MiMeDB: Showing metabocard for LysoPC(20:4(5Z,8Z,11Z,14Z)) (MMDBc0034130)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 05:17:15 UTC

Update Date

2024-04-30 20:21:43 UTC

Metabolite ID

MMDBc0034130

Metabolite Identification

Common Name

LysoPC(20:4(5Z,8Z,11Z,14Z))

Description

LysoPC(20:4(5Z,8Z,11Z,14Z)) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) position. Fatty acids containing 16, 18 and 20 carbons are the most common. LysoPC(20:4(5Z,8Z,11Z,14Z)), in particular, consists of one chain of arachidonic acid at the C-1 position. The arachidonic acid moiety is derived from animal fats and eggs. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2, as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling. In blood plasma significant amounts of lysophosphatidylcholine are formed by a specific enzyme system, lecithin:cholesterol acyltransferase (LCAT), which is secreted from the liver. The enzyme catalyzes the transfer of the fatty acids of position sn-2 of phosphatidylcholine to the free cholesterol in plasma, with formation of cholesterol esters and lysophosphatidylcholine. Lysophospholipids have a role in lipid signaling by acting on lysophospholipid receptors (LPL-R). LPL-R's are members of the G protein-coupled receptor family of integral membrane proteins. LPL-R's are members of the G protein-coupled receptor (GPR) family of integral membrane proteins. Lysophosphatidylcholines (LPCs) specifically bind to GPR119, GPR40, GPR55 and GPR4. binding of LPCs to GPR119, GPR40 and GPR55 induces intracellular calcium mobilization and leads to increased glucose-stimulated insulin secretion in different cell systems. In blood or plasma LPCs are bound mainly to albumin and to a lesser extent to lipoproteins. Inflammation, cell damage and other pathophysiological conditions can profoundly alter the ratio of free to albumin bound LPC through increased production of LPC or decreased plasma levels of albumin (PMID: 32599910 ). In particular, lower levels of albumin (hypoalbuminemia) lead to lower levels of LPC in the blood. Hypoalbuminemia with albumin concentrations of <20 g/L are typical of patients with sepsis, burns or serious trauma (PMID: 26557421 ). Such low levels of albumin often lead to LPC levels that are 50-80 % lower than that seen in healthy individuals (PMID: 27501420 ). Decreased levels of LPC have been observed in a number of other inflammatory conditions beyond sepsis, including rheumatoid arthritis, diabetes, schizophrenia, polycystic ovary syndrome, Alzheimer’s disease, pulmonary arterial hypertension, aging, asthma and liver cirrhosis, where they were associated with increased mortality risk (PMID: 32599910 ). LPCs have a number of protective or anti-inflammatory effects. Higher levels of LPC induce cyclooxygenase-2 and endothelial nitric oxide synthase (eNOS) expression in endothelial cells, both of which can have vasoprotective effects either via production of prostacyclin or nitric oxide (PMID: 32599910 ). LPCs have been shown to elicit a number of effects on the innate immune system and effectively serve as dual-activity ligand molecules. In particular, LPCs directly activate toll-like receptor (TLR) 4 and TLR-2-1 receptors in the absence of classical TLR ligands. However, LPCs can also inhibit TLR-mediated signaling in the presence of classical TLR ligands, thereby acting as anti-inflammatory molecules (PMID: 32599910 ). Low levels of LPC during a bacterial or viral infection with TLR-mediated signalling can lead to opposing (inflammatory vs. anti-inflammatory) effects and immune dysregulation.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02251201572D          

 37 36  0  0  1  0            999 V2000
   -4.1467   -0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4322   -1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4322   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7177   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7177   -3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0033   -3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0033   -4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888   -5.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743   -4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401   -5.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546   -4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546   -3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691   -3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559   -3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993   -2.1434    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9993   -1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4283   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1427   -2.5559    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.7302   -3.2704    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   10.5552   -1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5717   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2862   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0006   -2.5559    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   13.7151   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4131   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5881   -1.8414    0.0000 C   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
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  4  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  4  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  4  0  0  0
 15 16  2  0  0  0  0
 16 17  1  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  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 34 37  1  0  0  0  0
M  CHG  2  29  -1  34   1
M  END


