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Human Metabolome Database Version 3.5

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Showing metabocard for PA(P-16:0e/18:2(9Z,12Z)) (HMDB11155)

Record Information
Version 3.5
Creation Date 2008-10-29 09:02:15 -0600
Update Date 2013-02-08 17:25:48 -0700
HMDB ID HMDB11155
Secondary Accession Numbers None
Metabolite Identification
Common Name PA(P-16:0e/18:2(9Z,12Z))
Description 2-(9Z,12Z-octadecadienoyl)-1-(1Z-hexadecenyl)-sn-glycero-3-phosphate is an intermediate of ether lipid metabolism. Ether lipids are lipids in which one or more of the carbon atoms on glycerol is bonded to an alkyl chain via an ether linkage, as opposed to the usual ester linkage. 2-(9Z,12Z-octadecadienoyl)-1-(1Z-hexadecenyl)-sn-glycero-3-phosphate is irreversibly produced from 2-(9Z,12Z-octadecadienoyl)-1-(1Z-hexadecenyl))-sn-glycero-3-phosphoethanolamine via the enzyme phospholipase D (EC: 3.1.4.4). Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 2-(9Z,12Z-Octadecadienoyl)-1-(1Z-hexadecenyl)-sn-glycero-3-phosphate
Chemical Formula C37H69O7P
Average Molecular Weight 656.9133
Monoisotopic Molecular Weight 656.478091074
IUPAC Name [(2R)-3-[(1Z)-hexadec-1-en-1-yloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphonic acid
Traditional IUPAC Name (2R)-3-[(1Z)-hexadec-1-en-1-yloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxyphosphonic acid
CAS Registry Number Not Available
SMILES CCCCCCCCCCCCCC\C=C/OC[C@]([H])(COP(=O)(O)O)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC
InChI Identifier InChI=1S/C37H69O7P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-37(38)44-36(35-43-45(39,40)41)34-42-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h11,13,17,19,31,33,36H,3-10,12,14-16,18,20-30,32,34-35H2,1-2H3,(H2,39,40,41)/b13-11-,19-17-,33-31-/t36-/m1/s1
InChI Key OLCTYLMZTXKGKH-BBNWHMLASA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acid Esters
Sub Class N/A
Other Descriptors
  • Aliphatic Acyclic Compounds
Substituents
  • Acyclic Alkene
  • Carboxylic Acid Ester
  • Enol Ether
  • Organic Hypophosphite
  • Organic Phosphite
  • Phosphoric Acid Ester
Direct Parent Fatty Acid Esters
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
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
Water Solubility 8.320E-05 g/L ALOGPS
LogP 9.27 ALOGPS
LogP 12.44 ChemAxon
LogS -6.90 ALOGPS
pKa (strongest acidic) 1.32 ChemAxon
pKa (strongest basic) -4.7 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 102.29 A2 ChemAxon
Rotatable Bond Count 35 ChemAxon
Refractivity 190.35 ChemAxon
Polarizability 79.89 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB027930
KNApSAcK ID Not Available
Chemspider ID 24766521 Link_out
KEGG Compound ID C15647 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB11155 Link_out
Metagene Link HMDB11155 Link_out
METLIN ID Not Available
PubChem Compound 52929743 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available
Enzymes
Name: Phospholipase D2
Reactions:
  • a phosphatidylcholine + H2O = choline + a phosphatidate [RN:R01310]
Gene Name: PLD2
Uniprot ID: O14939 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Diacylglycerol kinase gamma
Reactions:
  • ATP + 1,2-diacyl-sn-glycerol = ADP + 1,2-diacyl-sn-glycerol 3-phosphate [RN:R02240]
Gene Name: DGKG
Uniprot ID: P49619 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lipid phosphate phosphohydrolase 2
Reactions:
  • a 1,2-diacylglycerol 3-phosphate + H2O = a 1,2-diacyl-sn-glycerol + phosphate [RN:R02239]
Gene Name: PPAP2C
Uniprot ID: O43688 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lipid phosphate phosphohydrolase 1
Reactions:
  • a 1,2-diacylglycerol 3-phosphate + H2O = a 1,2-diacyl-sn-glycerol + phosphate [RN:R02239]
Gene Name: PPAP2A
Uniprot ID: O14494 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lipid phosphate phosphohydrolase 3
Reactions:
  • a 1,2-diacylglycerol 3-phosphate + H2O = a 1,2-diacyl-sn-glycerol + phosphate [RN:R02239]
Gene Name: PPAP2B
Uniprot ID: O14495 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipase DDHD1
Reactions:
    Gene Name: DDHD1
    Uniprot ID: Q8NEL9 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: cAMP-specific 3',5'-cyclic phosphodiesterase 4D
    Reactions:
    • nucleoside 3',5'-cyclic phosphate + H2O = nucleoside 5'-phosphate [RN:R03259]
    Gene Name: PDE4D
    Uniprot ID: Q08499 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Probable phospholipid-transporting ATPase IG
    Reactions:
    • ATP + H2O + phospholipidin = ADP + phosphate + phospholipidout [RN:R00086]
    Gene Name: ATP11C
    Uniprot ID: Q8NB49 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Probable phospholipid-transporting ATPase IH
    Reactions:
    • ATP + H2O + phospholipidin = ADP + phosphate + phospholipidout [RN:R00086]
    Gene Name: ATP11A
    Uniprot ID: P98196 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Probable phospholipid-transporting ATPase VA
    Reactions:
    • ATP + H2O + phospholipidin = ADP + phosphate + phospholipidout [RN:R00086]
    Gene Name: ATP10A
    Uniprot ID: O60312 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Probable phospholipid-transporting ATPase IC
    Reactions:
    • ATP + H2O + phospholipidin = ADP + phosphate + phospholipidout [RN:R00086]
    Gene Name: ATP8B1
    Uniprot ID: O43520 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Probable phospholipid-transporting ATPase IIA
    Reactions:
    • ATP + H2O + phospholipidin = ADP + phosphate + phospholipidout [RN:R00086]
    Gene Name: ATP9A
    Uniprot ID: O75110 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Probable phospholipid-transporting ATPase VD
    Reactions:
    • ATP + H2O + phospholipidin = ADP + phosphate + phospholipidout [RN:R00086]
    Gene Name: ATP10D
    Uniprot ID: Q9P241 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Probable phospholipid-transporting ATPase IB
    Reactions:
    • ATP + H2O + phospholipidin = ADP + phosphate + phospholipidout [RN:R00086]
    Gene Name: ATP8A2
    Uniprot ID: Q9NTI2 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Probable phospholipid-transporting ATPase IA
    Reactions:
    • ATP + H2O + phospholipidin = ADP + phosphate + phospholipidout [RN:R00086]
    Gene Name: ATP8A1
    Uniprot ID: Q9Y2Q0 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Probable phospholipid-transporting ATPase IM
    Reactions:
    • ATP + H2O + phospholipidin = ADP + phosphate + phospholipidout [RN:R00086]
    Gene Name: ATP8B4
    Uniprot ID: Q8TF62 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Probable phospholipid-transporting ATPase IF
    Reactions:
    • ATP + H2O + phospholipidin = ADP + phosphate + phospholipidout [RN:R00086]
    Gene Name: ATP11B
    Uniprot ID: Q9Y2G3 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Probable phospholipid-transporting ATPase IK
    Reactions:
    • ATP + H2O + phospholipidin = ADP + phosphate + phospholipidout [RN:R00086]
    Gene Name: ATP8B3
    Uniprot ID: O60423 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: 1-acyl-sn-glycerol-3-phosphate acyltransferase gamma
    Reactions:
    • acyl-CoA + 1-acyl-sn-glycerol 3-phosphate = CoA + 1,2-diacyl-sn-glycerol 3-phosphate [RN:R02241]
    Gene Name: AGPAT3
    Uniprot ID: Q9NRZ7 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: 1-acyl-sn-glycerol-3-phosphate acyltransferase beta
    Reactions:
    • acyl-CoA + 1-acyl-sn-glycerol 3-phosphate = CoA + 1,2-diacyl-sn-glycerol 3-phosphate [RN:R02241]
    Gene Name: AGPAT2
    Uniprot ID: O15120 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: 1-acyl-sn-glycerol-3-phosphate acyltransferase alpha
    Reactions:
    • acyl-CoA + 1-acyl-sn-glycerol 3-phosphate = CoA + 1,2-diacyl-sn-glycerol 3-phosphate [RN:R02241]
    Gene Name: AGPAT1
    Uniprot ID: Q99943 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Arf-GAP with GTPase, ANK repeat and PH domain-containing protein 2
    Reactions:
      Gene Name: AGAP2
      Uniprot ID: Q99490 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Phospholipid transfer protein
      Reactions:
        Gene Name: PLTP
        Uniprot ID: P55058 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: 1-acyl-sn-glycerol-3-phosphate acyltransferase epsilon
        Reactions:
        • acyl-CoA + 1-acyl-sn-glycerol 3-phosphate = CoA + 1,2-diacyl-sn-glycerol 3-phosphate [RN:R02241]
        Gene Name: AGPAT5
        Uniprot ID: Q9NUQ2 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: 2-acylglycerol O-acyltransferase 2
        Reactions:
        • acyl-CoA + 2-acylglycerol = CoA + diacylglycerol [RN:R01368]
        Gene Name: MOGAT2
        Uniprot ID: Q3SYC2 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Diacylglycerol kinase eta
        Reactions:
        • ATP + 1,2-diacyl-sn-glycerol = ADP + 1,2-diacyl-sn-glycerol 3-phosphate [RN:R02240]
        Gene Name: DGKH
        Uniprot ID: Q86XP1 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: 1-phosphatidylinositol-4,5-bisphosphate phosphodiesterase delta-3
        Reactions:
        • 1-phosphatidyl-1D-myo-inositol 4,5-bisphosphate + H2O = 1D-myo-inositol 1,4,5-trisphosphate + diacylglycerol
        Gene Name: PLCD3
        Uniprot ID: Q8N3E9 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: 1-acyl-sn-glycerol-3-phosphate acyltransferase delta
        Reactions:
        • acyl-CoA + 1-acyl-sn-glycerol 3-phosphate = CoA + 1,2-diacyl-sn-glycerol 3-phosphate [RN:R02241]
        Gene Name: AGPAT4
        Uniprot ID: Q9NRZ5 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Diacylglycerol kinase kappa
        Reactions:
        • ATP + 1,2-diacyl-sn-glycerol = ADP + 1,2-diacyl-sn-glycerol 3-phosphate [RN:R02240]
        Gene Name: DGKK
        Uniprot ID: Q5KSL6 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Probable phospholipid-transporting ATPase VB
        Reactions:
        • ATP + H2O + phospholipidin = ADP + phosphate + phospholipidout [RN:R00086]
        Gene Name: ATP10B
        Uniprot ID: O94823 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Probable phospholipid-transporting ATPase ID
        Reactions:
        • ATP + H2O + phospholipidin = ADP + phosphate + phospholipidout [RN:R00086]
        Gene Name: ATP8B2
        Uniprot ID: P98198 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: N-acyl-phosphatidylethanolamine-hydrolyzing phospholipase D
        Reactions:
          Gene Name: NAPEPLD
          Uniprot ID: Q6IQ20 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Lysocardiolipin acyltransferase 1
          Reactions:
          • acyl-CoA + 1-acyl-sn-glycerol 3-phosphate = CoA + 1,2-diacyl-sn-glycerol 3-phosphate [RN:R02241]
          Gene Name: LCLAT1
          Uniprot ID: Q6UWP7 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Lipase member H
          Reactions:
            Gene Name: LIPH
            Uniprot ID: Q8WWY8 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Lipase member I
            Reactions:
              Gene Name: LIPI
              Uniprot ID: Q6XZB0 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Lipid phosphate phosphatase-related protein type 4
              Reactions:
              • a 1,2-diacylglycerol 3-phosphate + H2O = a 1,2-diacyl-sn-glycerol + phosphate [RN:R02239]
              Gene Name: LPPR4
              Uniprot ID: Q7Z2D5 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Lipid phosphate phosphatase-related protein type 5
              Reactions:
                Gene Name: LPPR5
                Uniprot ID: Q32ZL2 Link_out
                Protein Sequence: FASTA
                Gene Sequence: FASTA
                Name: Presqualene diphosphate phosphatase
                Reactions:
                  Gene Name: PPAPDC2
                  Uniprot ID: Q8IY26 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Probable lipid phosphate phosphatase PPAPDC3
                  Reactions:
                    Gene Name: PPAPDC3
                    Uniprot ID: Q8NBV4 Link_out
                    Protein Sequence: FASTA
                    Gene Sequence: FASTA
                    Name: Phosphatidate phosphatase PPAPDC1A
                    Reactions:
                    • a 1,2-diacylglycerol 3-phosphate + H2O = a 1,2-diacyl-sn-glycerol + phosphate [RN:R02239]
                    Gene Name: PPAPDC1A
                    Uniprot ID: Q5VZY2 Link_out
                    Protein Sequence: FASTA
                    Gene Sequence: FASTA
                    Name: Phosphatidate phosphatase PPAPDC1B
                    Reactions:
                    • a 1,2-diacylglycerol 3-phosphate + H2O = a 1,2-diacyl-sn-glycerol + phosphate [RN:R02239]
                    Gene Name: PPAPDC1B
                    Uniprot ID: Q8NEB5 Link_out
                    Protein Sequence: FASTA
                    Gene Sequence: FASTA
                    Name: Arf-GAP with coiled-coil, ANK repeat and PH domain-containing protein 1
                    Reactions:
                      Gene Name: ACAP1
                      Uniprot ID: Q15027 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Rab11 family-interacting protein 2
                      Reactions:
                        Gene Name: RAB11FIP2
                        Uniprot ID: Q7L804 Link_out
                        Protein Sequence: FASTA
                        Gene Sequence: FASTA
                        Name: Acylglycerol kinase, mitochondrial
                        Reactions:
                        • ATP + 1,2-diacyl-sn-glycerol = ADP + 1,2-diacyl-sn-glycerol 3-phosphate [RN:R02240]
                        Gene Name: AGK
                        Uniprot ID: Q53H12 Link_out
                        Protein Sequence: FASTA
                        Gene Sequence: FASTA
                        Name: Phospholipase D1 variant
                        Reactions:
                          Gene Name: Not Available
                          Uniprot ID: Q59EA4 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Arf-GAP with GTPase, ANK repeat and PH domain-containing protein 1
                          Reactions:
                            Gene Name: AGAP1
                            Uniprot ID: Q9UPQ3 Link_out
                            Protein Sequence: FASTA
                            Gene Sequence: FASTA
                            Name: Phospholipase DDHD2
                            Reactions:
                              Gene Name: DDHD2
                              Uniprot ID: O94830 Link_out
                              Protein Sequence: FASTA
                              Gene Sequence: FASTA
                              Name: Oxysterol-binding protein-related protein 2
                              Reactions:
                                Gene Name: OSBPL2
                                Uniprot ID: Q9H1P3 Link_out
                                Protein Sequence: FASTA
                                Gene Sequence: FASTA
                                Name: Oxysterol-binding protein-related protein 1
                                Reactions:
                                  Gene Name: OSBPL1A
                                  Uniprot ID: Q9BXW6 Link_out
                                  Protein Sequence: FASTA
                                  Gene Sequence: FASTA
                                  Name: Arf-GAP with coiled-coil, ANK repeat and PH domain-containing protein 2
                                  Reactions:
                                    Gene Name: ACAP2
                                    Uniprot ID: Q15057 Link_out
                                    Protein Sequence: FASTA
                                    Gene Sequence: FASTA