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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2012-09-08 14:59:46 UTC

Update Date

2022-11-30 19:04:14 UTC

HMDB ID

HMDB0029207

Secondary Accession Numbers

HMDB29207

Metabolite Identification

Common Name

LysoPC(6:0/0:0)

Description

Lysopc(6:0), also known as LPC(6:0/0:0) or 1-Caproyl-sn-glycero-3-phosphocholine, is classified as a member of the 1-acyl-sn-glycero-3-phosphocholines. 1-acyl-sn-glycero-3-phosphocholines are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphocholine. Lysopc(6:0) is considered to be a practically insoluble (in water) and a moderately acidic compound. Lysopc(6:0) is a glycerophosphocholine lipid molecule. Lysopc(6:0) can be found in urine. 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

HMDB0029207
     RDKit          3D
LysoPC(6:0/0:0)
 53 52  0  0  0  0  0  0  0  0999 V2000
    8.3707   -0.4109    1.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0896   -0.1663   -0.2981 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0733   -1.1621   -0.7831 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7852   -1.0537   -0.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1778    0.3269   -0.2361 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9033    0.3166    0.5417 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9141    0.0363    1.7677 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6817    0.6021   -0.0238 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4460    0.6039    0.6686 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4101    0.9364   -0.4178 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5362   -0.1007   -1.3701 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9785    0.8655    0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2734    1.8302    1.0646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8600    1.6990    1.6193 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.5150    3.0626    1.6238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8284    1.1355    3.1952 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.6871    0.6856    0.5611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5444    1.3763   -0.2810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2143    0.3478   -1.1746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9706   -0.6338   -0.4351 N   0  0  0  0  0  4  0  0  0  0  0  0
   -6.5964   -0.0411    0.7090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1231   -1.7526   -0.0999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0170   -1.1299   -1.3422 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3688    0.0211    1.4191 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5812    0.0720    1.8137 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3600   -1.5052    1.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8059    0.8752   -0.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0398   -0.3755   -0.8522 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4692   -2.2017   -0.6736 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8587   -0.9632   -1.8700 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9778   -1.2576    1.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0829   -1.8490   -0.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8540    1.1260    0.0986 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0125    0.4602   -1.3154 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1745   -0.3371    1.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4265    1.3903    1.4572 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6640    1.8883   -0.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3259   -0.5086   -1.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6840    0.8489   -0.7284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0714   -0.1229    0.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3070    1.9803    0.2244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9991    2.0711   -0.9608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4598   -0.2178   -1.7781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8838    0.8467   -1.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1188   -0.8464    1.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2731    0.7622    0.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8332    0.3887    1.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4333   -2.6810   -0.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0615   -1.5856   -0.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1926   -1.9586    0.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5745   -1.6929   -2.1667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7207   -1.7599   -0.7749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5174   -0.2414   -1.7708 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
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  6
 11 38  1  0
 12 39  1  0
 12 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
 19 44  1  0
 21 45  1  0
 21 46  1  0
 21 47  1  0
 22 48  1  0
 22 49  1  0
 22 50  1  0
 23 51  1  0
 23 52  1  0
 23 53  1  0
M  CHG  2  16  -1  20   1
M  END


  Mrv1652302102020392D          

 24 23  0  0  0  0            999 V2000
   23.1434   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8414   -5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0164   -3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4263   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1408   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8552   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5697   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7144   -5.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9999   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7131   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1421   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4276   -4.2868    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.2842   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4289   -4.6993    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   17.4276   -3.4618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2842   -5.5243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1585   -5.4138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9835   -3.9849    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   15.9987   -4.2868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2855   -5.1118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8565   -4.2868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5710   -4.6993    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   17.4276   -5.1118    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7118   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  9  8  1  0  0  0  0
 12 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13  7  1  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  3  1  0  0  0  0
 14  8  1  0  0  0  0
 12 15  1  6  0  0  0
 16 13  2  0  0  0  0
 19 10  1  0  0  0  0
 19 13  1  0  0  0  0
 20  9  1  0  0  0  0
 21 11  1  0  0  0  0
 22 17  2  0  0  0  0
 22 18  1  0  0  0  0
 22 20  1  0  0  0  0
 22 21  1  0  0  0  0
 12 23  1  6  0  0  0
  4 24  1  0  0  0  0
M  CHG  2  14   1  18  -1
M  END
> <DATABASE_ID>
HMDB0029207

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H30NO7P/c1-5-6-7-8-14(17)20-11-13(16)12-22-23(18,19)21-10-9-15(2,3)4/h13,16H,5-12H2,1-4H3/t13-/m1/s1

> <INCHI_KEY>
WDNDPXJAUNUOFK-CYBMUJFWSA-N

> <FORMULA>
C14H30NO7P

> <MOLECULAR_WEIGHT>
355.3643

> <EXACT_MASS>
355.175988831

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
37.153375009120424

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{[(2R)-3-(hexanoyloxy)-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium

> <ALOGPS_LOGP>
-1.90

> <JCHEM_LOGP>
-3.2529441731384123

> <ALOGPS_LOGS>
-2.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.655609236411621

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8553406136270887

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4040033707844755

> <JCHEM_POLAR_SURFACE_AREA>
105.12

> <JCHEM_REFRACTIVITY>
96.26369999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.20e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-{[(2R)-3-(hexanoyloxy)-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029207
     RDKit          3D
LysoPC(6:0/0:0)
 53 52  0  0  0  0  0  0  0  0999 V2000
    8.3707   -0.4109    1.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0896   -0.1663   -0.2981 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0733   -1.1621   -0.7831 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7852   -1.0537   -0.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1778    0.3269   -0.2361 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9033    0.3166    0.5417 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9141    0.0363    1.7677 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6817    0.6021   -0.0238 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4460    0.6039    0.6686 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4101    0.9364   -0.4178 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5362   -0.1007   -1.3701 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9785    0.8655    0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2734    1.8302    1.0646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8600    1.6990    1.6193 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.5150    3.0626    1.6238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8284    1.1355    3.1952 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.6871    0.6856    0.5611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5444    1.3763   -0.2810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2143    0.3478   -1.1746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9706   -0.6338   -0.4351 N   0  0  0  0  0  4  0  0  0  0  0  0
   -6.5964   -0.0411    0.7090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1231   -1.7526   -0.0999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0170   -1.1299   -1.3422 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3688    0.0211    1.4191 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5812    0.0720    1.8137 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3600   -1.5052    1.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8059    0.8752   -0.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0398   -0.3755   -0.8522 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4692   -2.2017   -0.6736 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8587   -0.9632   -1.8700 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9778   -1.2576    1.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0829   -1.8490   -0.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8540    1.1260    0.0986 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0125    0.4602   -1.3154 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1745   -0.3371    1.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4265    1.3903    1.4572 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6640    1.8883   -0.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3259   -0.5086   -1.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6840    0.8489   -0.7284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0714   -0.1229    0.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3070    1.9803    0.2244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9991    2.0711   -0.9608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4598   -0.2178   -1.7781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8838    0.8467   -1.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1188   -0.8464    1.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2731    0.7622    0.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8332    0.3887    1.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4333   -2.6810   -0.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0615   -1.5856   -0.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1926   -1.9586    0.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5745   -1.6929   -2.1667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7207   -1.7599   -0.7749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5174   -0.2414   -1.7708 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
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  6
 11 38  1  0
 12 39  1  0
 12 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
 19 44  1  0
 21 45  1  0
 21 46  1  0
 21 47  1  0
 22 48  1  0
 22 49  1  0
 22 50  1  0
 23 51  1  0
 23 52  1  0
 23 53  1  0
M  CHG  2  16  -1  20   1
M  END

HEADER    PROTEIN                                 10-FEB-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-FEB-20         0                                  
HETATM    1  C   UNK     0      43.201  -8.002   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      42.637 -10.106   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      41.097  -7.438   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      23.196  -8.772   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      24.529  -8.002   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.863  -8.772   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      27.197  -8.002   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      40.534  -9.542   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      39.200  -8.772   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      31.198  -8.772   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      33.865  -8.772   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      32.532  -8.002   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      28.531  -8.772   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      41.867  -8.772   0.000  0.00  0.00           N+1
HETATM   15  O   UNK     0      32.532  -6.462   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      28.531 -10.312   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      35.763 -10.106   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      37.303  -7.438   0.000  0.00  0.00           O-1
HETATM   19  O   UNK     0      29.864  -8.002   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      37.866  -9.542   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      35.199  -8.002   0.000  0.00  0.00           O+0
HETATM   22  P   UNK     0      36.533  -8.772   0.000  0.00  0.00           P+0
HETATM   23  H   UNK     0      32.532  -9.542   0.000  0.00  0.00           H+0
HETATM   24  C   UNK     0      21.862  -8.002   0.000  0.00  0.00           C+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3   14                                                            
CONECT    4    5   24                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6   13                                                       
CONECT    8    9   14                                                       
CONECT    9    8   20                                                       
CONECT   10   12   19                                                       
CONECT   11   12   21                                                       
CONECT   12   10   11   15   23                                             
CONECT   13    7   16   19                                                  
CONECT   14    1    2    3    8                                             
CONECT   15   12                                                            
CONECT   16   13                                                            
CONECT   17   22                                                            
CONECT   18   22                                                            
CONECT   19   10   13                                                       
CONECT   20    9   22                                                       
CONECT   21   11   22                                                       
CONECT   22   17   18   20   21                                             
CONECT   23   12                                                            
CONECT   24    4                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

COMPND    HMDB0029207
HETATM    1  C1  UNL     1       8.371  -0.411   1.186  1.00  0.00           C  
HETATM    2  C2  UNL     1       8.090  -0.166  -0.298  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.073  -1.162  -0.783  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.785  -1.054  -0.041  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.178   0.327  -0.236  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.903   0.317   0.542  1.00  0.00           C  
HETATM    7  O1  UNL     1       3.914   0.036   1.768  1.00  0.00           O  
HETATM    8  O2  UNL     1       2.682   0.602  -0.024  1.00  0.00           O  
HETATM    9  C7  UNL     1       1.446   0.604   0.669  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.410   0.936  -0.418  1.00  0.00           C  
HETATM   11  O3  UNL     1       0.536  -0.101  -1.370  1.00  0.00           O  
HETATM   12  C9  UNL     1      -0.979   0.865   0.113  1.00  0.00           C  
HETATM   13  O4  UNL     1      -1.273   1.830   1.065  1.00  0.00           O  
HETATM   14  P1  UNL     1      -2.860   1.699   1.619  1.00  0.00           P  
HETATM   15  O5  UNL     1      -3.515   3.063   1.624  1.00  0.00           O  
HETATM   16  O6  UNL     1      -2.828   1.136   3.195  1.00  0.00           O1-
HETATM   17  O7  UNL     1      -3.687   0.686   0.561  1.00  0.00           O  
HETATM   18  C10 UNL     1      -4.544   1.376  -0.281  1.00  0.00           C  
HETATM   19  C11 UNL     1      -5.214   0.348  -1.175  1.00  0.00           C  
HETATM   20  N1  UNL     1      -5.971  -0.634  -0.435  1.00  0.00           N1+
HETATM   21  C12 UNL     1      -6.596  -0.041   0.709  1.00  0.00           C  
HETATM   22  C13 UNL     1      -5.123  -1.753  -0.100  1.00  0.00           C  
HETATM   23  C14 UNL     1      -7.017  -1.130  -1.342  1.00  0.00           C  
HETATM   24  H1  UNL     1       9.369   0.021   1.419  1.00  0.00           H  
HETATM   25  H2  UNL     1       7.581   0.072   1.814  1.00  0.00           H  
HETATM   26  H3  UNL     1       8.360  -1.505   1.401  1.00  0.00           H  
HETATM   27  H4  UNL     1       7.806   0.875  -0.413  1.00  0.00           H  
HETATM   28  H5  UNL     1       9.040  -0.376  -0.852  1.00  0.00           H  
HETATM   29  H6  UNL     1       7.469  -2.202  -0.674  1.00  0.00           H  
HETATM   30  H7  UNL     1       6.859  -0.963  -1.870  1.00  0.00           H  
HETATM   31  H8  UNL     1       5.978  -1.258   1.047  1.00  0.00           H  
HETATM   32  H9  UNL     1       5.083  -1.849  -0.351  1.00  0.00           H  
HETATM   33  H10 UNL     1       5.854   1.126   0.099  1.00  0.00           H  
HETATM   34  H11 UNL     1       5.013   0.460  -1.315  1.00  0.00           H  
HETATM   35  H12 UNL     1       1.175  -0.337   1.139  1.00  0.00           H  
HETATM   36  H13 UNL     1       1.427   1.390   1.457  1.00  0.00           H  
HETATM   37  H14 UNL     1       0.664   1.888  -0.887  1.00  0.00           H  
HETATM   38  H15 UNL     1      -0.326  -0.509  -1.588  1.00  0.00           H  
HETATM   39  H16 UNL     1      -1.684   0.849  -0.728  1.00  0.00           H  
HETATM   40  H17 UNL     1      -1.071  -0.123   0.656  1.00  0.00           H  
HETATM   41  H18 UNL     1      -5.307   1.980   0.224  1.00  0.00           H  
HETATM   42  H19 UNL     1      -3.999   2.071  -0.961  1.00  0.00           H  
HETATM   43  H20 UNL     1      -4.460  -0.218  -1.778  1.00  0.00           H  
HETATM   44  H21 UNL     1      -5.884   0.847  -1.907  1.00  0.00           H  
HETATM   45  H22 UNL     1      -7.119  -0.846   1.293  1.00  0.00           H  
HETATM   46  H23 UNL     1      -7.273   0.762   0.399  1.00  0.00           H  
HETATM   47  H24 UNL     1      -5.833   0.389   1.397  1.00  0.00           H  
HETATM   48  H25 UNL     1      -5.433  -2.681  -0.640  1.00  0.00           H  
HETATM   49  H26 UNL     1      -4.062  -1.586  -0.333  1.00  0.00           H  
HETATM   50  H27 UNL     1      -5.193  -1.959   0.990  1.00  0.00           H  
HETATM   51  H28 UNL     1      -6.574  -1.693  -2.167  1.00  0.00           H  
HETATM   52  H29 UNL     1      -7.721  -1.760  -0.775  1.00  0.00           H  
HETATM   53  H30 UNL     1      -7.517  -0.241  -1.771  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27   28
CONECT    3    4   29   30
CONECT    4    5   31   32
CONECT    5    6   33   34
CONECT    6    7    7    8
CONECT    8    9
CONECT    9   10   35   36
CONECT   10   11   12   37
CONECT   11   38
CONECT   12   13   39   40
CONECT   13   14
CONECT   14   15   15   16   17
CONECT   17   18
CONECT   18   19   41   42
CONECT   19   20   43   44
CONECT   20   21   22   23
CONECT   21   45   46   47
CONECT   22   48   49   50
CONECT   23   51   52   53
END

HMDB0029207
     RDKit          3D
LysoPC(6:0/0:0)
 53 52  0  0  0  0  0  0  0  0999 V2000
    8.3707   -0.4109    1.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0896   -0.1663   -0.2981 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0733   -1.1621   -0.7831 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7852   -1.0537   -0.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1778    0.3269   -0.2361 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9033    0.3166    0.5417 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9141    0.0363    1.7677 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6817    0.6021   -0.0238 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4460    0.6039    0.6686 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4101    0.9364   -0.4178 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5362   -0.1007   -1.3701 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9785    0.8655    0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2734    1.8302    1.0646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8600    1.6990    1.6193 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.5150    3.0626    1.6238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8284    1.1355    3.1952 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.6871    0.6856    0.5611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5444    1.3763   -0.2810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2143    0.3478   -1.1746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9706   -0.6338   -0.4351 N   0  0  0  0  0  4  0  0  0  0  0  0
   -6.5964   -0.0411    0.7090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1231   -1.7526   -0.0999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0170   -1.1299   -1.3422 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3688    0.0211    1.4191 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5812    0.0720    1.8137 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3600   -1.5052    1.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8059    0.8752   -0.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0398   -0.3755   -0.8522 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4692   -2.2017   -0.6736 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8587   -0.9632   -1.8700 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9778   -1.2576    1.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0829   -1.8490   -0.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8540    1.1260    0.0986 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0125    0.4602   -1.3154 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1745   -0.3371    1.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4265    1.3903    1.4572 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6640    1.8883   -0.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3259   -0.5086   -1.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6840    0.8489   -0.7284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0714   -0.1229    0.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3070    1.9803    0.2244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9991    2.0711   -0.9608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4598   -0.2178   -1.7781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8838    0.8467   -1.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1188   -0.8464    1.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2731    0.7622    0.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8332    0.3887    1.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4333   -2.6810   -0.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0615   -1.5856   -0.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1926   -1.9586    0.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5745   -1.6929   -2.1667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7207   -1.7599   -0.7749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5174   -0.2414   -1.7708 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
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  6
 11 38  1  0
 12 39  1  0
 12 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
 19 44  1  0
 21 45  1  0
 21 46  1  0
 21 47  1  0
 22 48  1  0
 22 49  1  0
 22 50  1  0
 23 51  1  0
 23 52  1  0
 23 53  1  0
M  CHG  2  16  -1  20   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-Caproyl-sn-glycero-3-phosphocholine	ChEBI
LPC 6:0/0:0	ChEBI
LPC(6:0/0:0)	ChEBI
PC(6:0/0:0)	ChEBI
LysoPC a C6:0	HMDB
1-Caproylglycerophosphocholine	HMDB

Chemical Formula

C₁₄H₃₀NO₇P

Average Molecular Weight

355.3643

Monoisotopic Molecular Weight

355.175988831

IUPAC Name

(2-{[(2R)-3-(hexanoyloxy)-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-3-(hexanoyloxy)-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C14H30NO7P/c1-5-6-7-8-14(17)20-11-13(16)12-22-23(18,19)21-10-9-15(2,3)4/h13,16H,5-12H2,1-4H3/t13-/m1/s1

InChI Key

WDNDPXJAUNUOFK-CYBMUJFWSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphocholines

Direct Parent

1-acyl-sn-glycero-3-phosphocholines

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

1-O-acyl-sn-glycero-3-phosphocholine (CHEBI:78215 )
lysophosphatidylcholine 6:0 (CHEBI:78215 )
Monoacylglycerophosphocholines (LMGP01050062 )

Ontology

Urine (PMID: 24023812)

Cell

All cells and tissues (HMDB: HMDB0029207)

Cellular substructure

Cell membrane (PMID: 30845751)

Source

Endogenous

Endogenous (HMDB: HMDB0029207)

Process

Naturally occurring process

Biological process

Cellular process

Apoptosis (PMID: 30845751)

