ChemFOnt: Showing chemical card for CPA(18:1(11Z)/0:0) (CFc000003054)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:48:04 UTC

Chemfont ID

CFc000003054

Molecule Identification

Common Name

CPA(18:1(11Z)/0:0)

Definition

cPA(18:1(11Z)/0:0) is a cyclic phosphatidic acid or cyclic lysophosphatidic acid. It is a glycerophospholipid in which a cyclic phosphate moiety occupies two glycerol substitution sites. Lysophosphatidic acids can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1). Fatty acids containing 16 and 18 carbons are the most common. Cyclic phosphatidic acids have been detected in a wide range of organisms including humans, especially in the brain but also in serum (at a concentration of 10-7M). cPA's have a cyclic phosphate at the sn-2 and sn-3 positions of the glycerol carbons, and this structure is absolutely necessary for their activities. In particular, it is found in tissues subject to injury, and while it may have some similar signalling functions to lysophosphatidic acid per se, it also has some quite distinct biological activities. For example, cyclic phosphatidic acid is known to be a specific inhibitor of DNA polymerase alpha. It has an appreciable effect on the inhibition of cancer cell invasion and metastasis.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₁H₃₉O₆P

Average Molecular Weight

418.5045

Monoisotopic Molecular Weight

418.248425492

IUPAC Name

(2-hydroxy-2-oxo-1,3,2lambda5-dioxaphospholan-4-yl)methyl octadec-11-enoate

Traditional Name

(2-hydroxy-2-oxo-1,3,2lambda5-dioxaphospholan-4-yl)methyl octadec-11-enoate

CAS Registry Number

None

SMILES

CCCCCCC=CCCCCCCCCCC(=O)OCC1COP(O)(=O)O1

InChI Identifier

InChI=1S/C21H39O6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(22)25-18-20-19-26-28(23,24)27-20/h7-8,20H,2-6,9-19H2,1H3,(H,23,24)

InChI Key

AXUULXHJKNFQON-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-acyl-sn-glycerol-2,3-cyclic-phosphates. These are monoacylglycerophosphates consisting of a sn-glycerol 2,3-cyclic phosphate that carries an acyl group at the 1-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphates

Direct Parent

1-acyl-sn-glycerol-2,3-cyclic-phosphates

Alternative Parents

Substituents

1-acyl-sn-glycerol-2,3-cyclic-phosphate
Fatty acid ester
Organic phosphoric acid derivative
Fatty acyl
1,3_dioxaphospholane
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organooxygen compound
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

All Tissues (HMDB: HMDB0007005)

Cellular substructure

Membrane (HMDB: HMDB0007005)
Extracellular (HMDB: HMDB0007005)

Source

Exogenous

Exogenous (HMDB: HMDB0007005)

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: HMDB0007005)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0022 g/L	ALOGPS
logP	5.66	ALOGPS
logP	6.38	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	1.84	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.06 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	111.52 m³·mol⁻¹	ChemAxon
Polarizability	48.6 Å³	ChemAxon
Number of Rings	1	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

FDB024199

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

76040435

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for CPA(18:1(11Z)/0:0) (CFc000003054)

MOL for CFc000003054 (CPA(18:1(11Z)/0:0))

3D MOL for CFc000003054 (CPA(18:1(11Z)/0:0))

3D SDF for CFc000003054 (CPA(18:1(11Z)/0:0))

3D-SDF for CFc000003054 (CPA(18:1(11Z)/0:0))

PDB for CFc000003054 (CPA(18:1(11Z)/0:0))

3D PDB for CFc000003054 (CPA(18:1(11Z)/0:0))

SMILES for CFc000003054 (CPA(18:1(11Z)/0:0))

INCHI for CFc000003054 (CPA(18:1(11Z)/0:0))

Structure for CFc000003054 (CPA(18:1(11Z)/0:0))

3D Structure for CFc000003054 (CPA(18:1(11Z)/0:0))