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Human Metabolome Database Version 2.5

 

Showing metabocard for LysoPE(16:0/0:0) (HMDB11503)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2009-01-08 17:23:33
Update Date 2009-05-05 21:07:34
Accession Number HMDB11503
Secondary Accession Numbers Not Available
Common Name LysoPE(16:0/0:0)
Description LysoPE(16:0/0:0) is a lysophosphatidylethanolamine or a lysophospholipid. The term 'lysophospholipid' (LPL) refers to any phospholipid that is missing one of its two O-acyl chains. Thus, LPLs have a free alcohol in either the sn-1 or sn-2 position. The prefix 'lyso-' comes from the fact that lysophospholipids were originally found to be hemolytic however it is now used to refer generally to phospholipids missing an acyl chain. LPLs are usually the result of phospholipase A-type enzymatic activity on regular phospholipids such as phosphatidylcholine or phosphatidic acid, although they can also be generated by the acylation of glycerophospholipids or the phosphorylation of monoacylglycerols. Some LPLs serve important signaling functions such as lysophosphatidic acid. Lysophosphatidylethanolamines (LPEs) can function as plant growth regulators with several diverse uses. (LPEs) are approved for outdoor agricultural use to accelerate ripening and improve the quality of fresh produce. They are also approved for indoor use to preserve stored crops and commercial cut flowers. As a breakdown product of phosphatidylethanolamine (PE), LPE is present in cells of all organisms.
Synonyms
  1. hexadecanoyl-lysophosphatidylethanolamine
  2. Lyso-PE(16:0)
  3. LysoPE(16:0)
  4. Lysophosphatidylethanolamine(16:0)
  5. LPE(16:0)
  6. LPE(16:0/0:0)
  7. Lyso-PE(16:0/0:0)
  8. Lysophosphatidylethanolamine(16:0/0:0)
  9. LysoPE(16:0/0:0)
  10. 1-palmitoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine
Chemical IUPAC Name 1-hexadecanoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine
Chemical Formula C21H44NO7P
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Lipids
Class
  • Phospholipids
Sub Class
  • Lysophosphatidylethanolamines
Family
  • Mammalian Metabolite
Species
  • secondary alcohol
  • primary amine
  • primary aliphatic amine (alkylamine)
  • carboxylic acid ester
  • phosphoric acid ester
Biofunction
—
Application
—
Source
—
Average Molecular Weight 453.550
Monoisotopic Molecular Weight 453.285553
Isomeric SMILES CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(O)(=O)OCCN
Canonical SMILES CCCCCCCCCCCCCCCC(=O)OCC(O)COP(O)(=O)OCCN
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB11503 Link Image
Metagene Link HMDB11503 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/C21H44NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-21(24)27-18-20(23)19-29-30(25,26)28-17-16-22/h20,23H,2-19,22H2,1H3,(H,25,26)/t20-/m1/s1
Synthesis Reference Not Available
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 2.37e-03 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 4.10 [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. Ectonucleotide pyrophosphatase/phosphodiesterase family member 2 precursor
Enzyme 1 [top]
Enzyme 1 ID 5399
Enzyme 1 Name Ectonucleotide pyrophosphatase/phosphodiesterase family member 2 precursor
Enzyme 1 Synonyms
  1. E-NPP 2
  2. Extracellular lysophospholipase D
  3. LysoPLD
  4. Autotaxin
Enzyme 1 Gene Name ENPP2
Enzyme 1 Protein Sequence >Ectonucleotide pyrophosphatase/phosphodiesterase family member 2 precursor 
MARRSSFQSCQIISLFTFAVGVNICLGFTAHRIKRAEGWEEGPPTVLSDSPWTNISGSCK
GRCFELQEAGPPDCRCDNLCKSYTSCCHDFDELCLKTARGWECTKDRCGEVRNEENACHC
SEDCLARGDCCTNYQVVCKGESHWVDDDCEEIKAAECPAGFVRPPLIIFSVDGFRASYMK
KGSKVMPNIEKLRSCGTHSPYMRPVYPTKTFPNLYTLATGLYPESHGIVGNSMYDPVFDA
TFHLRGREKFNHRWWGGQPLWITATKQGVKAGTFFWSVVIPHERRILTILQWLTLPDHER
PSVYAFYSEQPDFSGHKYGPFGPEMTNPLREIDKIVGQLMDGLKQLKLHRCVNVIFVGDH
GMEDVTCDRTEFLSNYLTNVDDITLVPGTLGRIRSKFSNNAKYDPKAIIANLTCKKPDQH
FKPYLKQHLPKRLHYANNRRIEDIHLLVERRWHVARKPLDVYKKPSGKCFFQGDHGFDNK
VNSMQTVFVGYGPTFKYKTKVPPFENIELYNVMCDLLGLKPAPNNGTHGSLNHLLRTNTF
RPTMPEEVTRPNYPGIMYLQSDFDLGCTCDDKVEPKNKLDELNKRLHTKGSTEERHLLYG
RPAVLYRTRYDILYHTDFESGYSEIFLMPLWTSYTVSKQAEVSSVPDHLTSCVRPDVRVS
PSFSQNCLAYKNDKQMSYGFLFPPYLSSSPEAKYDAFLVTNMVPMYPAFKRVWNYFQRVL
VKKYASERNGVNVISGPIFDYDYDGLHDTEDKIKQYVEGSSIPVPTHYYSIITSCLDFTQ
PADKCDGPLSVSSFILPHRPDNEESCNSSEDESKWVEELMKMHTARVRDIEHLTSLDFFR
KTSRSYPEILTLKTYLHTYESEI
Enzyme 1 Number of Residues 863
Enzyme 1 Molecular Weight 99004
Enzyme 1 Theoretical pI 7.39
Enzyme 1 GO Classification
Function
  • binding
  • catalytic activity
  • endonuclease activity
  • hydrolase activity
  • hydrolase activity, acting on ester bonds
  • nuclease activity
  • nucleic acid binding
Process
  • cellular metabolism
  • metabolism
  • nucleobase, nucleoside, nucleotide and nucleic acid metabolism
  • nucleotide metabolism
  • physiological process
Component
—
Enzyme 1 General Function Not Available
Enzyme 1 Specific Function Hydrolyzes lysophospholipids to produce lysophosphatidic acid (LPA) in extracellular fluids. Major substrate is lysophosphatidylcholine. Also can act on sphingosylphosphphorylcholine producing sphingosine-1-phosphate, a modulator of cell motility. Can hydrolyze, in vitro, bis-pNPP, to some extent pNP-TMP, and barely ATP. Involved in several motility- related processes such as angiogenesis and neurite outgrowth. Acts as an angiogenic factor by stimulating migration of smooth muscle cells and microtubule formation. May have a role in induction of parturition. Possible involvement in cell proliferation and adipose tissue development Tumor cell motility-stimulating factor
Enzyme 1 Pathways Not Available
Enzyme 1 Reactions
  • 1-alkyl-sn-glycero-3-phosphoethanolamine + H2O = 1-alkyl-sn-glycerol 3-phosphate + ethanolamine
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • 1-27
Enzyme 1 Transmembrane Regions Not Available
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 537906 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID Q13822 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name ENPP2_HUMAN Link Image
Enzyme 1 PDB ID Not Available
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence >2748 bp 
ATGGCAAGGAGGAGCTCGTTCCAGTCGTGTCAGATAATATCCCTGTTCACTTTTGCCGTT
GGAGTCAGTATCTGCTTAGGATTCACTGCACATCGAATTAAGAGAGCAGAAGGATGGGAG
GAAGGTCCTCCTACAGTGCTATCAGACTCCCCCTGGACCAACATCTCCGGATCTTGCAAG
GGCAGGTGCTTTGAACTTCAAGAGGCTGGACCTCCTGATTGTCGCTGTGACAACTTGTGT
AAGAGCTATACCAGTTGCTGCCATGACTTTGATGAGCTGTGTTTGAAGACAGCCCGTGGC
TGGGAGTGTACTAAGGACAGATGTGGAGAAGTCAGAAATGAAGAAAATGCCTGTCACTGC
TCAGAGGACTGCTTGGCCAGGGGAGACTGCTGTACCAATTACCAAGTGGTTTGCAAAGGA
GAGTCGCATTGGGTTGATGATGACTGTGAGGAAATAAAGGCCGCAGAATGCCCTGCAGGG
TTTGTTCGCCCTCCATTAATCATCTTCTCCGTGGATGGCTTCCGTGCATCATACATGAAG
AAAGGCAGCAAAGTCATGCCTAATATTGAAAAACTAAGGTCTTGTGGCACACACTCTCCC
TACATGAGGCCGGTGTACCCAACTAAAACCTTTCCTAACTTATACACTTTGGCCACTGGG
CTATATCCAGAATCACATGGAATTGTTGGCAATTCAATGTATGATCCTGTATTTGATGCC
ACTTTTCATCTGCGAGGGCGAGAGAAATTTAATCATAGATGGTGGGGAGGTCAACCGCTA
TGGATTACAGCCACCAAGCAAGGGGTGAAAGCTGGAACATTCTTTTGGTCTGTTGTCATC
CCTCACGAGCGGAGAATATTAACCATATTGCGGTGGCTCACCCTGCCAGATCATGAGAGG
CCTTCGGTCTATGCCTTCTATTCTGAGCAACCTGATTTCTCTGGACACAAATATGGCCCT
TTCGGCCCTGAGGAGAGTAGTTATGGCTCACCTTTTACTCCGGCTAAGAGACCTAAGAGG
AAAGTTGCCCCTAAGAGGAGACAGGAAAGACCAGTTGCTCCTCCAAAGAAAAGAAGAAGA
AAAATACATAGGATGGATCATTATGCTGCGGAAACTCGTCAGGACAAAATGACAAATCCT
CTGAGGGAAATCGACAAAATTGTGGGGCAATTAATGGATGGACTGAAACAACTAAAACTG
CGTCGGTGTGTCAACGTCATCTTTGTCGGAGACCATGGAATGGAAGATGTCACATGTGAT
AGAACTGAGTTCTTGAGTAATTACCTAACTAATGTGGATGATATTACTTTAGTGCCTGGA
ACTCTAGGAAGAATTCGATCCAAATTTAGCAACAATGCTAAATATGACCCCAAAGCCATT
ATTGCCAATCTCACGTGTAAAAAACCAGATCAGCACTTTAAGCCTTACTTGAAACAGCAC
CTTCCCAAACGTTTGCACTATGCCAACAACAGAAGAATTGAGGATATCCATTTATTGGTG
GAACGCAGATGGCATGTTGCAAGGAAACCTTTGGATGTTTATAAGAAACCATCAGGAAAA
TGCTTTTTCCAGGGAGACCACGGATTTGATAACAAGGTCAACAGCATGCAGACTGTTTTT
GTAGGTTATGGCCCAACATTTAAGTACAAGACTAAAGTGCCTCCATTTGAAAACATTGAA
CTTTACAATGTTATGTGTGATCTCCTGGGATTGAAGCCAGCTCCTAATAATGGGACCCAT
GGAAGTTTGAATCATCTCCTGCGCACTAATACCTTCAGGCCAACCATGCCAGAGGAAGTT
ACCAGACCCAATTATCCAGGGATTATGTACCTTCAGTCTGATTTTGACCTGGGCTGCACT
TGTGATGATAAGGTAGAGCCAAAGAACAAGTTGGATGAACTCAACAAACGGCTTCATACA
AAAGGGTCTACAGAAGAGAGACACCTCCTCTATGGGCGACCTGCAGTGCTTTATCGGACT
AGATATGATATCTTATATCACACTGACTTTGAAAGTGGTTATAGTGAAATATTCCTAATG
CTACTCTGGACATCATATACTGTTTCCAAACAGGCTGAGGTTTCCAGCGTTCCTGACCAT
CTGACCAGTTGCGTCCGGCCTGATGTCCGTGTTTCTCCGAGTTTCAGTCAGAACTGTTTG
GCCTACAAAAATGATAAGCAGATGTCCTACGGATTCCTCTTTCCTCCTTATCTGAGCTCT
TCACCAGAGGCTAAATATGATGCATTCCTTGTAACCAATATGGTTCCAATGTATCCTGCT
TTCAAACGGGTCTGGAATTATTTCCAAAGGGTATTGGTGAAGAAATATGCTTCGGAAAGA
AATGGAGTTAACGTGATAAGTGGACCAATCTTCGACTATGACTATGATGGCTTACATGAC
ACAGAAGACAAAATAAAACAGTACGTGGAAGGCAGTTCCATTCCTGTTCCAACTCACTAC
TACAGCATCATCACCAGCTGTCTGGATTTCACTCAGCCTGCCGACAAGTGTGACGGCCCT
CTCTCTGTGTCCTCCTTCATCCTGCCTCACCGGCCTGACAACGAGGAGAGCTGCAATAGC
TCAGAGGACGAATCAAAATGGGTAGAAGAACTCATGAAGATGCACACAGCTAGGGTGCGT
GACATTGAACATCTCACCAGCCTGGACTTCTTCCGAAAGACCAGCCGCAGCTACCCAGAA
ATCCTGACACTCAAGACATACCTGCATACATATGAGAGCGAGATTTAA
Enzyme 1 GenBank Gene ID L35594 Link Image
Enzyme 1 GeneCard ID ENPP2 Link Image
Enzyme 1 GenAtlas ID ENPP2 Link Image
Enzyme 1 HGNC ID HGNC:3357 Link Image
Enzyme 1 Chromosome Location 8
Enzyme 1 Locus 8q24.1
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References
  1. Murata J, Lee HY, Clair T, Krutzsch HC, Arestad AA, Sobel ME, Liotta LA, Stracke ML: cDNA cloning of the human tumor motility-stimulating protein, autotaxin, reveals a homology with phosphodiesterases. J Biol Chem. 1994 Dec 2;269(48):30479-84. [PubMed Link Image]
  2. Lee HY, Murata J, Clair T, Polymeropoulos MH, Torres R, Manrow RE, Liotta LA, Stracke ML: Cloning, chromosomal localization, and tissue expression of autotaxin from human teratocarcinoma cells. Biochem Biophys Res Commun. 1996 Jan 26;218(3):714-9. [PubMed Link Image]
  3. Kawagoe H, Soma O, Goji J, Nishimura N, Narita M, Inazawa J, Nakamura H, Sano K: Molecular cloning and chromosomal assignment of the human brain-type phosphodiesterase I/nucleotide pyrophosphatase gene (PDNP2). Genomics. 1995 Nov 20;30(2):380-4. [PubMed Link Image]
Enzyme 1 Metabolite References Not Available