MiMeDB: Showing metabocard for Lyso-PE(0:0/14:0) (MMDBc0045139)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 13:34:27 UTC

Update Date

2022-09-01 00:58:40 UTC

Metabolite ID

MMDBc0045139

Metabolite Identification

Common Name

Lyso-PE(0:0/14:0)

Description

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.Lyso-PE(0:0/14:0), in particular, consists of one tetradecanoyl chain. 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. Some LPLs serve important signaling functions such as lysophosphatidic acid. Lysophosphatidylethanolamines (LPEs) can function as plant growth regulators with several diverse uses. (LPEs) are approved for outdoor agricultural use to accelerate ripening and improve the quality of fresh produce.

Structure

MOL SDF PDB SMILES InChI

Lyso-PE(0:0/14:0)
  Mrv1652307071619212D          

 28 27  0  0  1  0            999 V2000
   16.9770    0.6882    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   16.2625    0.2757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5480    0.6882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8335    0.2757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0238    0.2597    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.2207    0.2753    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   14.0257    1.0849    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   14.0238   -0.5654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5533    0.7602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8388    0.3477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1243    0.7602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4098    0.3477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8388   -0.4773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6953    0.7602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6953    1.5316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9812    0.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2671    0.7602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5529    0.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8388    0.7602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1246    0.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4105    0.7602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6963    0.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9822    0.7602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2681    0.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5540    0.7602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8398    0.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1257    0.7602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4115    0.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  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
  5  7  1  0  0  0  0
  5  8  2  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 13  1  0  0  0  0
 11 12  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  CHG  3   1   1   6  -1   7  -1
M  END

Lyso-PE(0:0/14:0)
  Mrv1652307071619212D          

 28 27  0  0  1  0            999 V2000
   16.9770    0.6882    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   16.2625    0.2757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5480    0.6882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8335    0.2757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0238    0.2597    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.2207    0.2753    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   14.0257    1.0849    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   14.0238   -0.5654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5533    0.7602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8388    0.3477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1243    0.7602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4098    0.3477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8388   -0.4773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6953    0.7602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6953    1.5316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9812    0.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2671    0.7602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5529    0.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8388    0.7602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1246    0.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4105    0.7602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6963    0.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9822    0.7602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2681    0.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5540    0.7602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8398    0.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1257    0.7602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4115    0.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  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
  5  7  1  0  0  0  0
  5  8  2  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 13  1  0  0  0  0
 11 12  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  CHG  3   1   1   6  -1   7  -1
M  END
> <DATABASE_ID>
MMDBc0045139

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCCCCCCCCCCC(=O)OCC(O)C[O-]P([O-])(=O)OCC[NH3+]

> <INCHI_IDENTIFIER>
InChI=1S/C19H40NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-19(22)25-16-18(21)17-27-28(23,24)26-15-14-20/h18,21H,2-17,20H2,1H3,(H,23,24)/q-1

> <INCHI_KEY>
KWTVFPJDMXCNAB-UHFFFAOYSA-N

> <FORMULA>
C19H40NO7P

> <MOLECULAR_WEIGHT>
425.503

> <EXACT_MASS>
425.25478821

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
47.80657395477395

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(2-azaniumylethyl phosphono)oxido]-2-hydroxypropyl tetradecanoate

> <ALOGPS_LOGP>
1.66

> <ALOGPS_LOGS>
-4.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_POLAR_SURFACE_AREA>
132.76000000000002

> <JCHEM_REFRACTIVITY>
118.3816

> <JCHEM_ROTATABLE_BOND_COUNT>
21

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.85e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(2-ammonioethyl phosphonooxido)-2-hydroxypropyl tetradecanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-JUL-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Lyso-PE(0:0/14:0)                                 
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JUL-16         0                                  
HETATM    1  N   UNK     0      31.690   1.285   0.000  0.00  0.00           N+1
HETATM    2  C   UNK     0      30.357   0.515   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      29.023   1.285   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      27.689   0.515   0.000  0.00  0.00           O+0
HETATM    5  P   UNK     0      26.178   0.485   0.000  0.00  0.00           P+0
HETATM    6  O   UNK     0      24.679   0.514   0.000  0.00  0.00           O-1
HETATM    7  O   UNK     0      26.181   2.025   0.000  0.00  0.00           O-1
HETATM    8  O   UNK     0      26.178  -1.055   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      23.433   1.419   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.099   0.649   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      20.765   1.419   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      19.432   0.649   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      22.099  -0.891   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      18.098   1.419   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      18.098   2.859   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      16.765   0.648   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.432   1.419   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.099   0.648   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.766   1.419   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.433   0.648   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.100   1.419   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.767   0.648   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.433   1.419   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.100   0.648   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.767   1.419   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.434   0.648   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.101   1.419   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.768   0.648   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7    8                                             
CONECT    6    5    9                                                       
CONECT    7    5                                                            
CONECT    8    5                                                            
CONECT    9    6   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11   14                                                       
CONECT   13   10                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   54    0
END

Synonyms

Not Available

Molecular Formula

C₁₉H₄₀NO₇P

Average Mass

425.503

Monoisotopic Mass

425.25478821

IUPAC Name

3-[(2-azaniumylethyl phosphono)oxido]-2-hydroxypropyl tetradecanoate

Traditional Name

3-(2-ammonioethyl phosphonooxido)-2-hydroxypropyl tetradecanoate

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCC(=O)OCC(O)C[O-]P([O-])(=O)OCC[NH3+]

InChI Identifier

InChI=1S/C19H40NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-19(22)25-16-18(21)17-27-28(23,24)26-15-14-20/h18,21H,2-17,20H2,1H3,(H,23,24)/q-1

InChI Key

KWTVFPJDMXCNAB-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoethanolamines

Direct Parent

1-acyl-sn-glycero-3-phosphoethanolamines

Alternative Parents

Substituents

1-monoacyl-sn-glycero-3-phosphoethanolamine
Dialkyl phosphate
Fatty acid ester
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Secondary alcohol
Carboxylic acid ester
Amino acid or derivatives
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
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	0.0068 g/L	ALOGPS
logP	1.66	ALOGPS
logS	-4.9	ALOGPS
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	132.76 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	118.38 m³·mol⁻¹	ChemAxon
Polarizability	47.81 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	splash10-0a50-0091800000-b9b238601d0d57a744a0	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

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-PE(0:0/14:0) (MMDBc0045139)

MOL for #<Metabolite:0x00007fecf4879518>

3D MOL for #<Metabolite:0x00007fecf4879518>

3D SDF for #<Metabolite:0x00007fecf4879518>

3D-SDF for #<Metabolite:0x00007fecf4879518>

PDB for #<Metabolite:0x00007fecf4879518>

3D PDB for #<Metabolite:0x00007fecf4879518>

SMILES for #<Metabolite:0x00007fecf4879518>

INCHI for #<Metabolite:0x00007fecf4879518>

Structure for #<Metabolite:0x00007fecf4879518>

3D Structure for #<Metabolite:0x00007fecf4879518>