MiMeDB: Showing metabocard for LysoPE(12:0/0:0) (MMDBc0060347)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2023-02-09 19:27:00 UTC

Update Date

2023-02-09 19:27:00 UTC

Metabolite ID

MMDBc0060347

Metabolite Identification

Common Name

LysoPE(12:0/0:0)

Description

PE(12:0/0:0) is a phosphatidylethanolamine. It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PE(12:0/0:0), in particular, consists of two dodecanoyl chains at positions C-1 and C-2. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS.

Structure

MOL SDF PDB SMILES InChI

  Mrv0541 10181208532D          

 26 25  0  0  1  0            999 V2000
    1.7092    4.2868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4237    3.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1382    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8526    3.8743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5671    4.2868    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.9796    3.5724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1546    5.0013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2816    4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9961    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7105    4.6993    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4250    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1395    4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8539    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8539    3.4618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5684    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2829    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9974    4.6993    0.0000 C   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
   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
   15.2842    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9987    4.2868    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
    6.7105    5.5243    0.0000 O   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  2  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 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
 10 26  1  6  0  0  0
M  END

  Mrv0541 10181208532D          

 26 25  0  0  1  0            999 V2000
    1.7092    4.2868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4237    3.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1382    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8526    3.8743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5671    4.2868    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.9796    3.5724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1546    5.0013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2816    4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9961    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7105    4.6993    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4250    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1395    4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8539    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8539    3.4618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5684    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2829    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9974    4.6993    0.0000 C   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
   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
   15.2842    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9987    4.2868    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
    6.7105    5.5243    0.0000 O   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  2  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 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
 10 26  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0060347

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCCCCCCCCC(=O)OC[C@@H](O)COP(O)(=O)OCCN

> <INCHI_IDENTIFIER>
InChI=1S/C17H36NO7P/c1-2-3-4-5-6-7-8-9-10-11-17(20)23-14-16(19)15-25-26(21,22)24-13-12-18/h16,19H,2-15,18H2,1H3,(H,21,22)/t16-/m1/s1

> <INCHI_KEY>
IZDRGPDUDLWAGR-MRXNPFEDSA-N

> <FORMULA>
C17H36NO7P

> <MOLECULAR_WEIGHT>
397.444

> <EXACT_MASS>
397.222939023

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
43.39010761782851

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2-aminoethoxy)[(2R)-3-(dodecanoyloxy)-2-hydroxypropoxy]phosphinic acid

> <ALOGPS_LOGP>
2.01

> <JCHEM_LOGP>
1.7515867664756657

> <ALOGPS_LOGS>
-3.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.655705215902849

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8690837557474262

> <JCHEM_PKA_STRONGEST_BASIC>
9.999833383834863

> <JCHEM_POLAR_SURFACE_AREA>
128.31

> <JCHEM_REFRACTIVITY>
99.0085

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.21e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-aminoethoxy(2R)-3-(dodecanoyloxy)-2-hydroxypropoxyphosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-OCT-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-OCT-12         0                                  
HETATM    1  N   UNK     0       3.191   8.002   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       4.524   7.232   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.858   8.002   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       7.192   7.232   0.000  0.00  0.00           O+0
HETATM    5  P   UNK     0       8.525   8.002   0.000  0.00  0.00           P+0
HETATM    6  O   UNK     0       9.295   6.668   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       7.755   9.336   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       9.859   8.772   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      11.193   8.002   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.526   8.772   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.860   8.002   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      15.194   8.772   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      16.527   8.002   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      16.527   6.462   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      17.861   8.772   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      19.195   8.002   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      20.528   8.772   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      21.862   8.002   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      23.196   8.772   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      24.529   8.002   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      25.863   8.772   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      27.197   8.002   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      28.531   8.772   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      29.864   8.002   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      31.198   8.772   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      12.526  10.312   0.000  0.00  0.00           O+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                                                            
CONECT    7    5                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   26                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   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                                                            
CONECT   26   10                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   50    0
END

Synonyms

Value	Source
Monolauroylphosphatidylethanolamine	MeSH
C12-LPE	MeSH
LysoLPE	MeSH
Lysolauroylphosphatidylethanolamine	MeSH
1-Dodecanoyl-sn-glycerophosphoethanolamine	MeSH

Molecular Formula

C₁₇H₃₆NO₇P

Average Mass

397.444

Monoisotopic Mass

397.222939023

IUPAC Name

(2-aminoethoxy)[(2R)-3-(dodecanoyloxy)-2-hydroxypropoxy]phosphinic acid

Traditional Name

2-aminoethoxy(2R)-3-(dodecanoyloxy)-2-hydroxypropoxyphosphinic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCC(=O)OC[C@@H](O)COP(O)(=O)OCCN

InChI Identifier

InChI=1S/C17H36NO7P/c1-2-3-4-5-6-7-8-9-10-11-17(20)23-14-16(19)15-25-26(21,22)24-13-12-18/h16,19H,2-15,18H2,1H3,(H,21,22)/t16-/m1/s1

InChI Key

IZDRGPDUDLWAGR-MRXNPFEDSA-N

Chemical Taxonomy

Functional Ontology

Physical Properties

Spectra

Biological Properties

Human Proteins and Enzymes

Human Pathways

Metabolic Reactions

Health Effects and Bioactivity

Microbial Sources

Exposure Sources

Host Biospecimen and Location

External Links

References

Showing metabocard for LysoPE(12:0/0:0) (MMDBc0060347)

MOL for #<Metabolite:0x00007fd5f9cdcba8>

3D MOL for #<Metabolite:0x00007fd5f9cdcba8>

3D SDF for #<Metabolite:0x00007fd5f9cdcba8>

3D-SDF for #<Metabolite:0x00007fd5f9cdcba8>

PDB for #<Metabolite:0x00007fd5f9cdcba8>

3D PDB for #<Metabolite:0x00007fd5f9cdcba8>

SMILES for #<Metabolite:0x00007fd5f9cdcba8>

INCHI for #<Metabolite:0x00007fd5f9cdcba8>

Structure for #<Metabolite:0x00007fd5f9cdcba8>

3D Structure for #<Metabolite:0x00007fd5f9cdcba8>