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

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2008-09-16 13:20:08 UTC

Update Date

2022-07-14 16:57:35 UTC

HMDB ID

HMDB0010394

Secondary Accession Numbers

HMDB10394

Metabolite Identification

Common Name

LysoPC(20:3(8Z,11Z,14Z)/0:0)

Description

LysoPC(20:3(8Z,11Z,14Z)) 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(20:3(8Z,11Z,14Z)), in particular, consists of one chain of homo-g-linolenic acid at the C-1 position. The homo-g-linolenic acid moiety is derived from fish oils, liver and kidney. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2, as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling. In blood plasma significant amounts of lysophosphatidylcholine are formed by a specific enzyme system, lecithin:cholesterol acyltransferase (LCAT), which is secreted from the liver. The enzyme catalyzes the transfer of the fatty acids of position sn-2 of phosphatidylcholine to the free cholesterol in plasma, with formation of cholesterol esters and lysophosphatidylcholine. Lysophospholipids have a role in lipid signaling by acting on lysophospholipid receptors (LPL-R). LPL-R's are members of the G protein-coupled receptor family of integral membrane proteins. 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(20:3(8Z,11Z,14Z)/0:0)
  Mrv1652304202020502D          

 37 36  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
   13.2658   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5516   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8375   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0125   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2984   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5843   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7593   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0452   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3310   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6169   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9028   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1887   -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  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  CHG  2   6   1  11  -1
M  END

HMDB0010394
     RDKit          3D
LysoPC(20:3(8Z,11Z,14Z)/0:0)
 89 88  0  0  0  0  0  0  0  0999 V2000
  -11.5040   -1.0827    1.3393 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2579   -1.0013    2.8082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9415   -1.4111    3.3207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7446   -0.6492    2.8993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3941   -0.6270    1.4416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1475    0.1537    1.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0437    1.2473    0.5854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1117    1.8641   -0.1500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0546    1.9789   -1.6035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1485    1.5174   -2.3887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9300    0.7627   -2.1687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8006    1.5617   -2.7199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7502    1.8679   -2.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4369    1.5219   -0.6280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0788    0.7383   -0.5918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2057   -0.5011   -1.3937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1016   -1.4686   -1.4210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2098   -1.0221   -1.8736 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9286   -0.0781   -1.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2500    0.2232   -1.7084 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5262   -0.3111   -2.8124 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1745    1.0878   -1.1533 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3995    1.3754   -1.7827 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2927    0.1974   -1.9700 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4894    0.5215   -2.6051 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5649   -0.5070   -0.6430 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3057    0.3676    0.1178 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7251   -0.2251    1.6414 P   0  0  0  0  0  5  0  0  0  0  0  0
    6.7331    0.9334    2.6385 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6567   -1.3996    2.2011 O   0  0  0  0  0  1  0  0  0  0  0  0
    8.3137   -0.8469    1.6281 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9442   -0.4621    0.4448 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3390   -0.9706    0.3534 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2195   -0.5341    1.3908 N   0  0  0  0  0  4  0  0  0  0  0  0
   11.1323    0.8619    1.6916 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6094   -0.7800    0.9666 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9982   -1.3451    2.5678 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6054   -1.3709    1.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8910   -1.8197    0.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4103   -0.0762    0.8859 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0690   -1.5903    3.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4575    0.0536    3.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9743   -1.3527    4.4613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7611   -2.5326    3.1461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8611    0.4232    3.2281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8289   -1.0158    3.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1609   -0.3328    0.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1860   -1.7306    1.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2602   -0.2372    1.8244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0494    1.7941    0.5757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2675    2.9626    0.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1244    1.4047    0.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9378    2.5572   -2.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3209    1.7410   -3.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9917   -0.1358   -2.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7496    0.3094   -1.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8600    1.9087   -3.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9878    2.4842   -2.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1792    0.8890   -0.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2685    2.4265   -0.0409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7049    0.6734    0.4166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4051    1.4292   -1.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3136   -0.1349   -2.4840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1907   -1.0313   -1.1537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4332   -2.2786   -2.1828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0098   -2.0276   -0.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9123   -1.9072   -2.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1637   -0.5616   -2.9290 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2992   -0.7036   -0.1077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4902    0.8038   -0.6160 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2632    1.8656   -2.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9074    2.1470   -1.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7972   -0.5470   -2.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3856    0.6447   -3.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0679   -1.4597   -0.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5879   -0.6991   -0.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8608    0.6402    0.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3282   -0.8808   -0.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7642   -0.6197   -0.6296 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2949   -2.0753    0.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3235    1.1321    2.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1071    1.4352    0.7405 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0822    1.1586    2.1965 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.7005   -0.3384   -0.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6940   -1.8796    0.8151 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3402   -0.3924    1.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1357   -2.0454    2.4600 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8631   -1.9612    2.8219 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7304   -0.7052    3.4582 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  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 28 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 34 36  1  0
 34 37  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  2 41  1  0
  2 42  1  0
  3 43  1  0
  3 44  1  0
  4 45  1  0
  4 46  1  0
  5 47  1  0
  5 48  1  0
  6 49  1  0
  7 50  1  0
  8 51  1  0
  8 52  1  0
  9 53  1  0
 10 54  1  0
 11 55  1  0
 11 56  1  0
 12 57  1  0
 13 58  1  0
 14 59  1  0
 14 60  1  0
 15 61  1  0
 15 62  1  0
 16 63  1  0
 16 64  1  0
 17 65  1  0
 17 66  1  0
 18 67  1  0
 18 68  1  0
 19 69  1  0
 19 70  1  0
 23 71  1  0
 23 72  1  0
 24 73  1  6
 25 74  1  0
 26 75  1  0
 26 76  1  0
 32 77  1  0
 32 78  1  0
 33 79  1  0
 33 80  1  0
 35 81  1  0
 35 82  1  0
 35 83  1  0
 36 84  1  0
 36 85  1  0
 36 86  1  0
 37 87  1  0
 37 88  1  0
 37 89  1  0
M  CHG  2  30  -1  34   1
M  END

LysoPC(20:3(8Z,11Z,14Z)/0:0)
  Mrv1652304202020502D          

 37 36  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
   13.2658   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5516   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8375   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0125   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2984   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5843   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7593   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0452   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3310   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6169   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9028   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1887   -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  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  CHG  2   6   1  11  -1
M  END
> <DATABASE_ID>
HMDB0010394

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C28H52NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-28(31)34-25-27(30)26-36-37(32,33)35-24-23-29(2,3)4/h9-10,12-13,15-16,27,30H,5-8,11,14,17-26H2,1-4H3/b10-9-,13-12-,16-15-/t27-/m1/s1

> <INCHI_KEY>
BBNHCUBQEQJHIG-FZZJNMCHSA-N

> <FORMULA>
C28H52NO7P

> <MOLECULAR_WEIGHT>
545.6887

> <EXACT_MASS>
545.348139535

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
89

> <JCHEM_AVERAGE_POLARIZABILITY>
61.735275281751456

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{[(2R)-2-hydroxy-3-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

> <ALOGPS_LOGP>
2.65

> <JCHEM_LOGP>
1.8852521668615865

> <ALOGPS_LOGS>
-6.48

> <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>
105.12

> <JCHEM_REFRACTIVITY>
164.0275

> <JCHEM_ROTATABLE_BOND_COUNT>
25

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.99e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-{[(2R)-2-hydroxy-3-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0010394
     RDKit          3D
LysoPC(20:3(8Z,11Z,14Z)/0:0)
 89 88  0  0  0  0  0  0  0  0999 V2000
  -11.5040   -1.0827    1.3393 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2579   -1.0013    2.8082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9415   -1.4111    3.3207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7446   -0.6492    2.8993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3941   -0.6270    1.4416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1475    0.1537    1.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0437    1.2473    0.5854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1117    1.8641   -0.1500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0546    1.9789   -1.6035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1485    1.5174   -2.3887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9300    0.7627   -2.1687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8006    1.5617   -2.7199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7502    1.8679   -2.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4369    1.5219   -0.6280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0788    0.7383   -0.5918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2057   -0.5011   -1.3937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1016   -1.4686   -1.4210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2098   -1.0221   -1.8736 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9286   -0.0781   -1.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2500    0.2232   -1.7084 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5262   -0.3111   -2.8124 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1745    1.0878   -1.1533 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3995    1.3754   -1.7827 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2927    0.1974   -1.9700 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4894    0.5215   -2.6051 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5649   -0.5070   -0.6430 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3057    0.3676    0.1178 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7251   -0.2251    1.6414 P   0  0  0  0  0  5  0  0  0  0  0  0
    6.7331    0.9334    2.6385 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6567   -1.3996    2.2011 O   0  0  0  0  0  1  0  0  0  0  0  0
    8.3137   -0.8469    1.6281 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9442   -0.4621    0.4448 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3390   -0.9706    0.3534 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2195   -0.5341    1.3908 N   0  0  0  0  0  4  0  0  0  0  0  0
   11.1323    0.8619    1.6916 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6094   -0.7800    0.9666 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9982   -1.3451    2.5678 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6054   -1.3709    1.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8910   -1.8197    0.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4103   -0.0762    0.8859 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0690   -1.5903    3.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4575    0.0536    3.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9743   -1.3527    4.4613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7611   -2.5326    3.1461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8611    0.4232    3.2281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8289   -1.0158    3.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1609   -0.3328    0.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1860   -1.7306    1.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2602   -0.2372    1.8244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0494    1.7941    0.5757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2675    2.9626    0.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1244    1.4047    0.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9378    2.5572   -2.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3209    1.7410   -3.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9917   -0.1358   -2.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7496    0.3094   -1.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8600    1.9087   -3.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9878    2.4842   -2.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1792    0.8890   -0.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2685    2.4265   -0.0409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7049    0.6734    0.4166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4051    1.4292   -1.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3136   -0.1349   -2.4840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1907   -1.0313   -1.1537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4332   -2.2786   -2.1828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0098   -2.0276   -0.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9123   -1.9072   -2.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1637   -0.5616   -2.9290 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2992   -0.7036   -0.1077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4902    0.8038   -0.6160 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2632    1.8656   -2.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9074    2.1470   -1.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7972   -0.5470   -2.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3856    0.6447   -3.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0679   -1.4597   -0.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5879   -0.6991   -0.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8608    0.6402    0.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3282   -0.8808   -0.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7642   -0.6197   -0.6296 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2949   -2.0753    0.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3235    1.1321    2.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1071    1.4352    0.7405 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0822    1.1586    2.1965 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.7005   -0.3384   -0.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6940   -1.8796    0.8151 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3402   -0.3924    1.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1357   -2.0454    2.4600 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8631   -1.9612    2.8219 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7304   -0.7052    3.4582 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  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 28 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 34 36  1  0
 34 37  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  2 41  1  0
  2 42  1  0
  3 43  1  0
  3 44  1  0
  4 45  1  0
  4 46  1  0
  5 47  1  0
  5 48  1  0
  6 49  1  0
  7 50  1  0
  8 51  1  0
  8 52  1  0
  9 53  1  0
 10 54  1  0
 11 55  1  0
 11 56  1  0
 12 57  1  0
 13 58  1  0
 14 59  1  0
 14 60  1  0
 15 61  1  0
 15 62  1  0
 16 63  1  0
 16 64  1  0
 17 65  1  0
 17 66  1  0
 18 67  1  0
 18 68  1  0
 19 69  1  0
 19 70  1  0
 23 71  1  0
 23 72  1  0
 24 73  1  6
 25 74  1  0
 26 75  1  0
 26 76  1  0
 32 77  1  0
 32 78  1  0
 33 79  1  0
 33 80  1  0
 35 81  1  0
 35 82  1  0
 35 83  1  0
 36 84  1  0
 36 85  1  0
 36 86  1  0
 37 87  1  0
 37 88  1  0
 37 89  1  0
M  CHG  2  30  -1  34   1
M  END

