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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 13:19:53 UTC

Update Date

2022-07-14 16:57:34 UTC

HMDB ID

HMDB0010379

Secondary Accession Numbers

HMDB10379

Metabolite Identification

Common Name

LysoPC(14:0/0:0)

Description

LysoPC(14:0/0:0) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) position. Fatty acids containing 16, 18 and 20 carbons are the most common. LysoPC(14:0/0:0), in particular, consists of one chain of myristic acid at the C-1 position. The myristic acid moiety is derived from nutmeg and butter. 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

LysoPC(14:0/0:0)
  Mrv1652311211901002D          

 31 30  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
   19.0896   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0896   -5.3449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3755   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6614   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9472   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2331   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5190   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8049   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0908   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3766   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6625   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9484   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2343   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5202   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8060   -6.5294    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
 15 17  1  0  0  0  0
 10 12  1  0  0  0  0
 13 16  1  6  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
M  CHG  2   6   1  11  -1
M  END

HMDB0010379
     RDKit          3D
LysoPC(14:0/0:0)
 77 76  0  0  0  0  0  0  0  0999 V2000
   10.8600    0.7561    2.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0351    0.6160    0.9871 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4924    1.9647    0.6664 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6948    2.1163   -0.5419 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4093    1.4464   -0.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2984   -0.0131   -0.8090 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8460   -0.3982   -1.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8758    0.0863   -0.1864 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4244   -0.3063   -0.5909 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3344   -1.7642   -0.6917 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0317   -2.3963   -0.9270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2041   -2.1131   -2.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5970   -0.7558   -2.1545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2760   -0.6130   -0.9336 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0979    0.1088   -0.0070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4775   -1.2964   -0.8740 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3234   -1.2086    0.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8071    0.1832    0.4969 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5164    0.5843   -0.6359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8179    0.1631    1.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7844   -0.7516    1.2974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0021   -0.9694    2.4127 P   0  0  0  0  0  5  0  0  0  0  0  0
   -6.1427   -2.4794    2.6350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4930   -0.3425    3.9029 O   0  0  0  0  0  1  0  0  0  0  0  0
   -7.4919   -0.4017    1.9355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4402    0.8537    1.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7774    1.3606    0.9226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4317    0.5150   -0.0476 N   0  0  0  0  0  4  0  0  0  0  0  0
  -10.0832   -0.6112    0.6166 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4658    1.2333   -0.7624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5201   -0.0385   -1.0281 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4504   -0.1618    2.3683 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4816    1.6565    2.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1225    0.8053    3.1304 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7992    0.3062    0.2169 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2766   -0.1384    1.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0357    2.4526    1.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4250    2.6221    0.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4106    1.9052   -1.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4994    3.2356   -0.7422 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6203    1.8271   -0.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0187    1.8319   -1.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3560   -0.4973    0.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9373   -0.5541   -1.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7963   -1.5130   -1.2389 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6845    0.0538   -2.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8500    1.2105   -0.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0383   -0.3000    0.8289 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7500    0.1017    0.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3215    0.1887   -1.6049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7349   -2.1948    0.2860 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0472   -2.1502   -1.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2286   -3.5343   -0.8785 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4207   -2.2788    0.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3297   -2.8414   -2.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7350   -2.3246   -3.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3116    0.0226   -2.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1035   -0.6883   -3.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1825   -1.9039    0.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8194   -1.6636    1.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9708    0.8550    0.7221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7034   -0.1455   -1.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1765    1.1789    1.8314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2654   -0.2847    2.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9847    1.5918    2.0197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8027    0.7740    0.4348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4847    1.5004    1.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6373    2.3579    0.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3881   -1.4685    0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2464   -0.3409    1.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0654   -0.8509    0.1421 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4595    1.0214   -1.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2663    2.3260   -0.6654 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4826    1.0552   -0.3869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1512   -0.5352   -1.7931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9770    0.7767   -1.5326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8647   -0.8151   -0.6053 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  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 22 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 28 31  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
  5 42  1  0
  6 43  1  0
  6 44  1  0
  7 45  1  0
  7 46  1  0
  8 47  1  0
  8 48  1  0
  9 49  1  0
  9 50  1  0
 10 51  1  0
 10 52  1  0
 11 53  1  0
 11 54  1  0
 12 55  1  0
 12 56  1  0
 13 57  1  0
 13 58  1  0
 17 59  1  0
 17 60  1  0
 18 61  1  1
 19 62  1  0
 20 63  1  0
 20 64  1  0
 26 65  1  0
 26 66  1  0
 27 67  1  0
 27 68  1  0
 29 69  1  0
 29 70  1  0
 29 71  1  0
 30 72  1  0
 30 73  1  0
 30 74  1  0
 31 75  1  0
 31 76  1  0
 31 77  1  0
M  CHG  2  24  -1  28   1
M  END

LysoPC(14:0/0:0)
  Mrv1652311211901002D          

 31 30  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
   19.0896   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0896   -5.3449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3755   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6614   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9472   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2331   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5190   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8049   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0908   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3766   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6625   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9484   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2343   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5202   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8060   -6.5294    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
 15 17  1  0  0  0  0
 10 12  1  0  0  0  0
 13 16  1  6  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
M  CHG  2   6   1  11  -1
M  END
> <DATABASE_ID>
HMDB0010379

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H46NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-22(25)28-19-21(24)20-30-31(26,27)29-18-17-23(2,3)4/h21,24H,5-20H2,1-4H3/t21-/m1/s1

> <INCHI_KEY>
VXUOFDJKYGDUJI-OAQYLSRUSA-N

> <FORMULA>
C22H46NO7P

> <MOLECULAR_WEIGHT>
467.5769

> <EXACT_MASS>
467.301189343

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
53.74482361489388

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{[(2R)-2-hydroxy-3-(tetradecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium

> <ALOGPS_LOGP>
1.10

> <JCHEM_LOGP>
0.30360514686158746

> <ALOGPS_LOGS>
-5.84

> <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>
105.12000000000002

> <JCHEM_REFRACTIVITY>
133.07169999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.52e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-{[(2R)-2-hydroxy-3-(tetradecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0010379
     RDKit          3D
LysoPC(14:0/0:0)
 77 76  0  0  0  0  0  0  0  0999 V2000
   10.8600    0.7561    2.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0351    0.6160    0.9871 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4924    1.9647    0.6664 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6948    2.1163   -0.5419 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4093    1.4464   -0.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2984   -0.0131   -0.8090 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8460   -0.3982   -1.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8758    0.0863   -0.1864 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4244   -0.3063   -0.5909 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3344   -1.7642   -0.6917 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0317   -2.3963   -0.9270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2041   -2.1131   -2.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5970   -0.7558   -2.1545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2760   -0.6130   -0.9336 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0979    0.1088   -0.0070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4775   -1.2964   -0.8740 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3234   -1.2086    0.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8071    0.1832    0.4969 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5164    0.5843   -0.6359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8179    0.1631    1.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7844   -0.7516    1.2974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0021   -0.9694    2.4127 P   0  0  0  0  0  5  0  0  0  0  0  0
   -6.1427   -2.4794    2.6350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4930   -0.3425    3.9029 O   0  0  0  0  0  1  0  0  0  0  0  0
   -7.4919   -0.4017    1.9355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4402    0.8537    1.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7774    1.3606    0.9226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4317    0.5150   -0.0476 N   0  0  0  0  0  4  0  0  0  0  0  0
  -10.0832   -0.6112    0.6166 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4658    1.2333   -0.7624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5201   -0.0385   -1.0281 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4504   -0.1618    2.3683 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4816    1.6565    2.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1225    0.8053    3.1304 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7992    0.3062    0.2169 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2766   -0.1384    1.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0357    2.4526    1.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4250    2.6221    0.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4106    1.9052   -1.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4994    3.2356   -0.7422 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6203    1.8271   -0.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0187    1.8319   -1.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3560   -0.4973    0.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9373   -0.5541   -1.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7963   -1.5130   -1.2389 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6845    0.0538   -2.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8500    1.2105   -0.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0383   -0.3000    0.8289 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7500    0.1017    0.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3215    0.1887   -1.6049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7349   -2.1948    0.2860 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0472   -2.1502   -1.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2286   -3.5343   -0.8785 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4207   -2.2788    0.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3297   -2.8414   -2.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7350   -2.3246   -3.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3116    0.0226   -2.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1035   -0.6883   -3.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1825   -1.9039    0.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8194   -1.6636    1.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9708    0.8550    0.7221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7034   -0.1455   -1.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1765    1.1789    1.8314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2654   -0.2847    2.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9847    1.5918    2.0197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8027    0.7740    0.4348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4847    1.5004    1.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6373    2.3579    0.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3881   -1.4685    0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2464   -0.3409    1.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0654   -0.8509    0.1421 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4595    1.0214   -1.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2663    2.3260   -0.6654 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4826    1.0552   -0.3869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1512   -0.5352   -1.7931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9770    0.7767   -1.5326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8647   -0.8151   -0.6053 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  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 22 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 28 31  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
  5 42  1  0
  6 43  1  0
  6 44  1  0
  7 45  1  0
  7 46  1  0
  8 47  1  0
  8 48  1  0
  9 49  1  0
  9 50  1  0
 10 51  1  0
 10 52  1  0
 11 53  1  0
 11 54  1  0
 12 55  1  0
 12 56  1  0
 13 57  1  0
 13 58  1  0
 17 59  1  0
 17 60  1  0
 18 61  1  1
 19 62  1  0
 20 63  1  0
 20 64  1  0
 26 65  1  0
 26 66  1  0
 27 67  1  0
 27 68  1  0
 29 69  1  0
 29 70  1  0
 29 71  1  0
 30 72  1  0
 30 73  1  0
 30 74  1  0
 31 75  1  0
 31 76  1  0
 31 77  1  0
M  CHG  2  24  -1  28   1
M  END

