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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 15:12:12 UTC

Update Date

2023-07-07 20:53:58 UTC

HMDB ID

HMDB0002815

Secondary Accession Numbers

HMDB02815

Metabolite Identification

Common Name

LysoPC(18:1/0:0)

Description

LysoPC(18:1(9Z)) 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(18:19Z)), in particular, consists of one chain of oleic acid at the C-1 position. The oleic acid moiety, an omega-9 fatty acid, is derived from various animal and vegetable sources such as olive oil, acai and grapeseed 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(18:1(9Z)/0:0)
  Mrv1652303192020112D          

 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
  -11.0501    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7642    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4784    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1925    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.9066    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.6207    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.3348    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.0490    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.7631    0.7695    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  2  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

HMDB0002815
     RDKit          3D
LysoPC(18:1(9Z)/0:0)
 87 86  0  0  0  0  0  0  0  0999 V2000
  -10.1460    1.5777   -1.3971 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3889    0.4922   -0.3229 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8123    1.1195    0.9584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9099    2.0411    1.6260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7209    1.6879    2.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6495    0.7873    1.9006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0141   -0.6502    1.9761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9007   -1.5519    1.4255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6454   -1.2192    0.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4786   -0.7953   -0.4060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3233   -0.6044    0.4563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1382   -1.4745    0.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0150   -1.1754    1.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7790   -1.9906    0.7070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2643   -1.7055   -0.6886 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1117   -0.2800   -0.8879 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5965   -0.0316   -2.2829 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8233   -0.8262   -2.6055 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2017   -0.8049   -3.8265 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5440   -1.5469   -1.7189 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6747   -2.2859   -1.9209 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8554   -1.4456   -2.3076 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6395   -0.7808   -3.4716 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9993   -0.3922   -1.1931 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0971    0.3875   -1.5822 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3244    1.5707   -0.4015 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.1554    1.6108    0.5497 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4412    3.1114   -1.1163 O   0  0  0  0  0  1  0  0  0  0  0  0
    7.7356    1.2548    0.4786 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4605    0.2144   -0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7138   -0.1022    0.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6508    0.9714    0.7478 N   0  0  0  0  0  4  0  0  0  0  0  0
   10.4284    2.0362   -0.2117 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6990    1.5212    2.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9788    0.4294    0.4647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9010    1.0161   -2.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2700    2.1815   -1.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0577    2.1462   -1.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2032   -0.1734   -0.7407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4854   -0.0923   -0.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1101    0.2457    1.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8304    1.6089    0.7696 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5666    2.6547    2.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5985    2.8947    0.8937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1167    1.2883    3.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2254    2.6652    2.7627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6585    1.0028    2.3761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4699    1.0109    0.8001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9499   -0.9531    1.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0921   -0.9510    3.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4141   -2.5734    1.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0365   -1.6016    2.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4938   -1.3457   -0.7143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3991   -0.5746   -1.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9364    0.4562    0.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4850   -0.6058    1.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3548   -2.5407    0.0840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7777   -1.2155   -0.9554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8392   -0.1004    1.0683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3555   -1.5103    2.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0630   -3.0529    0.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0005   -1.6920    1.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9826   -2.0544   -1.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6314   -2.3396   -0.8048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7142    0.4326   -0.6849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9241    0.0410   -0.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2066   -0.2515   -3.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9052    1.0497   -2.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9456   -2.9277   -1.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4957   -3.0323   -2.7443 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7894   -2.0635   -2.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -0.3619   -3.8809 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0812    0.2009   -1.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1522   -0.8889   -0.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6605    0.3632   -1.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7979   -0.6798   -0.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1639   -1.0094    0.1452 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4303   -0.4496    1.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2333    1.6592   -1.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3569    2.6536   -0.2817 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6262    2.7052    0.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8084    1.2559    2.6808 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7715    2.6242    2.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5751    1.1518    2.6723 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.7637    1.0046    0.9965 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1074    0.4794   -0.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0156   -0.6153    0.8436 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  2  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
 10 54  1  0
 11 55  1  0
 11 56  1  0
 12 57  1  0
 12 58  1  0
 13 59  1  0
 13 60  1  0
 14 61  1  0
 14 62  1  0
 15 63  1  0
 15 64  1  0
 16 65  1  0
 16 66  1  0
 17 67  1  0
 17 68  1  0
 21 69  1  0
 21 70  1  0
 22 71  1  6
 23 72  1  0
 24 73  1  0
 24 74  1  0
 30 75  1  0
 30 76  1  0
 31 77  1  0
 31 78  1  0
 33 79  1  0
 33 80  1  0
 33 81  1  0
 34 82  1  0
 34 83  1  0
 34 84  1  0
 35 85  1  0
 35 86  1  0
 35 87  1  0
M  CHG  2  28  -1  32   1
M  END

