NP-MRD: Showing NP-Card for Phosphatidylethanolamine (NP0046701)

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Record Information

Version

2.0

Created at

2022-03-17 20:11:27 UTC

Updated at

2022-03-17 20:11:28 UTC

NP-MRD ID

NP0046701

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Phosphatidylethanolamine

Description

PE(P-18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)), also known as gpe(O-18:2(1Z,11Z)/20:5N3) or gpe(O-18:2(1Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)), belongs to the class of organic compounds known as 1-(1z-alkenyl),2-acylglycerophosphoethanolamines. These are glycerophosphoethanolamines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one 1Z-alkenyl chain attached through an ether linkage at the O1-position. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). PE(P-18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)) is a very strong basic compound (based on its pKa). Outside of the human body, PE(P-18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)) is found, on average, in the highest concentration within a few different foods, such as sesames, soy beans, and milk (cow) and in a lower concentration in sunflowers. PE(P-18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)) has also been detected, but not quantified in, several different foods, such as common wheats, common pea, lemons, spinachs, and white lupines. This could make PE(P-18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)) a potential biomarker for the consumption of these foods. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. Plasmalogens are glycerol ether phospholipids. Choline plasmalogen is abundant in cardiac tissue. PE synthesis can occur via two pathways. Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241201382D          

 53 52  0  0  1  0            999 V2000
   19.4585   -6.3955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7753   -6.7900    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.0920   -6.3955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1418   -6.7900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4088   -6.7900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2422   -7.5790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8250   -6.3955    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   20.4306   -5.7122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2195   -7.0787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5083   -6.0010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1915   -6.3955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8748   -6.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5581   -6.3955    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.3701   -7.6090    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.6917   -6.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9747   -6.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2576   -6.7900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5405   -6.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8235   -6.7900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1065   -6.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3894   -6.7900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6838   -6.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9667   -6.7900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2496   -6.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5326   -6.7900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8155   -6.7900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0985   -6.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3814   -6.7900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6644   -6.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9469   -6.7900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2299   -6.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5124   -6.7900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9527   -7.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6671   -7.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3816   -7.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0961   -7.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8105   -7.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5250   -7.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2395   -7.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9540   -7.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6685   -7.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3829   -7.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0974   -7.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8119   -7.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5263   -7.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2408   -7.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9553   -7.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6698   -7.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3843   -7.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0987   -7.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8132   -7.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5277   -7.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5277   -8.8165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  3  1  0  0  0  0
  2  6  1  6  0  0  0
  7  4  1  0  0  0  0
  8  7  2  0  0  0  0
  9  7  1  0  0  0  0
 10  7  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
  2 14  1  1  0  0  0
 16 15  2  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
 25 24  1  0  0  0  0
 26 25  2  0  0  0  0
 27 26  1  0  0  0  0
 28 27  1  0  0  0  0
 29 28  1  0  0  0  0
 30 29  1  0  0  0  0
  5 15  1  0  0  0  0
 31 30  1  0  0  0  0
 32 31  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  2  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52  6  1  0  0  0  0
 52 53  2  0  0  0  0
M  END


  Mrv0541 02241201382D          

 53 52  0  0  1  0            999 V2000
   19.4585   -6.3955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7753   -6.7900    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.0920   -6.3955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1418   -6.7900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4088   -6.7900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2422   -7.5790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8250   -6.3955    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   20.4306   -5.7122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2195   -7.0787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5083   -6.0010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1915   -6.3955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8748   -6.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5581   -6.3955    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.3701   -7.6090    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.6917   -6.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9747   -6.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2576   -6.7900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5405   -6.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8235   -6.7900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1065   -6.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3894   -6.7900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6838   -6.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9667   -6.7900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2496   -6.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5326   -6.7900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8155   -6.7900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0985   -6.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3814   -6.7900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6644   -6.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9469   -6.7900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2299   -6.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5124   -6.7900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9527   -7.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6671   -7.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3816   -7.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0961   -7.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8105   -7.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5250   -7.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2395   -7.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9540   -7.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6685   -7.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3829   -7.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0974   -7.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8119   -7.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5263   -7.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2408   -7.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9553   -7.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6698   -7.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3843   -7.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0987   -7.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8132   -7.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5277   -7.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5277   -8.8165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  3  1  0  0  0  0
  2  6  1  6  0  0  0
  7  4  1  0  0  0  0
  8  7  2  0  0  0  0
  9  7  1  0  0  0  0
 10  7  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
  2 14  1  1  0  0  0
 16 15  2  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
 25 24  1  0  0  0  0
 26 25  2  0  0  0  0
 27 26  1  0  0  0  0
 28 27  1  0  0  0  0
 29 28  1  0  0  0  0
 30 29  1  0  0  0  0
  5 15  1  0  0  0  0
 31 30  1  0  0  0  0
 32 31  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  2  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52  6  1  0  0  0  0
 52 53  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0046701

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@](CO\C=C/CCCCCCCC\C=C/CCCCCC)(COP(O)(=O)OCCN)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC

> <INCHI_IDENTIFIER>
InChI=1S/C43H74NO7P/c1-3-5-7-9-11-13-15-17-19-21-22-24-26-28-30-32-34-36-43(45)51-42(41-50-52(46,47)49-39-37-44)40-48-38-35-33-31-29-27-25-23-20-18-16-14-12-10-8-6-4-2/h5,7,11,13-14,16-17,19,22,24,28,30,35,38,42H,3-4,6,8-10,12,15,18,20-21,23,25-27,29,31-34,36-37,39-41,44H2,1-2H3,(H,46,47)/b7-5-,13-11-,16-14-,19-17-,24-22-,30-28-,38-35-/t42-/m1/s1

> <INCHI_KEY>
RDLRIZLZWSNORN-FSOAWXQVSA-N

> <FORMULA>
C43H74NO7P

> <MOLECULAR_WEIGHT>
748.0239

> <EXACT_MASS>
747.520290239

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
87.98994348783715

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-aminoethoxy)[(2R)-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]-3-[(1Z,11Z)-octadeca-1,11-dien-1-yloxy]propoxy]phosphinic acid

> <ALOGPS_LOGP>
8.97

> <JCHEM_LOGP>
11.339572050116605

> <ALOGPS_LOGS>
-7.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8688005890407542

> <JCHEM_PKA_STRONGEST_BASIC>
9.999929336362282

> <JCHEM_POLAR_SURFACE_AREA>
117.31

> <JCHEM_REFRACTIVITY>
225.64800000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
38

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.11e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-aminoethoxy(2R)-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]-3-[(1Z,11Z)-octadeca-1,11-dien-1-yloxy]propoxyphosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      36.323 -11.938   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      35.047 -12.675   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      33.772 -11.938   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      37.598 -12.675   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      32.496 -12.675   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      34.052 -14.147   0.000  0.00  0.00           O+0
HETATM    7  P   UNK     0      38.873 -11.938   0.000  0.00  0.00           P+0
HETATM    8  O   UNK     0      38.137 -10.663   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      39.610 -13.214   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      40.149 -11.202   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      41.424 -11.938   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      42.700 -11.202   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      43.975 -11.938   0.000  0.00  0.00           N+0
HETATM   14  H   UNK     0      36.158 -14.203   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0      31.158 -11.913   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      29.819 -11.913   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      28.481 -12.675   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      27.142 -11.913   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      25.804 -12.675   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      24.465 -11.913   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      23.127 -12.675   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      21.810 -11.913   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      20.471 -12.675   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      19.133 -11.913   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.794 -12.675   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      16.456 -12.675   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.117 -11.913   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.779 -12.675   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.440 -11.913   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.101 -12.675   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.762 -11.913   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.423 -12.675   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.378 -14.917   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.712 -14.147   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.046 -14.917   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      11.379 -14.917   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      12.713 -14.147   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      14.047 -14.917   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      15.380 -14.917   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      16.714 -14.147   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      18.048 -14.917   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      19.381 -14.917   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      20.715 -14.147   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      22.049 -14.917   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      23.382 -14.917   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      24.716 -14.147   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      26.050 -14.917   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      27.384 -14.917   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      28.717 -14.147   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      30.051 -14.917   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      31.385 -14.147   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      32.718 -14.917   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      32.718 -16.457   0.000  0.00  0.00           O+0
CONECT    1    2    4                                                       
CONECT    2    1    3    6   14                                             
CONECT    3    2    5                                                       
CONECT    4    1    7                                                       
CONECT    5    3   15                                                       
CONECT    6    2   52                                                       
CONECT    7    4    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14    2                                                            
CONECT   15   16    5                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   34                                                            
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51    6   53                                                  
CONECT   53   52                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  104    0
END

