NP-MRD: Showing NP-Card for 15-keto-pge2 (NP0161777)

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Record Information

Version

2.0

Created at

2022-09-02 20:02:11 UTC

Updated at

2022-09-02 20:02:11 UTC

NP-MRD ID

NP0161777

Secondary Accession Numbers

None

Natural Product Identification

Common Name

15-keto-pge2

Description

15-Keto-prostaglandin E2, also known as 15-keto-pge2, 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, 15-keto-prostaglandin E2 is considered to be an eicosanoid lipid molecule. Dinoprostone is a naturally occurring prostaglandin E2 (PGE2) and the most common and most biologically active of the mammalian prostaglandins. All mammalian cells except erythrocytes synthesize eicosanoids. 15-Keto-prostaglandin E2 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. The PGs and TXs are collectively identified as prostanoids. Depending on the nature of maturation signals, PGE2 has different and sometimes opposite effects on DC biology. 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. 15-keto-pge2 is found in Gracilaria gracilis. 15-keto-pge2 was first documented in 1980 (PMID: 7190512). 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 (PMID: 6698991).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 55 55  0  0  0  0  0  0  0  0999 V2000
    7.2365   -0.5991    0.8833 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4516   -0.6999   -0.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1516   -0.4386   -1.3732 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1537   -1.4679   -0.9325 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8121   -1.3760   -1.6018 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1071   -0.1022   -1.4039 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6761    0.9600   -1.7995 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7877    0.0545   -0.7828 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0554   -0.9197   -0.3115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2551   -0.7537    0.3052 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0892   -1.1198    1.7965 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2021   -2.4530    1.9487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4523   -0.7200    2.3192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6444    0.6188    1.6676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3084    1.5591    2.0135 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8149    0.6134    0.4162 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7305    0.9787   -0.7384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8763    0.1228   -0.9195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1263    0.4866   -0.8875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5555    1.8632   -0.6529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4601    1.8821    0.5900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6769    1.0012    0.3752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4994    1.4148   -0.7583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9555    2.5857   -0.7969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7954    0.5586   -1.8025 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3839    0.0874    1.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0154   -1.6018    1.3442 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1340   -0.1582    1.3660 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1898    0.0818   -0.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8454   -1.6986   -0.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8182    0.5810   -1.0754 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3696   -0.5345   -2.4354 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0756   -1.3782    0.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5303   -2.5060   -1.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8954   -1.6270   -2.7015 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1938   -2.1939   -1.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3441    1.0607   -0.6936 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4297   -1.9521   -0.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0018   -1.4589   -0.1480 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6611   -0.4230    2.1968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1882   -2.5490    1.9976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4429   -0.6464    3.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1909   -1.4160    1.9270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0615    1.4132    0.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0653    0.8307   -1.6574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9081    2.0620   -0.7118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7037   -0.9584   -1.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9470   -0.2519   -1.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7699    2.5986   -0.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1330    2.2634   -1.5210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7972    2.9090    0.8371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9545    1.4800    1.4834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4040   -0.0664    0.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2560    1.0824    1.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8329    0.9203   -2.7663 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  2  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 25  1  0
 23 24  2  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
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  6
 11 40  1  1
 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 02231219392D          

 25 25  0  0  1  0            999 V2000
   26.0602  -16.8624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6745  -14.2287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2329  -15.5877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6081  -14.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7107  -18.5694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7516  -12.9199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0370  -13.3324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8021  -16.0976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7516  -12.0949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6306  -15.2906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0370  -14.1574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5868  -16.3525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1560  -16.8624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4660  -11.6824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2755  -17.1174    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.6081  -16.6324    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.9407  -17.1174    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.0206  -17.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8460  -15.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3226  -14.5699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7583  -17.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5430  -17.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6081  -15.8074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3226  -15.3949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1956  -17.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 15  1  1  6  0  0  0
  2 19  1  0  0  0  0
  3 19  2  0  0  0  0
  4 20  2  0  0  0  0
  5 25  2  0  0  0  0
  6  7  1  0  0  0  0
  6  9  1  0  0  0  0
  7 11  1  0  0  0  0
  8 10  1  0  0  0  0
  8 12  1  0  0  0  0
  9 14  1  0  0  0  0
 10 19  1  0  0  0  0
 11 20  1  0  0  0  0
 12 21  1  0  0  0  0
 17 13  1  6  0  0  0
 13 22  1  0  0  0  0
 15 16  1  0  0  0  0
 15 18  1  0  0  0  0
 16 17  1  0  0  0  0
 16 23  1  1  0  0  0
 17 25  1  0  0  0  0
 18 25  1  0  0  0  0
 20 24  1  0  0  0  0
 21 22  2  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0161777

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC(=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/h4,7,12-13,16-17,19,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t16-,17-,19-/m1/s1

> <INCHI_KEY>
YRTJDWROBKPZNV-KMXMBPPJSA-N

> <FORMULA>
C20H30O5

> <MOLECULAR_WEIGHT>
350.4492

> <EXACT_MASS>
350.20932407

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
40.04990499641221

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z)-7-[(1R,2R,3R)-3-hydroxy-5-oxo-2-[(1E)-3-oxooct-1-en-1-yl]cyclopentyl]hept-5-enoic acid

> <ALOGPS_LOGP>
3.27

> <JCHEM_LOGP>
3.636608624999999

> <ALOGPS_LOGS>
-3.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.678218203398721

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.303359015207499

> <JCHEM_PKA_STRONGEST_BASIC>
-2.93524020776586

> <JCHEM_POLAR_SURFACE_AREA>
91.66999999999999

> <JCHEM_REFRACTIVITY>
98.53769999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.83e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15-Keto-PGE2

> <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      48.646 -31.476   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      36.726 -26.560   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      35.901 -29.097   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      45.935 -26.427   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      44.260 -34.663   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      49.936 -24.117   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      48.602 -24.887   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      38.831 -30.049   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      49.936 -22.577   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      38.510 -28.542   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      48.602 -26.427   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      40.295 -30.525   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      43.225 -31.476   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      51.270 -21.807   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      47.181 -31.952   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      45.935 -31.047   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      44.689 -31.952   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      46.705 -33.417   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      37.046 -28.066   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      47.269 -27.197   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      40.615 -32.031   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      42.080 -32.507   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      45.935 -29.507   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      47.269 -28.737   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      45.165 -33.417   0.000  0.00  0.00           C+0
CONECT    1   15                                                            
CONECT    2   19                                                            
CONECT    3   19                                                            
CONECT    4   20                                                            
CONECT    5   25                                                            
CONECT    6    7    9                                                       
CONECT    7    6   11                                                       
CONECT    8   10   12                                                       
CONECT    9    6   14                                                       
CONECT   10    8   19                                                       
CONECT   11    7   20                                                       
CONECT   12    8   21                                                       
CONECT   13   17   22                                                       
CONECT   14    9                                                            
CONECT   15    1   16   18                                                  
CONECT   16   15   17   23                                                  
CONECT   17   13   16   25                                                  
CONECT   18   15   25                                                       
CONECT   19    2    3   10                                                  
CONECT   20    4   11   24                                                  
CONECT   21   12   22                                                       
CONECT   22   13   21                                                       
CONECT   23   16   24                                                       
CONECT   24   20   23                                                       
CONECT   25    5   17   18                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

View in JSmol

Synonyms

Value	Source
(5Z)-(15S)-11alpha-Hydroxy-9,15-dioxoprosta-13-enoate	ChEBI
(5Z,13E)-11alpha-Hydroxy-9,15-dioxoprost-13-enoate	ChEBI
15-Deoxy-15-oxo-prostaglandin e2	ChEBI
15-Keto-pge2	ChEBI
15-Ketoprostaglandin e2	ChEBI
15-oxo-PGE2	ChEBI
(5Z)-(15S)-11a-Hydroxy-9,15-dioxoprosta-13-enoate	Generator
(5Z)-(15S)-11a-Hydroxy-9,15-dioxoprosta-13-enoic acid	Generator
(5Z)-(15S)-11alpha-Hydroxy-9,15-dioxoprosta-13-enoic acid	Generator
(5Z)-(15S)-11Α-hydroxy-9,15-dioxoprosta-13-enoate	Generator
(5Z)-(15S)-11Α-hydroxy-9,15-dioxoprosta-13-enoic acid	Generator
(5Z,13E)-11a-Hydroxy-9,15-dioxoprost-13-enoate	Generator
(5Z,13E)-11a-Hydroxy-9,15-dioxoprost-13-enoic acid	Generator
(5Z,13E)-11alpha-Hydroxy-9,15-dioxoprost-13-enoic acid	Generator
(5Z,13E)-11Α-hydroxy-9,15-dioxoprost-13-enoate	Generator
(5Z,13E)-11Α-hydroxy-9,15-dioxoprost-13-enoic acid	Generator
(5Z)-(13E)-11-alpha-Hydroxy-9,15-dioxoprosta-5,13-dienoate	HMDB
(5Z)-(13E)-11-alpha-Hydroxy-9,15-dioxoprosta-5,13-dienoic acid	HMDB
(5Z,13E)-11-alpha-Hydroxy-9,15-dioxoprost-5,13-dienoate	HMDB
(5Z,13E)-11-alpha-Hydroxy-9,15-dioxoprost-5,13-dienoic acid	HMDB
15-Keto-pge2-alpha	HMDB
15-oxo-PGE2-alpha	HMDB
9,15-Dioxo-11-hydroxyprosta-5,13-dienoic acid	HMDB
15-Ketoprostaglandin e2, (11alpha)-isomer	HMDB
15-Keto-prostaglandin e2	ChEBI

Chemical Formula

C₂₀H₃₀O₅

Average Mass

350.4492 Da

Monoisotopic Mass

350.20932 Da

IUPAC Name

(5Z)-7-[(1R,2R,3R)-3-hydroxy-5-oxo-2-[(1E)-3-oxooct-1-en-1-yl]cyclopentyl]hept-5-enoic acid

Traditional Name

15-Keto-PGE2

CAS Registry Number

Not Available

SMILES

CCCCCC(=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/h4,7,12-13,16-17,19,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t16-,17-,19-/m1/s1

InChI Key

YRTJDWROBKPZNV-KMXMBPPJSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Gracilaria gracilis	LOTUS Database	35616633

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
Unsaturated fatty acid
Fatty acid
Alpha,beta-unsaturated ketone
Cyclic alcohol
Acryloyl-group
Enone
Secondary alcohol
Cyclic ketone
Ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organooxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

prostaglandins E (CHEBI:15547 )
Prostaglandins (LMFA03010030 )

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	3.27	ALOGPS
logP	3.64	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	4.3	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.67 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	98.54 m³·mol⁻¹	ChemAxon
Polarizability	40.05 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

HMDB0003175

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023119

KNApSAcK ID

Not Available

Chemspider ID

4444303

KEGG Compound ID

C04707

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

2309

PubChem Compound

5280719

PDB ID

Not Available

ChEBI ID

15547

Good Scents ID

Not Available

References

General References

Fitzpatrick FA, Liggett WF, Wynalda MA: Albumin-eicosanoid interactions. A model system to determine their attributes and inhibition. J Biol Chem. 1984 Mar 10;259(5):2722-7. [PubMed:6698991 ]
Gordon-Wright AP, Elder MG: Effect of prostaglandin E2 and its metabolites on lower segment myometrium in vitro. Eur J Obstet Gynecol Reprod Biol. 1980 Jun;10(5):297-302. doi: 10.1016/0028-2243(80)90076-3. [PubMed:7190512 ]
LOTUS database [Link]

Showing NP-Card for 15-keto-pge2 (NP0161777)

MOL for NP0161777 (15-keto-pge2)

3D MOL for NP0161777 (15-keto-pge2)

3D SDF for NP0161777 (15-keto-pge2)

3D-SDF for NP0161777 (15-keto-pge2)

PDB for NP0161777 (15-keto-pge2)

3D PDB for NP0161777 (15-keto-pge2)

SMILES for NP0161777 (15-keto-pge2)

INCHI for NP0161777 (15-keto-pge2)

Structure for NP0161777 (15-keto-pge2)

3D Structure for NP0161777 (15-keto-pge2)