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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (29) Show 29 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2008-09-16 13:20:13 UTC

Update Date

2022-07-14 16:57:35 UTC

HMDB ID

HMDB0010399

Secondary Accession Numbers

HMDB10399

Metabolite Identification

Common Name

LysoPC(22:1(13Z)/0:0)

Description

LysoPC(22:1(13Z)) 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(22:1(13Z)), in particular, consists of one chain of erucic acid at the C-1 position. The erucic acid moiety is derived from seed oils and avocados. 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 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652304202020522D          

 40 39  0  0  1  0            999 V2000
   22.6529   -2.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9477   -3.3880    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   21.2425   -2.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3581   -3.3880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5373   -3.3880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0632   -2.9809    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   24.4704   -3.6860    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   23.6561   -2.2757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7684   -2.5737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4736   -2.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1788   -2.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8840   -2.9809    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   26.4768   -3.6860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5366   -2.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5891   -3.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8188   -2.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5333   -3.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2478   -2.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9623   -3.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6768   -2.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3913   -3.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1057   -2.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8202   -3.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5347   -2.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2491   -2.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9637   -3.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6781   -2.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3926   -3.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1071   -2.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8215   -3.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5360   -2.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2505   -3.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9649   -2.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6795   -3.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3939   -2.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1084   -3.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8229   -2.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8229   -2.1505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8350   -3.9090    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.3029   -4.0170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  1  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  6  9  1  0  0  0  0
  9 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
 12 14  1  0  0  0  0
 12 15  1  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  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 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
 29 30  1  0  0  0  0
 30 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
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37  5  1  0  0  0  0
 37 38  2  0  0  0  0
  2 39  1  1  0  0  0
  2 40  1  6  0  0  0
M  CHG  2   7  -1  12   1
M  END

HMDB0010399
     RDKit          3D
LysoPC(22:1(13Z)/0:0)
 99 98  0  0  0  0  0  0  0  0999 V2000
    9.3675   -3.7794    1.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2199   -3.3856    2.3048 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6014   -2.1485    3.1234 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8862   -1.0455    2.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2685    0.1590    2.8117 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6891    1.4087    2.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9567    2.2617    1.3007 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6216    1.9782   -0.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8262    0.8788   -0.5411 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6517    1.0054   -1.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0468    2.3266   -1.4013 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8654    2.5271   -2.8951 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9753    1.5126   -3.5394 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5573    1.5051   -3.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8908    2.8239   -3.2364 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4882    2.9233   -2.7534 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6175    1.9140   -3.4195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8095    2.0056   -2.9822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0188    1.8148   -1.5237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5744    0.5174   -0.9539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2220   -0.6997   -1.5213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6819   -0.6161   -1.3053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3816   -0.0488   -2.1749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2331   -1.1554   -0.1717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6180   -1.1339    0.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3679   -1.9033   -0.9176 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9405   -3.2466   -0.9348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8569   -1.8654   -0.7589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3230   -0.5561   -0.7396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9917   -0.4819   -0.5627 P   0  0  0  0  0  5  0  0  0  0  0  0
   -9.3901    0.9691   -0.8437 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7889   -1.5601   -1.5870 O   0  0  0  0  0  1  0  0  0  0  0  0
   -9.3956   -0.8296    1.0218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9667    0.2236    1.6926 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2846   -0.2017    3.1006 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1907   -1.2991    3.2101 N   0  0  0  0  0  4  0  0  0  0  0  0
  -11.8118   -1.2090    4.5403 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5684   -2.6030    3.1339 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1947   -1.2536    2.1743 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3084   -3.1808    0.4477 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3421   -3.6157    1.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2353   -4.8338    1.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3470   -3.1608    1.6501 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9826   -4.2418    2.9480 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5314   -2.3345    3.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7952   -1.8300    3.7836 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6547   -1.4142    1.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8639   -0.9379    1.6062 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1253   -0.1801    3.5238 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4386    0.3332    3.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7335    1.1827    1.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0856    2.0537    3.1155 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5755    3.2569    1.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0204    2.7089    1.8404 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6782    1.8207   -0.6107 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3156    2.9071   -0.6578 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2070   -0.1734   -0.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1392    0.0742   -1.4484 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9737    2.2484   -1.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4663    3.1704   -0.8796 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8691    2.4153   -3.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5489    3.5578   -3.0590 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0079    1.6632   -4.6391 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4364    0.4959   -3.3640 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0406    0.6825   -3.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5640    1.2227   -1.9568 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8871    3.0430   -4.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4861    3.5881   -2.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4260    2.9180   -1.6447 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1076    3.9402   -3.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6477    2.1389   -4.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0150    0.8689   -3.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4757    1.3789   -3.6161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1308    3.0678   -3.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0886    2.0390   -1.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4607    2.6240   -0.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5319    0.4598   -1.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8062    0.5398    0.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0549   -0.8337   -2.6065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7996   -1.6254   -1.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9893   -0.0906    0.1426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7436   -1.5479    1.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1331   -1.5113   -1.9149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4096   -3.4546   -0.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3257   -2.4184   -1.6023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1730   -2.3423    0.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3091    1.1159    1.7728 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9028    0.5896    1.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3214   -0.3754    3.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7769    0.6826    3.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0296   -1.4974    5.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6067   -1.9737    4.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1623   -0.1799    4.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2772   -3.3292    3.5958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6211   -2.6720    3.6805 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4590   -2.9310    2.0590 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9945   -2.0076    2.3331 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5846   -0.2483    1.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6712   -1.5793    1.2344 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  2  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  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 30 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 36 38  1  0
 36 39  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  2 43  1  0
  2 44  1  0
  3 45  1  0
  3 46  1  0
  4 47  1  0
  4 48  1  0
  5 49  1  0
  5 50  1  0
  6 51  1  0
  6 52  1  0
  7 53  1  0
  7 54  1  0
  8 55  1  0
  8 56  1  0
  9 57  1  0
 10 58  1  0
 11 59  1  0
 11 60  1  0
 12 61  1  0
 12 62  1  0
 13 63  1  0
 13 64  1  0
 14 65  1  0
 14 66  1  0
 15 67  1  0
 15 68  1  0
 16 69  1  0
 16 70  1  0
 17 71  1  0
 17 72  1  0
 18 73  1  0
 18 74  1  0
 19 75  1  0
 19 76  1  0
 20 77  1  0
 20 78  1  0
 21 79  1  0
 21 80  1  0
 25 81  1  0
 25 82  1  0
 26 83  1  6
 27 84  1  0
 28 85  1  0
 28 86  1  0
 34 87  1  0
 34 88  1  0
 35 89  1  0
 35 90  1  0
 37 91  1  0
 37 92  1  0
 37 93  1  0
 38 94  1  0
 38 95  1  0
 38 96  1  0
 39 97  1  0
 39 98  1  0
 39 99  1  0
M  CHG  2  32  -1  36   1
M  END


  Mrv1652304202020522D          

 40 39  0  0  1  0            999 V2000
   22.6529   -2.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9477   -3.3880    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   21.2425   -2.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3581   -3.3880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5373   -3.3880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0632   -2.9809    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   24.4704   -3.6860    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   23.6561   -2.2757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7684   -2.5737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4736   -2.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1788   -2.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8840   -2.9809    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   26.4768   -3.6860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5366   -2.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5891   -3.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8188   -2.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5333   -3.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2478   -2.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9623   -3.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6768   -2.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3913   -3.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1057   -2.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8202   -3.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5347   -2.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2491   -2.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9637   -3.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6781   -2.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3926   -3.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1071   -2.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8215   -3.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5360   -2.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2505   -3.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9649   -2.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6795   -3.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3939   -2.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1084   -3.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8229   -2.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8229   -2.1505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8350   -3.9090    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.3029   -4.0170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  1  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  6  9  1  0  0  0  0
  9 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
 12 14  1  0  0  0  0
 12 15  1  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  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 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
 29 30  1  0  0  0  0
 30 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
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37  5  1  0  0  0  0
 37 38  2  0  0  0  0
  2 39  1  1  0  0  0
  2 40  1  6  0  0  0
M  CHG  2   7  -1  12   1
M  END
> <DATABASE_ID>
HMDB0010399

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@](O)(COC(=O)CCCCCCCCCCC\C=C/CCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H60NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-30(33)36-27-29(32)28-38-39(34,35)37-26-25-31(2,3)4/h12-13,29,32H,5-11,14-28H2,1-4H3/b13-12-/t29-/m1/s1

> <INCHI_KEY>
PAFOXYLFALKPOE-BKAVPCLVSA-N

> <FORMULA>
C30H60NO7P

> <MOLECULAR_WEIGHT>
577.7737

> <EXACT_MASS>
577.410739791

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
99

> <JCHEM_AVERAGE_POLARIZABILITY>
69.20157559564234

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{[(2R)-3-[(13Z)-docos-13-enoyloxy]-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium

> <ALOGPS_LOGP>
3.56

> <JCHEM_LOGP>
3.498232810194925

> <ALOGPS_LOGS>
-6.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.655609236411614

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8553406136270887

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4040033707844772

> <JCHEM_POLAR_SURFACE_AREA>
105.11999999999999

> <JCHEM_REFRACTIVITY>
170.99630000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
29

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.37e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-{[(2R)-3-[(13Z)-docos-13-enoyloxy]-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0010399
     RDKit          3D
LysoPC(22:1(13Z)/0:0)
 99 98  0  0  0  0  0  0  0  0999 V2000
    9.3675   -3.7794    1.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2199   -3.3856    2.3048 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6014   -2.1485    3.1234 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8862   -1.0455    2.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2685    0.1590    2.8117 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6891    1.4087    2.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9567    2.2617    1.3007 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6216    1.9782   -0.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8262    0.8788   -0.5411 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6517    1.0054   -1.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0468    2.3266   -1.4013 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8654    2.5271   -2.8951 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9753    1.5126   -3.5394 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5573    1.5051   -3.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8908    2.8239   -3.2364 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4882    2.9233   -2.7534 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6175    1.9140   -3.4195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8095    2.0056   -2.9822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0188    1.8148   -1.5237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5744    0.5174   -0.9539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2220   -0.6997   -1.5213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6819   -0.6161   -1.3053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3816   -0.0488   -2.1749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2331   -1.1554   -0.1717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6180   -1.1339    0.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3679   -1.9033   -0.9176 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9405   -3.2466   -0.9348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8569   -1.8654   -0.7589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3230   -0.5561   -0.7396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9917   -0.4819   -0.5627 P   0  0  0  0  0  5  0  0  0  0  0  0
   -9.3901    0.9691   -0.8437 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7889   -1.5601   -1.5870 O   0  0  0  0  0  1  0  0  0  0  0  0
   -9.3956   -0.8296    1.0218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9667    0.2236    1.6926 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2846   -0.2017    3.1006 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1907   -1.2991    3.2101 N   0  0  0  0  0  4  0  0  0  0  0  0
  -11.8118   -1.2090    4.5403 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5684   -2.6030    3.1339 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1947   -1.2536    2.1743 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3084   -3.1808    0.4477 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3421   -3.6157    1.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2353   -4.8338    1.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3470   -3.1608    1.6501 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9826   -4.2418    2.9480 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5314   -2.3345    3.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7952   -1.8300    3.7836 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6547   -1.4142    1.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8639   -0.9379    1.6062 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1253   -0.1801    3.5238 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4386    0.3332    3.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7335    1.1827    1.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0856    2.0537    3.1155 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5755    3.2569    1.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0204    2.7089    1.8404 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6782    1.8207   -0.6107 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3156    2.9071   -0.6578 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2070   -0.1734   -0.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1392    0.0742   -1.4484 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9737    2.2484   -1.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4663    3.1704   -0.8796 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8691    2.4153   -3.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5489    3.5578   -3.0590 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0079    1.6632   -4.6391 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4364    0.4959   -3.3640 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0406    0.6825   -3.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5640    1.2227   -1.9568 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8871    3.0430   -4.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4861    3.5881   -2.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4260    2.9180   -1.6447 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1076    3.9402   -3.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6477    2.1389   -4.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0150    0.8689   -3.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4757    1.3789   -3.6161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1308    3.0678   -3.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0886    2.0390   -1.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4607    2.6240   -0.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5319    0.4598   -1.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8062    0.5398    0.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0549   -0.8337   -2.6065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7996   -1.6254   -1.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9893   -0.0906    0.1426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7436   -1.5479    1.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1331   -1.5113   -1.9149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4096   -3.4546   -0.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3257   -2.4184   -1.6023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1730   -2.3423    0.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3091    1.1159    1.7728 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9028    0.5896    1.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3214   -0.3754    3.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7769    0.6826    3.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0296   -1.4974    5.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6067   -1.9737    4.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1623   -0.1799    4.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2772   -3.3292    3.5958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6211   -2.6720    3.6805 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4590   -2.9310    2.0590 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9945   -2.0076    2.3331 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5846   -0.2483    1.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6712   -1.5793    1.2344 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  2  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  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 30 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 36 38  1  0
 36 39  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  2 43  1  0
  2 44  1  0
  3 45  1  0
  3 46  1  0
  4 47  1  0
  4 48  1  0
  5 49  1  0
  5 50  1  0
  6 51  1  0
  6 52  1  0
  7 53  1  0
  7 54  1  0
  8 55  1  0
  8 56  1  0
  9 57  1  0
 10 58  1  0
 11 59  1  0
 11 60  1  0
 12 61  1  0
 12 62  1  0
 13 63  1  0
 13 64  1  0
 14 65  1  0
 14 66  1  0
 15 67  1  0
 15 68  1  0
 16 69  1  0
 16 70  1  0
 17 71  1  0
 17 72  1  0
 18 73  1  0
 18 74  1  0
 19 75  1  0
 19 76  1  0
 20 77  1  0
 20 78  1  0
 21 79  1  0
 21 80  1  0
 25 81  1  0
 25 82  1  0
 26 83  1  6
 27 84  1  0
 28 85  1  0
 28 86  1  0
 34 87  1  0
 34 88  1  0
 35 89  1  0
 35 90  1  0
 37 91  1  0
 37 92  1  0
 37 93  1  0
 38 94  1  0
 38 95  1  0
 38 96  1  0
 39 97  1  0
 39 98  1  0
 39 99  1  0
M  CHG  2  32  -1  36   1
M  END

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  C   UNK     0      42.285  -5.564   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      40.969  -6.324   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      39.653  -5.564   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      43.602  -6.324   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      38.336  -6.324   0.000  0.00  0.00           O+0
HETATM    6  P   UNK     0      44.918  -5.564   0.000  0.00  0.00           P+0
HETATM    7  O   UNK     0      45.678  -6.881   0.000  0.00  0.00           O-1
HETATM    8  O   UNK     0      44.158  -4.248   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      46.234  -4.804   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      47.551  -5.564   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      48.867  -4.804   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      50.183  -5.564   0.000  0.00  0.00           N+1
HETATM   13  C   UNK     0      49.423  -6.881   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      51.402  -3.973   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      51.500  -6.324   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.995  -5.554   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.329  -6.324   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.663  -5.554   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.996  -6.324   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.330  -5.554   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.664  -6.324   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.997  -5.554   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.331  -6.324   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      19.665  -5.554   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      20.998  -5.554   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      22.332  -6.324   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      23.666  -5.554   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      25.000  -6.324   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      26.333  -5.554   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      27.667  -6.324   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      29.001  -5.554   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      30.334  -6.324   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      31.668  -5.554   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      33.002  -6.324   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      34.335  -5.554   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      35.669  -6.324   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      37.003  -5.554   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      37.003  -4.014   0.000  0.00  0.00           O+0
HETATM   39  H   UNK     0      42.625  -7.297   0.000  0.00  0.00           H+0
HETATM   40  O   UNK     0      39.765  -7.498   0.000  0.00  0.00           O+0
CONECT    1    2    4                                                       
CONECT    2    1    3   39   40                                             
CONECT    3    2    5                                                       
CONECT    4    1    6                                                       
CONECT    5    3   37                                                       
CONECT    6    4    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12                                                            
CONECT   16   17                                                            
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36    5   38                                                  
CONECT   38   37                                                            
CONECT   39    2                                                            
CONECT   40    2                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   78    0
END

COMPND    HMDB0010399
HETATM    1  C1  UNL     1       9.367  -3.779   1.394  1.00  0.00           C  
HETATM    2  C2  UNL     1       8.220  -3.386   2.305  1.00  0.00           C  
HETATM    3  C3  UNL     1       8.601  -2.149   3.123  1.00  0.00           C  
HETATM    4  C4  UNL     1       8.886  -1.046   2.067  1.00  0.00           C  
HETATM    5  C5  UNL     1       9.269   0.159   2.812  1.00  0.00           C  
HETATM    6  C6  UNL     1       9.689   1.409   2.213  1.00  0.00           C  
HETATM    7  C7  UNL     1       8.957   2.262   1.301  1.00  0.00           C  
HETATM    8  C8  UNL     1       8.622   1.978  -0.084  1.00  0.00           C  
HETATM    9  C9  UNL     1       7.826   0.879  -0.541  1.00  0.00           C  
HETATM   10  C10 UNL     1       6.652   1.005  -1.144  1.00  0.00           C  
HETATM   11  C11 UNL     1       6.047   2.327  -1.401  1.00  0.00           C  
HETATM   12  C12 UNL     1       5.865   2.527  -2.895  1.00  0.00           C  
HETATM   13  C13 UNL     1       4.975   1.513  -3.539  1.00  0.00           C  
HETATM   14  C14 UNL     1       3.557   1.505  -3.020  1.00  0.00           C  
HETATM   15  C15 UNL     1       2.891   2.824  -3.236  1.00  0.00           C  
HETATM   16  C16 UNL     1       1.488   2.923  -2.753  1.00  0.00           C  
HETATM   17  C17 UNL     1       0.617   1.914  -3.420  1.00  0.00           C  
HETATM   18  C18 UNL     1      -0.809   2.006  -2.982  1.00  0.00           C  
HETATM   19  C19 UNL     1      -1.019   1.815  -1.524  1.00  0.00           C  
HETATM   20  C20 UNL     1      -0.574   0.517  -0.954  1.00  0.00           C  
HETATM   21  C21 UNL     1      -1.222  -0.700  -1.521  1.00  0.00           C  
HETATM   22  C22 UNL     1      -2.682  -0.616  -1.305  1.00  0.00           C  
HETATM   23  O1  UNL     1      -3.382  -0.049  -2.175  1.00  0.00           O  
HETATM   24  O2  UNL     1      -3.233  -1.155  -0.172  1.00  0.00           O  
HETATM   25  C23 UNL     1      -4.618  -1.134   0.119  1.00  0.00           C  
HETATM   26  C24 UNL     1      -5.368  -1.903  -0.918  1.00  0.00           C  
HETATM   27  O3  UNL     1      -4.941  -3.247  -0.935  1.00  0.00           O  
HETATM   28  C25 UNL     1      -6.857  -1.865  -0.759  1.00  0.00           C  
HETATM   29  O4  UNL     1      -7.323  -0.556  -0.740  1.00  0.00           O  
HETATM   30  P1  UNL     1      -8.992  -0.482  -0.563  1.00  0.00           P  
HETATM   31  O5  UNL     1      -9.390   0.969  -0.844  1.00  0.00           O  
HETATM   32  O6  UNL     1      -9.789  -1.560  -1.587  1.00  0.00           O1-
HETATM   33  O7  UNL     1      -9.396  -0.830   1.022  1.00  0.00           O  
HETATM   34  C26 UNL     1      -9.967   0.224   1.693  1.00  0.00           C  
HETATM   35  C27 UNL     1     -10.285  -0.202   3.101  1.00  0.00           C  
HETATM   36  N1  UNL     1     -11.191  -1.299   3.210  1.00  0.00           N1+
HETATM   37  C28 UNL     1     -11.812  -1.209   4.540  1.00  0.00           C  
HETATM   38  C29 UNL     1     -10.568  -2.603   3.134  1.00  0.00           C  
HETATM   39  C30 UNL     1     -12.195  -1.254   2.174  1.00  0.00           C  
HETATM   40  H1  UNL     1       9.308  -3.181   0.448  1.00  0.00           H  
HETATM   41  H2  UNL     1      10.342  -3.616   1.921  1.00  0.00           H  
HETATM   42  H3  UNL     1       9.235  -4.834   1.121  1.00  0.00           H  
HETATM   43  H4  UNL     1       7.347  -3.161   1.650  1.00  0.00           H  
HETATM   44  H5  UNL     1       7.983  -4.242   2.948  1.00  0.00           H  
HETATM   45  H6  UNL     1       9.531  -2.334   3.657  1.00  0.00           H  
HETATM   46  H7  UNL     1       7.795  -1.830   3.784  1.00  0.00           H  
HETATM   47  H8  UNL     1       9.655  -1.414   1.394  1.00  0.00           H  
HETATM   48  H9  UNL     1       7.864  -0.938   1.606  1.00  0.00           H  
HETATM   49  H10 UNL     1      10.125  -0.180   3.524  1.00  0.00           H  
HETATM   50  H11 UNL     1       8.439   0.333   3.604  1.00  0.00           H  
HETATM   51  H12 UNL     1      10.734   1.183   1.726  1.00  0.00           H  
HETATM   52  H13 UNL     1      10.086   2.054   3.116  1.00  0.00           H  
HETATM   53  H14 UNL     1       9.575   3.257   1.260  1.00  0.00           H  
HETATM   54  H15 UNL     1       8.020   2.709   1.840  1.00  0.00           H  
HETATM   55  H16 UNL     1       9.678   1.821  -0.611  1.00  0.00           H  
HETATM   56  H17 UNL     1       8.316   2.907  -0.658  1.00  0.00           H  
HETATM   57  H18 UNL     1       8.207  -0.173  -0.456  1.00  0.00           H  
HETATM   58  H19 UNL     1       6.139   0.074  -1.448  1.00  0.00           H  
HETATM   59  H20 UNL     1       4.974   2.248  -1.009  1.00  0.00           H  
HETATM   60  H21 UNL     1       6.466   3.170  -0.880  1.00  0.00           H  
HETATM   61  H22 UNL     1       6.869   2.415  -3.370  1.00  0.00           H  
HETATM   62  H23 UNL     1       5.549   3.558  -3.059  1.00  0.00           H  
HETATM   63  H24 UNL     1       5.008   1.663  -4.639  1.00  0.00           H  
HETATM   64  H25 UNL     1       5.436   0.496  -3.364  1.00  0.00           H  
HETATM   65  H26 UNL     1       3.041   0.682  -3.606  1.00  0.00           H  
HETATM   66  H27 UNL     1       3.564   1.223  -1.957  1.00  0.00           H  
HETATM   67  H28 UNL     1       2.887   3.043  -4.344  1.00  0.00           H  
HETATM   68  H29 UNL     1       3.486   3.588  -2.690  1.00  0.00           H  
HETATM   69  H30 UNL     1       1.426   2.918  -1.645  1.00  0.00           H  
HETATM   70  H31 UNL     1       1.108   3.940  -3.062  1.00  0.00           H  
HETATM   71  H32 UNL     1       0.648   2.139  -4.522  1.00  0.00           H  
HETATM   72  H33 UNL     1       1.015   0.869  -3.349  1.00  0.00           H  
HETATM   73  H34 UNL     1      -1.476   1.379  -3.616  1.00  0.00           H  
HETATM   74  H35 UNL     1      -1.131   3.068  -3.210  1.00  0.00           H  
HETATM   75  H36 UNL     1      -2.089   2.039  -1.313  1.00  0.00           H  
HETATM   76  H37 UNL     1      -0.461   2.624  -0.981  1.00  0.00           H  
HETATM   77  H38 UNL     1       0.532   0.460  -1.029  1.00  0.00           H  
HETATM   78  H39 UNL     1      -0.806   0.540   0.137  1.00  0.00           H  
HETATM   79  H40 UNL     1      -1.055  -0.834  -2.606  1.00  0.00           H  
HETATM   80  H41 UNL     1      -0.800  -1.625  -1.047  1.00  0.00           H  
HETATM   81  H42 UNL     1      -4.989  -0.091   0.143  1.00  0.00           H  
HETATM   82  H43 UNL     1      -4.744  -1.548   1.133  1.00  0.00           H  
HETATM   83  H44 UNL     1      -5.133  -1.511  -1.915  1.00  0.00           H  
HETATM   84  H45 UNL     1      -4.410  -3.455  -0.124  1.00  0.00           H  
HETATM   85  H46 UNL     1      -7.326  -2.418  -1.602  1.00  0.00           H  
HETATM   86  H47 UNL     1      -7.173  -2.342   0.188  1.00  0.00           H  
HETATM   87  H48 UNL     1      -9.309   1.116   1.773  1.00  0.00           H  
HETATM   88  H49 UNL     1     -10.903   0.590   1.215  1.00  0.00           H  
HETATM   89  H50 UNL     1      -9.321  -0.375   3.624  1.00  0.00           H  
HETATM   90  H51 UNL     1     -10.777   0.683   3.603  1.00  0.00           H  
HETATM   91  H52 UNL     1     -11.030  -1.497   5.283  1.00  0.00           H  
HETATM   92  H53 UNL     1     -12.607  -1.974   4.602  1.00  0.00           H  
HETATM   93  H54 UNL     1     -12.162  -0.180   4.758  1.00  0.00           H  
HETATM   94  H55 UNL     1     -11.277  -3.329   3.596  1.00  0.00           H  
HETATM   95  H56 UNL     1      -9.621  -2.672   3.681  1.00  0.00           H  
HETATM   96  H57 UNL     1     -10.459  -2.931   2.059  1.00  0.00           H  
HETATM   97  H58 UNL     1     -12.994  -2.008   2.333  1.00  0.00           H  
HETATM   98  H59 UNL     1     -12.585  -0.248   1.993  1.00  0.00           H  
HETATM   99  H60 UNL     1     -11.671  -1.579   1.234  1.00  0.00           H  
CONECT    1    2   40   41   42
CONECT    2    3   43   44
CONECT    3    4   45   46
CONECT    4    5   47   48
CONECT    5    6   49   50
CONECT    6    7   51   52
CONECT    7    8   53   54
CONECT    8    9   55   56
CONECT    9   10   10   57
CONECT   10   11   58
CONECT   11   12   59   60
CONECT   12   13   61   62
CONECT   13   14   63   64
CONECT   14   15   65   66
CONECT   15   16   67   68
CONECT   16   17   69   70
CONECT   17   18   71   72
CONECT   18   19   73   74
CONECT   19   20   75   76
CONECT   20   21   77   78
CONECT   21   22   79   80
CONECT   22   23   23   24
CONECT   24   25
CONECT   25   26   81   82
CONECT   26   27   28   83
CONECT   27   84
CONECT   28   29   85   86
CONECT   29   30
CONECT   30   31   31   32   33
CONECT   33   34
CONECT   34   35   87   88
CONECT   35   36   89   90
CONECT   36   37   38   39
CONECT   37   91   92   93
CONECT   38   94   95   96
CONECT   39   97   98   99
END

HMDB0010399
     RDKit          3D
LysoPC(22:1(13Z)/0:0)
 99 98  0  0  0  0  0  0  0  0999 V2000
    9.3675   -3.7794    1.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2199   -3.3856    2.3048 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6014   -2.1485    3.1234 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8862   -1.0455    2.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2685    0.1590    2.8117 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6891    1.4087    2.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9567    2.2617    1.3007 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6216    1.9782   -0.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8262    0.8788   -0.5411 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6517    1.0054   -1.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0468    2.3266   -1.4013 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8654    2.5271   -2.8951 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9753    1.5126   -3.5394 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5573    1.5051   -3.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8908    2.8239   -3.2364 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4882    2.9233   -2.7534 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6175    1.9140   -3.4195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8095    2.0056   -2.9822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0188    1.8148   -1.5237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5744    0.5174   -0.9539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2220   -0.6997   -1.5213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6819   -0.6161   -1.3053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3816   -0.0488   -2.1749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2331   -1.1554   -0.1717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6180   -1.1339    0.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3679   -1.9033   -0.9176 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9405   -3.2466   -0.9348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8569   -1.8654   -0.7589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3230   -0.5561   -0.7396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9917   -0.4819   -0.5627 P   0  0  0  0  0  5  0  0  0  0  0  0
   -9.3901    0.9691   -0.8437 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7889   -1.5601   -1.5870 O   0  0  0  0  0  1  0  0  0  0  0  0
   -9.3956   -0.8296    1.0218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9667    0.2236    1.6926 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2846   -0.2017    3.1006 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1907   -1.2991    3.2101 N   0  0  0  0  0  4  0  0  0  0  0  0
  -11.8118   -1.2090    4.5403 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5684   -2.6030    3.1339 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1947   -1.2536    2.1743 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3084   -3.1808    0.4477 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3421   -3.6157    1.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2353   -4.8338    1.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3470   -3.1608    1.6501 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9826   -4.2418    2.9480 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5314   -2.3345    3.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7952   -1.8300    3.7836 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6547   -1.4142    1.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8639   -0.9379    1.6062 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1253   -0.1801    3.5238 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4386    0.3332    3.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7335    1.1827    1.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0856    2.0537    3.1155 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5755    3.2569    1.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0204    2.7089    1.8404 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6782    1.8207   -0.6107 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3156    2.9071   -0.6578 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2070   -0.1734   -0.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1392    0.0742   -1.4484 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9737    2.2484   -1.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4663    3.1704   -0.8796 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8691    2.4153   -3.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5489    3.5578   -3.0590 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0079    1.6632   -4.6391 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4364    0.4959   -3.3640 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0406    0.6825   -3.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5640    1.2227   -1.9568 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8871    3.0430   -4.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4861    3.5881   -2.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4260    2.9180   -1.6447 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1076    3.9402   -3.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6477    2.1389   -4.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0150    0.8689   -3.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4757    1.3789   -3.6161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1308    3.0678   -3.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0886    2.0390   -1.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4607    2.6240   -0.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5319    0.4598   -1.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8062    0.5398    0.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0549   -0.8337   -2.6065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7996   -1.6254   -1.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9893   -0.0906    0.1426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7436   -1.5479    1.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1331   -1.5113   -1.9149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4096   -3.4546   -0.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3257   -2.4184   -1.6023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1730   -2.3423    0.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3091    1.1159    1.7728 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9028    0.5896    1.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3214   -0.3754    3.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7769    0.6826    3.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0296   -1.4974    5.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6067   -1.9737    4.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1623   -0.1799    4.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2772   -3.3292    3.5958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6211   -2.6720    3.6805 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4590   -2.9310    2.0590 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9945   -2.0076    2.3331 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5846   -0.2483    1.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6712   -1.5793    1.2344 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  2  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  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 30 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 36 38  1  0
 36 39  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  2 43  1  0
  2 44  1  0
  3 45  1  0
  3 46  1  0
  4 47  1  0
  4 48  1  0
  5 49  1  0
  5 50  1  0
  6 51  1  0
  6 52  1  0
  7 53  1  0
  7 54  1  0
  8 55  1  0
  8 56  1  0
  9 57  1  0
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 34 87  1  0
 34 88  1  0
 35 89  1  0
 35 90  1  0
 37 91  1  0
 37 92  1  0
 37 93  1  0
 38 94  1  0
 38 95  1  0
 38 96  1  0
 39 97  1  0
 39 98  1  0
 39 99  1  0
M  CHG  2  32  -1  36   1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Erucoyl-glycero-3-phosphocholine	HMDB
LPC(22:1)	HMDB
LPC(22:1/0:0)	HMDB
LPC(22:1n9/0:0)	HMDB
LPC(22:1W9/0:0)	HMDB
LyPC(22:1)	HMDB
LyPC(22:1/0:0)	HMDB
LyPC(22:1n9/0:0)	HMDB
LyPC(22:1W9/0:0)	HMDB
LysoPC(22:1)	HMDB
LysoPC(22:1/0:0)	HMDB
LysoPC(22:1n9/0:0)	HMDB
LysoPC(22:1W9/0:0)	HMDB
Lysophosphatidylcholine(22:1)	HMDB
Lysophosphatidylcholine(22:1/0:0)	HMDB
Lysophosphatidylcholine(22:1n9/0:0)	HMDB
Lysophosphatidylcholine(22:1W9/0:0)	HMDB
LysoPC(22:1(13Z))	HMDB
1-(13Z-Docosenoyl)-glycero-3-phosphocholine	HMDB
1-Erucoylglycerophosphocholine	HMDB

Chemical Formula

C₃₀H₆₀NO₇P

Average Molecular Weight

577.7737

Monoisotopic Molecular Weight

577.410739791

IUPAC Name

(2-{[(2R)-3-[(13Z)-docos-13-enoyloxy]-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-3-[(13Z)-docos-13-enoyloxy]-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C30H60NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-30(33)36-27-29(32)28-38-39(34,35)37-26-25-31(2,3)4/h12-13,29,32H,5-11,14-28H2,1-4H3/b13-12-/t29-/m1/s1

InChI Key

PAFOXYLFALKPOE-BKAVPCLVSA-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

Ontology

Not Available

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

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	8.4e-05 g/L	ALOGPS
logP	3.56	ALOGPS
logP	3.5	ChemAxon
logS	-6.9	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	29	ChemAxon
Refractivity	171 m³·mol⁻¹	ChemAxon
Polarizability	69.2 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]+	234.046	30932474
DeepCCS	[M-H]-	230.749	30932474
DeepCCS	[M-2H]-	264.999	30932474
DeepCCS	[M+Na]+	241.353	30932474
AllCCS	[M+H]+	250.7	32859911
AllCCS	[M+H-H2O]+	249.7	32859911
AllCCS	[M+NH4]+	251.6	32859911
AllCCS	[M+Na]+	251.8	32859911
AllCCS	[M-H]-	246.5	32859911
AllCCS	[M+Na-2H]-	250.1	32859911
AllCCS	[M+HCOO]-	254.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
LysoPC(22:1(13Z)/0:0)	CCCCCCCC\C=C/CCCCCCCCCCCC(=O)OC[C@@]([H])(O)COP([O-])(=O)OCC[N+](C)(C)C	3886.0	Standard polar	33892256
LysoPC(22:1(13Z)/0:0)	CCCCCCCC\C=C/CCCCCCCCCCCC(=O)OC[C@@]([H])(O)COP([O-])(=O)OCC[N+](C)(C)C	3457.5	Standard non polar	33892256
LysoPC(22:1(13Z)/0:0)	CCCCCCCC\C=C/CCCCCCCCCCCC(=O)OC[C@@]([H])(O)COP([O-])(=O)OCC[N+](C)(C)C	3907.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
LysoPC(22:1(13Z)/0:0),1TMS,isomer #1	CCCCCCCC/C=C\CCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O[Si](C)(C)C	3889.5	Semi standard non polar	33892256
LysoPC(22:1(13Z)/0:0),1TBDMS,isomer #1	CCCCCCCC/C=C\CCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C	4128.8	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(22:1(13Z)/0:0) GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ed-5941200000-ea619fcb42166e0fa399	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - LysoPC(22:1(13Z)/0:0) GC-MS (1 TMS) - 70eV, Positive	splash10-0233-9412001000-2227b2f287aa1e70b51c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - LysoPC(22:1(13Z)/0:0) GC-MS ("LysoPC(22:1(13Z)/0:0),1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - LysoPC(22:1(13Z)/0:0) GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-15	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(22:1(13Z)/0:0) 10V, Positive-QTOF	splash10-000i-9126030000-41dc72c796ec37851780	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(22:1(13Z)/0:0) 20V, Positive-QTOF	splash10-00du-9348010000-cf9a7745c2ae81ec6d9d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(22:1(13Z)/0:0) 40V, Positive-QTOF	splash10-05a9-9023000000-f6fcc434144367501ea6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(22:1(13Z)/0:0) 10V, Negative-QTOF	splash10-00n0-0009140000-c9000b41fb63caba7c01	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(22:1(13Z)/0:0) 20V, Negative-QTOF	splash10-00kr-0009100000-60ea12545ec113640b78	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(22:1(13Z)/0:0) 40V, Negative-QTOF	splash10-00n0-5119000000-2bbce4ac121a8cefb18a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(22:1(13Z)/0:0) 10V, Positive-QTOF	splash10-001i-0000090000-39eedd6e51bddec63dfa	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(22:1(13Z)/0:0) 20V, Positive-QTOF	splash10-0060-0001090000-0f06ab57848f4e9e59a5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(22:1(13Z)/0:0) 40V, Positive-QTOF	splash10-0ufs-1609770000-19f90f55cfc358341f17	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(22:1(13Z)/0:0) 10V, Negative-QTOF	splash10-03di-0000039000-285f86ddfb76289458e7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(22:1(13Z)/0:0) 20V, Negative-QTOF	splash10-01p9-0009016000-0bba2b894f93dc35cf89	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(22:1(13Z)/0:0) 40V, Negative-QTOF	splash10-000i-0039011000-31c0eee870a88e98003c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(22:1(13Z)/0:0) 10V, Negative-QTOF	splash10-004i-0003090000-c7d44a75da892d1b4fa1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(22:1(13Z)/0:0) 20V, Negative-QTOF	splash10-000i-1009010000-7e385a98f41f434c2c89	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(22:1(13Z)/0:0) 40V, Negative-QTOF	splash10-000i-0009000000-36b8b1e7caa291bed45a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(22:1(13Z)/0:0) 10V, Positive-QTOF	splash10-0udi-0000019000-cfa91d32327681c1b9bf	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(22:1(13Z)/0:0) 20V, Positive-QTOF	splash10-0f6x-0001096000-365b66832ac4c117c1dd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(22:1(13Z)/0:0) 40V, Positive-QTOF	splash10-0gbf-1701981000-f9bdd10f4c97717d33d7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(22:1(13Z)/0:0) 10V, Positive-QTOF	splash10-01t9-0000090000-a29d6a14d513c0d92105	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(22:1(13Z)/0:0) 20V, Positive-QTOF	splash10-003r-0900060000-48abe3418040067dbcc1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(22:1(13Z)/0:0) 40V, Positive-QTOF	splash10-0gx0-0910040000-18a0e9683d2b54e2ca58	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood

Tissue Locations

All Tissues

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.569 +/- 0.260 uM	Adult (>18 years old)	Both	Normal	18953024	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

FDB027550

KNApSAcK ID

Not Available

Chemspider ID

24766534

KEGG Compound ID

C04230

BioCyc ID

PHOSPHATIDYLCHOLINE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53480471

PDB ID

Not Available

ChEBI ID

88684

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

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 ]

Only showing the first 10 proteins. There are 29 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Acyl-protein thioesterase 1

General function:: Involved in hydrolase activity
Specific function:: Hydrolyzes fatty acids from S-acylated cysteine residues in proteins such as trimeric G alpha proteins or HRAS. Has depalmitoylating activity and also low lysophospholipase activity.
Gene Name:: LYPLA1
Uniprot ID:: O75608
Molecular weight:: 24669.355

Enzyme Details

2. Group XV phospholipase A2

General function:: Involved in phosphatidylcholine-sterol O-acyltransferase activity
Specific function:: Has transacylase and calcium-independent phospholipase A2 activity. Catalyzes the formation of 1-O-acyl-N-acetylsphingosine and the concomitant release of a lyso-phospholipid (By similarity). May have weak lysophospholipase activity.
Gene Name:: PLA2G15
Uniprot ID:: Q8NCC3
Molecular weight:: Not Available

Enzyme Details

3. Calcium-dependent phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. This isozyme hydrolyzes more efficiently L-alpha-1-palmitoyl-2-oleoyl phosphatidylcholine than L-alpha-1-palmitoyl-2-arachidonyl phosphatidylcholine, L-alpha-1-palmitoyl-2-arachidonyl phosphatidylethanolamine, or L-alpha-1-stearoyl-2-arachidonyl phosphatidylinositol. May be involved in the production of lung surfactant, the remodeling or regulation of cardiac muscle.
Gene Name:: PLA2G5
Uniprot ID:: P39877
Molecular weight:: 15674.065

Enzyme Details

4. Group IIF secretory phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Hydrolyzes phosphatidylglycerol versus phosphatidylcholine with a 15-fold preference.
Gene Name:: PLA2G2F
Uniprot ID:: Q9BZM2
Molecular weight:: 23256.29

Enzyme Details

5. 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

6. Phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides.
Gene Name:: PLA2G1B
Uniprot ID:: P04054
Molecular weight:: 16359.535

Enzyme Details

7. Group XIIB secretory phospholipase A2-like protein

General function:: Involved in phospholipase A2 activity
Specific function:: Not known; does not seem to have catalytic activity.
Gene Name:: PLA2G12B
Uniprot ID:: Q9BX93
Molecular weight:: Not Available

Enzyme Details

8. Group 10 secretory phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a powerful potency for releasing arachidonic acid from cell membrane phospholipids. Prefers phosphatidylethanolamine and phosphatidylcholine liposomes to those of phosphatidylserine.
Gene Name:: PLA2G10
Uniprot ID:: O15496
Molecular weight:: 18153.04

Enzyme Details

9. Group IIE secretory phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a preference for arachidonic-containing phospholipids.
Gene Name:: PLA2G2E
Uniprot ID:: Q9NZK7
Molecular weight:: 15988.525

Enzyme Details

10. Acyl-protein thioesterase 2

General function:: Involved in hydrolase activity
Specific function:: May hydrolyze fatty acids from S-acylated cysteine residues in proteins such as trimeric G alpha proteins or HRAS. Has lysophospholipase activity (By similarity). Deacylates GAP43.
Gene Name:: LYPLA2
Uniprot ID:: O95372
Molecular weight:: 24736.71

Only showing the first 10 proteins. There are 29 proteins in total.

Show all enzymes and transporters

Showing metabocard for LysoPC(22:1(13Z)/0:0) (HMDB0010399)

MOL for HMDB0010399 (LysoPC(22:1(13Z)/0:0))

3D MOL for HMDB0010399 (LysoPC(22:1(13Z)/0:0))

3D SDF for HMDB0010399 (LysoPC(22:1(13Z)/0:0))

3D-SDF for HMDB0010399 (LysoPC(22:1(13Z)/0:0))

PDB for HMDB0010399 (LysoPC(22:1(13Z)/0:0))

3D PDB for HMDB0010399 (LysoPC(22:1(13Z)/0:0))

SMILES for HMDB0010399 (LysoPC(22:1(13Z)/0:0))

INCHI for HMDB0010399 (LysoPC(22:1(13Z)/0:0))

Structure for HMDB0010399 (LysoPC(22:1(13Z)/0:0))

3D Structure for HMDB0010399 (LysoPC(22:1(13Z)/0:0))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes