Cannabis Compound Database: Showing Compound Card for PS(16:0/18:1(11Z)) (CDB002987)

Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References XML

Record Information

Version

1.0

Created at

2020-03-30 20:14:20 UTC

Updated at

2020-12-07 19:10:17 UTC

CannabisDB ID

CDB002987

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

PS(16:0/18:1(11Z))

Description

PS(16:0/18:1(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 atoms. PS(16:0/18:1(11Z)), in particular, consists of one hexadecanoyl chain to the C-1 atom, and one 11Z-octadecenoyl 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
pSer(16:0/18:1)	HMDB
Phosphatidylserine(16:0/18:1)	HMDB
pSer(34:1)	HMDB
Phosphatidylserine(34:1)	HMDB
PS(34:1)	HMDB
PS(16:0/18:1)	HMDB
1-Hexadecanoyl-2-(11Z-octadecenoyl)-sn-glycero-3-phosphoserine	HMDB
1-Palmitoyl-2-vaccenoyl-sn-glycero-3-phosphoserine	HMDB
PS(16:0/18:1(11Z))	Lipid Annotator

Chemical Formula

C₄₀H₇₆NO₁₀P

Average Molecular Weight

762.02

Monoisotopic Molecular Weight

761.5207

IUPAC Name

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

Traditional Name

(2S)-2-amino-3-{[(2R)-3-(hexadecanoyloxy)-2-[(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)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCC\C=C/CCCCCC)C(O)=O

InChI Identifier

InChI=1S/C40H76NO10P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-39(43)51-36(34-49-52(46,47)50-35-37(41)40(44)45)33-48-38(42)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h13,15,36-37H,3-12,14,16-35,41H2,1-2H3,(H,44,45)(H,46,47)/b15-13-/t36-,37+/m1/s1

InChI Key

DHTAMDRFOGPYHA-FXBTWRSESA-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

Diacylglycerophosphoserines (LMGP03010007 )

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	4.63	ALOGPS
logP	10.02	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	41	ChemAxon
Refractivity	207.15 m³·mol⁻¹	ChemAxon
Polarizability	90.62 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(16:0/18:1(11Z)), TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	PS(16:0/18:1(11Z)), TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	PS(16:0/18:1(11Z)), TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	PS(16:0/18:1(11Z)), TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	PS(16:0/18:1(11Z)), TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	PS(16:0/18:1(11Z)), TBDMS_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-9050210300-8dc1c58a9fb50fec8b7d	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000l-9030000000-e0bcdeb9c9a3ad93f0a9	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000l-9061011000-53ae9c8bbe20e3999bbc	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0bu9-1190101200-912e413d6aa8fdee781d	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a7r-4290100000-cd5285140ad4dd45d9cd	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9130100000-f83dc29d044c000df36a	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001j-0000016900-30d709253edd79b40d7b	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0000002900-b825e475a4e4889a3c60	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0090033100-b405dd9335543fb89951	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000000900-fde9f3fdf95a1e6b6ce7	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0000001900-10e4203a46b55668761a	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-07pl-0194606400-6b7535a1743e5c7e88e0	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01ai-0000099900-dd7d21fca711265a33d3	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ao-0900099900-f7c1a9b7f29b762b34da	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ao-0900099900-f7c1a9b7f29b762b34da	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000010900-43a7de9e9dd0d8891e96	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01t9-0002291400-ba9b4276b372eea51a76	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-0002291100-f48670fd618b645dda4b	2021-09-25	View Spectrum