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Showing metabocard for LysoPC(0:0/18:2(9Z,12Z)) (HMDB0061700)

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enzymes (4) Show 4 proteins
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2014-04-16 20:46:07 UTC
Update Date2022-11-30 19:11:56 UTC
HMDB IDHMDB0061700
Secondary Accession Numbers
  • HMDB0062711
  • HMDB61700
  • HMDB62711
Metabolite Identification
Common NameLysoPC(0:0/18:2(9Z,12Z))
DescriptionLysoPC(0:0/18:2(9Z,12Z)) is a lysophosphatidylcholine, which is a lysophospholipid. The term 'lysophospholipid' (LPL) refers to any phospholipid that is missing one of its two O-acyl chains. Thus, LPLs have a free alcohol in either the sn-1 or sn-2 position. The prefix 'lyso-' comes from the fact that lysophospholipids were originally found to be hemolytic however it is now used to refer generally to phospholipids missing an acyl chain. LPLs are usually the result of phospholipase A-type enzymatic activity on regular phospholipids such as phosphatidylcholine or phosphatidic acid, although they can also be generated by the acylation of glycerophospholipids or the phosphorylation of monoacylglycerols. 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. There is also a phospholipase A1, which is able to cleave the sn-1 ester bond. Lysophosphatidylcholine has pro-inflammatory properties in vitro and it is known to be a pathological component of oxidized lipoproteins (LDL) in plasma and of atherosclerotic lesions. Recently, it has been found to have some functions in cell signalling, and specific receptors (coupled to G proteins) have been identified. It activates the specific phospholipase C that releases diacylglycerols and inositol triphosphate with resultant increases in intracellular Ca2+ and activation of protein kinase C. It also activates the mitogen-activated protein kinase in certain cell types. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) or C-2 (sn-2) position. LysoPC(0:0/18:2(9Z,12Z)), in particular, consists of one chain of linoleic acid at the C-2 position. 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
Data?1574356012
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0061700 (LysoPC(0:0/18:2(9Z,12Z)))

LysoPC(0:0/18:2(9Z,12Z))
  Mrv1652305062021422D          

 35 34  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
   20.5185   -7.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5185   -8.5377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8044   -7.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0903   -7.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3762   -7.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6621   -7.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9479   -7.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2338   -7.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5197   -7.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8056   -7.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9806   -7.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2665   -7.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5523   -7.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7273   -7.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0132   -7.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2991   -7.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5850   -7.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8709   -7.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1567   -7.3532    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
 10 12  1  0  0  0  0
 13 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  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
M  CHG  2   6   1  11  -1
M  END
Download

3D MOL for HMDB0061700 (LysoPC(0:0/18:2(9Z,12Z)))

