Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (26) Show 26 proteins XML

enzymes (26) Show 26 proteins

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2008-10-29 14:26:36 UTC

Update Date

2022-11-30 19:03:55 UTC

HMDB ID

HMDB0011149

Secondary Accession Numbers

HMDB0062689
HMDB11149
HMDB62689

Metabolite Identification

Common Name

LysoPC(O-18:0/0:0)

Description

1-Octadecyl-sn-glycero-3-phosphocholine is an intermediate in the ether lipid metabolism pathway. 1-Octadecyl-sn-glycero-3-phosphocholine is irreversibly produced from 2-acetyl-1-(9Z-octadecenyl)-sn-glycero-3-phosphocholine via the enzyme 1-alkyl-2-acetylglycerophosphocholine esterase (EC 3.1.1.47). 1-Octadecyl-sn-glycero-3-phosphocholine is an ether phospho-ether lipid. Ether lipids are lipids in which one or more of the carbon atoms on glycerol are bonded to an alkyl chain via an ether linkage, as opposed to the usual ester linkage. Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids. LPL-R's are members of the G protein-coupled receptor (GPR) family of integral membrane proteins. Lysophosphatidylcholines (LPCs) specifically bind to GPR119, GPR40, GPR55 and GPR4. binding of LPCs to GPR119, GPR40 and GPR55 induces intracellular calcium mobilization and leads to increased glucose-stimulated insulin secretion in different cell systems. In blood or plasma LPCs are bound mainly to albumin and to a lesser extent to lipoproteins. Inflammation, cell damage and other pathophysiological conditions can profoundly alter the ratio of free to albumin bound LPC through increased production of LPC or decreased plasma levels of albumin (PMID: 32599910 ). In particular, lower levels of albumin (hypoalbuminemia) lead to lower levels of LPC in the blood. Hypoalbuminemia with albumin concentrations of <20 g/L are typical of patients with sepsis, burns or serious trauma (PMID: 26557421 ). Such low levels of albumin often lead to LPC levels that are 50-80 % lower than that seen in healthy individuals (PMID: 27501420 ). Decreased levels of LPC have been observed in a number of other inflammatory conditions beyond sepsis, including rheumatoid arthritis, diabetes, schizophrenia, polycystic ovary syndrome, Alzheimer’s disease, pulmonary arterial hypertension, aging, asthma and liver cirrhosis, where they were associated with increased mortality risk (PMID: 32599910 ). LPCs have a number of protective or anti-inflammatory effects. Higher levels of LPC induce cyclooxygenase-2 and endothelial nitric oxide synthase (eNOS) expression in endothelial cells, both of which can have vasoprotective effects either via production of prostacyclin or nitric oxide (PMID: 32599910 ). LPCs have been shown to elicit a number of effects on the innate immune system and effectively serve as dual-activity ligand molecules. In particular, LPCs directly activate toll-like receptor (TLR) 4 and TLR-2-1 receptors in the absence of classical TLR ligands. However, LPCs can also inhibit TLR-mediated signaling in the presence of classical TLR ligands, thereby acting as anti-inflammatory molecules (PMID: 32599910 ). Low levels of LPC during a bacterial or viral infection with TLR-mediated signalling can lead to opposing (inflammatory vs. anti-inflammatory) effects and immune dysregulation.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

LysoPC(O-18:0/0:0)
  Mrv1652311211919442D          

 34 33  0  0  0  0            999 V2000
   23.3644   -6.5407    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   23.3644   -7.3657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1894   -6.5407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9038   -6.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6183   -6.5407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3328   -6.1282    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   27.0473   -5.7157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7453   -6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9203   -5.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6620   -6.5288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3644   -5.7157    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   21.9475   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2330   -6.5288    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.5185   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8041   -6.5288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2330   -7.3538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0896   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3755   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6614   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9472   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2331   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5190   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8049   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0908   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3766   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6625   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9484   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2343   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5202   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8060   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0919   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3778   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6637   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9495   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  1 10  1  0  0  0  0
  1 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 17  1  0  0  0  0
 10 12  1  0  0  0  0
 13 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  CHG  2   6   1  11  -1
M  END

