Human Metabolome Database Version 3.5

Showing metabocard for PS(14:0/16:1(9Z)) (HMDB12333)

Record Information
Version 3.5
Creation Date 2009-06-16 12:11:05 -0600
Update Date 2013-02-08 17:28:50 -0700
HMDB ID HMDB12333
Secondary Accession Numbers None
Metabolite Identification
Common Name PS(14:0/16:1(9Z))
Description PS(14:0/16:1(9Z)) is a phosphatidylserine (PS or GPSer). It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoserines 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. PS(14:0/16:1(9Z)), in particular, consists of one chain of myristic acid at the C-1 position and one chain of palmitoleic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the palmitoleic acid moiety is derived from animal fats and vegetable oils. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. It is usually less than 10% of the total phospholipids, the greatest concentration being in myelin from brain tissue. However, it may comprise 10 to 20 mol% of the total phospholipid in the plasma membrane and endoplasmic reticulum of the cell. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.e. the phosphate moiety, the amino group and the carboxyl function. As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate to calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine, especially during bone formation for example. As phosphatidylserine is located entirely on the inner monolayer surface of the plasma membrane (and of other cellular membranes) and it is the most abundant anionic phospholipids. Therefore phosphatidylseriine may make the largest contribution to interfacial effects in membranes involving non-specific electrostatic interactions. This normal distribution is disturbed during platelet activation and cellular apoptosis. In human plasma, 1-stearoyl-2-oleoyl and 1-stearoyl-2-arachidonoyl species predominate, but in brain (especially grey matter), retina and many other tissues 1-stearoyl-2-docosahexaenoyl species are very abundant. Indeed, the ratio of n-3 to n-6 fatty acids in brain phosphatidylserine is very much higher than in most other lipids. 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. Phosphatidylserines typically carry a net charge of -1 at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1-Myristoyl-2-palmitoleoyl-sn-glycero-3-phosphoserine
  2. Phosphatidylserine(14:0/16:1)
  3. Phosphatidylserine(14:0/16:1n7)
  4. Phosphatidylserine(14:0/16:1w7)
  5. Phosphatidylserine(30:1)
  6. PS(14:0/16:1)
  7. PS(14:0/16:1n7)
  8. PS(14:0/16:1w7)
  9. PS(30:1)
  10. PSer(14:0/16:1)
  11. PSer(14:0/16:1n7)
  12. PSer(14:0/16:1w7)
  13. PSer(30:1)
Chemical Formula C36H68NO10P
Average Molecular Weight 705.8996
Monoisotopic Molecular Weight 705.458083913
IUPAC Name (2S)-2-amino-3-({[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(tetradecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acid
Traditional IUPAC Name (2S)-2-amino-3-{[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(tetradecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}propanoic acid
CAS Registry Number Not Available
SMILES [H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCC)C(O)=O
InChI Identifier InChI=1S/C36H68NO10P/c1-3-5-7-9-11-13-15-16-18-20-22-24-26-28-35(39)47-32(30-45-48(42,43)46-31-33(37)36(40)41)29-44-34(38)27-25-23-21-19-17-14-12-10-8-6-4-2/h13,15,32-33H,3-12,14,16-31,37H2,1-2H3,(H,40,41)(H,42,43)/b15-13-/t32-,33+/m1/s1
InChI Key DPYXPLKOAXFWHZ-BKTZGLHTSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Glycerophospholipids
Sub Class Glycerophosphoserines
Other Descriptors
  • Aliphatic Acyclic Compounds
Substituents
  • Acyclic Alkene
  • Alpha Amino Acid Or Derivative
  • Carboxylic Acid
  • Carboxylic Acid Ester
  • Fatty Acid Ester
  • Organic Hypophosphite
  • Organic Phosphite
  • Phosphoethanolamine
  • Phosphoric Acid Ester
  • Primary Aliphatic Amine (Alkylamine)
  • Tricarboxylic Acid Derivative
Direct Parent Phosphatidylserines
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Energy source
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane component
  • 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 1.530E-04 g/L ALOGPS
LogP 3.93 ALOGPS
LogP 8.24 ChemAxon
LogS -6.67 ALOGPS
pKa (strongest acidic) 1.47 ChemAxon
pKa (strongest basic) 9.38 ChemAxon
Hydrogen Acceptor Count 7 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 171.68 A2 ChemAxon
Rotatable Bond Count 37 ChemAxon
Refractivity 188.75 ChemAxon
Polarizability 82.09 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location
  • All Tissues
  • Kidney
  • Liver
  • Brain
  • Heart
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
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB028952
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB12333 Link_out
Metagene Link HMDB12333 Link_out
METLIN ID Not Available
PubChem Compound 52926036 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: Group 10 secretory phospholipase A2
Reactions: Not Available
Gene Name: PLA2G10
Uniprot ID: O15496 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Diacylglycerol kinase gamma
Reactions: Not Available
Gene Name: DGKG
Uniprot ID: P49619 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Diacylglycerol kinase alpha
Reactions: Not Available
Gene Name: DGKA
Uniprot ID: P23743 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Diacylglycerol kinase delta
Reactions: Not Available
Gene Name: DGKD
Uniprot ID: Q16760 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Diacylglycerol kinase beta
Reactions: Not Available
Gene Name: DGKB
Uniprot ID: Q9Y6T7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Protein kinase C alpha type
Reactions: Not Available
Gene Name: PRKCA
Uniprot ID: P17252 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IA
Reactions: Not Available
Gene Name: ATP8A1
Uniprot ID: Q9Y2Q0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipid scramblase 1
Reactions: Not Available
Gene Name: PLSCR1
Uniprot ID: O15162 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylserine synthase 1
Reactions: Not Available
Gene Name: PTDSS1
Uniprot ID: P48651 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Scavenger receptor class B member 1
Reactions: Not Available
Gene Name: SCARB1
Uniprot ID: Q8WTV0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: C-X-C motif chemokine 16
Reactions: Not Available
Gene Name: CXCL16
Uniprot ID: Q9H2A7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylserine decarboxylase proenzyme
Reactions: Not Available
Gene Name: PISD
Uniprot ID: Q9UG56 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Bifunctional arginine demethylase and lysyl-hydroxylase JMJD6
Reactions: Not Available
Gene Name: JMJD6
Uniprot ID: Q6NYC1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylserine synthase 2
Reactions: Not Available
Gene Name: PTDSS2
Uniprot ID: Q9BVG9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 2-acylglycerol O-acyltransferase 2
Reactions: Not Available
Gene Name: MOGAT2
Uniprot ID: Q3SYC2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol-4-phosphate 3-kinase C2 domain-containing subunit alpha
Reactions: Not Available
Gene Name: PIK3C2A
Uniprot ID: O00443 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 2
Reactions: Not Available
Gene Name: INPPL1
Uniprot ID: O15357 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase delta-3
Reactions: Not Available
Gene Name: PLCD3
Uniprot ID: Q8N3E9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sphingomyelin phosphodiesterase 3
Reactions: Not Available
Gene Name: SMPD3
Uniprot ID: Q9NY59 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipid scramblase 2
Reactions: Not Available
Gene Name: PLSCR2
Uniprot ID: Q9NRY7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipid scramblase 3
Reactions: Not Available
Gene Name: PLSCR3
Uniprot ID: Q9NRY6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipid scramblase 4
Reactions: Not Available
Gene Name: PLSCR4
Uniprot ID: Q9NRQ2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipid scramblase family member 5
Reactions: Not Available
Gene Name: PLSCR5
Uniprot ID: A0PG75 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipase A1 member A
Reactions: Not Available
Gene Name: PLA1A
Uniprot ID: Q53H76 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Serum deprivation-response protein
Reactions: Not Available
Gene Name: SDPR
Uniprot ID: O95810 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Transcriptional regulator ATRX
Reactions: Not Available
Gene Name: ATRX
Uniprot ID: P46100 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Copine-1
Reactions: Not Available
Gene Name: CPNE1
Uniprot ID: Q99829 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Copine-6
Reactions: Not Available
Gene Name: CPNE6
Uniprot ID: O95741 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cdc42-interacting protein 4
Reactions: Not Available
Gene Name: TRIP10
Uniprot ID: Q15642 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Formin-binding protein 1-like
Reactions: Not Available
Gene Name: FNBP1L
Uniprot ID: Q5T0N5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Formin-binding protein 1
Reactions: Not Available
Gene Name: FNBP1
Uniprot ID: Q96RU3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sphingomyelin phosphodiesterase 4
Reactions: Not Available
Gene Name: SMPD4
Uniprot ID: Q9NXE4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Serine incorporator 1
Reactions: Not Available
Gene Name: SERINC1
Uniprot ID: Q9NRX5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Protein kinase C delta-binding protein
Reactions: Not Available
Gene Name: PRKCDBP
Uniprot ID: Q969G5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Annexin A9
Reactions: Not Available
Gene Name: ANXA9
Uniprot ID: O76027 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylserine receptor transcript variant 2
Reactions: Not Available
Gene Name: JMJD6
Uniprot ID: B2WTI4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Serine incorporator 5
Reactions: Not Available
Gene Name: SERINC5
Uniprot ID: Q86VE9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Adseverin
Reactions: Not Available
Gene Name: SCIN
Uniprot ID: Q9Y6U3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Serine incorporator 4
Reactions: Not Available
Gene Name: SERINC4
Uniprot ID: A6NH21 Link_out
Protein Sequence: FASTA
Name: Phosphatidylserine receptor transcript variant 1
Reactions: Not Available
Gene Name: JMJD6
Uniprot ID: B2WTI3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lactadherin
Reactions: Not Available
Gene Name: MFGE8
Uniprot ID: Q08431 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA