ChemFOnt: Showing chemical card for Leukotriene B4 dimethylamide (CFc000002401)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:16 UTC

Chemfont ID

CFc000002401

Molecule Identification

Common Name

Leukotriene B4 dimethylamide

Definition

Leukotriene B4 dimethylamide is a derivative of Leukotriene B4 (LTB4) and was shown to inhibit neutrophil degranulation induced by LTB4. LTB4 is the major metabolite in neutrophil polymorphonuclear leukocytes. Leukotrienes are metabolites of arachidonic acid derived from the action of 5-LO (5-lipoxygenase). The immediate product of 5-LO is LTA4 (leukotriene A4), which is enzymatically converted into either LTB4 (leukotriene B4) by LTA4 hydrolase or LTC4 (leukotriene C4) by LTC4 synthase. The regulation of leukotriene production occurs at various levels, including expression of 5-LO, translocation of 5-LO to the perinuclear region and phosphorylation to either enhance or inhibit the activity of 5-LO. Biologically active LTB4 is metabolized by w-oxidation carried out by specific cytochrome P450s (CYP4F) followed by beta-oxidation from the w-carboxy position and after CoA ester formation. (PMID: 6288032 , 17623009 )Leukotrienes are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
LTB4dMA	MeSH

Chemical Formula

C₂₂H₃₇NO₃

Average Molecular Weight

363.5341

Monoisotopic Molecular Weight

363.277344055

IUPAC Name

(5S,12R)-5,12-dihydroxy-N,N-dimethylicosa-6,8,10,14-tetraenamide

Traditional Name

(5S,12R)-5,12-dihydroxy-N,N-dimethylicosa-6,8,10,14-tetraenamide

CAS Registry Number

83024-92-4

SMILES

[H][C@](O)(CCCC(=O)N(C)C)C=CC=CC=C[C@]([H])(O)CC=CCCCCC

InChI Identifier

InChI=1S/C22H37NO3/c1-4-5-6-7-8-11-15-20(24)16-12-9-10-13-17-21(25)18-14-19-22(26)23(2)3/h8-13,16-17,20-21,24-25H,4-7,14-15,18-19H2,1-3H3/t20-,21-/m1/s1

InChI Key

BBJRTSLPWQUASB-NHCUHLMSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl amines. N-acyl amines are compounds containing a fatty acid moiety linked to an amine group through an ester linkage.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty amides

Direct Parent

N-acyl amines

Alternative Parents

Substituents

N-acyl-amine
Tertiary carboxylic acid amide
Secondary alcohol
Carboxamide group
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
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: HMDB0005085)
Membrane (HMDB: HMDB0005085)

Source

Exogenous

Exogenous (HMDB: HMDB0005085)

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: HMDB0005085)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.012 g/L	ALOGPS
logP	4.84	ALOGPS
logP	3.77	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	17.72	ChemAxon
pKa (Strongest Basic)	-0.93	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	60.77 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	114.6 m³·mol⁻¹	ChemAxon
Polarizability	46.01 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

FDB023624

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

3246865

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Leukotriene B4 dimethylamide (CFc000002401)

MOL for CFc000002401 (Leukotriene B4 dimethylamide)

3D MOL for CFc000002401 (Leukotriene B4 dimethylamide)

3D SDF for CFc000002401 (Leukotriene B4 dimethylamide)

3D-SDF for CFc000002401 (Leukotriene B4 dimethylamide)

PDB for CFc000002401 (Leukotriene B4 dimethylamide)

3D PDB for CFc000002401 (Leukotriene B4 dimethylamide)

SMILES for CFc000002401 (Leukotriene B4 dimethylamide)

INCHI for CFc000002401 (Leukotriene B4 dimethylamide)

Structure for CFc000002401 (Leukotriene B4 dimethylamide)

3D Structure for CFc000002401 (Leukotriene B4 dimethylamide)