NP-MRD: Showing NP-Card for (2-{[(2r)-3-(hexadecyloxy)-2-hydroxypropyl phosphonato]oxy}ethyl)trimethylazanium (NP0209872)

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Record Information

Version

2.0

Created at

2022-09-05 07:27:38 UTC

Updated at

2022-09-05 07:27:38 UTC

NP-MRD ID

NP0209872

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2-{[(2r)-3-(hexadecyloxy)-2-hydroxypropyl phosphonato]oxy}ethyl)trimethylazanium

Description

Lysophosphatidylcholine O-16:0/0:0, Also known as GPC(O-16:0/0:0) Or 1-hexadecyl-sn-glycero-3-phosphocholine, belongs to the class of organic compounds known as monoalkylglycerophosphocholines. Monoalkylglycerophosphocholines are compounds containing glycerophosphocholine moiety attached to an fatty acyl chain through an ether bond. Thus, lysophosphatidylcholine O-16:0/0:0 Is considered to be a glycerophosphocholine lipid molecule. Lysophosphatidylcholine O-16:0/0:0 Is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1572001311617132D          

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M  CHG  2  25   1  28  -1
M  END

     RDKit          3D

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M  CHG  2  25  -1  29   1
M  END


  Mrv1572001311617132D          

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 10  9  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
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 20 18  1  0  0  0  0
 21 19  1  0  0  0  0
 24 22  1  0  0  0  0
 24 23  1  0  0  0  0
 25  2  1  0  0  0  0
 25  3  1  0  0  0  0
 25  4  1  0  0  0  0
 25 19  1  0  0  0  0
 24 26  1  6  0  0  0
 29 20  1  0  0  0  0
 29 22  1  0  0  0  0
 30 21  1  0  0  0  0
 31 23  1  0  0  0  0
 32 27  2  0  0  0  0
 32 28  1  0  0  0  0
 32 30  1  0  0  0  0
 32 31  1  0  0  0  0
 24 33  1  6  0  0  0
M  CHG  2  25   1  28  -1
M  END
> <DATABASE_ID>
NP0209872

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@](O)(COCCCCCCCCCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C24H52NO6P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-20-29-22-24(26)23-31-32(27,28)30-21-19-25(2,3)4/h24,26H,5-23H2,1-4H3/t24-/m1/s1

> <INCHI_KEY>
VLBPIWYTPAXCFJ-XMMPIXPASA-N

> <FORMULA>
C24H52NO6P

> <MOLECULAR_WEIGHT>
481.655

> <EXACT_MASS>
481.353225396

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
58.97175562800394

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{[(2R)-3-(hexadecyloxy)-2-hydroxypropyl phosphonato]oxy}ethyl)trimethylazanium

> <ALOGPS_LOGP>
2.36

> <JCHEM_LOGP>
1.5735380728615884

> <ALOGPS_LOGS>
-6.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.680359309358309

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8553441415966123

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3931778346128443

> <JCHEM_POLAR_SURFACE_AREA>
88.05000000000001

> <JCHEM_REFRACTIVITY>
142.5191

> <JCHEM_ROTATABLE_BOND_COUNT>
24

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.55e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-{[(2R)-3-(hexadecyloxy)-2-hydroxypropyl phosphonato]oxy}ethyl)trimethylazanium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 31-JAN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-JAN-16         0                                  
HETATM    1  C   UNK     0     -17.338   0.282   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.338   0.282   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.774  -1.822   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.234   0.845   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -16.004  -0.488   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -14.670   0.282   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -13.337  -0.488   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -12.003   0.282   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -10.669  -0.488   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -9.336   0.282   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.002  -0.488   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.668   0.282   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.335  -0.488   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001   0.282   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667  -0.488   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334   0.282   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000  -0.488   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334   0.282   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.670  -1.258   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  -0.488   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.337  -0.488   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335  -0.488   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.002  -0.488   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668   0.282   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0      16.004  -0.488   0.000  0.00  0.00           N+1
HETATM   26  O   UNK     0       6.668   1.822   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       9.899  -1.822   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      11.439   0.845   0.000  0.00  0.00           O-1
HETATM   29  O   UNK     0       4.001   0.282   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      12.003  -1.258   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       9.336   0.282   0.000  0.00  0.00           O+0
HETATM   32  P   UNK     0      10.669  -0.488   0.000  0.00  0.00           P+0
HETATM   33  H   UNK     0       6.668  -1.258   0.000  0.00  0.00           H+0
CONECT    1    5                                                            
CONECT    2   25                                                            
CONECT    3   25                                                            
CONECT    4   25                                                            
CONECT    5    1    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   20                                                       
CONECT   19   21   25                                                       
CONECT   20   18   29                                                       
CONECT   21   19   30                                                       
CONECT   22   24   29                                                       
CONECT   23   24   31                                                       
CONECT   24   22   23   26   33                                             
CONECT   25    2    3    4   19                                             
CONECT   26   24                                                            
CONECT   27   32                                                            
CONECT   28   32                                                            
CONECT   29   20   22                                                       
CONECT   30   21   32                                                       
CONECT   31   23   32                                                       
CONECT   32   27   28   30   31                                             
CONECT   33   24                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   64    0
END

View in JSmol

Synonyms

Value	Source
1-Hexadecyl-sn-glycero-3-phosphocholine	ChEBI
1-O-Hexadecyl-2-lyso-sn-glycero-3-phosphocholine	ChEBI
1-O-Hexadecyl-sn-glycero-3-phosphatidylcholine	ChEBI
1-O-Hexadecyl-sn-glycero-3-phosphocholine	ChEBI
1-O-Hexadecyl-sn-glyceryl-3-phosphorylcholine	ChEBI
1-Palmityl-GPC	ChEBI
GPC(O-16:0/0:0)	ChEBI
LPC O-16:0/0:0	ChEBI
Lysophosphatidylcholine(O-16:0/0:0)	ChEBI
PC O-16:0/0:0	ChEBI
PC(O-16:0/0:0)	ChEBI
1-O-Hexadecyl-2-lyso-glycero-3-phosphorylcholine	MeSH
lyso-GEPC	MeSH

Chemical Formula

C₂₄H₅₂NO₆P

Average Mass

481.6550 Da

Monoisotopic Mass

481.35323 Da

IUPAC Name

(2-{[(2R)-3-(hexadecyloxy)-2-hydroxypropyl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-3-(hexadecyloxy)-2-hydroxypropyl phosphonato]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

[H][C@@](O)(COCCCCCCCCCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C

InChI Identifier

InChI=1S/C24H52NO6P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-20-29-22-24(26)23-31-32(27,28)30-21-19-25(2,3)4/h24,26H,5-23H2,1-4H3/t24-/m1/s1

InChI Key

VLBPIWYTPAXCFJ-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, 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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monoalkylglycerophosphocholines. Monoalkylglycerophosphocholines are compounds containing glycerophosphocholine moiety attached to an fatty acyl chain through an ether bond.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphocholines

Direct Parent

Monoalkylglycerophosphocholines

Alternative Parents

Substituents

Monoalkylglycerophosphocholine
Phosphocholine
Glycerol ether
Dialkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Quaternary ammonium salt
Tetraalkylammonium salt
Secondary alcohol
Ether
Dialkyl ether
Hydrocarbon derivative
Alcohol
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Amine
Organic salt
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

lysophosphatidylcholine O-16:0 (CHEBI:64496 )
Monoalkylglycerophosphocholines (LMGP01060010 )

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	2.36	ALOGPS
logP	1.57	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	88.05 Å²	ChemAxon
Rotatable Bond Count	24	ChemAxon
Refractivity	142.52 m³·mol⁻¹	ChemAxon
Polarizability	58.97 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

162126

PDB ID

Not Available

ChEBI ID

64496

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2-{[(2r)-3-(hexadecyloxy)-2-hydroxypropyl phosphonato]oxy}ethyl)trimethylazanium (NP0209872)

MOL for NP0209872 ((2-{[(2r)-3-(hexadecyloxy)-2-hydroxypropyl phosphonato]oxy}ethyl)trimethylazanium)

3D MOL for NP0209872 ((2-{[(2r)-3-(hexadecyloxy)-2-hydroxypropyl phosphonato]oxy}ethyl)trimethylazanium)

3D SDF for NP0209872 ((2-{[(2r)-3-(hexadecyloxy)-2-hydroxypropyl phosphonato]oxy}ethyl)trimethylazanium)

3D-SDF for NP0209872 ((2-{[(2r)-3-(hexadecyloxy)-2-hydroxypropyl phosphonato]oxy}ethyl)trimethylazanium)

PDB for NP0209872 ((2-{[(2r)-3-(hexadecyloxy)-2-hydroxypropyl phosphonato]oxy}ethyl)trimethylazanium)

3D PDB for NP0209872 ((2-{[(2r)-3-(hexadecyloxy)-2-hydroxypropyl phosphonato]oxy}ethyl)trimethylazanium)

SMILES for NP0209872 ((2-{[(2r)-3-(hexadecyloxy)-2-hydroxypropyl phosphonato]oxy}ethyl)trimethylazanium)

INCHI for NP0209872 ((2-{[(2r)-3-(hexadecyloxy)-2-hydroxypropyl phosphonato]oxy}ethyl)trimethylazanium)

Structure for NP0209872 ((2-{[(2r)-3-(hexadecyloxy)-2-hydroxypropyl phosphonato]oxy}ethyl)trimethylazanium)

3D Structure for NP0209872 ((2-{[(2r)-3-(hexadecyloxy)-2-hydroxypropyl phosphonato]oxy}ethyl)trimethylazanium)