Cannabis Compound Database: Showing Compound Card for LysoPA(16:0/0:0) (CDB001259)

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Record Information

Version

1.0

Created at

2020-03-30 18:14:25 UTC

Updated at

2020-12-07 19:08:06 UTC

CannabisDB ID

CDB001259

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

LysoPA(16:0/0:0)

Description

LysoPA(16:0/0:0) is a lysophosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. Lysophosphatidic acids can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) or C-2 (sn-2) position. Fatty acids containing 16 and 18 carbons are the most common.LysoPA(16:0/0:0), in particular, consists of one hexadecanoyl chain. Lysophosphatidic acid is the simplest possible glycerophospholipid. It is the biosynthetic precursor of phosphatidic acid. Although it is present at very low levels only in animal tissues, it is extremely important biologically, influencing many biochemical processes. 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-Hexadecanoyl-sn-glycero-3-phosphate	ChEBI
1-Hexadecanoyl-sn-glycero-3-phosphoric acid	Generator
1-Palmitoylglycerol 3-phosphoric acid	HMDB
1-Palmitoyl-sn-glycerol 3-phosphate	HMDB
PLPA	HMDB
1-Palmitoyl-lysophosphatidic acid	HMDB
1-Palmitoyl-lysophosphatidic acid, (R)-isomer	HMDB
1-Palmitoyl-rac-glycerol 3-phosphate	HMDB
1-Palmitoyl-lysophosphatidic acid, sodium salt, (R)-isomer	HMDB
Lysophosphatidic acid(16:0)	HMDB
1-Palmitoyl-glycero-3-phosphate	HMDB
1-Hexadecanoyl-phosphatidic acid	HMDB
LPA(16:0)	HMDB
LPA(16:0/0:0)	HMDB
1-Hexadecanoyl-glycero-3-phosphate	HMDB
Lysophosphatidic acid(16:0/0:0)	HMDB

Chemical Formula

C₁₉H₃₉O₇P

Average Molecular Weight

410.48

Monoisotopic Molecular Weight

410.2433

IUPAC Name

[3-(hexadecanoyloxy)-2-hydroxypropoxy]phosphonic acid

Traditional Name

PLPA

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCC(=O)OCC(O)COP(O)(O)=O

InChI Identifier

InChI=1S/C19H39O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(21)25-16-18(20)17-26-27(22,23)24/h18,20H,2-17H2,1H3,(H2,22,23,24)

InChI Key

YNDYKPRNFWPPFU-UHFFFAOYSA-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

2-lysophosphatidic acid (CHEBI:64023 )
Monoacylglycerophosphates (C04036 )

Ontology

Physiological effect

Organoleptic effect:

Touch:

Smooth

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Biofluid and excreta:

Blood

Tissue and substructures:

All tissues

Cell and elements:

Extracellular

Subcellular:

Role

Industrial application:

Food and nutrition:

Biological role:

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	3.87	ALOGPS
logP	4.96	ChemAxon
logS	-5.2	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	20	ChemAxon
Refractivity	104.98 m³·mol⁻¹	ChemAxon
Polarizability	47.18 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	LysoPA(16:0/0:0), 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-02n9-5940100000-a5ca92d33fddeb085287	Spectrum
Predicted GC-MS	LysoPA(16:0/0:0), non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - NA , positive	splash10-03di-0549600000-25838221a69792238ab5	2020-07-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-08fr-2986700000-f3b30f5c39843042fd11	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4s-3942000000-0e96d3c410d5f67cbc44	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4s-6930000000-8e619c799b8a218b3a05	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4r-4190300000-bb83e3f01055cbe6102f	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9050000000-de299cedb3cf89da4492	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-f3fc94f808e80bf00353	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000900000-97431642e54a4a707394	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0000900000-97431642e54a4a707394	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pb9-2951500000-d6189b2a977487b10d88	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000900000-61bb60154e9d7308c06d	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0000900000-61bb60154e9d7308c06d	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00du-0955100000-a47b051136d1c4973480	2021-09-24	View Spectrum

NMR

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
Phospholipid Biosynthesis
Glycerolipid Metabolism
Glycerol Kinase Deficiency		Not Available
D-glyceric acidura		Not Available
Familial lipoprotein lipase deficiency		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Phospholipase D2	PLD2	17p13.1	O14939	details
Ectonucleotide pyrophosphatase/phosphodiesterase family member 2	ENPP2	8q24.1	Q13822	details
Diacylglycerol kinase theta	DGKQ	4p16.3	P52824	details
Lipid phosphate phosphohydrolase 2	PPAP2C	19p13	O43688	details
Diacylglycerol kinase alpha	DGKA	12q13.3	P23743	details
Diacylglycerol kinase delta	DGKD	2q37.1	Q16760	details
Lipid phosphate phosphohydrolase 1	PPAP2A	5q11	O14494	details
Diacylglycerol kinase beta	DGKB	7p21.2	Q9Y6T7	details
Diacylglycerol kinase iota	DGKI	7q32.3-q33	O75912	details
Lipid phosphate phosphohydrolase 3	PPAP2B	1p32.2	O14495	details
Diacylglycerol kinase zeta	DGKZ	11p11.2	Q13574	details
Phosphatidate cytidylyltransferase 2	CDS2	20p13	O95674	details
Phosphatidate cytidylyltransferase 1	CDS1	4q21.23	Q92903	details
Acyl-CoA:lysophosphatidylglycerol acyltransferase 1	LPGAT1	1q32	Q92604	details
Focal adhesion kinase 1	PTK2	8q24.3	Q05397	details
Protein-tyrosine kinase 2-beta	PTK2B	8p21.1	Q14289	details
1-acyl-sn-glycerol-3-phosphate acyltransferase gamma	AGPAT3	21q22.3	Q9NRZ7	details
1-acyl-sn-glycerol-3-phosphate acyltransferase beta	AGPAT2	9q34.3	O15120	details
1-acyl-sn-glycerol-3-phosphate acyltransferase alpha	AGPAT1	6p21.3	Q99943	details
Phosphatidylinositol-glycan-specific phospholipase D	GPLD1	6p22.1	P80108	details
Lysophosphatidic acid receptor 2	LPAR2	19p12	Q9HBW0	details
Lysophosphatidic acid receptor 1	LPAR1	9q31.3	Q92633	details
1-acyl-sn-glycerol-3-phosphate acyltransferase epsilon	AGPAT5	8p23.1	Q9NUQ2	details
Glycerol-3-phosphate acyltransferase 4	AGPAT6	8p11.21	Q86UL3	details
Diacylglycerol kinase eta	DGKH	13q14.11	Q86XP1	details
1-acyl-sn-glycerol-3-phosphate acyltransferase delta	AGPAT4	6q26	Q9NRZ5	details
Lysophosphatidylcholine acyltransferase 1	LPCAT1	5p15.33	Q8NF37	details
Lysophosphatidylcholine acyltransferase 2	LPCAT2	16q12.2	Q7L5N7	details
Lysocardiolipin acyltransferase 1	LCLAT1	2p23.1	Q6UWP7	details
Lysophosphatidic acid receptor 3	LPAR3	1p22.3	Q9UBY5	details
Lysophosphatidic acid receptor 5	LPAR5	12p13.31	Q9H1C0	details
Lysophospholipid acyltransferase LPCAT4	LPCAT4	15q14	Q643R3	details
Glycerol-3-phosphate acyltransferase 3	AGPAT9	4q21.23	Q53EU6	details
Lysophosphatidic acid phosphatase type 6	ACP6	1q21	Q9NPH0	details
Lipase member H	LIPH	3q27	Q8WWY8	details
Lipase member I	LIPI	21q11.2	Q6XZB0	details
Lipid phosphate phosphatase-related protein type 4	LPPR4	1p21.2	Q7Z2D5	details
Acylglycerol kinase, mitochondrial	AGK	7q34	Q53H12	details
Phospholipase D1 variant			Q59EA4	details
1-acylglycerol-3-phosphate O-acyltransferase 6 (Lysophosphatidic acid acyltransferase, zeta), isoform CRA_b	AGPAT6	8p11.21	Q2TU73	details
Diacylglycerol kinase, epsilon 64kDa	DGKE	17q22	A1L4Q0	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Ectonucleotide pyrophosphatase/phosphodiesterase family member 2	ENPP2	8q24.1	Q13822	details
Diacylglycerol kinase alpha	DGKA	12q13.3	P23743	details
Diacylglycerol kinase beta	DGKB	7p21.2	Q9Y6T7	details
Lysophosphatidylcholine acyltransferase 1	LPCAT1	5p15.33	Q8NF37	details
Lysophosphatidylcholine acyltransferase 2	LPCAT2	16q12.2	Q7L5N7	details

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Phospholipase D2	PLD2	17p13.1	O14939	details
Ectonucleotide pyrophosphatase/phosphodiesterase family member 2	ENPP2	8q24.1	Q13822	details
Diacylglycerol kinase theta	DGKQ	4p16.3	P52824	details
Diacylglycerol kinase alpha	DGKA	12q13.3	P23743	details
Diacylglycerol kinase delta	DGKD	2q37.1	Q16760	details
Lipid phosphate phosphohydrolase 1	PPAP2A	5q11	O14494	details
Diacylglycerol kinase beta	DGKB	7p21.2	Q9Y6T7	details
Diacylglycerol kinase iota	DGKI	7q32.3-q33	O75912	details
Lipid phosphate phosphohydrolase 3	PPAP2B	1p32.2	O14495	details
Diacylglycerol kinase zeta	DGKZ	11p11.2	Q13574	details
Phosphatidylinositol-glycan-specific phospholipase D	GPLD1	6p22.1	P80108	details
Lysophosphatidic acid receptor 2	LPAR2	19p12	Q9HBW0	details
Lysophosphatidic acid receptor 1	LPAR1	9q31.3	Q92633	details
Diacylglycerol kinase eta	DGKH	13q14.11	Q86XP1	details
Lysophosphatidic acid receptor 3	LPAR3	1p22.3	Q9UBY5	details
Lysophosphatidic acid receptor 4	LPAR4		Q99677	details
Lysophosphatidic acid receptor 5	LPAR5	12p13.31	Q9H1C0	details
Lysophosphatidic acid receptor 6	LPAR6	13q14	P43657	details
Acylglycerol kinase, mitochondrial	AGK	7q34	Q53H12	details
Diacylglycerol kinase, epsilon 64kDa	DGKE	17q22	A1L4Q0	details
High-affinity lysophosphatidic acid receptor homolog			O43898	details
LPAR1 protein	LPAR1	9q31.3	Q6GPG7	details

Transcriptional Factors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Ectonucleotide pyrophosphatase/phosphodiesterase family member 2	ENPP2	8q24.1	Q13822	details
Lipid phosphate phosphohydrolase 3	PPAP2B	1p32.2	O14495	details

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0007853

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB030254

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C04036

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

89566

PDB ID

Not Available

ChEBI ID

64023

References

General References

Not Available

Only showing the first 10 proteins. There are 70 proteins in total.

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Enzymes

Enzyme Details

1. Phospholipase D2

General function:: Involved in protein binding
Specific function:: May have a role in signal-induced cytoskeletal regulation and/or endocytosis (By similarity).
Gene Name:: PLD2
Uniprot ID:: O14939
Molecular weight:: 104656.485

Enzyme Details

2. Ectonucleotide pyrophosphatase/phosphodiesterase family member 2

General function:: Involved in catalytic activity
Specific function:: Hydrolyzes lysophospholipids to produce lysophosphatidic acid (LPA) in extracellular fluids. Major substrate is lysophosphatidylcholine. Also can act on sphingosylphosphphorylcholine producing sphingosine-1-phosphate, a modulator of cell motility. Can hydrolyze, in vitro, bis-pNPP, to some extent pNP-TMP, and barely ATP. Involved in several motility-related processes such as angiogenesis and neurite outgrowth. Acts as an angiogenic factor by stimulating migration of smooth muscle cells and microtubule formation. Stimulates migration of melanoma cells, probably via a pertussis toxin-sensitive G protein. May have a role in induction of parturition. Possible involvement in cell proliferation and adipose tissue development. Tumor cell motility-stimulating factor.
Gene Name:: ENPP2
Uniprot ID:: Q13822
Molecular weight:: 98992.78

Enzyme Details

3. Diacylglycerol kinase theta

General function:: Involved in diacylglycerol kinase activity
Specific function:: Phosphorylates diacylglycerol (DAG) to generate phosphatidic acid (PA). May regulate the activity of protein kinase C by controlling the balance between these two signaling lipids. Activated in the nucleus in response to alpha-thrombin and nerve growth factor. May be involved in cAMP- induced activation of NR5A1 and subsequent steroidogenic gene transcription by delivering PA as ligand for NR5A1. Acts synergistically with NR5A1 on CYP17 transcriptional activity
Gene Name:: DGKQ
Uniprot ID:: P52824
Molecular weight:: 101154.0

Enzyme Details

4. Lipid phosphate phosphohydrolase 2

General function:: Involved in catalytic activity
Specific function:: Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). In addition it hydrolyzes lysophosphatidic acid (LPA), ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is PA > C-1-P > LPA > S-1-P.
Gene Name:: PPAP2C
Uniprot ID:: O43688
Molecular weight:: 32573.435

Enzyme Details

5. Diacylglycerol kinase alpha

General function:: Involved in diacylglycerol kinase activity
Specific function:: Upon cell stimulation converts the second messenger diacylglycerol into phosphatidate, initiating the resynthesis of phosphatidylinositols and attenuating protein kinase C activity
Gene Name:: DGKA
Uniprot ID:: P23743
Molecular weight:: 82629.5

Enzyme Details

6. Diacylglycerol kinase delta

General function:: Involved in diacylglycerol kinase activity
Specific function:: Isoform 2 may be involved in cell growth and tumorigenesis. Involved in clathrin-dependent endocytosis
Gene Name:: DGKD
Uniprot ID:: Q16760
Molecular weight:: 134524.2

Enzyme Details

7. Lipid phosphate phosphohydrolase 1

General function:: Involved in catalytic activity
Specific function:: Broad-specificity phosphohydrolase that dephosphorylates exogenous bioactive glycerolipids and sphingolipids. Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). Pivotal regulator of lysophosphatidic acid (LPA) signaling in the cardiovascular system. Major enzyme responsible of dephosphorylating LPA in platelets, which terminates signaling actions of LPA. May control circulating, and possibly also regulate localized, LPA levels resulting from platelet activation. It has little activity towards ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is LPA > PA > S-1-P > C-1-P. It's down-regulation may contribute to the development of colon adenocarcinoma.
Gene Name:: PPAP2A
Uniprot ID:: O14494
Molecular weight:: 32155.715

Enzyme Details

8. Diacylglycerol kinase beta

General function:: Involved in diacylglycerol kinase activity
Specific function:: Exhibits high phosphorylation activity for long-chain diacylglycerols
Gene Name:: DGKB
Uniprot ID:: Q9Y6T7
Molecular weight:: 90594.7

Enzyme Details

9. Diacylglycerol kinase iota

General function:: Involved in diacylglycerol kinase activity
Specific function:: ATP + 1,2-diacylglycerol = ADP + 1,2-diacyl- sn-glycerol 3-phosphate
Gene Name:: DGKI
Uniprot ID:: O75912
Molecular weight:: 116996.2

Enzyme Details

10. Lipid phosphate phosphohydrolase 3

General function:: Involved in catalytic activity
Specific function:: Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). In addition it hydrolyzes lysophosphatidic acid (LPA), ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is LPA = PA > C-1-P > S-1-P. May be involved in cell adhesion and in cell-cell interactions.
Gene Name:: PPAP2B
Uniprot ID:: O14495
Molecular weight:: 35115.61

Only showing the first 10 proteins. There are 70 proteins in total.

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Showing Compound Card for LysoPA(16:0/0:0) (CDB001259)

Structure for CDB001259 (LysoPA(16:0/0:0))

Enzymes