  Mrv0541 02251201572D          

 37 36  0  0  1  0            999 V2000
   -4.1467   -0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4322   -1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4322   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7177   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7177   -3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0033   -3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0033   -4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888   -5.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743   -4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401   -5.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546   -4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546   -3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691   -3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559   -3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993   -2.1434    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9993   -1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4283   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1427   -2.5559    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.7302   -3.2704    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   10.5552   -1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5717   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2862   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0006   -2.5559    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   13.7151   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4131   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5881   -1.8414    0.0000 C   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
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  4  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  4  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  4  0  0  0
 15 16  2  0  0  0  0
 16 17  1  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  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 34 37  1  0  0  0  0
M  CHG  2  29  -1  34   1
M  END
> <DATABASE_ID>
MMDBc0034130

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C28H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-28(31)34-25-27(30)26-36-37(32,33)35-24-23-29(2,3)4/h9-10,12-13,15-16,18-19,27,30H,5-8,11,14,17,20-26H2,1-4H3/t27-/m1/s1

> <INCHI_KEY>
LAXQYRRMGGEGOH-HHHXNRCGSA-N

> <FORMULA>
C28H50NO7P

> <MOLECULAR_WEIGHT>
543.6729

> <EXACT_MASS>
543.332489471

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
61.39960233395377

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{[(2R)-2-hydroxy-3-(icosa-5,8,11,14-tetraenoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

> <ALOGPS_LOGP>
2.45

> <JCHEM_LOGP>
1.5233305101949206

> <ALOGPS_LOGS>
-6.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.655609234867157

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8553406136269377

> <JCHEM_PKA_STRONGEST_BASIC>
-3.404003371460023

> <JCHEM_POLAR_SURFACE_AREA>
105.12000000000002

> <JCHEM_REFRACTIVITY>
165.14409999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
24

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.89e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-{[(2R)-2-hydroxy-3-(icosa-5,8,11,14-tetraenoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0      -7.741  -1.691   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.407  -2.461   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.407  -4.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.073  -4.771   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.073  -6.311   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.739  -7.081   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.739  -8.621   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.406  -9.391   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.072  -8.621   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.262  -9.391   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.595  -8.621   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.595  -7.081   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.929  -6.311   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.929  -4.771   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.263  -4.001   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.596  -4.771   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.930  -4.001   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.264  -4.771   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.597  -4.001   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.931  -4.771   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.931  -6.311   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      12.265  -4.001   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      13.598  -4.771   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.932  -4.001   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      14.932  -2.461   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      16.266  -4.771   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      17.599  -4.001   0.000  0.00  0.00           O+0
HETATM   28  P   UNK     0      18.933  -4.771   0.000  0.00  0.00           P+0
HETATM   29  O   UNK     0      18.163  -6.105   0.000  0.00  0.00           O-1
HETATM   30  O   UNK     0      19.703  -3.437   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      20.267  -5.541   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      21.601  -4.771   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      22.934  -5.541   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0      24.268  -4.771   0.000  0.00  0.00           N+1
HETATM   35  C   UNK     0      25.602  -4.001   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      25.038  -6.105   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      23.498  -3.437   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    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   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36   37                                             
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   34                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   72    0
END

Synonyms

Not Available

Molecular Formula

C₂₈H₅₀NO₇P

Average Mass

543.6729

Monoisotopic Mass

543.332489471

IUPAC Name

(2-{[(2R)-2-hydroxy-3-(icosa-5,8,11,14-tetraenoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-2-hydroxy-3-(icosa-5,8,11,14-tetraenoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C

InChI Identifier

InChI=1S/C28H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-28(31)34-25-27(30)26-36-37(32,33)35-24-23-29(2,3)4/h9-10,12-13,15-16,18-19,27,30H,5-8,11,14,17,20-26H2,1-4H3/t27-/m1/s1

InChI Key

LAXQYRRMGGEGOH-HHHXNRCGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphocholine.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphocholines

Direct Parent

1-acyl-sn-glycero-3-phosphocholines

Alternative Parents

Substituents

1-acyl-sn-glycero-3-phosphocholine
Phosphocholine
Fatty acid ester
Dialkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Tetraalkylammonium salt
Quaternary ammonium salt
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Alcohol
Organic oxygen compound
Organopnictogen compound
Carbonyl group
Organic salt
Amine
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.00029 g/L	ALOGPS
logP	2.45	ALOGPS
logP	1.52	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	105.12 Å²	ChemAxon
Rotatable Bond Count	24	ChemAxon
Refractivity	165.14 m³·mol⁻¹	ChemAxon
Polarizability	61.4 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

Spectra

Spectrum Type	Description	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-18	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

All Tissues
Blood
Cerebrospinal Fluid (CSF)
Feces
Placenta
Saliva
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Obesity	Slight Decrease	Association	Human Blood	HMDB	23108202
Obesity	Slight Decrease	Association	Human Blood	HMDB	24740590
Eosinophilic esophagitis		Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Animal	Milk	Bos taurus	FooDB	Manually Annotated
Animal	Milk	Bos taurus	FooDB	Manually Annotated

