Cannabis Compound Database: Showing Compound Card for PA(18:0/22:0) (CDB003056)

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Record Information

Version

1.0

Created at

2020-03-30 20:18:58 UTC

Updated at

2020-12-07 19:10:21 UTC

CannabisDB ID

CDB003056

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

PA(18:0/22:0)

Description

PA(18:0/22:0) is a phosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PA(18:0/22:0), in particular, consists of one octadecanoyl chain to the C-1 atom, and one docosanoyl to the C-2 atom. The oleic acid moiety is derived from vegetable oils, especially olive and canola oil, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids. 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-Stearoyl-2-behenoyl-sn-glycero-3-phosphate	HMDB
1-Stearoyl-2-behenoyl-sn-phosphatidic acid	HMDB
PA(40:0)	HMDB
Phosphatidic acid(18:0/22:0)	HMDB
Phosphatidic acid(40:0)	HMDB
Phosphatidate(18:0/22:0)	HMDB
Phosphatidate(40:0)	HMDB
1-stearoyl-2-behenoyl-sn-glycero-3-phosphate	SMPDB, HMDB
1-stearoyl-2-behenoyl-sn-phosphatidic acid	SMPDB, HMDB
PA(40:0)	SMPDB, HMDB
Phosphatidic acid(18:0/22:0)	SMPDB, HMDB
Phosphatidic acid(40:0)	SMPDB, HMDB
Phosphatidate(18:0/22:0)	SMPDB, HMDB
PA(18:0/22:0)	SMPDB

Chemical Formula

C₄₃H₈₅O₈P

Average Molecular Weight

761.12

Monoisotopic Molecular Weight

760.5982

IUPAC Name

[(2R)-2-(docosanoyloxy)-3-(octadecanoyloxy)propoxy]phosphonic acid

Traditional Name

(2R)-2-(docosanoyloxy)-3-(octadecanoyloxy)propoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C43H85O8P/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-43(45)51-41(40-50-52(46,47)48)39-49-42(44)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h41H,3-40H2,1-2H3,(H2,46,47,48)/t41-/m1/s1

InChI Key

VIZPWEUJMOZTNE-VQJSHJPSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,2-diacylglycerol-3-phosphates. These are glycerol-3-phosphates in which the glycerol moiety is bonded to two aliphatic chains through ester linkages.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphates

Direct Parent

1,2-diacylglycerol-3-phosphates

Alternative Parents

Substituents

1,2-diacylglycerol-3-phosphate
Fatty acid ester
Monoalkyl phosphate
Dicarboxylic acid or derivatives
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Carboxylic acid ester
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Diacylglycerophosphates (LMGP10010035 )

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	9.84	ALOGPS
logP	15.44	ChemAxon
logS	-7.2	ALOGPS
pKa (Strongest Acidic)	1.32	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	44	ChemAxon
Refractivity	215.38 m³·mol⁻¹	ChemAxon
Polarizability	97.78 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

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-02ml-1179803700-88eb7b8f6f44e6312479	2019-02-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0101-3298312100-52c87b33027ff9d0f344	2019-02-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00vv-1197024000-bd87ab61d3b3b3f10121	2019-02-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-06a0-4093400300-312eb270b980bcea414b	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9050000000-d9b1e9679a50e5e09d61	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-0ab0f0dbd4d7f343ef9c	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01ox-0000000900-db61025fea7f5a1ae0db	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0000005900-3fb6995bc726a5888b8c	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03mi-0000906200-8edd893bf703fddd0b9c	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000000900-b46100095c3d3e7fec21	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bc9-0033900400-f73eef6ce2de5690178e	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001r-1196600100-215b813c343c48de26fb	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000000900-4f5e0459a0492f4fda74	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0020-0000009900-cac2493083ddc18c5cf0	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-02av-0000922400-142e6779566676a0f34c	2021-09-25	View Spectrum

NMR

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/18:0)		Not Available
De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/20:0)		Not Available
De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/22:0)		Not Available
De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/24:0)		Not Available
De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/14:1(9Z))		Not Available