MiMeDB: Showing metabocard for Lyso-PC(16:1(11Z)/0:0) (MMDBc0045124)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 13:33:43 UTC

Update Date

2022-09-01 00:58:29 UTC

Metabolite ID

MMDBc0045124

Metabolite Identification

Common Name

Lyso-PC(16:1(11Z)/0:0)

Description

Lyso-PC(16:1(11Z)/0:0) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. Lyso-PC(16:1(11Z)/0:0), in particular, consists of one 11Z-hexadecenoyl chain. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) position. Fatty acids containing 16, 18 and 20 carbons are the most common. LysoPC(20:3(5Z,8Z,11Z)), in particular, consists of one chain of mead acid at the C-1 position. The mead acid moiety is derived from fish oils, liver and kidney. 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.

Structure

MOL SDF PDB SMILES InChI

Lyso-PC(16:1(11Z)/0:0)
  Mrv1652307071619212D          

 33 32  0  0  1  0            999 V2000
   23.3650   -6.5409    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   23.3650   -7.3659    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   24.1900   -6.5409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9045   -6.1284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6190   -6.5409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3335   -6.1284    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   27.0480   -5.7159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7460   -6.8429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9210   -5.4140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6626   -6.5290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3650   -5.7159    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   21.9481   -6.1165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2336   -6.5290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5191   -6.1165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8046   -6.5290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2336   -7.3540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0901   -6.1165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0901   -5.3451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3760   -6.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6619   -6.1165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9477   -6.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2336   -6.1165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5194   -6.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8053   -6.1165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0911   -6.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3770   -6.1165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6629   -6.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9488   -6.1165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1237   -6.1165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4096   -6.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6954   -6.1165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9813   -6.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2672   -6.1165    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
  1 10  1  0  0  0  0
  1 11  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
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 16  1  0  0  0  0
 14 15  1  0  0  0  0
 15 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  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  CHG  3   2  -1   6   1  11  -1
M  END

Lyso-PC(16:1(11Z)/0:0)
  Mrv1652307071619212D          

 33 32  0  0  1  0            999 V2000
   23.3650   -6.5409    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   23.3650   -7.3659    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   24.1900   -6.5409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9045   -6.1284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6190   -6.5409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3335   -6.1284    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   27.0480   -5.7159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7460   -6.8429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9210   -5.4140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6626   -6.5290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3650   -5.7159    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   21.9481   -6.1165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2336   -6.5290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5191   -6.1165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8046   -6.5290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2336   -7.3540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0901   -6.1165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0901   -5.3451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3760   -6.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6619   -6.1165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9477   -6.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2336   -6.1165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5194   -6.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8053   -6.1165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0911   -6.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3770   -6.1165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6629   -6.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9488   -6.1165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1237   -6.1165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4096   -6.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6954   -6.1165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9813   -6.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2672   -6.1165    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
  1 10  1  0  0  0  0
  1 11  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
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 16  1  0  0  0  0
 14 15  1  0  0  0  0
 15 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  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  CHG  3   2  -1   6   1  11  -1
M  END
> <DATABASE_ID>
MMDBc0045124

> <DATABASE_NAME>
MIME

> <SMILES>
CCCC\C=C/CCCCCCCCCC(=O)OCC(O)COP([O-])(=[O-])OCC[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C24H48NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-24(27)30-21-23(26)22-32-33(28,29)31-20-19-25(2,3)4/h8-9,23,26H,5-7,10-22H2,1-4H3/q-1/b9-8-

> <INCHI_KEY>
FZWKRKWEAXZBKJ-HJWRWDBZSA-N

> <FORMULA>
C24H48NO7P

> <MOLECULAR_WEIGHT>
493.622

> <EXACT_MASS>
493.317388468

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
56.683299063043144

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{2-[({3-[(11Z)-hexadec-11-enoyloxy]-2-hydroxypropoxy}(-lambda3-oxidanidylidene)oxido-lambda5-phosphanyl)oxy]ethyl}trimethylazanium

> <ALOGPS_LOGP>
1.90

> <ALOGPS_LOGS>
-6.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_POLAR_SURFACE_AREA>
105.12

> <JCHEM_REFRACTIVITY>
143.3903

> <JCHEM_ROTATABLE_BOND_COUNT>
23

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.43e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{2-[({3-[(11Z)-hexadec-11-enoyloxy]-2-hydroxypropoxy}(-lambda3-oxidanidylidene)oxido-lambda5-phosphanyl)oxy]ethyl}trimethylazanium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-JUL-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Lyso-PC(16:1(11Z)/0:0)                            
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JUL-16         0                                  
HETATM    1  P   UNK     0      43.615 -12.210   0.000  0.00  0.00           P+0
HETATM    2  O   UNK     0      43.615 -13.750   0.000  0.00  0.00           O-1
HETATM    3  O   UNK     0      45.155 -12.210   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      46.488 -11.440   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      47.822 -12.210   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      49.156 -11.440   0.000  0.00  0.00           N+1
HETATM    7  C   UNK     0      50.490 -10.670   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      49.926 -12.773   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      48.386 -10.106   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      42.303 -12.187   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      43.615 -10.670   0.000  0.00  0.00           O-1
HETATM   12  C   UNK     0      40.970 -11.417   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      39.636 -12.187   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      38.302 -11.417   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      36.969 -12.187   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      39.636 -13.728   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      35.635 -11.417   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      35.635  -9.977   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      34.302 -12.189   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      32.969 -11.417   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      31.636 -12.189   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      30.303 -11.417   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      28.970 -12.189   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      27.637 -11.417   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      26.303 -12.189   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      24.970 -11.417   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      23.637 -12.189   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      22.304 -11.417   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      20.764 -11.417   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      19.431 -12.189   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      18.098 -11.417   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      16.765 -12.189   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      15.432 -11.417   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   10   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14   17                                                       
CONECT   16   13                                                            
CONECT   17   15   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                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   64    0
END

Synonyms

Not Available

Molecular Formula

C₂₄H₄₈NO₇P

Average Mass

493.622

Monoisotopic Mass

493.317388468

IUPAC Name

{2-[({3-[(11Z)-hexadec-11-enoyloxy]-2-hydroxypropoxy}(-lambda3-oxidanidylidene)oxido-lambda5-phosphanyl)oxy]ethyl}trimethylazanium

Traditional Name

{2-[({3-[(11Z)-hexadec-11-enoyloxy]-2-hydroxypropoxy}(-lambda3-oxidanidylidene)oxido-lambda5-phosphanyl)oxy]ethyl}trimethylazanium

CAS Registry Number

Not Available

SMILES

CCCC\C=C/CCCCCCCCCC(=O)OCC(O)COP([O-])(=[O-])OCC[N+](C)(C)C

InChI Identifier

InChI=1S/C24H48NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-24(27)30-21-23(26)22-32-33(28,29)31-20-19-25(2,3)4/h8-9,23,26H,5-7,10-22H2,1-4H3/q-1/b9-8-

InChI Key

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.00044 g/L	ALOGPS
logP	1.9	ALOGPS
logS	-6.1	ALOGPS
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	105.12 Å²	ChemAxon
Rotatable Bond Count	23	ChemAxon
Refractivity	143.39 m³·mol⁻¹	ChemAxon
Polarizability	56.68 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0200900000-f256dad5776e4f384900	2016-09-19	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

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DrugBank ID

Not Available

Phenol Explorer Compound ID

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FooDB ID

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KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

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Wikipedia Link

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METLIN ID

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PubChem Compound

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PDB ID

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ChEBI ID

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Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Rattray JB, Schibeci A, Kidby DK: Lipids of yeasts. Bacteriol Rev. 1975 Sep;39(3):197-231. doi: 10.1128/br.39.3.197-231.1975. [PubMed:240350 ]

Showing metabocard for Lyso-PC(16:1(11Z)/0:0) (MMDBc0045124)

MOL for #<Metabolite:0x00007fecda042350>

3D MOL for #<Metabolite:0x00007fecda042350>

3D SDF for #<Metabolite:0x00007fecda042350>

3D-SDF for #<Metabolite:0x00007fecda042350>

PDB for #<Metabolite:0x00007fecda042350>

3D PDB for #<Metabolite:0x00007fecda042350>

SMILES for #<Metabolite:0x00007fecda042350>

INCHI for #<Metabolite:0x00007fecda042350>

Structure for #<Metabolite:0x00007fecda042350>

3D Structure for #<Metabolite:0x00007fecda042350>