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Showing NP-Card for LPA(18:0e/0:0) (NP0334784)

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Record Information
Version2.0
Created at2024-09-10 19:56:50 UTC
Updated at2024-09-10 19:56:50 UTC
NP-MRD IDNP0334784
Secondary Accession NumbersNone
Natural Product Identification
Common NameLPA(18:0e/0:0)
DescriptionPC(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)) belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Fatty acids containing 16, 18 and 20 carbons are the most common. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PC(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)) is an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, PC(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)) participates in a number of enzymatic reactions. In particular, S-adenosylhomocysteine and PC(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)); which is catalyzed by the enzyme phosphatidylethanolamine N-methyltransferase. In addition, cytidine monophosphate and PC(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)) can be biosynthesized from CDP-choline and DG(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/0:0) Through the action of the enzyme choline/ethanolaminephosphotransferase. In humans, PC(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)) is involved in phosphatidylcholine biosynthesis. A third route to PC synthesis involves the conversion of either PS or PE to PC. It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. The eicsoatetraenoic acid moiety is derived from fish oils, while the adrenic acid moiety is derived from animal fats. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. PCs can be synthesized via three different routes.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0334784 (LPA(18:0e/0:0))


  Mrv0541 02241201202D          

 29 28  0  0  1  0            999 V2000
   22.7599   -3.1577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0848   -3.5475    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   21.4097   -3.1577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4350   -3.5475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7345   -3.5475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5580   -4.3271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6726   -4.3568    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8741   -3.5475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5886   -3.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3030   -3.5475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0175   -3.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7320   -3.5475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4465   -3.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1609   -3.5475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8754   -3.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5899   -3.5475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3043   -3.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0188   -3.5475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7333   -3.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4477   -3.5475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1622   -3.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8767   -3.5475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5911   -3.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3056   -3.5475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0201   -3.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1102   -3.1577    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   24.7853   -2.7679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7203   -2.4826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5000   -3.8327    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  0  0  0  0
  2  7  1  1  0  0  0
  9  8  1  0  0  0  0
 10  9  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
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  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
  5 25  1  0  0  0  0
 26  4  1  0  0  0  0
 27 26  2  0  0  0  0
 28 26  1  0  0  0  0
 29 26  1  0  0  0  0
M  END
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3D MOL for NP0334784 (LPA(18:0e/0:0))

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3D SDF for NP0334784 (LPA(18:0e/0:0))

  Mrv0541 02241201202D          

 29 28  0  0  1  0            999 V2000
   22.7599   -3.1577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0848   -3.5475    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   21.4097   -3.1577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4350   -3.5475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7345   -3.5475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5580   -4.3271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6726   -4.3568    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8741   -3.5475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5886   -3.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3030   -3.5475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0175   -3.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7320   -3.5475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4465   -3.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1609   -3.5475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8754   -3.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5899   -3.5475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3043   -3.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0188   -3.5475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7333   -3.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4477   -3.5475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1622   -3.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8767   -3.5475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5911   -3.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3056   -3.5475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0201   -3.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1102   -3.1577    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   24.7853   -2.7679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7203   -2.4826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5000   -3.8327    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  0  0  0  0
  2  7  1  1  0  0  0
  9  8  1  0  0  0  0
 10  9  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
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  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
  5 25  1  0  0  0  0
 26  4  1  0  0  0  0
 27 26  2  0  0  0  0
 28 26  1  0  0  0  0
 29 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334784

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@](O)(COCCCCCCCCCCCCCCCCCC)COP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H45O6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-26-19-21(22)20-27-28(23,24)25/h21-22H,2-20H2,1H3,(H2,23,24,25)/t21-/m1/s1

> <INCHI_KEY>
HUUYDUFSUADEJQ-OAQYLSRUSA-N

> <FORMULA>
C21H45O6P

> <MOLECULAR_WEIGHT>
424.5522

> <EXACT_MASS>
424.295375684

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
51.54609082960159

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R)-2-hydroxy-3-(octadecyloxy)propoxy]phosphonic acid

> <ALOGPS_LOGP>
5.43

> <JCHEM_LOGP>
6.228406774333334

> <ALOGPS_LOGS>
-5.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.532823087649438

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5070267056744795

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3931742588163853

> <JCHEM_POLAR_SURFACE_AREA>
96.22

> <JCHEM_REFRACTIVITY>
114.42779999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.41e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-hydroxy-3-(octadecyloxy)propoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0334784 (LPA(18:0e/0:0))
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PDB for NP0334784 (LPA(18:0e/0:0))
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      42.485  -5.894   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      41.225  -6.622   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      39.965  -5.894   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      43.745  -6.622   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      38.704  -6.622   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      40.242  -8.077   0.000  0.00  0.00           O+0
HETATM    7  H   UNK     0      42.322  -8.133   0.000  0.00  0.00           H+0
HETATM    8  C   UNK     0      14.698  -6.622   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.032  -5.852   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.366  -6.622   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.699  -5.852   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.033  -6.622   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.367  -5.852   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      22.700  -6.622   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      24.034  -5.852   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      25.368  -6.622   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      26.701  -5.852   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.035  -6.622   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      29.369  -5.852   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      30.702  -6.622   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      32.036  -5.852   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      33.370  -6.622   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      34.703  -5.852   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      36.037  -6.622   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      37.371  -5.852   0.000  0.00  0.00           C+0
HETATM   26  P   UNK     0      45.006  -5.894   0.000  0.00  0.00           P+0
HETATM   27  O   UNK     0      46.266  -5.167   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      44.278  -4.634   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      45.733  -7.154   0.000  0.00  0.00           O+0
CONECT    1    2    4                                                       
CONECT    2    1    3    6    7                                             
CONECT    3    2    5                                                       
CONECT    4    1   26                                                       
CONECT    5    3   25                                                       
CONECT    6    2                                                            
CONECT    7    2                                                            
CONECT    8    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                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24    5                                                       
CONECT   26    4   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   56    0
END

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3D PDB for NP0334784 (LPA(18:0e/0:0))
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SMILES for NP0334784 (LPA(18:0e/0:0))
[H][C@@](O)(COCCCCCCCCCCCCCCCCCC)COP(O)(O)=O
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INCHI for NP0334784 (LPA(18:0e/0:0))
InChI=1S/C21H45O6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-26-19-21(22)20-27-28(23,24)25/h21-22H,2-20H2,1H3,(H2,23,24,25)/t21-/m1/s1
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Synonyms
ValueSource
1-Octadecyl-sn-glycero-3-phosphateHMDB
LysoPA(18:0E)HMDB
LysoPA(O-18:0)HMDB
PA(O-18:0/0:0)HMDB
[(2R)-2-Hydroxy-3-octadecoxy-propyl] dihydrogen phosphateHMDB
Chemical FormulaC21H45O6P
Average Mass424.5522 Da
Monoisotopic Mass424.29538 Da
IUPAC Name[(2R)-2-hydroxy-3-(octadecyloxy)propoxy]phosphonic acid
Traditional Name(2R)-2-hydroxy-3-(octadecyloxy)propoxyphosphonic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(COCCCCCCCCCCCCCCCCCC)COP(O)(O)=O
InChI Identifier
InChI=1S/C21H45O6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-26-19-21(22)20-27-28(23,24)25/h21-22H,2-20H2,1H3,(H2,23,24,25)/t21-/m1/s1
InChI KeyHUUYDUFSUADEJQ-OAQYLSRUSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassGlycerophospholipids  
Sub ClassGlycerophosphocholines  
Direct ParentPhosphatidylcholines  
Alternative Parents
Substituents
  • Diacylglycero-3-phosphocholine
    • 

  • Phosphocholine
    • 

  • Dialkyl phosphate
    • 

  • Fatty acid ester
    • 

  • Fatty acyl
    • 

  • Alkyl phosphate
    • 

  • Phosphoric acid ester
    • 

  • Organic phosphoric acid derivative
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Tetraalkylammonium salt
    • 

  • Quaternary ammonium salt
    • 

  • Carboxylic acid ester
    • 

  • Carboxylic acid derivative
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organic salt
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Carbonyl group
    • 

  • Amine
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.43ALOGPS
logP6.23ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)1.51ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity114.43 m³·mol⁻¹ChemAxon
Polarizability51.55 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB025672  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
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References
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