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: LysoPC(20:3(8Z,11Z,14Z)/0:0)                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         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      24.763 -12.188   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      23.430 -11.417   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      22.097 -12.188   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      20.557 -12.188   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      19.224 -11.417   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      17.891 -12.188   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      16.351 -12.188   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      15.018 -11.417   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      13.685 -12.188   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      12.352 -11.417   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      11.019 -12.188   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.686 -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   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   72    0
END

COMPND    HMDB0010394
HETATM    1  C1  UNL     1     -11.504  -1.083   1.339  1.00  0.00           C  
HETATM    2  C2  UNL     1     -11.258  -1.001   2.808  1.00  0.00           C  
HETATM    3  C3  UNL     1      -9.942  -1.411   3.321  1.00  0.00           C  
HETATM    4  C4  UNL     1      -8.745  -0.649   2.899  1.00  0.00           C  
HETATM    5  C5  UNL     1      -8.394  -0.627   1.442  1.00  0.00           C  
HETATM    6  C6  UNL     1      -7.148   0.154   1.291  1.00  0.00           C  
HETATM    7  C7  UNL     1      -7.044   1.247   0.585  1.00  0.00           C  
HETATM    8  C8  UNL     1      -8.112   1.864  -0.150  1.00  0.00           C  
HETATM    9  C9  UNL     1      -8.055   1.979  -1.604  1.00  0.00           C  
HETATM   10  C10 UNL     1      -7.149   1.517  -2.389  1.00  0.00           C  
HETATM   11  C11 UNL     1      -5.930   0.763  -2.169  1.00  0.00           C  
HETATM   12  C12 UNL     1      -4.801   1.562  -2.720  1.00  0.00           C  
HETATM   13  C13 UNL     1      -3.750   1.868  -2.018  1.00  0.00           C  
HETATM   14  C14 UNL     1      -3.437   1.522  -0.628  1.00  0.00           C  
HETATM   15  C15 UNL     1      -2.079   0.738  -0.592  1.00  0.00           C  
HETATM   16  C16 UNL     1      -2.206  -0.501  -1.394  1.00  0.00           C  
HETATM   17  C17 UNL     1      -1.102  -1.469  -1.421  1.00  0.00           C  
HETATM   18  C18 UNL     1       0.210  -1.022  -1.874  1.00  0.00           C  
HETATM   19  C19 UNL     1       0.929  -0.078  -1.005  1.00  0.00           C  
HETATM   20  C20 UNL     1       2.250   0.223  -1.708  1.00  0.00           C  
HETATM   21  O1  UNL     1       2.526  -0.311  -2.812  1.00  0.00           O  
HETATM   22  O2  UNL     1       3.175   1.088  -1.153  1.00  0.00           O  
HETATM   23  C21 UNL     1       4.400   1.375  -1.783  1.00  0.00           C  
HETATM   24  C22 UNL     1       5.293   0.197  -1.970  1.00  0.00           C  
HETATM   25  O3  UNL     1       6.489   0.521  -2.605  1.00  0.00           O  
HETATM   26  C23 UNL     1       5.565  -0.507  -0.643  1.00  0.00           C  
HETATM   27  O4  UNL     1       6.306   0.368   0.118  1.00  0.00           O  
HETATM   28  P1  UNL     1       6.725  -0.225   1.641  1.00  0.00           P  
HETATM   29  O5  UNL     1       6.733   0.933   2.639  1.00  0.00           O  
HETATM   30  O6  UNL     1       5.657  -1.400   2.201  1.00  0.00           O1-
HETATM   31  O7  UNL     1       8.314  -0.847   1.628  1.00  0.00           O  
HETATM   32  C24 UNL     1       8.944  -0.462   0.445  1.00  0.00           C  
HETATM   33  C25 UNL     1      10.339  -0.971   0.353  1.00  0.00           C  
HETATM   34  N1  UNL     1      11.219  -0.534   1.391  1.00  0.00           N1+
HETATM   35  C26 UNL     1      11.132   0.862   1.692  1.00  0.00           C  
HETATM   36  C27 UNL     1      12.609  -0.780   0.967  1.00  0.00           C  
HETATM   37  C28 UNL     1      10.998  -1.345   2.568  1.00  0.00           C  
HETATM   38  H1  UNL     1     -12.605  -1.371   1.144  1.00  0.00           H  
HETATM   39  H2  UNL     1     -10.891  -1.820   0.800  1.00  0.00           H  
HETATM   40  H3  UNL     1     -11.410  -0.076   0.886  1.00  0.00           H  
HETATM   41  H4  UNL     1     -12.069  -1.590   3.348  1.00  0.00           H  
HETATM   42  H5  UNL     1     -11.458   0.054   3.182  1.00  0.00           H  
HETATM   43  H6  UNL     1      -9.974  -1.353   4.461  1.00  0.00           H  
HETATM   44  H7  UNL     1      -9.761  -2.533   3.146  1.00  0.00           H  
HETATM   45  H8  UNL     1      -8.861   0.423   3.228  1.00  0.00           H  
HETATM   46  H9  UNL     1      -7.829  -1.016   3.479  1.00  0.00           H  
HETATM   47  H10 UNL     1      -9.161  -0.333   0.753  1.00  0.00           H  
HETATM   48  H11 UNL     1      -8.186  -1.731   1.190  1.00  0.00           H  
HETATM   49  H12 UNL     1      -6.260  -0.237   1.824  1.00  0.00           H  
HETATM   50  H13 UNL     1      -6.049   1.794   0.576  1.00  0.00           H  
HETATM   51  H14 UNL     1      -8.268   2.963   0.215  1.00  0.00           H  
HETATM   52  H15 UNL     1      -9.124   1.405   0.084  1.00  0.00           H  
HETATM   53  H16 UNL     1      -8.938   2.557  -2.094  1.00  0.00           H  
HETATM   54  H17 UNL     1      -7.321   1.741  -3.498  1.00  0.00           H  
HETATM   55  H18 UNL     1      -5.992  -0.136  -2.887  1.00  0.00           H  
HETATM   56  H19 UNL     1      -5.750   0.309  -1.209  1.00  0.00           H  
HETATM   57  H20 UNL     1      -4.860   1.909  -3.774  1.00  0.00           H  
HETATM   58  H21 UNL     1      -2.988   2.484  -2.572  1.00  0.00           H  
HETATM   59  H22 UNL     1      -4.179   0.889  -0.114  1.00  0.00           H  
HETATM   60  H23 UNL     1      -3.268   2.426  -0.041  1.00  0.00           H  
HETATM   61  H24 UNL     1      -1.705   0.673   0.417  1.00  0.00           H  
HETATM   62  H25 UNL     1      -1.405   1.429  -1.183  1.00  0.00           H  
HETATM   63  H26 UNL     1      -2.314  -0.135  -2.484  1.00  0.00           H  
HETATM   64  H27 UNL     1      -3.191  -1.031  -1.154  1.00  0.00           H  
HETATM   65  H28 UNL     1      -1.433  -2.279  -2.183  1.00  0.00           H  
HETATM   66  H29 UNL     1      -1.010  -2.028  -0.426  1.00  0.00           H  
HETATM   67  H30 UNL     1       0.912  -1.907  -2.093  1.00  0.00           H  
HETATM   68  H31 UNL     1       0.164  -0.562  -2.929  1.00  0.00           H  
HETATM   69  H32 UNL     1       1.299  -0.704  -0.108  1.00  0.00           H  
HETATM   70  H33 UNL     1       0.490   0.804  -0.616  1.00  0.00           H  
HETATM   71  H34 UNL     1       4.263   1.866  -2.771  1.00  0.00           H  
HETATM   72  H35 UNL     1       4.907   2.147  -1.139  1.00  0.00           H  
HETATM   73  H36 UNL     1       4.797  -0.547  -2.620  1.00  0.00           H  
HETATM   74  H37 UNL     1       6.386   0.645  -3.569  1.00  0.00           H  
HETATM   75  H38 UNL     1       6.068  -1.460  -0.893  1.00  0.00           H  
HETATM   76  H39 UNL     1       4.588  -0.699  -0.147  1.00  0.00           H  
HETATM   77  H40 UNL     1       8.861   0.640   0.340  1.00  0.00           H  
HETATM   78  H41 UNL     1       8.328  -0.881  -0.389  1.00  0.00           H  
HETATM   79  H42 UNL     1      10.764  -0.620  -0.630  1.00  0.00           H  
HETATM   80  H43 UNL     1      10.295  -2.075   0.275  1.00  0.00           H  
HETATM   81  H44 UNL     1      10.323   1.132   2.390  1.00  0.00           H  
HETATM   82  H45 UNL     1      11.107   1.435   0.741  1.00  0.00           H  
HETATM   83  H46 UNL     1      12.082   1.159   2.197  1.00  0.00           H  
HETATM   84  H47 UNL     1      12.700  -0.338  -0.052  1.00  0.00           H  
HETATM   85  H48 UNL     1      12.694  -1.880   0.815  1.00  0.00           H  
HETATM   86  H49 UNL     1      13.340  -0.392   1.685  1.00  0.00           H  
HETATM   87  H50 UNL     1      10.136  -2.045   2.460  1.00  0.00           H  
HETATM   88  H51 UNL     1      11.863  -1.961   2.822  1.00  0.00           H  
HETATM   89  H52 UNL     1      10.730  -0.705   3.458  1.00  0.00           H  
CONECT    1    2   38   39   40
CONECT    2    3   41   42
CONECT    3    4   43   44
CONECT    4    5   45   46
CONECT    5    6   47   48
CONECT    6    7    7   49
CONECT    7    8   50
CONECT    8    9   51   52
CONECT    9   10   10   53
CONECT   10   11   54
CONECT   11   12   55   56
CONECT   12   13   13   57
CONECT   13   14   58
CONECT   14   15   59   60
CONECT   15   16   61   62
CONECT   16   17   63   64
CONECT   17   18   65   66
CONECT   18   19   67   68
CONECT   19   20   69   70
CONECT   20   21   21   22
CONECT   22   23
CONECT   23   24   71   72
CONECT   24   25   26   73
CONECT   25   74
CONECT   26   27   75   76
CONECT   27   28
CONECT   28   29   29   30   31
CONECT   31   32
CONECT   32   33   77   78
CONECT   33   34   79   80
CONECT   34   35   36   37
CONECT   35   81   82   83
CONECT   36   84   85   86
CONECT   37   87   88   89
END

HMDB0010394
     RDKit          3D
LysoPC(20:3(8Z,11Z,14Z)/0:0)
 89 88  0  0  0  0  0  0  0  0999 V2000
  -11.5040   -1.0827    1.3393 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2579   -1.0013    2.8082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9415   -1.4111    3.3207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7446   -0.6492    2.8993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3941   -0.6270    1.4416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1475    0.1537    1.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0437    1.2473    0.5854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1117    1.8641   -0.1500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0546    1.9789   -1.6035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1485    1.5174   -2.3887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9300    0.7627   -2.1687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8006    1.5617   -2.7199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7502    1.8679   -2.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4369    1.5219   -0.6280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0788    0.7383   -0.5918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2057   -0.5011   -1.3937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1016   -1.4686   -1.4210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2098   -1.0221   -1.8736 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9286   -0.0781   -1.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2500    0.2232   -1.7084 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5262   -0.3111   -2.8124 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1745    1.0878   -1.1533 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3995    1.3754   -1.7827 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2927    0.1974   -1.9700 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4894    0.5215   -2.6051 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5649   -0.5070   -0.6430 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3057    0.3676    0.1178 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7251   -0.2251    1.6414 P   0  0  0  0  0  5  0  0  0  0  0  0
    6.7331    0.9334    2.6385 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6567   -1.3996    2.2011 O   0  0  0  0  0  1  0  0  0  0  0  0
    8.3137   -0.8469    1.6281 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9442   -0.4621    0.4448 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3390   -0.9706    0.3534 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2195   -0.5341    1.3908 N   0  0  0  0  0  4  0  0  0  0  0  0
   11.1323    0.8619    1.6916 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6094   -0.7800    0.9666 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9982   -1.3451    2.5678 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6054   -1.3709    1.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8910   -1.8197    0.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4103   -0.0762    0.8859 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0690   -1.5903    3.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4575    0.0536    3.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9743   -1.3527    4.4613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7611   -2.5326    3.1461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8611    0.4232    3.2281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8289   -1.0158    3.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1609   -0.3328    0.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1860   -1.7306    1.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2602   -0.2372    1.8244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0494    1.7941    0.5757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2675    2.9626    0.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1244    1.4047    0.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9378    2.5572   -2.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3209    1.7410   -3.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9917   -0.1358   -2.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7496    0.3094   -1.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8600    1.9087   -3.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9878    2.4842   -2.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1792    0.8890   -0.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2685    2.4265   -0.0409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7049    0.6734    0.4166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4051    1.4292   -1.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3136   -0.1349   -2.4840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1907   -1.0313   -1.1537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4332   -2.2786   -2.1828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0098   -2.0276   -0.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9123   -1.9072   -2.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1637   -0.5616   -2.9290 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2992   -0.7036   -0.1077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4902    0.8038   -0.6160 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2632    1.8656   -2.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9074    2.1470   -1.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7972   -0.5470   -2.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3856    0.6447   -3.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0679   -1.4597   -0.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5879   -0.6991   -0.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8608    0.6402    0.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3282   -0.8808   -0.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7642   -0.6197   -0.6296 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2949   -2.0753    0.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3235    1.1321    2.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1071    1.4352    0.7405 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0822    1.1586    2.1965 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.7005   -0.3384   -0.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6940   -1.8796    0.8151 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3402   -0.3924    1.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1357   -2.0454    2.4600 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8631   -1.9612    2.8219 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7304   -0.7052    3.4582 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  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 28 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 34 36  1  0
 34 37  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  2 41  1  0
  2 42  1  0
  3 43  1  0
  3 44  1  0
  4 45  1  0
  4 46  1  0
  5 47  1  0
  5 48  1  0
  6 49  1  0
  7 50  1  0
  8 51  1  0
  8 52  1  0
  9 53  1  0
 10 54  1  0
 11 55  1  0
 11 56  1  0
 12 57  1  0
 13 58  1  0
 14 59  1  0
 14 60  1  0
 15 61  1  0
 15 62  1  0
 16 63  1  0
 16 64  1  0
 17 65  1  0
 17 66  1  0
 18 67  1  0
 18 68  1  0
 19 69  1  0
 19 70  1  0
 23 71  1  0
 23 72  1  0
 24 73  1  6
 25 74  1  0
 26 75  1  0
 26 76  1  0
 32 77  1  0
 32 78  1  0
 33 79  1  0
 33 80  1  0
 35 81  1  0
 35 82  1  0
 35 83  1  0
 36 84  1  0
 36 85  1  0
 36 86  1  0
 37 87  1  0
 37 88  1  0
 37 89  1  0
M  CHG  2  30  -1  34   1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-[(8Z,11Z,14Z)-Eicosatrienoyl]-sn-glycero-3-phosphocholine	ChEBI
1-Dihomo-linolenoyl-GPC	ChEBI
1-Dihomo-linolenoyl-GPC(20:3n6)	ChEBI
1-Homo-gamma-linolenoyl-glycero-3-phosphocholine	ChEBI
GPC(20:3n6)	ChEBI
GPC(20:3n6/0:0)	ChEBI
LPC(20:3)	ChEBI
LysoPC(20:3)	ChEBI
Lysophosphatidylcholine(20:3)	ChEBI
1-Homo-g-linolenoyl-glycero-3-phosphocholine	Generator
1-Homo-γ-linolenoyl-glycero-3-phosphocholine	Generator
LyPC(20:3/0:0)	Lipid Annotator, HMDB
LysoPC(20:3(8Z,11Z,14Z))	Lipid Annotator
LPC(20:3/0:0)	Lipid Annotator, HMDB
LysoPC(20:3/0:0)	Lipid Annotator, HMDB
LyPC(20:3)	Lipid Annotator, HMDB
1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphocholine	Lipid Annotator, HMDB
Lysophosphatidylcholine(20:3/0:0)	Lipid Annotator, HMDB
LPC(20:3n6/0:0)	HMDB
LPC(20:3W6/0:0)	HMDB
LyPC(20:3n6/0:0)	HMDB
LyPC(20:3W6/0:0)	HMDB
LysoPC a C20:3	HMDB
LysoPC(20:3n6/0:0)	HMDB
LysoPC(20:3W6/0:0)	HMDB
Lysophosphatidylcholine(20:3n6/0:0)	HMDB
Lysophosphatidylcholine(20:3W6/0:0)	HMDB
1-Dihomo-gamma-linolenoyl-GPC	HMDB
1-Dihomo-gamma-linolenoyl-lysophosphatidylcholine	HMDB
1-Dihomo-gamma-linolenoyl-sn-glycero-3-phosphocholine	HMDB
GPC(20:3(8Z,11Z,14Z))	HMDB
GPC(20:3(8Z,11Z,14Z)/0:0)	HMDB
GPC(20:3)	HMDB
GPC(20:3w6)	HMDB
GPC(20:3w6/0:0)	HMDB
LPC(20:3(8Z,11Z,14Z))	HMDB
LPC(20:3(8Z,11Z,14Z)/0:0)	HMDB
LPC(20:3n6)	HMDB
LPC(20:3w6)	HMDB
LysoPC(20:3(8Z,11Z,14Z)/0:0)	HMDB
LysoPC(20:3n6)	HMDB
LysoPC(20:3w6)	HMDB
Lysophosphatidylcholine(20:3(8Z,11Z,14Z))	HMDB
Lysophosphatidylcholine(20:3(8Z,11Z,14Z)/0:0)	HMDB
Lysophosphatidylcholine(20:3n6)	HMDB
Lysophosphatidylcholine(20:3w6)	HMDB

Chemical Formula

C₂₈H₅₂NO₇P

Average Molecular Weight

545.6887

Monoisotopic Molecular Weight

545.348139535

IUPAC Name

(2-{[(2R)-2-hydroxy-3-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-2-hydroxy-3-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

1006703-11-2

SMILES

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

InChI Identifier

InChI=1S/C28H52NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-28(31)34-25-27(30)26-36-37(32,33)35-24-23-29(2,3)4/h9-10,12-13,15-16,27,30H,5-8,11,14,17-26H2,1-4H3/b10-9-,13-12-,16-15-/t27-/m1/s1

InChI Key

BBNHCUBQEQJHIG-FZZJNMCHSA-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 20:3 (CHEBI:86256 )
1-O-acyl-sn-glycero-3-phosphocholine (CHEBI:86256 )
Monoacylglycerophosphocholines (LMGP01050133 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0002 g/L	ALOGPS
logP	2.65	ALOGPS
logP	1.89	ChemAxon
logS	-6.5	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	164.03 m³·mol⁻¹	ChemAxon
Polarizability	61.74 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]+	226.14	30932474
DeepCCS	[M-H]-	222.843	30932474
DeepCCS	[M-2H]-	257.092	30932474
DeepCCS	[M+Na]+	233.491	30932474
AllCCS	[M+H]+	238.5	32859911
AllCCS	[M+H-H2O]+	237.3	32859911
AllCCS	[M+NH4]+	239.6	32859911
AllCCS	[M+Na]+	239.9	32859911
AllCCS	[M-H]-	234.9	32859911
AllCCS	[M+Na-2H]-	238.5	32859911
AllCCS	[M+HCOO]-	242.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
LysoPC(20:3(8Z,11Z,14Z)/0:0)	CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C	4134.8	Standard polar	33892256
LysoPC(20:3(8Z,11Z,14Z)/0:0)	CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C	3128.6	Standard non polar	33892256
LysoPC(20:3(8Z,11Z,14Z)/0:0)	CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C	3669.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
LysoPC(20:3(8Z,11Z,14Z)/0:0),1TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O[Si](C)(C)C	3700.2	Semi standard non polar	33892256
LysoPC(20:3(8Z,11Z,14Z)/0:0),1TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C	3926.1	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(20:3(8Z,11Z,14Z)/0:0) GC-MS (Non-derivatized) - 70eV, Positive	splash10-007t-4940200000-539a8f6feb74a21a66dc	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - LysoPC(20:3(8Z,11Z,14Z)/0:0) GC-MS (1 TMS) - 70eV, Positive	splash10-0irc-9631012000-81b6c55072101312aa6a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - LysoPC(20:3(8Z,11Z,14Z)/0:0) GC-MS ("LysoPC(20:3(8Z,11Z,14Z)/0:0),1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - LysoPC(20:3(8Z,11Z,14Z)/0:0) GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-14	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(20:3(8Z,11Z,14Z)/0:0) 10V, Positive-QTOF	splash10-000i-9153130000-18fae725515f180cca64	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(20:3(8Z,11Z,14Z)/0:0) 20V, Positive-QTOF	splash10-01p9-9484010000-be7a34a51ea184e42e3b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(20:3(8Z,11Z,14Z)/0:0) 40V, Positive-QTOF	splash10-000i-9041000000-5ebe0c1f89b46b467f2d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(20:3(8Z,11Z,14Z)/0:0) 10V, Negative-QTOF	splash10-0a4u-0079170000-c78131971d03e5de90c9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(20:3(8Z,11Z,14Z)/0:0) 20V, Negative-QTOF	splash10-0a4r-0059200000-7b3a58f9bbf54cc35ddc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(20:3(8Z,11Z,14Z)/0:0) 40V, Negative-QTOF	splash10-0a4i-8279000000-17f06d050dc6537981ba	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(20:3(8Z,11Z,14Z)/0:0) 10V, Positive-QTOF	splash10-014i-0000090000-2fa9e2dacbd579d98321	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(20:3(8Z,11Z,14Z)/0:0) 20V, Positive-QTOF	splash10-0aor-0000090000-4e0d8983cb3993c06087	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(20:3(8Z,11Z,14Z)/0:0) 40V, Positive-QTOF	splash10-0k9i-1609090000-d5aa77469dc8dbc46c34	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(20:3(8Z,11Z,14Z)/0:0) 10V, Negative-QTOF	splash10-001i-0000090000-91dea8ecfdf79e4e7a22	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(20:3(8Z,11Z,14Z)/0:0) 20V, Negative-QTOF	splash10-0a59-0009070000-4ff84ef3f56eac796f10	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(20:3(8Z,11Z,14Z)/0:0) 40V, Negative-QTOF	splash10-0a4i-0039030000-159be9a74a8e1e30d620	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(20:3(8Z,11Z,14Z)/0:0) 10V, Negative-QTOF	splash10-0006-0003090000-5f23f15b3d1cddc86c7c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(20:3(8Z,11Z,14Z)/0:0) 20V, Negative-QTOF	splash10-0a4i-1019010000-f0ec184501a709e17d8d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(20:3(8Z,11Z,14Z)/0:0) 40V, Negative-QTOF	splash10-0a4i-1009000000-33adea1b71d9d85ebe36	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(20:3(8Z,11Z,14Z)/0:0) 10V, Positive-QTOF	splash10-002b-0000090000-bf7fc3df698e870dec69	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(20:3(8Z,11Z,14Z)/0:0) 20V, Positive-QTOF	splash10-001j-0900060000-e960f0563ba251b8e278	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(20:3(8Z,11Z,14Z)/0:0) 40V, Positive-QTOF	splash10-0fai-0910040000-a85b3fe6a7ba7ef759c7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(20:3(8Z,11Z,14Z)/0:0) 10V, Positive-QTOF	splash10-0udi-0000190000-a0ae6730d99da9a4c0a5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(20:3(8Z,11Z,14Z)/0:0) 20V, Positive-QTOF	splash10-0udo-0002990000-8cd2eede2fa4ae6a1a81	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(20:3(8Z,11Z,14Z)/0:0) 40V, Positive-QTOF	splash10-0j4l-0309400000-92edf5aa3d34b1285d04	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

All Tissues

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	2.65 +/- 0.68 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	2.75 +/- 0.29 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	2.749 +/- 0.291 uM	Adult (>18 years old)	Both	Normal	18953024	details
Blood	Detected and Quantified	3.32 (2.74-4.02) uM	Newborn (0-30 days old)	Not Available	Normal	25754623	details
Blood	Detected and Quantified	2.64(0.72) uM	Adult (>18 years old)	Both	Normal	26010610	details
Blood	Detected and Quantified	1.75 +/- 0.56 uM	Adult (>18 years old)	Both	Normal	28278231	details
Blood	Detected and Quantified	1.61 (1.28-2.06) uM	Infant (0-1 year old)	Not Available	Normal	25754623	details
Feces	Detected and Quantified	0.13 +/- 0.09 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected and Quantified	0.17 +/- 0.15 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	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 and Quantified	2.2(0.79) uM	Adult (>18 years old)	Both	Heart failure with preserved ejection fraction	26010610	details
Blood	Detected and Quantified	1.6375 (1.5461) uM	Adult (>18 years old)	Female	Pregnancy with fetus having congenital heart defect	24704061	details
Blood	Detected and Quantified	2.7411 (1.1319) uM	Adult (>18 years old)	Female	Pregnancy	24704061	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 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

21403156

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

52924055

PDB ID

Not Available

ChEBI ID

86256

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(20:3(8Z,11Z,14Z)/0:0) (HMDB0010394)

MOL for HMDB0010394 (LysoPC(20:3(8Z,11Z,14Z)/0:0))

3D MOL for HMDB0010394 (LysoPC(20:3(8Z,11Z,14Z)/0:0))

3D SDF for HMDB0010394 (LysoPC(20:3(8Z,11Z,14Z)/0:0))

3D-SDF for HMDB0010394 (LysoPC(20:3(8Z,11Z,14Z)/0:0))

PDB for HMDB0010394 (LysoPC(20:3(8Z,11Z,14Z)/0:0))

3D PDB for HMDB0010394 (LysoPC(20:3(8Z,11Z,14Z)/0:0))

SMILES for HMDB0010394 (LysoPC(20:3(8Z,11Z,14Z)/0:0))

INCHI for HMDB0010394 (LysoPC(20:3(8Z,11Z,14Z)/0:0))

Structure for HMDB0010394 (LysoPC(20:3(8Z,11Z,14Z)/0:0))

3D Structure for HMDB0010394 (LysoPC(20:3(8Z,11Z,14Z)/0:0))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes