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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2018-03-20 20:04:54 UTC

Update Date

2022-11-30 19:53:42 UTC

HMDB ID

HMDB0240262

Secondary Accession Numbers

HMDB0061702
HMDB61702

Metabolite Identification

Common Name

LysoPC(0:0/16:0)

Description

LysoPC(0:0/16:0) is a lysophosphatidylcholine, which is a lysophospholipid. The term 'lysophospholipid' (LPL) refers to any phospholipid that is missing one of its two O-acyl chains. Thus, LPLs have a free alcohol in either the sn-1 or sn-2 position. The prefix 'lyso-' comes from the fact that lysophospholipids were originally found to be hemolytic however it is now used to refer generally to phospholipids missing an acyl chain. LPLs are usually the result of phospholipase A-type enzymatic activity on regular phospholipids such as phosphatidylcholine or phosphatidic acid, although they can also be generated by the acylation of glycerophospholipids or the phosphorylation of monoacylglycerols. 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. There is also a phospholipase A1, which is able to cleave the sn-1 ester bond. Lysophosphatidylcholine has pro-inflammatory properties in vitro and it is known to be a pathological component of oxidized lipoproteins (LDL) in plasma and of atherosclerotic lesions. Recently, it has been found to have some functions in cell signalling, and specific receptors (coupled to G proteins) have been identified. It activates the specific phospholipase C that releases diacylglycerols and inositol triphosphate with resultant increases in intracellular Ca2+ and activation of protein kinase C. It also activates the mitogen-activated protein kinase in certain cell types. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) or C-2 (sn-2) position. LysoPC(0:0/16:0), in particular, consists of one chain of palmitic acid at the C-2 position. 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

LysoPC(0:0/16:0)
  Mrv1652311211900192D          

 33 32  0  0  0  0            999 V2000
   23.3644   -6.5407    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   23.3644   -7.3657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1894   -6.5407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9038   -6.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6183   -6.5407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3328   -6.1282    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   27.0473   -5.7157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7453   -6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9203   -5.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6620   -6.5288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3644   -5.7157    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   21.9475   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2330   -6.5288    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.5185   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8041   -6.5288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2330   -7.3538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5185   -7.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5185   -8.5377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8044   -7.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0903   -7.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3762   -7.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6621   -7.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9479   -7.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2338   -7.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5197   -7.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8056   -7.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0915   -7.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3773   -7.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6632   -7.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9491   -7.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2350   -7.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5209   -7.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8067   -7.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  1 10  1  0  0  0  0
  1 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 10 12  1  0  0  0  0
 13 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 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  1  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
M  CHG  2   6   1  11  -1
M  END

HMDB0240262
     RDKit          3D
LysoPC(0:0/16:0)
 83 82  0  0  0  0  0  0  0  0999 V2000
   10.3660    0.4572   -0.9607 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5500   -0.5166   -1.7354 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9763   -1.6608   -1.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9811   -1.5971    0.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0802   -0.9754    1.3236 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2774    0.4581    1.5393 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2236    1.3446    0.9012 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8344    1.0286    1.4449 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8810    1.9667    0.7400 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4456    1.7688    1.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9814    0.3551    0.8900 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0684    0.0600   -0.5910 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6138   -1.3296   -0.8873 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1821   -1.5794   -0.4755 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2184   -0.6611   -1.1820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1462   -0.9752   -0.7210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184   -1.8793    0.1230 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2095   -0.2699   -1.2258 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5537   -0.4953   -0.8480 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4106   -0.8503   -2.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3363    0.2296   -2.9231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0914    0.8097   -0.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4371    0.6543    0.0972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9491    2.1344    0.6827 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.0988    2.4663    1.8987 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7536    3.3703   -0.4615 O   0  0  0  0  0  1  0  0  0  0  0  0
   -7.5545    1.9968    1.1856 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1136    0.9030    0.5286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5494    0.7943    0.9897 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2448   -0.3162    0.3717 N   0  0  0  0  0  4  0  0  0  0  0  0
  -11.6663   -0.0420    0.4587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9607   -1.5707    1.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8991   -0.4438   -1.0220 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2925    0.7498   -1.5481 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7734    1.3703   -0.7333 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7390    0.0104   -0.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7722    0.1002   -2.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2191   -0.8547   -2.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5411   -2.3388   -1.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8358   -2.3370   -0.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7203   -2.7186    0.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9380   -1.3231   -0.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1316   -1.2581    1.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8846   -1.5063    1.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2463    0.9131    1.4965 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0179    0.6037    2.6817 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4539    2.3819    1.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2533    1.3355   -0.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8603    1.2925    2.5233 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6015   -0.0312    1.2862 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0052    1.9035   -0.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1659    3.0037    1.0671 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8322    2.4556    0.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3179    1.9852    2.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5927   -0.3599    1.4568 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9190    0.2935    1.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6011    0.8337   -1.2036 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1692    0.0958   -0.8398 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2417   -2.0315   -0.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7248   -1.6266   -1.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8593   -2.6145   -0.6921 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0179   -1.4350    0.6169 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2185   -0.8493   -2.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4872    0.4030   -1.0134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6911   -1.2849   -0.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1604   -1.8101   -2.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4635   -0.9090   -1.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4346    0.6511   -2.8885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1019    1.5919   -1.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4887    1.2164    0.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0316    0.9878   -0.5786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5103    0.0204    0.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5254    0.7090    2.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0562    1.7264    0.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8471    1.0605    0.4864 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2532   -0.5043   -0.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0199   -0.4207    1.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9897   -1.9913    0.7601 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1115   -1.4688    2.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7435   -2.2957    0.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8704    0.5778   -1.4845 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6474   -1.0788   -1.5473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8739   -0.8598   -1.1036 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  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 24 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 30 33  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  2 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  0
  4 42  1  0
  5 43  1  0
  5 44  1  0
  6 45  1  0
  6 46  1  0
  7 47  1  0
  7 48  1  0
  8 49  1  0
  8 50  1  0
  9 51  1  0
  9 52  1  0
 10 53  1  0
 10 54  1  0
 11 55  1  0
 11 56  1  0
 12 57  1  0
 12 58  1  0
 13 59  1  0
 13 60  1  0
 14 61  1  0
 14 62  1  0
 15 63  1  0
 15 64  1  0
 19 65  1  1
 20 66  1  0
 20 67  1  0
 21 68  1  0
 22 69  1  0
 22 70  1  0
 28 71  1  0
 28 72  1  0
 29 73  1  0
 29 74  1  0
 31 75  1  0
 31 76  1  0
 31 77  1  0
 32 78  1  0
 32 79  1  0
 32 80  1  0
 33 81  1  0
 33 82  1  0
 33 83  1  0
M  CHG  2  26  -1  30   1
M  END

LysoPC(0:0/16:0)
  Mrv1652311211900192D          

 33 32  0  0  0  0            999 V2000
   23.3644   -6.5407    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   23.3644   -7.3657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1894   -6.5407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9038   -6.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6183   -6.5407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3328   -6.1282    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   27.0473   -5.7157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7453   -6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9203   -5.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6620   -6.5288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3644   -5.7157    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   21.9475   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2330   -6.5288    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.5185   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8041   -6.5288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2330   -7.3538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5185   -7.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5185   -8.5377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8044   -7.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0903   -7.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3762   -7.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6621   -7.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9479   -7.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2338   -7.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5197   -7.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8056   -7.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0915   -7.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3773   -7.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6632   -7.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9491   -7.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2350   -7.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5209   -7.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8067   -7.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  1 10  1  0  0  0  0
  1 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 10 12  1  0  0  0  0
 13 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 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  1  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
M  CHG  2   6   1  11  -1
M  END
> <DATABASE_ID>
HMDB0240262

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C24H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-24(27)32-23(21-26)22-31-33(28,29)30-20-19-25(2,3)4/h23,26H,5-22H2,1-4H3/t23-/m1/s1

> <INCHI_KEY>
NEGQHKSYEYVFTD-HSZRJFAPSA-N

> <FORMULA>
C24H50NO7P

> <MOLECULAR_WEIGHT>
495.638

> <EXACT_MASS>
495.332489952

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
57.50951901531522

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{[(2R)-2-(hexadecanoyloxy)-3-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium

> <ALOGPS_LOGP>
1.82

> <JCHEM_LOGP>
1.1927424768615884

> <ALOGPS_LOGS>
-6.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.579258211672176

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8550617598182955

> <JCHEM_PKA_STRONGEST_BASIC>
-2.983758125699806

> <JCHEM_POLAR_SURFACE_AREA>
105.12

> <JCHEM_REFRACTIVITY>
142.27370000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
24

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.77e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-{[(2R)-2-(hexadecanoyloxy)-3-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0240262
     RDKit          3D
LysoPC(0:0/16:0)
 83 82  0  0  0  0  0  0  0  0999 V2000
   10.3660    0.4572   -0.9607 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5500   -0.5166   -1.7354 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9763   -1.6608   -1.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9811   -1.5971    0.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0802   -0.9754    1.3236 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2774    0.4581    1.5393 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2236    1.3446    0.9012 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8344    1.0286    1.4449 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8810    1.9667    0.7400 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4456    1.7688    1.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9814    0.3551    0.8900 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0684    0.0600   -0.5910 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6138   -1.3296   -0.8873 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1821   -1.5794   -0.4755 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2184   -0.6611   -1.1820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1462   -0.9752   -0.7210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184   -1.8793    0.1230 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2095   -0.2699   -1.2258 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5537   -0.4953   -0.8480 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4106   -0.8503   -2.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3363    0.2296   -2.9231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0914    0.8097   -0.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4371    0.6543    0.0972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9491    2.1344    0.6827 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.0988    2.4663    1.8987 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7536    3.3703   -0.4615 O   0  0  0  0  0  1  0  0  0  0  0  0
   -7.5545    1.9968    1.1856 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1136    0.9030    0.5286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5494    0.7943    0.9897 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2448   -0.3162    0.3717 N   0  0  0  0  0  4  0  0  0  0  0  0
  -11.6663   -0.0420    0.4587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9607   -1.5707    1.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8991   -0.4438   -1.0220 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2925    0.7498   -1.5481 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7734    1.3703   -0.7333 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7390    0.0104   -0.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7722    0.1002   -2.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2191   -0.8547   -2.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5411   -2.3388   -1.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8358   -2.3370   -0.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7203   -2.7186    0.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9380   -1.3231   -0.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1316   -1.2581    1.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8846   -1.5063    1.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2463    0.9131    1.4965 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0179    0.6037    2.6817 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4539    2.3819    1.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2533    1.3355   -0.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8603    1.2925    2.5233 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6015   -0.0312    1.2862 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0052    1.9035   -0.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1659    3.0037    1.0671 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8322    2.4556    0.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3179    1.9852    2.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5927   -0.3599    1.4568 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9190    0.2935    1.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6011    0.8337   -1.2036 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1692    0.0958   -0.8398 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2417   -2.0315   -0.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7248   -1.6266   -1.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8593   -2.6145   -0.6921 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0179   -1.4350    0.6169 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2185   -0.8493   -2.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4872    0.4030   -1.0134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6911   -1.2849   -0.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1604   -1.8101   -2.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4635   -0.9090   -1.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4346    0.6511   -2.8885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1019    1.5919   -1.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4887    1.2164    0.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0316    0.9878   -0.5786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5103    0.0204    0.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5254    0.7090    2.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0562    1.7264    0.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8471    1.0605    0.4864 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2532   -0.5043   -0.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0199   -0.4207    1.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9897   -1.9913    0.7601 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1115   -1.4688    2.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7435   -2.2957    0.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8704    0.5778   -1.4845 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6474   -1.0788   -1.5473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8739   -0.8598   -1.1036 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  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 24 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 30 33  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  2 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  0
  4 42  1  0
  5 43  1  0
  5 44  1  0
  6 45  1  0
  6 46  1  0
  7 47  1  0
  7 48  1  0
  8 49  1  0
  8 50  1  0
  9 51  1  0
  9 52  1  0
 10 53  1  0
 10 54  1  0
 11 55  1  0
 11 56  1  0
 12 57  1  0
 12 58  1  0
 13 59  1  0
 13 60  1  0
 14 61  1  0
 14 62  1  0
 15 63  1  0
 15 64  1  0
 19 65  1  1
 20 66  1  0
 20 67  1  0
 21 68  1  0
 22 69  1  0
 22 70  1  0
 28 71  1  0
 28 72  1  0
 29 73  1  0
 29 74  1  0
 31 75  1  0
 31 76  1  0
 31 77  1  0
 32 78  1  0
 32 79  1  0
 32 80  1  0
 33 81  1  0
 33 82  1  0
 33 83  1  0
M  CHG  2  26  -1  30   1
M  END

HEADER    PROTEIN                                 21-NOV-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: LysoPC(0:0/16:0)                                  
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-NOV-19         0                                  
HETATM    1  P   UNK     0      43.614 -12.209   0.000  0.00  0.00           P+0
HETATM    2  O   UNK     0      43.614 -13.749   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      45.154 -12.209   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      46.487 -11.439   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      47.821 -12.209   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      49.155 -11.439   0.000  0.00  0.00           N+1
HETATM    7  C   UNK     0      50.488 -10.669   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      49.925 -12.773   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      48.385 -10.106   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      42.302 -12.187   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      43.614 -10.669   0.000  0.00  0.00           O-1
HETATM   12  C   UNK     0      40.969 -11.417   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      39.635 -12.187   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      38.301 -11.417   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      36.968 -12.187   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      39.635 -13.727   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      38.301 -14.497   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      38.301 -15.937   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      36.968 -13.726   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      35.635 -14.497   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      34.302 -13.726   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      32.969 -14.497   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      31.636 -13.726   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      30.303 -14.497   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      28.970 -13.726   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      27.637 -14.497   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      26.304 -13.726   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      24.971 -14.497   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      23.638 -13.726   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      22.305 -14.497   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      20.972 -13.726   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      19.639 -14.497   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      18.306 -13.726   0.000  0.00  0.00           C+0
CONECT    1    2    3   10   11                                             
CONECT    2    1                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6                                                            
CONECT   10    1   12                                                       
CONECT   11    1                                                            
CONECT   12   13   10                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   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                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   64    0
END

COMPND    HMDB0240262
HETATM    1  C1  UNL     1      10.366   0.457  -0.961  1.00  0.00           C  
HETATM    2  C2  UNL     1       9.550  -0.517  -1.735  1.00  0.00           C  
HETATM    3  C3  UNL     1       8.976  -1.661  -1.026  1.00  0.00           C  
HETATM    4  C4  UNL     1       7.981  -1.597   0.017  1.00  0.00           C  
HETATM    5  C5  UNL     1       8.080  -0.975   1.324  1.00  0.00           C  
HETATM    6  C6  UNL     1       8.277   0.458   1.539  1.00  0.00           C  
HETATM    7  C7  UNL     1       7.224   1.345   0.901  1.00  0.00           C  
HETATM    8  C8  UNL     1       5.834   1.029   1.445  1.00  0.00           C  
HETATM    9  C9  UNL     1       4.881   1.967   0.740  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.446   1.769   1.180  1.00  0.00           C  
HETATM   11  C11 UNL     1       2.981   0.355   0.890  1.00  0.00           C  
HETATM   12  C12 UNL     1       3.068   0.060  -0.591  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.614  -1.330  -0.887  1.00  0.00           C  
HETATM   14  C14 UNL     1       1.182  -1.579  -0.475  1.00  0.00           C  
HETATM   15  C15 UNL     1       0.218  -0.661  -1.182  1.00  0.00           C  
HETATM   16  C16 UNL     1      -1.146  -0.975  -0.721  1.00  0.00           C  
HETATM   17  O1  UNL     1      -1.318  -1.879   0.123  1.00  0.00           O  
HETATM   18  O2  UNL     1      -2.209  -0.270  -1.226  1.00  0.00           O  
HETATM   19  C17 UNL     1      -3.554  -0.495  -0.848  1.00  0.00           C  
HETATM   20  C18 UNL     1      -4.411  -0.850  -2.047  1.00  0.00           C  
HETATM   21  O3  UNL     1      -4.336   0.230  -2.923  1.00  0.00           O  
HETATM   22  C19 UNL     1      -4.091   0.810  -0.301  1.00  0.00           C  
HETATM   23  O4  UNL     1      -5.437   0.654   0.097  1.00  0.00           O  
HETATM   24  P1  UNL     1      -5.949   2.134   0.683  1.00  0.00           P  
HETATM   25  O5  UNL     1      -5.099   2.466   1.899  1.00  0.00           O  
HETATM   26  O6  UNL     1      -5.754   3.370  -0.462  1.00  0.00           O1-
HETATM   27  O7  UNL     1      -7.554   1.997   1.186  1.00  0.00           O  
HETATM   28  C20 UNL     1      -8.114   0.903   0.529  1.00  0.00           C  
HETATM   29  C21 UNL     1      -9.549   0.794   0.990  1.00  0.00           C  
HETATM   30  N1  UNL     1     -10.245  -0.316   0.372  1.00  0.00           N1+
HETATM   31  C22 UNL     1     -11.666  -0.042   0.459  1.00  0.00           C  
HETATM   32  C23 UNL     1      -9.961  -1.571   1.036  1.00  0.00           C  
HETATM   33  C24 UNL     1      -9.899  -0.444  -1.022  1.00  0.00           C  
HETATM   34  H1  UNL     1      11.292   0.750  -1.548  1.00  0.00           H  
HETATM   35  H2  UNL     1       9.773   1.370  -0.733  1.00  0.00           H  
HETATM   36  H3  UNL     1      10.739   0.010  -0.027  1.00  0.00           H  
HETATM   37  H4  UNL     1       8.772   0.100  -2.279  1.00  0.00           H  
HETATM   38  H5  UNL     1      10.219  -0.855  -2.604  1.00  0.00           H  
HETATM   39  H6  UNL     1       8.541  -2.339  -1.869  1.00  0.00           H  
HETATM   40  H7  UNL     1       9.836  -2.337  -0.665  1.00  0.00           H  
HETATM   41  H8  UNL     1       7.720  -2.719   0.249  1.00  0.00           H  
HETATM   42  H9  UNL     1       6.938  -1.323  -0.450  1.00  0.00           H  
HETATM   43  H10 UNL     1       7.132  -1.258   1.912  1.00  0.00           H  
HETATM   44  H11 UNL     1       8.885  -1.506   1.934  1.00  0.00           H  
HETATM   45  H12 UNL     1       9.246   0.913   1.497  1.00  0.00           H  
HETATM   46  H13 UNL     1       8.018   0.604   2.682  1.00  0.00           H  
HETATM   47  H14 UNL     1       7.454   2.382   1.226  1.00  0.00           H  
HETATM   48  H15 UNL     1       7.253   1.336  -0.190  1.00  0.00           H  
HETATM   49  H16 UNL     1       5.860   1.292   2.523  1.00  0.00           H  
HETATM   50  H17 UNL     1       5.601  -0.031   1.286  1.00  0.00           H  
HETATM   51  H18 UNL     1       5.005   1.904  -0.340  1.00  0.00           H  
HETATM   52  H19 UNL     1       5.166   3.004   1.067  1.00  0.00           H  
HETATM   53  H20 UNL     1       2.832   2.456   0.561  1.00  0.00           H  
HETATM   54  H21 UNL     1       3.318   1.985   2.246  1.00  0.00           H  
HETATM   55  H22 UNL     1       3.593  -0.360   1.457  1.00  0.00           H  
HETATM   56  H23 UNL     1       1.919   0.294   1.211  1.00  0.00           H  
HETATM   57  H24 UNL     1       2.601   0.834  -1.204  1.00  0.00           H  
HETATM   58  H25 UNL     1       4.169   0.096  -0.840  1.00  0.00           H  
HETATM   59  H26 UNL     1       3.242  -2.032  -0.286  1.00  0.00           H  
HETATM   60  H27 UNL     1       2.725  -1.627  -1.935  1.00  0.00           H  
HETATM   61  H28 UNL     1       0.859  -2.614  -0.692  1.00  0.00           H  
HETATM   62  H29 UNL     1       1.018  -1.435   0.617  1.00  0.00           H  
HETATM   63  H30 UNL     1       0.218  -0.849  -2.295  1.00  0.00           H  
HETATM   64  H31 UNL     1       0.487   0.403  -1.013  1.00  0.00           H  
HETATM   65  H32 UNL     1      -3.691  -1.285  -0.110  1.00  0.00           H  
HETATM   66  H33 UNL     1      -4.160  -1.810  -2.496  1.00  0.00           H  
HETATM   67  H34 UNL     1      -5.464  -0.909  -1.679  1.00  0.00           H  
HETATM   68  H35 UNL     1      -3.435   0.651  -2.888  1.00  0.00           H  
HETATM   69  H36 UNL     1      -4.102   1.592  -1.097  1.00  0.00           H  
HETATM   70  H37 UNL     1      -3.489   1.216   0.522  1.00  0.00           H  
HETATM   71  H38 UNL     1      -8.032   0.988  -0.579  1.00  0.00           H  
HETATM   72  H39 UNL     1      -7.510   0.020   0.825  1.00  0.00           H  
HETATM   73  H40 UNL     1      -9.525   0.709   2.092  1.00  0.00           H  
HETATM   74  H41 UNL     1     -10.056   1.726   0.667  1.00  0.00           H  
HETATM   75  H42 UNL     1     -11.847   1.060   0.486  1.00  0.00           H  
HETATM   76  H43 UNL     1     -12.253  -0.504  -0.345  1.00  0.00           H  
HETATM   77  H44 UNL     1     -12.020  -0.421   1.462  1.00  0.00           H  
HETATM   78  H45 UNL     1      -8.990  -1.991   0.760  1.00  0.00           H  
HETATM   79  H46 UNL     1     -10.112  -1.469   2.123  1.00  0.00           H  
HETATM   80  H47 UNL     1     -10.743  -2.296   0.686  1.00  0.00           H  
HETATM   81  H48 UNL     1      -9.870   0.578  -1.485  1.00  0.00           H  
HETATM   82  H49 UNL     1     -10.647  -1.079  -1.547  1.00  0.00           H  
HETATM   83  H50 UNL     1      -8.874  -0.860  -1.104  1.00  0.00           H  
CONECT    1    2   34   35   36
CONECT    2    3   37   38
CONECT    3    4   39   40
CONECT    4    5   41   42
CONECT    5    6   43   44
CONECT    6    7   45   46
CONECT    7    8   47   48
CONECT    8    9   49   50
CONECT    9   10   51   52
CONECT   10   11   53   54
CONECT   11   12   55   56
CONECT   12   13   57   58
CONECT   13   14   59   60
CONECT   14   15   61   62
CONECT   15   16   63   64
CONECT   16   17   17   18
CONECT   18   19
CONECT   19   20   22   65
CONECT   20   21   66   67
CONECT   21   68
CONECT   22   23   69   70
CONECT   23   24
CONECT   24   25   25   26   27
CONECT   27   28
CONECT   28   29   71   72
CONECT   29   30   73   74
CONECT   30   31   32   33
CONECT   31   75   76   77
CONECT   32   78   79   80
CONECT   33   81   82   83
END

HMDB0240262
     RDKit          3D
LysoPC(0:0/16:0)
 83 82  0  0  0  0  0  0  0  0999 V2000
   10.3660    0.4572   -0.9607 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5500   -0.5166   -1.7354 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9763   -1.6608   -1.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9811   -1.5971    0.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0802   -0.9754    1.3236 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2774    0.4581    1.5393 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2236    1.3446    0.9012 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8344    1.0286    1.4449 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8810    1.9667    0.7400 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4456    1.7688    1.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9814    0.3551    0.8900 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0684    0.0600   -0.5910 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6138   -1.3296   -0.8873 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1821   -1.5794   -0.4755 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2184   -0.6611   -1.1820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1462   -0.9752   -0.7210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184   -1.8793    0.1230 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2095   -0.2699   -1.2258 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5537   -0.4953   -0.8480 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4106   -0.8503   -2.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3363    0.2296   -2.9231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0914    0.8097   -0.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4371    0.6543    0.0972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9491    2.1344    0.6827 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.0988    2.4663    1.8987 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7536    3.3703   -0.4615 O   0  0  0  0  0  1  0  0  0  0  0  0
   -7.5545    1.9968    1.1856 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1136    0.9030    0.5286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5494    0.7943    0.9897 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2448   -0.3162    0.3717 N   0  0  0  0  0  4  0  0  0  0  0  0
  -11.6663   -0.0420    0.4587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9607   -1.5707    1.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8991   -0.4438   -1.0220 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2925    0.7498   -1.5481 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7734    1.3703   -0.7333 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7390    0.0104   -0.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7722    0.1002   -2.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2191   -0.8547   -2.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5411   -2.3388   -1.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8358   -2.3370   -0.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7203   -2.7186    0.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9380   -1.3231   -0.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1316   -1.2581    1.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8846   -1.5063    1.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2463    0.9131    1.4965 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0179    0.6037    2.6817 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4539    2.3819    1.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2533    1.3355   -0.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8603    1.2925    2.5233 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6015   -0.0312    1.2862 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0052    1.9035   -0.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1659    3.0037    1.0671 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8322    2.4556    0.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3179    1.9852    2.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5927   -0.3599    1.4568 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9190    0.2935    1.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6011    0.8337   -1.2036 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1692    0.0958   -0.8398 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2417   -2.0315   -0.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7248   -1.6266   -1.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8593   -2.6145   -0.6921 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0179   -1.4350    0.6169 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2185   -0.8493   -2.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4872    0.4030   -1.0134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6911   -1.2849   -0.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1604   -1.8101   -2.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4635   -0.9090   -1.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4346    0.6511   -2.8885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1019    1.5919   -1.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4887    1.2164    0.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0316    0.9878   -0.5786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5103    0.0204    0.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5254    0.7090    2.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0562    1.7264    0.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8471    1.0605    0.4864 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2532   -0.5043   -0.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0199   -0.4207    1.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9897   -1.9913    0.7601 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1115   -1.4688    2.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7435   -2.2957    0.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8704    0.5778   -1.4845 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6474   -1.0788   -1.5473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8739   -0.8598   -1.1036 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  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 24 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 30 33  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  2 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  0
  4 42  1  0
  5 43  1  0
  5 44  1  0
  6 45  1  0
  6 46  1  0
  7 47  1  0
  7 48  1  0
  8 49  1  0
  8 50  1  0
  9 51  1  0
  9 52  1  0
 10 53  1  0
 10 54  1  0
 11 55  1  0
 11 56  1  0
 12 57  1  0
 12 58  1  0
 13 59  1  0
 13 60  1  0
 14 61  1  0
 14 62  1  0
 15 63  1  0
 15 64  1  0
 19 65  1  1
 20 66  1  0
 20 67  1  0
 21 68  1  0
 22 69  1  0
 22 70  1  0
 28 71  1  0
 28 72  1  0
 29 73  1  0
 29 74  1  0
 31 75  1  0
 31 76  1  0
 31 77  1  0
 32 78  1  0
 32 79  1  0
 32 80  1  0
 33 81  1  0
 33 82  1  0
 33 83  1  0
M  CHG  2  26  -1  30   1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2R)-3-Hydroxy-2-(palmitoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate	ChEBI
2-Hexadecanoyl-sn-glycero-3-phosphocholine	ChEBI
2-Palmitoyllysophosphatidylcholine	ChEBI
PC(0:0/16:0)	ChEBI
(2R)-3-Hydroxy-2-(palmitoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphoric acid	Generator
2-Palmitoyl-sn-glycero-3-phosphocholine	HMDB
2-Palmitoyl-lysophosphatidylcholine	HMDB
2-Palmitoyl-GPC	HMDB
LysoPC(16:0)	HMDB
LPC(0:0/16:0)	HMDB
LPC(16:0)	HMDB
Lysophosphatidylcholine(0:0/16:0)	HMDB
Lysophosphatidylcholine(16:0)	HMDB
2-Hexadecanoylglycerophosphocholine	HMDB
2-Palmitoylglycerophosphocholine	HMDB
GPC(0:0/16:0)	HMDB
GPC(16:0)	HMDB
LysoPC(0:0/16:0)	SMPDB

Chemical Formula

C₂₄H₅₀NO₇P

Average Molecular Weight

495.638

Monoisotopic Molecular Weight

495.332489952

IUPAC Name

(2-{[(2R)-2-(hexadecanoyloxy)-3-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-2-(hexadecanoyloxy)-3-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

66757-27-5

SMILES

CCCCCCCCCCCCCCCC(=O)O[C@H](CO)COP([O-])(=O)OCC[N+](C)(C)C

InChI Identifier

InChI=1S/C24H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-24(27)32-23(21-26)22-31-33(28,29)30-20-19-25(2,3)4/h23,26H,5-22H2,1-4H3/t23-/m1/s1

InChI Key

NEGQHKSYEYVFTD-HSZRJFAPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-2 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

2-acyl-sn-glycero-3-phosphocholines

Alternative Parents

Substituents

2-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
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Alcohol
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Primary alcohol
Carbonyl group
Organic salt
Amine
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

lysophosphatidylcholine 16:0 (CHEBI:76078 )
Monoacylglycerophosphocholines (LMGP01050074 )

Ontology

Not Available

Physical Properties

State

Not Available

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
logP	1.82	ALOGPS
logP	1.19	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	105.12 Å²	ChemAxon
Rotatable Bond Count	24	ChemAxon
Refractivity	142.27 m³·mol⁻¹	ChemAxon
Polarizability	57.51 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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
AllCCS	[M+H]+	232.324	31661259
AllCCS	[M-H]-	227.405	31661259
DeepCCS	[M+H]+	226.98	30932474
DeepCCS	[M-H]-	224.622	30932474
DeepCCS	[M-2H]-	257.818	30932474
DeepCCS	[M+Na]+	234.326	30932474
AllCCS	[M+H]+	232.3	32859911
AllCCS	[M+H-H2O]+	230.9	32859911
AllCCS	[M+NH4]+	233.6	32859911
AllCCS	[M+Na]+	233.9	32859911
AllCCS	[M-H]-	227.4	32859911
AllCCS	[M+Na-2H]-	229.7	32859911
AllCCS	[M+HCOO]-	232.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
LysoPC(0:0/16:0)	CCCCCCCCCCCCCCCC(=O)O[C@H](CO)COP([O-])(=O)OCC[N+](C)(C)C	3310.1	Standard polar	33892256
LysoPC(0:0/16:0)	CCCCCCCCCCCCCCCC(=O)O[C@H](CO)COP([O-])(=O)OCC[N+](C)(C)C	3026.9	Standard non polar	33892256
LysoPC(0:0/16:0)	CCCCCCCCCCCCCCCC(=O)O[C@H](CO)COP([O-])(=O)OCC[N+](C)(C)C	3288.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
LysoPC(0:0/16:0),1TMS,isomer #1	CCCCCCCCCCCCCCCC(=O)O[C@H](CO[Si](C)(C)C)COP(=O)([O-])OCC[N+](C)(C)C	3286.4	Semi standard non polar	33892256
LysoPC(0:0/16:0),1TBDMS,isomer #1	CCCCCCCCCCCCCCCC(=O)O[C@H](CO[Si](C)(C)C(C)(C)C)COP(=O)([O-])OCC[N+](C)(C)C	3511.0	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(0:0/16:0) GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - LysoPC(0:0/16:0) GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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(0:0/16:0) 10V, Negative-QTOF	splash10-0006-0000900000-ab76377748e00cb850aa	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(0:0/16:0) 20V, Negative-QTOF	splash10-0a4l-0090800000-a495b2c1cebc3a7c5560	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(0:0/16:0) 40V, Negative-QTOF	splash10-0a6r-8391100000-957a6acd6e614a28f0a0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(0:0/16:0) 10V, Positive-QTOF	splash10-0002-1000900000-bae518f53efb0b12c62e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(0:0/16:0) 20V, Positive-QTOF	splash10-001i-2910200000-30991885dd296ae276a6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(0:0/16:0) 40V, Positive-QTOF	splash10-00dr-6900000000-90fa6616e6a4927b9b0f	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

21403165

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15061532

PDB ID

Not Available

ChEBI ID

76078

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 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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.

Enzymes

Enzyme Details

1. 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

2. 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

3. 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

Enzyme Details

4. G-protein coupled receptor 4

General function:: Not Available
Specific function:: Proton-sensing G-protein coupled receptor couples to multiple intracellular signaling pathways, including GNAS/cAMP, GNAQ/phospholipase C (PLC), and GNA12/GNA13/Rho pathways. Acidosis-induced GPR4 activation increases paracellular gap formation and permeability of vascular endothelial cells through the GNA12/GNA13/Rho GTPase signaling pathway. In the brain may mediate central respiratory sensitivity to CO2H+.
Gene Name:: GPR4
Uniprot ID:: P46093
Molecular weight:: 40.0

Showing metabocard for LysoPC(0:0/16:0) (HMDB0240262)

MOL for HMDB0240262 (LysoPC(0:0/16:0))

3D MOL for HMDB0240262 (LysoPC(0:0/16:0))

3D SDF for HMDB0240262 (LysoPC(0:0/16:0))

3D-SDF for HMDB0240262 (LysoPC(0:0/16:0))

PDB for HMDB0240262 (LysoPC(0:0/16:0))

3D PDB for HMDB0240262 (LysoPC(0:0/16:0))

SMILES for HMDB0240262 (LysoPC(0:0/16:0))

INCHI for HMDB0240262 (LysoPC(0:0/16:0))

Structure for HMDB0240262 (LysoPC(0:0/16:0))

3D Structure for HMDB0240262 (LysoPC(0:0/16:0))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes