Cannabis Compound Database: Showing Compound Card for PS(18:0/18:0) (CDB001216)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (26)transporters (1) Show 47 proteins XML

Record Information

Version

1.0

Created at

2020-03-30 18:11:31 UTC

Updated at

2020-12-07 19:08:01 UTC

CannabisDB ID

CDB001216

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

PS(18:0/18:0)

Description

PS(18:0/18:0) 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 positions. PS(18:0/18:0), in particular, consists of two octadecanoyl chains at positions C-1 and C-2. 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,2-Dioctadecanoyl-sn-glycero-3-phosphoserine	ChEBI
Distearoyl phosphatidylserine	ChEBI
Phosphatidylserine(18:0/18:0)	ChEBI
Phosphatidylserine(36:0)	ChEBI
pSer(18:0/18:0)	ChEBI
pSer(36:0)	ChEBI
1,2-Distearoyl-rac-glycero-3-phosphoserine	HMDB
PS(36:0)	HMDB
1,2-Dioctadecanoyl-rac-glycero-3-phosphoserine	HMDB
PS(18:0/18:0)	Lipid Annotator

Chemical Formula

C₄₂H₈₂NO₁₀P

Average Molecular Weight

792.09

Monoisotopic Molecular Weight

791.5676

IUPAC Name

(2S)-2-amino-3-({[(2R)-2,3-bis(octadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acid

Traditional Name

distearoyl phosphatidylserine

CAS Registry Number

Not Available

SMILES

[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCC)C(O)=O

InChI Identifier

InChI=1S/C42H82NO10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-40(44)50-35-38(36-51-54(48,49)52-37-39(43)42(46)47)53-41(45)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h38-39H,3-37,43H2,1-2H3,(H,46,47)(H,48,49)/t38-,39+/m1/s1

InChI Key

TZCPCKNHXULUIY-RGULYWFUSA-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoserines

Direct Parent

Phosphatidylserines

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 Framework

Aliphatic acyclic compounds

External Descriptors

3-sn-phosphatidyl-L-serine (CHEBI:84519 )
Diacylglycerophosphoserines (LMGP03010036 )

Ontology

Physiological effect

Organoleptic effect:

Touch:

Smooth

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Tissue and substructures:

All tissues

Organ and components:

Biofluid and excreta:

Blood

Cell and elements:

Extracellular

Subcellular:

Role

Industrial application:

Food and nutrition:

Biological role:

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
logP	4.95	ALOGPS
logP	11.27	ChemAxon
logS	-7.1	ALOGPS
pKa (Strongest Acidic)	1.47	ChemAxon
pKa (Strongest Basic)	9.38	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	171.68 Å²	ChemAxon
Rotatable Bond Count	44	ChemAxon
Refractivity	215.24 m³·mol⁻¹	ChemAxon
Polarizability	96.15 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	PS(18:0/18:0), TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	PS(18:0/18:0), TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	PS(18:0/18:0), TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Orbitrap 37V, negative	splash10-00di-0000000900-22591428bb6273131cdc	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 42V, negative	splash10-00di-0010000900-ba4725252c743910fc6b	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 49V, negative	splash10-00di-0030000900-cf3c4f9f64b537902839	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 53V, negative	splash10-0089-0090000600-48210c75c026547a63af	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 64V, negative	splash10-001i-0090000100-ec3346405e185878d998	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 82V, negative	splash10-001i-0090000000-89495dcfc466d296908e	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 98V, negative	splash10-001i-0090000000-4568190f9e65c021c183	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 120V, negative	splash10-001i-1190000000-3fa25288c531b8c8546b	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 142V, negative	splash10-003r-4290000000-ce23c4801ecc40c857d6	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 175V, negative	splash10-004i-9110000000-81aea2b780940befed87	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 55V, negative	splash10-001i-0090210000-9f1730651a0fbc8977bf	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 55V, negative	splash10-001i-0090000000-1dfdc3824df469b8ca7e	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 55V, negative	splash10-001i-0090000000-9c09632abef0d1b601bc	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 55V, negative	splash10-004j-9000000000-4db762aff12b7cd28a70	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 55V, negative	splash10-001i-0090000000-6da632a0f6c80497dbf9	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 36V, negative	splash10-0006-0000000900-ad43347e0c2b9f181d11	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 49V, negative	splash10-0f6x-0000200900-955d6c499624cfead776	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 61V, negative	splash10-0gb9-0020900300-6912159483890a11c7f2	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 80V, negative	splash10-001i-1290300000-491b8e236ede430a15e7	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000l-9020120400-fcdc30f10d82fdda5f30	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000l-9010000000-798fe1f94003146dddcc	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000f-9033012100-5441754e2cc7cc4f3a80	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00si-1190130500-5b1e74195d04be9bdfc4	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-003r-5390110100-565b2aaae023469aafb8	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9120100000-a4c21235308cfbf9bd0b	2015-09-15	View Spectrum

NMR

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
Phosphatidylcholine Biosynthesis PC(18:0/18:0)		Not Available
Phosphatidylethanolamine Biosynthesis PE(18:0/18:0)		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Group 10 secretory phospholipase A2	PLA2G10	16p13.1-p12	O15496	details
Diacylglycerol kinase gamma	DGKG	3q27.2-q27.3	P49619	details
Diacylglycerol kinase alpha	DGKA	12q13.3	P23743	details
Diacylglycerol kinase delta	DGKD	2q37.1	Q16760	details
Diacylglycerol kinase beta	DGKB	7p21.2	Q9Y6T7	details
Protein kinase C alpha type	PRKCA	17q22-q23.2	P17252	details
Probable phospholipid-transporting ATPase IA	ATP8A1	4p13	Q9Y2Q0	details
Phospholipid scramblase 1	PLSCR1	3q23	O15162	details
Phosphatidylserine synthase 1	PTDSS1	8q22	P48651	details
Scavenger receptor class B member 1	SCARB1	12q24.31	Q8WTV0	details
Phosphatidylserine decarboxylase proenzyme	PISD	22q12.2	Q9UG56	details
Bifunctional arginine demethylase and lysyl-hydroxylase JMJD6	JMJD6	17q25	Q6NYC1	details
Phosphatidylserine synthase 2	PTDSS2	11p15.5	Q9BVG9	details
2-acylglycerol O-acyltransferase 2	MOGAT2	11q13.5	Q3SYC2	details
Phosphatidylinositol-4-phosphate 3-kinase C2 domain-containing subunit alpha	PIK3C2A	11p15.5-p14	O00443	details
Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 2	INPPL1	11q13	O15357	details
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase delta-3	PLCD3	17q21.31	Q8N3E9	details
Sphingomyelin phosphodiesterase 3	SMPD3	16q22.1	Q9NY59	details
Phospholipid scramblase 2	PLSCR2	3q24	Q9NRY7	details
Phospholipid scramblase 3	PLSCR3	17p13.1	Q9NRY6	details
Phospholipid scramblase 4	PLSCR4	3q24	Q9NRQ2	details
Phospholipid scramblase family member 5	PLSCR5	3q24	A0PG75	details
Phospholipase A1 member A	PLA1A	3q13.13-q13.2	Q53H76	details
Sphingomyelin phosphodiesterase 4	SMPD4	2q21.1	Q9NXE4	details
Protein kinase C delta-binding protein	PRKCDBP	11p15.4	Q969G5	details
Lactadherin	MFGE8	15q25	Q08431	details

Transporters

Protein Name	Gene Name	Locus	Uniprot ID	Details
Probable phospholipid-transporting ATPase IA	ATP8A1	4p13	Q9Y2Q0	details

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Group 10 secretory phospholipase A2	PLA2G10	16p13.1-p12	O15496	details
Diacylglycerol kinase gamma	DGKG	3q27.2-q27.3	P49619	details
Diacylglycerol kinase alpha	DGKA	12q13.3	P23743	details
Diacylglycerol kinase beta	DGKB	7p21.2	Q9Y6T7	details
Protein kinase C alpha type	PRKCA	17q22-q23.2	P17252	details
Probable phospholipid-transporting ATPase IA	ATP8A1	4p13	Q9Y2Q0	details
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase delta-3	PLCD3	17q21.31	Q8N3E9	details
Sphingomyelin phosphodiesterase 3	SMPD3	16q22.1	Q9NY59	details
Transcriptional regulator ATRX	ATRX	Xq21.1	P46100	details
Sphingomyelin phosphodiesterase 4	SMPD4	2q21.1	Q9NXE4	details
Annexin A9	ANXA9	1q21	O76027	details

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Diacylglycerol kinase gamma	DGKG	3q27.2-q27.3	P49619	details
Diacylglycerol kinase alpha	DGKA	12q13.3	P23743	details
Diacylglycerol kinase delta	DGKD	2q37.1	Q16760	details
Diacylglycerol kinase beta	DGKB	7p21.2	Q9Y6T7	details
Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 2	INPPL1	11q13	O15357	details
Phosphatidylserine receptor transcript variant 2	JMJD6	17q25	B2WTI4	details
Phosphatidylserine receptor transcript variant 1	JMJD6	17q25	B2WTI3	details

Transcriptional Factors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Group 10 secretory phospholipase A2	PLA2G10	16p13.1-p12	O15496	details
Transcriptional regulator ATRX	ATRX	Xq21.1	P46100	details

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0012378

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB028996

KNApSAcK ID

Not Available

Chemspider ID

7826046

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9547096

PDB ID

P5S

ChEBI ID

84519

References

General References

Not Available

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

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Enzymes

Enzyme Details

1. Group 10 secretory phospholipase A2

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

Enzyme Details

2. Diacylglycerol kinase gamma

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

Enzyme Details

3. Diacylglycerol kinase alpha

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

Enzyme Details

4. Diacylglycerol kinase delta

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

Enzyme Details

5. Diacylglycerol kinase beta

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

Enzyme Details

6. Protein kinase C alpha type

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

Enzyme Details

7. Probable phospholipid-transporting ATPase IA

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

Enzyme Details

8. Phospholipid scramblase 1

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

Enzyme Details

9. Phosphatidylserine synthase 1

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

Enzyme Details

10. Scavenger receptor class B member 1

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

Enzyme Details

1. Probable phospholipid-transporting ATPase IA

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.

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Showing Compound Card for PS(18:0/18:0) (CDB001216)

Structure for CDB001216 (PS(18:0/18:0))

Enzymes

Transporters