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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (15) Show 15 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2009-03-25 15:15:54 UTC

Update Date

2022-08-16 22:05:49 UTC

HMDB ID

HMDB0012108

Secondary Accession Numbers

HMDB12108

Metabolite Identification

Common Name

LysoPC(17:0/0:0)

Description

LysoPC(17:0) 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(17:0), in particular, consists of one chain of margaric acid at the C-1 position. The margaric acid moiety is derived from butter, milk and fat of ruminants. 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 (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(17:0/0:0)
  Mrv1652311211916412D          

 34 33  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
    9.0919   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3778   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6637   -6.1163    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
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  CHG  2   6   1  11  -1
M  END

HMDB0012108
     RDKit          3D
LysoPC(17:0/0:0)
 86 85  0  0  0  0  0  0  0  0999 V2000
   12.4424    1.1333   -0.7768 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8407   -0.0481   -1.4723 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2095   -1.0305   -0.5295 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1020   -0.4495    0.2878 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9684    0.0838   -0.5684 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9070    0.6465    0.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7734    1.1782   -0.4629 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6644    1.7602    0.3678 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0498    0.7765    1.3067 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4490   -0.4114    0.6114 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3651   -0.0605   -0.3469 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1972    0.6403    0.2570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4922   -0.1508    1.3421 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9673   -1.4744    0.7762 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2945   -2.2220    1.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8476   -1.4494    2.4558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9154   -1.2158    1.4245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8138   -1.7380    0.3008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9993   -0.4315    1.7160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0543   -0.1183    0.8765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7422    0.6786   -0.3396 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8586    0.0095   -1.1577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9877    0.9609   -1.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9452    1.6385   -0.4075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3310    1.9625   -1.2767 P   0  0  0  0  0  5  0  0  0  0  0  0
   -7.6046    3.4277   -1.4699 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3208    1.2384   -2.8045 O   0  0  0  0  0  1  0  0  0  0  0  0
   -8.6516    1.3018   -0.4359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6207   -0.0809   -0.5968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7309   -0.7963    0.0948 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0356   -0.4177   -0.3406 N   0  0  0  0  0  4  0  0  0  0  0  0
  -11.6539    0.4602    0.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0145    0.1487   -1.6665 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8740   -1.6263   -0.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1855    2.0437   -1.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5581    1.0662   -0.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0830    1.2946    0.2473 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6651   -0.5872   -2.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1343    0.2696   -2.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9861   -1.4006    0.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7833   -1.8518   -1.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6986   -1.2646    0.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4451    0.3383    0.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5510   -0.7469   -1.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2916    0.8660   -1.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6029   -0.1694    1.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3220    1.4637    0.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1930    2.0012   -1.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3730    0.4138   -1.1543 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8836    2.1167   -0.3349 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0029    2.6324    0.9651 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1919    1.3096    1.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7481    0.5172    2.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1023   -1.1916    1.2859 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2815   -0.8700    0.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0295   -0.9937   -0.8454 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7685    0.6223   -1.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358    0.7717   -0.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4674    1.6469    0.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6655    0.5039    1.6864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1185   -0.3925    2.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8669   -2.0620    0.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3248   -1.3143   -0.0774 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0188   -2.4577    2.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0703   -3.2080    1.4704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2946   -2.0925    3.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303   -0.4932    2.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8338    0.3782    1.5214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5393   -1.1003    0.6006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2297    1.6489   -0.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4325    0.5642   -1.8453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6913    1.4723   -2.0734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4258   -0.0196   -1.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6171   -0.4106   -0.2601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6335   -0.2585   -1.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5803   -1.8798   -0.0420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6141   -0.6009    1.1950 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0248    1.3110    0.9218 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9430   -0.1929    1.4937 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5876    0.8533    0.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5370   -0.5713   -2.3579 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6037    1.1635   -1.7080 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0778    0.2316   -2.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6507   -2.2186   -1.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9304   -1.2907   -0.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6521   -2.1860    0.5457 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 25 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  1  0
 31 34  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  0
  2 39  1  0
  3 40  1  0
  3 41  1  0
  4 42  1  0
  4 43  1  0
  5 44  1  0
  5 45  1  0
  6 46  1  0
  6 47  1  0
  7 48  1  0
  7 49  1  0
  8 50  1  0
  8 51  1  0
  9 52  1  0
  9 53  1  0
 10 54  1  0
 10 55  1  0
 11 56  1  0
 11 57  1  0
 12 58  1  0
 12 59  1  0
 13 60  1  0
 13 61  1  0
 14 62  1  0
 14 63  1  0
 15 64  1  0
 15 65  1  0
 16 66  1  0
 16 67  1  0
 20 68  1  0
 20 69  1  0
 21 70  1  1
 22 71  1  0
 23 72  1  0
 23 73  1  0
 29 74  1  0
 29 75  1  0
 30 76  1  0
 30 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
 34 84  1  0
 34 85  1  0
 34 86  1  0
M  CHG  2  27  -1  31   1
M  END

LysoPC(17:0/0:0)
  Mrv1652311211916412D          

 34 33  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
    9.0919   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3778   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6637   -6.1163    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
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  CHG  2   6   1  11  -1
M  END
> <DATABASE_ID>
HMDB0012108

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C25H52NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-25(28)31-22-24(27)23-33-34(29,30)32-21-20-26(2,3)4/h24,27H,5-23H2,1-4H3/t24-/m1/s1

> <INCHI_KEY>
SRRQPVVYXBTRQK-XMMPIXPASA-N

> <FORMULA>
C25H52NO7P

> <MOLECULAR_WEIGHT>
509.6566

> <EXACT_MASS>
509.348139535

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
86

> <JCHEM_AVERAGE_POLARIZABILITY>
60.01913178181053

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
2.18

> <JCHEM_LOGP>
1.6373111418615869

> <ALOGPS_LOGS>
-6.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.655609236411614

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8553406136270887

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4040033707844772

> <JCHEM_POLAR_SURFACE_AREA>
105.11999999999999

> <JCHEM_REFRACTIVITY>
146.87470000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
25

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.89e-04 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012108
     RDKit          3D
LysoPC(17:0/0:0)
 86 85  0  0  0  0  0  0  0  0999 V2000
   12.4424    1.1333   -0.7768 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8407   -0.0481   -1.4723 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2095   -1.0305   -0.5295 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1020   -0.4495    0.2878 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9684    0.0838   -0.5684 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9070    0.6465    0.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7734    1.1782   -0.4629 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6644    1.7602    0.3678 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0498    0.7765    1.3067 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4490   -0.4114    0.6114 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3651   -0.0605   -0.3469 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1972    0.6403    0.2570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4922   -0.1508    1.3421 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9673   -1.4744    0.7762 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2945   -2.2220    1.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8476   -1.4494    2.4558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9154   -1.2158    1.4245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8138   -1.7380    0.3008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9993   -0.4315    1.7160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0543   -0.1183    0.8765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7422    0.6786   -0.3396 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8586    0.0095   -1.1577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9877    0.9609   -1.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9452    1.6385   -0.4075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3310    1.9625   -1.2767 P   0  0  0  0  0  5  0  0  0  0  0  0
   -7.6046    3.4277   -1.4699 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3208    1.2384   -2.8045 O   0  0  0  0  0  1  0  0  0  0  0  0
   -8.6516    1.3018   -0.4359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6207   -0.0809   -0.5968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7309   -0.7963    0.0948 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0356   -0.4177   -0.3406 N   0  0  0  0  0  4  0  0  0  0  0  0
  -11.6539    0.4602    0.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0145    0.1487   -1.6665 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8740   -1.6263   -0.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1855    2.0437   -1.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5581    1.0662   -0.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0830    1.2946    0.2473 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6651   -0.5872   -2.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1343    0.2696   -2.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9861   -1.4006    0.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7833   -1.8518   -1.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6986   -1.2646    0.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4451    0.3383    0.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5510   -0.7469   -1.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2916    0.8660   -1.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6029   -0.1694    1.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3220    1.4637    0.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1930    2.0012   -1.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3730    0.4138   -1.1543 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8836    2.1167   -0.3349 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0029    2.6324    0.9651 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1919    1.3096    1.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7481    0.5172    2.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1023   -1.1916    1.2859 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2815   -0.8700    0.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0295   -0.9937   -0.8454 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7685    0.6223   -1.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358    0.7717   -0.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4674    1.6469    0.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6655    0.5039    1.6864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1185   -0.3925    2.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8669   -2.0620    0.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3248   -1.3143   -0.0774 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0188   -2.4577    2.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0703   -3.2080    1.4704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2946   -2.0925    3.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303   -0.4932    2.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8338    0.3782    1.5214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5393   -1.1003    0.6006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2297    1.6489   -0.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4325    0.5642   -1.8453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6913    1.4723   -2.0734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4258   -0.0196   -1.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6171   -0.4106   -0.2601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6335   -0.2585   -1.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5803   -1.8798   -0.0420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6141   -0.6009    1.1950 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0248    1.3110    0.9218 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9430   -0.1929    1.4937 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5876    0.8533    0.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5370   -0.5713   -2.3579 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6037    1.1635   -1.7080 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0778    0.2316   -2.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6507   -2.2186   -1.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9304   -1.2907   -0.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6521   -2.1860    0.5457 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 25 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  1  0
 31 34  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  0
  2 39  1  0
  3 40  1  0
  3 41  1  0
  4 42  1  0
  4 43  1  0
  5 44  1  0
  5 45  1  0
  6 46  1  0
  6 47  1  0
  7 48  1  0
  7 49  1  0
  8 50  1  0
  8 51  1  0
  9 52  1  0
  9 53  1  0
 10 54  1  0
 10 55  1  0
 11 56  1  0
 11 57  1  0
 12 58  1  0
 12 59  1  0
 13 60  1  0
 13 61  1  0
 14 62  1  0
 14 63  1  0
 15 64  1  0
 15 65  1  0
 16 66  1  0
 16 67  1  0
 20 68  1  0
 20 69  1  0
 21 70  1  1
 22 71  1  0
 23 72  1  0
 23 73  1  0
 29 74  1  0
 29 75  1  0
 30 76  1  0
 30 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
 34 84  1  0
 34 85  1  0
 34 86  1  0
M  CHG  2  27  -1  31   1
M  END

HEADER    PROTEIN                                 21-NOV-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: LysoPC(17:0/0:0)                                  
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
HETATM   32  C   UNK     0      16.972 -11.417   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      15.639 -12.188   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      14.306 -11.417   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   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   66    0
END

COMPND    HMDB0012108
HETATM    1  C1  UNL     1      12.442   1.133  -0.777  1.00  0.00           C  
HETATM    2  C2  UNL     1      11.841  -0.048  -1.472  1.00  0.00           C  
HETATM    3  C3  UNL     1      11.209  -1.030  -0.530  1.00  0.00           C  
HETATM    4  C4  UNL     1      10.102  -0.449   0.288  1.00  0.00           C  
HETATM    5  C5  UNL     1       8.968   0.084  -0.568  1.00  0.00           C  
HETATM    6  C6  UNL     1       7.907   0.647   0.382  1.00  0.00           C  
HETATM    7  C7  UNL     1       6.773   1.178  -0.463  1.00  0.00           C  
HETATM    8  C8  UNL     1       5.664   1.760   0.368  1.00  0.00           C  
HETATM    9  C9  UNL     1       5.050   0.776   1.307  1.00  0.00           C  
HETATM   10  C10 UNL     1       4.449  -0.411   0.611  1.00  0.00           C  
HETATM   11  C11 UNL     1       3.365  -0.061  -0.347  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.197   0.640   0.257  1.00  0.00           C  
HETATM   13  C13 UNL     1       1.492  -0.151   1.342  1.00  0.00           C  
HETATM   14  C14 UNL     1       0.967  -1.474   0.776  1.00  0.00           C  
HETATM   15  C15 UNL     1       0.294  -2.222   1.888  1.00  0.00           C  
HETATM   16  C16 UNL     1      -0.848  -1.449   2.456  1.00  0.00           C  
HETATM   17  C17 UNL     1      -1.915  -1.216   1.424  1.00  0.00           C  
HETATM   18  O1  UNL     1      -1.814  -1.738   0.301  1.00  0.00           O  
HETATM   19  O2  UNL     1      -2.999  -0.432   1.716  1.00  0.00           O  
HETATM   20  C18 UNL     1      -4.054  -0.118   0.877  1.00  0.00           C  
HETATM   21  C19 UNL     1      -3.742   0.679  -0.340  1.00  0.00           C  
HETATM   22  O3  UNL     1      -2.859   0.010  -1.158  1.00  0.00           O  
HETATM   23  C20 UNL     1      -4.988   0.961  -1.158  1.00  0.00           C  
HETATM   24  O4  UNL     1      -5.945   1.639  -0.408  1.00  0.00           O  
HETATM   25  P1  UNL     1      -7.331   1.962  -1.277  1.00  0.00           P  
HETATM   26  O5  UNL     1      -7.605   3.428  -1.470  1.00  0.00           O  
HETATM   27  O6  UNL     1      -7.321   1.238  -2.804  1.00  0.00           O1-
HETATM   28  O7  UNL     1      -8.652   1.302  -0.436  1.00  0.00           O  
HETATM   29  C21 UNL     1      -8.621  -0.081  -0.597  1.00  0.00           C  
HETATM   30  C22 UNL     1      -9.731  -0.796   0.095  1.00  0.00           C  
HETATM   31  N1  UNL     1     -11.036  -0.418  -0.341  1.00  0.00           N1+
HETATM   32  C23 UNL     1     -11.654   0.460   0.625  1.00  0.00           C  
HETATM   33  C24 UNL     1     -11.014   0.149  -1.666  1.00  0.00           C  
HETATM   34  C25 UNL     1     -11.874  -1.626  -0.380  1.00  0.00           C  
HETATM   35  H1  UNL     1      12.185   2.044  -1.363  1.00  0.00           H  
HETATM   36  H2  UNL     1      13.558   1.066  -0.749  1.00  0.00           H  
HETATM   37  H3  UNL     1      12.083   1.295   0.247  1.00  0.00           H  
HETATM   38  H4  UNL     1      12.665  -0.587  -2.001  1.00  0.00           H  
HETATM   39  H5  UNL     1      11.134   0.270  -2.289  1.00  0.00           H  
HETATM   40  H6  UNL     1      11.986  -1.401   0.149  1.00  0.00           H  
HETATM   41  H7  UNL     1      10.783  -1.852  -1.141  1.00  0.00           H  
HETATM   42  H8  UNL     1       9.699  -1.265   0.929  1.00  0.00           H  
HETATM   43  H9  UNL     1      10.445   0.338   0.993  1.00  0.00           H  
HETATM   44  H10 UNL     1       8.551  -0.747  -1.172  1.00  0.00           H  
HETATM   45  H11 UNL     1       9.292   0.866  -1.257  1.00  0.00           H  
HETATM   46  H12 UNL     1       7.603  -0.169   1.044  1.00  0.00           H  
HETATM   47  H13 UNL     1       8.322   1.464   0.978  1.00  0.00           H  
HETATM   48  H14 UNL     1       7.193   2.001  -1.082  1.00  0.00           H  
HETATM   49  H15 UNL     1       6.373   0.414  -1.154  1.00  0.00           H  
HETATM   50  H16 UNL     1       4.884   2.117  -0.335  1.00  0.00           H  
HETATM   51  H17 UNL     1       6.003   2.632   0.965  1.00  0.00           H  
HETATM   52  H18 UNL     1       4.192   1.310   1.811  1.00  0.00           H  
HETATM   53  H19 UNL     1       5.748   0.517   2.101  1.00  0.00           H  
HETATM   54  H20 UNL     1       4.102  -1.192   1.286  1.00  0.00           H  
HETATM   55  H21 UNL     1       5.282  -0.870   0.004  1.00  0.00           H  
HETATM   56  H22 UNL     1       3.029  -0.994  -0.845  1.00  0.00           H  
HETATM   57  H23 UNL     1       3.769   0.622  -1.152  1.00  0.00           H  
HETATM   58  H24 UNL     1       1.436   0.772  -0.559  1.00  0.00           H  
HETATM   59  H25 UNL     1       2.467   1.647   0.582  1.00  0.00           H  
HETATM   60  H26 UNL     1       0.665   0.504   1.686  1.00  0.00           H  
HETATM   61  H27 UNL     1       2.118  -0.393   2.198  1.00  0.00           H  
HETATM   62  H28 UNL     1       1.867  -2.062   0.427  1.00  0.00           H  
HETATM   63  H29 UNL     1       0.325  -1.314  -0.077  1.00  0.00           H  
HETATM   64  H30 UNL     1       1.019  -2.458   2.714  1.00  0.00           H  
HETATM   65  H31 UNL     1      -0.070  -3.208   1.470  1.00  0.00           H  
HETATM   66  H32 UNL     1      -1.295  -2.092   3.265  1.00  0.00           H  
HETATM   67  H33 UNL     1      -0.530  -0.493   2.909  1.00  0.00           H  
HETATM   68  H34 UNL     1      -4.834   0.378   1.521  1.00  0.00           H  
HETATM   69  H35 UNL     1      -4.539  -1.100   0.601  1.00  0.00           H  
HETATM   70  H36 UNL     1      -3.230   1.649  -0.073  1.00  0.00           H  
HETATM   71  H37 UNL     1      -2.433   0.564  -1.845  1.00  0.00           H  
HETATM   72  H38 UNL     1      -4.691   1.472  -2.073  1.00  0.00           H  
HETATM   73  H39 UNL     1      -5.426  -0.020  -1.435  1.00  0.00           H  
HETATM   74  H40 UNL     1      -7.617  -0.411  -0.260  1.00  0.00           H  
HETATM   75  H41 UNL     1      -8.634  -0.258  -1.704  1.00  0.00           H  
HETATM   76  H42 UNL     1      -9.580  -1.880  -0.042  1.00  0.00           H  
HETATM   77  H43 UNL     1      -9.614  -0.601   1.195  1.00  0.00           H  
HETATM   78  H44 UNL     1     -11.025   1.311   0.922  1.00  0.00           H  
HETATM   79  H45 UNL     1     -11.943  -0.193   1.494  1.00  0.00           H  
HETATM   80  H46 UNL     1     -12.588   0.853   0.168  1.00  0.00           H  
HETATM   81  H47 UNL     1     -10.537  -0.571  -2.358  1.00  0.00           H  
HETATM   82  H48 UNL     1     -10.604   1.163  -1.708  1.00  0.00           H  
HETATM   83  H49 UNL     1     -12.078   0.232  -2.033  1.00  0.00           H  
HETATM   84  H50 UNL     1     -11.651  -2.219  -1.283  1.00  0.00           H  
HETATM   85  H51 UNL     1     -12.930  -1.291  -0.332  1.00  0.00           H  
HETATM   86  H52 UNL     1     -11.652  -2.186   0.546  1.00  0.00           H  
CONECT    1    2   35   36   37
CONECT    2    3   38   39
CONECT    3    4   40   41
CONECT    4    5   42   43
CONECT    5    6   44   45
CONECT    6    7   46   47
CONECT    7    8   48   49
CONECT    8    9   50   51
CONECT    9   10   52   53
CONECT   10   11   54   55
CONECT   11   12   56   57
CONECT   12   13   58   59
CONECT   13   14   60   61
CONECT   14   15   62   63
CONECT   15   16   64   65
CONECT   16   17   66   67
CONECT   17   18   18   19
CONECT   19   20
CONECT   20   21   68   69
CONECT   21   22   23   70
CONECT   22   71
CONECT   23   24   72   73
CONECT   24   25
CONECT   25   26   26   27   28
CONECT   28   29
CONECT   29   30   74   75
CONECT   30   31   76   77
CONECT   31   32   33   34
CONECT   32   78   79   80
CONECT   33   81   82   83
CONECT   34   84   85   86
END

HMDB0012108
     RDKit          3D
LysoPC(17:0/0:0)
 86 85  0  0  0  0  0  0  0  0999 V2000
   12.4424    1.1333   -0.7768 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8407   -0.0481   -1.4723 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2095   -1.0305   -0.5295 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1020   -0.4495    0.2878 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9684    0.0838   -0.5684 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9070    0.6465    0.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7734    1.1782   -0.4629 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6644    1.7602    0.3678 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0498    0.7765    1.3067 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4490   -0.4114    0.6114 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3651   -0.0605   -0.3469 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1972    0.6403    0.2570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4922   -0.1508    1.3421 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9673   -1.4744    0.7762 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2945   -2.2220    1.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8476   -1.4494    2.4558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9154   -1.2158    1.4245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8138   -1.7380    0.3008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9993   -0.4315    1.7160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0543   -0.1183    0.8765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7422    0.6786   -0.3396 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8586    0.0095   -1.1577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9877    0.9609   -1.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9452    1.6385   -0.4075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3310    1.9625   -1.2767 P   0  0  0  0  0  5  0  0  0  0  0  0
   -7.6046    3.4277   -1.4699 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3208    1.2384   -2.8045 O   0  0  0  0  0  1  0  0  0  0  0  0
   -8.6516    1.3018   -0.4359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6207   -0.0809   -0.5968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7309   -0.7963    0.0948 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0356   -0.4177   -0.3406 N   0  0  0  0  0  4  0  0  0  0  0  0
  -11.6539    0.4602    0.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0145    0.1487   -1.6665 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8740   -1.6263   -0.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1855    2.0437   -1.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5581    1.0662   -0.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0830    1.2946    0.2473 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6651   -0.5872   -2.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1343    0.2696   -2.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9861   -1.4006    0.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7833   -1.8518   -1.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6986   -1.2646    0.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4451    0.3383    0.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5510   -0.7469   -1.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2916    0.8660   -1.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6029   -0.1694    1.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3220    1.4637    0.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1930    2.0012   -1.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3730    0.4138   -1.1543 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8836    2.1167   -0.3349 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0029    2.6324    0.9651 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1919    1.3096    1.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7481    0.5172    2.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1023   -1.1916    1.2859 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2815   -0.8700    0.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0295   -0.9937   -0.8454 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7685    0.6223   -1.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358    0.7717   -0.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4674    1.6469    0.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6655    0.5039    1.6864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1185   -0.3925    2.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8669   -2.0620    0.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3248   -1.3143   -0.0774 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0188   -2.4577    2.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0703   -3.2080    1.4704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2946   -2.0925    3.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303   -0.4932    2.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8338    0.3782    1.5214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5393   -1.1003    0.6006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2297    1.6489   -0.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4325    0.5642   -1.8453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6913    1.4723   -2.0734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4258   -0.0196   -1.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6171   -0.4106   -0.2601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6335   -0.2585   -1.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5803   -1.8798   -0.0420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6141   -0.6009    1.1950 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0248    1.3110    0.9218 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9430   -0.1929    1.4937 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5876    0.8533    0.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5370   -0.5713   -2.3579 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6037    1.1635   -1.7080 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0778    0.2316   -2.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6507   -2.2186   -1.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9304   -1.2907   -0.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6521   -2.1860    0.5457 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 25 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  1  0
 31 34  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  0
  2 39  1  0
  3 40  1  0
  3 41  1  0
  4 42  1  0
  4 43  1  0
  5 44  1  0
  5 45  1  0
  6 46  1  0
  6 47  1  0
  7 48  1  0
  7 49  1  0
  8 50  1  0
  8 51  1  0
  9 52  1  0
  9 53  1  0
 10 54  1  0
 10 55  1  0
 11 56  1  0
 11 57  1  0
 12 58  1  0
 12 59  1  0
 13 60  1  0
 13 61  1  0
 14 62  1  0
 14 63  1  0
 15 64  1  0
 15 65  1  0
 16 66  1  0
 16 67  1  0
 20 68  1  0
 20 69  1  0
 21 70  1  1
 22 71  1  0
 23 72  1  0
 23 73  1  0
 29 74  1  0
 29 75  1  0
 30 76  1  0
 30 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
 34 84  1  0
 34 85  1  0
 34 86  1  0
M  CHG  2  27  -1  31   1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Heptadecanoyl-glycero-3-phosphocholine	ChEBI
1-Margaroyl-GPC	ChEBI
1-Margaroyl-GPC (17:0)	ChEBI
GPC(17:0)	ChEBI
LPC (17:0/0:0)	ChEBI
LPC 17:0/0:0	ChEBI
LPC(17:0/0:0)	ChEBI
LysoPC 17:0/0:0	ChEBI
Lysophosphatidylcholine(17:0)	ChEBI
Lysophosphatidylcholine(17:0/0:0)	ChEBI
PC 17:0/0:0	ChEBI
PC(17:0/0:0)	ChEBI
LPC(17:0)	HMDB
LyPC(17:0)	HMDB
LyPC(17:0/0:0)	HMDB
LysoPC a C17:0	HMDB
1-Margaroyl-glycero-3-phosphocholine	HMDB
LysoPC(17:0)	HMDB
1-Heptadecanoyl-2-hydroxy-sn-glycero-3-phosphocholine	HMDB
1-Heptadecanoylglycerophosphocholine	HMDB
Lysophosphatidylcholine (C17:0)	HMDB
1-Margaroylglycerophosphocholine	HMDB
1-Margaroyl-lysophosphatidylcholine	HMDB
1-Margaroyl-sn-glycero-3-phosphocholine	HMDB
GPC(17:0/0:0)	HMDB
LysoPC(17:0/0:0)	Lipid Annotator, ChEBI

Chemical Formula

C₂₅H₅₂NO₇P

Average Molecular Weight

509.6566

Monoisotopic Molecular Weight

509.348139535

IUPAC Name

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

Traditional Name

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

CAS Registry Number

50930-23-9

SMILES

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

InChI Identifier

InChI=1S/C25H52NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-25(28)31-22-24(27)23-33-34(29,30)32-21-20-26(2,3)4/h24,27H,5-23H2,1-4H3/t24-/m1/s1

InChI Key

SRRQPVVYXBTRQK-XMMPIXPASA-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

lysophosphatidylcholine 17:0 (CHEBI:74340 )
Monoacylglycerophosphocholines (LMGP01050024 )

Ontology

Physiological effect

Health effect

Cancer

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

Nervous system disorder

Central nervous system disorder

Alzheimer's Disease (PMID: 30845751)

Digestive system disorder

Gastrointestinal disorder

Stomach cancer (PMID: 26162894)

Renal system and urinary system

Renal disorder

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

Organoleptic effect

Touch

Smooth (HMDB: HMDB0012108)

Disposition

Biological location

Cell membrane (HMDB: HMDB0012108)
Intracellular membrane (HMDB: HMDB0012108)

Biofluid or Excreta

Non-excretory biofluid

Blood (PMID: 21359215)

Excreta

Urine (PMID: 24023812)
Feces (PMID: 27624970)

Cellular substructure

Cell

All cells and tissues (HMDB: HMDB0012108)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012108)

Source

Endogenous

Endogenous (HMDB: HMDB0012108)

Animal

Animal (HMDB: HMDB0012108)

Exogenous

Food

Food (HMDB: HMDB0012108)

Animal origin

Poultry

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Swine

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

Caprae

Domestic goat (FooDB: FOOD00529)

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Cow milk, pasteurized, vitamin A + D added, 0% fat (FooDB: FOOD00889)
Cow milk, pasteurized, vitamin D added, 3.25% fat (FooDB: FOOD00892)
Cow milk, pasteurized, vitamin A + D added, 1% fat (FooDB: FOOD00890)
Cow milk, pasteurized, vitamin A + D added, 2% fat (FooDB: FOOD00891)

Process

Naturally occurring process

Biological process

Cellular process

Apoptosis (PMID: 30845751)
Cell signaling (HMDB: HMDB0012108)

Biochemical pathway

Signaling pathway

Apoptosis (PMID: 30845751)

Glycerophospholipid metabolism (HMDB: HMDB0012108)

Chemical reaction

Lipid peroxidation (HMDB: HMDB0012108)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0012108)

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

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00029 g/L	ALOGPS
logP	2.18	ALOGPS
logP	1.64	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	105.12 Å²	ChemAxon
Rotatable Bond Count	25	ChemAxon
Refractivity	146.87 m³·mol⁻¹	ChemAxon
Polarizability	60.02 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	236.071	30932474
DeepCCS	[M-H]-	233.713	30932474
DeepCCS	[M-2H]-	266.947	30932474
DeepCCS	[M+Na]+	243.455	30932474
AllCCS	[M+H]+	236.8	32859911
AllCCS	[M+H-H2O]+	235.5	32859911
AllCCS	[M+NH4]+	238.0	32859911
AllCCS	[M+Na]+	238.3	32859911
AllCCS	[M-H]-	231.3	32859911
AllCCS	[M+Na-2H]-	233.8	32859911
AllCCS	[M+HCOO]-	236.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
LysoPC(17:0/0:0)	CCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C	3518.2	Standard polar	33892256
LysoPC(17:0/0:0)	CCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C	3134.0	Standard non polar	33892256
LysoPC(17:0/0:0)	CCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C	3434.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
LysoPC(17:0/0:0),1TMS,isomer #1	CCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O[Si](C)(C)C	3405.3	Semi standard non polar	33892256
LysoPC(17:0/0:0),1TBDMS,isomer #1	CCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C	3639.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - LysoPC(17:0/0:0) GC-MS (1 TMS) - 70eV, Positive	splash10-00g0-9311000000-93a0b5b9e5f537c618dd	2017-10-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - LysoPC(17:0/0:0) 40V, Positive-QTOF	splash10-0f89-1900000000-5f02fa0f1176a59f106e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - LysoPC(17:0/0:0) 10V, Positive-QTOF	splash10-03di-0000090000-94d9e2275cda76286a6c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - LysoPC(17:0/0:0) 20V, Positive-QTOF	splash10-03di-0200090000-34355ed9a9a5b146b7cc	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(17:0/0:0) 10V, Negative-QTOF	splash10-0006-0000190000-d912ebcc582e7e7ebf68	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(17:0/0:0) 20V, Negative-QTOF	splash10-014l-0090070000-1ba0f9762e33fbcce22b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(17:0/0:0) 40V, Negative-QTOF	splash10-014i-0090020000-08553871ff6c127650b2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(17:0/0:0) 10V, Positive-QTOF	splash10-001i-0000190000-fd17df396eea86beaebc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(17:0/0:0) 20V, Positive-QTOF	splash10-00e9-0001960000-25105e7a20be144cd00d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(17:0/0:0) 40V, Positive-QTOF	splash10-0fdk-1609710000-6761294dff05eef577b8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(17:0/0:0) 10V, Negative-QTOF	splash10-0a4i-0030090000-b1470a5e8c1f72620b13	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(17:0/0:0) 20V, Negative-QTOF	splash10-014i-0090010000-9b7a3651bf4a9dca6929	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(17:0/0:0) 40V, Negative-QTOF	splash10-014i-0090000000-f25c5da4f67ced9e0d09	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(17:0/0:0) 10V, Positive-QTOF	splash10-03dl-0100690000-8067aca90102c943040e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(17:0/0:0) 20V, Positive-QTOF	splash10-01q9-0900150000-710bcf758d5d5c216653	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(17:0/0:0) 40V, Positive-QTOF	splash10-0f8c-0910300000-fb1151d78a4fed481d67	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(17:0/0:0) 10V, Positive-QTOF	splash10-014i-0000190000-4a106fa491faee412eb8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(17:0/0:0) 20V, Positive-QTOF	splash10-0b90-0002990000-99899b56168cb2071f72	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(17:0/0:0) 40V, Positive-QTOF	splash10-0ke9-0309400000-2332b4fc27fe465cb173	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	2.55 +/- 1.08 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	0.90-2.60 uM	Adult (>18 years old)	Both	Normal	The Metabolo...	details
Blood	Detected and Quantified	0.74 (0.6-0.94) uM	Newborn (0-30 days old)	Not Available	Normal	25754623	details
Blood	Detected and Quantified	1.64 +/- 0.40 uM	Adult (>18 years old)	Both	Normal	28278231	details
Blood	Detected and Quantified	1.11 (0.83-1.58) uM	Infant (0-1 year old)	Not Available	Normal	25754623	details
Feces	Detected and Quantified	0.38 +/- 0.24 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected and Quantified	0.5 +/- 0.34 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Urine	Detected and Quantified	0.0032 (0.0008-0.0087) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	0.0084 +/- 0.0111 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	0.0-0.06 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	32340350	details
Urine	Detected and Quantified	0.01(0.0-0.03) umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	32340350	details
Urine	Detected and Quantified	0.0(0.0-0.07) umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	32340350	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.24(0.1-0.8) uM	Adult (>18 years old)	Both	Sepsis	26847922	details
Blood	Detected and Quantified	1.8811 (1.9996) uM	Adult (>18 years old)	Female	Pregnancy with fetus having congenital heart defect	24704061	details
Blood	Detected and Quantified	2.6388 (0.8126) uM	Adult (>18 years old)	Female	Pregnancy	24704061	details
Urine	Detected and Quantified	0.0039 +/- 0.0026 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	0.0053 +/- 0.0103 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Analysis of 30 no...	details

Associated Disorders and Diseases

Disease References

Pregnancy
Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
Sepsis
Ferrario M, Cambiaghi A, Brunelli L, Giordano S, Caironi P, Guatteri L, Raimondi F, Gattinoni L, Latini R, Masson S, Ristagno G, Pastorelli R: Mortality prediction in patients with severe septic shock: a pilot study using a target metabolomics approach. Sci Rep. 2016 Feb 5;6:20391. doi: 10.1038/srep20391. [PubMed:26847922 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028772

KNApSAcK ID

Not Available

Chemspider ID

24694752

KEGG Compound ID

C04230

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24779463

PDB ID

Not Available

ChEBI ID

74340

Food Biomarker Ontology

Not Available

VMH ID

PCHOLHEP_HS

MarkerDB ID

MDB00000848

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Cai S, Huo T, Li N, Xiong Z, Li F: Lysophosphatidylcholine--biomarker of Metformin action: studied using UPLC/MS/MS. Biomed Chromatogr. 2009 Jul;23(7):782-6. doi: 10.1002/bmc.1185. [PubMed:19309761 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
Wernly B, Lichtenauer M, Hoppe UC, Jung C: Hyperglycemia in septic patients: an essential stress survival response in all, a robust marker for risk stratification in some, to be messed with in none. J Thorac Dis. 2016 Jul;8(7):E621-4. doi: 10.21037/jtd.2016.05.24. [PubMed:27501420 ]
Knuplez E, Marsche G: An Updated Review of Pro- and Anti-Inflammatory Properties of Plasma Lysophosphatidylcholines in the Vascular System. Int J Mol Sci. 2020 Jun 24;21(12). pii: ijms21124501. doi: 10.3390/ijms21124501. [PubMed:32599910 ]
Sun JK, Sun F, Wang X, Yuan ST, Zheng SY, Mu XW: Risk factors and prognosis of hypoalbuminemia in surgical septic patients. PeerJ. 2015 Oct 1;3:e1267. doi: 10.7717/peerj.1267. eCollection 2015. [PubMed:26557421 ]
Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Only showing the first 10 proteins. There are 15 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Cytosolic phospholipase A2

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

Enzyme Details

2. Eosinophil lysophospholipase

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

Enzyme Details

3. Platelet-activating factor acetylhydrolase

General function:: Involved in 1-alkyl-2-acetylglycerophosphocholine esterase activity
Specific function:: Modulates the action of platelet-activating factor (PAF) by hydrolyzing the sn-2 ester bond to yield the biologically inactive lyso-PAF. Has a specificity for substrates with a short residue at the sn-2 position. It is inactive against long-chain phospholipids.
Gene Name:: PLA2G7
Uniprot ID:: Q13093
Molecular weight:: 50076.99

Enzyme Details

4. Platelet-activating factor acetylhydrolase IB subunit gamma

General function:: Involved in hydrolase activity
Specific function:: Inactivates paf by removing the acetyl group at the sn-2 position. This is a catalytic subunit. Plays an important role during the development of brain.
Gene Name:: PAFAH1B3
Uniprot ID:: Q15102
Molecular weight:: 25734.13

Enzyme Details

5. Platelet-activating factor acetylhydrolase IB subunit beta

General function:: Involved in hydrolase activity
Specific function:: Inactivates PAF by removing the acetyl group at the sn-2 position. This is a catalytic subunit.
Gene Name:: PAFAH1B2
Uniprot ID:: P68402
Molecular weight:: 22733.715

Enzyme Details

6. Platelet-activating factor acetylhydrolase 2, cytoplasmic

General function:: Involved in 1-alkyl-2-acetylglycerophosphocholine esterase activity
Specific function:: Has a marked selectivity for phospholipids with short acyl chains at the sn-2 position. May share a common physiologic function with the plasma-type enzyme.
Gene Name:: PAFAH2
Uniprot ID:: Q99487
Molecular weight:: 44035.255

Enzyme Details

7. 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

8. Lysophospholipid acyltransferase 5

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

Enzyme Details

9. Lysophosphatidylcholine acyltransferase 1

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

Enzyme Details

10. Lysophosphatidylcholine acyltransferase 2

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

Only showing the first 10 proteins. There are 15 proteins in total.

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Showing metabocard for LysoPC(17:0/0:0) (HMDB0012108)

MOL for HMDB0012108 (LysoPC(17:0/0:0))

3D MOL for HMDB0012108 (LysoPC(17:0/0:0))

3D SDF for HMDB0012108 (LysoPC(17:0/0:0))

3D-SDF for HMDB0012108 (LysoPC(17:0/0:0))

PDB for HMDB0012108 (LysoPC(17:0/0:0))

3D PDB for HMDB0012108 (LysoPC(17:0/0:0))

SMILES for HMDB0012108 (LysoPC(17:0/0:0))

INCHI for HMDB0012108 (LysoPC(17:0/0:0))

Structure for HMDB0012108 (LysoPC(17:0/0:0))

3D Structure for HMDB0012108 (LysoPC(17:0/0:0))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes