Showing metabocard for PS(14:0/16:1(9Z)) (BMDB0012333)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 18:36:21 UTC
Update Date2020-05-21 16:28:16 UTC
BMDB IDBMDB0012333
Secondary Accession Numbers
  • BMDB12333
Metabolite Identification
Common NamePS(14:0/16:1(9Z))
DescriptionPS(14:0/16:1(9Z)), also known as PS(14:0/16:1) or PS(30:1), belongs to the class of organic compounds known as phosphatidylserines. These are glycerophosphoserines in which two fatty acids are bonded to the glycerol moiety through ester linkages. As is the case with diacylglycerols, phosphatidylserines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. Thus, PS(14:0/16:1(9Z)) is considered to be a glycerophosphoserine lipid molecule. PS(14:0/16:1(9Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PS(14:0/16:1(9Z)) exists in all eukaryotes, ranging from yeast to humans. PS(14:0/16:1(9Z)) participates in a number of enzymatic reactions, within cattle. In particular, Choline and PS(14:0/16:1(9Z)) can be biosynthesized from PC(14:0/16:1(9Z)) and L-serine; which is mediated by the enzyme phosphatidylserine synthase. Furthermore, PS(14:0/16:1(9Z)) can be converted into PE(14:0/16:1(9Z)); which is catalyzed by the enzyme phosphatidylserine decarboxylase. Finally, PS(14:0/16:1(9Z)) can be converted into PE(14:0/16:1(9Z)) through the action of the enzyme phosphatidylserine decarboxylase. In cattle, PS(14:0/16:1(9Z)) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(14:0/16:1(9Z)) pathway and phosphatidylcholine biosynthesis PC(14:0/16:1(9Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Myristoyl-2-palmitoleoyl-sn-glycero-3-phosphoserineHMDB
Phosphatidylserine(14:0/16:1)HMDB
Phosphatidylserine(14:0/16:1n7)HMDB
Phosphatidylserine(14:0/16:1W7)HMDB
Phosphatidylserine(30:1)HMDB
PS(14:0/16:1)HMDB
PS(14:0/16:1N7)HMDB
PS(14:0/16:1W7)HMDB
PS(30:1)HMDB
pSer(14:0/16:1)HMDB
pSer(14:0/16:1n7)HMDB
pSer(14:0/16:1W7)HMDB
pSer(30:1)HMDB
1-Tetradecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphoserineHMDB
PS(14:0/16:1(9Z))Lipid Annotator
Chemical FormulaC36H68NO10P
Average Molecular Weight705.911
Monoisotopic Molecular Weight705.458084392
IUPAC Name(2S)-2-amino-3-({[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(tetradecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acid
Traditional Name(2S)-2-amino-3-{[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(tetradecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}propanoic acid
CAS Registry NumberNot 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 KeyDPYXPLKOAXFWHZ-BKTZGLHTSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phosphatidylserines. These are glycerophosphoserines in which two fatty acids are bonded to the glycerol moiety through ester linkages. As is the case with diacylglycerols, phosphatidylserines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoserines
Direct ParentPhosphatidylserines
Alternative Parents
Substituents
  • Diacyl-glycerol-3-phosphoserine
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Tricarboxylic acid or derivatives
  • Phosphoethanolamine
  • Fatty acid ester
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Amino acid
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Carboxylic acid
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Carbonyl group
  • Organic oxide
  • Primary amine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.93ALOGPS
logP8.24ChemAxon
logS-6.7ALOGPS
pKa (Strongest Acidic)1.47ChemAxon
pKa (Strongest Basic)9.38ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area171.68 ŲChemAxon
Rotatable Bond Count37ChemAxon
Refractivity188.75 m³·mol⁻¹ChemAxon
Polarizability82.09 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9040202100-9d0469f0ec413d4762a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-9120000000-453102454741e6cf2102View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-9350011000-3247a3c8a026d15482bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zi0-1190202100-ac304e93885c688c2ae7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-4390100000-35266c4865ec80de4ad7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9131000000-e5023002f4137d23ad90View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000010900-1ae600a29aeceb18a066View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-0011691600-8135129bea24056bf94aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0011691100-212baaca50426ef128fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03vi-0000099900-e1513e0ec49b8deeafdbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03vo-0900099900-07b9b258ed17c82d83f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03vo-0900099900-07b9b258ed17c82d83f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0000016900-5f25b0a75d700f1a0804View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000002900-07dbe82b5cfe9c8fe044View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0090033100-d1b3ee83ea20f80401cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000000900-52a8ce6dd0ada1a2b013View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0000001900-b4a50970d5a6bbcef93eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uxr-0179105300-86a6b6c3657a596b4515View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Brain
  • Heart
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
HeartExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0012333
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028952
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52926036
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Phosphatidylserine decarboxylase proenzyme, mitochondrial
General function:
Not Available
Specific function:
Catalyzes the formation of phosphatidylethanolamine (PtdEtn) from phosphatidylserine (PtdSer). Plays a central role in phospholipid metabolism and in the interorganelle trafficking of phosphatidylserine.
Gene Name:
PISD
Uniprot ID:
Q58DH2
Molecular weight:
47244.0
Reactions
PS(14:0/16:1(9Z)) → PE(14:0/16:1(9Z)) + Carbon dioxidedetails
Enzyme Details
2. Phosphatidylserine synthase 1
General function:
Not Available
Specific function:
Catalyzes a base-exchange reaction in which the polar head group of phosphatidylethanolamine (PE) or phosphatidylcholine (PC) is replaced by L-serine. In membranes, PTDSS1 catalyzes mainly the conversion of phosphatidylcholine. Also converts, in vitro and to a lesser extent, phosphatidylethanolamine (By similarity).
Gene Name:
PTDSS1
Uniprot ID:
Q2KHY9
Molecular weight:
55416.0
Reactions
PC(14:0/16:1(9Z)) + L-Serine → Choline + PS(14:0/16:1(9Z))details