HMDB0061700
     RDKit          3D
LysoPC(0:0/18:2(9Z,12Z))
 85 84  0  0  0  0  0  0  0  0999 V2000
   11.9969   -1.5520    1.2027 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0449   -0.2506    0.4664 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6857    0.2706    0.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7868   -0.8183   -0.5016 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6403   -0.1365   -1.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4856   -0.9472   -1.5624 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3144   -0.5179   -0.9848 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4882    0.6301   -0.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0119    1.9238   -0.4514 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0778    2.5824    0.1629 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3920    1.9876    1.3887 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9414    1.7675    0.9292 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0951    0.9781   -0.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7212    0.8139   -0.9624 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9601   -0.0256    0.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4145   -0.0657   -0.2963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0344   -0.9407   -1.3882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4515   -0.3254   -1.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0022    0.4292   -1.9699 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9824   -0.7447    0.0085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1235   -0.2779    0.5973 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0682    0.0407    1.9852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0041    1.0278    2.2748 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4039   -0.8670    0.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4955   -0.3450   -1.2356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8604    0.4805   -1.7275 P   0  0  0  0  0  5  0  0  0  0  0  0
   -7.3610   -0.0308   -3.0833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4009    2.1263   -2.0479 O   0  0  0  0  0  1  0  0  0  0  0  0
   -8.1675    0.4555   -0.6888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9362   -0.0164    0.6053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8600   -1.2119    0.7386 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2262   -0.8511    0.5869 N   0  0  0  0  0  4  0  0  0  0  0  0
  -10.5129    0.3116   -0.1131 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8886   -1.9773   -0.0276 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7034   -0.7724    2.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4311   -2.3130    0.4443 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9912   -1.9667    1.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6035   -1.5614    2.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4947    0.5185    1.1939 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6255   -0.2552   -0.4534 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5737    1.2171   -0.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1838    0.4414    1.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4318   -1.5033    0.2996 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3958   -1.3629   -1.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0611    0.2347   -2.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4470    0.8358   -0.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5534   -1.7511   -2.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4020   -0.9954   -1.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8311    0.2247    0.8409 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4415    0.6634    0.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5002    2.4232   -1.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6896    3.5254   -0.1854 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8572    1.1917    1.8893 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3844    2.8637    2.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4855    1.0832    1.6637 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3771    2.6763    0.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5678    0.0225   -0.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6570    1.5836   -1.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6064    0.4053   -1.9547 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2193    1.8324   -0.8860 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4196   -1.0968   -0.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1008    0.3045    1.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1557    0.1062    0.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6398    1.0127   -0.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6220   -0.8321   -2.3288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0354   -1.9572   -0.8801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2079    0.8264    0.0917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0060   -0.7340    2.7640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9943    0.6887    2.2231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2833    1.8829    1.8384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8839   -1.9810   -0.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1162   -1.3274    0.6037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5593    0.8338    1.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0458    0.1077    1.1102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6608   -1.8641    1.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6263   -1.9182   -0.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3773    0.0625   -1.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6203    0.5491    0.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9956    1.2410    0.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5894   -2.9234    0.4744 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9657   -1.7743   -0.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4255   -2.0344   -1.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8742   -1.1954    2.7017 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8223    0.2557    2.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5699   -1.4183    2.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  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
 21 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
  7 48  1  0
  8 49  1  0
  8 50  1  0
  9 51  1  0
 10 52  1  0
 11 53  1  0
 11 54  1  0
 12 55  1  0
 12 56  1  0
 13 57  1  0
 13 58  1  0
 14 59  1  0
 14 60  1  0
 15 61  1  0
 15 62  1  0
 16 63  1  0
 16 64  1  0
 17 65  1  0
 17 66  1  0
 21 67  1  6
 22 68  1  0
 22 69  1  0
 23 70  1  0
 24 71  1  0
 24 72  1  0
 30 73  1  0
 30 74  1  0
 31 75  1  0
 31 76  1  0
 33 77  1  0
 33 78  1  0
 33 79  1  0
 34 80  1  0
 34 81  1  0
 34 82  1  0
 35 83  1  0
 35 84  1  0
 35 85  1  0
M  CHG  2  28  -1  32   1
M  END
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3D SDF for HMDB0061700 (LysoPC(0:0/18:2(9Z,12Z)))

LysoPC(0:0/18:2(9Z,12Z))
  Mrv1652305062021422D          

 35 34  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
   20.5185   -7.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5185   -8.5377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8044   -7.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0903   -7.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3762   -7.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6621   -7.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9479   -7.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2338   -7.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5197   -7.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8056   -7.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9806   -7.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2665   -7.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5523   -7.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7273   -7.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0132   -7.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2991   -7.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5850   -7.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8709   -7.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1567   -7.3532    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
 10 12  1  0  0  0  0
 13 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  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
M  CHG  2   6   1  11  -1
M  END
> <DATABASE_ID>
HMDB0061700

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C26H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26(29)34-25(23-28)24-33-35(30,31)32-22-21-27(2,3)4/h9-10,12-13,25,28H,5-8,11,14-24H2,1-4H3/b10-9-,13-12-/t25-/m1/s1

