NP-MRD: Showing NP-Card for 6-Ketoprostaglandin E1 (NP0087161)

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Record Information

Version

2.0

Created at

2022-05-11 16:41:50 UTC

Updated at

2022-05-11 16:41:50 UTC

NP-MRD ID

NP0087161

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-Ketoprostaglandin E1

Description

6-Ketoprostaglandin E1, also known as 6-keto-pge1, 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. Thus, 6-ketoprostaglandin E1 is considered to be an eicosanoid lipid molecule. A prostaglandin E that is prostaglandin E1 bearing a keto substituent at the 6-position. 6-Ketoprostaglandin E1 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 6-Ketoprostaglandin E1 was first documented in 1980 (PMID: 6258185). In humans, 6-ketoprostaglandin E1 is involved in mefenamic acid action pathway (PMID: 3186779) (PMID: 3075239) (PMID: 3472253) (PMID: 3912001).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv0541 02231219542D          

 26 26  0  0  1  0            999 V2000
   32.8629  -14.9689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.5133  -16.6759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.5171  -16.3280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.4108  -12.2639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1523  -16.4123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5939  -15.0532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.4108  -14.7390    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   30.7433  -15.2239    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   32.0782  -15.2239    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   31.8233  -16.0085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9983  -16.0085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9587  -14.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4108  -13.9139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3456  -15.5210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1252  -13.5014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5609  -15.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1252  -12.6764    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   32.8397  -12.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9478  -15.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8397  -11.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1632  -15.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5543  -11.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5543  -10.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5501  -16.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2687   -9.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7654  -15.8602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  6  0  0  0
  2 11  2  0  0  0  0
  3 14  2  0  0  0  0
 17  4  1  1  0  0  0
  5 26  1  0  0  0  0
  6 26  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 13  1  1  0  0  0
  8 11  1  0  0  0  0
  8 12  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  2  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 16 19  1  0  0  0  0
 17 18  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 24  1  0  0  0  0
 22 23  1  0  0  0  0
 23 25  1  0  0  0  0
 24 26  1  0  0  0  0
M  END

     RDKit          3D

 58 58  0  0  0  0  0  0  0  0999 V2000
    6.8885   -0.8005   -2.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0845   -0.7972   -0.8404 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2982   -2.0755   -0.7141 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4999   -2.2454    0.4984 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4009   -1.3719    0.8726 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5707    0.0655    1.1109 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5105    0.2413    2.1431 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2576    0.5211    1.7621 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0995    0.3761    1.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2003    0.7978    1.7218 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0436    1.5388    3.0367 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0625    0.6198    4.0639 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3003    2.3994    3.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6671    2.6968    1.7229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4658    3.5136    1.3383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8813    1.8123    0.8231 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8012    1.2135   -0.1813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9177    0.4430    0.3744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0577    0.3717    1.5850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9267   -0.2833   -0.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6756   -0.2078   -1.9070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7061   -0.9582   -2.7131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1087   -0.4509   -2.5152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0326   -1.2714   -3.3606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6307   -2.2144   -4.0904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3949   -1.0100   -3.3655 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2282   -1.8374   -2.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7643   -0.1438   -2.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2060   -0.4933   -2.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8617   -0.7161   -0.0324 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4757    0.1152   -0.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7639   -2.3192   -1.6679 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0980   -2.8883   -0.6914 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2485   -2.3333    1.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0772   -3.3126    0.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9407   -1.7971    1.8278 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5228   -1.4864    0.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6702    0.7464    0.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2479   -0.2028    2.9639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2649    0.9644    2.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0875   -0.0782    0.1387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8076   -0.1123    1.8329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7962    2.2387    3.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6759    0.7326    4.7104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0991    3.3656    3.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1030    1.8927    3.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1088    2.3949    0.2796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1770    0.5293   -0.8286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1143    2.0315   -0.8731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9283    0.1123   -0.1792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9057   -1.3492   -0.1322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7311    0.8626   -2.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6980   -0.5768   -2.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7149   -2.0465   -2.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4647   -0.8633   -3.7944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2382    0.5961   -2.8532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4521   -0.5301   -1.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8975   -0.7484   -2.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 26  1  0
 24 25  2  0
 16 10  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  6
  7 39  1  0
  8 40  1  0
  9 41  1  0
 10 42  1  1
 11 43  1  6
 12 44  1  0
 13 45  1  0
 13 46  1  0
 16 47  1  6
 17 48  1  0
 17 49  1  0
 20 50  1  0
 20 51  1  0
 21 52  1  0
 21 53  1  0
 22 54  1  0
 22 55  1  0
 23 56  1  0
 23 57  1  0
 26 58  1  0
M  END

  Mrv0541 02231219542D          

 26 26  0  0  1  0            999 V2000
   32.8629  -14.9689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.5133  -16.6759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.5171  -16.3280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.4108  -12.2639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1523  -16.4123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5939  -15.0532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.4108  -14.7390    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   30.7433  -15.2239    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   32.0782  -15.2239    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   31.8233  -16.0085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9983  -16.0085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9587  -14.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4108  -13.9139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3456  -15.5210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1252  -13.5014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5609  -15.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1252  -12.6764    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   32.8397  -12.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9478  -15.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8397  -11.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1632  -15.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5543  -11.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5543  -10.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5501  -16.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2687   -9.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7654  -15.8602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  6  0  0  0
  2 11  2  0  0  0  0
  3 14  2  0  0  0  0
 17  4  1  1  0  0  0
  5 26  1  0  0  0  0
  6 26  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 13  1  1  0  0  0
  8 11  1  0  0  0  0
  8 12  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  2  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 16 19  1  0  0  0  0
 17 18  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 24  1  0  0  0  0
 22 23  1  0  0  0  0
 23 25  1  0  0  0  0
 24 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0087161

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O6/c1-2-3-4-7-14(21)10-11-16-17(19(24)13-18(16)23)12-15(22)8-5-6-9-20(25)26/h10-11,14,16-18,21,23H,2-9,12-13H2,1H3,(H,25,26)/b11-10+/t14-,16+,17+,18+/m0/s1

> <INCHI_KEY>
ROUDCKODIMKLNO-CTBSXBMHSA-N

> <FORMULA>
C20H32O6

> <MOLECULAR_WEIGHT>
368.4645

> <EXACT_MASS>
368.219888756

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
42.053318836350265

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]-6-oxoheptanoic acid

> <ALOGPS_LOGP>
2.02

> <JCHEM_LOGP>
2.407974068333333

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.660021138791254

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.095565204456448

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6263171149981344

> <JCHEM_POLAR_SURFACE_AREA>
111.9

> <JCHEM_REFRACTIVITY>
98.9599

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.76e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-Keto-PGE1

> <JCHEM_VEBER_RULE>
0

$$$$

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      61.344 -27.942   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      56.958 -31.128   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      55.099 -30.479   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      58.633 -22.893   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      46.951 -30.636   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      47.775 -28.099   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      58.633 -27.513   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      57.387 -28.418   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      59.879 -28.418   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      59.403 -29.883   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      57.863 -29.883   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      55.923 -27.942   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      58.633 -25.973   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      54.778 -28.973   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      59.967 -25.203   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      53.314 -28.497   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      59.967 -23.663   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      61.301 -22.893   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      52.169 -29.527   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      61.301 -21.353   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      50.705 -29.051   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      62.635 -20.583   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      62.635 -19.043   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      49.560 -30.082   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      63.968 -18.273   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      48.095 -29.606   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2   11                                                            
CONECT    3   14                                                            
CONECT    4   17                                                            
CONECT    5   26                                                            
CONECT    6   26                                                            
CONECT    7    8    9   13                                                  
CONECT    8    7   11   12                                                  
CONECT    9    1    7   10                                                  
CONECT   10    9   11                                                       
CONECT   11    2    8   10                                                  
CONECT   12    8   14                                                       
CONECT   13    7   15                                                       
CONECT   14    3   12   16                                                  
CONECT   15   13   17                                                       
CONECT   16   14   19                                                       
CONECT   17    4   15   18                                                  
CONECT   18   17   20                                                       
CONECT   19   16   21                                                       
CONECT   20   18   22                                                       
CONECT   21   19   24                                                       
CONECT   22   20   23                                                       
CONECT   23   22   25                                                       
CONECT   24   21   26                                                       
CONECT   25   23                                                            
CONECT   26    5    6   24                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   52    0
END

View in JSmol

Synonyms

Value	Source
6-Keto-pge1	ChEBI
6-Keto-prostaglandin e1	ChEBI
6-oxo-PGE1	ChEBI
6-Oxoprostaglandin e1	HMDB
6,9-Dioxo-11R,15S-dihydroxy-13E-prostenoate	HMDB
6,9-Dioxo-11R,15S-dihydroxy-13E-prostenoic acid	HMDB
6-Keto pge1	HMDB
6-KPGE1	HMDB
6-oxo-Prostaglandin e1	HMDB

Chemical Formula

C₂₀H₃₂O₆

Average Mass

368.4645 Da

Monoisotopic Mass

368.21989 Da

IUPAC Name

7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]-6-oxoheptanoic acid

Traditional Name

6-Keto-PGE1

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H32O6/c1-2-3-4-7-14(21)10-11-16-17(19(24)13-18(16)23)12-15(22)8-5-6-9-20(25)26/h10-11,14,16-18,21,23H,2-9,12-13H2,1H3,(H,25,26)/b11-10+/t14-,16+,17+,18+/m0/s1

InChI Key

ROUDCKODIMKLNO-CTBSXBMHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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
Fatty alcohol
Hydroxy fatty acid
Keto fatty acid
Cyclopentanol
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

prostaglandins E (CHEBI:28269 )
Prostaglandins (C05962 )
Prostaglandins (LMFA03010012 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	2.02	ALOGPS
logP	2.41	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	4.1	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.9 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	98.96 m³·mol⁻¹	ChemAxon
Polarizability	42.05 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

External Links

HMDB ID

HMDB0004241

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023346

KNApSAcK ID

Not Available

Chemspider ID

4444412

KEGG Compound ID

C05962

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

7036

PubChem Compound

5280889

PDB ID

Not Available

ChEBI ID

28269

Good Scents ID

Not Available

References

General References

Mastacchi R, Fadda S, Tomasi V, Barnabei O: The effect of 6-keto-prostaglandin E1 on human lymphocyte cAMP levels. Prostaglandins Med. 1980 Dec;5(6):487-94. doi: 10.1016/0161-4630(80)90072-5. [PubMed:6258185 ]
Stanton BJ, Coupar IM: Influence of the thromboxane-mimetic U-46619 and the prostacyclin metabolite 6-keto prostaglandin E1 on vasoconstriction induced by noradrenaline and 5-HT in rat mesenteric vasculature. Prostaglandins Leukot Essent Fatty Acids. 1988 Jul;33(1):7-12. doi: 10.1016/0952-3278(88)90116-0. [PubMed:3186779 ]
Panzenbeck MJ, Hintze TH, Kaley G: 6-Keto-prostaglandin E1 is a potent coronary vasodilator and stimulates a vagal reflex in dogs. J Pharmacol Exp Ther. 1988 Mar;244(3):814-9. [PubMed:3075239 ]
Gibson BE, Buchanan MR, Barr RD, White JG: Primary thrombocythaemia in childhood: symptomatic episodes and their relationship to thromboxane A2, 6-keto-PGE1 and 12-hydroxy-eicosatetraenoic acid production: a case report. Prostaglandins Leukot Med. 1987 Mar;26(3):221-31. doi: 10.1016/0262-1746(87)90032-1. [PubMed:3472253 ]
Miyamori I, Morise T, Yasuhara S, Takeda Y, Koshida H, Takeda R: Single-blind study of epoprostenol and 6-keto-prostaglandin E1 in man: effects of platelet aggregation and plasma renin. Br J Clin Pharmacol. 1985 Dec;20(6):681-3. doi: 10.1111/j.1365-2125.1985.tb05128.x. [PubMed:3912001 ]

Showing NP-Card for 6-Ketoprostaglandin E1 (NP0087161)

MOL for NP0087161 (6-Ketoprostaglandin E1)

3D MOL for NP0087161 (6-Ketoprostaglandin E1)

3D SDF for NP0087161 (6-Ketoprostaglandin E1)

3D-SDF for NP0087161 (6-Ketoprostaglandin E1)

PDB for NP0087161 (6-Ketoprostaglandin E1)

3D PDB for NP0087161 (6-Ketoprostaglandin E1)

SMILES for NP0087161 (6-Ketoprostaglandin E1)

INCHI for NP0087161 (6-Ketoprostaglandin E1)

Structure for NP0087161 (6-Ketoprostaglandin E1)

3D Structure for NP0087161 (6-Ketoprostaglandin E1)