MiMeDB: Showing metabocard for LysoPE(10:0/0:0) (MMDBc0047849)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 15:45:51 UTC

Update Date

2022-09-01 02:00:00 UTC

Metabolite ID

MMDBc0047849

Metabolite Identification

Common Name

LysoPE(10:0/0:0)

Description

LysoPE(10:0/0:0) is a lysophosphatidylethanolamine or a lysophospholipid. The term 'lysophospholipid' (LPL) refers to any phospholipid that is missing one of its two O-acyl chains. Thus, LPLs have a free alcohol in either the sn-1 or sn-2 position. The prefix 'lyso-' comes from the fact that lysophospholipids were originally found to be hemolytic however it is now used to refer generally to phospholipids missing an acyl chain. LPLs are usually the result of phospholipase A-type enzymatic activity on regular phospholipids such as phosphatidylcholine or phosphatidic acid, although they can also be generated by the acylation of glycerophospholipids or the phosphorylation of monoacylglycerols. 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. They are also approved for indoor use to preserve stored crops and commercial cut flowers. As a breakdown product of phosphatidylethanolamine (PE), LPE is present in cells of all organisms.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 10181208532D          

 24 23  0  0  1  0            999 V2000
    0.4717    3.5724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1862    3.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9007    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6151    3.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3296    3.5724    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.7421    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9171    4.2868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0441    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7586    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4730    3.9849    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1875    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9020    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6164    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6164    2.7474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3309    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0454    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7599    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4743    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1888    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9033    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6177    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3322    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0467    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4730    4.8099    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
 10 24  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0047849

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H32NO7P/c1-2-3-4-5-6-7-8-9-15(18)21-12-14(17)13-23-24(19,20)22-11-10-16/h14,17H,2-13,16H2,1H3,(H,19,20)/t14-/m1/s1

> <INCHI_KEY>
GHDPWZXAKQIRIU-CQSZACIVSA-N

> <FORMULA>
C15H32NO7P

> <MOLECULAR_WEIGHT>
369.3908

> <EXACT_MASS>
369.191638895

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
39.108742196312676

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.11

> <JCHEM_LOGP>
0.8624494364756649

> <ALOGPS_LOGS>
-2.69

> <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>
89.8065

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.50e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-aminoethoxy(2R)-3-(decanoyloxy)-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       0.881   6.668   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       2.214   5.898   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.548   6.668   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.882   5.898   0.000  0.00  0.00           O+0
HETATM    5  P   UNK     0       6.215   6.668   0.000  0.00  0.00           P+0
HETATM    6  O   UNK     0       6.985   5.335   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       5.445   8.002   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       7.549   7.438   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.883   6.668   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.216   7.438   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.550   6.668   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.884   7.438   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      14.217   6.668   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      14.217   5.128   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      15.551   7.438   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.885   6.668   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      18.218   7.438   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      19.552   6.668   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      20.886   7.438   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      22.219   6.668   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      23.553   7.438   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      24.887   6.668   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      26.221   7.438   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.216   8.978   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   24                                                  
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                                                            
CONECT   24   10                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

Synonyms

Not Available

Molecular Formula

C₁₅H₃₂NO₇P

Average Mass

369.3908

Monoisotopic Mass

369.191638895

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H32NO7P/c1-2-3-4-5-6-7-8-9-15(18)21-12-14(17)13-23-24(19,20)22-11-10-16/h14,17H,2-13,16H2,1H3,(H,19,20)/t14-/m1/s1

InChI Key

GHDPWZXAKQIRIU-CQSZACIVSA-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
Phosphoethanolamine
Fatty acid ester
Dialkyl phosphate
Organic phosphoric acid derivative
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Amino acid or derivatives
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organonitrogen compound
Hydrocarbon derivative
Alcohol
Primary aliphatic amine
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Amine
Organooxygen compound
Primary amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.75 g/L	ALOGPS
logP	1.11	ALOGPS
logP	0.86	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	1.87	ChemAxon
pKa (Strongest Basic)	10	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	128.31 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	89.81 m³·mol⁻¹	ChemAxon
Polarizability	39.11 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6x-2900000000-02f731832783a09735fd	2016-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9312000000-aafec9465f9cf05f567b	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9310000000-e576b0283d7039f94f83	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9200000000-f482648d7de995ed9247	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0g4i-1904000000-a8441533f7ee0e8f6355	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00fr-3900000000-39965d549a2a1b7ec4c4	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9300000000-4d4e4c135267df00499d	2016-09-14	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

