ChemFOnt: Showing chemical card for 12-Oxo-20-trihydroxy-leukotriene B4 (CFc000008030)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:54:39 UTC

Chemfont ID

CFc000008030

Molecule Identification

Common Name

12-Oxo-20-trihydroxy-leukotriene B4

Definition

12-Oxo-20-trihydroxy-leukotriene B4 is the metabolite of lipid omega-oxidation of leukotriene B4 (LTB4). LTB4 is the major metabolite in neutrophil polymorphonuclear leukocytes. Omega-oxidation is the major pathway for the catabolism of leukotriene B4 in human 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 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 , 2853166 , 6088485 ). 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
(5S,20,20,20)-Tetrahydroxy-12-oxo-(6Z,8E,10E,14Z)-eicosatetraenoate	HMDB
(5S,20,20,20)-Tetrahydroxy-12-oxo-(6Z,8E,10E,14Z)-eicosatetraenoic acid	HMDB
12-keto-20,20,20-Trihydroxy-leukotriene b(,4)	HMDB
12-oxo-20,20,20-Trihydroxy-leukotriene b(,4)	HMDB
DOxLTB4	HMDB
Ox20THLTB4	HMDB

Chemical Formula

C₂₀H₃₀O₇

Average Molecular Weight

382.448

Monoisotopic Molecular Weight

382.199153314

IUPAC Name

(5R,6Z,8E,10E,14Z)-5,20,20,20-tetrahydroxy-12-oxoicosa-6,8,10,14-tetraenoic acid

Traditional Name

(5R,6Z,8E,10E,14Z)-5,20,20,20-tetrahydroxy-12-oxoicosa-6,8,10,14-tetraenoic acid

CAS Registry Number

None

SMILES

O[C@H](CCCC(O)=O)\C=C/C=C/C=C/C(=O)C\C=C/CCCCC(O)(O)O

InChI Identifier

InChI=1S/C20H30O7/c21-17(11-6-2-1-5-9-16-20(25,26)27)12-7-3-4-8-13-18(22)14-10-15-19(23)24/h2-4,6-8,12-13,18,22,25-27H,1,5,9-11,14-16H2,(H,23,24)/b4-3+,6-2-,12-7+,13-8-/t18-/m0/s1

InChI Key

QVZXILIWUPKGPA-CWJNPFRJSA-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
Keto fatty acid
Fatty acid
Unsaturated fatty acid
Acryloyl-group
Enone
Alpha,beta-unsaturated ketone
Secondary alcohol
Ketone
Ortho acid
Orthocarboxylic acid derivative
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Polyol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
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

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0012553)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012553)

Source

Endogenous

Endogenous (HMDB: HMDB0012553)

Animal

Animal (HMDB: HMDB0012553)

Exogenous

Food

Food (HMDB: HMDB0012553)

Exogenous (HMDB: HMDB0012553)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0012553)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0012553)

Lipid metabolism pathway (HMDB: HMDB0012553)

Cellular process

Cell signaling (HMDB: HMDB0012553)

Biochemical process

Lipid transport (HMDB: HMDB0012553)

Role

Biological role

Energy source (HMDB: HMDB0012553)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0012553)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.053 g/L	ALOGPS
logP	2.12	ALOGPS
logP	2.34	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	4.65	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	135.29 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	107.09 m³·mol⁻¹	ChemAxon
Polarizability	41.25 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

HMDB0012553

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029120

KNApSAcK ID

Not Available

Chemspider ID

30776629

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481460

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 12-Oxo-20-trihydroxy-leukotriene B4 (CFc000008030)

MOL for CFc000008030 (12-Oxo-20-trihydroxy-leukotriene B4)

3D MOL for CFc000008030 (12-Oxo-20-trihydroxy-leukotriene B4)

3D SDF for CFc000008030 (12-Oxo-20-trihydroxy-leukotriene B4)

3D-SDF for CFc000008030 (12-Oxo-20-trihydroxy-leukotriene B4)

PDB for CFc000008030 (12-Oxo-20-trihydroxy-leukotriene B4)

3D PDB for CFc000008030 (12-Oxo-20-trihydroxy-leukotriene B4)

SMILES for CFc000008030 (12-Oxo-20-trihydroxy-leukotriene B4)

INCHI for CFc000008030 (12-Oxo-20-trihydroxy-leukotriene B4)

Structure for CFc000008030 (12-Oxo-20-trihydroxy-leukotriene B4)

3D Structure for CFc000008030 (12-Oxo-20-trihydroxy-leukotriene B4)