PC(18:1(9Z)/0:0)
  Mrv1652303192020112D          

 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
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   -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
  -11.0501    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7642    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4784    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1925    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.9066    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.6207    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.3348    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.0490    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.7631    0.7695    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  2  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>
HMDB0002815

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C26H52NO7P/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/h12-13,25,28H,5-11,14-24H2,1-4H3/b13-12-/t25-/m1/s1

> <INCHI_KEY>
YAMUFBLWGFFICM-PTGWMXDISA-N

> <FORMULA>
C26H52NO7P

> <MOLECULAR_WEIGHT>
521.6673

> <EXACT_MASS>
521.348139535

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
60.018295646263375

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{[(2R)-2-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

> <ALOGPS_LOGP>
2.38

> <JCHEM_LOGP>
1.719958150194922

> <ALOGPS_LOGS>
-6.32

> <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>
152.59230000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
25

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.76e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-{[(2R)-2-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002815
     RDKit          3D
LysoPC(18:1(9Z)/0:0)
 87 86  0  0  0  0  0  0  0  0999 V2000
  -10.1460    1.5777   -1.3971 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3889    0.4922   -0.3229 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8123    1.1195    0.9584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9099    2.0411    1.6260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7209    1.6879    2.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6495    0.7873    1.9006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0141   -0.6502    1.9761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9007   -1.5519    1.4255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6454   -1.2192    0.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4786   -0.7953   -0.4060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3233   -0.6044    0.4563 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0150   -1.1754    1.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2643   -1.7055   -0.6886 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6747   -2.2859   -1.9209 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8554   -1.4456   -2.3076 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6395   -0.7808   -3.4716 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.3244    1.5707   -0.4015 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.1554    1.6108    0.5497 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4412    3.1114   -1.1163 O   0  0  0  0  0  1  0  0  0  0  0  0
    7.7356    1.2548    0.4786 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4605    0.2144   -0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7138   -0.1022    0.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6508    0.9714    0.7478 N   0  0  0  0  0  4  0  0  0  0  0  0
   10.4284    2.0362   -0.2117 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.9010    1.0161   -2.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
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  -11.2032   -0.1734   -0.7407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4854   -0.0923   -0.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1101    0.2457    1.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8304    1.6089    0.7696 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5666    2.6547    2.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5985    2.8947    0.8937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1167    1.2883    3.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2254    2.6652    2.7627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6585    1.0028    2.3761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4699    1.0109    0.8001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9499   -0.9531    1.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0921   -0.9510    3.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4141   -2.5734    1.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0365   -1.6016    2.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4938   -1.3457   -0.7143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3991   -0.5746   -1.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9364    0.4562    0.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4850   -0.6058    1.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3548   -2.5407    0.0840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7777   -1.2155   -0.9554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8392   -0.1004    1.0683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3555   -1.5103    2.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0630   -3.0529    0.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0005   -1.6920    1.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9826   -2.0544   -1.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6314   -2.3396   -0.8048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7142    0.4326   -0.6849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9241    0.0410   -0.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2066   -0.2515   -3.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9052    1.0497   -2.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9456   -2.9277   -1.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4957   -3.0323   -2.7443 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7894   -2.0635   -2.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -0.3619   -3.8809 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0812    0.2009   -1.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1522   -0.8889   -0.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6605    0.3632   -1.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7979   -0.6798   -0.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1639   -1.0094    0.1452 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4303   -0.4496    1.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2333    1.6592   -1.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3569    2.6536   -0.2817 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6262    2.7052    0.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8084    1.2559    2.6808 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7715    2.6242    2.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5751    1.1518    2.6723 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.7637    1.0046    0.9965 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1074    0.4794   -0.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0156   -0.6153    0.8436 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  2  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
 10 54  1  0
 11 55  1  0
 11 56  1  0
 12 57  1  0
 12 58  1  0
 13 59  1  0
 13 60  1  0
 14 61  1  0
 14 62  1  0
 15 63  1  0
 15 64  1  0
 16 65  1  0
 16 66  1  0
 17 67  1  0
 17 68  1  0
 21 69  1  0
 21 70  1  0
 22 71  1  6
 23 72  1  0
 24 73  1  0
 24 74  1  0
 30 75  1  0
 30 76  1  0
 31 77  1  0
 31 78  1  0
 33 79  1  0
 33 80  1  0
 33 81  1  0
 34 82  1  0
 34 83  1  0
 34 84  1  0
 35 85  1  0
 35 86  1  0
 35 87  1  0
M  CHG  2  28  -1  32   1
M  END

HEADER    PROTEIN                                 19-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: PC(18:1(9Z)/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     -20.627   1.436   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -21.960   0.665   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -23.293   1.436   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -24.626   0.665   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -25.959   1.436   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -27.292   0.665   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -28.625   1.436   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -29.958   0.665   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -31.291   1.436   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    HMDB0002815
HETATM    1  C1  UNL     1     -10.146   1.578  -1.397  1.00  0.00           C  
HETATM    2  C2  UNL     1     -10.389   0.492  -0.323  1.00  0.00           C  
HETATM    3  C3  UNL     1     -10.812   1.120   0.958  1.00  0.00           C  
HETATM    4  C4  UNL     1      -9.910   2.041   1.626  1.00  0.00           C  
HETATM    5  C5  UNL     1      -8.721   1.688   2.368  1.00  0.00           C  
HETATM    6  C6  UNL     1      -7.649   0.787   1.901  1.00  0.00           C  
HETATM    7  C7  UNL     1      -8.014  -0.650   1.976  1.00  0.00           C  
HETATM    8  C8  UNL     1      -6.901  -1.552   1.425  1.00  0.00           C  
HETATM    9  C9  UNL     1      -6.645  -1.219   0.009  1.00  0.00           C  
HETATM   10  C10 UNL     1      -5.479  -0.795  -0.406  1.00  0.00           C  
HETATM   11  C11 UNL     1      -4.323  -0.604   0.456  1.00  0.00           C  
HETATM   12  C12 UNL     1      -3.138  -1.474   0.053  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.015  -1.175   1.021  1.00  0.00           C  
HETATM   14  C14 UNL     1      -0.779  -1.991   0.707  1.00  0.00           C  
HETATM   15  C15 UNL     1      -0.264  -1.705  -0.689  1.00  0.00           C  
HETATM   16  C16 UNL     1       0.112  -0.280  -0.888  1.00  0.00           C  
HETATM   17  C17 UNL     1       0.597  -0.032  -2.283  1.00  0.00           C  
HETATM   18  C18 UNL     1       1.823  -0.826  -2.606  1.00  0.00           C  
HETATM   19  O1  UNL     1       2.202  -0.805  -3.827  1.00  0.00           O  
HETATM   20  O2  UNL     1       2.544  -1.547  -1.719  1.00  0.00           O  
HETATM   21  C19 UNL     1       3.675  -2.286  -1.921  1.00  0.00           C  
HETATM   22  C20 UNL     1       4.855  -1.446  -2.308  1.00  0.00           C  
HETATM   23  O3  UNL     1       4.640  -0.781  -3.472  1.00  0.00           O  
HETATM   24  C21 UNL     1       4.999  -0.392  -1.193  1.00  0.00           C  
HETATM   25  O4  UNL     1       6.097   0.388  -1.582  1.00  0.00           O  
HETATM   26  P1  UNL     1       6.324   1.571  -0.402  1.00  0.00           P  
HETATM   27  O5  UNL     1       5.155   1.611   0.550  1.00  0.00           O  
HETATM   28  O6  UNL     1       6.441   3.111  -1.116  1.00  0.00           O1-
HETATM   29  O7  UNL     1       7.736   1.255   0.479  1.00  0.00           O  
HETATM   30  C22 UNL     1       8.461   0.214  -0.101  1.00  0.00           C  
HETATM   31  C23 UNL     1       9.714  -0.102   0.642  1.00  0.00           C  
HETATM   32  N1  UNL     1      10.651   0.971   0.748  1.00  0.00           N1+
HETATM   33  C24 UNL     1      10.428   2.036  -0.212  1.00  0.00           C  
HETATM   34  C25 UNL     1      10.699   1.521   2.087  1.00  0.00           C  
HETATM   35  C26 UNL     1      11.979   0.429   0.465  1.00  0.00           C  
HETATM   36  H1  UNL     1      -9.901   1.016  -2.321  1.00  0.00           H  
HETATM   37  H2  UNL     1      -9.270   2.181  -1.124  1.00  0.00           H  
HETATM   38  H3  UNL     1     -11.058   2.146  -1.604  1.00  0.00           H  
HETATM   39  H4  UNL     1     -11.203  -0.173  -0.741  1.00  0.00           H  
HETATM   40  H5  UNL     1      -9.485  -0.092  -0.330  1.00  0.00           H  
HETATM   41  H6  UNL     1     -11.110   0.246   1.632  1.00  0.00           H  
HETATM   42  H7  UNL     1     -11.830   1.609   0.770  1.00  0.00           H  
HETATM   43  H8  UNL     1     -10.567   2.655   2.382  1.00  0.00           H  
HETATM   44  H9  UNL     1      -9.598   2.895   0.894  1.00  0.00           H  
HETATM   45  H10 UNL     1      -9.117   1.288   3.401  1.00  0.00           H  
HETATM   46  H11 UNL     1      -8.225   2.665   2.763  1.00  0.00           H  
HETATM   47  H12 UNL     1      -6.658   1.003   2.376  1.00  0.00           H  
HETATM   48  H13 UNL     1      -7.470   1.011   0.800  1.00  0.00           H  
HETATM   49  H14 UNL     1      -8.950  -0.953   1.570  1.00  0.00           H  
HETATM   50  H15 UNL     1      -8.092  -0.951   3.090  1.00  0.00           H  
HETATM   51  H16 UNL     1      -7.414  -2.573   1.382  1.00  0.00           H  
HETATM   52  H17 UNL     1      -6.037  -1.602   2.078  1.00  0.00           H  
HETATM   53  H18 UNL     1      -7.494  -1.346  -0.714  1.00  0.00           H  
HETATM   54  H19 UNL     1      -5.399  -0.575  -1.496  1.00  0.00           H  
HETATM   55  H20 UNL     1      -3.936   0.456   0.255  1.00  0.00           H  
HETATM   56  H21 UNL     1      -4.485  -0.606   1.540  1.00  0.00           H  
HETATM   57  H22 UNL     1      -3.355  -2.541   0.084  1.00  0.00           H  
HETATM   58  H23 UNL     1      -2.778  -1.215  -0.955  1.00  0.00           H  
HETATM   59  H24 UNL     1      -1.839  -0.100   1.068  1.00  0.00           H  
HETATM   60  H25 UNL     1      -2.355  -1.510   2.025  1.00  0.00           H  
HETATM   61  H26 UNL     1      -1.063  -3.053   0.743  1.00  0.00           H  
HETATM   62  H27 UNL     1      -0.000  -1.692   1.417  1.00  0.00           H  
HETATM   63  H28 UNL     1      -0.983  -2.054  -1.466  1.00  0.00           H  
HETATM   64  H29 UNL     1       0.631  -2.340  -0.805  1.00  0.00           H  
HETATM   65  H30 UNL     1      -0.714   0.433  -0.685  1.00  0.00           H  
HETATM   66  H31 UNL     1       0.924   0.041  -0.170  1.00  0.00           H  
HETATM   67  H32 UNL     1      -0.207  -0.252  -3.024  1.00  0.00           H  
HETATM   68  H33 UNL     1       0.905   1.050  -2.375  1.00  0.00           H  
HETATM   69  H34 UNL     1       3.946  -2.928  -1.030  1.00  0.00           H  
HETATM   70  H35 UNL     1       3.496  -3.032  -2.744  1.00  0.00           H  
HETATM   71  H36 UNL     1       5.789  -2.064  -2.312  1.00  0.00           H  
HETATM   72  H37 UNL     1       5.414  -0.362  -3.881  1.00  0.00           H  
HETATM   73  H38 UNL     1       4.081   0.201  -1.147  1.00  0.00           H  
HETATM   74  H39 UNL     1       5.152  -0.889  -0.222  1.00  0.00           H  
HETATM   75  H40 UNL     1       8.661   0.363  -1.174  1.00  0.00           H  
HETATM   76  H41 UNL     1       7.798  -0.680  -0.032  1.00  0.00           H  
HETATM   77  H42 UNL     1      10.164  -1.009   0.145  1.00  0.00           H  
HETATM   78  H43 UNL     1       9.430  -0.450   1.657  1.00  0.00           H  
HETATM   79  H44 UNL     1      10.233   1.659  -1.223  1.00  0.00           H  
HETATM   80  H45 UNL     1      11.357   2.654  -0.282  1.00  0.00           H  
HETATM   81  H46 UNL     1       9.626   2.705   0.165  1.00  0.00           H  
HETATM   82  H47 UNL     1       9.808   1.256   2.681  1.00  0.00           H  
HETATM   83  H48 UNL     1      10.772   2.624   2.032  1.00  0.00           H  
HETATM   84  H49 UNL     1      11.575   1.152   2.672  1.00  0.00           H  
HETATM   85  H50 UNL     1      12.764   1.005   0.996  1.00  0.00           H  
HETATM   86  H51 UNL     1      12.107   0.479  -0.636  1.00  0.00           H  
HETATM   87  H52 UNL     1      12.016  -0.615   0.844  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   10   53
CONECT   10   11   54
CONECT   11   12   55   56
CONECT   12   13   57   58
CONECT   13   14   59   60
CONECT   14   15   61   62
CONECT   15   16   63   64
CONECT   16   17   65   66
CONECT   17   18   67   68
CONECT   18   19   19   20
CONECT   20   21
CONECT   21   22   69   70
CONECT   22   23   24   71
CONECT   23   72
CONECT   24   25   73   74
CONECT   25   26
CONECT   26   27   27   28   29
CONECT   29   30
CONECT   30   31   75   76
CONECT   31   32   77   78
CONECT   32   33   34   35
CONECT   33   79   80   81
CONECT   34   82   83   84
CONECT   35   85   86   87
END

HMDB0002815
     RDKit          3D
LysoPC(18:1(9Z)/0:0)
 87 86  0  0  0  0  0  0  0  0999 V2000
  -10.1460    1.5777   -1.3971 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3889    0.4922   -0.3229 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8123    1.1195    0.9584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9099    2.0411    1.6260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7209    1.6879    2.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6495    0.7873    1.9006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0141   -0.6502    1.9761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9007   -1.5519    1.4255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6454   -1.2192    0.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4786   -0.7953   -0.4060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3233   -0.6044    0.4563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1382   -1.4745    0.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0150   -1.1754    1.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7790   -1.9906    0.7070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2643   -1.7055   -0.6886 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1117   -0.2800   -0.8879 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5965   -0.0316   -2.2829 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8233   -0.8262   -2.6055 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2017   -0.8049   -3.8265 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5440   -1.5469   -1.7189 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6747   -2.2859   -1.9209 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8554   -1.4456   -2.3076 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6395   -0.7808   -3.4716 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9993   -0.3922   -1.1931 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0971    0.3875   -1.5822 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3244    1.5707   -0.4015 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.1554    1.6108    0.5497 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4412    3.1114   -1.1163 O   0  0  0  0  0  1  0  0  0  0  0  0
    7.7356    1.2548    0.4786 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4605    0.2144   -0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7138   -0.1022    0.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6508    0.9714    0.7478 N   0  0  0  0  0  4  0  0  0  0  0  0
   10.4284    2.0362   -0.2117 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6990    1.5212    2.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9788    0.4294    0.4647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9010    1.0161   -2.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2700    2.1815   -1.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0577    2.1462   -1.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2032   -0.1734   -0.7407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4854   -0.0923   -0.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1101    0.2457    1.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8304    1.6089    0.7696 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5666    2.6547    2.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5985    2.8947    0.8937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1167    1.2883    3.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2254    2.6652    2.7627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6585    1.0028    2.3761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4699    1.0109    0.8001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9499   -0.9531    1.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0921   -0.9510    3.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4141   -2.5734    1.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0365   -1.6016    2.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4938   -1.3457   -0.7143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3991   -0.5746   -1.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9364    0.4562    0.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4850   -0.6058    1.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3548   -2.5407    0.0840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7777   -1.2155   -0.9554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8392   -0.1004    1.0683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3555   -1.5103    2.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0630   -3.0529    0.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0005   -1.6920    1.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9826   -2.0544   -1.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6314   -2.3396   -0.8048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7142    0.4326   -0.6849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9241    0.0410   -0.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2066   -0.2515   -3.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9052    1.0497   -2.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9456   -2.9277   -1.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4957   -3.0323   -2.7443 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7894   -2.0635   -2.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -0.3619   -3.8809 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0812    0.2009   -1.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1522   -0.8889   -0.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6605    0.3632   -1.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7979   -0.6798   -0.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1639   -1.0094    0.1452 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4303   -0.4496    1.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2333    1.6592   -1.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3569    2.6536   -0.2817 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6262    2.7052    0.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8084    1.2559    2.6808 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7715    2.6242    2.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5751    1.1518    2.6723 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.7637    1.0046    0.9965 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1074    0.4794   -0.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0156   -0.6153    0.8436 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  2  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
 10 54  1  0
 11 55  1  0
 11 56  1  0
 12 57  1  0
 12 58  1  0
 13 59  1  0
 13 60  1  0
 14 61  1  0
 14 62  1  0
 15 63  1  0
 15 64  1  0
 16 65  1  0
 16 66  1  0
 17 67  1  0
 17 68  1  0
 21 69  1  0
 21 70  1  0
 22 71  1  6
 23 72  1  0
 24 73  1  0
 24 74  1  0
 30 75  1  0
 30 76  1  0
 31 77  1  0
 31 78  1  0
 33 79  1  0
 33 80  1  0
 33 81  1  0
 34 82  1  0
 34 83  1  0
 34 84  1  0
 35 85  1  0
 35 86  1  0
 35 87  1  0
M  CHG  2  28  -1  32   1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(9Z-Octadecenoyl)-sn-glycero-3-phosphocholine	ChEBI
1-Oleoyl-2-hydroxy-sn-glycero-3-phosphocholine	ChEBI
1-Oleoyl-sn-glycero-3-phosphorylcholine	ChEBI
1-Oleoylglycerophosphocholine	ChEBI
3-Oleoyl-rac-glycerol-1-phosphorylcholine	ChEBI
a 1-(9Z-Octadecenoyl)-sn-glycero-3-phosphocholine	ChEBI
LPC 18:1	ChEBI
LPC 18:1(9Z)/0:0	ChEBI
LPC(18:1(9Z)/0:0)	ChEBI
LysoPC 18:1(9Z)/0:0	ChEBI
Lysophosphatidylcholine 18:1	ChEBI
Lysophosphatidylcholine(18:1(9Z)/0:0)	ChEBI
PC 18:1(9Z)/0:0	ChEBI
PC(18:1(9Z)/0:0)	ChEBI
1-Oleoyl-glycero-3-phosphocholine	HMDB
LysoPC(18:1/0:0)	HMDB
LysoPC(18:1(9Z))	HMDB
Lysophosphatidylcholine(18:1)	HMDB
LysoPC(18:1)	HMDB
LyPC(18:1/0:0)	HMDB
LyPC(18:1)	HMDB
LPC(18:1/0:0)	HMDB
LPC(18:1)	HMDB
1-(9Z-Octadecenoyl)-glycero-3-phosphocholine	HMDB
Lysophosphatidylcholine(18:1/0:0)	HMDB
1-(9Z)-Octadecenoyl-sn-glycero-3-phosphocholine	HMDB
1-Oleoyl-sn-glycero-3-phosphocholine	HMDB
Choline phosphate (ester) 3-ester with 1-monoolein	HMDB
Choline phosphate 3-ester with 1-monoolein	HMDB
Gpcho(18:1(9Z)/0:0)[rac]	HMDB
LPC(18:1n9/0:0)	HMDB
LPC(18:1W9/0:0)	HMDB
LyPC(18:1W9/0:0)	HMDB
LysoPC a C18:1	HMDB
LysoPC(18:1n9/0:0)	HMDB
LysoPC(18:1W9/0:0)	HMDB
Lysophosphatidylcholine(18:1n9/0:0)	HMDB
Lysophosphatidylcholine(18:1W9/0:0)	HMDB
LysoPIC(18:1/0:0)	HMDB
Olein-1-mono-3-phosphate ester with choline	HMDB
Oleoyl lysolecithin	HMDB
Oleoyl lysophosphatidylcholine	HMDB
1-(cis-9-Octadecenoyl)-sn-glycero-3-phosphocholine	HMDB
1-OGPC	HMDB
1-Oleoyl lysophosphatidylcholine	HMDB
1-Oleoyl-lysopc	HMDB
1-O-Oleoyl-sn-glycero-3-phosphocholine	HMDB
1-Oleoyl-2-hydroxy-sn-glycerol-3-phosphocholine	HMDB
1-Oleoyl-GPC	HMDB
1-Oleoyl-lysophosphatidylcholine	HMDB
1-Oleoyl-sn-glycerol-3-phosphatidylcholine	HMDB
1-Oleoyl-sn-glycerol-3-phosphorylcholine	HMDB
GPC(18:1(9Z))	HMDB
GPC(18:1(9Z)/0:0)	HMDB
GPC(18:1)	HMDB
GPC(18:1n9)	HMDB
GPC(18:1n9/0:0)	HMDB
GPC(18:1W9)	HMDB
GPC(18:1W9/0:0)	HMDB
LPC(18:1(9Z))	HMDB
LPC(18:1n9)	HMDB
LPC(18:1W9)	HMDB
LysoPC(18:1n9)	HMDB
LysoPC(18:1W9)	HMDB
Lysophosphatidylcholine C18:1	HMDB
Lysophosphatidylcholine(18:1(9Z))	HMDB
Lysophosphatidylcholine(18:1n9)	HMDB
Lysophosphatidylcholine(18:1W9)	HMDB
LysoPC(18:1(9Z)/0:0)	ChEBI

Chemical Formula

C₂₆H₅₂NO₇P

Average Molecular Weight

521.6673

Monoisotopic Molecular Weight

521.348139535

IUPAC Name

(2-{[(2R)-2-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-2-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

19420-56-5

SMILES

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

InChI Identifier

InChI=1S/C26H52NO7P/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/h12-13,25,28H,5-11,14-24H2,1-4H3/b13-12-/t25-/m1/s1

InChI Key

YAMUFBLWGFFICM-PTGWMXDISA-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

oleoyl-sn-glycero-3-phosphocholine (CHEBI:28610 )
Monoacylglycerophosphocholines (LMGP01050032 )

Ontology

Physiological effect

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 18953024)

Organ

Placenta (HMDB: HMDB0002815)

Excreta

Biofluid or Excreta

Feces (PMID: 23384618)
Urine (PMID: 32340350)

Cellular substructure

Cell

All cells and tissues (HMDB: HMDB0002815)

Source

Exogenous

Exogenous (HMDB: HMDB0002815)

Food

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)

Endogenous

Endogenous (HMDB: HMDB0002815)

Process

Naturally occurring process

Biological process

Cellular process

Apoptosis (PMID: 30845751)

Biochemical pathway

Metabolic pathway

Lysolipid Incorporation into ER PC(18:1(9Z)/18:1(9Z)) (PathBank: SMP0002518)
Lysolipid Incorporation into Mitochondria PC(18:1(9Z)/18:1(9Z)) (PathBank: SMP0002526)

Role

Industrial application

Pharmaceutical industry

Biomarker

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	235.593	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001973

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00028 g/L	ALOGPS
logP	2.38	ALOGPS
logP	1.72	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	105.12 Å²	ChemAxon
Rotatable Bond Count	25	ChemAxon
Refractivity	152.59 m³·mol⁻¹	ChemAxon
Polarizability	60.02 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	250.532	30932474
DeepCCS	[M-H]-	247.272	30932474
DeepCCS	[M-2H]-	281.526	30932474
DeepCCS	[M+Na]+	258.03	30932474
AllCCS	[M+H]+	236.3	32859911
AllCCS	[M+H-H2O]+	235.1	32859911
AllCCS	[M+NH4]+	237.5	32859911
AllCCS	[M+Na]+	237.8	32859911
AllCCS	[M-H]-	231.7	32859911
AllCCS	[M+Na-2H]-	234.7	32859911
AllCCS	[M+HCOO]-	238.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
LysoPC(18:1(9Z)/0:0)	CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C	3651.9	Standard polar	33892256
LysoPC(18:1(9Z)/0:0)	CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C	3104.1	Standard non polar	33892256
LysoPC(18:1(9Z)/0:0)	CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C	3502.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
LysoPC(18:1(9Z)/0:0),1TMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O[Si](C)(C)C	3504.1	Semi standard non polar	33892256
LysoPC(18:1(9Z)/0:0),1TBDMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C	3728.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - LysoPC(18:1/0:0) GC-MS (1 TMS) - 70eV, Positive	splash10-024u-9431010000-8c34065bb1a9ce8460a8	2017-10-06	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(18:1/0:0) 10V, Negative-QTOF	splash10-00di-0030090000-c08a294df5c170ac8b76	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(18:1/0:0) 20V, Negative-QTOF	splash10-001i-1090010000-3f3fbc869926a73a5b72	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(18:1/0:0) 40V, Negative-QTOF	splash10-001i-0090000000-1894b105723e28dacec8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(18:1/0:0) 10V, Positive-QTOF	splash10-0fk9-0000090000-382efaabb1329b98f1ae	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(18:1/0:0) 20V, Positive-QTOF	splash10-0089-0900060000-7d4d5ee776e7a08537ae	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(18:1/0:0) 40V, Positive-QTOF	splash10-0ue9-0910040000-b15364334c9b09b73db5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(18:1/0:0) 10V, Positive-QTOF	splash10-0006-0000190000-ed1ce66db5beed8bfab7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(18:1/0:0) 20V, Positive-QTOF	splash10-000l-0001960000-b2d5105862a37356da93	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(18:1/0:0) 40V, Positive-QTOF	splash10-0gw0-1609710000-4adbedbb1f89568d7285	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(18:1/0:0) 10V, Negative-QTOF	splash10-0a4i-0000090000-f6a072a97b578a3bd0b0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(18:1/0:0) 20V, Negative-QTOF	splash10-053r-0090070000-f56fc89aebf13639f1ae	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(18:1/0:0) 40V, Negative-QTOF	splash10-001i-0090020000-be75beb7bf742731dc1e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(18:1/0:0) 10V, Positive-QTOF	splash10-004i-0000190000-37dcc74901c1425d0392	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(18:1/0:0) 20V, Positive-QTOF	splash10-0190-0002990000-c8110d0a5e4476020596	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(18:1/0:0) 40V, Positive-QTOF	splash10-0frj-0309400000-cd464845573077fb0e9f	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	31.5 +/- 10.4 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	37.47 +/- 7.73 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	11.7 (9.93-13.5) uM	Newborn (0-30 days old)	Not Available	Normal	25754623	details
Blood	Detected and Quantified	23.83(5.62) uM	Adult (>18 years old)	Both	Normal	26010610	details
Blood	Detected and Quantified	17.5 +/- 4.62 uM	Adult (>18 years old)	Both	Normal	28278231	details
Blood	Detected and Quantified	16.4 (13.4-21.2) uM	Infant (0-1 year old)	Not Available	Normal	25754623	details
Blood	Detected and Quantified	17.13 +/- 4.59 uM	Children (1-13 years old)	Both	Normal	23108202	details
Blood	Detected and Quantified	37.465 +/- 7.733 uM	Adult (>18 years old)	Both	Normal	18953024	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)	Both	Normal	23384618	details
Feces	Detected and Quantified	4.9 +/- 5.49 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected and Quantified	6.59 +/- 9.25 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Urine	Detected and Quantified	0.0-0.2 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	32340350	details
Urine	Detected and Quantified	0.02(0.0-0.24) umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	32340350	details
Urine	Detected and Quantified	0.01(0.0-0.05) umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	32340350	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	3.1(1.0-6.0) uM	Adult (>18 years old)	Both	Sepsis	26847922	details
Blood	Detected and Quantified	13.5 +/- 5.2 uM	Children (1-13 years old)	Both	Obese	24740590	details
Blood	Detected and Quantified	12.7 +/- 5.8 uM	Children (1-13 years old)	Both	Obese	24740590	details
Blood	Detected and Quantified	12.3 +/- 5.2 uM	Children (1-13 years old)	Both	Obese	24740590	details
Blood	Detected and Quantified	12.7 +/- -5.5 uM	Children (1-13 years old)	Both	Obese	24740590	details
Blood	Detected and Quantified	21.15(5.32) uM	Adult (>18 years old)	Both	Heart failure with preserved ejection fraction	26010610	details
Blood	Detected and Quantified	13.380 (12.740) uM	Adult (>18 years old)	Female	Pregnancy with fetus having congenital heart defect	24704061	details
Blood	Detected and Quantified	27.946 (9.468) uM	Adult (>18 years old)	Female	Pregnancy	24704061	details
Blood	Detected and Quantified	12.73 +/- 3.96 uM	Children (1-13 years old)	Both	Obese	23108202	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	liver cirrhosis	23384618	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	27275383	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 ]
Obesity
Reinehr T, Wolters B, Knop C, Lass N, Hellmuth C, Harder U, Peissner W, Wahl S, Grallert H, Adamski J, Illig T, Prehn C, Yu Z, Wang-Sattler R, Koletzko B: Changes in the serum metabolite profile in obese children with weight loss. Eur J Nutr. 2015 Mar;54(2):173-81. doi: 10.1007/s00394-014-0698-8. Epub 2014 Apr 17. [PubMed:24740590 ] Wahl S, Yu Z, Kleber M, Singmann P, Holzapfel C, He Y, Mittelstrass K, Polonikov A, Prehn C, Romisch-Margl W, Adamski J, Suhre K, Grallert H, Illig T, Wang-Sattler R, Reinehr T: Childhood obesity is associated with changes in the serum metabolite profile. Obes Facts. 2012;5(5):660-70. doi: 10.1159/000343204. Epub 2012 Oct 4. [PubMed:23108202 ]
Sepsis
Ferrario M, Cambiaghi A, Brunelli L, Giordano S, Caironi P, Guatteri L, Raimondi F, Gattinoni L, Latini R, Masson S, Ristagno G, Pastorelli R: Mortality prediction in patients with severe septic shock: a pilot study using a target metabolomics approach. Sci Rep. 2016 Feb 5;6:20391. doi: 10.1038/srep20391. [PubMed:26847922 ]
Cirrhosis
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 ]
Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]

Associated OMIM IDs

601665 (Obesity)
114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB005287

KNApSAcK ID

Not Available

Chemspider ID

17240641

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16081932

PDB ID

Not Available

ChEBI ID

28610

Food Biomarker Ontology

Not Available

VMH ID

PCHOLOLE_HS

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Chung, Guk Hoon; Kim, Sun Ki; Rhee, Joon Shick; Han, Jeong Joon. Process for preparing lysophospholipids using enzymes. U.S. (2001), 8 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Frasch SC, Zemski-Berry K, Murphy RC, Borregaard N, Henson PM, Bratton DL: Lysophospholipids of different classes mobilize neutrophil secretory vesicles and induce redundant signaling through G2A. J Immunol. 2007 May 15;178(10):6540-8. [PubMed:17475884 ]
Yang J, Zhao X, Liu X, Wang C, Gao P, Wang J, Li L, Gu J, Yang S, Xu G: High performance liquid chromatography-mass spectrometry for metabonomics: potential biomarkers for acute deterioration of liver function in chronic hepatitis B. J Proteome Res. 2006 Mar;5(3):554-61. [PubMed:16512670 ]
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 30 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 30 proteins in total.

Show all enzymes and transporters

Showing metabocard for LysoPC(18:1/0:0) (HMDB0002815)

MOL for HMDB0002815 (LysoPC(18:1/0:0))

3D MOL for HMDB0002815 (LysoPC(18:1/0:0))

3D SDF for HMDB0002815 (LysoPC(18:1/0:0))

3D-SDF for HMDB0002815 (LysoPC(18:1/0:0))

PDB for HMDB0002815 (LysoPC(18:1/0:0))

3D PDB for HMDB0002815 (LysoPC(18:1/0:0))

SMILES for HMDB0002815 (LysoPC(18:1/0:0))

INCHI for HMDB0002815 (LysoPC(18:1/0:0))

Structure for HMDB0002815 (LysoPC(18:1/0:0))

3D Structure for HMDB0002815 (LysoPC(18:1/0:0))

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes