ChemFOnt: Showing chemical card for LysoPA(O-18:0/0:0) (CFc000006778)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:52:52 UTC

Chemfont ID

CFc000006778

Molecule Identification

Common Name

LysoPA(O-18:0/0:0)

Definition

LysoPA(O-18:0/0:0) 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(O-18:0/0:0), in particular, consists of one octadecyl 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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Octadecyl-sn-glycero-3-phosphate	HMDB
LysoPA(18:0E)	HMDB
LysoPA(O-18:0)	HMDB
PA(O-18:0/0:0)	HMDB
[(2R)-2-Hydroxy-3-octadecoxy-propyl] dihydrogen phosphate	HMDB

Chemical Formula

C₂₁H₄₅O₆P

Average Molecular Weight

424.5522

Monoisotopic Molecular Weight

424.295375684

IUPAC Name

[(2R)-2-hydroxy-3-(octadecyloxy)propoxy]phosphonic acid

Traditional Name

(2R)-2-hydroxy-3-(octadecyloxy)propoxyphosphonic acid

CAS Registry Number

None

SMILES

[H][C@@](O)(COCCCCCCCCCCCCCCCCCC)COP(O)(O)=O

InChI Identifier

InChI=1S/C21H45O6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-26-19-21(22)20-27-28(23,24)25/h21-22H,2-20H2,1H3,(H2,23,24,25)/t21-/m1/s1

InChI Key

HUUYDUFSUADEJQ-OAQYLSRUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphocholines

Direct Parent

Phosphatidylcholines

Alternative Parents

Substituents

Diacylglycero-3-phosphocholine
Phosphocholine
Dialkyl phosphate
Fatty acid ester
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Dicarboxylic acid or derivatives
Tetraalkylammonium salt
Quaternary ammonium salt
Carboxylic acid ester
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Feces (PMID: 26848182)

Cellular substructure

Extracellular (HMDB: HMDB0011144)
Membrane (HMDB: HMDB0011144)

Source

Exogenous

Exogenous (HMDB: HMDB0011144)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0011144)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Plasmalogen Synthesis (PathBank: SMP0087517)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0024 g/L	ALOGPS
logP	5.43	ALOGPS
logP	6.23	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	96.22 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	114.43 m³·mol⁻¹	ChemAxon
Polarizability	51.55 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB025672

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for LysoPA(O-18:0/0:0) (CFc000006778)

MOL for CFc000006778 (LysoPA(O-18:0/0:0))

3D MOL for CFc000006778 (LysoPA(O-18:0/0:0))

3D SDF for CFc000006778 (LysoPA(O-18:0/0:0))

3D-SDF for CFc000006778 (LysoPA(O-18:0/0:0))

PDB for CFc000006778 (LysoPA(O-18:0/0:0))

3D PDB for CFc000006778 (LysoPA(O-18:0/0:0))

SMILES for CFc000006778 (LysoPA(O-18:0/0:0))

INCHI for CFc000006778 (LysoPA(O-18:0/0:0))

Structure for CFc000006778 (LysoPA(O-18:0/0:0))

3D Structure for CFc000006778 (LysoPA(O-18:0/0:0))