HEADER    PROTEIN                                 21-NOV-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: LysoPC(14:0/0:0)                                  
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      35.634 -11.417   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      35.634  -9.977   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      34.301 -12.188   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      32.968 -11.417   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      31.635 -12.188   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      30.302 -11.417   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      28.969 -12.188   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      27.636 -11.417   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      26.303 -12.188   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      24.970 -11.417   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      23.637 -12.188   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      22.304 -11.417   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      20.971 -12.188   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      19.638 -11.417   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      18.305 -12.188   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   17                                                       
CONECT   16   13                                                            
CONECT   17   15   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                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   60    0
END

COMPND    HMDB0010379
HETATM    1  C1  UNL     1      10.860   0.756   2.279  1.00  0.00           C  
HETATM    2  C2  UNL     1      10.035   0.616   0.987  1.00  0.00           C  
HETATM    3  C3  UNL     1       9.492   1.965   0.666  1.00  0.00           C  
HETATM    4  C4  UNL     1       8.695   2.116  -0.542  1.00  0.00           C  
HETATM    5  C5  UNL     1       7.409   1.446  -0.771  1.00  0.00           C  
HETATM    6  C6  UNL     1       7.298  -0.013  -0.809  1.00  0.00           C  
HETATM    7  C7  UNL     1       5.846  -0.398  -1.196  1.00  0.00           C  
HETATM    8  C8  UNL     1       4.876   0.086  -0.186  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.424  -0.306  -0.591  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.334  -1.764  -0.692  1.00  0.00           C  
HETATM   11  C11 UNL     1       2.032  -2.396  -0.927  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.204  -2.113  -2.091  1.00  0.00           C  
HETATM   13  C13 UNL     1       0.597  -0.756  -2.155  1.00  0.00           C  
HETATM   14  C14 UNL     1      -0.276  -0.613  -0.934  1.00  0.00           C  
HETATM   15  O1  UNL     1       0.098   0.109  -0.007  1.00  0.00           O  
HETATM   16  O2  UNL     1      -1.478  -1.296  -0.874  1.00  0.00           O  
HETATM   17  C15 UNL     1      -2.323  -1.209   0.239  1.00  0.00           C  
HETATM   18  C16 UNL     1      -2.807   0.183   0.497  1.00  0.00           C  
HETATM   19  O3  UNL     1      -3.516   0.584  -0.636  1.00  0.00           O  
HETATM   20  C17 UNL     1      -3.818   0.163   1.657  1.00  0.00           C  
HETATM   21  O4  UNL     1      -4.784  -0.752   1.297  1.00  0.00           O  
HETATM   22  P1  UNL     1      -6.002  -0.969   2.413  1.00  0.00           P  
HETATM   23  O5  UNL     1      -6.143  -2.479   2.635  1.00  0.00           O  
HETATM   24  O6  UNL     1      -5.493  -0.343   3.903  1.00  0.00           O1-
HETATM   25  O7  UNL     1      -7.492  -0.402   1.935  1.00  0.00           O  
HETATM   26  C18 UNL     1      -7.440   0.854   1.349  1.00  0.00           C  
HETATM   27  C19 UNL     1      -8.777   1.361   0.923  1.00  0.00           C  
HETATM   28  N1  UNL     1      -9.432   0.515  -0.048  1.00  0.00           N1+
HETATM   29  C20 UNL     1     -10.083  -0.611   0.617  1.00  0.00           C  
HETATM   30  C21 UNL     1     -10.466   1.233  -0.762  1.00  0.00           C  
HETATM   31  C22 UNL     1      -8.520  -0.038  -1.028  1.00  0.00           C  
HETATM   32  H1  UNL     1      11.450  -0.162   2.368  1.00  0.00           H  
HETATM   33  H2  UNL     1      11.482   1.656   2.224  1.00  0.00           H  
HETATM   34  H3  UNL     1      10.122   0.805   3.130  1.00  0.00           H  
HETATM   35  H4  UNL     1      10.799   0.306   0.217  1.00  0.00           H  
HETATM   36  H5  UNL     1       9.277  -0.138   1.127  1.00  0.00           H  
HETATM   37  H6  UNL     1       9.036   2.453   1.580  1.00  0.00           H  
HETATM   38  H7  UNL     1      10.425   2.622   0.522  1.00  0.00           H  
HETATM   39  H8  UNL     1       9.411   1.905  -1.427  1.00  0.00           H  
HETATM   40  H9  UNL     1       8.499   3.236  -0.742  1.00  0.00           H  
HETATM   41  H10 UNL     1       6.620   1.827  -0.056  1.00  0.00           H  
HETATM   42  H11 UNL     1       7.019   1.832  -1.772  1.00  0.00           H  
HETATM   43  H12 UNL     1       7.356  -0.497   0.224  1.00  0.00           H  
HETATM   44  H13 UNL     1       7.937  -0.554  -1.518  1.00  0.00           H  
HETATM   45  H14 UNL     1       5.796  -1.513  -1.239  1.00  0.00           H  
HETATM   46  H15 UNL     1       5.685   0.054  -2.180  1.00  0.00           H  
HETATM   47  H16 UNL     1       4.850   1.210  -0.073  1.00  0.00           H  
HETATM   48  H17 UNL     1       5.038  -0.300   0.829  1.00  0.00           H  
HETATM   49  H18 UNL     1       2.750   0.102   0.152  1.00  0.00           H  
HETATM   50  H19 UNL     1       3.321   0.189  -1.605  1.00  0.00           H  
HETATM   51  H20 UNL     1       3.735  -2.195   0.286  1.00  0.00           H  
HETATM   52  H21 UNL     1       4.047  -2.150  -1.517  1.00  0.00           H  
HETATM   53  H22 UNL     1       2.229  -3.534  -0.878  1.00  0.00           H  
HETATM   54  H23 UNL     1       1.421  -2.279   0.043  1.00  0.00           H  
HETATM   55  H24 UNL     1       0.330  -2.841  -2.104  1.00  0.00           H  
HETATM   56  H25 UNL     1       1.735  -2.325  -3.069  1.00  0.00           H  
HETATM   57  H26 UNL     1       1.312   0.023  -2.292  1.00  0.00           H  
HETATM   58  H27 UNL     1      -0.103  -0.688  -3.054  1.00  0.00           H  
HETATM   59  H28 UNL     1      -3.183  -1.904   0.021  1.00  0.00           H  
HETATM   60  H29 UNL     1      -1.819  -1.664   1.120  1.00  0.00           H  
HETATM   61  H30 UNL     1      -1.971   0.855   0.722  1.00  0.00           H  
HETATM   62  H31 UNL     1      -3.703  -0.146  -1.256  1.00  0.00           H  
HETATM   63  H32 UNL     1      -4.177   1.179   1.831  1.00  0.00           H  
HETATM   64  H33 UNL     1      -3.265  -0.285   2.515  1.00  0.00           H  
HETATM   65  H34 UNL     1      -6.985   1.592   2.020  1.00  0.00           H  
HETATM   66  H35 UNL     1      -6.803   0.774   0.435  1.00  0.00           H  
HETATM   67  H36 UNL     1      -9.485   1.500   1.764  1.00  0.00           H  
HETATM   68  H37 UNL     1      -8.637   2.358   0.460  1.00  0.00           H  
HETATM   69  H38 UNL     1      -9.388  -1.468   0.591  1.00  0.00           H  
HETATM   70  H39 UNL     1     -10.246  -0.341   1.681  1.00  0.00           H  
HETATM   71  H40 UNL     1     -11.065  -0.851   0.142  1.00  0.00           H  
HETATM   72  H41 UNL     1     -10.460   1.021  -1.849  1.00  0.00           H  
HETATM   73  H42 UNL     1     -10.266   2.326  -0.665  1.00  0.00           H  
HETATM   74  H43 UNL     1     -11.483   1.055  -0.387  1.00  0.00           H  
HETATM   75  H44 UNL     1      -9.151  -0.535  -1.793  1.00  0.00           H  
HETATM   76  H45 UNL     1      -7.977   0.777  -1.533  1.00  0.00           H  
HETATM   77  H46 UNL     1      -7.865  -0.815  -0.605  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3   35   36
CONECT    3    4   37   38
CONECT    4    5   39   40
CONECT    5    6   41   42
CONECT    6    7   43   44
CONECT    7    8   45   46
CONECT    8    9   47   48
CONECT    9   10   49   50
CONECT   10   11   51   52
CONECT   11   12   53   54
CONECT   12   13   55   56
CONECT   13   14   57   58
CONECT   14   15   15   16
CONECT   16   17
CONECT   17   18   59   60
CONECT   18   19   20   61
CONECT   19   62
CONECT   20   21   63   64
CONECT   21   22
CONECT   22   23   23   24   25
CONECT   25   26
CONECT   26   27   65   66
CONECT   27   28   67   68
CONECT   28   29   30   31
CONECT   29   69   70   71
CONECT   30   72   73   74
CONECT   31   75   76   77
END

HMDB0010379
     RDKit          3D
LysoPC(14:0/0:0)
 77 76  0  0  0  0  0  0  0  0999 V2000
   10.8600    0.7561    2.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0351    0.6160    0.9871 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4924    1.9647    0.6664 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6948    2.1163   -0.5419 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4093    1.4464   -0.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2984   -0.0131   -0.8090 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8460   -0.3982   -1.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8758    0.0863   -0.1864 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4244   -0.3063   -0.5909 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3344   -1.7642   -0.6917 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0317   -2.3963   -0.9270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2041   -2.1131   -2.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5970   -0.7558   -2.1545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2760   -0.6130   -0.9336 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0979    0.1088   -0.0070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4775   -1.2964   -0.8740 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3234   -1.2086    0.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8071    0.1832    0.4969 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5164    0.5843   -0.6359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8179    0.1631    1.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7844   -0.7516    1.2974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0021   -0.9694    2.4127 P   0  0  0  0  0  5  0  0  0  0  0  0
   -6.1427   -2.4794    2.6350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4930   -0.3425    3.9029 O   0  0  0  0  0  1  0  0  0  0  0  0
   -7.4919   -0.4017    1.9355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4402    0.8537    1.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7774    1.3606    0.9226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4317    0.5150   -0.0476 N   0  0  0  0  0  4  0  0  0  0  0  0
  -10.0832   -0.6112    0.6166 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4658    1.2333   -0.7624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5201   -0.0385   -1.0281 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4504   -0.1618    2.3683 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4816    1.6565    2.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1225    0.8053    3.1304 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7992    0.3062    0.2169 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2766   -0.1384    1.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0357    2.4526    1.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4250    2.6221    0.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4106    1.9052   -1.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4994    3.2356   -0.7422 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6203    1.8271   -0.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0187    1.8319   -1.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3560   -0.4973    0.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9373   -0.5541   -1.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7963   -1.5130   -1.2389 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6845    0.0538   -2.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8500    1.2105   -0.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0383   -0.3000    0.8289 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7500    0.1017    0.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3215    0.1887   -1.6049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7349   -2.1948    0.2860 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0472   -2.1502   -1.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2286   -3.5343   -0.8785 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4207   -2.2788    0.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3297   -2.8414   -2.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7350   -2.3246   -3.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3116    0.0226   -2.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1035   -0.6883   -3.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1825   -1.9039    0.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8194   -1.6636    1.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9708    0.8550    0.7221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7034   -0.1455   -1.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1765    1.1789    1.8314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2654   -0.2847    2.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9847    1.5918    2.0197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8027    0.7740    0.4348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4847    1.5004    1.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6373    2.3579    0.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3881   -1.4685    0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2464   -0.3409    1.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0654   -0.8509    0.1421 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4595    1.0214   -1.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2663    2.3260   -0.6654 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4826    1.0552   -0.3869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1512   -0.5352   -1.7931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9770    0.7767   -1.5326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8647   -0.8151   -0.6053 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  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 22 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 28 31  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
  5 42  1  0
  6 43  1  0
  6 44  1  0
  7 45  1  0
  7 46  1  0
  8 47  1  0
  8 48  1  0
  9 49  1  0
  9 50  1  0
 10 51  1  0
 10 52  1  0
 11 53  1  0
 11 54  1  0
 12 55  1  0
 12 56  1  0
 13 57  1  0
 13 58  1  0
 17 59  1  0
 17 60  1  0
 18 61  1  1
 19 62  1  0
 20 63  1  0
 20 64  1  0
 26 65  1  0
 26 66  1  0
 27 67  1  0
 27 68  1  0
 29 69  1  0
 29 70  1  0
 29 71  1  0
 30 72  1  0
 30 73  1  0
 30 74  1  0
 31 75  1  0
 31 76  1  0
 31 77  1  0
M  CHG  2  24  -1  28   1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-C14:0-Lysophosphatidylcholine betaine	ChEBI
1-Myristoyl-glycero-3-phosphocholine	ChEBI
1-Myristoyl-sn-glycero-3-phosphocholine betaine	ChEBI
1-Tetradecanoyl-sn-glycero-3-phosphocholine	ChEBI
1-Tetradecanoyl-sn-glycero-3-phosphocholine betaine	ChEBI
LPC(14:0)	ChEBI
LPC(14:0/0:0)	ChEBI
LyPC(14:0)	ChEBI
LyPC(14:0/0:0)	ChEBI
Lysophosphatidylcholine(14:0/0:0)	ChEBI
PC(14:0/0:0)	ChEBI
LysoPC(14:0/0:0)	Lipid Annotator, ChEBI
Lysophosphatidylcholine(14:0)	Lipid Annotator, HMDB
1-tetradecanoyl-glycero-3-phosphocholine	Lipid Annotator, HMDB
LysoPC(14:0)	Lipid Annotator, HMDB
1-Myristoylglycerophosphocholine	HMDB
1-Tetradecanoylglycerophosphocholine	HMDB
1-Myristoyl-GPC	HMDB
1-Myristoyl-lysophosphatidylcholine	HMDB
1-Myristoyl-sn-glycero-3-phosphocholine	HMDB
GPC(14:0)	HMDB
GPC(14:0/0:0)	HMDB

Chemical Formula

C₂₂H₄₆NO₇P

Average Molecular Weight

467.5769

Monoisotopic Molecular Weight

467.301189343

IUPAC Name

(2-{[(2R)-2-hydroxy-3-(tetradecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-2-hydroxy-3-(tetradecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

20559-16-4

SMILES

CCCCCCCCCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C

InChI Identifier

InChI=1S/C22H46NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-22(25)28-19-21(24)20-30-31(26,27)29-18-17-23(2,3)4/h21,24H,5-20H2,1-4H3/t21-/m1/s1

InChI Key

VXUOFDJKYGDUJI-OAQYLSRUSA-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

1-O-acyl-sn-glycero-3-phosphocholine (CHEBI:64489 )
lysophosphatidylcholine 14:0 (CHEBI:64489 )
Monoacylglycerophosphocholines (LMGP01050012 )

Ontology

Physiological effect

Health effect

Nervous system disorder

Central nervous system disorder

Alzheimer's Disease (PMID: 30845751)

Renal system and urinary system

Renal disorder

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

Cancer

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

Digestive system disorder

Gastrointestinal disorder

Stomach cancer (PMID: 26162894)

Organoleptic effect

Touch

Smooth (HMDB: HMDB0010379)

Disposition

Biological location

Cell membrane (HMDB: HMDB0010379)
Intracellular membrane (HMDB: HMDB0010379)

Biofluid or Excreta

Excreta

Feces (PMID: 27624970)
Urine (PMID: 32340350)

Non-excretory biofluid

Blood (PMID: 18953024)
Saliva (HMDB: HMDB0010379)

Tissue substructure

All tissues (HMDB: HMDB0010379)

Tissue

All Tissues (HMDB: HMDB0010379)

Cellular substructure

Cell

All cells and tissues (HMDB: HMDB0010379)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0010379)

Source

Endogenous

Endogenous (HMDB: HMDB0010379)

Animal

Animal (HMDB: HMDB0010379)

Exogenous

Food

Food (HMDB: HMDB0010379)

Animal origin

Lagomorph

Poultry

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

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Arachidonic Acid Metabolism (HMDB: HMDB0010379)
Lysolipid Incorporation into Mitochondria (PathBank: SMP0002424)
Lysolipid Incorporation into ER (PathBank: SMP0002425)
Lysolipid Incorporation into ER PC(14:0/14:0) (PathBank: SMP0002513)
Lysolipid Incorporation into ER PC(16:1(11Z)/16:1(11Z)) (PathBank: SMP0002516)
Lysolipid Incorporation into ER PC(18:2(9Z,11Z)/18:2(9Z,11Z)) (PathBank: SMP0002519)
Lysolipid Incorporation into Mitochondria PC(14:0/14:0) (PathBank: SMP0002522)
Lysolipid Incorporation into Mitochondria PC(16:1(11Z)/16:1(11Z)) (PathBank: SMP0002524)
Lysolipid Incorporation into Mitochondria PC(18:2(9Z,11Z)/18:2(9Z,11Z)) (PathBank: SMP0002527)

Signaling pathway

Apoptosis (PMID: 30845751)

Acetaminophen Action Pathway (HMDB: HMDB0010379)

Disease pathway

Leukotriene C4 Synthesis Deficiency (PathBank: SMP0000353)

Drug action pathway

Piroxicam Action Pathway (PathBank: SMP0000077)
Acetylsalicylic Acid Action Pathway (PathBank: SMP0000083)
Etodolac Action Pathway (PathBank: SMP0000084)
Ketoprofen Action Pathway (PathBank: SMP0000085)
Ibuprofen Action Pathway (PathBank: SMP0000086)
Rofecoxib Action Pathway (PathBank: SMP0000087)
Diclofenac Action Pathway (PathBank: SMP0000093)
Sulindac Action Pathway (PathBank: SMP0000094)
Celecoxib Action Pathway (PathBank: SMP0000096)
Ketorolac Action Pathway (PathBank: SMP0000098)
Suprofen Action Pathway (PathBank: SMP0000101)
Bromfenac Action Pathway (PathBank: SMP0000102)
Indomethacin Action Pathway (PathBank: SMP0000104)
Mefenamic Acid Action Pathway (PathBank: SMP0000109)
Oxaprozin Action Pathway (PathBank: SMP0000113)
Nabumetone Action Pathway (PathBank: SMP0000114)
Naproxen Action Pathway (PathBank: SMP0000120)
Diflunisal Action Pathway (PathBank: SMP0000289)
Meloxicam Action Pathway (PathBank: SMP0000106)
Valdecoxib Action Pathway (PathBank: SMP0000116)
Antipyrine Action Pathway (PathBank: SMP0000692)
Antrafenine Action Pathway (PathBank: SMP0000693)
Carprofen Action Pathway (PathBank: SMP0000694)
Etoricoxib Action Pathway (PathBank: SMP0000695)
Fenoprofen Action Pathway (PathBank: SMP0000696)
Flurbiprofen Action Pathway (PathBank: SMP0000697)
Magnesium Salicylate Action Pathway (PathBank: SMP0000698)
Lumiracoxib Action Pathway (PathBank: SMP0000699)
Lornoxicam Action Pathway (PathBank: SMP0000700)
Phenylbutazone Action Pathway (PathBank: SMP0000701)
Nepafenac Action Pathway (PathBank: SMP0000702)
Trisalicylate-Choline Action Pathway (PathBank: SMP0000703)
Tolmetin Action Pathway (PathBank: SMP0000704)
Tiaprofenic Acid Action Pathway (PathBank: SMP0000705)
Tenoxicam Action Pathway (PathBank: SMP0000706)
Salsalate Action Pathway (PathBank: SMP0000707)
Salicylate-Sodium Action Pathway (PathBank: SMP0000708)
Salicylic Acid Action Pathway (PathBank: SMP0000709)
Acetaminophen Action Pathway (PathBank: SMP0000710)

Cellular process

Apoptosis (PMID: 30845751)
Cell signaling (HMDB: HMDB0010379)

Chemical reaction

Lipid peroxidation (HMDB: HMDB0010379)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0010379)

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	222.0	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001987

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00075 g/L	ALOGPS
logP	1.1	ALOGPS
logP	0.3	ChemAxon
logS	-5.8	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	22	ChemAxon
Refractivity	133.07 m³·mol⁻¹	ChemAxon
Polarizability	53.74 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
DeepCCS	[M+H]+	222.258	30932474
DeepCCS	[M-H]-	219.9	30932474
DeepCCS	[M-2H]-	252.781	30932474
DeepCCS	[M+Na]+	229.23	30932474
AllCCS	[M+H]+	223.7	32859911
AllCCS	[M+H-H2O]+	222.2	32859911
AllCCS	[M+NH4]+	225.1	32859911
AllCCS	[M+Na]+	225.5	32859911
AllCCS	[M-H]-	220.4	32859911
AllCCS	[M+Na-2H]-	222.4	32859911
AllCCS	[M+HCOO]-	224.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
LysoPC(14:0/0:0)	CCCCCCCCCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C	3370.6	Standard polar	33892256
LysoPC(14:0/0:0)	CCCCCCCCCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C	2842.2	Standard non polar	33892256
LysoPC(14:0/0:0)	CCCCCCCCCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C	3120.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
LysoPC(14:0/0:0),1TMS,isomer #1	CCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O[Si](C)(C)C	3113.6	Semi standard non polar	33892256
LysoPC(14:0/0:0),1TBDMS,isomer #1	CCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C	3337.9	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(14:0/0:0) GC-MS (1 TMS) - 70eV, Positive	splash10-0230-9411000000-7a6b8e8fd1e0609b417e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - LysoPC(14:0/0:0) GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - LysoPC(14:0/0:0) 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(14:0/0:0) 10V, Positive-QTOF	splash10-0006-0000900000-c557e23aa67a6a68e471	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(14:0/0:0) 20V, Positive-QTOF	splash10-001l-0000900000-89cc0e21e01554e310d6	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(14:0/0:0) 40V, Positive-QTOF	splash10-0pcr-1617900000-231c7760e10f0c81e04b	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(14:0/0:0) 10V, Negative-QTOF	splash10-0udi-0000390000-b1814b140293d64c3417	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(14:0/0:0) 20V, Negative-QTOF	splash10-0fb9-0090160000-48fcbf8694eed693a211	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(14:0/0:0) 40V, Negative-QTOF	splash10-004i-0090110000-c40c1368f5389cd115f2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(14:0/0:0) 10V, Positive-QTOF	splash10-0gb9-0000900000-534f405ea851fa87d3e5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(14:0/0:0) 20V, Positive-QTOF	splash10-00lr-0900600000-9a2a86225de12cddb6bd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(14:0/0:0) 40V, Positive-QTOF	splash10-0ue9-0910400000-63d03888aa82a44da515	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(14:0/0:0) 10V, Negative-QTOF	splash10-014i-0030900000-648928c7aa526a1c5514	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(14:0/0:0) 20V, Negative-QTOF	splash10-004i-0090100000-6eecefd72f10fda6c57a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(14:0/0:0) 40V, Negative-QTOF	splash10-004i-0090000000-aaa1334bcdf77ff34dd1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(14:0/0:0) 10V, Positive-QTOF	splash10-00di-0000900000-56c0d0685c46c9ba6fe3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(14:0/0:0) 20V, Positive-QTOF	splash10-01i0-0010900000-50babd7089582cb56ec8	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(14:0/0:0) 40V, Positive-QTOF	splash10-0frl-0390400000-26a01ba41c58e985ad7c	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

All Tissues

Pathways

Name	SMPDB/PathBank	KEGG
Arachidonic Acid Metabolism
Leukotriene C4 Synthesis Deficiency		Not Available
Piroxicam Action Pathway		Not Available
Acetylsalicylic Acid Action Pathway		Not Available
Etodolac Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	2.02 (0.99-2.63) uM	Adolescent (13-18 years old)	Both	Normal	28959601	details
Blood	Detected and Quantified	2.64 +/- 0.31 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	4.23 +/- 1.67 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	2.0-9.0 uM	Adult (>18 years old)	Both	Normal	Molecular You	details
Blood	Detected and Quantified	4.234 +/- 1.669 uM	Adult (>18 years old)	Both	Normal	18953024	details
Blood	Detected and Quantified	2.22 (2.05-2.45) uM	Newborn (0-30 days old)	Not Available	Normal	25754623	details
Blood	Detected and Quantified	2.11 (1.79-2.51) uM	Infant (0-1 year old)	Not Available	Normal	25754623	details
Feces	Detected and Quantified	6.73 +/- 3.85 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected and Quantified	6.73 +/- 3.47 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Saliva	Detected and Quantified	5.344 +/- 0.261 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Urine	Detected and Quantified	0.0-0.01 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	32340350	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Ovarian cancer	22309680	details
Blood	Detected and Quantified	1.97 (1.54-3.82) uM	Adolescent (13-18 years old)	Both	Pain or fever	28959601	details
Blood	Detected and Quantified	3.41 (2.50-4.75) uM	Adolescent (13-18 years old)	Both	Acetaminophen overdose	28959601	details

Associated Disorders and Diseases

Disease References

Ovarian cancer
Zhang T, Wu X, Yin M, Fan L, Zhang H, Zhao F, Zhang W, Ke C, Zhang G, Hou Y, Zhou X, Lou G, Li K: Discrimination between malignant and benign ovarian tumors by plasma metabolomic profiling using ultra performance liquid chromatography/mass spectrometry. Clin Chim Acta. 2012 May 18;413(9-10):861-8. doi: 10.1016/j.cca.2012.01.026. Epub 2012 Jan 30. [PubMed:22309680 ]

Associated OMIM IDs

167000 (Ovarian cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB027530

KNApSAcK ID

Not Available

Chemspider ID

405289

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

460604

PDB ID

Not Available

ChEBI ID

64489

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(14:0/0:0) (HMDB0010379)

MOL for HMDB0010379 (LysoPC(14:0/0:0))

3D MOL for HMDB0010379 (LysoPC(14:0/0:0))

3D SDF for HMDB0010379 (LysoPC(14:0/0:0))

3D-SDF for HMDB0010379 (LysoPC(14:0/0:0))

PDB for HMDB0010379 (LysoPC(14:0/0:0))

3D PDB for HMDB0010379 (LysoPC(14:0/0:0))

SMILES for HMDB0010379 (LysoPC(14:0/0:0))

INCHI for HMDB0010379 (LysoPC(14:0/0:0))

Structure for HMDB0010379 (LysoPC(14:0/0:0))

3D Structure for HMDB0010379 (LysoPC(14:0/0:0))

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes