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Bovine Metabolome Database



Showing metabocard for Glycerophosphocholine (BMDB00086)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:57:41
Accession Number BMDB00086
Common Name Glycerophosphocholine
Description Glycerophosphorylcholine (GPC) is a choline derivative and one of the two major forms of choline storage (along with phosphocholine) in the cytosol. Glycerophosphorylcholine is also one of the four major organic osmolytes in renal medullary cells, changing their intracellular osmolyte concentration in parallel with extracellular tonicity during cellular osmoadaptation. As an osmolyte, Glycerophosphorylcholine counteracts the effects of urea on enzymes and other macromolecules. Kidneys (especially medullar cells), which are exposed under normal physiological conditions to widely fluctuating extracellular solute concentrations, respond to hypertonic stress by accumulating the organic osmolytes glycerophosphorylcholine (GPC), betaine, myo-inositol, sorbitol and free amino acids. Increased intracellular contents of these osmolytes are achieved by a combination of increased uptake (myo-inositol and betaine) and synthesis (sorbitol, GPC), decreased degradation (GPC) and reduced osmolyte release.
Synonyms
  1. 2-[[(2,3-dihydroxypropoxy)hydroxyphosphinyl]oxy]-N,N,N-trimethyl-Ethanaminium inner salt
  2. Choline Alfoscerate
  3. Choline glycerophosphate
  4. Glycerol 3-phosphocholine
  5. Glycerol phosphorylcholine
  6. Glycerol-3-phosphatidylcholine
  7. Glycerophosphatidylcholine
  8. Glycerophosphocholine
  9. Glycerophosphorylcholine
  10. L-Choline hydroxide 2,3-dihydroxypropyl hydrogen phosphate inner salt
  11. L-alpha-Glycerophosphocholine
  12. L-alpha-Glycerophosphorylcholine
  13. L-alpha-Glycerylphosphorylcholine
  14. a-Glycerophosphorylcholine
  15. a-Glycerylphosphorylcholine
  16. alpha-Glycerophosphorylcholine
  17. hydrogen glycerophosphate Choline
  18. sn-Glycero-3-phosphocholine
  19. alpha-Glycerylphosphorylcholine
  20. GPCho
  21. GPC
Chemical IUPAC Name 2-[[(2R)-2,3-dihydroxypropoxy]-hydroxy-phosphoryl]oxyethyl-trimethyl-azanium
Chemical Formula C8H20NO6P
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Amino acids and Amino Acid conjugates
Class
  • Quaternary Amines
Sub Class
  • Short chain acyl carnitines
Family
  • Mammalian_Metabolite
Species
  • cation; anion; primary alcohol; secondary alcohol; 1,2-diol; quaternary ammonium salt; phosphoric acid ester
Biofunction
  • Component of Glycerophospholipid metabolism; Component of Prostaglandin and leukotriene metabolism
Application
Source
  • Endogenous
Average Molecular Weight 257.221
Monoisotopic Molecular Weight 257.102814
Isomeric SMILES C[N+](C)(C)CCOP([O-])(=O)OC[C@@H](O)CO
Canonical SMILES C[N+](C)(C)CCOP([O-])(=O)OCC(O)CO
KEGG Compound ID C00670 Link Image
BioCyc ID GLYCERYLPHOSPHORYLCHOLINE Link Image
BiGG ID 35659 Link Image
Wikipedia Link Not Available
METLIN ID 370 Link Image
PubChem Compound 439285 Link Image
PubChem Substance 8026608 Link Image
ChEBI ID 16870 Link Image
CAS Registry Number 28319-77-9
InChI Identifier InChI=1/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
Synthesis Reference Evans, Christopher Thomas; McCague, Raymond; Tyrrell, Nicholas David. Preparation of phospholipid-intermediate glycerophosphocholine by a crystallization process. PCT Int. Appl. (1993), 8 pp.
Melting Point (Experimental) 142.5 oC
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 1000.0 mg/mL [MEYLAN,WM et al. (1996)]; 8.96 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -2.56 [Predicted by ALOGPS]; -5.15 [MEYLAN,WM & HOWARD,PH (1995)] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
Download FID (Varian)
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Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
Download FID (Bruker)
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Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
  • Extracellular
Biofluid Location
  • Breast_Milk
Tissue Location
Tissue References
Brain
Kidney
Most Tissues
Spleen
Concentrations (Normal)
Biofluid Breast_Milk
Value 284 - 1460 uM
Age N/A
Sex N/A
Condition Normal
Comments Raw. skim.
References
Biofluid Breast_Milk
Value 695 +/- 78 uM
Age N/A
Sex N/A
Condition Normal
Comments Quantified by NMR in 2% milk
References
Biofluid Breast_Milk
Value 748 +/- 92 uM
Age N/A
Sex N/A
Condition Normal
Comments Quantified by NMR in 1% milk
References
Biofluid Breast_Milk
Value 644 +/- 218 uM
Age N/A
Sex N/A
Condition Normal
Comments Quantified by NMR in skim milk
References
Biofluid Breast_Milk
Value 849 +/- 20 uM
Age N/A
Sex N/A
Condition Normal
Comments Quantified by NMR in 3.25% milk
References
Concentrations (Abnormal) Not Available
Pathway Names
  • Phospholipid Synthesis
HMDB Pathways
Name Phospholipid Synthesis
Image Show Link Image
KEGG Pathways
Name Phospholipid Synthesis
Image Show Link Image
SimCell Pathways Not Available
General References Not Available
Metabolic Enzymes
  1. Cytosolic phospholipase A2
Enzyme 1 [top]
Enzyme 1 ID 783
Enzyme 1 Name Cytosolic phospholipase A2
Enzyme 1 Synonyms
  1. cPLA2
  2. Phospholipase A2 group IVA
  3. Phospholipase A2
  4. Phosphatidylcholine 2-acylhydrolase
  5. Lysophospholipase
Enzyme 1 Gene Name PLA2G4A
Enzyme 1 Protein Sequence >Cytosolic phospholipase A2
MSFIDPYQHIIVEHHYSHKFTVVVLRATKVTKGTFGDMLDTPDPYVELFISSTPDSRKRT
RHFNNDINPVWNETFEFILDPNQENILEITLMDANYVMDETLGTTTFPISSMKVGEKKQV
PFIFNQVTEMILEMSLEVCSSPDLRFSMALCDQEKAFRQQRKENIKENMKKLLGPKNSEG
LHSTRDVPVVAILGSGGGFRAMVGFSGVMKALYESGILDCATYIAGLSGSTWYMSTLYSH
PDFPEKGPEEINKELMKNVSHNPLLLLTPQKIKRYVESLWRKKSSGQPVTFTDIFGMLIG
ETLIHNRMNTTLSSLKEKVNTGQCPLPLFTCLHVKPDVSELMFADWVEFSPFEIGMAKYG
TFMAPDLFGSKFFMGTVVKKYEENPLHFLMGVWGSAFSILFNRVLGVSGSQSKGSTMEEE
LENITAKHIVSNDSSDSDDESQGPKGTEHEEAEREYQNDNQASWVQRMLMALVSDSALFN
TREGRAGKVHNFMLGLNLNTSYPMSPLRDFTMQESLDEDELDAAVADPDEFEQIYEPLDV
KSKKIHVVDSGLTFNLPYPLILRPQRGVDLIISFDFSARPSDSSPPFKELLLAEKWAKMN
KLPFPKIDPYVFDREGLKECYVFKPKNPDVEKDCPTIIHFVLANINFRKYKAPGVPRETN
EEKEIADFDIFDDPESPFSTFNFQYPNQAFKRLHDLMYFNTLNNIDVIKNAIVESIEYRR
QNPSRCSVSLSSVEARRFFNKEFLSKPTA
Enzyme 1 Number of Residues 749
Enzyme 1 Molecular Weight 85349.6
Enzyme 1 Theoretical pI 5.18
Enzyme 1 GO Classification
Function
Process
Component
Enzyme 1 General Function Involved in calcium ion binding
Enzyme 1 Specific Function Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response
Enzyme 1 Pathways Not Available
Enzyme 1 Reactions Not Available
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • None
Enzyme 1 Transmembrane Regions
  • None
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 38326700 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID A4IFJ5 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name PA24A_BOVIN Link Image
Enzyme 1 PDB ID 1CJY Link Image
Enzyme 1 PDB File Show
Enzyme 1 3D Structure
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence >2250 bp
ATGTCATTTATAGATCCTTATCAACACATTATAGTGGAGCACCATTATTCCCACAAGTTC
ACAGTAGTGGTGCTGCGTGCCACAAAAGTGACAAAGGGAACCTTTGGTGACATGCTTGAC
ACTCCAGACCCCTATGTGGAACTTTTCATCTCTTCAACCCCCGACAGCAGGAAGAGAACA
AGACACTTCAATAATGACATAAACCCTGTGTGGAATGAGACCTTTGAATTTATTTTGGAT
CCTAATCAGGAAAATATTTTGGAGATCACTTTAATGGATGCCAATTATGTTATGGATGAA
ACTCTTGGGACGACAACGTTTCCCATATCTTCTATGAAAGTGGGAGAGAAGAAACAGGTT
CCTTTTATTTTCAATCAAGTCACTGAAATGATTCTGGAAATGTCTCTTGAAGTTTGTTCA
TCCCCAGACCTCCGGTTTAGTATGGCTCTGTGTGACCAGGAGAAAGCTTTCAGACAACAG
AGAAAGGAAAACATAAAGGAAAACATGAAGAAACTGCTGGGTCCAAAGAATAGTGAAGGC
TTGCATTCTACACGTGATGTGCCTGTGGTGGCCATACTGGGCTCAGGTGGGGGATTTCGA
GCCATGGTAGGATTCTCTGGTGTGATGAAGGCACTGTATGAGTCAGGGATTTTGGACTGT
GCTACCTACATTGCTGGTCTTTCTGGATCCACATGGTATATGTCGACCTTATATTCTCAC
CCTGATTTTCCAGAGAAAGGGCCAGAGGAGATTAACAAAGAGCTAATGAAAAATGTCAGC
CACAACCCTCTTTTACTTCTCACACCACAGAAAATTAAAAGATATGTTGAGTCTTTATGG
AGGAAAAAAAGTTCTGGACAACCTGTCACCTTTACTGATATCTTCGGGATGTTAATAGGA
GAAACACTAATTCACAATAGAATGAACACTACCCTGAGTAGTTTGAAGGAAAAAGTCAAT
ACTGGGCAGTGTCCTCTGCCGCTTTTCACCTGTCTCCATGTCAAACCCGATGTCTCAGAG
CTGATGTTTGCAGATTGGGTTGAATTTAGTCCATTTGAGATTGGCATGGCTAAATATGGT
ACTTTTATGGCGCCTGACTTATTTGGAAGCAAATTTTTTATGGGAACAGTTGTAAAGAAA
TACGAAGAAAACCCCTTGCATTTCTTAATGGGTGTCTGGGGTAGTGCCTTTTCTATATTG
TTCAACAGAGTCTTGGGAGTTTCTGGATCACAAAGTAAAGGTTCCACAATGGAAGAAGAA
CTAGAAAATATTACAGCAAAGCATATTGTGAGTAATGATAGCTCAGACAGTGATGACGAA
TCACAAGGACCCAAAGGCACTGAACATGAAGAAGCAGAAAGGGAATACCAAAATGATAAT
CAAGCAAGTTGGGTCCAACGTATGCTCATGGCCTTGGTGAGTGACTCAGCTTTGTTCAAT
ACCAGAGAAGGACGTGCCGGGAAGGTGCACAACTTCATGCTGGGCTTGAATCTCAATACA
TCCTATCCAATGTCTCCTTTGAGAGACTTTACCATGCAAGAGTCCCTGGATGAAGACGAA
TTGGATGCCGCTGTCGCAGATCCTGATGAATTTGAGCAGATATATGAGCCTTTGGATGTC
AAAAGTAAAAAGATTCATGTGGTGGACAGTGGCCTCACATTTAACCTTCCATACCCTTTG
ATCCTGAGACCTCAGAGGGGAGTTGATCTCATCATCTCCTTTGACTTTTCTGCAAGACCA
GGTGACTCCAGTCCTCCGTTCAAGGAACTTCTACTTGCAGAAAAGTGGGCTAAAATGAAC
AAGCTCCCCTTTCCAAAGATTGATCCTTACGTATTCGATCGAGAAGGACTGAAGGAATGC
TATGTTTTTAAACCCAAGAATCCTGATGTCGAGAAAGATTGCCCGACTATCATTCACTTT
GTTCTGGCCAACATCAACTTCAGAAAGTACAAGGCTCCAGGTGTTCCAAGAGAAACTAAT
GAAGAGAAAGAAATAGCTGATTTTGATATTTTTGATGACCCTGAATCACCGTTTTCGACC
TTCAACTTTCAATATCCCAATCAAGCATTTAAAAGGCTGCATGATCTCATGTACTTCAAT
ACCCTGAACAACATTGATGTAATAAAGAATGCTATAGTCGAAAGCATCGAATATAGAAGG
CAGAATCCGTCTCGTTGCTCTGTTTCCCTCAGTAGTGTTGAGGCAAGAAGATTCTTCAAC
AAGGAGTTTCTAAGCAAACCCACAGCATAG
Enzyme 1 GenBank Gene ID AY363688 Link Image
Enzyme 1 GeneCard ID PLA2G4A Link Image
Enzyme 1 GenAtlas ID Not Available
Enzyme 1 HGNC ID Not Available
Enzyme 1 Chromosome Location Chromosome:1
Enzyme 1 Locus 1q25
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References
  1. [PubMed Link Image]
Enzyme 1 Metabolite References Not Available