Role

Industrial application

Pharmaceutical industry

Biomarker

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.82 g/L	ALOGPS
logP	-1.9	ALOGPS
logP	-3.3	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	105.12 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	96.26 m³·mol⁻¹	ChemAxon
Polarizability	37.15 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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]+	177.458	30932474
DeepCCS	[M-H]-	175.1	30932474
DeepCCS	[M-2H]-	209.017	30932474
DeepCCS	[M+Na]+	183.959	30932474
AllCCS	[M+H]+	186.2	32859911
AllCCS	[M+H-H2O]+	183.9	32859911
AllCCS	[M+NH4]+	188.3	32859911
AllCCS	[M+Na]+	188.9	32859911
AllCCS	[M-H]-	188.6	32859911
AllCCS	[M+Na-2H]-	189.7	32859911
AllCCS	[M+HCOO]-	191.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.66 minutes	32390414
Predicted by Siyang on May 30, 2022	10.749 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.11 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	272.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1270.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	183.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	141.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	158.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	85.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	396.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	401.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	762.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	960.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	285.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1372.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	247.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	261.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	395.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	200.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	113.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
LysoPC(6:0/0:0)	[H][C@@](O)(COC(=O)CCCCC)COP([O-])(=O)OCC[N+](C)(C)C	3047.9	Standard polar	33892256
LysoPC(6:0/0:0)	[H][C@@](O)(COC(=O)CCCCC)COP([O-])(=O)OCC[N+](C)(C)C	2054.9	Standard non polar	33892256
LysoPC(6:0/0:0)	[H][C@@](O)(COC(=O)CCCCC)COP([O-])(=O)OCC[N+](C)(C)C	2282.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
LysoPC(6:0/0:0),1TMS,isomer #1	CCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O[Si](C)(C)C	2314.6	Semi standard non polar	33892256
LysoPC(6:0/0:0),1TBDMS,isomer #1	CCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C	2550.3	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(6:0/0:0) GC-MS (1 TMS) - 70eV, Positive	splash10-006t-9301000000-def15b9bb2adb386e754	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - LysoPC(6:0/0:0) GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - LysoPC(6:0/0:0) GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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(6:0/0:0) 10V, Positive-QTOF	splash10-0a4r-0009000000-10fb247752e5c17f78fb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(6:0/0:0) 20V, Positive-QTOF	splash10-053r-0906000000-b02b83d71b6fdcf372f0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(6:0/0:0) 40V, Positive-QTOF	splash10-0f8i-0914000000-08f27142c89c3bc3f16f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(6:0/0:0) 10V, Negative-QTOF	splash10-0udi-2209000000-919bda577ec456144319	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(6:0/0:0) 20V, Negative-QTOF	splash10-00kb-9500000000-b7c9e3805c642b021c37	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(6:0/0:0) 40V, Negative-QTOF	splash10-014i-0900000000-4dd9137b7ddff312abe4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(6:0/0:0) 10V, Positive-QTOF	splash10-03di-0009000000-6c8462dc74410c937b4d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(6:0/0:0) 20V, Positive-QTOF	splash10-0xr0-0109000000-1ba9a857e6c2b075917b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(6:0/0:0) 40V, Positive-QTOF	splash10-0umi-0903000000-d636fa9697823fc649c1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(6:0/0:0) 10V, Positive-QTOF	splash10-004i-0009000000-02b6629031c5a097fbfc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(6:0/0:0) 20V, Positive-QTOF	splash10-016r-0009000000-b5567f2a3e72a7c1fe1a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(6:0/0:0) 40V, Positive-QTOF	splash10-0fr2-0905000000-d3664585aedfb1c487d9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(6:0/0:0) 10V, Negative-QTOF	splash10-0006-0009000000-96d8aa54c1fd8a2c877d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(6:0/0:0) 20V, Negative-QTOF	splash10-014l-0907000000-a2d2180a0938856ad6dc	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPC(6:0/0:0) 40V, Negative-QTOF	splash10-014i-0933000000-c14196cb4490fe56fd20	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	0.0045 (0.0022-0.0074) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Not Available

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

FDB031400

KNApSAcK ID

Not Available

Chemspider ID

24823024

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13917464

PDB ID

Not Available

ChEBI ID

78215

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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.

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

Showing metabocard for LysoPC(6:0/0:0) (HMDB0029207)

MOL for HMDB0029207 (LysoPC(6:0/0:0))

3D MOL for HMDB0029207 (LysoPC(6:0/0:0))

3D SDF for HMDB0029207 (LysoPC(6:0/0:0))

3D-SDF for HMDB0029207 (LysoPC(6:0/0:0))

PDB for HMDB0029207 (LysoPC(6:0/0:0))

3D PDB for HMDB0029207 (LysoPC(6:0/0:0))

SMILES for HMDB0029207 (LysoPC(6:0/0:0))

INCHI for HMDB0029207 (LysoPC(6:0/0:0))

Structure for HMDB0029207 (LysoPC(6:0/0:0))

3D Structure for HMDB0029207 (LysoPC(6:0/0:0))

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes