NP-MRD: Showing NP-Card for (2r)-3-(hexadecanoyloxy)-2-hydroxypropoxy(2-(trimethylammonio)ethoxy)phosphinic acid (NP0262685)

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Record Information

Version

2.0

Created at

2022-09-08 05:36:28 UTC

Updated at

2022-09-08 05:36:28 UTC

NP-MRD ID

NP0262685

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r)-3-(hexadecanoyloxy)-2-hydroxypropoxy(2-(trimethylammonio)ethoxy)phosphinic acid

Description

1-O-palmitoyl-sn-glycero-3-phosphocholine, also known as 1-palmitoyl-2-lyso-sn-glycero-3-PC or gpcho 16:0/0:0, Belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphocholine. (2r)-3-(hexadecanoyloxy)-2-hydroxypropoxy(2-(trimethylammonio)ethoxy)phosphinic acid is found in Populus tremula. (2r)-3-(hexadecanoyloxy)-2-hydroxypropoxy(2-(trimethylammonio)ethoxy)phosphinic acid was first documented in 1987 (PMID: 3444370). Based on a literature review a small amount of articles have been published on 1-O-palmitoyl-sn-glycero-3-phosphocholine (PMID: 11777459).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082207362D          

 33 32  0  0  1  0            999 V2000
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 30 31  1  0  0  0  0
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 30 33  1  0  0  0  0
M  CHG  1  30   1
M  END

     RDKit          3D

 84 83  0  0  0  0  0  0  0  0999 V2000
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 33 83  1  0
 33 84  1  0
M  CHG  1  30   1
M  END


  Mrv1652309082207362D          

 33 32  0  0  1  0            999 V2000
    8.4711   -5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  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
  6  7  1  0  0  0  0
  7  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  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 24 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
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
M  CHG  1  30   1
M  END
> <DATABASE_ID>
NP0262685

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C24H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-24(27)30-21-23(26)22-32-33(28,29)31-20-19-25(2,3)4/h23,26H,5-22H2,1-4H3/p+1/t23-/m1/s1

> <INCHI_KEY>
ASWBNKHCZGQVJV-HSZRJFAPSA-O

> <FORMULA>
C24H51NO7P

> <MOLECULAR_WEIGHT>
496.645

> <EXACT_MASS>
496.339766404

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
58.62787468598916

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R)-3-(hexadecanoyloxy)-2-hydroxypropoxy][2-(trimethylazaniumyl)ethoxy]phosphinic acid

> <JCHEM_LOGP>
1.1927424768615884

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.655609236411614

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8553406136270887

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4040033707844772

> <JCHEM_POLAR_SURFACE_AREA>
102.29000000000002

> <JCHEM_REFRACTIVITY>
143.39539999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
24

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-3-(hexadecanoyloxy)-2-hydroxypropoxy(2-(trimethylammonio)ethoxy)phosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      15.813 -10.669   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.146 -11.439   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.480 -10.669   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.814 -11.439   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.147 -10.669   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      22.481 -11.439   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      23.815 -10.669   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      25.148 -11.439   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      26.482 -10.669   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      27.816 -11.439   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      29.149 -10.669   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      30.483 -11.439   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      31.817 -10.669   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      33.150 -11.439   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      34.484 -10.669   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      35.818 -11.439   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      35.818 -12.979   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      37.152 -10.669   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      38.485 -11.439   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      39.819 -10.669   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      39.819  -9.129   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      41.153 -11.439   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      42.486 -10.669   0.000  0.00  0.00           O+0
HETATM   24  P   UNK     0      43.820 -11.439   0.000  0.00  0.00           P+0
HETATM   25  O   UNK     0      43.050 -12.773   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      44.590 -10.106   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      45.154 -12.209   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      46.487 -11.439   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      47.821 -12.209   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0      49.155 -11.439   0.000  0.00  0.00           N+1
HETATM   31  C   UNK     0      50.488 -10.669   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      49.925 -12.773   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      48.385 -10.106   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    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   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   30                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   64    0
END

View in JSmol

Synonyms

Value	Source
1-Palmitoyl-2-lyso-sn-glycero-3-PC	ChEBI
1-Palmitoyl-sn-glycero-3-phosphocholine	ChEBI
1-Palmitoylglycerophosphocholine	ChEBI
GPCho 16:0/0:0	ChEBI
GPCho(16:0/0:0)	ChEBI

Chemical Formula

C₂₄H₅₁NO₇P

Average Mass

496.6450 Da

Monoisotopic Mass

496.33977 Da

IUPAC Name

[(2R)-3-(hexadecanoyloxy)-2-hydroxypropoxy][2-(trimethylazaniumyl)ethoxy]phosphinic acid

Traditional Name

(2R)-3-(hexadecanoyloxy)-2-hydroxypropoxy(2-(trimethylammonio)ethoxy)phosphinic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(O)(=O)OCC[N+](C)(C)C

InChI Identifier

InChI=1S/C24H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-24(27)30-21-23(26)22-32-33(28,29)31-20-19-25(2,3)4/h23,26H,5-22H2,1-4H3/p+1/t23-/m1/s1

InChI Key

ASWBNKHCZGQVJV-HSZRJFAPSA-O

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
Populus tremula	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphocholine.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphocholines

Direct Parent

1-acyl-sn-glycero-3-phosphocholines

Alternative Parents

Substituents

1-acyl-sn-glycero-3-phosphocholine
Phosphocholine
Fatty acid ester
Dialkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Fatty acyl
Alkyl phosphate
Tetraalkylammonium salt
Quaternary ammonium salt
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic salt
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Amine
Alcohol
Organic cation
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

1-O-acyl-sn-glycero-3-phosphocholine(1+) (CHEBI:28468 )

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	1.19	ChemAxon
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	102.29 Å²	ChemAxon
Rotatable Bond Count	24	ChemAxon
Refractivity	143.4 m³·mol⁻¹	ChemAxon
Polarizability	58.63 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

405288

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

460603

PDB ID

Not Available

ChEBI ID

28468

Good Scents ID

Not Available

References

General References

Lindberg J, Ekeroth J, Konradsson P: Efficient synthesis of phospholipids from glycidyl phosphates. J Org Chem. 2002 Jan 11;67(1):194-9. doi: 10.1021/jo010734+. [PubMed:11777459 ]
Neumuller W, Fleer EA, Unger C, Eibl H: Enzymatic acylation of ether and ester lysophospholipids in rat liver microsomes. Lipids. 1987 Nov;22(11):808-12. doi: 10.1007/BF02535535. [PubMed:3444370 ]
LOTUS database [Link]

Showing NP-Card for (2r)-3-(hexadecanoyloxy)-2-hydroxypropoxy(2-(trimethylammonio)ethoxy)phosphinic acid (NP0262685)

MOL for NP0262685 ((2r)-3-(hexadecanoyloxy)-2-hydroxypropoxy(2-(trimethylammonio)ethoxy)phosphinic acid)

3D MOL for NP0262685 ((2r)-3-(hexadecanoyloxy)-2-hydroxypropoxy(2-(trimethylammonio)ethoxy)phosphinic acid)

3D SDF for NP0262685 ((2r)-3-(hexadecanoyloxy)-2-hydroxypropoxy(2-(trimethylammonio)ethoxy)phosphinic acid)

3D-SDF for NP0262685 ((2r)-3-(hexadecanoyloxy)-2-hydroxypropoxy(2-(trimethylammonio)ethoxy)phosphinic acid)

PDB for NP0262685 ((2r)-3-(hexadecanoyloxy)-2-hydroxypropoxy(2-(trimethylammonio)ethoxy)phosphinic acid)

3D PDB for NP0262685 ((2r)-3-(hexadecanoyloxy)-2-hydroxypropoxy(2-(trimethylammonio)ethoxy)phosphinic acid)

SMILES for NP0262685 ((2r)-3-(hexadecanoyloxy)-2-hydroxypropoxy(2-(trimethylammonio)ethoxy)phosphinic acid)

INCHI for NP0262685 ((2r)-3-(hexadecanoyloxy)-2-hydroxypropoxy(2-(trimethylammonio)ethoxy)phosphinic acid)

Structure for NP0262685 ((2r)-3-(hexadecanoyloxy)-2-hydroxypropoxy(2-(trimethylammonio)ethoxy)phosphinic acid)

3D Structure for NP0262685 ((2r)-3-(hexadecanoyloxy)-2-hydroxypropoxy(2-(trimethylammonio)ethoxy)phosphinic acid)