NP-MRD: Showing NP-Card for 2-aminoethoxy((2r)-2-hydroxy-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propoxy)phosphinic acid (NP0171906)

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Record Information

Version

2.0

Created at

2022-09-03 08:37:01 UTC

Updated at

2022-09-03 08:37:01 UTC

NP-MRD ID

NP0171906

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-aminoethoxy((2r)-2-hydroxy-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propoxy)phosphinic acid

Description

LysoPE(18:2(9Z,12Z)/0:0), Also known as PE(18:2(9Z,12Z)/0:0) Or lyso-pe(18:2N6/0:0), 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. Thus, lysope(18:2(9Z,12Z)/0:0) Is considered to be a glycerophosphoethanolamine lipid molecule. 2-aminoethoxy((2r)-2-hydroxy-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propoxy)phosphinic acid is found in Trypanosoma brucei. 2-aminoethoxy((2r)-2-hydroxy-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propoxy)phosphinic acid was first documented in 2012 (PMID: 22502909). LysoPE(18:2(9Z,12Z)/0:0) Is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241201422D          

 33 32  0  0  1  0            999 V2000
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   22.4134  -17.8677    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   21.7381  -17.4780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7637  -17.8677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0630  -17.8677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8864  -18.6474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   15.3467  -17.8678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  5 32  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv0541 02241201422D          

 33 32  0  0  1  0            999 V2000
   23.0884  -17.4780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4134  -17.8677    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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 28 27  1  0  0  0  0
 29 28  1  0  0  0  0
 30 29  1  0  0  0  0
 31 30  1  0  0  0  0
 32 31  1  0  0  0  0
 33 32  2  0  0  0  0
  5 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0171906

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@](O)(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)COP(O)(=O)OCCN

> <INCHI_IDENTIFIER>
InChI=1S/C23H44NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-23(26)29-20-22(25)21-31-32(27,28)30-19-18-24/h6-7,9-10,22,25H,2-5,8,11-21,24H2,1H3,(H,27,28)/b7-6-,10-9-/t22-/m1/s1

> <INCHI_KEY>
DBHKHNGBVGWQJE-USWSLJGRSA-N

> <FORMULA>
C23H44NO7P

> <MOLECULAR_WEIGHT>
477.5717

> <EXACT_MASS>
477.285539279

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
53.22949314948558

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-aminoethoxy)[(2R)-2-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphinic acid

> <ALOGPS_LOGP>
4.66

> <JCHEM_LOGP>
3.695155443142332

> <ALOGPS_LOGS>
-5.30

> <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>
128.8477

> <JCHEM_ROTATABLE_BOND_COUNT>
23

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.37e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-aminoethoxy(2R)-2-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]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      43.098 -32.626   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      41.838 -33.353   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      40.578 -32.626   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      44.359 -33.353   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      39.318 -33.353   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      40.855 -34.808   0.000  0.00  0.00           O+0
HETATM    7  P   UNK     0      45.619 -32.626   0.000  0.00  0.00           P+0
HETATM    8  O   UNK     0      44.891 -31.365   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      46.347 -33.886   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      46.879 -31.898   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      48.140 -32.626   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      49.400 -31.898   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      50.660 -32.626   0.000  0.00  0.00           N+0
HETATM   14  H   UNK     0      42.935 -34.864   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0      15.309 -33.353   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.643 -32.583   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.977 -33.353   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      19.311 -32.583   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      20.644 -33.353   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      21.978 -32.583   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      23.312 -32.583   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      24.646 -33.353   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      25.980 -32.583   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      27.313 -32.583   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      28.647 -33.353   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      29.981 -32.583   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      31.315 -33.353   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      32.649 -32.583   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      33.982 -33.353   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      35.316 -32.583   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      36.650 -33.353   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      37.984 -32.583   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      37.984 -31.043   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   32                                                       
CONECT    6    2                                                            
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    5                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   64    0
END