> <INCHI_KEY>
LSUXCWJOIAWGOU-FTJOPAKQSA-N

> <FORMULA>
C26H50NO7P

> <MOLECULAR_WEIGHT>
519.66

> <EXACT_MASS>
519.332489952

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
58.91070981274229

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{[(2R)-3-hydroxy-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

> <ALOGPS_LOGP>
2.18

> <JCHEM_LOGP>
1.358036493528255

> <ALOGPS_LOGS>
-6.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.579258211672176

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8550617598182955

> <JCHEM_PKA_STRONGEST_BASIC>
-2.983758125699806

> <JCHEM_POLAR_SURFACE_AREA>
105.12

> <JCHEM_REFRACTIVITY>
153.7089

> <JCHEM_ROTATABLE_BOND_COUNT>
24

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.83e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-{[(2R)-3-hydroxy-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0061700 (LysoPC(0:0/18:2(9Z,12Z)))

HMDB0061700
     RDKit          3D
LysoPC(0:0/18:2(9Z,12Z))
 85 84  0  0  0  0  0  0  0  0999 V2000
   11.9969   -1.5520    1.2027 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0449   -0.2506    0.4664 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6857    0.2706    0.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7868   -0.8183   -0.5016 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6403   -0.1365   -1.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4856   -0.9472   -1.5624 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3144   -0.5179   -0.9848 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4882    0.6301   -0.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0119    1.9238   -0.4514 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0778    2.5824    0.1629 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3920    1.9876    1.3887 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9414    1.7675    0.9292 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0951    0.9781   -0.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7212    0.8139   -0.9624 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9601   -0.0256    0.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4515   -0.3254   -1.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.0682    0.0407    1.9852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0041    1.0278    2.2748 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4039   -0.8670    0.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4955   -0.3450   -1.2356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8604    0.4805   -1.7275 P   0  0  0  0  0  5  0  0  0  0  0  0
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   -6.4009    2.1263   -2.0479 O   0  0  0  0  0  1  0  0  0  0  0  0
   -8.1675    0.4555   -0.6888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9362   -0.0164    0.6053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8600   -1.2119    0.7386 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2262   -0.8511    0.5869 N   0  0  0  0  0  4  0  0  0  0  0  0
  -10.5129    0.3116   -0.1131 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8886   -1.9773   -0.0276 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7034   -0.7724    2.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4311   -2.3130    0.4443 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9912   -1.9667    1.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6035   -1.5614    2.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4947    0.5185    1.1939 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6255   -0.2552   -0.4534 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5737    1.2171   -0.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1838    0.4414    1.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4318   -1.5033    0.2996 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3958   -1.3629   -1.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0611    0.2347   -2.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4470    0.8358   -0.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5534   -1.7511   -2.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4020   -0.9954   -1.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8311    0.2247    0.8409 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4415    0.6634    0.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5002    2.4232   -1.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6896    3.5254   -0.1854 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8572    1.1917    1.8893 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3844    2.8637    2.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4855    1.0832    1.6637 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3771    2.6763    0.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5678    0.0225   -0.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6570    1.5836   -1.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6064    0.4053   -1.9547 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2193    1.8324   -0.8860 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4196   -1.0968   -0.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1008    0.3045    1.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1557    0.1062    0.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6398    1.0127   -0.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6220   -0.8321   -2.3288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0354   -1.9572   -0.8801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2079    0.8264    0.0917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0060   -0.7340    2.7640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9943    0.6887    2.2231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2833    1.8829    1.8384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8839   -1.9810   -0.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1162   -1.3274    0.6037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5593    0.8338    1.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0458    0.1077    1.1102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6608   -1.8641    1.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.3773    0.0625   -1.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.5894   -2.9234    0.4744 H   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.4255   -2.0344   -1.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8742   -1.1954    2.7017 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8223    0.2557    2.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5699   -1.4183    2.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  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
 21 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
  7 48  1  0
  8 49  1  0
  8 50  1  0
  9 51  1  0
 10 52  1  0
 11 53  1  0
 11 54  1  0
 12 55  1  0
 12 56  1  0
 13 57  1  0
 13 58  1  0
 14 59  1  0
 14 60  1  0
 15 61  1  0
 15 62  1  0
 16 63  1  0
 16 64  1  0
 17 65  1  0
 17 66  1  0
 21 67  1  6
 22 68  1  0
 22 69  1  0
 23 70  1  0
 24 71  1  0
 24 72  1  0
 30 73  1  0
 30 74  1  0
 31 75  1  0
 31 76  1  0
 33 77  1  0
 33 78  1  0
 33 79  1  0
 34 80  1  0
 34 81  1  0
 34 82  1  0
 35 83  1  0
 35 84  1  0
 35 85  1  0
M  CHG  2  28  -1  32   1
M  END
Download

PDB for HMDB0061700 (LysoPC(0:0/18:2(9Z,12Z)))

HEADER    PROTEIN                                 06-MAY-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: LysoPC(0:0/18:2(9Z,12Z))                          
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-20         0                                  
HETATM    1  P   UNK     0      43.614 -12.209   0.000  0.00  0.00           P+0
HETATM    2  O   UNK     0      43.614 -13.749   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      45.154 -12.209   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      46.487 -11.439   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      47.821 -12.209   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      49.155 -11.439   0.000  0.00  0.00           N+1
HETATM    7  C   UNK     0      50.488 -10.669   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      49.925 -12.773   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      48.385 -10.106   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      42.302 -12.187   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      43.614 -10.669   0.000  0.00  0.00           O-1
HETATM   12  C   UNK     0      40.969 -11.417   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      39.635 -12.187   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      38.301 -11.417   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      36.968 -12.187   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      39.635 -13.727   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      38.301 -14.497   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      38.301 -15.937   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      36.968 -13.726   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      35.635 -14.497   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      34.302 -13.726   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      32.969 -14.497   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      31.636 -13.726   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      30.303 -14.497   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      28.970 -13.726   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      27.637 -14.497   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      26.097 -14.497   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      24.764 -13.726   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      23.431 -14.497   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      21.891 -14.497   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      20.558 -13.726   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      19.225 -14.497   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      17.892 -13.726   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      16.559 -14.497   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      15.226 -13.726   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                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   68    0
END
Download

3D PDB for HMDB0061700 (LysoPC(0:0/18:2(9Z,12Z)))

COMPND    HMDB0061700
HETATM    1  C1  UNL     1      11.997  -1.552   1.203  1.00  0.00           C  
HETATM    2  C2  UNL     1      12.045  -0.251   0.466  1.00  0.00           C  
HETATM    3  C3  UNL     1      10.686   0.271   0.176  1.00  0.00           C  
HETATM    4  C4  UNL     1       9.787  -0.818  -0.502  1.00  0.00           C  
HETATM    5  C5  UNL     1       8.640  -0.136  -1.103  1.00  0.00           C  
HETATM    6  C6  UNL     1       7.486  -0.947  -1.562  1.00  0.00           C  
HETATM    7  C7  UNL     1       6.314  -0.518  -0.985  1.00  0.00           C  
HETATM    8  C8  UNL     1       6.488   0.630  -0.055  1.00  0.00           C  
HETATM    9  C9  UNL     1       6.012   1.924  -0.451  1.00  0.00           C  
HETATM   10  C10 UNL     1       5.078   2.582   0.163  1.00  0.00           C  
HETATM   11  C11 UNL     1       4.392   1.988   1.389  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.941   1.767   0.929  1.00  0.00           C  
HETATM   13  C13 UNL     1       3.095   0.978  -0.416  1.00  0.00           C  
HETATM   14  C14 UNL     1       1.721   0.814  -0.962  1.00  0.00           C  
HETATM   15  C15 UNL     1       0.960  -0.026   0.088  1.00  0.00           C  
HETATM   16  C16 UNL     1      -0.415  -0.066  -0.296  1.00  0.00           C  
HETATM   17  C17 UNL     1      -1.034  -0.941  -1.388  1.00  0.00           C  
HETATM   18  C18 UNL     1      -2.451  -0.325  -1.220  1.00  0.00           C  
HETATM   19  O1  UNL     1      -3.002   0.429  -1.970  1.00  0.00           O  
HETATM   20  O2  UNL     1      -2.982  -0.745   0.008  1.00  0.00           O  
HETATM   21  C19 UNL     1      -4.123  -0.278   0.597  1.00  0.00           C  
HETATM   22  C20 UNL     1      -4.068   0.041   1.985  1.00  0.00           C  
HETATM   23  O3  UNL     1      -3.004   1.028   2.275  1.00  0.00           O  
HETATM   24  C21 UNL     1      -5.404  -0.867   0.015  1.00  0.00           C  
HETATM   25  O4  UNL     1      -5.496  -0.345  -1.236  1.00  0.00           O  
HETATM   26  P1  UNL     1      -6.860   0.481  -1.727  1.00  0.00           P  
HETATM   27  O5  UNL     1      -7.361  -0.031  -3.083  1.00  0.00           O  
HETATM   28  O6  UNL     1      -6.401   2.126  -2.048  1.00  0.00           O1-
HETATM   29  O7  UNL     1      -8.167   0.455  -0.689  1.00  0.00           O  
HETATM   30  C22 UNL     1      -7.936  -0.016   0.605  1.00  0.00           C  
HETATM   31  C23 UNL     1      -8.860  -1.212   0.739  1.00  0.00           C  
HETATM   32  N1  UNL     1     -10.226  -0.851   0.587  1.00  0.00           N1+
HETATM   33  C24 UNL     1     -10.513   0.312  -0.113  1.00  0.00           C  
HETATM   34  C25 UNL     1     -10.889  -1.977  -0.028  1.00  0.00           C  
HETATM   35  C26 UNL     1     -10.703  -0.772   2.002  1.00  0.00           C  
HETATM   36  H1  UNL     1      12.431  -2.313   0.444  1.00  0.00           H  
HETATM   37  H2  UNL     1      10.991  -1.967   1.387  1.00  0.00           H  
HETATM   38  H3  UNL     1      12.604  -1.561   2.108  1.00  0.00           H  
HETATM   39  H4  UNL     1      12.495   0.519   1.194  1.00  0.00           H  
HETATM   40  H5  UNL     1      12.626  -0.255  -0.453  1.00  0.00           H  
HETATM   41  H6  UNL     1      10.574   1.217  -0.340  1.00  0.00           H  
HETATM   42  H7  UNL     1      10.184   0.441   1.199  1.00  0.00           H  
HETATM   43  H8  UNL     1       9.432  -1.503   0.300  1.00  0.00           H  
HETATM   44  H9  UNL     1      10.396  -1.363  -1.249  1.00  0.00           H  
HETATM   45  H10 UNL     1       9.061   0.235  -2.208  1.00  0.00           H  
HETATM   46  H11 UNL     1       8.447   0.836  -0.681  1.00  0.00           H  
HETATM   47  H12 UNL     1       7.553  -1.751  -2.218  1.00  0.00           H  
