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Human Metabolome Database Version 2.5

 

Showing metabocard for PG(16:0/16:0) (HMDB10570)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2008-09-25 14:33:46
Update Date 2009-09-08 14:50:08
Accession Number HMDB10570
Secondary Accession Numbers Not Available
Common Name PG(16:0/16:0)
Description PG(16:0/16:0) is a phosphatidylglycerol or glycerophospholipid (PG or GP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PG(16:0/16:0), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of palmitic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats. Phosphatidylglycerol is present at a level of 1-2% in most animal tissues, but it can be the second most abundant phospholipid in lung surfactant at up to 11% of the total. It is well established that the concentration of phosphatidylglycerol increases during fetal development. Phosphatidylglycerol may be present in animal tissues merely as a precursor for diphosphatidylglycerol (cardiolipin). Phosphatidylglycerol is formed from phosphatidic acid by a sequence of enzymatic reactions that proceeds via the intermediate, cytidine diphosphate diacylglycerol (CDP-diacylglycerol). Bioynthesis proceeds by condensation of phosphatidic acid and cytidine triphosphate with elimination of pyrophosphate via the action of phosphatidate cytidyltransferase (or CDP-synthase). CDP-diacylglycerol then reacts with glycerol-3-phosphate via phosphatidylglycerophosphate synthase to form 3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid, with the release of cytidine monophosphate (CMP). Finally, phosphatidylglycerol is formed by the action of specific phosphatases. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PGs have a net charge of -1 at physiological pH and are found in high concentration in mitochondrial membranes and as components of pulmonary surfactant. PG also serves as a precursor for the synthesis of cardiolipin. PG is synthesized from CDP-diacylglycerol and glycerol-3-phosphate.
Synonyms
  1. PG(32:0)
  2. PG(16:0/16:0)
  3. GPG(32:0)
  4. Phosphatidylglycerol(16:0/16:0)
  5. Phosphatidylglycerol(32:0)
  6. 1,2-dihexadecanoyl-rac-glycero-3-phospho-(1'-rac-glycerol)
  7. GPG(16:0/16:0)
  8. 1,2-dipalmitoyl-rac-glycero-3-phosphoglycerol
Chemical IUPAC Name 1,2-dihexadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol)
Chemical Formula C38H75O10P
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Lipids
Class
  • Phospholipids
Sub Class
  • Phosphatidylglycerols
Family
  • Mammalian Metabolite
Species
  • primary alcohol
  • secondary alcohol
  • 1,2-diol
  • carboxylic acid ester
  • phosphoric acid ester
Biofunction
  • Membrane component
  • Energy source
  • Cell signaling
Application
—
Source
  • Endogenous
Average Molecular Weight 722.970
Monoisotopic Molecular Weight 722.509766
Isomeric SMILES CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@@H](O)CO)OC(=O)CCCCCCCCCCCCCCC
Canonical SMILES CCCCCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCCCCCCCCCC
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB10570 Link Image
Metagene Link HMDB10570 Link Image
METLIN ID Not Available
PubChem Compound Not Available
PubChem Substance Not Available
ChEBI ID Not Available
CAS Registry Number Not Available
InChI Identifier InChI=1/C38H75O10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-37(41)45-33-36(34-47-49(43,44)46-32-35(40)31-39)48-38(42)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h35-36,39-40H,3-34H2,1-2H3,(H,43,44)/t35-,36+/m0/s1
Synthesis Reference Not Available
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 1.41e-04 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 7.80 [Predicted by ALOGPS] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Not Available
Not Available
Predicted 13C NMR Spectrum Not Available
Not Available
Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Membrane
Biofluid Location Not Available
Tissue Location
Tissue References
All Tissues —
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Associated Disorders Not Available
OMIM ID Not Available
Pathways
Name SMPDB Link KEGG Link
Phospholipid Biosynthesis SMP00025 Link Image map00564 Link Image
General References Not Available
Metabolic Enzymes
  1. Acyl-CoA:lysophosphatidylglycerol acyltransferase 1
Enzyme 1 [top]
Enzyme 1 ID 6421
Enzyme 1 Name Acyl-CoA:lysophosphatidylglycerol acyltransferase 1
Enzyme 1 Synonyms Not Available
Enzyme 1 Gene Name LPGAT1
Enzyme 1 Protein Sequence >Acyl-CoA:lysophosphatidylglycerol acyltransferase 1 
MAITLEEAPWLGWLLVKALMRFAFMVVNNLVAIPSYICYVIILQPLRVLDSKRFWYIEGI
MYKWLLGMVASWGWYAGYTVMEWGEDIKAVSKDEAVMLVNHQATGDVCTLMMCLQDKGLV
VAQMMWLMDHIFKYTNFGIVSLVHGDFFIRQGRSYRDQQLLLLKKHLENNYRSRDRKWIV
LFPEGGFLRKRRETSQAFAKKNNLPFLTNVTLPRSGATKIILNALVAQQKNGSPAGGDAK
ELDSKSKGLQWIIDTTIAYPKAEPIDIQTWILGYRKPTVTHVHYRIFPIKDVPLETDDLT
TWLYQRFVEKEDLLSHFYETGAFPPSKGHKEAVSREMTLSNLWIFLIQSFAFLSGYMWYN
IIQYFYHCLF
Enzyme 1 Number of Residues 370
Enzyme 1 Molecular Weight 43090
Enzyme 1 Theoretical pI 9.24
Enzyme 1 GO Classification
Function
  • acyltransferase activity
  • catalytic activity
  • transferase activity
  • transferase activity, transferring acyl groups
  • transferase activity, transferring groups other than amino-acyl groups
Process
  • metabolism
  • physiological process
Component
—
Enzyme 1 General Function Lipid transport and metabolism
Enzyme 1 Specific Function Lysophoshatidylglycerol (LPG) specific acyltransferase that recognizes various acyl-CoAs and LPGs as substrates but demonstrates a clear preference for long chain saturated fatty acyl-CoAs and oleoyl-CoA as acyl donors. Prefers oleoyl-LPG over palmitoyl-LPG as an acyl receptor and oleoyl-CoA over lauroyl-CoA as an acyl donor
Enzyme 1 Pathways Not Available
Enzyme 1 Reactions Not Available
Enzyme 1 Pfam Domain Function Not Available
Enzyme 1 Signals
  • 1-32
Enzyme 1 Transmembrane Regions Not Available
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 40788908 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID Q92604 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name LGAT1_HUMAN Link Image
Enzyme 1 PDB ID Not Available
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence >1176 bp 
CTCCCAAAGCCCCGGCTGGGGCCCGGCCAGCCCGAGAAAGACAGGACGGAGTCCAGTGTG
AGAATGGCTATAACTTTGGAAGAAGCTCCGTGGCTGGGCTGGCTCTTGGTGAAAGCACTG
ATGAGGTTTGCCTTCATGGTCGTCAACAACCTGGTTGCTATTCCATCCTACATCTGCTAT
GTAATTATACTTCAGCCCCTTCGAGTGCTGGACAGTAAGCGGTTCTGGTATATCGAAGGA
ATCATGTATAAATGGCTTTTAGGAATGGTAGCTTCCTGGGGATGGTATGCTGGATATACA
GTGATGGAATGGGGAGAAGATATTAAAGCAGTTTCAAAAGATGAAGCAGTGATGTTGGTG
AATCATCAGGCAACAGGAGATGTGTGCACACTGATGATGTGCCTCCAGGACAAAGGACTG
GTTGTTGCTCAGATGATGTGGTTGATGGATCATATTTTTAAGTACACAAACTTTGGAATT
GTTTCTCTAGTTCATGGAGACTTCTTTATAAGACAGGGAAGATCTTATCGTGACCAACAG
CTGCTGCTTCTCAAGAAGCACTTAGAAAATAATTACAGGAGCAGAGATCGAAAATGGATT
GTTTTGTTTCCAGAAGGGGGCTTCCTCAGGAAGAGGCGAGAAACAAGTCAGGCATTTGCC
AAGAAAAATAACTTGCCATTTCTTACAAATGTTACTCTGCCAAGGTCTGGGGCAACAAAA
ATTATTTTGAATGCACTTGTAGCACAACAGAAAAATGGAAGTCCAGCAGGAGGAGATGCT
AAAGAATTAGACAGCAAATCAAAAGGCCTCCAGTGGATAATAGATACAACGATAGCTTAT
CCCAAAGCTGAACCTATAGATATTCAAACCTGGATCCTTGGATACAGGAAACCAACAGTC
ACACATGTACATTACAGGATCTTTCCAATTAAAGATGTACCCCTGGAGACTGATGACCTT
ACCACTTGGCTCTATCAGCGGTTTGTTGAAAAAGAAGACCTCTTATCACATTTTTATGAA
ACAGGAGCTTTTCCACCTTCCAAGGGCCATAAGGAAGCTGTTTCCAGGGAGATGACCCTC
AGCAACTTGTGGATATTTCTCATACAGTCTTTTGCATTTTTGTCAGGCTATATGTGGTAC
AACATCATTCAGTATTTTTACCATTGCCTGTTTTAG
Enzyme 1 GenBank Gene ID D86960 Link Image
Enzyme 1 GeneCard ID LPGAT1 Link Image
Enzyme 1 GenAtlas ID LPGAT1 Link Image
Enzyme 1 HGNC ID HGNC:28985 Link Image
Enzyme 1 Chromosome Location 1
Enzyme 1 Locus 1p36.13-q42.3
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References
  1. Nagase T, Seki N, Ishikawa K, Ohira M, Kawarabayasi Y, Ohara O, Tanaka A, Kotani H, Miyajima N, Nomura N: Prediction of the coding sequences of unidentified human genes. VI. The coding sequences of 80 new genes (KIAA0201-KIAA0280) deduced by analysis of cDNA clones from cell line KG-1 and brain. DNA Res. 1996 Oct 31;3(5):321-9, 341-54. [PubMed Link Image]
Enzyme 1 Metabolite References Not Available