NP-MRD: Showing NP-Card for alpha-gpc (NP0142812)

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Record Information

Version

2.0

Created at

2022-09-01 21:26:15 UTC

Updated at

2022-09-01 21:26:15 UTC

NP-MRD ID

NP0142812

Secondary Accession Numbers

None

Natural Product Identification

Common Name

alpha-gpc

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). L-Alpha glycerylphosphorylcholine (alpha-GPC, choline alfoscerate) is a natural choline compound found in the brain. 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. Glycerophosphocholine exists in all living species, ranging from bacteria to humans. Alpha-GPC may also be derived in small amounts from highly purified soy lecithin as well from purified sunflower lecithin. 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 the action of 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 catalyzed by the enzyme lecithin retinol acyltransferase. In humans, glycerophosphocholine is involved in retinol metabolism. 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. It is also a parasympathomimetic acetylcholine precursor which has been investigated for its potential for the treatment of Alzheimer's disease and other dementias. It is a non-prescription drug in most countries. alpha-gpc is found in Homo sapiens and Mus musculus. alpha-gpc was first documented in 2012 (PMID: 22098372). The FDA determined that intake of no more than 196.2 Mg/person/day is considered generally recognized as safe (GRAS) (PMID: 25087032) (PMID: 23497994).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 35  0  0  0  0  0  0  0  0999 V2000
   -3.9783    1.6807   -0.8033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1713    0.5036   -0.4450 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.0318    0.5017    0.9792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9599   -0.6565   -0.8231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9452    0.6042   -1.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8903   -0.3642   -0.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6069   -0.1096    0.6712 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5710   -1.1763    1.2472 P   0  0  2  0  0  5  0  0  0  0  0  0
    0.6935   -2.3355    0.3072 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1090   -1.7557    2.7711 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.9977   -0.3196    1.4378 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9362   -0.5932    0.4474 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1447    0.2589    0.7777 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5927   -0.1088    2.0294 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2227    0.1476   -0.2712 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7983    0.5087   -1.5238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1966    1.6819   -1.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3270    2.5811   -0.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8741    1.7696   -0.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0512    0.7410    1.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3541    1.2792    1.3654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8032   -0.5177    1.3590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0242   -0.3928   -0.6425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7454   -0.9103   -1.8711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6855   -1.4892   -0.1339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1660    0.3142   -2.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5996    1.6405   -1.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1995   -1.4073   -0.7615 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0584   -0.2376   -1.2384 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2050   -1.6759    0.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5499   -0.3142   -0.5634 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7798    1.3138    0.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3170   -0.7688    1.9123 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6073   -0.9113   -0.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0670    0.7818    0.0694 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9600   -0.2638   -2.1330 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
  7  8  1  0
  8 10  1  1
  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
 12 30  1  0
 12 31  1  0
 13 32  1  1
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
M  CHG  2   2   1  10  -1
M  END

D-Glycerolphosphocholine.mol
  Mrv0541 02231218202D          

 16 15  0  0  0  0            999 V2000
    2.2539   -0.2062    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    0.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914    0.5082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211   -0.2062    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.4934   -0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6336   -0.9207    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3645    0.2063    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0789   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0789   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3645    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  1  2  1  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  0  0  0  0
  1  6  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 11 12  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  6  0  0  0
  8 11  1  0  0  0  0
  7  8  1  0  0  0  0
  3  7  1  0  0  0  0
M  CHG  2   1   1  10  -1
M  END
> <DATABASE_ID>
NP0142812

> <DATABASE_NAME>
NP-MRD

> <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-/m0/s1

> <INCHI_KEY>
SUHOQUVVVLNYQR-QMMMGPOBSA-N

> <FORMULA>
C8H20NO6P

> <MOLECULAR_WEIGHT>
257.2213

> <EXACT_MASS>
257.102823889

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
24.420859371997068

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{[(2S)-2,3-dihydroxypropyl phosphonato]oxy}ethyl)trimethylazanium

> <ALOGPS_LOGP>
-2.56

> <JCHEM_LOGP>
-5.728311425471745

> <ALOGPS_LOGS>
-1.54

> <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>
99.05000000000001

> <JCHEM_REFRACTIVITY>
68.68230000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.96e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
Alpha-GPC

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: D-Glycerolphosphocholine.mol                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       4.207  -0.385   0.000  0.00  0.00           N+1
HETATM    2  C   UNK     0       2.667  -0.385   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.897   0.949   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.747  -0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.207  -1.925   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.207   1.155   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.357   0.949   0.000  0.00  0.00           O+0
HETATM    8  P   UNK     0      -0.413  -0.385   0.000  0.00  0.00           P+0
HETATM    9  O   UNK     0       0.921  -1.155   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -1.183  -1.719   0.000  0.00  0.00           O-1
HETATM   11  O   UNK     0      -1.746   0.385   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.080  -0.385   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.414   0.385   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.747  -0.385   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -5.747  -1.925   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -4.414   1.925   0.000  0.00  0.00           O+0
CONECT    1    2    4    5    6                                             
CONECT    2    3    1                                                       
CONECT    3    2    7                                                       
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    1                                                            
CONECT    7    8    3                                                       
CONECT    8    9   10   11    7                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11   12    8                                                       
CONECT   12   13   11                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

View in JSmol

Synonyms

Value	Source
2-[[(2,3-Dihydroxypropoxy)hydroxyphosphinyl]oxy]-N,N,N-trimethyl-ethanaminium inner salt	HMDB
a-Glycerophosphorylcholine	HMDB
a-Glycerylphosphorylcholine	HMDB
alpha-Glycerophosphorylcholine	HMDB
alpha-Glycerylphosphorylcholine	HMDB
Choline alfoscerate	HMDB, MeSH
Choline glycerophosphate	HMDB
Glycerol 3-phosphocholine	HMDB, MeSH
Glycerol phosphorylcholine	HMDB
Glycerol-3-phosphatidylcholine	HMDB
Glycerophosphatidylcholine	HMDB
Glycerophosphorylcholine	HMDB, MeSH
GPC	HMDB
GPCho	HMDB
Hydrogen glycerophosphate choline	HMDB
L-alpha-Glycerophosphocholine	HMDB
L-alpha-Glycerophosphorylcholine	HMDB
L-alpha-Glycerylphosphorylcholine	HMDB, MeSH
L-Choline hydroxide 2,3-dihydroxypropyl hydrogen phosphate inner salt	HMDB
sn-glycero-3-Phosphocholine	HMDB
Alfoscerate, choline	MeSH, HMDB
Choline alphoscerate	MeSH, HMDB
Glycerophosphate, choline	MeSH, HMDB
Alphoscerate, choline	MeSH, HMDB
L alpha Glycerylphosphorylcholine	MeSH, HMDB
3-Phosphocholine, glycerol	MeSH, HMDB
Glycerol 3 phosphocholine	MeSH, HMDB
Glycerylphosphorylcholine	MeSH, HMDB
Cereton	HMDB
Cholicerin	HMDB
Cholitiline	HMDB
Delecit	HMDB
Gliatilin	HMDB
Glycerol 3-phosphorylcholine	HMDB
Glycerophosphocholine	HMDB
Glycerophosphoric acid choline ester	HMDB
Glyceryl 3-phosphorylcholine	HMDB
Glycerylphosphocholine	HMDB
L-alpha-GPC	HMDB
L-α-GPC	HMDB
L-α-Glycerophosphocholine	HMDB
L-α-Glycerophosphorylcholine	HMDB
L-α-Glycerylphosphorylcholine	HMDB
O-(sn-glycero-3-Phosphoryl)-choline	HMDB
sn-glycero-3-Phosphorylcholine	HMDB
α-Glycerophosphorylcholine	HMDB
α-Glycerylphosphorylcholine	HMDB

Chemical Formula

C₈H₂₀NO₆P

Average Mass

257.2213 Da

Monoisotopic Mass

257.10282 Da

IUPAC Name

(2-{[(2S)-2,3-dihydroxypropyl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

Alpha-GPC

CAS Registry Number

Not Available

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-/m0/s1

InChI Key

SUHOQUVVVLNYQR-QMMMGPOBSA-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
Homo sapiens	LOTUS Database	35616633
Mus musculus	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
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

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	-2.6	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	24.42 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

HMDB0000086

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

Alpha-GPC

METLIN ID

Not Available

PubChem Compound

71920

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30. [PubMed:25087032 ]
Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9. [PubMed:22098372 ]
Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15. [PubMed:23497994 ]
LOTUS database [Link]

Showing NP-Card for alpha-gpc (NP0142812)

MOL for NP0142812 (alpha-gpc)

3D MOL for NP0142812 (alpha-gpc)

3D SDF for NP0142812 (alpha-gpc)

3D-SDF for NP0142812 (alpha-gpc)

PDB for NP0142812 (alpha-gpc)

3D PDB for NP0142812 (alpha-gpc)

SMILES for NP0142812 (alpha-gpc)

INCHI for NP0142812 (alpha-gpc)

Structure for NP0142812 (alpha-gpc)

3D Structure for NP0142812 (alpha-gpc)