Cannabis Compound Database: Showing Compound Card for PA(20:0/22:0) (CDB003237)

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Record Information

Version

1.0

Created at

2020-03-30 20:31:03 UTC

Updated at

2020-12-07 19:10:33 UTC

CannabisDB ID

CDB003237

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

PA(20:0/22:0)

Description

PA(20:0/22:0) 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(20:0/22:0), in particular, consists of one eicosanoyl 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-Arachidoyl-2-behenoyl-sn-glycero-3-phosphate	HMDB
1-Arachidoyl-2-behenoyl-sn-phosphatidic acid	HMDB
PA(42:0)	HMDB
Phosphatidic acid(20:0/22:0)	HMDB
Phosphatidic acid(42:0)	HMDB
Phosphatidate(20:0/22:0)	HMDB
Phosphatidate(42:0)	HMDB
1-arachidoyl-2-behenoyl-sn-glycero-3-phosphate	SMPDB, HMDB
1-arachidoyl-2-behenoyl-sn-phosphatidic acid	SMPDB, HMDB
PA(42:0)	SMPDB, HMDB
Phosphatidic acid(20:0/22:0)	SMPDB, HMDB
Phosphatidic acid(42:0)	SMPDB, HMDB
Phosphatidate(20:0/22:0)	SMPDB, HMDB
PA(20:0/22:0)	SMPDB

Chemical Formula

C₄₅H₈₉O₈P

Average Molecular Weight

789.17

Monoisotopic Molecular Weight

788.6295

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C45H89O8P/c1-3-5-7-9-11-13-15-17-19-21-22-24-26-28-30-32-34-36-38-40-45(47)53-43(42-52-54(48,49)50)41-51-44(46)39-37-35-33-31-29-27-25-23-20-18-16-14-12-10-8-6-4-2/h43H,3-42H2,1-2H3,(H2,48,49,50)/t43-/m1/s1

InChI Key

URIYDEYHGMHXGX-VZUYHUTRSA-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 (LMGP10010948 )

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	9.99	ALOGPS
logP	16.33	ChemAxon
logS	-7.3	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	46	ChemAxon
Refractivity	224.58 m³·mol⁻¹	ChemAxon
Polarizability	102.08 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	splash10-0072-1159702700-fbbd0685882f30070330	2019-02-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-3298312100-d7e124c5cbd69eedd5b0	2019-02-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fr2-1198024000-7161ef5a34786045512d	2019-02-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01rm-5049400300-00f0ef7866a67914553f	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9023000000-d6818d4d5cf99ccb2ae9	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-8270da3e4735a47cfe15	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000000090-1fd26cc3cb715a1f8f30	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0000000990-d119466c39a91d52745f	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03ka-0000920230-5cbf07435796fd27b004	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0000000900-0024c253d82103cbfa29	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002s-0006900400-a0e74262378b322bc936	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03dr-0009300000-570caf1b5f8f81e26b83	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dr-0000000900-9fbd16277de0e21d40b0	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000l-0000005900-d61561e8b64a7e52d6f4	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002g-0000906200-fe1de7ca8d80847bd7c2	2021-09-24	View Spectrum

NMR

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/20:0)		Not Available
De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/22:0)		Not Available
De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/24:0)		Not Available
De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/14:1(9Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/16:1(9Z))		Not Available