Details of the Drug

General Information of Drug (ID: DMUOQZD)

Drug Name
Arachidonic Acid
Synonyms
arachidonic acid; 506-32-1; arachidonate; (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid; Immunocytophyte; (all-Z)-5,8,11,14-Eicosatetraenoic acid; cis-5,8,11,14-Eicosatetraenoic acid; 5,8,11,14-Eicosatetraenoic acid, (all-Z)-; 5Z,8Z,11Z,14Z-eicosatetraenoic acid; UNII-27YG812J1I; all-cis-5,8,11,14-eicosatetraenoic acid; Arachidonic Acid, 99%; CHEMBL15594; CHEBI:15843; YZXBAPSDXZZRGB-DOFZRALJSA-N; 27YG812J1I; cis,cis,cis,cis-5,8,11,14-Eicosatetraenoic acid; (5Z,8Z,11Z,14Z)-5,8,11,14-Eicosatetraenoic Acid
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 2 Molecular Weight (mw) 304.5
Logarithm of the Partition Coefficient (xlogp) 6.3
Rotatable Bond Count (rotbonds) 14
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 2
Chemical Identifiers
Formula
C20H32O2
IUPAC Name
(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid
Canonical SMILES
CCCCC/C=C\\C/C=C\\C/C=C\\C/C=C\\CCCC(=O)O
InChI
InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15-
InChIKey
YZXBAPSDXZZRGB-DOFZRALJSA-N
Cross-matching ID
PubChem CID
444899
ChEBI ID
CHEBI:15843
CAS Number
506-32-1
DrugBank ID
DB04557
TTD ID
D0HD9P
INTEDE ID
DR0129

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Prostaglandin G/H synthase 1 (COX-1) TT8NGED PGH1_HUMAN Inhibitor [2]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [3]
Prostaglandin G/H synthase 2 (COX-2) DE492CE PGH2_HUMAN Substrate [4]
Prostaglandin G/H synthase 1 (COX-1) DE073H6 PGH1_HUMAN Substrate [5]
Arachidonate 5-lipoxygenase (ALOX5) DE87OZS LOX5_HUMAN Substrate [6]
Arachidonate 12-lipoxygenase (ALOX12B) DEISPU8 LX12B_HUMAN Substrate [7]
Arachidonate 15-lipoxygenase (ALOX15) DEH0J8X LOX15_HUMAN Substrate [8]
Cytochrome P450 4F2 (CYP4F2) DE3GT9C CP4F2_HUMAN Substrate [9]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
14-3-3 protein zeta/delta OT2TKG9P 1433Z_HUMAN Gene/Protein Processing [10]
2-hydroxyacyl-CoA lyase 2 (ILVBL) OTNRRCGY HACL2_HUMAN Gene/Protein Processing [10]
3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase (EBP) OTSMGKXQ EBP_HUMAN Gene/Protein Processing [10]
3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMGCR) OTRT3F3U HMDH_HUMAN Gene/Protein Processing [10]
7-dehydrocholesterol reductase (DHCR7) OTLILBUI DHCR7_HUMAN Gene/Protein Processing [10]
72 kDa type IV collagenase (MMP2) OT5NIWA2 MMP2_HUMAN Gene/Protein Processing [11]
Acyl-CoA 6-desaturase (FADS2) OTUX531P FADS2_HUMAN Gene/Protein Processing [12]
All trans-polyprenyl-diphosphate synthase PDSS2 (PDSS2) OTEOQBMX DLP1_HUMAN Gene/Protein Processing [10]
Amyloid-beta precursor protein (APP) OTKFD7R4 A4_HUMAN Regulation of Drug Effects [13]
Apolipoprotein A-I (APOA1) OT5THARI APOA1_HUMAN Gene/Protein Processing [14]
Molecular Interaction Atlas (MIA) 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
Prostaglandin G/H synthase 1 (COX-1) DTT PTGS1 3.97E-03 0.16 0.43
Arachidonate 12-lipoxygenase (ALOX12B) DME ALOX12B 4.29E-05 -1.81E-01 -5.25E-01
Arachidonate 15-lipoxygenase (ALOX15) DME ALOX15 4.61E-01 -2.18E-02 -1.44E-01
Arachidonate 5-lipoxygenase (ALOX5) DME ALOX5 5.43E-08 4.11E-01 8.14E-01
Cytochrome P450 2C9 (CYP2C9) DME CYP2C9 1.90E-01 -9.81E-03 -5.96E-02
Prostaglandin G/H synthase 2 (COX-2) DME PTGS2 7.93E-04 -2.88E-01 -3.44E-01
Cytochrome P450 4F2 (CYP4F2) DME CYP4F2 2.43E-02 2.94E-02 1.61E-01
Prostaglandin G/H synthase 1 (COX-1) DME PTGS1 3.97E-03 1.56E-01 4.33E-01
Molecular Expression Atlas (MEA) 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: 2391).
2 How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
3 New insights into the structural features and functional relevance of human cytochrome P450 2C9. Part I. Curr Drug Metab. 2009 Dec;10(10):1075-126.
4 PharmGKB summary: very important pharmacogene information for PTGS2. Pharmacogenet Genomics. 2011 Sep;21(9):607-13.
5 Identification and functional characterization of polymorphisms in human cyclooxygenase-1 (PTGS1). Pharmacogenet Genomics. 2007 Feb;17(2):145-60.
6 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.
7 Mitochondrial uncoupling reveals a novel therapeutic opportunity for p53-defective cancers. Nat Commun. 2018 Sep 26;9(1):3931.
8 Effect of human 15-lipoxygenase-1 metabolites on vascular function in mouse mesenteric arteries and hearts. Prostaglandins Other Lipid Mediat. 2013 Oct;106:8-15.
9 Role of cytochrome P450 enzymes in the bioactivation of polyunsaturated fatty acids. Biochim Biophys Acta. 2011 Jan;1814(1):210-22.
10 Arachidonic acid-induced gene expression in colon cancer cells. Carcinogenesis. 2006 Oct;27(10):1950-60.
11 Matrix metalloproteinases of epithelial origin in facial sebum of patients with acne and their regulation by isotretinoin. J Invest Dermatol. 2005 Oct;125(4):673-84. doi: 10.1111/j.0022-202X.2005.23848.x.
12 Regulation of stearoyl-coenzyme A desaturase and fatty acid delta-6 desaturase-2 expression by linoleic acid and arachidonic acid in human sebocytes leads to enhancement of proinflammatory activity but does not affect lipogenesis. Br J Dermatol. 2011 Aug;165(2):269-76.
13 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.
14 Negative regulation of the human apolipoprotein A-I promoter by fibrates can be attenuated by the interaction of the peroxisome proliferator-activated receptor with its response element. J Biol Chem. 1994 Dec 9;269(49):31012-8.