HETATM   48  H13 UNL     1       5.402  -0.995  -1.233  1.00  0.00           H  
HETATM   49  H14 UNL     1       5.831   0.225   0.841  1.00  0.00           H  
HETATM   50  H15 UNL     1       7.441   0.663   0.487  1.00  0.00           H  
HETATM   51  H16 UNL     1       6.500   2.423  -1.329  1.00  0.00           H  
HETATM   52  H17 UNL     1       4.690   3.525  -0.185  1.00  0.00           H  
HETATM   53  H18 UNL     1       4.857   1.192   1.889  1.00  0.00           H  
HETATM   54  H19 UNL     1       4.384   2.864   2.145  1.00  0.00           H  
HETATM   55  H20 UNL     1       2.485   1.083   1.664  1.00  0.00           H  
HETATM   56  H21 UNL     1       2.377   2.676   0.837  1.00  0.00           H  
HETATM   57  H22 UNL     1       3.568   0.023  -0.143  1.00  0.00           H  
HETATM   58  H23 UNL     1       3.657   1.584  -1.154  1.00  0.00           H  
HETATM   59  H24 UNL     1       1.606   0.405  -1.955  1.00  0.00           H  
HETATM   60  H25 UNL     1       1.219   1.832  -0.886  1.00  0.00           H  
HETATM   61  H26 UNL     1       1.420  -1.097  -0.026  1.00  0.00           H  
HETATM   62  H27 UNL     1       1.101   0.305   1.105  1.00  0.00           H  
HETATM   63  H28 UNL     1      -1.156   0.106   0.540  1.00  0.00           H  
HETATM   64  H29 UNL     1      -0.640   1.013  -0.861  1.00  0.00           H  
HETATM   65  H30 UNL     1      -0.622  -0.832  -2.329  1.00  0.00           H  
HETATM   66  H31 UNL     1      -1.035  -1.957  -0.880  1.00  0.00           H  
HETATM   67  H32 UNL     1      -4.208   0.826   0.092  1.00  0.00           H  
HETATM   68  H33 UNL     1      -4.006  -0.734   2.764  1.00  0.00           H  
HETATM   69  H34 UNL     1      -4.994   0.689   2.223  1.00  0.00           H  
HETATM   70  H35 UNL     1      -3.283   1.883   1.838  1.00  0.00           H  
HETATM   71  H36 UNL     1      -4.884  -1.981  -0.324  1.00  0.00           H  
HETATM   72  H37 UNL     1      -6.116  -1.327   0.604  1.00  0.00           H  
HETATM   73  H38 UNL     1      -8.559   0.834   1.212  1.00  0.00           H  
HETATM   74  H39 UNL     1      -7.046   0.108   1.110  1.00  0.00           H  
HETATM   75  H40 UNL     1      -8.661  -1.864   1.564  1.00  0.00           H  
HETATM   76  H41 UNL     1      -8.626  -1.918  -0.170  1.00  0.00           H  
HETATM   77  H42 UNL     1     -10.377   0.063  -1.193  1.00  0.00           H  
HETATM   78  H43 UNL     1     -11.620   0.549   0.039  1.00  0.00           H  
HETATM   79  H44 UNL     1      -9.996   1.241   0.053  1.00  0.00           H  
HETATM   80  H45 UNL     1     -10.589  -2.923   0.474  1.00  0.00           H  
HETATM   81  H46 UNL     1     -11.966  -1.774  -0.066  1.00  0.00           H  
HETATM   82  H47 UNL     1     -10.426  -2.034  -1.060  1.00  0.00           H  
HETATM   83  H48 UNL     1      -9.874  -1.195   2.702  1.00  0.00           H  
HETATM   84  H49 UNL     1     -10.822   0.256   2.352  1.00  0.00           H  
HETATM   85  H50 UNL     1     -11.570  -1.418   2.186  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    7   47
CONECT    7    8   48
CONECT    8    9   49   50
CONECT    9   10   10   51
CONECT   10   11   52
CONECT   11   12   53   54
CONECT   12   13   55   56
CONECT   13   14   57   58
CONECT   14   15   59   60
CONECT   15   16   61   62
CONECT   16   17   63   64
CONECT   17   18   65   66
CONECT   18   19   19   20
CONECT   20   21
CONECT   21   22   24   67
CONECT   22   23   68   69
CONECT   23   70
CONECT   24   25   71   72
CONECT   25   26
CONECT   26   27   27   28   29
CONECT   29   30
CONECT   30   31   73   74
CONECT   31   32   75   76
CONECT   32   33   34   35
CONECT   33   77   78   79
CONECT   34   80   81   82
CONECT   35   83   84   85
END
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SMILES for HMDB0061700 (LysoPC(0:0/18:2(9Z,12Z)))

CCCCC\C=C/C\C=C/CCCCCCCC(=O)O[C@H](CO)COP([O-])(=O)OCC[N+](C)(C)C
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INCHI for HMDB0061700 (LysoPC(0:0/18:2(9Z,12Z)))

InChI=1S/C26H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26(29)34-25(23-28)24-33-35(30,31)32-22-21-27(2,3)4/h9-10,12-13,25,28H,5-8,11,14-24H2,1-4H3/b10-9-,13-12-/t25-/m1/s1
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2-(9Z,12Z-Octadecadienoyl)-sn-glycero-3-phosphocholineChEBI
2-LinoleoyllysophosphatidylcholineChEBI
LPC[0:0/18:2(omega-6)]ChEBI
2-Linoleoyl-GPCHMDB
2-Linoleoyl-lysophosphatidylcholineHMDB
2-Linoleoyl-sn-glycero-3-phosphocholineHMDB
2-Linoleoyl-sn-glycero-3-phosphorylcholineHMDB
GPC(0:0/18:2(9Z,12Z))HMDB
GPC(0:0/18:2n6)HMDB
GPC(0:0/18:2w6)HMDB
GPC(18:2(9Z,12Z))HMDB
GPC(18:2)HMDB
GPC(18:2n6)HMDB
GPC(18:2w6)HMDB
LPC(0:0/18:2(9Z,12Z))HMDB
LPC(0:0/18:2n6)HMDB
LPC(0:0/18:2w6)HMDB
LPC(18:2(9Z,12Z))HMDB
LPC(18:2)HMDB
LPC(18:2n6)HMDB
LPC(18:2w6)HMDB
LysoPC(0:0/18:2(9Z,12Z))HMDB
LysoPC(0:0/18:2n6)HMDB
LysoPC(0:0/18:2w6)HMDB
LysoPC(18:2(9Z,12Z))HMDB
LysoPC(18:2)HMDB
LysoPC(18:2n6)HMDB
LysoPC(18:2w6)HMDB
Lysophosphatidylcholine(0:0/18:2(9Z,12Z))HMDB
Lysophosphatidylcholine(0:0/18:2n6)HMDB
Lysophosphatidylcholine(0:0/18:2w6)HMDB
Lysophosphatidylcholine(18:2(9Z,12Z))HMDB
Lysophosphatidylcholine(18:2)HMDB
Lysophosphatidylcholine(18:2n6)HMDB
Lysophosphatidylcholine(18:2w6)HMDB
Chemical FormulaC26H50NO7P
Average Molecular Weight519.66
Monoisotopic Molecular Weight519.332489952
IUPAC Name(2-{[(2R)-3-hydroxy-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-3-hydroxy-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry Number27304-12-7
SMILES
CCCCC\C=C/C\C=C/CCCCCCCC(=O)O[C@H](CO)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C26H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26(29)34-25(23-28)24-33-35(30,31)32-22-21-27(2,3)4/h9-10,12-13,25,28H,5-8,11,14-24H2,1-4H3/b10-9-,13-12-/t25-/m1/s1
InChI KeyLSUXCWJOIAWGOU-FTJOPAKQSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-2 position, and linked at position 3 to a phosphocholine.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct Parent2-acyl-sn-glycero-3-phosphocholines
Alternative Parents
Substituents
  • 2-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
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary alcohol
  • Carbonyl group
  • Organic salt
  • Amine
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Health effect
Disposition
Biological location
Process
Naturally occurring process
Role
Industrial application
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00033 g/LALOGPS
logP2.18ALOGPS
logP1.36ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area105.12 ŲChemAxon
Rotatable Bond Count24ChemAxon
Refractivity153.71 m³·mol⁻¹ChemAxon
Polarizability58.91 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+241.88830932474
DeepCCS[M-H]-238.62830932474
DeepCCS[M-2H]-272.88330932474
DeepCCS[M+Na]+249.38530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LysoPC(0:0/18:2(9Z,12Z))CCCCC\C=C/C\C=C/CCCCCCCC(=O)O[C@H](CO)COP([O-])(=O)OCC[N+](C)(C)C3641.0Standard polar33892256
LysoPC(0:0/18:2(9Z,12Z))CCCCC\C=C/C\C=C/CCCCCCCC(=O)O[C@H](CO)COP([O-])(=O)OCC[N+](C)(C)C3003.3Standard non polar33892256
LysoPC(0:0/18:2(9Z,12Z))CCCCC\C=C/C\C=C/CCCCCCCC(=O)O[C@H](CO)COP([O-])(=O)OCC[N+](C)(C)C3441.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
LysoPC(0:0/18:2(9Z,12Z)),1TMS,isomer #1CCCCC/C=C\C/C=C\CCCCCCCC(=O)O[C@H](CO[Si](C)(C)C)COP(=O)([O-])OCC[N+](C)(C)C3490.8Semi standard non polar33892256
LysoPC(0:0/18:2(9Z,12Z)),1TBDMS,isomer #1CCCCC/C=C\C/C=C\CCCCCCCC(=O)O[C@H](CO[Si](C)(C)C(C)(C)C)COP(=O)([O-])OCC[N+](C)(C)C3717.7Semi standard non polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(0:0/18:2(9Z,12Z)) 10V, Negative-QTOFsplash10-014i-0000090000-fd2faf599108994080042021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(0:0/18:2(9Z,12Z)) 20V, Negative-QTOFsplash10-00or-0090160000-8dc7815b750f313489492021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(0:0/18:2(9Z,12Z)) 40V, Negative-QTOFsplash10-004i-7290200000-789915f7abc186be71362021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(0:0/18:2(9Z,12Z)) 10V, Positive-QTOFsplash10-00di-0200190000-59d0b75344c55aad66522021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(0:0/18:2(9Z,12Z)) 20V, Positive-QTOFsplash10-001i-3900010000-dbe4c5bbf0b71dc22cd12021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(0:0/18:2(9Z,12Z)) 40V, Positive-QTOFsplash10-00ei-7900000000-083bbefc61c291236ef72021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID30785783
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound71768169
PDB IDNot Available
ChEBI ID76084
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
  10. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

Enzyme Details
1. Free fatty acid receptor 1
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for medium and long chain saturated and unsaturated fatty acids. Binding of the ligand increase intracellular calcium concentration and amplify glucose-stimulated insulin secretion. The activity of this receptor is mediated by G- proteins that activate phospholipase C. Seems to act through a G(q) and G(i)-mediated pathway
Gene Name:
FFAR1
Uniprot ID:
O14842
Molecular weight:
31456.6
Enzyme Details
2. Glucose-dependent insulinotropic receptor
General function:
Not Available
Specific function:
Receptor for the endogenous fatty-acid ethanolamide oleoylethanolamide (OEA) and lysophosphatidylcholine (LPC). Functions as a glucose-dependent insulinotropic receptor. The activity of this receptor is mediated by G proteins which activate adenylate cyclase. Seems to act through a G(s) mediated pathway.
Gene Name:
GPR119
Uniprot ID:
Q8TDV5
Molecular weight:
36888.36
Enzyme Details
3. G-protein coupled receptor 55
General function:
Not Available
Specific function:
May be involved in hyperalgesia associated with inflammatory and neuropathic pain. Receptor for L-alpha-lysophosphatidylinositol (LPI). LPI induces Ca2+ release from intracellular stores via the heterotrimeric G protein GNA13 and RHOA. Putative cannabinoid receptor. May play a role in bone physiology by regulating osteoclast number and function.
Gene Name:
GPR55
Uniprot ID:
Q9Y2T6
Molecular weight:
36.0
Enzyme Details
4. G-protein coupled receptor 4
General function:
Not Available
Specific function:
Proton-sensing G-protein coupled receptor couples to multiple intracellular signaling pathways, including GNAS/cAMP, GNAQ/phospholipase C (PLC), and GNA12/GNA13/Rho pathways. Acidosis-induced GPR4 activation increases paracellular gap formation and permeability of vascular endothelial cells through the GNA12/GNA13/Rho GTPase signaling pathway. In the brain may mediate central respiratory sensitivity to CO2H+.
Gene Name:
GPR4
Uniprot ID:
P46093
Molecular weight:
40.0