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0038335	PE(10:0/10:0)	Capric acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0038336	PE(10:0/12:0)	Dodecanoic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0038337	PE(10:0/14:0)	LysoPE(10:0/0:0)	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0038338	PE(10:0/15:0)	LysoPE(10:0/0:0)	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0038339	PE(10:0/16:0)	LysoPE(10:0/0:0)	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0038340	PE(10:0/16:1(9Z))	(9Z)-hexadecenoic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0038341	PE(10:0/17:0cycw7c)	8‐(2‐Hexylcyclopropyl)octanoic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0038342	PE(10:0/18:0)	LysoPE(10:0/0:0)	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0038343	PE(10:0/18:1(11Z))	11Z-Octadecenoic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0038344	PE(10:0/19:1(12Z))	12Z-Nonadecenoic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0038345	PE(10:0/19:0cycw8c)	10‐(2‐Hexylcyclopropyl)decanoic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0038396	PE(10:0/10:0(3-OH))	(R)-3-Hydroxydecanoic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0038397	PE(10:0/12:0(3-OH))	3-Hydroxydodecanoic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0038398	PE(10:0/14:0(3-OH))	(R)-3-Hydroxy-tetradecanoic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0038399	PE(10:0/19:iso)	17-Methylstearate	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0038503	PE(10:0/18:1(9Z))	(9Z)-octadecenoic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0038510	PE(10:0/19:1(9Z))	9Z-Nonadecenoic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0038557	PE(10:0/14:1(9Z))	LysoPE(10:0/0:0)	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0038558	PE(10:0/14:1(11Z))	(11Z)-Tetradecenoic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0038564	PE(10:0/20:1(13Z))	13-Eicosenoic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0038565	PE(10:0/20:1(11Z))	11Z-Eicosenoic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0038566	PE(10:0/15:1(9Z))	(9Z)-pentadec-9-enoic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0038567	PE(10:0/15:1(11Z))	(11Z)-Pentadecenoic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0038568	PE(10:0/16:1(11Z))	11-hexadecenoic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0038609	PE(10:0/22:1(9Z))	9Z-Docosenoic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0038610	PE(10:0/22:1(11Z))	Cetoleic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0038619	PE(10:0/23:1(9Z))	9Z-Tricosenoic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0038620	PE(10:0/23:1(11Z))	11Z-Tricosenoic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0038630	PE(10:0/24:1(9Z))	9Z-Tetracosenoic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0038631	PE(10:0/24:1(11Z))	11Z-Tetracosenoic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0038643	PE(10:0/25:1(9Z))	9Z-Pentacosenoic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0038644	PE(10:0/25:1(11Z))	11Z-Pentacosenoic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0038645	PE(10:0/20:0)	Arachidic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0038663	PE(10:0/26:1(9Z))	9Z-Hexacosenoic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0038664	PE(10:0/26:1(11Z))	11Z-Hexacosenoic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880

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

134732381

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Ramirez-Gaona M, Marcu A, Pon A, Guo AC, Sajed T, Wishart NA, Karu N, Djoumbou Feunang Y, Arndt D, Wishart DS: YMDB 2.0: a significantly expanded version of the yeast metabolome database. Nucleic Acids Res. 2017 Jan 4;45(D1):D440-D445. doi: 10.1093/nar/gkw1058. Epub 2016 Nov 28. [PubMed:27899612 ]

Showing metabocard for LysoPE(10:0/0:0) (MMDBc0047849)

MOL for #<Metabolite:0x00007fa5000a0440>

3D MOL for #<Metabolite:0x00007fa5000a0440>

3D SDF for #<Metabolite:0x00007fa5000a0440>

3D-SDF for #<Metabolite:0x00007fa5000a0440>

PDB for #<Metabolite:0x00007fa5000a0440>

3D PDB for #<Metabolite:0x00007fa5000a0440>

SMILES for #<Metabolite:0x00007fa5000a0440>

INCHI for #<Metabolite:0x00007fa5000a0440>

Structure for #<Metabolite:0x00007fa5000a0440>

3D Structure for #<Metabolite:0x00007fa5000a0440>