ChemFOnt: Showing chemical card for L-1-glycero-3-phosphocholine (CFc000337858)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:31:56 UTC

Chemfont ID

CFc000337858

Molecule Identification

Common Name

L-1-glycero-3-phosphocholine

Definition

Choline alfoscerate, also known as glycerophosphocholine or choline glycerophosphate, is a member of the class of compounds known as glycerophosphocholines. Glycerophosphocholines are lipids containing a glycerol moiety carrying a phosphocholine at the 3-position. Choline alfoscerate is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Choline alfoscerate can be found in a number of food items such as radish, strawberry guava, yellow pond-lily, and pepper (c. baccatum), which makes choline alfoscerate a potential biomarker for the consumption of these food products. L-Alpha glycerylphosphorylcholine (alpha-GPC, choline alfoscerate) is a natural choline compound found in the brain. It is also a parasympathomimetic acetylcholine precursor which may have potential for the treatment of Alzheimer's disease and other dementias .

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2R)-2,3-Dihydroxypropyl 2-(trimethylammonio)ethyl phosphate	ChEBI
Alfoscerate de choline	ChEBI
Alfoscerato de colina	ChEBI
alpha-Glycerophosphorylcholine	ChEBI
Choline alphoscerate	ChEBI
Choline glycerophosphate	ChEBI
Cholini alfosceras	ChEBI
Cholini glycerophosphas	ChEBI
Glicerofosfato de colina	ChEBI
Glycerol phosphorylcholine	ChEBI
Glycerol-3-phosphatidylcholine	ChEBI
Glycerol-3-phosphocholine	ChEBI
Glycerophosphate de choline	ChEBI
Glycerophosphorylcholine	ChEBI
GPCho	ChEBI
L-alpha-Glycerophosphocholine	ChEBI
L-alpha-Glycerophosphorylcholine	ChEBI
L-Choline hydroxide 2,3-dihydroxypropyl hydrogen phosphate inner salt	ChEBI
sn-3-GPC	ChEBI
sn-Glycero-3-phosphocholine	ChEBI
sn-Glycerol 3-phosphocholine	ChEBI
Gliatilin	Kegg
(2R)-2,3-Dihydroxypropyl 2-(trimethylammonio)ethyl phosphoric acid	Generator
Alfosceric acid de choline	Generator
a-Glycerophosphorylcholine	Generator
Α-glycerophosphorylcholine	Generator
Choline alphosceric acid	Generator
Choline glycerophosphoric acid	Generator
Glycerophosphoric acid de choline	Generator
L-a-Glycerophosphocholine	Generator
L-Α-glycerophosphocholine	Generator
L-a-Glycerophosphorylcholine	Generator
L-Α-glycerophosphorylcholine	Generator
L-Choline hydroxide 2,3-dihydroxypropyl hydrogen phosphoric acid inner salt	Generator
Choline alfosceric acid	HMDB
Glycerol 3 phosphocholine	HMDB
Glycerylphosphorylcholine	HMDB
Alphoscerate, choline	HMDB
L alpha Glycerylphosphorylcholine	HMDB
3-Phosphocholine, glycerol	HMDB
Glycerol 3-phosphocholine	HMDB
L-alpha-Glycerylphosphorylcholine	HMDB
Alfoscerate, choline	HMDB
Glycerophosphate, choline	HMDB
2-[[(2,3-Dihydroxypropoxy)hydroxyphosphinyl]oxy]-N,N,N-trimethyl-ethanaminium inner salt	HMDB
a-Glycerylphosphorylcholine	HMDB
alpha-Glycerylphosphorylcholine	HMDB
Choline alfoscerate	HMDB
Glycerophosphatidylcholine	HMDB
GPC	HMDB
Hydrogen glycerophosphate choline	HMDB
Cereton	HMDB
Cholicerin	HMDB
Cholitiline	HMDB
Delecit	HMDB
Glycerol 3-phosphorylcholine	HMDB
Glycerophosphoric acid choline ester	HMDB
Glyceryl 3-phosphorylcholine	HMDB
Glycerylphosphocholine	HMDB
L-alpha-GPC	HMDB
L-Α-GPC	HMDB
L-Α-glycerylphosphorylcholine	HMDB
O-(sn-Glycero-3-phosphoryl)-choline	HMDB
sn-Glycero-3-phosphorylcholine	HMDB
Α-glycerylphosphorylcholine	HMDB
Glycerophosphocholine	ChEBI

Chemical Formula

C₈H₂₀NO₆P

Average Molecular Weight

257.223

Monoisotopic Molecular Weight

257.102824366

IUPAC Name

(2-{[(2R)-2,3-dihydroxypropyl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-2,3-dihydroxypropyl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

28319-77-9

SMILES

C[N+](C)(C)CCOP([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/t8-/m1/s1

InChI Key

SUHOQUVVVLNYQR-MRVPVSSYSA-N

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
Organic salt
Hydrocarbon derivative
Primary alcohol
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Amine
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

phosphocholines (CHEBI:16870 )
sn-glycerol 3-phosphates (CHEBI:16870 )

Functional Ontology

Physiological effect

Health effect

Observation

Attachment loss (HMDB: HMDB0000086)
Missing teeth (HMDB: HMDB0000086)
Prosthesis/Missing teeth (HMDB: HMDB0000086)

Intervention

Periodontal Probing Depth (HMDB: HMDB0000086)

Circulatory system disorder

Vascular disorder

Multi-infarct dementia (HMDB: HMDB0000086)

Organoleptic effect

Touch

Smooth (HMDB: HMDB0000086)

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0000086)
Cytoplasm (HMDB: HMDB0000086)
Extracellular (HMDB: HMDB0000086)
Cell membrane (HMDB: HMDB0000086)
Intracellular membrane (HMDB: HMDB0000086)

Non-excretory biofluid

Biofluid or Excreta

Excreta

Biofluid or Excreta

Feces (HMDB: HMDB0000086)

Organ

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000086)

Source

Endogenous

Endogenous (HMDB: HMDB0000086)

Animal

Animal (HMDB: HMDB0000086)

Exogenous

Food

Food (HMDB: HMDB0000086)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)

Herbs and Spices (FooDB: FOOD00866)

Nut

Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Hazelnut (FooDB: FOOD00376)
Peanut (FooDB: FOOD00016)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Nuts (FooDB: FOOD00869)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)
Jujube (FooDB: FOOD00388)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)

Root vegetable

Cabbage

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)

Mushroom

Tuber

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Other vegetable

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000086)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000086)

Lipid metabolism pathway (HMDB: HMDB0000086)

Cellular process

Cell signaling (HMDB: HMDB0000086)

Biochemical process

Lipid transport (HMDB: HMDB0000086)

Role

Biological role

Energy source (HMDB: HMDB0000086)

Industrial application

Food and nutrition

Food additive (HMDB: HMDB0000086)

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000086)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	8.96 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-5.7	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	99.05 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	68.68 m³·mol⁻¹	ChemAxon
Polarizability	24.77 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