ChemFOnt: Showing chemical card for Levuglandin D2 (CFc000001621)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:17 UTC

Chemfont ID

CFc000001621

Molecule Identification

Common Name

Levuglandin D2

Definition

Levuglandin D2 is one of the products of a non-enzymatically rearrangement of prostaglandin H2 (PGH2) to this highly reactive gamma-keto aldehyde. PGH2 markedly accelerates the formation of dimers and higher oligomers of amyloid beta1-42. This evidence implicates cyclooxygenase activity in the pathogenesis of Alzheimer's disease, and is associated with the formation of levuglandin adducts of the peptide. Levuglandins (LGs) and their stereo and structural isomers are extraordinarily reactive γ-ketoaldehydes that are generated by rearrangements of prostanoid endoperoxide intermediates of polyene cyclooxygenation. Their rapid adduction with biological nucleophiles results, inter alia, in pathological modifications of proteins and DNA. It also complicates their detection. Cyclooxygenase-promoted lipid oxidation is a pivotal step in the biosynthesis of an array of physiologically active metabolites. COX fosters a highly regio and stereoselective cyclooxygenation of arachidonic acid (AA) to deliver a single, enantiomerically pure endoperoxide, PGH2, that is a branch point in the biosynthesis of numerous hormone-like mediators of cellular activities. Spontaneous rearrangements of PGH2 were known to generate prostaglandins (PG) PGD2 and PGE2. (PMID: 12358806 , 15752459 , 3317517 , 10224068 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₀H₃₂O₅

Average Molecular Weight

352.4651

Monoisotopic Molecular Weight

352.224974134

IUPAC Name

(8R,9R,12S)-9-acetyl-8-formyl-12-hydroxyheptadeca-5,10-dienoic acid

Traditional Name

(8R,9R,12S)-9-acetyl-8-formyl-12-hydroxyheptadeca-5,10-dienoic acid

CAS Registry Number

None

SMILES

[H][C@](O)(CCCCC)C=C[C@@]([H])(C(C)=O)[C@@]([H])(CC=CCCCC(O)=O)C=O

InChI Identifier

InChI=1S/C20H32O5/c1-3-4-7-11-18(23)13-14-19(16(2)22)17(15-21)10-8-5-6-9-12-20(24)25/h5,8,13-15,17-19,23H,3-4,6-7,9-12H2,1-2H3,(H,24,25)/t17-,18-,19-/m0/s1

InChI Key

MLLWPVVMXGUOHD-FHWLQOOXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Hydroxy fatty acid
Branched fatty acid
Unsaturated fatty acid
Secondary alcohol
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0002400)
Membrane (HMDB: HMDB0002400)

Source

Exogenous

Exogenous (HMDB: HMDB0002400)

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: HMDB0002400)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.024 g/L	ALOGPS
logP	3.52	ALOGPS
logP	3.36	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	4.51	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.67 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	100.54 m³·mol⁻¹	ChemAxon
Polarizability	40.55 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022996

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Levuglandin

METLIN ID

Not Available

PubChem Compound

656748

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Levuglandin D2 (CFc000001621)

MOL for CFc000001621 (Levuglandin D2)

3D MOL for CFc000001621 (Levuglandin D2)

3D SDF for CFc000001621 (Levuglandin D2)

3D-SDF for CFc000001621 (Levuglandin D2)

PDB for CFc000001621 (Levuglandin D2)

3D PDB for CFc000001621 (Levuglandin D2)

SMILES for CFc000001621 (Levuglandin D2)

INCHI for CFc000001621 (Levuglandin D2)

Structure for CFc000001621 (Levuglandin D2)

3D Structure for CFc000001621 (Levuglandin D2)