View in JSmol

Synonyms

Value	Source
(9Z,12Z-Octadecadienoyl)-lysophosphatidylethanolamine	ChEBI
1-(9Z,12Z-Octadecadienoyl)-glycero-3-phosphoethanolamine	ChEBI
1-Linoleoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine	ChEBI
Lyso-pe(18:2n6/0:0)	ChEBI
LysoPE(18:2W6/0:0)	ChEBI
PE(18:2(9Z,12Z)/0:0)	ChEBI
LPE(18:2)	HMDB
LPE(18:2/0:0)	HMDB
Lyso-pe(18:2)	HMDB
Lysophosphatidylethanolamine(18:2/0:0)	HMDB
Lysophosphatidylethanolamine(18:2)	HMDB
Lyso-pe(18:2/0:0)	HMDB
LysoPE(18:2)	HMDB
1-(9Z,12Z-Octadecadienoyl)-2-hydroxy-sn-glycero-3-phosphoethanolamine	HMDB
LysoPE(18:2/0:0)	HMDB
LPE(18:2n6/0:0)	HMDB
LPE(18:2W6/0:0)	HMDB
Lyso-pe(18:2W6/0:0)	HMDB
LysoPE(18:2n6/0:0)	HMDB
Lysophosphatidylethanolamine(18:2n6/0:0)	HMDB
Lysophosphatidylethanolamine(18:2W6/0:0)	HMDB
1-Linoleoyl-gpe	HMDB
1-Linoleoyl-lysophosphatidylethanolamine	HMDB
1-Linoleoyl-sn-glycero-3-phosphoethanolamine	HMDB
GPE(18:2(9Z,12Z))	HMDB
GPE(18:2(9Z,12Z)/0:0)	HMDB
GPE(18:2)	HMDB
GPE(18:2n6)	HMDB
GPE(18:2n6/0:0)	HMDB
GPE(18:2W6)	HMDB
GPE(18:2W6/0:0)	HMDB
LPE(18:2(9Z,12Z))	HMDB
LPE(18:2(9Z,12Z)/0:0)	HMDB
LPE(18:2n6)	HMDB
LPE(18:2W6)	HMDB
LysoPE(18:2(9Z,12Z))	HMDB
LysoPE(18:2n6)	HMDB
LysoPE(18:2W6)	HMDB
Lysophosphatidylethanolamine(18:2(9Z,12Z))	HMDB
Lysophosphatidylethanolamine(18:2(9Z,12Z)/0:0)	HMDB
Lysophosphatidylethanolamine(18:2n6)	HMDB
Lysophosphatidylethanolamine(18:2W6)	HMDB
LysoPE(18:2(9Z,12Z)/0:0)	Lipid Annotator, ChEBI

Chemical Formula

C₂₃H₄₄NO₇P

Average Mass

477.5717 Da

Monoisotopic Mass

477.28554 Da

IUPAC Name

(2-aminoethoxy)[(2R)-2-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphinic acid

Traditional Name

2-aminoethoxy(2R)-2-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxyphosphinic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](O)(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)COP(O)(=O)OCCN

InChI Identifier

InChI=1S/C23H44NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-23(26)29-20-22(25)21-31-32(27,28)30-19-18-24/h6-7,9-10,22,25H,2-5,8,11-21,24H2,1H3,(H,27,28)/b7-6-,10-9-/t22-/m1/s1

InChI Key

DBHKHNGBVGWQJE-USWSLJGRSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Trypanosoma brucei	LOTUS Database	35616633

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

1-acyl-sn-glycero-3-phosphoethanolamine (CHEBI:83058 )
Monoacylglycerophosphoethanolamines (LMGP02050011 )

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	4.66	ALOGPS
logP	3.7	ChemAxon
logS	-5.3	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	23	ChemAxon
Refractivity	128.85 m³·mol⁻¹	ChemAxon
Polarizability	53.23 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0011507

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB028223

KNApSAcK ID

Not Available

Chemspider ID

24769385

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

52925130

PDB ID

Not Available

ChEBI ID

83058

Good Scents ID

Not Available

References

General References

Zhang J, Yan L, Tian M, Huang Q, Peng S, Dong S, Shen H: The metabonomics of combined dietary exposure to phthalates and polychlorinated biphenyls in mice. J Pharm Biomed Anal. 2012 Jul;66:287-97. doi: 10.1016/j.jpba.2012.03.045. Epub 2012 Apr 3. [PubMed:22502909 ]
LOTUS database [Link]

Showing NP-Card for 2-aminoethoxy((2r)-2-hydroxy-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propoxy)phosphinic acid (NP0171906)

MOL for NP0171906 (2-aminoethoxy((2r)-2-hydroxy-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propoxy)phosphinic acid)

3D MOL for NP0171906 (2-aminoethoxy((2r)-2-hydroxy-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propoxy)phosphinic acid)

3D SDF for NP0171906 (2-aminoethoxy((2r)-2-hydroxy-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propoxy)phosphinic acid)

3D-SDF for NP0171906 (2-aminoethoxy((2r)-2-hydroxy-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propoxy)phosphinic acid)

PDB for NP0171906 (2-aminoethoxy((2r)-2-hydroxy-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propoxy)phosphinic acid)

3D PDB for NP0171906 (2-aminoethoxy((2r)-2-hydroxy-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propoxy)phosphinic acid)

SMILES for NP0171906 (2-aminoethoxy((2r)-2-hydroxy-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propoxy)phosphinic acid)

INCHI for NP0171906 (2-aminoethoxy((2r)-2-hydroxy-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propoxy)phosphinic acid)

Structure for NP0171906 (2-aminoethoxy((2r)-2-hydroxy-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propoxy)phosphinic acid)

3D Structure for NP0171906 (2-aminoethoxy((2r)-2-hydroxy-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propoxy)phosphinic acid)