Details of the Drug

General Information of Drug (ID: DME26RS)

Drug Name
LTB4
Synonyms
Leukotriene B4; LEUKOTRIENE B4; 5,12-Dihete; 71160-24-2; 5,12-Hete; UNII-1HGW4DR56D; (5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid; 1HGW4DR56D; CHEMBL65061; 5S,12R-dihydroxy-6Z,8E,10E,14Z-eicosatetraenoic acid; CHEBI:15647; VNYSSYRCGWBHLG-AMOLWHMGSA-N; [5S,12R]-Dihydroxy-[6Z,8E,10E,14Z]-eicosatetraenoic acid; Leukotriene B; 5(S),12(R)-Dihydroxy-6-cis-8-trans-10-trans-14-cis-eicosatetraenoic Acid; (S-(R*,S*-(E,Z,E,Z)))-5,12-Dihydroxy-6,8,10,14-eicosatetraenoic acid; 6,8,10,14-Eicosatetraenoic acid,; Leukotriene B4 agonist (HIV infection), LTB4 Sweden AB; LEUKOTRIENE_B4
Indication
Disease Entry ICD 11 Status REF
Human immunodeficiency virus infection 1C62 Phase 2 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 336.5
Logarithm of the Partition Coefficient (xlogp) 4.1
Rotatable Bond Count (rotbonds) 14
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 4
Chemical Identifiers
Formula
C20H32O4
IUPAC Name
(5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid
Canonical SMILES
CCCCC/C=C\\C[C@H](/C=C/C=C/C=C\\[C@H](CCCC(=O)O)O)O
InChI
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)/b8-7+,9-6-,14-10+,15-11-/t18-,19-/m1/s1
InChIKey
VNYSSYRCGWBHLG-AMOLWHMGSA-N
Cross-matching ID
PubChem CID
5280492
ChEBI ID
CHEMBL65061
CAS Number
71160-24-2
UNII
1HGW4DR56D
DrugBank ID
DB12961
TTD ID
D0O4NR
INTEDE ID
DR1851
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Leukotriene B4 receptor 1 (LTB4R) TTN53ZF LT4R1_HUMAN Agonist [2]
Leukotriene B4 receptor 2 (LTB4R2) TTVJX54 LT4R2_HUMAN Inhibitor [3]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Leukotriene B4 omega-hydroxylase (CYP4F3)
Main DME 		DEFCMPI CP4F3_HUMAN Substrate [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Actin, aortic smooth muscle (ACTA2) OTEDLG8E ACTA_HUMAN Gene/Protein Processing [5]
Interleukin-8 (CXCL8) OTS7T5VH IL8_HUMAN Gene/Protein Processing [6]
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Molecular Expression Atlas of This Drug

The Studied Disease Human immunodeficiency virus infection
ICD Disease Classification 1C62
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Leukotriene B4 receptor 1 (LTB4R) DTT LTB4R 3.40E-01 0.21 0.53
Leukotriene B4 omega-hydroxylase (CYP4F3) DME CYP4F3 1.08E-02 -3.54E+00 -1.59E+00
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 ClinicalTrials.gov (NCT00251537) A Pilot Study of LTB4 in HIV-1 Infected Adults in LTB4 Sweden AB.
2 LTB4 promotes insulin resistance in obese mice by acting on macrophages, hepatocytes and myocytes. Nat Med. 2015 Mar;21(3):239-47.
3 Diaryl ether/carboxylic acid derivatives of LY255283: Receptor antagonists of leukotriene B4, Bioorg. Med. Chem. Lett. 3(10):1985-1990 (1993).
4 Leukotriene B4: metabolism and signal transduction. Arch Biochem Biophys. 2001 Jan 15;385(2):231-41.
5 Aryl hydrocarbon receptor-ligand axis mediates pulmonary fibroblast migration and differentiation through increased arachidonic acid metabolism. Toxicology. 2016 Aug 31;370:116-126.
6 Leukotriene B4 mediates histamine induction of NF-kappaB and IL-8 in human bronchial epithelial cells. Am J Physiol. 1998 Jun;274(6):L1030-9.