HMDB0011149
     RDKit          3D
LysoPC(O-18:0/0:0)
 90 89  0  0  0  0  0  0  0  0999 V2000
   -7.8733    0.2904   -3.3368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2769   -0.2752   -3.3754 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1733    0.4435   -2.4156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7442    0.3636   -0.9882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6835   -1.0544   -0.4711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2603   -1.1424    0.9548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8850   -0.5648    1.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8310   -1.2934    0.4095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4658   -0.6928    0.6540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1397   -0.8158    2.1154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7635   -0.2528    2.3928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7457    1.1987    2.0072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3701    1.7595    2.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9795    1.6651    3.7306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5993    2.2645    3.9156 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4645    1.5847    3.1151 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6501    0.1288    3.4238 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7885   -0.3415    2.4825 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3657   -0.1271    1.1928 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2307   -0.5263    0.2106 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5790    0.1029    0.1866 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3144   -0.1552    1.3292 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3486   -0.3255   -1.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5341    0.4106   -1.0849 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4208   -0.0279   -2.4568 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.5531    0.2519   -3.6656 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8661   -1.6566   -2.4032 O   0  0  0  0  0  1  0  0  0  0  0  0
    7.8239    0.9307   -2.4662 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9313    0.1278   -2.2779 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1649    1.0025   -2.2891 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3828    0.2590   -2.0996 N   0  0  0  0  0  4  0  0  0  0  0  0
   11.1400   -0.8449   -1.1839 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3587    1.1418   -1.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8826   -0.3196   -3.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7950    1.2288   -3.9251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2045   -0.5014   -3.7754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5529    0.4171   -2.2898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6862   -0.1956   -4.4034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1925   -1.3608   -3.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2086    0.0953   -2.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1366    1.5323   -2.7014 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5438    0.8881   -0.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8135    0.9276   -0.7750 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6928   -1.5109   -0.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0156   -1.6951   -1.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1999   -2.2180    1.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0271   -0.7015    1.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8012    0.4977    1.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7162   -0.7133    2.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8024   -2.3548    0.7404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0148   -1.2566   -0.6688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7166   -1.1877    0.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5657    0.3842    0.3273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8469   -0.2347    2.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1445   -1.8811    2.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0288   -0.8536    1.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6233   -0.3818    3.5025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9449    1.3406    0.9233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5150    1.7826    2.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6551    1.1437    1.6749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3893    2.8119    1.9373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6754    2.3206    4.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0512    0.6661    4.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3279    2.3730    4.9809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6714    3.3131    3.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4332    2.0902    3.3494 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3319    1.6982    2.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2269   -0.4839    3.1567 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0080   -0.0837    4.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0889   -1.3717    2.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6234    0.3975    2.6872 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7456   -0.3174   -0.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3069   -1.6592    0.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5180    1.2268    0.0927 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0402   -0.8132    1.1187 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7501   -0.0347   -1.9321 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5628   -1.4176   -1.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8162   -0.4312   -1.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0219   -0.5543   -3.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1963    1.5363   -3.2613 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1233    1.7918   -1.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5992   -1.6875   -1.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1165   -1.2321   -0.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5608   -0.5237   -0.2857 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0088    1.3918   -0.4815 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3942    2.1072   -2.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3734    0.7066   -1.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4431   -1.3124   -3.4513 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9840   -0.4833   -3.1605 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7312    0.3485   -4.1865 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  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 25 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  1  0
 31 34  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  0
  2 39  1  0
  3 40  1  0
  3 41  1  0
  4 42  1  0
  4 43  1  0
  5 44  1  0
  5 45  1  0
  6 46  1  0
  6 47  1  0
  7 48  1  0
  7 49  1  0
  8 50  1  0
  8 51  1  0
  9 52  1  0
  9 53  1  0
 10 54  1  0
 10 55  1  0
 11 56  1  0
 11 57  1  0
 12 58  1  0
 12 59  1  0
 13 60  1  0
 13 61  1  0
 14 62  1  0
 14 63  1  0
 15 64  1  0
 15 65  1  0
 16 66  1  0
 16 67  1  0
 17 68  1  0
 17 69  1  0
 18 70  1  0
 18 71  1  0
 20 72  1  0
 20 73  1  0
 21 74  1  6
 22 75  1  0
 23 76  1  0
 23 77  1  0
 29 78  1  0
 29 79  1  0
 30 80  1  0
 30 81  1  0
 32 82  1  0
 32 83  1  0
 32 84  1  0
 33 85  1  0
 33 86  1  0
 33 87  1  0
 34 88  1  0
 34 89  1  0
 34 90  1  0
M  CHG  2  27  -1  31   1
M  END

LysoPC(O-18:0/0:0)
  Mrv1652311211919442D          

 34 33  0  0  0  0            999 V2000
   23.3644   -6.5407    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   23.3644   -7.3657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1894   -6.5407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9038   -6.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6183   -6.5407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3328   -6.1282    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   27.0473   -5.7157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7453   -6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9203   -5.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6620   -6.5288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3644   -5.7157    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   21.9475   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2330   -6.5288    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.5185   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8041   -6.5288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2330   -7.3538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0896   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3755   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6614   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9472   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2331   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5190   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8049   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0908   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3766   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6625   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9484   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2343   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5202   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8060   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0919   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3778   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6637   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9495   -6.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  1 10  1  0  0  0  0
  1 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 17  1  0  0  0  0
 10 12  1  0  0  0  0
 13 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  CHG  2   6   1  11  -1
M  END
> <DATABASE_ID>
HMDB0011149

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C26H56NO6P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-22-31-24-26(28)25-33-34(29,30)32-23-21-27(2,3)4/h26,28H,5-25H2,1-4H3/t26-/m1/s1

> <INCHI_KEY>
XKBJVQHMEXMFDZ-AREMUKBSSA-N

> <FORMULA>
C26H56NO6P

> <MOLECULAR_WEIGHT>
509.6997

> <EXACT_MASS>
509.384525041

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
90

> <JCHEM_AVERAGE_POLARIZABILITY>
62.69589771197418

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
2.98

> <JCHEM_LOGP>
2.462675402861589

> <ALOGPS_LOGS>
-6.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.680359309358309

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8553441415966123

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3931778346128443

> <JCHEM_POLAR_SURFACE_AREA>
88.05

> <JCHEM_REFRACTIVITY>
151.72109999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
26

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.67e-04 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0011149
     RDKit          3D
LysoPC(O-18:0/0:0)
 90 89  0  0  0  0  0  0  0  0999 V2000
   -7.8733    0.2904   -3.3368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2769   -0.2752   -3.3754 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1733    0.4435   -2.4156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7442    0.3636   -0.9882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6835   -1.0544   -0.4711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2603   -1.1424    0.9548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8850   -0.5648    1.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8310   -1.2934    0.4095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4658   -0.6928    0.6540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1397   -0.8158    2.1154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7635   -0.2528    2.3928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7457    1.1987    2.0072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3701    1.7595    2.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9795    1.6651    3.7306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5993    2.2645    3.9156 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4645    1.5847    3.1151 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6501    0.1288    3.4238 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7885   -0.3415    2.4825 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3657   -0.1271    1.1928 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2307   -0.5263    0.2106 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5790    0.1029    0.1866 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3144   -0.1552    1.3292 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3486   -0.3255   -1.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5341    0.4106   -1.0849 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4208   -0.0279   -2.4568 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.5531    0.2519   -3.6656 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8661   -1.6566   -2.4032 O   0  0  0  0  0  1  0  0  0  0  0  0
    7.8239    0.9307   -2.4662 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9313    0.1278   -2.2779 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1649    1.0025   -2.2891 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3828    0.2590   -2.0996 N   0  0  0  0  0  4  0  0  0  0  0  0
   11.1400   -0.8449   -1.1839 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3587    1.1418   -1.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8826   -0.3196   -3.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7950    1.2288   -3.9251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2045   -0.5014   -3.7754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5529    0.4171   -2.2898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6862   -0.1956   -4.4034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1925   -1.3608   -3.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2086    0.0953   -2.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1366    1.5323   -2.7014 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5438    0.8881   -0.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8135    0.9276   -0.7750 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6928   -1.5109   -0.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0156   -1.6951   -1.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1999   -2.2180    1.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0271   -0.7015    1.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8012    0.4977    1.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7162   -0.7133    2.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8024   -2.3548    0.7404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0148   -1.2566   -0.6688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7166   -1.1877    0.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5657    0.3842    0.3273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8469   -0.2347    2.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1445   -1.8811    2.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0288   -0.8536    1.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6233   -0.3818    3.5025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9449    1.3406    0.9233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5150    1.7826    2.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6551    1.1437    1.6749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3893    2.8119    1.9373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6754    2.3206    4.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0512    0.6661    4.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3279    2.3730    4.9809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6714    3.3131    3.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4332    2.0902    3.3494 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3319    1.6982    2.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2269   -0.4839    3.1567 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0080   -0.0837    4.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0889   -1.3717    2.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6234    0.3975    2.6872 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7456   -0.3174   -0.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3069   -1.6592    0.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5180    1.2268    0.0927 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0402   -0.8132    1.1187 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7501   -0.0347   -1.9321 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5628   -1.4176   -1.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8162   -0.4312   -1.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0219   -0.5543   -3.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1963    1.5363   -3.2613 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1233    1.7918   -1.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5992   -1.6875   -1.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1165   -1.2321   -0.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5608   -0.5237   -0.2857 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0088    1.3918   -0.4815 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3942    2.1072   -2.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3734    0.7066   -1.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4431   -1.3124   -3.4513 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9840   -0.4833   -3.1605 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7312    0.3485   -4.1865 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  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 25 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  1  0
 31 34  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  0
  2 39  1  0
  3 40  1  0
  3 41  1  0
  4 42  1  0
  4 43  1  0
  5 44  1  0
  5 45  1  0
  6 46  1  0
  6 47  1  0
  7 48  1  0
  7 49  1  0
  8 50  1  0
  8 51  1  0
  9 52  1  0
  9 53  1  0
 10 54  1  0
 10 55  1  0
 11 56  1  0
 11 57  1  0
 12 58  1  0
 12 59  1  0
 13 60  1  0
 13 61  1  0
 14 62  1  0
 14 63  1  0
 15 64  1  0
 15 65  1  0
 16 66  1  0
 16 67  1  0
 17 68  1  0
 17 69  1  0
 18 70  1  0
 18 71  1  0
 20 72  1  0
 20 73  1  0
 21 74  1  6
 22 75  1  0
 23 76  1  0
 23 77  1  0
 29 78  1  0
 29 79  1  0
 30 80  1  0
 30 81  1  0
 32 82  1  0
 32 83  1  0
 32 84  1  0
 33 85  1  0
 33 86  1  0
 33 87  1  0
 34 88  1  0
 34 89  1  0
 34 90  1  0
M  CHG  2  27  -1  31   1
M  END

HEADER    PROTEIN                                 21-NOV-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: LysoPC(O-18:0/0:0)                                
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-NOV-19         0                                  
HETATM    1  P   UNK     0      43.614 -12.209   0.000  0.00  0.00           P+0
HETATM    2  O   UNK     0      43.614 -13.749   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      45.154 -12.209   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      46.487 -11.439   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      47.821 -12.209   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      49.155 -11.439   0.000  0.00  0.00           N+1
HETATM    7  C   UNK     0      50.488 -10.669   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      49.925 -12.773   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      48.385 -10.106   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      42.302 -12.187   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      43.614 -10.669   0.000  0.00  0.00           O-1
HETATM   12  C   UNK     0      40.969 -11.417   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      39.635 -12.187   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      38.301 -11.417   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      36.968 -12.187   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      39.635 -13.727   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      35.634 -11.417   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      34.301 -12.188   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      32.968 -11.417   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      31.635 -12.188   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      30.302 -11.417   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      28.969 -12.188   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      27.636 -11.417   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      26.303 -12.188   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      24.970 -11.417   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      23.637 -12.188   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      22.304 -11.417   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      20.971 -12.188   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      19.638 -11.417   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      18.305 -12.188   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.972 -11.417   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      15.639 -12.188   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      14.306 -11.417   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.972 -12.188   0.000  0.00  0.00           C+0
CONECT    1    2    3   10   11                                             
CONECT    2    1                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6                                                            
CONECT   10    1   12                                                       
CONECT   11    1                                                            
CONECT   12   13   10                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14   17                                                       
CONECT   16   13                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   66    0
END

COMPND    HMDB0011149
HETATM    1  C1  UNL     1      -7.873   0.290  -3.337  1.00  0.00           C  
HETATM    2  C2  UNL     1      -9.277  -0.275  -3.375  1.00  0.00           C  
HETATM    3  C3  UNL     1     -10.173   0.443  -2.416  1.00  0.00           C  
HETATM    4  C4  UNL     1      -9.744   0.364  -0.988  1.00  0.00           C  
HETATM    5  C5  UNL     1      -9.683  -1.054  -0.471  1.00  0.00           C  
HETATM    6  C6  UNL     1      -9.260  -1.142   0.955  1.00  0.00           C  
HETATM    7  C7  UNL     1      -7.885  -0.565   1.210  1.00  0.00           C  
HETATM    8  C8  UNL     1      -6.831  -1.293   0.410  1.00  0.00           C  
HETATM    9  C9  UNL     1      -5.466  -0.693   0.654  1.00  0.00           C  
HETATM   10  C10 UNL     1      -5.140  -0.816   2.115  1.00  0.00           C  
HETATM   11  C11 UNL     1      -3.764  -0.253   2.393  1.00  0.00           C  
HETATM   12  C12 UNL     1      -3.746   1.199   2.007  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.370   1.759   2.293  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.980   1.665   3.731  1.00  0.00           C  
HETATM   15  C15 UNL     1      -0.599   2.265   3.916  1.00  0.00           C  
HETATM   16  C16 UNL     1       0.464   1.585   3.115  1.00  0.00           C  
HETATM   17  C17 UNL     1       0.650   0.129   3.424  1.00  0.00           C  
HETATM   18  C18 UNL     1       1.788  -0.341   2.482  1.00  0.00           C  
HETATM   19  O1  UNL     1       1.366  -0.127   1.193  1.00  0.00           O  
HETATM   20  C19 UNL     1       2.231  -0.526   0.211  1.00  0.00           C  
HETATM   21  C20 UNL     1       3.579   0.103   0.187  1.00  0.00           C  
HETATM   22  O2  UNL     1       4.314  -0.155   1.329  1.00  0.00           O  
HETATM   23  C21 UNL     1       4.349  -0.326  -1.067  1.00  0.00           C  
HETATM   24  O3  UNL     1       5.534   0.411  -1.085  1.00  0.00           O  
HETATM   25  P1  UNL     1       6.421  -0.028  -2.457  1.00  0.00           P  
HETATM   26  O4  UNL     1       5.553   0.252  -3.666  1.00  0.00           O  
HETATM   27  O5  UNL     1       6.866  -1.657  -2.403  1.00  0.00           O1-
HETATM   28  O6  UNL     1       7.824   0.931  -2.466  1.00  0.00           O  
HETATM   29  C22 UNL     1       8.931   0.128  -2.278  1.00  0.00           C  
HETATM   30  C23 UNL     1      10.165   1.003  -2.289  1.00  0.00           C  
HETATM   31  N1  UNL     1      11.383   0.259  -2.100  1.00  0.00           N1+
HETATM   32  C24 UNL     1      11.140  -0.845  -1.184  1.00  0.00           C  
HETATM   33  C25 UNL     1      12.359   1.142  -1.489  1.00  0.00           C  
HETATM   34  C26 UNL     1      11.883  -0.320  -3.332  1.00  0.00           C  
HETATM   35  H1  UNL     1      -7.795   1.229  -3.925  1.00  0.00           H  
HETATM   36  H2  UNL     1      -7.204  -0.501  -3.775  1.00  0.00           H  
HETATM   37  H3  UNL     1      -7.553   0.417  -2.290  1.00  0.00           H  
HETATM   38  H4  UNL     1      -9.686  -0.196  -4.403  1.00  0.00           H  
HETATM   39  H5  UNL     1      -9.192  -1.361  -3.167  1.00  0.00           H  
HETATM   40  H6  UNL     1     -11.209   0.095  -2.498  1.00  0.00           H  
HETATM   41  H7  UNL     1     -10.137   1.532  -2.701  1.00  0.00           H  
HETATM   42  H8  UNL     1     -10.544   0.888  -0.388  1.00  0.00           H  
HETATM   43  H9  UNL     1      -8.814   0.928  -0.775  1.00  0.00           H  
HETATM   44  H10 UNL     1     -10.693  -1.511  -0.549  1.00  0.00           H  
HETATM   45  H11 UNL     1      -9.016  -1.695  -1.082  1.00  0.00           H  
HETATM   46  H12 UNL     1      -9.200  -2.218   1.224  1.00  0.00           H  
HETATM   47  H13 UNL     1     -10.027  -0.701   1.611  1.00  0.00           H  
HETATM   48  H14 UNL     1      -7.801   0.498   1.003  1.00  0.00           H  
HETATM   49  H15 UNL     1      -7.716  -0.713   2.306  1.00  0.00           H  
HETATM   50  H16 UNL     1      -6.802  -2.355   0.740  1.00  0.00           H  
HETATM   51  H17 UNL     1      -7.015  -1.257  -0.669  1.00  0.00           H  
HETATM   52  H18 UNL     1      -4.717  -1.188   0.009  1.00  0.00           H  
HETATM   53  H19 UNL     1      -5.566   0.384   0.327  1.00  0.00           H  
HETATM   54  H20 UNL     1      -5.847  -0.235   2.746  1.00  0.00           H  
HETATM   55  H21 UNL     1      -5.144  -1.881   2.393  1.00  0.00           H  
HETATM   56  H22 UNL     1      -3.029  -0.854   1.860  1.00  0.00           H  
HETATM   57  H23 UNL     1      -3.623  -0.382   3.502  1.00  0.00           H  
HETATM   58  H24 UNL     1      -3.945   1.341   0.923  1.00  0.00           H  
HETATM   59  H25 UNL     1      -4.515   1.783   2.537  1.00  0.00           H  
HETATM   60  H26 UNL     1      -1.655   1.144   1.675  1.00  0.00           H  
HETATM   61  H27 UNL     1      -2.389   2.812   1.937  1.00  0.00           H  
HETATM   62  H28 UNL     1      -2.675   2.321   4.314  1.00  0.00           H  
HETATM   63  H29 UNL     1      -2.051   0.666   4.164  1.00  0.00           H  
HETATM   64  H30 UNL     1      -0.328   2.373   4.981  1.00  0.00           H  
HETATM   65  H31 UNL     1      -0.671   3.313   3.515  1.00  0.00           H  
HETATM   66  H32 UNL     1       1.433   2.090   3.349  1.00  0.00           H  
HETATM   67  H33 UNL     1       0.332   1.698   2.024  1.00  0.00           H  
HETATM   68  H34 UNL     1      -0.227  -0.484   3.157  1.00  0.00           H  
HETATM   69  H35 UNL     1       1.008  -0.084   4.436  1.00  0.00           H  
HETATM   70  H36 UNL     1       2.089  -1.372   2.699  1.00  0.00           H  
HETATM   71  H37 UNL     1       2.623   0.398   2.687  1.00  0.00           H  
HETATM   72  H38 UNL     1       1.746  -0.317  -0.785  1.00  0.00           H  
HETATM   73  H39 UNL     1       2.307  -1.659   0.252  1.00  0.00           H  
HETATM   74  H40 UNL     1       3.518   1.227   0.093  1.00  0.00           H  
HETATM   75  H41 UNL     1       5.040  -0.813   1.119  1.00  0.00           H  
HETATM   76  H42 UNL     1       3.750  -0.035  -1.932  1.00  0.00           H  
HETATM   77  H43 UNL     1       4.563  -1.418  -1.028  1.00  0.00           H  
HETATM   78  H44 UNL     1       8.816  -0.431  -1.339  1.00  0.00           H  
HETATM   79  H45 UNL     1       9.022  -0.554  -3.166  1.00  0.00           H  
HETATM   80  H46 UNL     1      10.196   1.536  -3.261  1.00  0.00           H  
HETATM   81  H47 UNL     1      10.123   1.792  -1.511  1.00  0.00           H  
HETATM   82  H48 UNL     1      10.599  -1.687  -1.659  1.00  0.00           H  
HETATM   83  H49 UNL     1      12.117  -1.232  -0.779  1.00  0.00           H  
HETATM   84  H50 UNL     1      10.561  -0.524  -0.286  1.00  0.00           H  
HETATM   85  H51 UNL     1      12.009   1.392  -0.481  1.00  0.00           H  
HETATM   86  H52 UNL     1      12.394   2.107  -2.054  1.00  0.00           H  
HETATM   87  H53 UNL     1      13.373   0.707  -1.503  1.00  0.00           H  
HETATM   88  H54 UNL     1      11.443  -1.312  -3.451  1.00  0.00           H  
HETATM   89  H55 UNL     1      12.984  -0.483  -3.160  1.00  0.00           H  
HETATM   90  H56 UNL     1      11.731   0.349  -4.187  1.00  0.00           H  
CONECT    1    2   35   36   37
CONECT    2    3   38   39
CONECT    3    4   40   41
CONECT    4    5   42   43
CONECT    5    6   44   45
CONECT    6    7   46   47
CONECT    7    8   48   49
CONECT    8    9   50   51
CONECT    9   10   52   53
CONECT   10   11   54   55
CONECT   11   12   56   57
CONECT   12   13   58   59
CONECT   13   14   60   61
CONECT   14   15   62   63
CONECT   15   16   64   65
CONECT   16   17   66   67
CONECT   17   18   68   69
CONECT   18   19   70   71
CONECT   19   20
CONECT   20   21   72   73
CONECT   21   22   23   74
CONECT   22   75
CONECT   23   24   76   77
CONECT   24   25
CONECT   25   26   26   27   28
CONECT   28   29
CONECT   29   30   78   79
CONECT   30   31   80   81
CONECT   31   32   33   34
CONECT   32   82   83   84
CONECT   33   85   86   87
CONECT   34   88   89   90
END

HMDB0011149
     RDKit          3D
LysoPC(O-18:0/0:0)
 90 89  0  0  0  0  0  0  0  0999 V2000
   -7.8733    0.2904   -3.3368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2769   -0.2752   -3.3754 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1733    0.4435   -2.4156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7442    0.3636   -0.9882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6835   -1.0544   -0.4711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2603   -1.1424    0.9548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8850   -0.5648    1.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8310   -1.2934    0.4095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4658   -0.6928    0.6540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1397   -0.8158    2.1154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7635   -0.2528    2.3928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7457    1.1987    2.0072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3701    1.7595    2.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9795    1.6651    3.7306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5993    2.2645    3.9156 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4645    1.5847    3.1151 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6501    0.1288    3.4238 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7885   -0.3415    2.4825 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3657   -0.1271    1.1928 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2307   -0.5263    0.2106 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5790    0.1029    0.1866 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3144   -0.1552    1.3292 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3486   -0.3255   -1.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5341    0.4106   -1.0849 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4208   -0.0279   -2.4568 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.5531    0.2519   -3.6656 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8661   -1.6566   -2.4032 O   0  0  0  0  0  1  0  0  0  0  0  0
    7.8239    0.9307   -2.4662 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9313    0.1278   -2.2779 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1649    1.0025   -2.2891 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3828    0.2590   -2.0996 N   0  0  0  0  0  4  0  0  0  0  0  0
   11.1400   -0.8449   -1.1839 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3587    1.1418   -1.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8826   -0.3196   -3.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7950    1.2288   -3.9251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2045   -0.5014   -3.7754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5529    0.4171   -2.2898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6862   -0.1956   -4.4034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1925   -1.3608   -3.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2086    0.0953   -2.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1366    1.5323   -2.7014 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5438    0.8881   -0.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8135    0.9276   -0.7750 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6928   -1.5109   -0.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0156   -1.6951   -1.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1999   -2.2180    1.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0271   -0.7015    1.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8012    0.4977    1.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7162   -0.7133    2.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8024   -2.3548    0.7404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0148   -1.2566   -0.6688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7166   -1.1877    0.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5657    0.3842    0.3273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8469   -0.2347    2.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1445   -1.8811    2.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0288   -0.8536    1.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6233   -0.3818    3.5025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9449    1.3406    0.9233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5150    1.7826    2.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6551    1.1437    1.6749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3893    2.8119    1.9373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6754    2.3206    4.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0512    0.6661    4.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3279    2.3730    4.9809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6714    3.3131    3.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4332    2.0902    3.3494 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3319    1.6982    2.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2269   -0.4839    3.1567 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0080   -0.0837    4.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0889   -1.3717    2.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6234    0.3975    2.6872 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7456   -0.3174   -0.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3069   -1.6592    0.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5180    1.2268    0.0927 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0402   -0.8132    1.1187 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7501   -0.0347   -1.9321 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5628   -1.4176   -1.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8162   -0.4312   -1.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0219   -0.5543   -3.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1963    1.5363   -3.2613 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1233    1.7918   -1.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5992   -1.6875   -1.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1165   -1.2321   -0.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5608   -0.5237   -0.2857 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0088    1.3918   -0.4815 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3942    2.1072   -2.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3734    0.7066   -1.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4431   -1.3124   -3.4513 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9840   -0.4833   -3.1605 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7312    0.3485   -4.1865 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  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 25 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  1  0
 31 34  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  0
  2 39  1  0
  3 40  1  0
  3 41  1  0
  4 42  1  0
  4 43  1  0
  5 44  1  0
  5 45  1  0
  6 46  1  0
  6 47  1  0
  7 48  1  0
  7 49  1  0
  8 50  1  0
  8 51  1  0
  9 52  1  0
  9 53  1  0
 10 54  1  0
 10 55  1  0
 11 56  1  0
 11 57  1  0
 12 58  1  0
 12 59  1  0
 13 60  1  0
 13 61  1  0
 14 62  1  0
 14 63  1  0
 15 64  1  0
 15 65  1  0
 16 66  1  0
 16 67  1  0
 17 68  1  0
 17 69  1  0
 18 70  1  0
 18 71  1  0
 20 72  1  0
 20 73  1  0
 21 74  1  6
 22 75  1  0
 23 76  1  0
 23 77  1  0
 29 78  1  0
 29 79  1  0
 30 80  1  0
 30 81  1  0
 32 82  1  0
 32 83  1  0
 32 84  1  0
 33 85  1  0
 33 86  1  0
 33 87  1  0
 34 88  1  0
 34 89  1  0
 34 90  1  0
M  CHG  2  27  -1  31   1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-O-Octadecylglycerol-3-phosphatidylcholine	HMDB
1-Octadecyl-sn-glycero-3-phosphocholine	HMDB
1-Stearyl-GPC	HMDB
1-Stearyl-GPC (O-18:0)	HMDB
GPC(O-18:0)	HMDB
GPC(O-18:0/0:0)	HMDB
LPC (O-18:0)	HMDB
LysoPC(18:0E/0:0)	HMDB
LysoPC(O-18:0)	HMDB
PC(O-18:0/0:0)	HMDB
LysoPC(DM18:0)	HMDB
1-O-Octadecyl-sn-glycero-3-phosphocholine	HMDB
1-O-Octadecyl-sn-glyceryl-3-phosphorylcholine	HMDB
1-Octadecyl-GPC	HMDB
1-Octadecyl-lysophosphatidylcholine	HMDB
1-Octadecylglycero-3-phosphocholine	HMDB
GPC(18:0)	HMDB
GPC(18:0/0:0)	HMDB
LPC(18:0)	HMDB
LPC(18:0/0:0)	HMDB
LPC(O-18:0)	HMDB
LPC(O-18:0/0:0)	HMDB
Lyso-platelet-activating factor	HMDB
LysoPC(18:0)	HMDB
LysoPC(18:0/0:0)	HMDB
Lysophosphatidylcholine(18:0)	HMDB
Lysophosphatidylcholine(18:0/0:0)	HMDB
Lysophosphatidylcholine(O-18:0)	HMDB
Lysophosphatidylcholine(O-18:0/0:0)	HMDB
LysoPC(O-18:0/0:0)	HMDB

Chemical Formula

C₂₆H₅₆NO₆P

Average Molecular Weight

509.6997

Monoisotopic Molecular Weight

509.384525041

IUPAC Name

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

Traditional Name

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

CAS Registry Number

74430-89-0

SMILES

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

InChI Identifier

InChI=1S/C26H56NO6P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-22-31-24-26(28)25-33-34(29,30)32-23-21-27(2,3)4/h26,28H,5-25H2,1-4H3/t26-/m1/s1

InChI Key

XKBJVQHMEXMFDZ-AREMUKBSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monoalkylglycerophosphocholines. Monoalkylglycerophosphocholines are compounds containing glycerophosphocholine moiety attached to an fatty acyl chain through an ether bond.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphocholines

Direct Parent

Monoalkylglycerophosphocholines

Alternative Parents

Substituents

Monoalkylglycerophosphocholine
Phosphocholine
Glycerol ether
Dialkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Quaternary ammonium salt
Tetraalkylammonium salt
Secondary alcohol
Ether
Dialkyl ether
Hydrocarbon derivative
Alcohol
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Amine
Organic salt
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

organic molecular entity (CHEBI:75216 )
1-alkyl-sn-glycero-3-phosphocholine (CHEBI:75216 )
Monoalkylglycerophosphocholines (LMGP01060014 )

Ontology

Physiological effect

Organoleptic effect

Touch

Smooth (HMDB: HMDB0011149)

Disposition

Biological location

Cell membrane (HMDB: HMDB0011149)
Intracellular membrane (HMDB: HMDB0011149)

Biofluid or Excreta

Blood (HMDB: HMDB0011149)

Excreta

Biofluid or Excreta

Feces (PMID: 23210743)

Cellular substructure

Extracellular (HMDB: HMDB0011149)
Membrane (HMDB: HMDB0011149)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0011149)

Source

Endogenous

Endogenous (HMDB: HMDB0011149)

Animal

Animal (HMDB: HMDB0011149)

Exogenous

Food

Food (HMDB: HMDB0011149)

Animal origin

Poultry

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
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)

Equine

Horse (FooDB: FOOD00378)

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)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0011149)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0011149)

Cellular process

Cell signaling (HMDB: HMDB0011149)

Biochemical pathway

Glycerophospholipid metabolism (HMDB: HMDB0011149)

Role

Biological role

Energy source (HMDB: HMDB0011149)

Industrial application

Food and nutrition

Food additive

Nutritional supplement

Nutritional supplement (HMDB: HMDB0011149)

Food additive (HMDB: HMDB0011149)

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0011149)

Emulsifier (HMDB: HMDB0011149)

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	0.00027 g/L	ALOGPS
logP	2.98	ALOGPS
logP	2.46	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	88.05 Å²	ChemAxon
Rotatable Bond Count	26	ChemAxon
Refractivity	151.72 m³·mol⁻¹	ChemAxon
Polarizability	62.7 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]+	233.648	30932474
DeepCCS	[M-H]-	230.561	30932474
DeepCCS	[M-2H]-	264.636	30932474
DeepCCS	[M+Na]+	241.145	30932474
AllCCS	[M+H]+	240.1	32859911
AllCCS	[M+H-H2O]+	238.8	32859911
AllCCS	[M+NH4]+	241.2	32859911
AllCCS	[M+Na]+	241.6	32859911
AllCCS	[M-H]-	234.4	32859911
AllCCS	[M+Na-2H]-	236.8	32859911
AllCCS	[M+HCOO]-	239.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
LysoPC(O-18:0/0:0)	CCCCCCCCCCCCCCCCCCOC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C	3398.2	Standard polar	33892256
LysoPC(O-18:0/0:0)	CCCCCCCCCCCCCCCCCCOC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C	3220.0	Standard non polar	33892256
LysoPC(O-18:0/0:0)	CCCCCCCCCCCCCCCCCCOC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C	3436.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
LysoPC(O-18:0/0:0),1TMS,isomer #1	CCCCCCCCCCCCCCCCCCOC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O[Si](C)(C)C	3393.2	Semi standard non polar	33892256
LysoPC(O-18:0/0:0),1TBDMS,isomer #1	CCCCCCCCCCCCCCCCCCOC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C	3654.2	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(O-18:0/0:0) GC-MS (Non-derivatized) - 70eV, Positive	splash10-000t-5930000000-c002f9346ff27ec388a3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - LysoPC(O-18:0/0:0) GC-MS (1 TMS) - 70eV, Positive	splash10-0002-9460000000-f8bf856a15fd2cd2fa22	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(O-18:0/0:0) 10V, Positive-QTOF	splash10-01p9-9123230000-9e5018d60ea3b2b28b32	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(O-18:0/0:0) 20V, Positive-QTOF	splash10-0ugr-9455200000-0c72dc03f55ca1a4599e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(O-18:0/0:0) 40V, Positive-QTOF	splash10-0f79-9231000000-adbce76401a5b20f74d5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(O-18:0/0:0) 10V, Negative-QTOF	splash10-0a4i-0010490000-78228db3f0e06f9d298c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(O-18:0/0:0) 20V, Negative-QTOF	splash10-0ar0-2160920000-56a3704799b8868294e2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(O-18:0/0:0) 40V, Negative-QTOF	splash10-00or-9280000000-a127711d12f38e903413	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(O-18:0/0:0) 10V, Positive-QTOF	splash10-001i-0000090000-92389686f000bb55e113	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(O-18:0/0:0) 20V, Positive-QTOF	splash10-001i-0000090000-92389686f000bb55e113	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(O-18:0/0:0) 40V, Positive-QTOF	splash10-00di-0000930000-3fa7cb0f3d40c52c6b6a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(O-18:0/0:0) 10V, Negative-QTOF	splash10-0a4i-0000090000-0092c5cfc59f1e835b62	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(O-18:0/0:0) 20V, Negative-QTOF	splash10-0a4i-0020290000-1cacf188cd006762529a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(O-18:0/0:0) 40V, Negative-QTOF	splash10-004i-9210100000-3e2f6987fc891e79e2c0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(O-18:0/0:0) 10V, Negative-QTOF	splash10-0006-0000090000-ac3949a1bc7527be80e6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(O-18:0/0:0) 20V, Negative-QTOF	splash10-0006-0110690000-b1a4faf5ff77d30fbafc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(O-18:0/0:0) 40V, Negative-QTOF	splash10-0006-0110910000-2f268286db3bc04e9cec	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(O-18:0/0:0) 10V, Positive-QTOF	splash10-0il0-1900160000-4dc04f9d727b989bed34	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(O-18:0/0:0) 20V, Positive-QTOF	splash10-0ik9-1710190000-87893f3898856e238ceb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(O-18:0/0:0) 40V, Positive-QTOF	splash10-0ik9-0710190000-487f87885e45a61ac64d	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Newborn (0-30 days old)	Not Specified	Premature neonates	23210743	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB027924

KNApSAcK ID

Not Available

Chemspider ID

2015318

KEGG Compound ID

C04317

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

2733532

PDB ID

Not Available

ChEBI ID

75216

Food Biomarker Ontology

Not Available

VMH ID

AK2LGCHOL_HS

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Only showing the first 10 proteins. There are 26 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. 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

2. 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

3. 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

4. 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

5. 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

6. 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

7. 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

8. 85/88 kDa calcium-independent phospholipase A2

General function:: Involved in metabolic process
Specific function:: Catalyzes the release of fatty acids from phospholipids. It has been implicated in normal phospholipid remodeling, nitric oxide-induced or vasopressin-induced arachidonic acid release and in leukotriene and prostaglandin production. May participate in fas mediated apoptosis and in regulating transmembrane ion flux in glucose-stimulated B-cells. Has a role in cardiolipin (CL) deacylation. Required for both speed and directionality of monocyte MCP1/CCL2-induced chemotaxis through regulation of F-actin polymerization at the pseudopods. Isoform ankyrin-iPLA2-1 and isoform ankyrin-iPLA2-2, which lack the catalytic domain, are probably involved in the negative regulation of iPLA2 activity.
Gene Name:: PLA2G6
Uniprot ID:: O60733
Molecular weight:: 84092.635

Enzyme Details

9. Eosinophil lysophospholipase

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

Enzyme Details

10. Group IID 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. L-alpha-1-palmitoyl-2-linoleoyl phosphatidylethanolamine is more efficiently hydrolyzed than the other phospholipids examined.
Gene Name:: PLA2G2D
Uniprot ID:: Q9UNK4
Molecular weight:: 16546.1

Only showing the first 10 proteins. There are 26 proteins in total.

Show all enzymes and transporters

Showing metabocard for LysoPC(O-18:0/0:0) (HMDB0011149)

MOL for HMDB0011149 (LysoPC(O-18:0/0:0))

3D MOL for HMDB0011149 (LysoPC(O-18:0/0:0))

3D SDF for HMDB0011149 (LysoPC(O-18:0/0:0))

3D-SDF for HMDB0011149 (LysoPC(O-18:0/0:0))

PDB for HMDB0011149 (LysoPC(O-18:0/0:0))

3D PDB for HMDB0011149 (LysoPC(O-18:0/0:0))

SMILES for HMDB0011149 (LysoPC(O-18:0/0:0))

INCHI for HMDB0011149 (LysoPC(O-18:0/0:0))

Structure for HMDB0011149 (LysoPC(O-18:0/0:0))

3D Structure for HMDB0011149 (LysoPC(O-18:0/0:0))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes