ChemFOnt: Showing chemical card for 12(S)-Leukotriene B4 (CFc000002404)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:17 UTC

Chemfont ID

CFc000002404

Molecule Identification

Common Name

12(S)-Leukotriene B4

Definition

12(S)-Leukotriene B4 is an agonist of G-protein-coupled receptors for leukotriene B4 (LTB4), BLT1, and BLT2. 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 omega-oxidation carried out by specific cytochrome P450s (CYP4F) followed by beta-oxidation from the omega-carboxy position and after CoA ester formation (PMID: 7649996 , 17623009 , 2866160 , 15866883 ). 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

Not Available

Chemical Formula

C₂₀H₃₂O₄

Average Molecular Weight

336.4657

Monoisotopic Molecular Weight

336.230059512

IUPAC Name

(5S,12S)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid

Traditional Name

(5S,12S)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid

CAS Registry Number

83709-73-3

SMILES

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

InChI Identifier

InChI=1S/C20H32O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,18-19,21-22H,2-5,12-13,16-17H2,1H3,(H,23,24)/t18-,19+/m0/s1

InChI Key

VNYSSYRCGWBHLG-RBUKOAKNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as leukotrienes. These are eicosanoids containing a hydroxyl group attached to the aliphatic chain of an arachidonic acid. Leukotrienes have four double bonds, three (and only three) of which are conjugated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Leukotrienes

Alternative Parents

Substituents

Leukotriene
Hydroxyeicosatetraenoic acid
Long-chain fatty acid
Hydroxy fatty acid
Fatty acid
Unsaturated fatty acid
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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: HMDB0005089)
Membrane (HMDB: HMDB0005089)

Source

Exogenous

Exogenous (HMDB: HMDB0005089)

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: HMDB0005089)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.015 g/L	ALOGPS
logP	5.46	ALOGPS
logP	4.13	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	4.65	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	102.98 m³·mol⁻¹	ChemAxon
Polarizability	41.4 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

FDB023626

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

3246867

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 12(S)-Leukotriene B4 (CFc000002404)

MOL for CFc000002404 (12(S)-Leukotriene B4)

3D MOL for CFc000002404 (12(S)-Leukotriene B4)

3D SDF for CFc000002404 (12(S)-Leukotriene B4)

3D-SDF for CFc000002404 (12(S)-Leukotriene B4)

PDB for CFc000002404 (12(S)-Leukotriene B4)

3D PDB for CFc000002404 (12(S)-Leukotriene B4)

SMILES for CFc000002404 (12(S)-Leukotriene B4)

INCHI for CFc000002404 (12(S)-Leukotriene B4)

Structure for CFc000002404 (12(S)-Leukotriene B4)

3D Structure for CFc000002404 (12(S)-Leukotriene B4)