ChemFOnt: Showing chemical card for {2-hydroxy-3-[(11Z)-octadec-11-enoyloxy]propoxy}phosphonic acid (CFc000167282)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 00:01:07 UTC

Chemfont ID

CFc000167282

Molecule Identification

Common Name

{2-hydroxy-3-[(11Z)-octadec-11-enoyloxy]propoxy}phosphonic acid

Definition

LPA(18:1(11Z)/0:0) is an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, lpa(18:1(11Z)/0:0) participates in a number of enzymatic reactions. In particular, lpa(18:1(11Z)/0:0) can be biosynthesized from cis-vaccenoyl-CoA and glycerol 3-phosphate; which is mediated by the enzyme glycerol-3-phosphate acyltransferase. In addition, lpa(18:1(11Z)/0:0) and palmitoleyl-CoA can be converted into PA(18:1(11Z)/16:1(9Z)) through its interaction with the enzyme 1-acyl-sn-glycerol-3-phosphate acyltransferase. In humans, lpa(18:1(11Z)/0:0) is involved in the metabolic disorder called de novo triacylglycerol biosynthesis pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₁H₄₁O₇P

Average Molecular Weight

436.526

Monoisotopic Molecular Weight

436.258990658

IUPAC Name

{2-hydroxy-3-[(11Z)-octadec-11-enoyloxy]propoxy}phosphonic acid

Traditional Name

2-hydroxy-3-[(11Z)-octadec-11-enoyloxy]propoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

CCCCCC\C=C/CCCCCCCCCC(=O)OCC(O)COP(O)(O)=O

InChI Identifier

InChI=1S/C21H41O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)27-18-20(22)19-28-29(24,25)26/h7-8,20,22H,2-6,9-19H2,1H3,(H2,24,25,26)/b8-7-

InChI Key

LWSYATLSXCUNTB-FPLPWBNLSA-N

Chemical Taxonomy

Description

This compound 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
Monoalkyl phosphate
Fatty acid ester
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Secondary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0017 g/L	ALOGPS
logP	4.68	ALOGPS
logP	5.49	ChemAxon
logS	-5.4	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	21	ChemAxon
Refractivity	115.3 m³·mol⁻¹	ChemAxon
Polarizability	49.9 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0187017

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

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

87977831

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for {2-hydroxy-3-[(11Z)-octadec-11-enoyloxy]propoxy}phosphonic acid (CFc000167282)

MOL for CFc000167282 ({2-hydroxy-3-[(11Z)-octadec-11-enoyloxy]propoxy}phosphonic acid)

3D MOL for CFc000167282 ({2-hydroxy-3-[(11Z)-octadec-11-enoyloxy]propoxy}phosphonic acid)

3D SDF for CFc000167282 ({2-hydroxy-3-[(11Z)-octadec-11-enoyloxy]propoxy}phosphonic acid)

3D-SDF for CFc000167282 ({2-hydroxy-3-[(11Z)-octadec-11-enoyloxy]propoxy}phosphonic acid)

PDB for CFc000167282 ({2-hydroxy-3-[(11Z)-octadec-11-enoyloxy]propoxy}phosphonic acid)

3D PDB for CFc000167282 ({2-hydroxy-3-[(11Z)-octadec-11-enoyloxy]propoxy}phosphonic acid)

SMILES for CFc000167282 ({2-hydroxy-3-[(11Z)-octadec-11-enoyloxy]propoxy}phosphonic acid)

INCHI for CFc000167282 ({2-hydroxy-3-[(11Z)-octadec-11-enoyloxy]propoxy}phosphonic acid)

Structure for CFc000167282 ({2-hydroxy-3-[(11Z)-octadec-11-enoyloxy]propoxy}phosphonic acid)

3D Structure for CFc000167282 ({2-hydroxy-3-[(11Z)-octadec-11-enoyloxy]propoxy}phosphonic acid)