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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (11) Show 11 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2009-10-22 15:43:18 UTC

Update Date

2022-07-14 16:57:35 UTC

HMDB ID

HMDB0013122

Secondary Accession Numbers

HMDB13122

Metabolite Identification

Common Name

LysoPC(P-18:0/0:0)

Description

LysoPC(P-18:0) 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(P-18:0), in particular, consists of one chain of plasmalogen 18:0 at the C-1 position. The plasmalogen 18:0 moiety is derived from animal fats, liver and kidney. 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. Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. 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. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids. 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 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652304052008232D          

 35 34  0  0  1  0            999 V2000
   18.2161   -5.2586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5108   -5.6658    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.8056   -5.2586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9212   -5.6658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1004   -5.6658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7557   -6.3542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6264   -5.2586    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   20.0336   -5.9638    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   19.2194   -4.5533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3317   -4.8514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0368   -5.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7420   -4.8513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4473   -5.2584    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   23.1525   -5.6656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0401   -5.9637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8544   -4.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3438   -6.4024    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.3834   -5.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6663   -5.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9492   -5.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2321   -5.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5151   -5.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7980   -5.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0809   -5.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3753   -5.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6582   -5.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9411   -5.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2240   -5.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5070   -5.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7895   -5.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0724   -5.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3549   -5.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6432   -5.2486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9261   -5.6564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2143   -5.2392    0.0000 C   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
  1  4  1  0  0  0  0
  3  5  1  0  0  0  0
  2  6  1  6  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
  2 17  1  1  0  0  0
 19 18  2  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 18  1  0  0  0  0
 26 25  1  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
 31 30  1  0  0  0  0
 32 31  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
M  CHG  2   8  -1  13   1
M  END

HMDB0013122
     RDKit          3D
LysoPC(P-18:0/0:0)
 88 87  0  0  0  0  0  0  0  0999 V2000
   10.7056   -0.1943    2.8159 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5294    0.1166    1.2956 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3059    1.5601    1.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1302    2.1965   -0.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9800    1.9124   -1.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8329    0.5200   -1.4686 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6290    0.4006   -2.4645 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3694    0.8196   -1.8275 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9345    0.0691   -0.6263 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6957   -1.3841   -0.7910 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6463   -1.7552   -1.7817 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2808   -1.2355   -1.5202 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7598   -1.7337   -0.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3612   -1.1797    0.0285 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8957   -1.7113    1.3701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4903   -1.1966    1.6448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4997    0.2706    1.6774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2720    0.9278    0.8019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0443    0.2652   -0.1127 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3635   -0.1629    0.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3171    0.9914    0.3819 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2634    1.8459   -0.7064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6874    0.3694    0.5495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9542   -0.3422   -0.6106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4375   -1.1084   -0.6147 P   0  0  0  0  0  5  0  0  0  0  0  0
   -7.7362   -1.5043   -2.0642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3255   -2.5567    0.2529 O   0  0  0  0  0  1  0  0  0  0  0  0
   -8.7042   -0.1557   -0.0931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5175   -0.7970    0.8363 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6510    0.0517    1.3038 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5337    0.4637    0.2317 N   0  0  0  0  0  4  0  0  0  0  0  0
  -12.6863    1.1021    0.8405 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0075   -0.6495   -0.5498 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8947    1.4735   -0.6177 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7673   -0.0199    3.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4815    0.4516    3.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0266   -1.2436    2.9333 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5475   -0.1822    0.8876 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8399   -0.6007    0.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1988    2.0893    1.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4771    1.8589    1.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2439    3.3467   -0.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0613    1.8848   -0.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9471    2.6476   -1.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0471    2.1328   -0.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7092    0.1797   -2.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4911   -0.1685   -0.6630 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9203    1.0784   -3.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6881   -0.6195   -2.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5510    0.7376   -2.5895 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4258    1.9033   -1.5930 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9890    0.5143   -0.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6810    0.2055    0.1852 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3797   -1.7772    0.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6261   -1.9634   -1.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9170   -1.4798   -2.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5746   -2.8806   -1.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1565   -0.1589   -1.6516 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6086   -1.7107   -2.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6525   -2.8379   -0.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4302   -1.4756    0.6547 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4233   -0.0809    0.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6947   -1.4545   -0.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8853   -2.8089    1.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5453   -1.3584    2.1940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8976   -1.5910    2.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1658   -1.5898    0.8438 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1167    0.7762    2.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2424    2.0091    0.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7144   -0.5693   -0.9133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4858   -0.9809    0.7952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0448    1.5390    1.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1290    1.8138   -1.2017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6081   -0.3648    1.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4629    1.0853    0.8170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9253   -1.7462    0.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8776   -1.0196    1.7163 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2913    0.9800    1.7998 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2546   -0.5133    2.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1819    1.8271    0.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4165    1.6614    1.7660 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4645    0.3667    1.1398 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2598   -0.8322   -1.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0858   -1.5181    0.1117 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0063   -0.4602   -1.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6523    2.1252   -1.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2733    2.1129    0.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3347    0.9903   -1.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 25 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  1  0
 31 34  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  0
  2 39  1  0
  3 40  1  0
  3 41  1  0
  4 42  1  0
  4 43  1  0
  5 44  1  0
  5 45  1  0
  6 46  1  0
  6 47  1  0
  7 48  1  0
  7 49  1  0
  8 50  1  0
  8 51  1  0
  9 52  1  0
  9 53  1  0
 10 54  1  0
 10 55  1  0
 11 56  1  0
 11 57  1  0
 12 58  1  0
 12 59  1  0
 13 60  1  0
 13 61  1  0
 14 62  1  0
 14 63  1  0
 15 64  1  0
 15 65  1  0
 16 66  1  0
 16 67  1  0
 17 68  1  0
 18 69  1  0
 20 70  1  0
 20 71  1  0
 21 72  1  1
 22 73  1  0
 23 74  1  0
 23 75  1  0
 29 76  1  0
 29 77  1  0
 30 78  1  0
 30 79  1  0
 32 80  1  0
 32 81  1  0
 32 82  1  0
 33 83  1  0
 33 84  1  0
 33 85  1  0
 34 86  1  0
 34 87  1  0
 34 88  1  0
M  CHG  2  27  -1  31   1
M  END


