           H  
HETATM   53  H28 UNL     1       5.798   0.475   1.138  1.00  0.00           H  
HETATM   54  H29 UNL     1       5.658   0.596  -0.631  1.00  0.00           H  
HETATM   55  H30 UNL     1       8.178   2.751  -0.489  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4    4   31
CONECT    4    5   32
CONECT    5    6   33   34
CONECT    6    7    8   35
CONECT    7   36
CONECT    8    9    9   37
CONECT    9   10   38
CONECT   10   11   16   39
CONECT   11   12   13   40
CONECT   12   41
CONECT   13   14   42   43
CONECT   14   15   15   16
CONECT   16   17   44
CONECT   17   18   45   46
CONECT   18   19   19   47
CONECT   19   20   48
CONECT   20   21   49   50
CONECT   21   22   51   52
CONECT   22   23   53   54
CONECT   23   24   24   25
CONECT   25   55
END

HMDB0002664
     RDKit          3D
Prostaglandin E3
 55 55  0  0  0  0  0  0  0  0999 V2000
   -7.8550    1.3627    1.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0656    0.6498    0.2165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7784   -0.7449    0.5507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5657   -1.2232    0.6647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3539   -0.4608    0.4824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4759   -1.0184   -0.6582 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1556   -2.3381   -0.3007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2592   -0.1574   -0.6608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0500   -0.6425   -0.8237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2198    0.1148   -0.8437 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0933    1.5652   -0.4690 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1547    2.3255   -0.9660 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0375    1.5963    1.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4540    0.2397    1.4750 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3482   -0.2711    2.5738 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0527   -0.4302    0.2959 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5116   -0.0092    0.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1713   -0.4463   -0.9877 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2144   -1.2250   -1.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8954   -1.7908    0.1385 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3561   -1.3033    0.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3047    0.1981    0.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6389    0.8159    0.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6884    0.1406    0.1549 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7424    2.1828    0.2504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3358    2.2462    0.7928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2405    1.6993    2.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6105    0.6644    1.6699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8053    0.6005   -0.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2370    1.2356   -0.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6692   -1.4112    0.7104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4778   -2.2853    0.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4730    0.6008    0.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6917   -0.5607    1.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0087   -1.0308   -1.6088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6112   -3.0019   -0.8837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3994    0.9008   -0.5187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0289   -1.7463   -0.9565 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7490    0.0275   -1.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8092    1.9720   -0.9644 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8997    3.2327   -1.2140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6264    2.4055    1.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0430    1.7438    1.3074 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0341   -1.5304    0.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9757   -0.4353    1.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5879    1.1047    0.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7761   -0.1035   -1.9653 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6492   -1.5037   -2.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4985   -1.5138    1.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9946   -2.9033    0.0577 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8132   -1.6846    1.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8785   -1.6751   -0.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7979    0.4746    1.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6583    0.5958   -0.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1781    2.7512   -0.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 16 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  6
  7 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  6
 11 40  1  6
 12 41  1  0
 13 42  1  0
 13 43  1  0
 16 44  1  1
 17 45  1  0
 17 46  1  0
 18 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 25 55  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5Z,11alpha,13E,15S,17Z)-11,15-Dihydroxy-9-oxoprosta-5,13,17-trien-1-Oic acid	ChEBI
9-oxo-11R,15S-Dihydroxy-5Z,13E,17Z-prostatrienoic acid	ChEBI
PGE3	ChEBI
(5Z,11a,13E,15S,17Z)-11,15-Dihydroxy-9-oxoprosta-5,13,17-trien-1-Oate	Generator
(5Z,11a,13E,15S,17Z)-11,15-Dihydroxy-9-oxoprosta-5,13,17-trien-1-Oic acid	Generator
(5Z,11alpha,13E,15S,17Z)-11,15-Dihydroxy-9-oxoprosta-5,13,17-trien-1-Oate	Generator
(5Z,11Α,13E,15S,17Z)-11,15-dihydroxy-9-oxoprosta-5,13,17-trien-1-Oate	Generator
(5Z,11Α,13E,15S,17Z)-11,15-dihydroxy-9-oxoprosta-5,13,17-trien-1-Oic acid	Generator
9-oxo-11R,15S-Dihydroxy-5Z,13E,17Z-prostatrienoate	Generator
(-)-Prostaglandin e3	HMDB
7-[3-Hydroxy-2-(3-hydroxy-1,5-octadienyl)-5-oxocyclopentyl]-5-heptenoate	HMDB
7-[3-Hydroxy-2-(3-hydroxy-1,5-octadienyl)-5-oxocyclopentyl]-5-heptenoic acid	HMDB
7-[3-Hydroxy-2-(3-hydroxy-1,5-octadienyl)-5-oxocyclopentyl]-5-heptenoic acid stereoisomer	HMDB
delta(17)-PGE1	HMDB
delta(17)-Prostaglandin e1	HMDB
Prostaglandin e3	MeSH

Chemical Formula

C₂₀H₃₀O₅

Average Molecular Weight

350.4492

Monoisotopic Molecular Weight

350.20932407

IUPAC Name

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

Traditional Name

(-)-prostaglandin E3

CAS Registry Number

802-31-3

SMILES

CC\C=C/C[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/C20H30O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h3-4,6-7,12-13,15-17,19,21,23H,2,5,8-11,14H2,1H3,(H,24,25)/b6-3-,7-4-,13-12+/t15-,16+,17+,19+/m0/s1

InChI Key

CBOMORHDRONZRN-QLOYDKTKSA-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
Ketone
Cyclic ketone
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

prostaglandins E (CHEBI:28031 )
Prostaglandins (C06439 )
Prostaglandins (LMFA03010135 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21359215)

Cellular substructure

Extracellular (HMDB: HMDB0002664)
Membrane (HMDB: HMDB0002664)

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

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.088 g/L	ALOGPS
logP	2.88	ALOGPS
logP	2.86	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	4.3	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	100.55 m³·mol⁻¹	ChemAxon
Polarizability	39.44 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]+	185.814	31661259
DarkChem	[M-H]-	182.862	31661259
DeepCCS	[M+H]+	196.012	30932474
DeepCCS	[M-H]-	193.616	30932474
DeepCCS	[M-2H]-	227.528	30932474
DeepCCS	[M+Na]+	202.321	30932474
AllCCS	[M+H]+	191.7	32859911
AllCCS	[M+H-H2O]+	189.0	32859911
AllCCS	[M+NH4]+	194.3	32859911
AllCCS	[M+Na]+	195.0	32859911
AllCCS	[M-H]-	189.9	32859911
AllCCS	[M+Na-2H]-	191.3	32859911
AllCCS	[M+HCOO]-	192.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Prostaglandin E3	CC\C=C/C[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O	4466.6	Standard polar	33892256
Prostaglandin E3	CC\C=C/C[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O	2675.4	Standard non polar	33892256
Prostaglandin E3	CC\C=C/C[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O	2898.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Prostaglandin E3,1TMS,isomer #1	CC/C=C\C[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	2887.8	Semi standard non polar	33892256
Prostaglandin E3,1TMS,isomer #2	CC/C=C\C[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	2805.2	Semi standard non polar	33892256
Prostaglandin E3,1TMS,isomer #3	CC/C=C\C[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	2796.9	Semi standard non polar	33892256
Prostaglandin E3,1TMS,isomer #4	CC/C=C\C[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C)C[C@H]1O	2813.9	Semi standard non polar	33892256
Prostaglandin E3,1TMS,isomer #5	CC/C=C\C[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	2749.9	Semi standard non polar	33892256
Prostaglandin E3,2TMS,isomer #1	CC/C=C\C[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	2762.8	Semi standard non polar	33892256
Prostaglandin E3,2TMS,isomer #2	CC/C=C\C[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	2799.7	Semi standard non polar	33892256
Prostaglandin E3,2TMS,isomer #3	CC/C=C\C[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	2851.9	Semi standard non polar	33892256
Prostaglandin E3,2TMS,isomer #4	CC/C=C\C[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	2748.9	Semi standard non polar	33892256
Prostaglandin E3,2TMS,isomer #5	CC/C=C\C[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	2754.6	Semi standard non polar	33892256
Prostaglandin E3,2TMS,isomer #6	CC/C=C\C[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	2803.1	Semi standard non polar	33892256
Prostaglandin E3,2TMS,isomer #7	CC/C=C\C[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	2762.5	Semi standard non polar	33892256
Prostaglandin E3,2TMS,isomer #8	CC/C=C\C[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	2782.3	Semi standard non polar	33892256
Prostaglandin E3,2TMS,isomer #9	CC/C=C\C[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	2729.9	Semi standard non polar	33892256
Prostaglandin E3,3TMS,isomer #1	CC/C=C\C[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	2739.8	Semi standard non polar	33892256
Prostaglandin E3,3TMS,isomer #2	CC/C=C\C[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	2800.7	Semi standard non polar	33892256
Prostaglandin E3,3TMS,isomer #3	CC/C=C\C[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	2754.1	Semi standard non polar	33892256
Prostaglandin E3,3TMS,isomer #4	CC/C=C\C[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	2807.7	Semi standard non polar	33892256
Prostaglandin E3,3TMS,isomer #5	CC/C=C\C[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	2738.2	Semi standard non polar	33892256
Prostaglandin E3,3TMS,isomer #6	CC/C=C\C[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	2780.1	Semi standard non polar	33892256
Prostaglandin E3,3TMS,isomer #7	CC/C=C\C[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	2745.2	Semi standard non polar	33892256
Prostaglandin E3,4TMS,isomer #1	CC/C=C\C[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	2791.2	Semi standard non polar	33892256
Prostaglandin E3,4TMS,isomer #1	CC/C=C\C[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	2851.8	Standard non polar	33892256
Prostaglandin E3,4TMS,isomer #1	CC/C=C\C[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	2819.7	Standard polar	33892256
Prostaglandin E3,4TMS,isomer #2	CC/C=C\C[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	2772.4	Semi standard non polar	33892256
Prostaglandin E3,4TMS,isomer #2	CC/C=C\C[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	2678.6	Standard non polar	33892256
Prostaglandin E3,4TMS,isomer #2	CC/C=C\C[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	2876.7	Standard polar	33892256
Prostaglandin E3,1TBDMS,isomer #1	CC/C=C\C[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	3127.1	Semi standard non polar	33892256
Prostaglandin E3,1TBDMS,isomer #2	CC/C=C\C[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	3013.3	Semi standard non polar	33892256
Prostaglandin E3,1TBDMS,isomer #3	CC/C=C\C[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	3048.5	Semi standard non polar	33892256
Prostaglandin E3,1TBDMS,isomer #4	CC/C=C\C[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	3080.2	Semi standard non polar	33892256
Prostaglandin E3,1TBDMS,isomer #5	CC/C=C\C[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	2982.9	Semi standard non polar	33892256
Prostaglandin E3,2TBDMS,isomer #1	CC/C=C\C[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	3245.1	Semi standard non polar	33892256
Prostaglandin E3,2TBDMS,isomer #2	CC/C=C\C[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	3296.4	Semi standard non polar	33892256
Prostaglandin E3,2TBDMS,isomer #3	CC/C=C\C[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	3308.1	Semi standard non polar	33892256
Prostaglandin E3,2TBDMS,isomer #4	CC/C=C\C[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	3226.5	Semi standard non polar	33892256
Prostaglandin E3,2TBDMS,isomer #5	CC/C=C\C[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	3230.0	Semi standard non polar	33892256
Prostaglandin E3,2TBDMS,isomer #6	CC/C=C\C[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	3253.6	Semi standard non polar	33892256
Prostaglandin E3,2TBDMS,isomer #7	CC/C=C\C[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	3225.2	Semi standard non polar	33892256
Prostaglandin E3,2TBDMS,isomer #8	CC/C=C\C[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	3264.3	Semi standard non polar	33892256
Prostaglandin E3,2TBDMS,isomer #9	CC/C=C\C[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	3208.5	Semi standard non polar	33892256
Prostaglandin E3,3TBDMS,isomer #1	CC/C=C\C[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	3461.0	Semi standard non polar	33892256
Prostaglandin E3,3TBDMS,isomer #2	CC/C=C\C[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	3464.8	Semi standard non polar	33892256
Prostaglandin E3,3TBDMS,isomer #3	CC/C=C\C[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	3461.9	Semi standard non polar	33892256
Prostaglandin E3,3TBDMS,isomer #4	CC/C=C\C[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	3507.5	Semi standard non polar	33892256
Prostaglandin E3,3TBDMS,isomer #5	CC/C=C\C[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	3448.8	Semi standard non polar	33892256
Prostaglandin E3,3TBDMS,isomer #6	CC/C=C\C[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	3464.2	Semi standard non polar	33892256
Prostaglandin E3,3TBDMS,isomer #7	CC/C=C\C[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	3457.8	Semi standard non polar	33892256
Prostaglandin E3,4TBDMS,isomer #1	CC/C=C\C[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[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3640.1	Semi standard non polar	33892256
Prostaglandin E3,4TBDMS,isomer #1	CC/C=C\C[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[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3485.5	Standard non polar	33892256
Prostaglandin E3,4TBDMS,isomer #1	CC/C=C\C[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[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3101.0	Standard polar	33892256
Prostaglandin E3,4TBDMS,isomer #2	CC/C=C\C[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[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3644.6	Semi standard non polar	33892256
Prostaglandin E3,4TBDMS,isomer #2	CC/C=C\C[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[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3213.0	Standard non polar	33892256
Prostaglandin E3,4TBDMS,isomer #2	CC/C=C\C[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[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3127.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin E3 GC-MS (Non-derivatized) - 70eV, Positive	splash10-0059-7496000000-9210fb4674d794816bc0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin E3 GC-MS (3 TMS) - 70eV, Positive	splash10-0udi-9101680000-a66ceba0ca4003a25001	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin E3 GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin E3 GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin E3 10V, Positive-QTOF	splash10-00lr-0019000000-3a37659687433065f9da	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin E3 20V, Positive-QTOF	splash10-0159-4197000000-5a2017a0bfe4592e8fff	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin E3 40V, Positive-QTOF	splash10-00kr-9220000000-feedd008762c81af1d13	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin E3 10V, Negative-QTOF	splash10-000t-0009000000-50f3213aa3eff0d0faf7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin E3 20V, Negative-QTOF	splash10-001j-2149000000-29aed26fd57d9c5f3bc8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin E3 40V, Negative-QTOF	splash10-0a4i-9431000000-5c1e13cc53c44b8f766d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin E3 10V, Positive-QTOF	splash10-014i-0019000000-5c376e396ab8f47ce7dc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin E3 20V, Positive-QTOF	splash10-014i-4196000000-1567e644caaefea5e0db	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin E3 40V, Positive-QTOF	splash10-014l-9700000000-9dfab3d79c88fcbb1ec7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin E3 10V, Negative-QTOF	splash10-001i-0009000000-87bc754463331ba5961a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin E3 20V, Negative-QTOF	splash10-001i-0096000000-6b6024dbd45dd4f026a1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin E3 40V, Negative-QTOF	splash10-001l-9480000000-a2fb3e9a5f2bfee6385b	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	<0.0001 uM	Adult (>18 years old)	Both	Normal	21359215	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023042

KNApSAcK ID

Not Available

Chemspider ID

4444439

KEGG Compound ID

C06439

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Prostaglandin E3

METLIN ID

3494

PubChem Compound

5280937

PDB ID

Not Available

ChEBI ID

28031

Food Biomarker Ontology

Not Available

VMH ID

HC02213

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Okamoto, Sentaro; Kobayashi, Yuichi; Sato, Fumie. A highly efficient synthesis of natural PGE3 and 5,6-dihydro PGE3 via two-component coupling process. Tetrahedron Letters (1989), 30(33), 4379-82.

Material Safety Data Sheet (MSDS)

Not Available

General References

Kivits GA, Nugteren DH: The urinary excretion of prostaglandins E and their corresponding tetranor metabolites by rats fed a diet rich in eicosapentaenoate. Biochim Biophys Acta. 1988 Feb 4;958(2):289-99. [PubMed:2827784 ]
Fischer S, von Schacky C, Schweer H: Prostaglandins E3 and F3 alpha are excreted in human urine after ingestion of n - 3 polyunsaturated fatty acids. Biochim Biophys Acta. 1988 Dec 16;963(3):501-8. [PubMed:3196747 ]

Showing metabocard for Prostaglandin E3 (HMDB0002664)

MOL for HMDB0002664 (Prostaglandin E3)

3D MOL for HMDB0002664 (Prostaglandin E3)

3D SDF for HMDB0002664 (Prostaglandin E3)

3D-SDF for HMDB0002664 (Prostaglandin E3)

PDB for HMDB0002664 (Prostaglandin E3)

3D PDB for HMDB0002664 (Prostaglandin E3)

SMILES for HMDB0002664 (Prostaglandin E3)

INCHI for HMDB0002664 (Prostaglandin E3)

Structure for HMDB0002664 (Prostaglandin E3)

3D Structure for HMDB0002664 (Prostaglandin E3)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra