Cannabis Compound Database: Showing Compound Card for LPA(22:1(13Z)/0:0) (CDB003361)

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Record Information

Version

1.0

Created at

2020-03-30 20:39:24 UTC

Updated at

2020-12-07 19:10:37 UTC

CannabisDB ID

CDB003361

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

LPA(22:1(13Z)/0:0)

Description

LysoPA(22:1(13Z)/0:0), also known as lpa(22:1) or lpa(22:1(13Z)/0:0), belongs to the class of organic compounds known as 1-acylglycerol-3-phosphates. These are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-1 position. LysoPA(22:1(13Z)/0:0) is an extremely weak basic (essentially neutral) compound (based on its pKa). 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-Erucoyl-glycero-3-phosphate	HMDB
1-Erucoyl-lysophosphatidic acid	HMDB
LPA(22:1)	HMDB
LPA(22:1(13Z))	HMDB
LPA(22:1n9/0:0)	HMDB
LPA(22:1W9/0:0)	HMDB
LPA(22:1n9)	HMDB
LPA(22:1W9)	HMDB
Lysophosphatidic acid(22:1(13Z)/0:0)	HMDB
Lysophosphatidic acid(22:1)	HMDB
Lysophosphatidic acid(22:1(13Z))	HMDB
Lysophosphatidic acid(22:1n9/0:0)	HMDB
Lysophosphatidic acid(22:1W9/0:0)	HMDB
Lysophosphatidic acid(22:1n9)	HMDB
Lysophosphatidic acid(22:1W9)	HMDB
LPA(22:1(13Z)/0:0)	HMDB
LPA(22:1/0:0)	HMDB
Lysophosphatidic acid(22:1/0:0)	HMDB
1-(13Z-Docosenoyl)-glycero-3-phosphate	HMDB
1-(13Z-Docosenoyl)-phosphatidic acid	HMDB
1-erucoyl-glycero-3-phosphate	SMPDB, HMDB
1-erucoyl-lysophosphatidic acid	SMPDB, HMDB
LPA(22:1)	SMPDB, HMDB
LPA(22:1(13Z))	SMPDB, HMDB
LPA(22:1n9/0:0)	SMPDB, HMDB
LPA(22:1w9/0:0)	SMPDB, HMDB
LPA(22:1n9)	SMPDB, HMDB
LPA(22:1w9)	SMPDB, HMDB
Lysophosphatidic acid(22:1(13Z)/0:0)	SMPDB, HMDB
Lysophosphatidic acid(22:1)	SMPDB, HMDB
Lysophosphatidic acid(22:1(13Z))	SMPDB, HMDB
Lysophosphatidic acid(22:1n9/0:0)	SMPDB, HMDB
Lysophosphatidic acid(22:1w9/0:0)	SMPDB, HMDB
Lysophosphatidic acid(22:1n9)	SMPDB, HMDB

Chemical Formula

C₂₅H₄₉O₇P

Average Molecular Weight

492.63

Monoisotopic Molecular Weight

492.3216

IUPAC Name

{3-[(13Z)-docos-13-enoyloxy]-2-hydroxypropoxy}phosphonic acid

Traditional Name

3-[(13Z)-docos-13-enoyloxy]-2-hydroxypropoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCC\C=C/CCCCCCCCCCCC(=O)OCC(O)COP(O)(O)=O

InChI Identifier

InChI=1S/C25H49O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25(27)31-22-24(26)23-32-33(28,29)30/h9-10,24,26H,2-8,11-23H2,1H3,(H2,28,29,30)/b10-9-

InChI Key

UXYLIEZFFBAJAG-KTKRTIGZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-acylglycerol-3-phosphates. These are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-1 position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphates

Direct Parent

1-acylglycerol-3-phosphates

Alternative Parents

Substituents

1-acylglycerol-3-phosphate
Fatty acid ester
Monoalkyl phosphate
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
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	6.36	ALOGPS
logP	7.26	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	1.51	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	25	ChemAxon
Refractivity	133.7 m³·mol⁻¹	ChemAxon
Polarizability	58.45 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	LPA(22:1(13Z)/0:0), 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01vk-9430000000-6dd762485f3b051c515f	Spectrum
Predicted GC-MS	LPA(22:1(13Z)/0:0), non-derivatized, 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	Not Available	2020-06-30	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2020-06-30	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2020-06-30	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2020-06-30	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2020-06-30	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2020-06-30	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0000900000-84ccfe6cab2714cae793	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0000900000-84ccfe6cab2714cae793	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udu-2905600000-b8513af04434a988bb2e	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0000900000-4c1c06ee7eb7a46a79ed	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0000900000-4c1c06ee7eb7a46a79ed	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-0905700000-bcf9678f2804f9abc1fc	2021-09-24	View Spectrum

NMR

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/14:0/22:1(13Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/14:0/24:1(15Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/14:0/18:2(9Z,12Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/14:0/18:3(6Z,9Z,12Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/14:0/20:4(5Z,8Z,11Z,14Z))		Not Available