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Blood	Detected and Quantified	4.4	1.21			uM	Children (1-13 years old)	Both	Obese	HMDB	23108202
Human Blood	Detected and Quantified	4.5	1.7			uM	Children (1-13 years old)	Both	Obese	HMDB	24740590
Human Blood	Detected and Quantified	4.5	1.9			uM	Children (1-13 years old)	Both	Obese	HMDB	24740590
Human Blood	Detected and Quantified	4.7	2.0			uM	Children (1-13 years old)	Both	Obese	HMDB	24740590
Human Blood	Detected and Quantified	4.8	1.4			uM	Children (1-13 years old)	Both	Obese	HMDB	24740590
Human Blood	Detected and Quantified	7.9856	2.2556			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	24704061
Human Urine	Detected and Quantified			0.0	0.03	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	32340350
Human Urine	Detected and Quantified	0.0		0.0	0.02	umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	HMDB	32340350
Human Urine	Detected and Quantified	0.0		0.0	0.03	umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	HMDB	32340350
Human Urine	Detected and Quantified	0.002		0.0005	0.0038	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.024	0.007			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	22546835
Human Feces	Detected and Quantified	0.15	0.13			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	27624970
Human Feces	Detected and Quantified	0.19	0.22			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	27624970
Human Blood	Detected and Quantified	12.6		10.2	14.9	uM	Newborn (0-30 days old)		Normal	HMDB	25754623
Human Blood	Detected and Quantified	4.57		3.56	5.89	uM	Infant (0-1 year old)		Normal	HMDB	25754623
Human Blood	Detected and Quantified	5.14	1.50			uM	Adult (>18 years old)	Both	Normal	HMDB	28278231
Human Blood	Detected and Quantified	5.82	1.77			uM	Children (1-13 years old)	Both	Normal	HMDB	23108202
Human Blood	Detected and Quantified	6.13	2.55			uM	Adult (>18 years old)	Both	Normal	HMDB	21359215
Human Blood	Detected and Quantified	8.21	2.2			uM	Adult (>18 years old)	Both	Normal	HMDB	26010610
Human Blood	Detected and Quantified	8.39	0.98			uM	Adult (>18 years old)	Both	Normal	HMDB	21359215
Human Blood	Detected and Quantified	8.394	0.976			uM	Adult (>18 years old)	Both	Normal	HMDB	18953024
Human Urine	Detected and Quantified	0.0034	0.003			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	0.0037	0.0022			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Saliva	Detected and Quantified	0.034	0.0008			uM	Adult (>18 years old)	Both	Normal	HMDB	https://doi.org/10.1007/s11306-015-0840-5
Human Blood	Detected and Quantified			2.20	11.0	uM	Adult (>18 years old)	Both	Normal	HMDB	Molecular You (https://molecularyou.com)
Human All tissues	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB027546

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

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Sun JK, Sun F, Wang X, Yuan ST, Zheng SY, Mu XW: Risk factors and prognosis of hypoalbuminemia in surgical septic patients. PeerJ. 2015 Oct 1;3:e1267. doi: 10.7717/peerj.1267. eCollection 2015. [PubMed:26557421 ]
Wernly B, Lichtenauer M, Hoppe UC, Jung C: Hyperglycemia in septic patients: an essential stress survival response in all, a robust marker for risk stratification in some, to be messed with in none. J Thorac Dis. 2016 Jul;8(7):E621-4. doi: 10.21037/jtd.2016.05.24. [PubMed:27501420 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
Knuplez E, Marsche G: An Updated Review of Pro- and Anti-Inflammatory Properties of Plasma Lysophosphatidylcholines in the Vascular System. Int J Mol Sci. 2020 Jun 24;21(12). pii: ijms21124501. doi: 10.3390/ijms21124501. [PubMed:32599910 ]

Showing metabocard for LysoPC(20:4(5Z,8Z,11Z,14Z)) (MMDBc0034130)

MOL for #<Metabolite:0x00007fdb2a1668d8>

3D MOL for #<Metabolite:0x00007fdb2a1668d8>

3D SDF for #<Metabolite:0x00007fdb2a1668d8>

3D-SDF for #<Metabolite:0x00007fdb2a1668d8>

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INCHI for #<Metabolite:0x00007fdb2a1668d8>

Structure for #<Metabolite:0x00007fdb2a1668d8>

3D Structure for #<Metabolite:0x00007fdb2a1668d8>