Record Information
Version1.0
Created at2020-03-30 18:04:54 UTC
Updated at2020-12-07 19:07:57 UTC
CannabisDB IDCDB001119
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NamePS(18:0/20:0)
DescriptionPS(18:0/20:0) is a phosphatidylserine. It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. 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 atoms. PS(18:0/20:0), in particular, consists of one octadecanoyl chain to the C-1 atom, and one eicosanoyl to the C-2 atom. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. 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. 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. This compound is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
Synonyms
ValueSource
1-Stearoyl-2-arachidonyl-sn-glycero-3-phosphoserineHMDB
Phosphatidylserine(18:0/20:0)HMDB
Phosphatidylserine(38:0)HMDB
PS(38:0)HMDB
pSer(18:0/20:0)HMDB
pSer(38:0)HMDB
1-Octadecanoyl-2-eicosanoyl-sn-glycero-3-phosphoserineHMDB
PS(18:0/20:0)Lipid Annotator
Chemical FormulaC44H86NO10P
Average Molecular Weight820.14
Monoisotopic Molecular Weight819.5989
IUPAC Name(2S)-2-amino-3-({hydroxy[(2R)-2-(icosanoyloxy)-3-(octadecanoyloxy)propoxy]phosphoryl}oxy)propanoic acid
Traditional Name(2S)-2-amino-3-{[hydroxy((2R)-2-(icosanoyloxy)-3-(octadecanoyloxy)propoxy)phosphoryl]oxy}propanoic acid
CAS Registry NumberNot Available
SMILES
[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCCCC)C(O)=O
InChI Identifier
InChI=1S/C44H86NO10P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-43(47)55-40(38-53-56(50,51)54-39-41(45)44(48)49)37-52-42(46)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h40-41H,3-39,45H2,1-2H3,(H,48,49)(H,50,51)/t40-,41+/m1/s1
InChI KeyNTHGOQRMMGSVMQ-ZFESHMOZSA-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
Physiological effect

Organoleptic effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.22ALOGPS
logP12.16ChemAxon
logS-7.2ALOGPS
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 Count46ChemAxon
Refractivity224.44 m³·mol⁻¹ChemAxon
Polarizability100.37 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSPS(18:0/20:0), TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPS(18:0/20:0), TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPS(18:0/20:0), TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9040010130-5a1028d2a895d203bd5b2015-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-9030000000-2aa5c1006e7e2e52d5df2015-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-9053002000-c972934dffffed77a3252015-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0159-1192030220-7119178f3648992576142015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-4290110000-fb72f87326b7432f3fdf2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9020100000-0ad03c372eb3237ed9372015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000000090-f89c97957d05f5e56e0b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0000000190-07c6bd75a0738376c38c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lr-0033900530-eebb82446fd2c56d60c12021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-0000001690-40db868aba6a9ac805122021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000000290-6f5d4181ac406d4fa26b2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0090003310-d617569cf3fbf2a725642021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000001090-03fe6e7c88c7e53a58ad2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-0003069160-6207462f37f749d0a6372021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0003069110-b6e245e0a51227bed0ff2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002r-0000009990-bc1cdb707a640433abce2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002u-0900009990-9e2b1f7d1af2f3ced8af2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002u-0900009990-9e2b1f7d1af2f3ced8af2021-09-23View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Group 10 secretory phospholipase A2PLA2G1016p13.1-p12O15496 details
Diacylglycerol kinase gammaDGKG3q27.2-q27.3P49619 details
Diacylglycerol kinase alphaDGKA12q13.3P23743 details
Diacylglycerol kinase deltaDGKD2q37.1Q16760 details
Diacylglycerol kinase betaDGKB7p21.2Q9Y6T7 details
Protein kinase C alpha typePRKCA17q22-q23.2P17252 details
Probable phospholipid-transporting ATPase IAATP8A14p13Q9Y2Q0 details
Phospholipid scramblase 1PLSCR13q23O15162 details
Phosphatidylserine synthase 1PTDSS18q22P48651 details
Scavenger receptor class B member 1SCARB112q24.31Q8WTV0 details
Phosphatidylserine decarboxylase proenzymePISD22q12.2Q9UG56 details
Bifunctional arginine demethylase and lysyl-hydroxylase JMJD6JMJD617q25Q6NYC1 details
Phosphatidylserine synthase 2PTDSS211p15.5Q9BVG9 details
2-acylglycerol O-acyltransferase 2MOGAT211q13.5Q3SYC2 details
Phosphatidylinositol-4-phosphate 3-kinase C2 domain-containing subunit alphaPIK3C2A11p15.5-p14O00443 details
Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 2INPPL111q13O15357 details
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase delta-3PLCD317q21.31Q8N3E9 details
Sphingomyelin phosphodiesterase 3SMPD316q22.1Q9NY59 details
Phospholipid scramblase 2PLSCR23q24Q9NRY7 details
Phospholipid scramblase 3PLSCR317p13.1Q9NRY6 details
Phospholipid scramblase 4PLSCR43q24Q9NRQ2 details
Phospholipid scramblase family member 5PLSCR53q24A0PG75 details
Phospholipase A1 member APLA1A3q13.13-q13.2Q53H76 details
Sphingomyelin phosphodiesterase 4SMPD42q21.1Q9NXE4 details
Protein kinase C delta-binding proteinPRKCDBP11p15.4Q969G5 details
LactadherinMFGE815q25Q08431 details
Transporters
Protein NameGene NameLocusUniprot IDDetails
Probable phospholipid-transporting ATPase IAATP8A14p13Q9Y2Q0 details
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Group 10 secretory phospholipase A2PLA2G1016p13.1-p12O15496 details
Diacylglycerol kinase gammaDGKG3q27.2-q27.3P49619 details
Diacylglycerol kinase alphaDGKA12q13.3P23743 details
Diacylglycerol kinase betaDGKB7p21.2Q9Y6T7 details
Protein kinase C alpha typePRKCA17q22-q23.2P17252 details
Probable phospholipid-transporting ATPase IAATP8A14p13Q9Y2Q0 details
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase delta-3PLCD317q21.31Q8N3E9 details
Sphingomyelin phosphodiesterase 3SMPD316q22.1Q9NY59 details
Transcriptional regulator ATRXATRXXq21.1P46100 details
Sphingomyelin phosphodiesterase 4SMPD42q21.1Q9NXE4 details
Annexin A9ANXA91q21O76027 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Diacylglycerol kinase gammaDGKG3q27.2-q27.3P49619 details
Diacylglycerol kinase alphaDGKA12q13.3P23743 details
Diacylglycerol kinase deltaDGKD2q37.1Q16760 details
Diacylglycerol kinase betaDGKB7p21.2Q9Y6T7 details
Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 2INPPL111q13O15357 details
Phosphatidylserine receptor transcript variant 2JMJD617q25B2WTI4 details
Phosphatidylserine receptor transcript variant 1JMJD617q25B2WTI3 details
Transcriptional Factors
Protein NameGene NameLocusUniprot IDDetails
Group 10 secretory phospholipase A2PLA2G1016p13.1-p12O15496 details
Transcriptional regulator ATRXATRXXq21.1P46100 details
Concentrations Data
Not Available
HMDB IDHMDB0010164
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB027347
KNApSAcK IDNot Available
Chemspider ID24768055
KEGG Compound IDC02737
BioCyc IDL-1-PHOSPHATIDYL-SERINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52926069
PDB IDNot Available
ChEBI IDNot Available
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 47 proteins in total.

Enzymes

General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a powerful potency for releasing arachidonic acid from cell membrane phospholipids. Prefers phosphatidylethanolamine and phosphatidylcholine liposomes to those of phosphatidylserine.
Gene Name:
PLA2G10
Uniprot ID:
O15496
Molecular weight:
18153.04
General function:
Involved in diacylglycerol kinase activity
Specific function:
Reverses the normal flow of glycerolipid biosynthesis by phosphorylating diacylglycerol back to phosphatidic acid
Gene Name:
DGKG
Uniprot ID:
P49619
Molecular weight:
89095.3
General function:
Involved in diacylglycerol kinase activity
Specific function:
Upon cell stimulation converts the second messenger diacylglycerol into phosphatidate, initiating the resynthesis of phosphatidylinositols and attenuating protein kinase C activity
Gene Name:
DGKA
Uniprot ID:
P23743
Molecular weight:
82629.5
General function:
Involved in diacylglycerol kinase activity
Specific function:
Isoform 2 may be involved in cell growth and tumorigenesis. Involved in clathrin-dependent endocytosis
Gene Name:
DGKD
Uniprot ID:
Q16760
Molecular weight:
134524.2
General function:
Involved in diacylglycerol kinase activity
Specific function:
Exhibits high phosphorylation activity for long-chain diacylglycerols
Gene Name:
DGKB
Uniprot ID:
Q9Y6T7
Molecular weight:
90594.7
General function:
Involved in protein serine/threonine kinase activity
Specific function:
PKC is activated by diacylglycerol which in turn phosphorylates a range of cellular proteins. PKC also serves as the receptor for phorbol esters, a class of tumor promoters
Gene Name:
PRKCA
Uniprot ID:
P17252
Molecular weight:
76763.5
General function:
Involved in ATP binding
Specific function:
May play a role in the transport of aminophospholipids from the outer to the inner leaflet of various membranes and the maintenance of asymmetric distribution of phospholipids, mainly in secretory vesicles
Gene Name:
ATP8A1
Uniprot ID:
Q9Y2Q0
Molecular weight:
131368.2
General function:
Involved in calcium ion binding
Specific function:
May play a role in the antiviral response of interferon (IFN) by amplifying and enhancing the IFN response through increased expression of select subset of potent antiviral genes. May contribute to cytokine-regulated cell proliferation and differentiation
Gene Name:
PLSCR1
Uniprot ID:
O15162
Molecular weight:
35048.8
General function:
Involved in phosphatidylserine biosynthetic process
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.
Gene Name:
PTDSS1
Uniprot ID:
P48651
Molecular weight:
55527.18
General function:
Involved in cell adhesion
Specific function:
Receptor for different ligands such as phospholipids, cholesterol ester, lipoproteins, phosphatidylserine and apoptotic cells. Probable receptor for HDL, located in particular region of the plasma membrane, called caveolae. Facilitates the flux of free and esterified cholesterol between the cell surface and extracellular donors and acceptors, such as HDL and to a lesser extent, apoB-containing lipoproteins and modified lipoproteins. Probably involved in the phagocytosis of apoptotic cells, via its phosphatidylserine binding activity. Receptor for hepatitis C virus glycoprotein E2. Binding between SCARB1 and E2 was found to be independent of the genotype of the viral isolate. Plays an important role in the uptake of HDL cholesteryl ester
Gene Name:
SCARB1
Uniprot ID:
Q8WTV0
Molecular weight:
60877.4

Transporters

General function:
Involved in ATP binding
Specific function:
May play a role in the transport of aminophospholipids from the outer to the inner leaflet of various membranes and the maintenance of asymmetric distribution of phospholipids, mainly in secretory vesicles
Gene Name:
ATP8A1
Uniprot ID:
Q9Y2Q0
Molecular weight:
131368.2

Only showing the first 10 proteins. There are 47 proteins in total.