NP-MRD: Showing NP-Card for LysoPE(0:0/20:0) (NP0091404)

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Record Information

Version

2.0

Created at

2022-05-11 18:37:47 UTC

Updated at

2022-05-11 18:37:47 UTC

NP-MRD ID

NP0091404

Secondary Accession Numbers

None

Natural Product Identification

Common Name

LysoPE(0:0/20:0)

Description

LysoPE(0:0/20:0), Also known as lyso-pe(20:0) Or lpe(0:0/20:0), Belongs to the class of organic compounds known as 2-acyl-sn-glycero-3-phosphoethanolamines. These are glycerophoethanolamines in which the glycerol is esterified with a fatty acid at O-2 position, and linked at position 3 to a phosphoethanolamine. Thus, lysope(0:0/20:0) Is considered to be a glycerophosphoethanolamine lipid molecule. LysoPE(0:0/20:0) Is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241201412D          

 35 34  0  0  1  0            999 V2000
   24.8350   -8.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1599   -8.4083    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   25.5101   -8.4083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8096   -8.4083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6331   -9.1879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.1852   -8.0186    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   25.7954   -7.3434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   12.2014   -9.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 34  6  1  0  0  0  0
 34 35  2  0  0  0  0
M  END

     RDKit          3D

 86 85  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv0541 02241201412D          

 35 34  0  0  1  0            999 V2000
   24.8350   -8.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   20.7752   -9.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4896   -9.6004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2041   -9.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9186   -9.6004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9186  -10.4254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  3  1  0  0  0  0
  2  6  1  6  0  0  0
  7  4  1  0  0  0  0
  8  7  2  0  0  0  0
  9  7  1  0  0  0  0
 10  7  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
  2 14  1  1  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
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  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
 33 34  1  0  0  0  0
 34  6  1  0  0  0  0
 34 35  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0091404

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C25H52NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-25(28)33-24(22-27)23-32-34(29,30)31-21-20-26/h24,27H,2-23,26H2,1H3,(H,29,30)/t24-/m1/s1

> <INCHI_KEY>
QEQAJJJSRGAOOG-XMMPIXPASA-N

> <FORMULA>
C25H52NO7P

> <MOLECULAR_WEIGHT>
509.6566

> <EXACT_MASS>
509.348139535

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
60.79816676334074

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-aminoethoxy)[(2R)-3-hydroxy-2-(icosanoyloxy)propoxy]phosphinic acid

> <ALOGPS_LOGP>
5.43

> <JCHEM_LOGP>
5.308136115327011

> <ALOGPS_LOGS>
-5.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.579269652388977

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8688048676175866

> <JCHEM_PKA_STRONGEST_BASIC>
9.999917895738319

> <JCHEM_POLAR_SURFACE_AREA>
128.31

> <JCHEM_REFRACTIVITY>
135.81650000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
27

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.93e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-aminoethoxy(2R)-3-hydroxy-2-(icosanoyloxy)propoxyphosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      46.359 -14.968   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      45.098 -15.695   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      43.838 -14.968   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      47.619 -15.695   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      42.578 -15.695   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      44.115 -17.151   0.000  0.00  0.00           O+0
HETATM    7  P   UNK     0      48.879 -14.968   0.000  0.00  0.00           P+0
HETATM    8  O   UNK     0      48.151 -13.708   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      49.607 -16.228   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      50.139 -14.240   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      51.399 -14.968   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      52.660 -14.240   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      53.920 -14.968   0.000  0.00  0.00           N+0
HETATM   14  H   UNK     0      46.196 -17.206   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0      17.441 -17.151   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      18.775 -17.921   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      20.109 -17.151   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      21.442 -17.921   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      22.776 -17.151   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      24.110 -17.921   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      25.443 -17.151   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      26.777 -17.921   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      28.111 -17.151   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      29.444 -17.921   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      30.778 -17.151   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      32.112 -17.921   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      33.445 -17.151   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      34.779 -17.921   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      36.113 -17.151   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      37.447 -17.921   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      38.780 -17.151   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      40.114 -17.921   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      41.448 -17.151   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      42.781 -17.921   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      42.781 -19.461   0.000  0.00  0.00           O+0
CONECT    1    2    4                                                       
CONECT    2    1    3    6   14                                             
CONECT    3    2    5                                                       
CONECT    4    1    7                                                       
CONECT    5    3                                                            
CONECT    6    2   34                                                       
CONECT    7    4    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14    2                                                            
CONECT   15   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   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   34                                                       
CONECT   34   33    6   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   68    0
END