  Mrv1652304052008232D          

 35 34  0  0  1  0            999 V2000
   18.2161   -5.2586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5108   -5.6658    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.8056   -5.2586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9212   -5.6658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1004   -5.6658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7557   -6.3542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6264   -5.2586    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   20.0336   -5.9638    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   19.2194   -4.5533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3317   -4.8514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   21.7420   -4.8513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4473   -5.2584    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   23.1525   -5.6656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0401   -5.9637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8544   -4.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3438   -6.4024    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.3834   -5.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6663   -5.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9492   -5.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2321   -5.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5151   -5.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7980   -5.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0809   -5.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3753   -5.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6582   -5.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9411   -5.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2240   -5.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5070   -5.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7895   -5.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0724   -5.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3549   -5.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6432   -5.2486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9261   -5.6564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2143   -5.2392    0.0000 C   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
  1  4  1  0  0  0  0
  3  5  1  0  0  0  0
  2  6  1  6  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
  2 17  1  1  0  0  0
 19 18  2  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 18  1  0  0  0  0
 26 25  1  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
 31 30  1  0  0  0  0
 32 31  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
M  CHG  2   8  -1  13   1
M  END
> <DATABASE_ID>
HMDB0013122

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@](O)(CO\C=C/CCCCCCCCCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C26H54NO6P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-22-31-24-26(28)25-33-34(29,30)32-23-21-27(2,3)4/h20,22,26,28H,5-19,21,23-25H2,1-4H3/b22-20-/t26-/m1/s1

> <INCHI_KEY>
WBOMIOWRFSPZMC-AYICAFKVSA-N

> <FORMULA>
C26H54NO6P

> <MOLECULAR_WEIGHT>
507.6838

> <EXACT_MASS>
507.368874977

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
88

> <JCHEM_AVERAGE_POLARIZABILITY>
60.23337302010333

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{[(2R)-2-hydroxy-3-[(1Z)-octadec-1-en-1-yloxy]propyl phosphono]oxy}ethyl)trimethylazanium

> <ALOGPS_LOGP>
2.99

> <JCHEM_LOGP>
2.474654447861587

> <ALOGPS_LOGS>
-6.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.662760003722955

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8553408915809362

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4008756404462996

> <JCHEM_POLAR_SURFACE_AREA>
88.05

> <JCHEM_REFRACTIVITY>
151.8142

> <JCHEM_ROTATABLE_BOND_COUNT>
25

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.28e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-{[(2R)-2-hydroxy-3-[(1Z)-octadec-1-en-1-yloxy]propyl phosphono]oxy}ethyl)trimethylazanium

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013122
     RDKit          3D
LysoPC(P-18:0/0:0)
 88 87  0  0  0  0  0  0  0  0999 V2000
   10.7056   -0.1943    2.8159 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5294    0.1166    1.2956 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3059    1.5601    1.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1302    2.1965   -0.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9800    1.9124   -1.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8329    0.5200   -1.4686 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6290    0.4006   -2.4645 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3694    0.8196   -1.8275 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6957   -1.3841   -0.7910 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7598   -1.7337   -0.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3171    0.9914    0.3819 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2634    1.8459   -0.7064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6874    0.3694    0.5495 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.3255   -2.5567    0.2529 O   0  0  0  0  0  1  0  0  0  0  0  0
   -8.7042   -0.1557   -0.0931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5175   -0.7970    0.8363 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6510    0.0517    1.3038 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5337    0.4637    0.2317 N   0  0  0  0  0  4  0  0  0  0  0  0
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   11.4815    0.4516    3.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
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   11.5475   -0.1822    0.8876 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8399   -0.6007    0.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1988    2.0893    1.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4771    1.8589    1.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2439    3.3467   -0.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0613    1.8848   -0.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9471    2.6476   -1.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0471    2.1328   -0.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7092    0.1797   -2.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4911   -0.1685   -0.6630 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9203    1.0784   -3.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6881   -0.6195   -2.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5510    0.7376   -2.5895 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4258    1.9033   -1.5930 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9890    0.5143   -0.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6810    0.2055    0.1852 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3797   -1.7772    0.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6261   -1.9634   -1.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9170   -1.4798   -2.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5746   -2.8806   -1.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1565   -0.1589   -1.6516 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6086   -1.7107   -2.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6525   -2.8379   -0.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4302   -1.4756    0.6547 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4233   -0.0809    0.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6947   -1.4545   -0.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8853   -2.8089    1.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5453   -1.3584    2.1940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8976   -1.5910    2.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1658   -1.5898    0.8438 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1167    0.7762    2.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2424    2.0091    0.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7144   -0.5693   -0.9133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4858   -0.9809    0.7952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0448    1.5390    1.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1290    1.8138   -1.2017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6081   -0.3648    1.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4629    1.0853    0.8170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9253   -1.7462    0.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8776   -1.0196    1.7163 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2913    0.9800    1.7998 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2546   -0.5133    2.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1819    1.8271    0.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4165    1.6614    1.7660 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4645    0.3667    1.1398 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2598   -0.8322   -1.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0858   -1.5181    0.1117 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0063   -0.4602   -1.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6523    2.1252   -1.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2733    2.1129    0.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 25 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  1  0
 31 34  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  0
  2 39  1  0
  3 40  1  0
  3 41  1  0
  4 42  1  0
  4 43  1  0
  5 44  1  0
  5 45  1  0
  6 46  1  0
  6 47  1  0
  7 48  1  0
  7 49  1  0
  8 50  1  0
  8 51  1  0
  9 52  1  0
  9 53  1  0
 10 54  1  0
 10 55  1  0
 11 56  1  0
 11 57  1  0
 12 58  1  0
 12 59  1  0
 13 60  1  0
 13 61  1  0
 14 62  1  0
 14 63  1  0
 15 64  1  0
 15 65  1  0
 16 66  1  0
 16 67  1  0
 17 68  1  0
 18 69  1  0
 20 70  1  0
 20 71  1  0
 21 72  1  1
 22 73  1  0
 23 74  1  0
 23 75  1  0
 29 76  1  0
 29 77  1  0
 30 78  1  0
 30 79  1  0
 32 80  1  0
 32 81  1  0
 32 82  1  0
 33 83  1  0
 33 84  1  0
 33 85  1  0
 34 86  1  0
 34 87  1  0
 34 88  1  0
M  CHG  2  27  -1  31   1
M  END

