NP-MRD: Showing NP-Card for 2-(14,15-Epoxyeicosatrienoyl) glycerol (NP0339384)

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Record Information

Version

2.0

Created at

2024-09-11 21:33:53 UTC

Updated at

2024-09-11 21:33:53 UTC

NP-MRD ID

NP0339384

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(14,15-Epoxyeicosatrienoyl) glycerol

Description

2-(14,15-Epoxyeicosatrienoyl) glycerol is also known as 14,15-eet 2-glyceryl ester or 2-14,15-eg. 2-(14,15-Epoxyeicosatrienoyl) glycerol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on 2-(14,15-Epoxyeicosatrienoyl) glycerol.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05272300062D          

 28 28  0  0  0  0            999 V2000
   17.9628  -15.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5503  -14.3288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7254  -14.3288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3129  -13.6143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4880  -13.6143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0755  -12.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0755  -12.0748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3609  -12.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5360  -12.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1235  -13.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2986  -13.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8861  -12.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2986  -11.7728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8867  -11.0588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0617  -11.0582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6487  -11.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8238  -11.7715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4113  -11.0563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8244  -10.3431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4113   -9.6285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8238   -8.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6493   -8.9134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4113   -8.1988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8238   -7.4843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6487   -7.4843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0611   -6.7704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4113   -6.7704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8238   -6.0558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 27  1  0  0  0  0
 25 26  1  0  0  0  0
 27 28  1  0  0  0  0
M  END


  Mrv2104 05272300062D          

 28 28  0  0  0  0            999 V2000
   17.9628  -15.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5503  -14.3288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7254  -14.3288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3129  -13.6143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4880  -13.6143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0755  -12.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0755  -12.0748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3609  -12.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5360  -12.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1235  -13.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2986  -13.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8861  -12.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2986  -11.7728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8867  -11.0588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0617  -11.0582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6487  -11.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8238  -11.7715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4113  -11.0563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8244  -10.3431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4113   -9.6285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8238   -8.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6493   -8.9134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4113   -8.1988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8238   -7.4843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6487   -7.4843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0611   -6.7704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4113   -6.7704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8238   -6.0558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 27  1  0  0  0  0
 25 26  1  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339384

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC1OC1C\C=C/C\C=C/C\C=C/CCCC(=O)OC(CO)CO

> <INCHI_IDENTIFIER>
InChI=1/C23H38O5/c1-2-3-12-15-21-22(28-21)16-13-10-8-6-4-5-7-9-11-14-17-23(26)27-20(18-24)19-25/h4,6-7,9-10,13,20-22,24-25H,2-3,5,8,11-12,14-19H2,1H3/b6-4-,9-7-,13-10-

> <INCHI_KEY>
LPMVKZXODWQHGJ-ILYOTBPNNA-N

> <FORMULA>
C23H38O5

> <MOLECULAR_WEIGHT>
394.552

> <EXACT_MASS>
394.271924324

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
46.629313707920375

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3-dihydroxypropan-2-yl (5Z,8Z,11Z)-13-(3-pentyloxiran-2-yl)trideca-5,8,11-trienoate

> <JCHEM_LOGP>
4.474631008

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.979619367999383

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.27837284201132

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9827691988008223

> <JCHEM_POLAR_SURFACE_AREA>
79.29

> <JCHEM_REFRACTIVITY>
115.38219999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1,3-dihydroxypropan-2-yl (5Z,8Z,11Z)-13-(3-pentyloxiran-2-yl)trideca-5,8,11-trienoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-23         0                                  
HETATM    1  C   UNK     0      33.531 -28.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      32.761 -26.747   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      31.221 -26.747   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      30.451 -25.413   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      28.911 -25.413   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.141 -24.080   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      28.141 -22.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      26.807 -23.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      25.267 -23.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.497 -24.644   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.957 -24.644   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.187 -23.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.957 -21.976   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      22.189 -20.643   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.649 -20.642   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      19.878 -21.975   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      18.338 -21.973   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.568 -20.638   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.339 -19.307   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.568 -17.973   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      18.338 -16.638   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      19.879 -16.638   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      17.568 -15.304   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      18.338 -13.971   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      19.878 -13.971   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      20.647 -12.638   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      17.568 -12.638   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      18.338 -11.304   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6    8                                                       
CONECT    8    6    7    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28                                                       
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   56    0
END

View in JSmol

Synonyms

Value	Source
14,15-EET 2-glyceryl ester	ChEBI
14,15-Epoxy-(5Z,8Z,11Z)-eicosatrienoic acid 2-glyceryl ester	ChEBI
14,15-Epoxy-(5Z,8Z,11Z)-icosatrienoic acid 2-glyceryl ester	ChEBI
2-14,15-EG	ChEBI
2-[14,15-Epoxy-(5Z,8Z,11Z)-eicosatrienoyl]glycerol	ChEBI
2-[14,15-Epoxy-(5Z,8Z,11Z)-icosatrienoyl]glycerol	ChEBI
2-Glyceryl 14,15-eet	ChEBI
2-Glyceryl-14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate	ChEBI
14,15-Epoxy-(5Z,8Z,11Z)-eicosatrienoate 2-glyceryl ester	Generator
14,15-Epoxy-(5Z,8Z,11Z)-icosatrienoate 2-glyceryl ester	Generator
2-Glyceryl-14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoic acid	Generator
2-(14,15-Epoxyeicosatrienoyl) glycerol	ChEBI
2-Glyceryl 14,15-epoxy-(5Z,8Z,11Z)-icosatrienoic acid	Generator

Chemical Formula

C₂₃H₃₈O₅

Average Mass

394.5520 Da

Monoisotopic Mass

394.27192 Da

IUPAC Name

1,3-dihydroxypropan-2-yl (5Z,8Z,11Z)-13-(3-pentyloxiran-2-yl)trideca-5,8,11-trienoate

Traditional Name

1,3-dihydroxypropan-2-yl (5Z,8Z,11Z)-13-(3-pentyloxiran-2-yl)trideca-5,8,11-trienoate

CAS Registry Number

Not Available

SMILES

CCCCCC1OC1C\C=C/C\C=C/C\C=C/CCCC(=O)OC(CO)CO

InChI Identifier

InChI=1/C23H38O5/c1-2-3-12-15-21-22(28-21)16-13-10-8-6-4-5-7-9-11-14-17-23(26)27-20(18-24)19-25/h4,6-7,9-10,13,20-22,24-25H,2-3,5,8,11-12,14-19H2,1H3/b6-4-,9-7-,13-10-

InChI Key

LPMVKZXODWQHGJ-ILYOTBPNNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Classification

Not classified

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	4.47	ChemAxon
pKa (Strongest Acidic)	14.28	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.29 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	115.38 m³·mol⁻¹	ChemAxon
Polarizability	46.63 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

132121

Good Scents ID

Not Available

References

General References

Showing NP-Card for 2-(14,15-Epoxyeicosatrienoyl) glycerol (NP0339384)

MOL for NP0339384 (2-(14,15-Epoxyeicosatrienoyl) glycerol)

3D MOL for NP0339384 (2-(14,15-Epoxyeicosatrienoyl) glycerol)

3D SDF for NP0339384 (2-(14,15-Epoxyeicosatrienoyl) glycerol)

3D-SDF for NP0339384 (2-(14,15-Epoxyeicosatrienoyl) glycerol)

PDB for NP0339384 (2-(14,15-Epoxyeicosatrienoyl) glycerol)

3D PDB for NP0339384 (2-(14,15-Epoxyeicosatrienoyl) glycerol)

SMILES for NP0339384 (2-(14,15-Epoxyeicosatrienoyl) glycerol)

INCHI for NP0339384 (2-(14,15-Epoxyeicosatrienoyl) glycerol)

Structure for NP0339384 (2-(14,15-Epoxyeicosatrienoyl) glycerol)

3D Structure for NP0339384 (2-(14,15-Epoxyeicosatrienoyl) glycerol)