View in JSmol

Synonyms

Value	Source
(2-Aminoethoxy)[(2R)-3-hydroxy-2-(icosanoyloxy)propoxy]phosphinic acid	ChEBI
1-Hydroxy-2-arachidonyl-sn-glycero-3-phosphoethanolamine	ChEBI
2-Arachidoyl-sn-glycero-3-phosphoethanolamine	ChEBI
2-Eicosanoyl-sn-glycero-3-phosphoethanolamine	ChEBI
Eicosanoyl-lysophosphatidylethanolamine	ChEBI
LPE(0:0/20:0)	ChEBI
LPE(20:0)	ChEBI
Lyso-pe(0:0/20:0)	ChEBI
Lyso-pe(20:0)	ChEBI
LysoPE(20:0)	ChEBI
Lysophosphatidylethanolamine(0:0/20:0)	ChEBI
Lysophosphatidylethanolamine(20:0)	ChEBI
(2-Aminoethoxy)[(2R)-3-hydroxy-2-(icosanoyloxy)propoxy]phosphinate	Generator
1-Hydroxy-2-eicosanoyl-sn-glycero-3-phosphoethanolamine	HMDB
2-Arachidoylglycerophosphoethanolamine	HMDB
2-Eicosanoylglycerophosphoethanolamine	HMDB
LysoPE(0:0/20:0)	Lipid Annotator

Chemical Formula

C₂₅H₅₂NO₇P

Average Mass

509.6566 Da

Monoisotopic Mass

509.34814 Da

IUPAC Name

(2-aminoethoxy)[(2R)-3-hydroxy-2-(icosanoyloxy)propoxy]phosphinic acid

Traditional Name

2-aminoethoxy(2R)-3-hydroxy-2-(icosanoyloxy)propoxyphosphinic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C25H52NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-25(28)33-24(22-27)23-32-34(29,30)31-21-20-26/h24,27H,2-23,26H2,1H3,(H,29,30)/t24-/m1/s1

InChI Key

QEQAJJJSRGAOOG-XMMPIXPASA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-acyl-sn-glycero-3-phosphoethanolamines. These are glycerophoethanolamines in which the glycerol is esterified with a fatty acid at O-2 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

2-acyl-sn-glycero-3-phosphoethanolamines

Alternative Parents

Substituents

2-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
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Alcohol
Primary aliphatic amine
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Amine
Primary amine
Primary alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	5.43	ALOGPS
logP	5.31	ChemAxon
logS	-5.7	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	27	ChemAxon
Refractivity	135.82 m³·mol⁻¹	ChemAxon
Polarizability	60.8 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

External Links

HMDB ID

HMDB0011481

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB028197

KNApSAcK ID

Not Available

Chemspider ID

24769362

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53480930

PDB ID

Not Available

ChEBI ID

131691

Good Scents ID

Not Available

References

General References

Showing NP-Card for LysoPE(0:0/20:0) (NP0091404)

MOL for NP0091404 (LysoPE(0:0/20:0))

3D MOL for NP0091404 (LysoPE(0:0/20:0))

3D SDF for NP0091404 (LysoPE(0:0/20:0))

3D-SDF for NP0091404 (LysoPE(0:0/20:0))

PDB for NP0091404 (LysoPE(0:0/20:0))

3D PDB for NP0091404 (LysoPE(0:0/20:0))

SMILES for NP0091404 (LysoPE(0:0/20:0))

INCHI for NP0091404 (LysoPE(0:0/20:0))

Structure for NP0091404 (LysoPE(0:0/20:0))

3D Structure for NP0091404 (LysoPE(0:0/20:0))