View in JSmol

Synonyms

Value	Source
(2-Aminoethoxy)[(2R)-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]-3-[(1Z,11Z)-octadeca-1,11-dien-1-yloxy]propoxy]phosphinate	HMDB
1-(1Z,11Z-Octadecadienyl)-2-eicosapentaenoyl-gpe	HMDB
1-(1Z,11Z-Octadecadienyl)-2-eicosapentaenoyl-sn-glycero-3-phosphoethanolamine	HMDB
1-(1Z,11Z-Octadecadienyl)-2-eicosapentaenoyl-sn-glycero-phosphatidylethanolamine	HMDB
GPE(18:2/20:5)	HMDB
GPE(38:7)	HMDB
GPE(O-18:2(1Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))	HMDB
GPE(O-18:2(1Z,11Z)/20:5n3)	HMDB
GPE(O-18:2(1Z,11Z)/20:5W3)	HMDB
GPE(p-18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))	HMDB
GPE(p-18:1(11Z)/20:5n3)	HMDB
GPE(p-18:1(11Z)/20:5W3)	HMDB
GPEtn(18:2/20:5)	HMDB
GPEtn(38:7)	HMDB
GPEtn(O-18:2(1Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))	HMDB
GPEtn(O-18:2(1Z,11Z)/20:5n3)	HMDB
GPEtn(O-18:2(1Z,11Z)/20:5W3)	HMDB
GPEtn(p-18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))	HMDB
GPEtn(p-18:1(11Z)/20:5n3)	HMDB
GPEtn(p-18:1(11Z)/20:5W3)	HMDB
PE(18:2/20:5)	HMDB
PE(38:7)	HMDB
PE(O-18:2(1Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))	HMDB
PE(O-18:2(1Z,11Z)/20:5N3)	HMDB
PE(O-18:2(1Z,11Z)/20:5W3)	HMDB
PE(P-18:1(11Z)/20:5N3)	HMDB
PE(P-18:1(11Z)/20:5W3)	HMDB
Phosphatidylethanolamine(18:2/20:5)	HMDB
Phosphatidylethanolamine(38:7)	HMDB
Phosphatidylethanolamine(O-18:2(1Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))	HMDB
Phosphatidylethanolamine(O-18:2(1Z,11Z)/20:5n3)	HMDB
Phosphatidylethanolamine(O-18:2(1Z,11Z)/20:5W3)	HMDB
Phosphatidylethanolamine(p-18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))	HMDB
Phosphatidylethanolamine(p-18:1(11Z)/20:5n3)	HMDB
Phosphatidylethanolamine(p-18:1(11Z)/20:5W3)	HMDB

Chemical Formula

C₄₃H₇₄NO₇P

Average Mass

748.0239 Da

Monoisotopic Mass

747.52029 Da

IUPAC Name

(2-aminoethoxy)[(2R)-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]-3-[(1Z,11Z)-octadeca-1,11-dien-1-yloxy]propoxy]phosphinic acid

Traditional Name

2-aminoethoxy(2R)-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]-3-[(1Z,11Z)-octadeca-1,11-dien-1-yloxy]propoxyphosphinic acid

CAS Registry Number

50-59-9

SMILES

[H][C@@](CO\C=C/CCCCCCCC\C=C/CCCCCC)(COP(O)(=O)OCCN)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC

InChI Identifier

InChI=1S/C43H74NO7P/c1-3-5-7-9-11-13-15-17-19-21-22-24-26-28-30-32-34-36-43(45)51-42(41-50-52(46,47)49-39-37-44)40-48-38-35-33-31-29-27-25-23-20-18-16-14-12-10-8-6-4-2/h5,7,11,13-14,16-17,19,22,24,28,30,35,38,42H,3-4,6,8-10,12,15,18,20-21,23,25-27,29,31-34,36-37,39-41,44H2,1-2H3,(H,46,47)/b7-5-,13-11-,16-14-,19-17-,24-22-,30-28-,38-35-/t42-/m1/s1

InChI Key

RDLRIZLZWSNORN-FSOAWXQVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

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
Citrus limon	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Glycine max	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Helianthus annuus L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Lactuca sativa	FooDB	15986496
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Lupinus albus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
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
Pisum sativum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sesamum indicum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Spinacia oleracea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Triticum aestivum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vitis vinifera L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-(1z-alkenyl),2-acylglycerophosphoethanolamines. These are glycerophosphoethanolamines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one 1Z-alkenyl chain attached through an ether linkage at the O1-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoethanolamines

Direct Parent

1-(1Z-alkenyl),2-acylglycerophosphoethanolamines

Alternative Parents

Substituents

1-(1z-alkenyl),2-acylglycerophosphoethanolamine
Glycerol vinyl ether
Phosphoethanolamine
Fatty acid ester
Dialkyl phosphate
Fatty acyl
Alkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Primary amine
Primary aliphatic amine
Organic oxygen compound
Amine
Carbonyl group
Organopnictogen compound
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

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	8.97	ALOGPS
logP	11.34	ChemAxon
logS	-7	ALOGPS
pKa (Strongest Acidic)	1.87	ChemAxon
pKa (Strongest Basic)	10	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	117.31 Å²	ChemAxon
Rotatable Bond Count	38	ChemAxon
Refractivity	225.65 m³·mol⁻¹	ChemAxon
Polarizability	87.99 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0011420

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB005556

KNApSAcK ID

Not Available

Chemspider ID

24769304

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53480880

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Phosphatidylethanolamine (NP0046701)

MOL for NP0046701 (Phosphatidylethanolamine)

3D MOL for NP0046701 (Phosphatidylethanolamine)

3D SDF for NP0046701 (Phosphatidylethanolamine)

3D-SDF for NP0046701 (Phosphatidylethanolamine)

PDB for NP0046701 (Phosphatidylethanolamine)

3D PDB for NP0046701 (Phosphatidylethanolamine)

SMILES for NP0046701 (Phosphatidylethanolamine)

INCHI for NP0046701 (Phosphatidylethanolamine)

Structure for NP0046701 (Phosphatidylethanolamine)

3D Structure for NP0046701 (Phosphatidylethanolamine)