NP-MRD: Showing NP-Card for glycerylphosphorylcholine (NP0182351)

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Record Information

Version

2.0

Created at

2022-09-03 21:00:52 UTC

Updated at

2022-09-03 21:00:52 UTC

NP-MRD ID

NP0182351

Secondary Accession Numbers

None

Natural Product Identification

Common Name

glycerylphosphorylcholine

Description

Glycerophosphocholine belongs to the class of organic compounds known as glycerophosphocholines. These are lipids containing a glycerol moiety carrying a phosphocholine at the 3-position. Alpha-GPC rapidly delivers choline to the brain across the blood–brain barrier and is a biosynthetic precursor of acetylcholine. Glycerophosphocholine is an extremely weak basic (essentially neutral) compound (based on its pKa). An Italian multicentre clinical trial on 2,044 patients suffering from recent stroke were supplied alpha-GPC in doses of 1,000 mg/day for 28 days and 400 mg three times per day for the five ensuing months. L-Alpha glycerylphosphorylcholine (alpha-GPC, choline alfoscerate) is a natural choline compound found in the brain. Glycerophosphocholine exists in both E. Coli (prokaryote) and yeast (eukaryote). Within humans, glycerophosphocholine participates in a number of enzymatic reactions. In particular, glycerophosphocholine can be biosynthesized from 11-cis-retinol and PC(24:1(15Z)/15:0) Through its interaction with the enzyme lecithin retinol acyltransferase. In addition, retinyl ester and glycerophosphocholine can be biosynthesized from vitamin a and PC(24:1(15Z)/15:0); Which is mediated by the enzyme lecithin retinol acyltransferase. Industrially, alpha-GPC is produced by the chemical or enzymatic deacylation of phosphatidylcholine enriched soya phospholipids followed by chromatographic purification. In humans, glycerophosphocholine is involved in retinol metabolism. It is a non-prescription drug in most countries. It is also a parasympathomimetic acetylcholine precursor which has been investigated for its potential for the treatment of Alzheimer's disease and other dementias. The trial confirmed the therapeutic role of alpha-GPC on the cognitive recovery of patients based on four measurement scales, three of which reached statistical significance. glycerylphosphorylcholine is found in Arabidopsis thaliana. Alpha-GPC may also be derived in small amounts from highly purified soy lecithin as well from purified sunflower lecithin.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 36  0  0  0  0  0  0  0  0999 V2000
   -3.2098   -1.0625    1.0263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1183   -0.2261   -0.1217 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.1679    1.1815    0.2770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3372   -0.4367   -0.9035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9934   -0.4063   -0.9669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9405   -1.3488   -0.4761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3047   -0.9496    0.6807 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9412    0.1443    0.4354 P   0  0  1  0  0  5  0  0  0  0  0  0
    0.3112    1.4920    0.1326 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7427    0.3151    1.9282 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0243   -0.3306   -0.7563 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6741    0.7934   -1.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8072    1.2212   -0.3835 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7843    1.8857   -1.1279 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3588   -0.0097    0.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6344   -0.3152   -0.1865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4056   -1.7902    1.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1628   -1.6491    1.0717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2262   -0.4300    1.9501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3040    1.7492   -0.6771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2280    1.5172    0.7371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0583    1.3322    0.9367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4970   -1.5237   -0.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1614    0.0001   -0.2995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2497    0.0738   -1.8795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4736    0.5617   -1.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3086   -0.7813   -1.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3152   -2.4010   -0.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1509   -1.3720   -1.2717 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9440   -0.5786    2.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0802    0.4952   -2.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9539    1.6319   -1.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3946    1.9140    0.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0096    1.3230   -1.9144 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4290    0.1669    1.3807 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7141   -0.8902    0.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8097   -1.2967   -0.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  8  7  1  1
  8 10  1  0
  8  9  2  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
 10 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  1
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
M  CHG  1   2   1
M  END


  Mrv0541 02231217492D          

 16 15  0  0  1  0            999 V2000
    4.2355    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.5375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3625    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    2.4454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079    2.8579    0.0000 P   0  0  2  0  0  0  0  0  0  0  0  0
    8.2204    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3954    3.5724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    3.2704    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.9513    4.0954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802    3.2704    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
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  1  0  0  0
  8 10  2  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  CHG  1   2   1
M  END
> <DATABASE_ID>
NP0182351

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[N+](C)(C)CCO[P@](O)(=O)OC[C@H](O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C8H20NO6P/c1-9(2,3)4-5-14-16(12,13)15-7-8(11)6-10/h8,10-11H,4-7H2,1-3H3/p+1/t8-/m1/s1

> <INCHI_KEY>
SUHOQUVVVLNYQR-MRVPVSSYSA-O

> <FORMULA>
C8H21NO6P

> <MOLECULAR_WEIGHT>
258.2292

> <EXACT_MASS>
258.110648921

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
25.11246689922053

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R)-2,3-dihydroxypropoxy][2-(trimethylazaniumyl)ethoxy]phosphinic acid

> <ALOGPS_LOGP>
-2.46

> <JCHEM_LOGP>
-5.728311425471745

> <ALOGPS_LOGS>
-1.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.641245557329462

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8553451472945346

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9689647678822215

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
69.804

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.04e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
glycerylphosphorylcholine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       7.906   6.105   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       9.240   5.335   0.000  0.00  0.00           N+1
HETATM    3  C   UNK     0       8.470   4.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.010   6.668   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.574   4.565   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.907   5.335   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      13.241   4.565   0.000  0.00  0.00           O+0
HETATM    8  P   UNK     0      14.575   5.335   0.000  0.00  0.00           P+0
HETATM    9  O   UNK     0      15.345   4.001   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      13.805   6.668   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      15.908   6.105   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      17.242   5.335   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.576   6.105   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      18.576   7.645   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      19.909   5.335   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      21.243   6.105   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

View in JSmol

Synonyms

Value	Source
Choline alfoscerate	MeSH
Choline glycerophosphate	MeSH
Glycerol 3 phosphocholine	MeSH
Glycerol 3-phosphocholine	MeSH
3-Phosphocholine, glycerol	MeSH
Alphoscerate, choline	MeSH
Glycerophosphorylcholine	MeSH
L-alpha-Glycerylphosphorylcholine	MeSH
Alfoscerate, choline	MeSH
Choline alphoscerate	MeSH
Glycerophosphate, choline	MeSH
Glycerylphosphorylcholine	MeSH
L alpha Glycerylphosphorylcholine	MeSH
Glycerophosphocholine	KEGG

Chemical Formula

C₈H₂₁NO₆P

Average Mass

258.2292 Da

Monoisotopic Mass

258.11065 Da

IUPAC Name

[(2R)-2,3-dihydroxypropoxy][2-(trimethylazaniumyl)ethoxy]phosphinic acid

Traditional Name

glycerylphosphorylcholine

CAS Registry Number

Not Available

SMILES

C[N+](C)(C)CCO[P@](O)(=O)OC[C@H](O)CO

InChI Identifier

InChI=1S/C8H20NO6P/c1-9(2,3)4-5-14-16(12,13)15-7-8(11)6-10/h8,10-11H,4-7H2,1-3H3/p+1/t8-/m1/s1

InChI Key

SUHOQUVVVLNYQR-MRVPVSSYSA-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
Arabidopsis thaliana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycerophosphocholines. These are lipids containing a glycerol moiety carrying a phosphocholine at the 3-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphocholines

Direct Parent

Glycerophosphocholines

Alternative Parents

Substituents

Glycero-3-phosphocholine
Phosphocholine
Dialkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Tetraalkylammonium salt
Quaternary ammonium salt
1,2-diol
Secondary alcohol
Organic nitrogen compound
Alcohol
Organic salt
Hydrocarbon derivative
Primary alcohol
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Amine
Organic cation
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	-2.5	ALOGPS
logP	-5.7	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	69.8 m³·mol⁻¹	ChemAxon
Polarizability	25.11 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

C00670

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Alpha-GPC

METLIN ID

Not Available

PubChem Compound

439285

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for glycerylphosphorylcholine (NP0182351)

MOL for NP0182351 (glycerylphosphorylcholine)

3D MOL for NP0182351 (glycerylphosphorylcholine)

3D SDF for NP0182351 (glycerylphosphorylcholine)

3D-SDF for NP0182351 (glycerylphosphorylcholine)

PDB for NP0182351 (glycerylphosphorylcholine)

3D PDB for NP0182351 (glycerylphosphorylcholine)

SMILES for NP0182351 (glycerylphosphorylcholine)

INCHI for NP0182351 (glycerylphosphorylcholine)

Structure for NP0182351 (glycerylphosphorylcholine)

3D Structure for NP0182351 (glycerylphosphorylcholine)