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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2008-09-16 13:19:58 UTC

Update Date

2022-07-14 16:57:34 UTC

HMDB ID

HMDB0010384

Secondary Accession Numbers

HMDB0094688
HMDB10384
HMDB94688

Metabolite Identification

Common Name

LysoPC(18:0/0:0)

Description

LysoPC(18:0) 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(18:0), in particular, consists of one chain of stearic acid at the C-1 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil. 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

PC(18:0/0:0)
  Mrv1652303192020102D          

 36 35  0  0  0  0            999 V2000
   -3.8021    0.3608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9591    0.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2447    0.7720    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6571    1.4866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1679    0.0575    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -3.0969    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3824    0.3590    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6679    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9699   -0.3555    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7950   -0.3555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    1.1846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1844    0.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8988    1.1846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6132    0.7721    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.2007    0.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2744    1.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3277    0.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5121    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5121    1.5410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2263    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9404    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6545    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3686    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0827    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7969    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5110    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2251    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9392    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6534    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3675    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0816    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.7957    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.5098    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.2240    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.9381    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.6522    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  7  9  1  1  0  0  0
  6  1  1  0  0  0  0
  2  8  1  0  0  0  0
  7 10  1  6  0  0  0
  1 18  1  0  0  0  0
 11 12  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
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 11  3  1  0  0  0  0
 18 19  2  0  0  0  0
 18 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
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  CHG  2   5  -1  14   1
M  END

HMDB0010384
     RDKit          3D
LysoPC(18:0/0:0)
 89 88  0  0  0  0  0  0  0  0999 V2000
  -12.2317   -1.9658   -0.6617 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2145   -1.2262    0.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3518   -0.3038   -0.6666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5805   -1.0610   -1.7263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6762   -2.0920   -1.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6387   -1.4942   -0.1761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8231   -0.5401   -0.9656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7172    0.0898   -0.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3098    0.8433    1.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3924    1.5413    1.9392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5344    2.6353    1.4860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5279    2.4371    0.4341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5000    1.3509    0.7094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7123    1.6166    1.9380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7324    0.5632    2.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4183    0.3106    1.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3126   -0.0520   -0.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7398   -0.3632   -0.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1432   -1.5409   -0.4275 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5701    0.6115   -0.8962 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8800    0.5281   -1.3428 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8933    0.0162   -0.3703 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6451   -1.2719    0.0794 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2392   -0.0645   -1.1103 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5138    1.2047   -1.5551 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9547    1.3458   -2.4148 P   0  0  0  0  0  5  0  0  0  0  0  0
    7.9849    2.7681   -2.9578 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0118    0.2368   -3.7140 O   0  0  0  0  0  1  0  0  0  0  0  0
    9.2815    1.0305   -1.4405 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8783   -0.1772   -1.7110 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0779   -0.4931   -0.8898 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8723   -0.5558    0.5185 N   0  0  0  0  0  4  0  0  0  0  0  0
   11.4966    0.6349    1.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5150   -1.7174    1.1189 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5054   -0.5572    0.9496 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2329   -1.6511   -1.7350 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.2594   -1.7964   -0.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0079   -3.0487   -0.5803 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7582   -0.5668    0.8930 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5643   -1.8760    0.7572 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9403    0.4753   -1.1841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6405    0.1954   -0.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1094   -0.3373   -2.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3012   -1.6363   -2.3785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0996   -2.5721   -1.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3061   -2.8023   -0.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1606   -1.0229    0.6856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0010   -2.3288    0.1448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4282    0.2674   -1.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3743   -1.1187   -1.8223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1028    0.6418   -0.8326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0521   -0.7280    0.2670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1354    1.5088    0.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8932    0.0677    1.6117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0760    1.9957    2.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8405    0.7674    2.5538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2384    3.4486    1.0867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1054    3.1492    2.3952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9012    2.4823   -0.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8696    3.3968    0.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9773    0.3495    0.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8710    1.3302   -0.1768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4639    1.7677    2.7712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2006    2.6242    1.8699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2567   -0.4428    2.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3345    0.8206    3.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1119    1.2222    1.4568 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0868   -0.4788    1.8956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1126    0.8893   -0.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3680   -0.8671   -0.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1905    1.5791   -1.6212 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9772   -0.0261   -2.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0710    0.7208    0.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1399   -1.9387   -0.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1100   -0.7985   -1.9573 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9800   -0.4729   -0.4254 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1371   -1.0303   -1.7080 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2226   -0.1337   -2.7827 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8739    0.2426   -1.1464 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4724   -1.4775   -1.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7330    1.4454    1.0325 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3651    0.9177    0.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7891    0.4568    2.1590 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0986   -2.2935    0.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7660   -2.4240    1.5312 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1669   -1.4234    1.9665 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9852    0.3925    0.7927 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5316   -0.7166    2.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9581   -1.4337    0.5453 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  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 26 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 32 34  1  0
 32 35  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  0
  2 40  1  0
  3 41  1  0
  3 42  1  0
  4 43  1  0
  4 44  1  0
  5 45  1  0
  5 46  1  0
  6 47  1  0
  6 48  1  0
  7 49  1  0
  7 50  1  0
  8 51  1  0
  8 52  1  0
  9 53  1  0
  9 54  1  0
 10 55  1  0
 10 56  1  0
 11 57  1  0
 11 58  1  0
 12 59  1  0
 12 60  1  0
 13 61  1  0
 13 62  1  0
 14 63  1  0
 14 64  1  0
 15 65  1  0
 15 66  1  0
 16 67  1  0
 16 68  1  0
 17 69  1  0
 17 70  1  0
 21 71  1  0
 21 72  1  0
 22 73  1  1
 23 74  1  0
 24 75  1  0
 24 76  1  0
 30 77  1  0
 30 78  1  0
 31 79  1  0
 31 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
 35 87  1  0
 35 88  1  0
 35 89  1  0
M  CHG  2  28  -1  32   1
M  END

PC(18:0/0:0)
  Mrv1652303192020102D          

 36 35  0  0  0  0            999 V2000
   -3.8021    0.3608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9591    0.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2447    0.7720    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6571    1.4866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1679    0.0575    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -3.0969    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3824    0.3590    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6679    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9699   -0.3555    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1844    0.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8988    1.1846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6132    0.7721    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.2007    0.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2744    1.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3277    0.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5121    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5121    1.5410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  -11.6534    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3675    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0816    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.7957    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.5098    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.2240    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.9381    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.6522    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  7  9  1  1  0  0  0
  6  1  1  0  0  0  0
  2  8  1  0  0  0  0
  7 10  1  6  0  0  0
  1 18  1  0  0  0  0
 11 12  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
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 11  3  1  0  0  0  0
 18 19  2  0  0  0  0
 18 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
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  CHG  2   5  -1  14   1
M  END
> <DATABASE_ID>
HMDB0010384

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C26H54NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26(29)32-23-25(28)24-34-35(30,31)33-22-21-27(2,3)4/h25,28H,5-24H2,1-4H3/t25-/m1/s1

> <INCHI_KEY>
IHNKQIMGVNPMTC-RUZDIDTESA-N

> <FORMULA>
C26H54NO7P

> <MOLECULAR_WEIGHT>
523.6832

> <EXACT_MASS>
523.363789599

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
89

> <JCHEM_AVERAGE_POLARIZABILITY>
61.70957079930074

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
2.53

> <JCHEM_LOGP>
2.081879806861589

> <ALOGPS_LOGS>
-6.41

> <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>
151.47570000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
26

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.27e-04 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0010384
     RDKit          3D
LysoPC(18:0/0:0)
 89 88  0  0  0  0  0  0  0  0999 V2000
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   -7.1354    1.5088    0.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.1054    3.1492    2.3952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9012    2.4823   -0.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8696    3.3968    0.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9773    0.3495    0.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8710    1.3302   -0.1768 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2006    2.6242    1.8699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2567   -0.4428    2.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3345    0.8206    3.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1119    1.2222    1.4568 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0868   -0.4788    1.8956 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1399   -1.9387   -0.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.9800   -0.4729   -0.4254 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1371   -1.0303   -1.7080 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2226   -0.1337   -2.7827 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8739    0.2426   -1.1464 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4724   -1.4775   -1.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7330    1.4454    1.0325 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3651    0.9177    0.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
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   10.7660   -2.4240    1.5312 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1669   -1.4234    1.9665 H   0  0  0  0  0  0  0  0  0  0  0  0
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  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
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 13 14  1  0
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 18 19  2  0
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 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
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 26 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 32 34  1  0
 32 35  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  0
  2 40  1  0
  3 41  1  0
  3 42  1  0
  4 43  1  0
  4 44  1  0
  5 45  1  0
  5 46  1  0
  6 47  1  0
  6 48  1  0
  7 49  1  0
  7 50  1  0
  8 51  1  0
  8 52  1  0
  9 53  1  0
  9 54  1  0
 10 55  1  0
 10 56  1  0
 11 57  1  0
 11 58  1  0
 12 59  1  0
 12 60  1  0
 13 61  1  0
 13 62  1  0
 14 63  1  0
 14 64  1  0
 15 65  1  0
 15 66  1  0
 16 67  1  0
 16 68  1  0
 17 69  1  0
 17 70  1  0
 21 71  1  0
 21 72  1  0
 22 73  1  1
 23 74  1  0
 24 75  1  0
 24 76  1  0
 30 77  1  0
 30 78  1  0
 31 79  1  0
 31 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
 35 87  1  0
 35 88  1  0
 35 89  1  0
M  CHG  2  28  -1  32   1
M  END

HEADER    PROTEIN                                 19-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: PC(18:0/0:0)                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-MAR-20         0                                  
HETATM    1  O   UNK     0      -7.097   0.673   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      -1.790   0.671   0.000  0.00  0.00           O+0
HETATM    3  P   UNK     0      -0.457   1.441   0.000  0.00  0.00           P+0
HETATM    4  O   UNK     0      -1.227   2.775   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       0.313   0.107   0.000  0.00  0.00           O-1
HETATM    6  C   UNK     0      -5.781   1.440   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.447   0.670   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.113   1.440   0.000  0.00  0.00           C+0
HETATM    9  H   UNK     0      -3.677  -0.664   0.000  0.00  0.00           H+0
HETATM   10  O   UNK     0      -5.217  -0.664   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.877   2.211   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.211   1.441   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.544   2.211   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       4.878   1.441   0.000  0.00  0.00           N+1
HETATM   15  C   UNK     0       4.108   0.108   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.112   3.054   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.212   0.671   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -8.423   1.436   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -8.423   2.876   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -9.756   0.665   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -11.089   1.436   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -12.422   0.665   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -13.755   1.436   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -15.088   0.665   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -16.421   1.436   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -17.754   0.665   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -19.087   1.436   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -20.420   0.665   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -21.753   1.436   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -23.086   0.665   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -24.419   1.436   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -25.752   0.665   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -27.085   1.436   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -28.418   0.665   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -29.751   1.436   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -31.084   0.665   0.000  0.00  0.00           C+0
CONECT    1    6   18                                                       
CONECT    2    3    8                                                       
CONECT    3    2    4    5   11                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    7    1                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7    2                                                       
CONECT    9    7                                                            
CONECT   10    7                                                            
CONECT   11   12    3                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14                                                            
CONECT   18    1   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   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                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   70    0
END

COMPND    HMDB0010384
HETATM    1  C1  UNL     1     -12.232  -1.966  -0.662  1.00  0.00           C  
HETATM    2  C2  UNL     1     -11.215  -1.226   0.158  1.00  0.00           C  
HETATM    3  C3  UNL     1     -10.352  -0.304  -0.667  1.00  0.00           C  
HETATM    4  C4  UNL     1      -9.581  -1.061  -1.726  1.00  0.00           C  
HETATM    5  C5  UNL     1      -8.676  -2.092  -1.127  1.00  0.00           C  
HETATM    6  C6  UNL     1      -7.639  -1.494  -0.176  1.00  0.00           C  
HETATM    7  C7  UNL     1      -6.823  -0.540  -0.966  1.00  0.00           C  
HETATM    8  C8  UNL     1      -5.717   0.090  -0.126  1.00  0.00           C  
HETATM    9  C9  UNL     1      -6.310   0.843   1.008  1.00  0.00           C  
HETATM   10  C10 UNL     1      -5.392   1.541   1.939  1.00  0.00           C  
HETATM   11  C11 UNL     1      -4.534   2.635   1.486  1.00  0.00           C  
HETATM   12  C12 UNL     1      -3.528   2.437   0.434  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.500   1.351   0.709  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.712   1.617   1.938  1.00  0.00           C  
HETATM   15  C15 UNL     1      -0.732   0.563   2.267  1.00  0.00           C  
HETATM   16  C16 UNL     1       0.418   0.311   1.420  1.00  0.00           C  
HETATM   17  C17 UNL     1       0.313  -0.052  -0.003  1.00  0.00           C  
HETATM   18  C18 UNL     1       1.740  -0.363  -0.460  1.00  0.00           C  
HETATM   19  O1  UNL     1       2.143  -1.541  -0.428  1.00  0.00           O  
HETATM   20  O2  UNL     1       2.570   0.612  -0.896  1.00  0.00           O  
HETATM   21  C19 UNL     1       3.880   0.528  -1.343  1.00  0.00           C  
HETATM   22  C20 UNL     1       4.893   0.016  -0.370  1.00  0.00           C  
HETATM   23  O3  UNL     1       4.645  -1.272   0.079  1.00  0.00           O  
HETATM   24  C21 UNL     1       6.239  -0.064  -1.110  1.00  0.00           C  
HETATM   25  O4  UNL     1       6.514   1.205  -1.555  1.00  0.00           O  
HETATM   26  P1  UNL     1       7.955   1.346  -2.415  1.00  0.00           P  
HETATM   27  O5  UNL     1       7.985   2.768  -2.958  1.00  0.00           O  
HETATM   28  O6  UNL     1       8.012   0.237  -3.714  1.00  0.00           O1-
HETATM   29  O7  UNL     1       9.281   1.030  -1.441  1.00  0.00           O  
HETATM   30  C22 UNL     1       9.878  -0.177  -1.711  1.00  0.00           C  
HETATM   31  C23 UNL     1      11.078  -0.493  -0.890  1.00  0.00           C  
HETATM   32  N1  UNL     1      10.872  -0.556   0.519  1.00  0.00           N1+
HETATM   33  C24 UNL     1      11.497   0.635   1.116  1.00  0.00           C  
HETATM   34  C25 UNL     1      11.515  -1.717   1.119  1.00  0.00           C  
HETATM   35  C26 UNL     1       9.505  -0.557   0.950  1.00  0.00           C  
HETATM   36  H1  UNL     1     -12.233  -1.651  -1.735  1.00  0.00           H  
HETATM   37  H2  UNL     1     -13.259  -1.796  -0.304  1.00  0.00           H  
HETATM   38  H3  UNL     1     -12.008  -3.049  -0.580  1.00  0.00           H  
HETATM   39  H4  UNL     1     -11.758  -0.567   0.893  1.00  0.00           H  
HETATM   40  H5  UNL     1     -10.564  -1.876   0.757  1.00  0.00           H  
HETATM   41  H6  UNL     1     -10.940   0.475  -1.184  1.00  0.00           H  
HETATM   42  H7  UNL     1      -9.640   0.195  -0.004  1.00  0.00           H  
HETATM   43  H8  UNL     1      -9.109  -0.337  -2.391  1.00  0.00           H  
HETATM   44  H9  UNL     1     -10.301  -1.636  -2.378  1.00  0.00           H  
HETATM   45  H10 UNL     1      -8.100  -2.572  -1.943  1.00  0.00           H  
HETATM   46  H11 UNL     1      -9.306  -2.802  -0.561  1.00  0.00           H  
HETATM   47  H12 UNL     1      -8.161  -1.023   0.686  1.00  0.00           H  
HETATM   48  H13 UNL     1      -7.001  -2.329   0.145  1.00  0.00           H  
HETATM   49  H14 UNL     1      -7.428   0.267  -1.459  1.00  0.00           H  
HETATM   50  H15 UNL     1      -6.374  -1.119  -1.822  1.00  0.00           H  
HETATM   51  H16 UNL     1      -5.103   0.642  -0.833  1.00  0.00           H  
HETATM   52  H17 UNL     1      -5.052  -0.728   0.267  1.00  0.00           H  
HETATM   53  H18 UNL     1      -7.135   1.509   0.633  1.00  0.00           H  
HETATM   54  H19 UNL     1      -6.893   0.068   1.612  1.00  0.00           H  
HETATM   55  H20 UNL     1      -6.076   1.996   2.742  1.00  0.00           H  
HETATM   56  H21 UNL     1      -4.840   0.767   2.554  1.00  0.00           H  
HETATM   57  H22 UNL     1      -5.238   3.449   1.087  1.00  0.00           H  
HETATM   58  H23 UNL     1      -4.105   3.149   2.395  1.00  0.00           H  
HETATM   59  H24 UNL     1      -3.901   2.482  -0.585  1.00  0.00           H  
HETATM   60  H25 UNL     1      -2.870   3.397   0.486  1.00  0.00           H  
HETATM   61  H26 UNL     1      -2.977   0.350   0.778  1.00  0.00           H  
HETATM   62  H27 UNL     1      -1.871   1.330  -0.177  1.00  0.00           H  
HETATM   63  H28 UNL     1      -2.464   1.768   2.771  1.00  0.00           H  
HETATM   64  H29 UNL     1      -1.201   2.624   1.870  1.00  0.00           H  
HETATM   65  H30 UNL     1      -1.257  -0.443   2.426  1.00  0.00           H  
HETATM   66  H31 UNL     1      -0.334   0.821   3.307  1.00  0.00           H  
HETATM   67  H32 UNL     1       1.112   1.222   1.457  1.00  0.00           H  
HETATM   68  H33 UNL     1       1.087  -0.479   1.896  1.00  0.00           H  
HETATM   69  H34 UNL     1       0.113   0.889  -0.614  1.00  0.00           H  
HETATM   70  H35 UNL     1      -0.368  -0.867  -0.268  1.00  0.00           H  
HETATM   71  H36 UNL     1       4.191   1.579  -1.621  1.00  0.00           H  
HETATM   72  H37 UNL     1       3.977  -0.026  -2.315  1.00  0.00           H  
HETATM   73  H38 UNL     1       5.071   0.721   0.469  1.00  0.00           H  
HETATM   74  H39 UNL     1       5.140  -1.939  -0.426  1.00  0.00           H  
HETATM   75  H40 UNL     1       6.110  -0.798  -1.957  1.00  0.00           H  
HETATM   76  H41 UNL     1       6.980  -0.473  -0.425  1.00  0.00           H  
HETATM   77  H42 UNL     1       9.137  -1.030  -1.708  1.00  0.00           H  
HETATM   78  H43 UNL     1      10.223  -0.134  -2.783  1.00  0.00           H  
HETATM   79  H44 UNL     1      11.874   0.243  -1.146  1.00  0.00           H  
HETATM   80  H45 UNL     1      11.472  -1.477  -1.237  1.00  0.00           H  
HETATM   81  H46 UNL     1      10.733   1.445   1.032  1.00  0.00           H  
HETATM   82  H47 UNL     1      12.365   0.918   0.457  1.00  0.00           H  
HETATM   83  H48 UNL     1      11.789   0.457   2.159  1.00  0.00           H  
HETATM   84  H49 UNL     1      12.099  -2.294   0.366  1.00  0.00           H  
HETATM   85  H50 UNL     1      10.766  -2.424   1.531  1.00  0.00           H  
HETATM   86  H51 UNL     1      12.167  -1.423   1.966  1.00  0.00           H  
HETATM   87  H52 UNL     1       8.985   0.393   0.793  1.00  0.00           H  
HETATM   88  H53 UNL     1       9.532  -0.717   2.067  1.00  0.00           H  
HETATM   89  H54 UNL     1       8.958  -1.434   0.545  1.00  0.00           H  
CONECT    1    2   36   37   38
CONECT    2    3   39   40
CONECT    3    4   41   42
CONECT    4    5   43   44
CONECT    5    6   45   46
CONECT    6    7   47   48
CONECT    7    8   49   50
CONECT    8    9   51   52
CONECT    9   10   53   54
CONECT   10   11   55   56
CONECT   11   12   57   58
CONECT   12   13   59   60
CONECT   13   14   61   62
CONECT   14   15   63   64
CONECT   15   16   65   66
CONECT   16   17   67   68
CONECT   17   18   69   70
CONECT   18   19   19   20
CONECT   20   21
CONECT   21   22   71   72
CONECT   22   23   24   73
CONECT   23   74
CONECT   24   25   75   76
CONECT   25   26
CONECT   26   27   27   28   29
CONECT   29   30
CONECT   30   31   77   78
CONECT   31   32   79   80
CONECT   32   33   34   35
CONECT   33   81   82   83
CONECT   34   84   85   86
CONECT   35   87   88   89
END

HMDB0010384
     RDKit          3D
LysoPC(18:0/0:0)
 89 88  0  0  0  0  0  0  0  0999 V2000
  -12.2317   -1.9658   -0.6617 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2145   -1.2262    0.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3518   -0.3038   -0.6666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5805   -1.0610   -1.7263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6762   -2.0920   -1.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6387   -1.4942   -0.1761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8231   -0.5401   -0.9656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7172    0.0898   -0.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3098    0.8433    1.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3924    1.5413    1.9392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5344    2.6353    1.4860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5279    2.4371    0.4341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5000    1.3509    0.7094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7123    1.6166    1.9380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7324    0.5632    2.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4183    0.3106    1.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3126   -0.0520   -0.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7398   -0.3632   -0.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1432   -1.5409   -0.4275 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5701    0.6115   -0.8962 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8800    0.5281   -1.3428 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8933    0.0162   -0.3703 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6451   -1.2719    0.0794 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2392   -0.0645   -1.1103 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5138    1.2047   -1.5551 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9547    1.3458   -2.4148 P   0  0  0  0  0  5  0  0  0  0  0  0
    7.9849    2.7681   -2.9578 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0118    0.2368   -3.7140 O   0  0  0  0  0  1  0  0  0  0  0  0
    9.2815    1.0305   -1.4405 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8783   -0.1772   -1.7110 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0779   -0.4931   -0.8898 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8723   -0.5558    0.5185 N   0  0  0  0  0  4  0  0  0  0  0  0
   11.4966    0.6349    1.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5150   -1.7174    1.1189 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5054   -0.5572    0.9496 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2329   -1.6511   -1.7350 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.2594   -1.7964   -0.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0079   -3.0487   -0.5803 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7582   -0.5668    0.8930 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5643   -1.8760    0.7572 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9403    0.4753   -1.1841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6405    0.1954   -0.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1094   -0.3373   -2.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3012   -1.6363   -2.3785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0996   -2.5721   -1.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3061   -2.8023   -0.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1606   -1.0229    0.6856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0010   -2.3288    0.1448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4282    0.2674   -1.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3743   -1.1187   -1.8223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1028    0.6418   -0.8326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0521   -0.7280    0.2670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1354    1.5088    0.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8932    0.0677    1.6117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0760    1.9957    2.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8405    0.7674    2.5538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2384    3.4486    1.0867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1054    3.1492    2.3952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9012    2.4823   -0.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8696    3.3968    0.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9773    0.3495    0.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8710    1.3302   -0.1768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4639    1.7677    2.7712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2006    2.6242    1.8699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2567   -0.4428    2.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3345    0.8206    3.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1119    1.2222    1.4568 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0868   -0.4788    1.8956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1126    0.8893   -0.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3680   -0.8671   -0.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1905    1.5791   -1.6212 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9772   -0.0261   -2.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0710    0.7208    0.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1399   -1.9387   -0.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1100   -0.7985   -1.9573 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9800   -0.4729   -0.4254 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1371   -1.0303   -1.7080 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2226   -0.1337   -2.7827 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8739    0.2426   -1.1464 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4724   -1.4775   -1.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7330    1.4454    1.0325 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3651    0.9177    0.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7891    0.4568    2.1590 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0986   -2.2935    0.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7660   -2.4240    1.5312 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1669   -1.4234    1.9665 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9852    0.3925    0.7927 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5316   -0.7166    2.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9581   -1.4337    0.5453 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  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 26 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 32 34  1  0
 32 35  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  0
  2 40  1  0
  3 41  1  0
  3 42  1  0
  4 43  1  0
  4 44  1  0
  5 45  1  0
  5 46  1  0
  6 47  1  0
  6 48  1  0
  7 49  1  0
  7 50  1  0
  8 51  1  0
  8 52  1  0
  9 53  1  0
  9 54  1  0
 10 55  1  0
 10 56  1  0
 11 57  1  0
 11 58  1  0
 12 59  1  0
 12 60  1  0
 13 61  1  0
 13 62  1  0
 14 63  1  0
 14 64  1  0
 15 65  1  0
 15 66  1  0
 16 67  1  0
 16 68  1  0
 17 69  1  0
 17 70  1  0
 21 71  1  0
 21 72  1  0
 22 73  1  1
 23 74  1  0
 24 75  1  0
 24 76  1  0
 30 77  1  0
 30 78  1  0
 31 79  1  0
 31 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
 35 87  1  0
 35 88  1  0
 35 89  1  0
M  CHG  2  28  -1  32   1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2R)-2-Hydroxy-3-(stearoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate	ChEBI
1-O-Stearoyl-sn-glycero-3-phosphocholine	ChEBI
1-Octadecanoyl-sn-glycero-3-phosphocholine	ChEBI
1-Stearoyl-glycero-3-phosphocholine	ChEBI
1-Stearoylglycerophosphocholine (18:0)	ChEBI
1-Stearoylglycerophosphocholine(18:0)	ChEBI
18:0 LYSO-PC	ChEBI
GPCho 18:0/0:0	ChEBI
GPCho(18:0/0:0)	ChEBI
LPC 18:0/0:0	ChEBI
LPC(18:0)	ChEBI
LPC(18:0/0:0)	ChEBI
LysoPC 18:0/0:0	ChEBI
LysoPC(18:0)	ChEBI
Lysophosphatidylcholine (18:0/0:0)	ChEBI
Lysophosphatidylcholine(18:0)	ChEBI
Lysophosphatidylcholine(18:0/0:0)	ChEBI
PC 18:0/0:0	ChEBI
PC(18:0/0:0)	ChEBI
(2R)-2-Hydroxy-3-(stearoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphoric acid	Generator
LyPC(18:0)	HMDB
LyPC(18:0/0:0)	HMDB
LysoPC a C18:0	HMDB
Stearoyl alpha-lysolecithin	HMDB
Stearoyllysophosphatidylcholine	HMDB
1-Octadecyl-glycero-3-phosphocholine	HMDB
1-Stearoyl-sn-glycero-3-phosphorylcholine	HMDB
Stearoyl L-alpha-lysolecithin	HMDB
1-Stearoyl-2-hydroxy-sn-glycero-3-phosphocholine	HMDB
Stearoyl alpha-lysolecithin, (+-)-isomer	HMDB
Stearoyl alpha-lysolecithin, (R)-isomer	HMDB
1-Octadecanoyl-glycero-3-phosphocholine	HMDB
1-Octadecanoylglycerophosphocholine	HMDB
1-Octadecylglycerophosphocholine	HMDB
1-Stearoylglycerophosphocholine	HMDB
1-O-Stearoyl-2-lyso-sn-glycero-3-phosphocholine	HMDB
1-Octadecanoyl-3-glycerophosphorylcholine	HMDB
1-Octadecanoyl-sn-glycerol-3-phosphorylcholine	HMDB
1-Octadecanoyllysolecithin	HMDB
1-Stearoyl-2-lysophosphatidylcholine	HMDB
1-Stearoyl-3-glycerylphosphorylcholine	HMDB
1-Stearoyl-GPC	HMDB
1-Stearoyl-lysophosphatidylcholine	HMDB
1-Stearoyl-sn-glycero-3-phosphocholine	HMDB
1-Stearoyl-sn-glycerol-3-phosphatidylcholine	HMDB
1-Stearoyl-sn-glycerol-3-phosphorylcholine	HMDB
1-Stearoylglycero-3-phosphorylcholine	HMDB
1-Stearoyllysophosphatidylcholine	HMDB
GPC(18:0)	HMDB
GPC(18:0/0:0)	HMDB
Lysophosphatidylcholine C18:0	HMDB
Stearoyl L-α-lysolecithin	HMDB
Stearoyl lysolecithin	HMDB
Stearoyl lysophosphatidylcholine	HMDB
LysoPC(18:0/0:0)	Lipid Annotator, ChEBI

Chemical Formula

C₂₆H₅₄NO₇P

Average Molecular Weight

523.6832

Monoisotopic Molecular Weight

523.363789599

IUPAC Name

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

Traditional Name

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

CAS Registry Number

19420-57-6

SMILES

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

InChI Identifier

InChI=1S/C26H54NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26(29)32-23-25(28)24-34-35(30,31)33-22-21-27(2,3)4/h25,28H,5-24H2,1-4H3/t25-/m1/s1

InChI Key

IHNKQIMGVNPMTC-RUZDIDTESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphocholine.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphocholines

Direct Parent

1-acyl-sn-glycero-3-phosphocholines

Alternative Parents

Substituents

1-acyl-sn-glycero-3-phosphocholine
Phosphocholine
Fatty acid ester
Dialkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Tetraalkylammonium salt
Quaternary ammonium salt
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Alcohol
Organic oxygen compound
Organopnictogen compound
Carbonyl group
Organic salt
Amine
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

1-O-acyl-sn-glycero-3-phosphocholine (CHEBI:73858 )
lysophosphatidylcholine 18:0 (CHEBI:73858 )
Monoacylglycerophosphocholines (LMGP01050026 )

Ontology

Physiological effect

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 18953024)
Cerebrospinal Fluid (CSF) (PMID: 22546835)
Saliva (HMDB: HMDB0010384)
Cerebrospinal fluid (HMDB: HMDB0010384)

Tissue

All Tissues (HMDB: HMDB0010384)
All Tissues (HMDB: HMDB0010384)

Cellular substructure

Membrane (HMDB: HMDB0010384)
Extracellular (HMDB: HMDB0010384)
Cell membrane (PMID: 30845751)
Cell membrane (HMDB: HMDB0010384)
Intracellular membrane (HMDB: HMDB0010384)

Organ

Placenta (HMDB: HMDB0010384)

Excreta

Biofluid or Excreta

Urine (PMID: 24023812)
Feces (PMID: 21458633)

Cell

All cells and tissues (HMDB: HMDB0010384)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0010384)

Source

Endogenous

Endogenous (HMDB: HMDB0010384)

Animal

Animal (HMDB: HMDB0010384)

Exogenous

Food

Food (HMDB: HMDB0010384)

Animal origin

Poultry

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)
Cow milk, pasteurized, vitamin A + D added, 0% fat (FooDB: FOOD00889)
Cow milk, pasteurized, vitamin A + D added, 1% fat (FooDB: FOOD00890)
Cow milk, pasteurized, vitamin A + D added, 2% fat (FooDB: FOOD00891)
Cow milk, pasteurized, vitamin D added, 3.25% fat (FooDB: FOOD00892)

Exogenous (HMDB: HMDB0010384)

Process

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	0.00023 g/L	ALOGPS
logP	2.53	ALOGPS
logP	2.08	ChemAxon
logS	-6.4	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	26	ChemAxon
Refractivity	151.48 m³·mol⁻¹	ChemAxon
Polarizability	61.71 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]+	244.216	30932474
DeepCCS	[M-H]-	241.108	30932474
DeepCCS	[M-2H]-	275.207	30932474
DeepCCS	[M+Na]+	251.713	30932474
AllCCS	[M+H]+	240.9	32859911
AllCCS	[M+H-H2O]+	239.7	32859911
AllCCS	[M+NH4]+	242.0	32859911
AllCCS	[M+Na]+	242.3	32859911
AllCCS	[M-H]-	234.9	32859911
AllCCS	[M+Na-2H]-	237.4	32859911
AllCCS	[M+HCOO]-	240.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
LysoPC(18:0/0:0)	CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C	3572.4	Standard polar	33892256
LysoPC(18:0/0:0)	CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C	3229.1	Standard non polar	33892256
LysoPC(18:0/0:0)	CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C	3538.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
LysoPC(18:0/0:0),1TMS,isomer #1	CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O[Si](C)(C)C	3499.9	Semi standard non polar	33892256
LysoPC(18:0/0:0),1TBDMS,isomer #1	CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C	3741.4	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(18:0/0:0) GC-MS (1 TMS) - 70eV, Positive	splash10-024u-9321010000-7c4db1d8f50345253e5e	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(18:0/0:0) 40V, Positive-QTOF	splash10-0f89-1900000000-4587eca1f40127997f9a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - LysoPC(18:0/0:0) 10V, Positive-QTOF	splash10-00di-0000090000-8c56fcd29df2d9fc9c2b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - LysoPC(18:0/0:0) 20V, Positive-QTOF	splash10-00di-0200090000-3a51011c95929ab98d63	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(18:0/0:0) 10V, Positive-QTOF	splash10-0002-0000190000-41c73cffe2f1aaf160f3	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(18:0/0:0) 20V, Positive-QTOF	splash10-000j-0001960000-94fcb8b8814d186b45b2	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(18:0/0:0) 40V, Positive-QTOF	splash10-0gw0-1609710000-ae76bfe8f474291dc445	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(18:0/0:0) 10V, Negative-QTOF	splash10-00di-0030090000-f659985c9cbbaf332a78	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(18:0/0:0) 20V, Negative-QTOF	splash10-001i-0090010000-01d93fd13edb0afa2e7a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(18:0/0:0) 40V, Negative-QTOF	splash10-001i-0090000000-ca0fc5a9d32fa941ad45	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(18:0/0:0) 10V, Negative-QTOF	splash10-0a4i-0000090000-3069bae6fba637487e2d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(18:0/0:0) 20V, Negative-QTOF	splash10-053r-0090070000-1397c10d116d343edd9e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(18:0/0:0) 40V, Negative-QTOF	splash10-001i-0090020000-274c1e62706a1695b7b9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(18:0/0:0) 10V, Positive-QTOF	splash10-05fr-0000090000-0d83963fc8d256300785	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(18:0/0:0) 20V, Positive-QTOF	splash10-0089-0900060000-23beae7a997640f05765	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(18:0/0:0) 40V, Positive-QTOF	splash10-0kai-0910040000-b24aadea134c86d41382	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(18:0/0:0) 10V, Positive-QTOF	splash10-001i-0000190000-db2c4daf832d5e722111	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(18:0/0:0) 20V, Positive-QTOF	splash10-00f0-0002990000-f2b5b69d9cc9121b1dc6	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(18:0/0:0) 40V, Positive-QTOF	splash10-0fdp-0309400000-f08bc6aa7b631fbc521e	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva
Urine

Tissue Locations

All Tissues
Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	48.5 +/- 20.2 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22800120	details
Blood	Detected and Quantified	47.54 +/- 8.38 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	9.10-54.0 uM	Adult (>18 years old)	Both	Normal	Molecular You	details
Blood	Detected and Quantified	47.536 +/- 8.381 uM	Adult (>18 years old)	Both	Normal	18953024	details
Blood	Detected and Quantified	14.4 (12-17.7) uM	Newborn (0-30 days old)	Not Available	Normal	25754623	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22257447	details
Blood	Detected and Quantified	26.22(5.93) uM	Adult (>18 years old)	Both	Normal	26010610	details
Blood	Detected and Quantified	21.8 +/- 4.97 uM	Adult (>18 years old)	Both	Normal	28278231	details
Blood	Detected and Quantified	24.5 (18.5-31.9) uM	Infant (0-1 year old)	Not Available	Normal	25754623	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.069 +/- 0.019 uM	Adult (>18 years old)	Not Specified	Normal	22546835	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	21458633	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	23384618	details
Feces	Detected and Quantified	3.29 +/- 2.64 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected and Quantified	3.28 +/- 3.9 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Saliva	Detected and Quantified	0.108 +/- 0.018 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Urine	Detected and Quantified	5.02 +/- 0.24 umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	26910390	details
Urine	Detected and Quantified	0.0040 (0.0013 - 0.0100) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	0.0248 +/- 0.0131 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	0.0-0.07 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	32340350	details
Urine	Detected and Quantified	0.02(0.0-0.07) umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	32340350	details
Urine	Detected and Quantified	0.01(0.0-0.03) umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	32340350	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Schizophrenia	22800120	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Schizophrenia	22257447	details
Blood	Detected and Quantified	21.6(5.06) uM	Adult (>18 years old)	Both	Heart failure with preserved ejection fraction	26010610	details
Blood	Detected and Quantified	19.323 (17.977) uM	Adult (>18 years old)	Female	Pregnancy with fetus having congenital heart defect	24704061	details
Blood	Detected and Quantified	36.487 (11.673) uM	Adult (>18 years old)	Female	Pregnancy	24704061	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Liver cirrhosis	21458633	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	hepatocellular carcinoma	21458633	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	liver cirrhosis	23384618	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Newborn (0-30 days old)	Not Specified	Premature neonates	23210743	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Urine	Detected and Quantified	6.07 +/- 0.35 umol/mmol creatinine	Adolescent (13-18 years old)	Both	Obese	26910390	details
Urine	Detected and Quantified	0.0202 +/- 0.0112 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	0.0259 +/- 0.0362 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Analysis of 30 no...	details

Associated Disorders and Diseases

Disease References

Schizophrenia
Cai HL, Li HD, Yan XZ, Sun B, Zhang Q, Yan M, Zhang WY, Jiang P, Zhu RH, Liu YP, Fang PF, Xu P, Yuan HY, Zhang XH, Hu L, Yang W, Ye HS: Metabolomic analysis of biochemical changes in the plasma and urine of first-episode neuroleptic-naive schizophrenia patients after treatment with risperidone. J Proteome Res. 2012 Aug 3;11(8):4338-50. doi: 10.1021/pr300459d. Epub 2012 Jul 26. [PubMed:22800120 ] Oresic M, Seppanen-Laakso T, Sun D, Tang J, Therman S, Viehman R, Mustonen U, van Erp TG, Hyotylainen T, Thompson P, Toga AW, Huttunen MO, Suvisaari J, Kaprio J, Lonnqvist J, Cannon TD: Phospholipids and insulin resistance in psychosis: a lipidomics study of twin pairs discordant for schizophrenia. Genome Med. 2012 Jan 18;4(1):1. doi: 10.1186/gm300. [PubMed:22257447 ]
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 ]
Cirrhosis
Cao H, Huang H, Xu W, Chen D, Yu J, Li J, Li L: Fecal metabolome profiling of liver cirrhosis and hepatocellular carcinoma patients by ultra performance liquid chromatography-mass spectrometry. Anal Chim Acta. 2011 Apr 8;691(1-2):68-75. doi: 10.1016/j.aca.2011.02.038. Epub 2011 Feb 23. [PubMed:21458633 ] Huang HJ, Zhang AY, Cao HC, Lu HF, Wang BH, Xie Q, Xu W, Li LJ: Metabolomic analyses of faeces reveals malabsorption in cirrhotic patients. Dig Liver Dis. 2013 Aug;45(8):677-82. doi: 10.1016/j.dld.2013.01.001. Epub 2013 Feb 4. [PubMed:23384618 ]
Hepatocellular carcinoma
Cao H, Huang H, Xu W, Chen D, Yu J, Li J, Li L: Fecal metabolome profiling of liver cirrhosis and hepatocellular carcinoma patients by ultra performance liquid chromatography-mass spectrometry. Anal Chim Acta. 2011 Apr 8;691(1-2):68-75. doi: 10.1016/j.aca.2011.02.038. Epub 2011 Feb 23. [PubMed:21458633 ]
Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Obesity
Cho K, Moon JS, Kang JH, Jang HB, Lee HJ, Park SI, Yu KS, Cho JY: Combined untargeted and targeted metabolomic profiling reveals urinary biomarkers for discriminating obese from normal-weight adolescents. Pediatr Obes. 2017 Apr;12(2):93-101. doi: 10.1111/ijpo.12114. Epub 2016 Feb 22. [PubMed:26910390 ]

Associated OMIM IDs

181500 (Schizophrenia)
114550 (Hepatocellular carcinoma)
114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)
601665 (Obesity)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB027535

KNApSAcK ID

Not Available

Chemspider ID

435389

KEGG Compound ID

C04230

BioCyc ID

CPD-8345

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

497299

PDB ID

Not Available

ChEBI ID

73858

Food Biomarker Ontology

Not Available

VMH ID

PCHOLSTE_HS

MarkerDB ID

MDB00000791

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
Wernly B, Lichtenauer M, Hoppe UC, Jung C: Hyperglycemia in septic patients: an essential stress survival response in all, a robust marker for risk stratification in some, to be messed with in none. J Thorac Dis. 2016 Jul;8(7):E621-4. doi: 10.21037/jtd.2016.05.24. [PubMed:27501420 ]
Knuplez E, Marsche G: An Updated Review of Pro- and Anti-Inflammatory Properties of Plasma Lysophosphatidylcholines in the Vascular System. Int J Mol Sci. 2020 Jun 24;21(12). pii: ijms21124501. doi: 10.3390/ijms21124501. [PubMed:32599910 ]
Sun JK, Sun F, Wang X, Yuan ST, Zheng SY, Mu XW: Risk factors and prognosis of hypoalbuminemia in surgical septic patients. PeerJ. 2015 Oct 1;3:e1267. doi: 10.7717/peerj.1267. eCollection 2015. [PubMed:26557421 ]

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(18:0/0:0) (HMDB0010384)

MOL for HMDB0010384 (LysoPC(18:0/0:0))

3D MOL for HMDB0010384 (LysoPC(18:0/0:0))

3D SDF for HMDB0010384 (LysoPC(18:0/0:0))

3D-SDF for HMDB0010384 (LysoPC(18:0/0:0))

PDB for HMDB0010384 (LysoPC(18:0/0:0))

3D PDB for HMDB0010384 (LysoPC(18:0/0:0))

SMILES for HMDB0010384 (LysoPC(18:0/0:0))

INCHI for HMDB0010384 (LysoPC(18:0/0:0))

Structure for HMDB0010384 (LysoPC(18:0/0:0))

3D Structure for HMDB0010384 (LysoPC(18:0/0:0))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes