Details of the Drug

General Information of Drug (ID: DM3Z6G4)

Drug Name

5S-HETE

Synonyms

5-Hydroxyeicosatetraenoic acid; 5(S)-HETE; 5-Hete; 5-Hydroxyeicosatetraenoate; 5-Hydroxy-6,8,11,14-eicosatetraenoic acid; UNII-467RNW8T91; 70608-72-9; CHEMBL164813; CHEBI:28209; 5(S)-hydroxyeicosatetraenoic acid; 467RNW8T91; 6,8,11,14-Eicosatetraenoic acid, 5-hydroxy-, (S-(E,Z,Z,Z))-; (5S,6E,8Z,11Z,14Z)-5-hydroxyicosa-6,8,11,14-tetraenoic acid; 5S-hydroxy-6E,8Z,11Z,14Z-eicosatetraenoic acid; (6E,8Z,11Z,14Z)-(5S)-5-Hydroxyicosa-6,8,11,14-tetraenoic acid; 5-(S)-hydroxyeicosatetraenoic acid; AC1NQXIH; BSPBio_001443; 5-(S)-hydroxyeicosatetraenoic acid

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 2

Molecular Weight (mw)

320.5

Logarithm of the Partition Coefficient (xlogp)

5.2

Rotatable Bond Count (rotbonds)

14

Hydrogen Bond Donor Count (hbonddonor)

2

Hydrogen Bond Acceptor Count (hbondacc)

3

Chemical Identifiers

Formula: C20H32O3
IUPAC Name: (5S,6E,8Z,11Z,14Z)-5-hydroxyicosa-6,8,11,14-tetraenoic acid
Canonical SMILES: CCCCC/C=C\\C/C=C\\C/C=C\\C=C\\[C@H](CCCC(=O)O)O
InChI: InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h6-7,9-10,12-14,16,19,21H,2-5,8,11,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,13-12-,16-14+/t19-/m1/s1
InChIKey: KGIJOOYOSFUGPC-JGKLHWIESA-N

Cross-matching ID

PubChem CID: 5280733
ChEBI ID: CHEBI:28209
CAS Number: 330796-62-8
TTD ID: D07CJR

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Arachidonate 5-lipoxygenase (5-LOX)	TT2J34L	LOX5_HUMAN	Inhibitor	[2]
Oxoeicosanoid receptor 1 (OXER1)	TT7WBSV	OXER1_HUMAN	Agonist	[3]
Transient receptor potential cation channel V1 (TRPV1)	TTMI6F5	TRPV1_HUMAN	Activator	[4]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Amyloid-beta precursor protein (APP)	OTKFD7R4	A4_HUMAN	Regulation of Drug Effects	[5]
Bifunctional epoxide hydrolase 2 (EPHX2)	OTPTRCNW	HYES_HUMAN	Gene/Protein Processing	[6]
Mitogen-activated protein kinase 1 (MAPK1)	OTH85PI5	MK01_HUMAN	Post-Translational Modifications	[6]
Mitogen-activated protein kinase 3 (MAPK3)	OTCYKGKO	MK03_HUMAN	Post-Translational Modifications	[6]
Natriuretic peptides B (NPPB)	OTSN2IPY	ANFB_HUMAN	Gene/Protein Processing	[6]
Nuclear factor NF-kappa-B p105 subunit (NFKB1)	OTNRRD8I	NFKB1_HUMAN	Gene/Protein Processing	[6]
Polyunsaturated fatty acid 5-lipoxygenase (ALOX5)	OT7FOIK2	LOX5_HUMAN	Biotransformations	[7]
Transcription factor p65 (RELA)	OTUJP9CN	TF65_HUMAN	Gene/Protein Processing	[6]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease

Discovery agent

ICD Disease Classification

N.A.

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Arachidonate 5-lipoxygenase (5-LOX)	DTT	ALOX5	4.15E-01	-0.06	-0.15

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 3390).
2	Preview of potential therapeutic applications of leukotriene B4 inhibitors in dermatology. Skin Pharmacol Appl Skin Physiol. 2000 Sep-Oct;13(5):235-45.
3	TG1019/OXE, a Galpha(i/o)-protein-coupled receptor, mediates 5-oxo-eicosatetraenoic acid-induced chemotaxis. Biochem Biophys Res Commun. 2005 Sep 9;334(4):987-95.
4	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 507).
5	Amyloid proteotoxicity initiates an inflammatory response blocked by cannabinoids. NPJ Aging Mech Dis. 2016 Jun 23;2:16012. doi: 10.1038/npjamd.2016.12. eCollection 2016.
6	5-, 12- and 15-Hydroxyeicosatetraenoic acids induce cellular hypertrophy in the human ventricular cardiomyocyte, RL-14 cell line, through MAPK- and NF-B-dependent mechanism. Arch Toxicol. 2016 Feb;90(2):359-73.
7	A rat air pouch model for evaluating the efficacy and selectivity of 5-lipoxygenase inhibitors. Eur J Pharmacol. 2008 Apr 14;584(1):166-74.