HEADER    PROTEIN                                 05-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-APR-20         0                                  
HETATM    1  C   UNK     0      34.003  -9.816   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      32.687 -10.576   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      31.370  -9.816   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      35.320 -10.576   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      30.054 -10.576   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      31.277 -11.861   0.000  0.00  0.00           O+0
HETATM    7  P   UNK     0      36.636  -9.816   0.000  0.00  0.00           P+0
HETATM    8  O   UNK     0      37.396 -11.132   0.000  0.00  0.00           O-1
HETATM    9  O   UNK     0      35.876  -8.499   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      37.953  -9.056   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      39.269  -9.816   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      40.585  -9.056   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      41.902  -9.816   0.000  0.00  0.00           N+1
HETATM   14  C   UNK     0      43.218 -10.576   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      41.142 -11.132   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      42.662  -8.499   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0      34.242 -11.951   0.000  0.00  0.00           H+0
HETATM   18  C   UNK     0      28.716  -9.814   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      27.377  -9.814   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      26.039 -10.576   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      24.700  -9.814   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      23.362 -10.576   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      22.023  -9.814   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      20.684 -10.576   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      19.367  -9.814   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      18.029 -10.576   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      16.690  -9.814   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.351 -10.576   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.013  -9.814   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.674 -10.576   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.335  -9.814   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.996 -10.576   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.667  -9.797   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.329 -10.559   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.000  -9.780   0.000  0.00  0.00           C+0
CONECT    1    2    4                                                       
CONECT    2    1    3    6   17                                             
CONECT    3    2    5                                                       
CONECT    4    1    7                                                       
CONECT    5    3   18                                                       
CONECT    6    2                                                            
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   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13                                                            
CONECT   17    2                                                            
CONECT   18   19    5                                                       
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   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   68    0
END

COMPND    HMDB0013122
HETATM    1  C1  UNL     1      10.706  -0.194   2.816  1.00  0.00           C  
HETATM    2  C2  UNL     1      10.529   0.117   1.296  1.00  0.00           C  
HETATM    3  C3  UNL     1      10.306   1.560   1.144  1.00  0.00           C  
HETATM    4  C4  UNL     1      10.130   2.196  -0.153  1.00  0.00           C  
HETATM    5  C5  UNL     1       8.980   1.912  -1.021  1.00  0.00           C  
HETATM    6  C6  UNL     1       8.833   0.520  -1.469  1.00  0.00           C  
HETATM    7  C7  UNL     1       7.629   0.401  -2.465  1.00  0.00           C  
HETATM    8  C8  UNL     1       6.369   0.820  -1.828  1.00  0.00           C  
HETATM    9  C9  UNL     1       5.934   0.069  -0.626  1.00  0.00           C  
HETATM   10  C10 UNL     1       5.696  -1.384  -0.791  1.00  0.00           C  
HETATM   11  C11 UNL     1       4.646  -1.755  -1.782  1.00  0.00           C  
HETATM   12  C12 UNL     1       3.281  -1.236  -1.520  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.760  -1.734  -0.191  1.00  0.00           C  
HETATM   14  C14 UNL     1       1.361  -1.180   0.029  1.00  0.00           C  
HETATM   15  C15 UNL     1       0.896  -1.711   1.370  1.00  0.00           C  
HETATM   16  C16 UNL     1      -0.490  -1.197   1.645  1.00  0.00           C  
HETATM   17  C17 UNL     1      -0.500   0.271   1.677  1.00  0.00           C  
HETATM   18  C18 UNL     1      -1.272   0.928   0.802  1.00  0.00           C  
HETATM   19  O1  UNL     1      -2.044   0.265  -0.113  1.00  0.00           O  
HETATM   20  C19 UNL     1      -3.363  -0.163   0.078  1.00  0.00           C  
HETATM   21  C20 UNL     1      -4.317   0.991   0.382  1.00  0.00           C  
HETATM   22  O2  UNL     1      -4.263   1.846  -0.706  1.00  0.00           O  
HETATM   23  C21 UNL     1      -5.687   0.369   0.549  1.00  0.00           C  
HETATM   24  O3  UNL     1      -5.954  -0.342  -0.611  1.00  0.00           O  
HETATM   25  P1  UNL     1      -7.438  -1.108  -0.615  1.00  0.00           P  
HETATM   26  O4  UNL     1      -7.736  -1.504  -2.064  1.00  0.00           O  
HETATM   27  O5  UNL     1      -7.326  -2.557   0.253  1.00  0.00           O1-
HETATM   28  O6  UNL     1      -8.704  -0.156  -0.093  1.00  0.00           O  
HETATM   29  C22 UNL     1      -9.518  -0.797   0.836  1.00  0.00           C  
HETATM   30  C23 UNL     1     -10.651   0.052   1.304  1.00  0.00           C  
HETATM   31  N1  UNL     1     -11.534   0.464   0.232  1.00  0.00           N1+
HETATM   32  C24 UNL     1     -12.686   1.102   0.840  1.00  0.00           C  
HETATM   33  C25 UNL     1     -12.007  -0.650  -0.550  1.00  0.00           C  
HETATM   34  C26 UNL     1     -10.895   1.474  -0.618  1.00  0.00           C  
HETATM   35  H1  UNL     1       9.767  -0.020   3.350  1.00  0.00           H  
HETATM   36  H2  UNL     1      11.482   0.452   3.246  1.00  0.00           H  
HETATM   37  H3  UNL     1      11.027  -1.244   2.933  1.00  0.00           H  
HETATM   38  H4  UNL     1      11.547  -0.182   0.888  1.00  0.00           H  
HETATM   39  H5  UNL     1       9.840  -0.601   0.898  1.00  0.00           H  
HETATM   40  H6  UNL     1      11.199   2.089   1.646  1.00  0.00           H  
HETATM   41  H7  UNL     1       9.477   1.859   1.887  1.00  0.00           H  
HETATM   42  H8  UNL     1      10.244   3.347  -0.055  1.00  0.00           H  
HETATM   43  H9  UNL     1      11.061   1.885  -0.777  1.00  0.00           H  
HETATM   44  H10 UNL     1       8.947   2.648  -1.882  1.00  0.00           H  
HETATM   45  H11 UNL     1       8.047   2.133  -0.385  1.00  0.00           H  
HETATM   46  H12 UNL     1       9.709   0.180  -2.033  1.00  0.00           H  
HETATM   47  H13 UNL     1       8.491  -0.168  -0.663  1.00  0.00           H  
HETATM   48  H14 UNL     1       7.920   1.078  -3.292  1.00  0.00           H  
HETATM   49  H15 UNL     1       7.688  -0.620  -2.826  1.00  0.00           H  
HETATM   50  H16 UNL     1       5.551   0.738  -2.589  1.00  0.00           H  
HETATM   51  H17 UNL     1       6.426   1.903  -1.593  1.00  0.00           H  
HETATM   52  H18 UNL     1       4.989   0.514  -0.213  1.00  0.00           H  
HETATM   53  H19 UNL     1       6.681   0.206   0.185  1.00  0.00           H  
HETATM   54  H20 UNL     1       5.380  -1.777   0.200  1.00  0.00           H  
HETATM   55  H21 UNL     1       6.626  -1.963  -1.027  1.00  0.00           H  
HETATM   56  H22 UNL     1       4.917  -1.480  -2.833  1.00  0.00           H  
HETATM   57  H23 UNL     1       4.575  -2.881  -1.807  1.00  0.00           H  
HETATM   58  H24 UNL     1       3.157  -0.159  -1.652  1.00  0.00           H  
HETATM   59  H25 UNL     1       2.609  -1.711  -2.296  1.00  0.00           H  
HETATM   60  H26 UNL     1       2.653  -2.838  -0.185  1.00  0.00           H  
HETATM   61  H27 UNL     1       3.430  -1.476   0.655  1.00  0.00           H  
HETATM   62  H28 UNL     1       1.423  -0.081   0.109  1.00  0.00           H  
HETATM   63  H29 UNL     1       0.695  -1.455  -0.786  1.00  0.00           H  
HETATM   64  H30 UNL     1       0.885  -2.809   1.418  1.00  0.00           H  
HETATM   65  H31 UNL     1       1.545  -1.358   2.194  1.00  0.00           H  
HETATM   66  H32 UNL     1      -0.898  -1.591   2.597  1.00  0.00           H  
HETATM   67  H33 UNL     1      -1.166  -1.590   0.844  1.00  0.00           H  
HETATM   68  H34 UNL     1       0.117   0.776   2.407  1.00  0.00           H  
HETATM   69  H35 UNL     1      -1.242   2.009   0.868  1.00  0.00           H  
HETATM   70  H36 UNL     1      -3.714  -0.569  -0.913  1.00  0.00           H  
HETATM   71  H37 UNL     1      -3.486  -0.981   0.795  1.00  0.00           H  
HETATM   72  H38 UNL     1      -4.045   1.539   1.285  1.00  0.00           H  
HETATM   73  H39 UNL     1      -5.129   1.814  -1.202  1.00  0.00           H  
HETATM   74  H40 UNL     1      -5.608  -0.365   1.379  1.00  0.00           H  
HETATM   75  H41 UNL     1      -6.463   1.085   0.817  1.00  0.00           H  
HETATM   76  H42 UNL     1      -9.925  -1.746   0.437  1.00  0.00           H  
HETATM   77  H43 UNL     1      -8.878  -1.020   1.716  1.00  0.00           H  
HETATM   78  H44 UNL     1     -10.291   0.980   1.800  1.00  0.00           H  
HETATM   79  H45 UNL     1     -11.255  -0.513   2.033  1.00  0.00           H  
HETATM   80  H46 UNL     1     -13.182   1.827   0.167  1.00  0.00           H  
HETATM   81  H47 UNL     1     -12.417   1.661   1.766  1.00  0.00           H  
HETATM   82  H48 UNL     1     -13.465   0.367   1.140  1.00  0.00           H  
HETATM   83  H49 UNL     1     -11.260  -0.832  -1.360  1.00  0.00           H  
HETATM   84  H50 UNL     1     -12.086  -1.518   0.112  1.00  0.00           H  
HETATM   85  H51 UNL     1     -13.006  -0.460  -1.005  1.00  0.00           H  
HETATM   86  H52 UNL     1     -11.652   2.125  -1.099  1.00  0.00           H  
HETATM   87  H53 UNL     1     -10.273   2.113   0.027  1.00  0.00           H  
HETATM   88  H54 UNL     1     -10.335   0.990  -1.441  1.00  0.00           H  
CONECT    1    2   35   36   37
CONECT    2    3   38   39
CONECT    3    4   40   41
CONECT    4    5   42   43
CONECT    5    6   44   45
CONECT    6    7   46   47
CONECT    7    8   48   49
CONECT    8    9   50   51
CONECT    9   10   52   53
CONECT   10   11   54   55
CONECT   11   12   56   57
CONECT   12   13   58   59
CONECT   13   14   60   61
CONECT   14   15   62   63
CONECT   15   16   64   65
CONECT   16   17   66   67
CONECT   17   18   18   68
CONECT   18   19   69
CONECT   19   20
CONECT   20   21   70   71
CONECT   21   22   23   72
CONECT   22   73
CONECT   23   24   74   75
CONECT   24   25
CONECT   25   26   26   27   28
CONECT   28   29
CONECT   29   30   76   77
CONECT   30   31   78   79
CONECT   31   32   33   34
CONECT   32   80   81   82
CONECT   33   83   84   85
CONECT   34   86   87   88
END

HMDB0013122
     RDKit          3D
LysoPC(P-18:0/0:0)
 88 87  0  0  0  0  0  0  0  0999 V2000
   10.7056   -0.1943    2.8159 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5294    0.1166    1.2956 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3059    1.5601    1.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1302    2.1965   -0.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9800    1.9124   -1.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8329    0.5200   -1.4686 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6290    0.4006   -2.4645 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3694    0.8196   -1.8275 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9345    0.0691   -0.6263 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6957   -1.3841   -0.7910 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6463   -1.7552   -1.7817 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2808   -1.2355   -1.5202 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7598   -1.7337   -0.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3612   -1.1797    0.0285 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8957   -1.7113    1.3701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4903   -1.1966    1.6448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4997    0.2706    1.6774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2720    0.9278    0.8019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0443    0.2652   -0.1127 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3635   -0.1629    0.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3171    0.9914    0.3819 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2634    1.8459   -0.7064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6874    0.3694    0.5495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9542   -0.3422   -0.6106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4375   -1.1084   -0.6147 P   0  0  0  0  0  5  0  0  0  0  0  0
   -7.7362   -1.5043   -2.0642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3255   -2.5567    0.2529 O   0  0  0  0  0  1  0  0  0  0  0  0
   -8.7042   -0.1557   -0.0931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5175   -0.7970    0.8363 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6510    0.0517    1.3038 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5337    0.4637    0.2317 N   0  0  0  0  0  4  0  0  0  0  0  0
  -12.6863    1.1021    0.8405 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0075   -0.6495   -0.5498 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8947    1.4735   -0.6177 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7673   -0.0199    3.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4815    0.4516    3.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0266   -1.2436    2.9333 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5475   -0.1822    0.8876 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8399   -0.6007    0.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1988    2.0893    1.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4771    1.8589    1.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2439    3.3467   -0.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0613    1.8848   -0.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9471    2.6476   -1.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0471    2.1328   -0.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7092    0.1797   -2.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4911   -0.1685   -0.6630 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9203    1.0784   -3.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6881   -0.6195   -2.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5510    0.7376   -2.5895 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4258    1.9033   -1.5930 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9890    0.5143   -0.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6810    0.2055    0.1852 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3797   -1.7772    0.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6261   -1.9634   -1.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9170   -1.4798   -2.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5746   -2.8806   -1.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1565   -0.1589   -1.6516 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6086   -1.7107   -2.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6525   -2.8379   -0.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4302   -1.4756    0.6547 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4233   -0.0809    0.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6947   -1.4545   -0.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8853   -2.8089    1.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5453   -1.3584    2.1940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8976   -1.5910    2.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1658   -1.5898    0.8438 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1167    0.7762    2.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2424    2.0091    0.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7144   -0.5693   -0.9133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4858   -0.9809    0.7952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0448    1.5390    1.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1290    1.8138   -1.2017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6081   -0.3648    1.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4629    1.0853    0.8170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9253   -1.7462    0.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8776   -1.0196    1.7163 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2913    0.9800    1.7998 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2546   -0.5133    2.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1819    1.8271    0.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4165    1.6614    1.7660 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4645    0.3667    1.1398 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2598   -0.8322   -1.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0858   -1.5181    0.1117 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0063   -0.4602   -1.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6523    2.1252   -1.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2733    2.1129    0.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3347    0.9903   -1.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 25 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  1  0
 31 34  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  0
  2 39  1  0
  3 40  1  0
  3 41  1  0
  4 42  1  0
  4 43  1  0
  5 44  1  0
  5 45  1  0
  6 46  1  0
  6 47  1  0
  7 48  1  0
  7 49  1  0
  8 50  1  0
  8 51  1  0
  9 52  1  0
  9 53  1  0
 10 54  1  0
 10 55  1  0
 11 56  1  0
 11 57  1  0
 12 58  1  0
 12 59  1  0
 13 60  1  0
 13 61  1  0
 14 62  1  0
 14 63  1  0
 15 64  1  0
 15 65  1  0
 16 66  1  0
 16 67  1  0
 17 68  1  0
 18 69  1  0
 20 70  1  0
 20 71  1  0
 21 72  1  1
 22 73  1  0
 23 74  1  0
 23 75  1  0
 29 76  1  0
 29 77  1  0
 30 78  1  0
 30 79  1  0
 32 80  1  0
 32 81  1  0
 32 82  1  0
 33 83  1  0
 33 84  1  0
 33 85  1  0
 34 86  1  0
 34 87  1  0
 34 88  1  0
M  CHG  2  27  -1  31   1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(1-Enyl-stearoyl)-glycero-3-phosphocholine	ChEBI
1-(1-Enyl-stearoyl)-GPC	ChEBI
1-(1-Enyl-stearoyl)-GPC (p-18:0)	ChEBI
GPC(p-18:0)	ChEBI
GPC(p-18:0/0:0)	ChEBI
LysoPC(p-18:0)	ChEBI
PC(p-18:0/0:0)	ChEBI
1-(1Z-Octadecenyl)-GPC	HMDB
1-(1Z-Octadecenyl)-lysophosphatidylcholine	HMDB
1-(1Z-Octadecenyl)-sn-glycero-3-phosphocholine	HMDB
GPC(18:1)	HMDB
GPC(O-18:1(1Z))	HMDB
GPC(O-18:1(1Z)/0:0)	HMDB
LPC(18:1)	HMDB
LPC(O-18:1(1Z))	HMDB
LPC(O-18:1(1Z)/0:0)	HMDB
LPC(p-18:0)	HMDB
LPC(p-18:0/0:0)	HMDB
LysoPC(18:1)	HMDB
LysoPC(O-18:1(1Z))	HMDB
LysoPC(O-18:1(1Z)/0:0)	HMDB
Lysophosphatidylcholine(18:1)	HMDB
Lysophosphatidylcholine(O-18:1(1Z))	HMDB
Lysophosphatidylcholine(O-18:1(1Z)/0:0)	HMDB
Lysophosphatidylcholine(p-18:0)	HMDB
Lysophosphatidylcholine(p-18:0/0:0)	HMDB

Chemical Formula

C₂₆H₅₄NO₆P

Average Molecular Weight

507.6838

Monoisotopic Molecular Weight

507.368874977

IUPAC Name

(2-{[(2R)-2-hydroxy-3-[(1Z)-octadec-1-en-1-yloxy]propyl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-2-hydroxy-3-[(1Z)-octadec-1-en-1-yloxy]propyl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCC\C=C/OC[C@](O)([H])COP([O-])(=O)OCC[N+](C)(C)C

InChI Identifier

InChI=1S/C26H54NO6P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-22-31-24-26(28)25-33-34(29,30)32-23-21-27(2,3)4/h20,22,26,28H,5-19,21,23-25H2,1-4H3/b22-20-/t26-/m1/s1

InChI Key

WBOMIOWRFSPZMC-AYICAFKVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-(1z-alkenyl)-glycero-3-phosphocholines. These are glycerophosphocholines that carry exactly one 1Z-alkenyl chain attached at the O1 position of a glycerol moiety through an ether linkage.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphocholines

Direct Parent

1-(1Z-alkenyl)-glycero-3-phosphocholines

Alternative Parents

Substituents

1-(1z-alkenyl)-glycero-3-phosphocholine
Phosphocholine
Glycerol vinyl ether
Dialkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Quaternary ammonium salt
Tetraalkylammonium salt
Secondary alcohol
Alcohol
Organic salt
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

1Z-alkenylglycerophosphocholines (LMGP01070009 )

Ontology

Physiological effect

Health effect

Nervous system disorder

Central nervous system disorder

Alzheimer's Disease (PMID: 30845751)

Renal system and urinary system

Renal disorder

Renal failure (PMID: 30845751)
Renal cell carcinoma (PMID: 26162894)

Cancer

Ovarian cancer (PMID: 30845751)
Colorectal cancer (PMID: 26162894)

Digestive system disorder

Gastrointestinal disorder

Stomach cancer (PMID: 26162894)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 18953024)
Cerebrospinal Fluid (CSF) (PMID: 22546835)

Cellular substructure

Cell

All cells and tissues (HMDB: HMDB0013122)

Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Naturally occurring process

Biological process

Cellular process

Apoptosis (PMID: 30845751)

Biochemical pathway

Signaling pathway

Apoptosis (PMID: 30845751)

Role

Industrial application

Pharmaceutical industry

Biomarker

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	236.8	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001983

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00023 g/L	ALOGPS
logP	2.99	ALOGPS
logP	2.47	ChemAxon
logS	-6.4	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	88.05 Å²	ChemAxon
Rotatable Bond Count	25	ChemAxon
Refractivity	151.81 m³·mol⁻¹	ChemAxon
Polarizability	60.23 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	241.578	30932474
DeepCCS	[M-H]-	238.748	30932474
DeepCCS	[M-2H]-	272.572	30932474
DeepCCS	[M+Na]+	249.076	30932474
AllCCS	[M+H]+	237.8	32859911
AllCCS	[M+H-H2O]+	236.5	32859911
AllCCS	[M+NH4]+	239.0	32859911
AllCCS	[M+Na]+	239.4	32859911
AllCCS	[M-H]-	232.5	32859911
AllCCS	[M+Na-2H]-	235.1	32859911
AllCCS	[M+HCOO]-	238.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
LysoPC(P-18:0/0:0)	CCCCCCCCCCCCCCCC\C=C/OC[C@](O)([H])COP([O-])(=O)OCC[N+](C)(C)C	3669.9	Standard polar	33892256
LysoPC(P-18:0/0:0)	CCCCCCCCCCCCCCCC\C=C/OC[C@](O)([H])COP([O-])(=O)OCC[N+](C)(C)C	3149.6	Standard non polar	33892256
LysoPC(P-18:0/0:0)	CCCCCCCCCCCCCCCC\C=C/OC[C@](O)([H])COP([O-])(=O)OCC[N+](C)(C)C	3450.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
LysoPC(P-18:0/0:0),1TMS,isomer #1	CCCCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O[Si](C)(C)C	3390.5	Semi standard non polar	33892256
LysoPC(P-18:0/0:0),1TBDMS,isomer #1	CCCCCCCCCCCCCCCC/C=C\OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C	3618.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - LysoPC(P-18:0/0:0) GC-MS (Non-derivatized) - 70eV, Positive	splash10-008a-6920100000-2df8be314922263b1bc0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - LysoPC(P-18:0/0:0) GC-MS (1 TMS) - 70eV, Positive	splash10-03l0-9410010000-1d20a22a13ca01abd059	2017-10-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(P-18:0/0:0) 10V, Positive-QTOF	splash10-052r-9123230000-e17bb36494233d497e0c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(P-18:0/0:0) 20V, Positive-QTOF	splash10-0zj0-9565100000-75f3d6080f083fc1a9ae	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(P-18:0/0:0) 40V, Positive-QTOF	splash10-0f80-9241000000-38f0283afebd2319b528	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(P-18:0/0:0) 10V, Negative-QTOF	splash10-0a4i-0060390000-b105c65eb62b72b82bc8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(P-18:0/0:0) 20V, Negative-QTOF	splash10-0gi9-1190510000-b3abc9f4d737a57e0411	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(P-18:0/0:0) 40V, Negative-QTOF	splash10-00or-7290000000-1b0b8f7bce7495d468e6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(P-18:0/0:0) 10V, Positive-QTOF	splash10-0kal-0930040000-09ff1b2712b975180fc0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(P-18:0/0:0) 20V, Positive-QTOF	splash10-0006-1430910000-d617ca248c1dc01b3a19	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(P-18:0/0:0) 40V, Positive-QTOF	splash10-000x-1970810000-c8f2d1f919c9f6882e25	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(P-18:0/0:0) 10V, Negative-QTOF	splash10-0a4i-0000090000-3ffc6e622fbd21ae939d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(P-18:0/0:0) 20V, Negative-QTOF	splash10-0a4i-0020390000-9a85c5568263cd3b906e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(P-18:0/0:0) 40V, Negative-QTOF	splash10-004i-9230000000-01da00770b9a352e1767	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(P-18:0/0:0) 10V, Negative-QTOF	splash10-0006-0000090000-cc32c697f7268040b00b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(P-18:0/0:0) 20V, Negative-QTOF	splash10-0006-0110910000-3654734ab6fa1a06a347	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(P-18:0/0:0) 40V, Negative-QTOF	splash10-0fdo-0140910000-69c99f97ee0ee932c371	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.067 (0 - 0.134) uM	Adult (>18 years old)	Both	Normal	18953024	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.069 +/- 0.019 uM	Adult (>18 years old)	Not Specified	Normal	22546835	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029295

KNApSAcK ID

Not Available

Chemspider ID

24823061

KEGG Compound ID

C04230

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24779527

PDB ID

Not Available

ChEBI ID

133662

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
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 ]
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 ]
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 ]
Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Cytosolic phospholipase A2

General function:: Involved in metabolic process
Specific function:: Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response.
Gene Name:: PLA2G4A
Uniprot ID:: P47712
Molecular weight:: 85210.19

Enzyme Details

2. Phosphatidylcholine-sterol acyltransferase

General function:: Involved in phosphatidylcholine-sterol O-acyltransferase activity
Specific function:: Central enzyme in the extracellular metabolism of plasma lipoproteins. Synthesized mainly in the liver and secreted into plasma where it converts cholesterol and phosphatidylcholines (lecithins) to cholesteryl esters and lysophosphatidylcholines on the surface of high and low density lipoproteins (HDLs and LDLs). The cholesterol ester is then transported back to the liver. Has a preference for plasma 16:0-18:2 or 18:O-18:2 phosphatidylcholines. Also produced in the brain by primary astrocytes, and esterifies free cholesterol on nascent APOE-containing lipoproteins secreted from glia and influences cerebral spinal fluid (CSF) APOE- and APOA1 levels. Together with APOE and the cholesterol transporter ABCA1, plays a key role in the maturation of glial-derived, nascent lipoproteins. Required for remodeling high-density lipoprotein particles into their spherical forms.
Gene Name:: LCAT
Uniprot ID:: P04180
Molecular weight:: 49577.545

Enzyme Details

3. Eosinophil lysophospholipase

General function:: Involved in sugar binding
Specific function:: May have both lysophospholipase and carbohydrate-binding activities.
Gene Name:: CLC
Uniprot ID:: Q05315
Molecular weight:: 16452.785

Enzyme Details

4. Free fatty acid receptor 1

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Receptor for medium and long chain saturated and unsaturated fatty acids. Binding of the ligand increase intracellular calcium concentration and amplify glucose-stimulated insulin secretion. The activity of this receptor is mediated by G- proteins that activate phospholipase C. Seems to act through a G(q) and G(i)-mediated pathway
Gene Name:: FFAR1
Uniprot ID:: O14842
Molecular weight:: 31456.6

Enzyme Details

5. Lysophospholipid acyltransferase 5

General function:: Involved in 1-acylglycerophosphocholine O-acyltransfera
Specific function:: Acyltransferase which mediates the conversion of lysophosphatidylcholine (1-acyl-sn-glycero-3-phosphocholine or LPC) into phosphatidylcholine (1,2-diacyl-sn-glycero-3-phosphocholine or PC) (LPCAT activity). Catalyzes also the conversion of lysophosphatidylserine (1-acyl-2-hydroxy-sn-glycero-3-phospho-L-serine or LPS) into phosphatidylserine (1,2-diacyl-sn-glycero-3-phospho-L-serine or PS) (LPSAT activity). Has also weak lysophosphatidylethanolamine acyltransferase activity (LPEAT activity). Favors polyunsaturated fatty acyl-CoAs as acyl donors compared to saturated fatty acyl-CoAs. Seems to be the major enzyme contributing to LPCAT activity in the liver. Lysophospholipid acyltransferases (LPLATs) catalyze the reacylation step of the phospholipid remodeling pathway also known as the Lands cycle.
Gene Name:: LPCAT3
Uniprot ID:: Q6P1A2
Molecular weight:: 56034.48

Enzyme Details

6. Lysophosphatidylcholine acyltransferase 1

General function:: Involved in acyltransferase activity
Specific function:: Possesses both acyltransferase and acetyltransferase activities. Activity is calcium-independent. Mediates the conversion of 1-acyl-sn-glycero-3-phosphocholine (LPC) into phosphatidylcholine (PC). Displays a clear preference for saturated fatty acyl-CoAs, and 1-myristoyl or 1-palmitoyl LPC as acyl donors and acceptors, respectively. May synthesize phosphatidylcholine in pulmonary surfactant, thereby playing a pivotal role in respiratory physiology.
Gene Name:: LPCAT1
Uniprot ID:: Q8NF37
Molecular weight:: 59150.675

Enzyme Details

7. Lysophosphatidylcholine acyltransferase 2

General function:: Involved in acyltransferase activity
Specific function:: Possesses both acyltransferase and acetyltransferase activities. Activity is calcium-dependent. Involved in platelet-activating factor (PAF) biosynthesis by catalyzing the conversion of the PAF precursor, 1-O-alkyl-sn-glycero-3-phosphocholine (lyso-PAF) into 1-O-alkyl-2-acetyl-sn-glycero-3-phosphocholine (PAF). Also converts lyso-PAF to 1-alkyl-phosphatidylcholine (PC), a major component of cell membranes and a PAF precursor. Under resting conditions, acyltransferase activity is preferred. Upon acute inflammatory stimulus, acetyltransferase activity is enhanced and PAF synthesis increases (By similarity).
Gene Name:: LPCAT2
Uniprot ID:: Q7L5N7
Molecular weight:: 60207.295

Enzyme Details

8. Phospholipase B1, membrane-associated

General function:: Involved in hydrolase activity
Specific function:: Membrane-associated phospholipase. Exhibits a calcium-independent broad substrate specificity including phospholipase A2/lysophospholipase activity. Preferential hydrolysis at the sn-2 position of diacylphospholipids and diacyglycerol, whereas it shows no positional specificity toward triacylglycerol. Exhibits also esterase activity toward p-nitrophenyl. May act on the brush border membrane to facilitate the absorption of digested lipids (By similarity).
Gene Name:: PLB1
Uniprot ID:: Q6P1J6
Molecular weight:: 161711.9

Enzyme Details

9. Glucose-dependent insulinotropic receptor

General function:: Not Available
Specific function:: Receptor for the endogenous fatty-acid ethanolamide oleoylethanolamide (OEA) and lysophosphatidylcholine (LPC). Functions as a glucose-dependent insulinotropic receptor. The activity of this receptor is mediated by G proteins which activate adenylate cyclase. Seems to act through a G(s) mediated pathway.
Gene Name:: GPR119
Uniprot ID:: Q8TDV5
Molecular weight:: 36888.36

Enzyme Details

10. G-protein coupled receptor 55

General function:: Not Available
Specific function:: May be involved in hyperalgesia associated with inflammatory and neuropathic pain. Receptor for L-alpha-lysophosphatidylinositol (LPI). LPI induces Ca2+ release from intracellular stores via the heterotrimeric G protein GNA13 and RHOA. Putative cannabinoid receptor. May play a role in bone physiology by regulating osteoclast number and function.
Gene Name:: GPR55
Uniprot ID:: Q9Y2T6
Molecular weight:: 36.0

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters

Showing metabocard for LysoPC(P-18:0/0:0) (HMDB0013122)

MOL for HMDB0013122 (LysoPC(P-18:0/0:0))

3D MOL for HMDB0013122 (LysoPC(P-18:0/0:0))

3D SDF for HMDB0013122 (LysoPC(P-18:0/0:0))

3D-SDF for HMDB0013122 (LysoPC(P-18:0/0:0))

PDB for HMDB0013122 (LysoPC(P-18:0/0:0))

3D PDB for HMDB0013122 (LysoPC(P-18:0/0:0))

SMILES for HMDB0013122 (LysoPC(P-18:0/0:0))

INCHI for HMDB0013122 (LysoPC(P-18:0/0:0))

Structure for HMDB0013122 (LysoPC(P-18:0/0:0))

3D Structure for HMDB0013122 (LysoPC(P-18:0/0:0))

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes