Record Information
Version1.0
Created at2020-04-17 18:57:56 UTC
Updated at2022-12-13 23:36:29 UTC
CannabisDB IDCDB004990
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameLysoPC(16:0/0:0)
DescriptionLysoPC(16:0/0:0) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. LysoPC(16:0/0:0), in particular, consists of one hexadecanoyl chain. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) position. Fatty acids containing 16, 18 and 20 carbons are the most common. LysoPC(20:3(5Z,8Z,11Z)), in particular, consists of one chain of mead acid at the C-1 position. The mead acid moiety is derived from fish oils, liver and kidney. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2, as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling. LysoPC(16:0/0:0) is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
Synonyms
ValueSource
(2R)-2-Hydroxy-3-(hexadecanoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphateChEBI
1-16:0-LysoPCChEBI
1-16:0-LysophosphatidylcholineChEBI
1-Hexadecanoyl-2-lysophosphatidylcholineChEBI
1-Palmitoyl-2-hydroxy-sn-glycero-3-phosphocholineChEBI
1-Palmitoyl-2-lysophosphatidylcholineChEBI
1-Palmitoyl-GPCChEBI
1-Palmitoyl-GPC (16:0)ChEBI
1-Palmitoyl-phosphatidylcholineChEBI
1-Palmitoyl-sn-glycero-3-phosphocholineChEBI
1-PalmitoylphosphatidylcholineChEBI
16:0 LYSO-PCChEBI
GPC(16:0)ChEBI
GPC(16:0/0:0)ChEBI
GPCho 16:0/0:0ChEBI
GPCho(16:0/0:0)ChEBI
LPC 16:0/0:0ChEBI
LPC(16:0)ChEBI
LPC(16:0/0:0)ChEBI
LyPC(16:0)ChEBI
LyPC(16:0/0:0)ChEBI
LysoPC 16:0/0:0ChEBI
LysoPC(16:0)ChEBI
Lysophosphatidylcholine(16:0)ChEBI
Lysophosphatidylcholine(16:0/0:0)ChEBI
PC(16:0/0:0)ChEBI
(2R)-2-Hydroxy-3-(hexadecanoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphoric acidGenerator
1-Palmitoyl-glycero-3-phosphocholineHMDB
1-Palmitoyl-lysophosphatidylcholineHMDB
LysoPC a C16:0HMDB
1-Pam-2-lysoptdchoHMDB
1-Hexadecanoyl-glycero-3-phosphocholineHMDB
1-Palmitoyl-sn-glycerol-3-phosphorylcholineHMDB
1-Palmitoylglycerol-3-phosphorylcholineHMDB
Hydroxide inner salt(S)-isomer OF we 201HMDB
1-O-Hexadecylpropanediol 3-phosphorylcholineHMDB
1-PalmitoyllysophosphatidylcholineHMDB
LYSO-PCHMDB
Hydroxide inner salt(R)-isomer OF we 201HMDB
Hydroxide inner salt(+-)-isomer OF we 201HMDB
Palmitoyl lysophosphatidylcholineHMDB
1-HexadecanoylglycerophosphocholineHMDB
1-PalmitoylglycerophosphocholineHMDB
1-Hexadecanoyl-sn-glycero-3-phosphocholineHMDB
1-Hexadecanoyl-sn-glycerol-3-phosphorylcholineHMDB
1-HexadecanoyllysolecithinHMDB
1-Hexadecyl-sn-glycero-3-phosphocholineHMDB
1-O-Palmitoyl-2-lyso-sn-glycero-3-phosphocholineHMDB
1-O-Palmitoyl-sn-glycero-3-phosphocholineHMDB
1-O-Palmitoyl-sn-glyceryl-3-phosphorylcholineHMDB
1-Palmitoyl-2-lyso-sn-glycero-3-phosphocholineHMDB
1-Palmitoyl-L-alpha-lysophosphatidylcholineHMDB
1-Palmitoyl-L-α-lysophosphatidylcholineHMDB
1-Palmitoyl-sn-glycero-3-phosphorylcholineHMDB
1-Palmitoyl-sn-glycerol-3-phosphatidylcholineHMDB
1-Palmitoyl-sn-glycerol-3-phosphocholineHMDB
1-PalmitoyllecithinHMDB
C(16)-LysophosphatidylcholineHMDB
L-PalmitoyllysolecithinHMDB
L-alpha-LysopalmitoylphosphatidylcholineHMDB
L-alpha-PalmitoyllysophosphatidylcholineHMDB
L-Α-lysopalmitoylphosphatidylcholineHMDB
L-Α-palmitoyllysophosphatidylcholineHMDB
Lysophosphatidylcholine C16:0HMDB
MPPCHMDB
Palmitoyl L-alpha-lysolecithinHMDB
Palmitoyl L-alpha-lysophosphatidylcholineHMDB
Palmitoyl L-lysophosphatidylcholineHMDB
Palmitoyl L-α-lysolecithinHMDB
Palmitoyl L-α-lysophosphatidylcholineHMDB
gamma-Palmitoyl-L-alpha-lysophosphatidylcholineHMDB
Γ-palmitoyl-L-α-lysophosphatidylcholineHMDB
1-Hexadecanoyl-3-glycerophosphorylcholineHMDB
1-Palmitoyl-3-glycerylphosphorylcholineHMDB
1-PalmitoyllysolecithinHMDB
PalmitoyllysolecithinHMDB
Palmitoyllysophosphatidyl cholineHMDB
LysoPC(16:0/0:0)Lipid Annotator, ChEBI
Chemical FormulaC24H50NO7P
Average Molecular Weight495.63
Monoisotopic Molecular Weight495.3325
IUPAC Name(2-{[(2R)-3-(hexadecanoyloxy)-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-3-(hexadecanoyloxy)-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry Number17364-16-8
SMILES
[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C24H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-24(27)30-21-23(26)22-32-33(28,29)31-20-19-25(2,3)4/h23,26H,5-22H2,1-4H3/t23-/m1/s1
InChI KeyASWBNKHCZGQVJV-HSZRJFAPSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphocholine.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct Parent1-acyl-sn-glycero-3-phosphocholines
Alternative Parents
Substituents
  • 1-acyl-sn-glycero-3-phosphocholine
  • Phosphocholine
  • Fatty acid ester
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Alcohol
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic salt
  • Amine
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Organoleptic effect:

Health 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
logP1.83ALOGPS
logP1.19ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area105.12 ŲChemAxon
Rotatable Bond Count24ChemAxon
Refractivity142.27 m³·mol⁻¹ChemAxon
Polarizability58.03 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSLysoPC(16:0/0:0), 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01y9-9311000000-9632c8a0304eb91f3751Spectrum
Predicted GC-MSLysoPC(16:0/0:0), non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSLysoPC(16:0/0:0), non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - n/a 1V, negativesplash10-001i-0010960000-db67de4509c75d7797d52020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-014i-0100190000-466a257c45e674564cc22020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-014i-0300490000-fd86cfc8580fd230b8a82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-1000-1900860000-1a2c5a54bd973898558d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-0zfr-2901600000-7c35aada431d2e8676522020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 40V, positivesplash10-0udi-5901100000-be073d1065c18511ab412020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 1V, positivesplash10-0002-0300900000-849ef7d9847d865ee5422020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 3V, positivesplash10-0002-0000900000-bd89b3b43b9782d3e5d02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-0002-0000900000-7c8338b951da28a32df82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 5V, positivesplash10-0002-0000900000-aa4c98d730731747150c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 7V, positivesplash10-0002-0000900000-2d0497b2b78955e2f3732020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-0002-0100900000-864a738c4e243f3650a82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-0002-0400900000-ce5450f53d5acc84a31e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 17V, positivesplash10-000t-0700900000-4ea431cd2258d012bb042020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-0f8a-0900400000-584dbb5e4958e61bcab82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 23V, positivesplash10-0f89-0900200000-2b522394881a967d30af2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 25V, positivesplash10-0f89-0900100000-64234f354a55048175bc2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 27V, positivesplash10-0f89-0900000000-5f827a15f6679c8604602020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-0f89-1900000000-f09c6fb5cf772c6435042020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 33V, positivesplash10-0f89-1900000000-d5bef12c7df660f031a92020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 35V, positivesplash10-0f89-1900000000-f069c0af6b2eb74b93362020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 40V, positivesplash10-0f89-3900000000-d43ab983a88913d219912020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 45V, positivesplash10-0f8i-5900000000-2b2fa2819f5e2fce5fe42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 13V, positivesplash10-0002-0000900000-0b99348189a68c7f55922020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 18V, positivesplash10-0002-0300900000-4249906ba39f9c0a48ea2020-07-22View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Acyl-protein thioesterase 1LYPLA18q11.23O75608 details
Group XV phospholipase A2PLA2G15Q8NCC3 details
Calcium-dependent phospholipase A2PLA2G51p36-p34P39877 details
Group IIF secretory phospholipase A2PLA2G2F1p35Q9BZM2 details
Cytosolic phospholipase A2PLA2G4A1q25P47712 details
Phospholipase A2PLA2G1B12q23-q24.1P04054 details
Group XIIB secretory phospholipase A2-like proteinPLA2G12BQ9BX93 details
Group 10 secretory phospholipase A2PLA2G1016p13.1-p12O15496 details
Group IIE secretory phospholipase A2PLA2G2E1p36.13Q9NZK7 details
Acyl-protein thioesterase 2LYPLA21p36.11O95372 details
85/88 kDa calcium-independent phospholipase A2PLA2G622q13.1O60733 details
Phosphatidylcholine-sterol acyltransferaseLCAT16q22.1P04180 details
Eosinophil lysophospholipaseCLC19q13.1Q05315 details
Group IID secretory phospholipase A2PLA2G2D1p36.12Q9UNK4 details
Platelet-activating factor acetylhydrolasePLA2G76p21.2-p12Q13093 details
Platelet-activating factor acetylhydrolase IB subunit gammaPAFAH1B319q13.1Q15102 details
Platelet-activating factor acetylhydrolase IB subunit betaPAFAH1B211q23P68402 details
Group 3 secretory phospholipase A2PLA2G322q12.2Q9NZ20 details
Platelet-activating factor acetylhydrolase 2, cytoplasmicPAFAH21p36Q99487 details
Lysophospholipid acyltransferase 5LPCAT312p13Q6P1A2 details
Lysophosphatidylcholine acyltransferase 1LPCAT15p15.33Q8NF37 details
Lysophosphatidylcholine acyltransferase 2LPCAT216q12.2Q7L5N7 details
60 kDa lysophospholipaseASPG14q32.33Q86U10 details
Phospholipase B1, membrane-associatedPLB12p23.2Q6P1J6 details
Cytosolic phospholipase A2 betaPLA2G4B15q11.2-q21.3P0C869 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Calcium-dependent phospholipase A2PLA2G51p36-p34P39877 details
Group IIF secretory phospholipase A2PLA2G2F1p35Q9BZM2 details
Phospholipase A2PLA2G1B12q23-q24.1P04054 details
Group XIIB secretory phospholipase A2-like proteinPLA2G12BQ9BX93 details
Group 10 secretory phospholipase A2PLA2G1016p13.1-p12O15496 details
Group IIE secretory phospholipase A2PLA2G2E1p36.13Q9NZK7 details
Group IID secretory phospholipase A2PLA2G2D1p36.12Q9UNK4 details
Lysophosphatidylcholine acyltransferase 1LPCAT15p15.33Q8NF37 details
Lysophosphatidylcholine acyltransferase 2LPCAT216q12.2Q7L5N7 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Phospholipase A2PLA2G1B12q23-q24.1P04054 details
Transcriptional Factors
Protein NameGene NameLocusUniprot IDDetails
Phospholipase A2PLA2G1B12q23-q24.1P04054 details
Group 10 secretory phospholipase A2PLA2G1016p13.1-p12O15496 details
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.00394 mg/g dry wt
    • David S. Wishart,...
details
GabriolaDetected and Quantified0.00942 mg/g dry wt
    • David S. Wishart,...
details
Island HoneyDetected and Quantified0.00644 mg/g dry wt
    • David S. Wishart,...
details
QuadraDetected and Quantified0.00559 mg/g dry wt
    • David S. Wishart,...
details
Sensi StarDetected and Quantified0.00522 mg/g dry wt
    • David S. Wishart,...
details
Tangerine DreamDetected and Quantified0.00600 mg/g dry wt
    • David S. Wishart,...
details
HMDB IDHMDB0010382
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB027533
KNApSAcK IDNot Available
Chemspider ID405287
KEGG Compound IDC04230
BioCyc IDCPD-8343
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound460602
PDB IDNot Available
ChEBI ID72998
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 37 proteins in total.

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes fatty acids from S-acylated cysteine residues in proteins such as trimeric G alpha proteins or HRAS. Has depalmitoylating activity and also low lysophospholipase activity.
Gene Name:
LYPLA1
Uniprot ID:
O75608
Molecular weight:
24669.355
General function:
Involved in phosphatidylcholine-sterol O-acyltransferase activity
Specific function:
Has transacylase and calcium-independent phospholipase A2 activity. Catalyzes the formation of 1-O-acyl-N-acetylsphingosine and the concomitant release of a lyso-phospholipid (By similarity). May have weak lysophospholipase activity.
Gene Name:
PLA2G15
Uniprot ID:
Q8NCC3
Molecular weight:
Not Available
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. This isozyme hydrolyzes more efficiently L-alpha-1-palmitoyl-2-oleoyl phosphatidylcholine than L-alpha-1-palmitoyl-2-arachidonyl phosphatidylcholine, L-alpha-1-palmitoyl-2-arachidonyl phosphatidylethanolamine, or L-alpha-1-stearoyl-2-arachidonyl phosphatidylinositol. May be involved in the production of lung surfactant, the remodeling or regulation of cardiac muscle.
Gene Name:
PLA2G5
Uniprot ID:
P39877
Molecular weight:
15674.065
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Hydrolyzes phosphatidylglycerol versus phosphatidylcholine with a 15-fold preference.
Gene Name:
PLA2G2F
Uniprot ID:
Q9BZM2
Molecular weight:
23256.29
General function:
Involved in metabolic process
Specific function:
Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response.
Gene Name:
PLA2G4A
Uniprot ID:
P47712
Molecular weight:
85210.19
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides.
Gene Name:
PLA2G1B
Uniprot ID:
P04054
Molecular weight:
16359.535
General function:
Involved in phospholipase A2 activity
Specific function:
Not known; does not seem to have catalytic activity.
Gene Name:
PLA2G12B
Uniprot ID:
Q9BX93
Molecular weight:
Not Available
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 phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a preference for arachidonic-containing phospholipids.
Gene Name:
PLA2G2E
Uniprot ID:
Q9NZK7
Molecular weight:
15988.525
General function:
Involved in hydrolase activity
Specific function:
May hydrolyze fatty acids from S-acylated cysteine residues in proteins such as trimeric G alpha proteins or HRAS. Has lysophospholipase activity (By similarity). Deacylates GAP43.
Gene Name:
LYPLA2
Uniprot ID:
O95372
Molecular weight:
24736.71

Only showing the first 10 proteins. There are 37 proteins in total.