Cannabis Compound Database: Showing Compound Card for PS(18:1(11Z)/18:1(11Z)) (CDB003096)

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Record Information

Version

1.0

Created at

2020-03-30 20:21:39 UTC

Updated at

2020-12-07 19:10:24 UTC

CannabisDB ID

CDB003096

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

PS(18:1(11Z)/18:1(11Z))

Description

PS(18:1(11Z)/18:1(11Z)) 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(18:1(11Z)/18:1(11Z)), in particular, consists of two 11Z-octadecenoyl 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-divaccenoyl-rac-glycero-3-phosphoserine	Lipid Annotator, HMDB
PS(18:1/18:1)	Lipid Annotator, HMDB
Phosphatidylserine(18:1/18:1)	Lipid Annotator, HMDB
Phosphatidylserine(36:2)	Lipid Annotator, HMDB
PSer(36:2)	Lipid Annotator, HMDB
PSer(18:1/18:1)	Lipid Annotator, HMDB
PS(36:2)	Lipid Annotator, HMDB
1,2-di(11Z-octadecenoyl)-rac-glycero-3-phosphoserine	Lipid Annotator, HMDB
PS(18:1(11Z)/18:1(11Z))	Lipid Annotator

Chemical Formula

C₄₂H₇₈NO₁₀P

Average Molecular Weight

788.06

Monoisotopic Molecular Weight

787.5363

IUPAC Name

(2S)-2-amino-3-({[(2R)-2,3-bis[(11Z)-octadec-11-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)propanoic acid

Traditional Name

(2S)-2-amino-3-{[(2R)-2,3-bis[(11Z)-octadec-11-enoyloxy]propoxy(hydroxy)phosphoryl]oxy}propanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCC\C=C/CCCCCC)C(O)=O

InChI Identifier

InChI=1S/C42H78NO10P/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/h13-16,38-39H,3-12,17-37,43H2,1-2H3,(H,46,47)(H,48,49)/b15-13-,16-14-/t38-,39+/m1/s1

InChI Key

CZIBEPMLQVZXGD-DGQMPYMMSA-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

Not Available

Ontology

Physiological effect

Organoleptic effect:

Touch:

Smooth

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Biofluid and excreta:

Blood

Subcellular:

Role

Biological role:

Industrial application:

Food and nutrition:

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	4.94	ALOGPS
logP	10.55	ChemAxon
logS	-7	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	42	ChemAxon
Refractivity	217.47 m³·mol⁻¹	ChemAxon
Polarizability	93.12 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(18:1(11Z)/18:1(11Z)), TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	PS(18:1(11Z)/18:1(11Z)), TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	PS(18:1(11Z)/18:1(11Z)), TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000l-9020121400-fa6cdb33e52882b9f4d2	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000f-9010000000-51340e82b3c4dab1475e	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000l-9033000100-c322bfa92b92654667dc	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01q9-1190032300-21bfa40e320406c65148	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-003r-5290110100-06566479f56eb90e951a	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9120100000-eb85b94f8251f2d1fffb	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03k9-0000001690-430793a1f49553bdd03e	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0000000290-2af557577adf8dd4d0b1	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0090003310-ad089ba119dae26a0d13	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0000000900-a24428b88fc31234d1d0	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0000001900-9c4fec99b40594066f80	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00lb-0160709600-b05590e70399ca8926ef	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000001900-5dedc46c40b917f10744	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udr-0001029500-58e50a27902d1ad5c54a	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-0001029100-e87998bd7db3c7d928fd	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-14i6-0000004900-ef7e44d1be3adfa5a09d	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0k96-0400004900-31bf8f1446ce1d1b222f	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0k96-0400004900-31bf8f1446ce1d1b222f	2021-09-25	View Spectrum

NMR

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:1(11Z))		Not Available
Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:1(11Z))		Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0112272

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

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

METLIN ID

Not Available

PubChem Compound

131819696

PDB ID

Not Available

ChEBI ID

Not Available

References

General References

Not Available

Showing Compound Card for PS(18:1(11Z)/18:1(11Z)) (CDB003096)

Structure for CDB003096 (PS(18:1(11Z)/18:1(11Z)))