Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0129)
Drug Name
Arachidonic acid
Synonyms
Arachidonic Acid, 99%; Immunocytophyte; YZXBAPSDXZZRGB-DOFZRALJSA-N; arachidonate; arachidonic acid; (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid; (all-Z)-5,8,11,14-Eicosatetraenoic acid; 27YG812J1I; 5,8,11,14-Eicosatetraenoic acid; 5,8,11,14-Eicosatetraenoic acid, (all-Z)-; 506-32-1; 5Z,8Z,11Z,14Z-eicosatetraenoic acid; CHEBI:15843; CHEMBL15594; MFCD00004417; UNII-27YG812J1I; all-cis-5,8,11,14-eicosatetraenoic acid; cis,cis,cis,cis-5,8,11,14-Eicosatetraenoic acid; cis-5,8,11,14-Eicosatetraenoic acid
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 304.5 Topological Polar Surface Area 37.3
Heavy Atom Count 22 Rotatable Bond Count 14
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
444899
PubChem SID
3519 ; 584562 ; 619099 ; 3139094 ; 4265935 ; 7885669 ; 7979717 ; 8145109 ; 10299602 ; 10524489 ; 14800661 ; 24846907 ; 24890733 ; 24890784 ; 24891487 ; 26747902 ; 26753719 ; 26753720 ; 26753721 ; 26758248 ; 36887771 ; 46391417 ; 46392023 ; 46393430 ; 47885166 ; 47959472 ; 48110218 ; 48493842 ; 49681170 ; 49846134 ; 49846384 ; 50107316 ; 50326117 ; 53787885 ; 56311297 ; 56311317 ; 56312730 ; 56312894 ; 56313841 ; 56313927 ; 56365480 ; 57261284 ; 57404647 ; 57646859 ; 85788730 ; 87562313 ; 91011640 ; 92298150 ; 92309955 ; 92713311
ChEBI ID
CHEBI:15843
CAS Number
506-32-1
TTD Drug ID
D0HD9P
Formula
C20H32O2
Canonical SMILES
CCCCCC=CCC=CCC=CCC=CCCCC(=O)O
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
19-HETE DM006895
20839325
Other reaction - Omega-hydroxylation 1 [5]
20-HETE DM006894
5283157
Other reaction - Omega-hydroxylation 1 [5]
AA-CoA DM006896 N. A. Unclear 1 [10]
EET DM006890
123132895
Unclear 1 [5]
Leukotriens DM006893 N. A. Unclear 1 [5]
Prostaglandin H2 DM006892
445049
Unclear 1 [7] , [5]
11,12-DHET DM006891
5283146
Unclear 2 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007489 Arachidonic acid EET Unclear CYP2C8 ... [5]
MR007491 Arachidonic acid Prostaglandin H2 Unclear COX-1 ... [7], [5]
MR007492 Arachidonic acid Leukotriens Unclear Unclear [5]
MR007493 Arachidonic acid 20-HETE Other reaction - Omega-hydroxylation CYP4A11 ... [5]
MR007494 Arachidonic acid 19-HETE Other reaction - Omega-hydroxylation CYP1A1 ... [5]
MR007495 Arachidonic acid AA-CoA Unclear ACSL4 [10]
MR007490 EET 11,12-DHET Unclear Unclear [5]
⏷ Show the Full List of 7 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Arachidonate 12-lipoxygenase (ALOX12B) DME0402 Homo sapiens
LX12B_HUMAN
1.13.11.31
[2]
Arachidonate 15-lipoxygenase (ALOX15) DME0403 Homo sapiens
LOX15_HUMAN
1.13.11.33
[3]
Arachidonate 5-lipoxygenase (ALOX5) DME0201 Homo sapiens
LOX5_HUMAN
1.13.11.34
[4]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[5]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[6]
Cytochrome P450 2J2 (CYP2J2) DME0031 Homo sapiens
CP2J2_HUMAN
1.14.14.24
[5]
Cytochrome P450 4F2 (CYP4F2) DME0025 Homo sapiens
CP4F2_HUMAN
1.14.13.30
[5]
Prostaglandin G/H synthase 1 (COX-1) DME0091 Homo sapiens
PGH1_HUMAN
1.14.99.1
[7]
Prostaglandin G/H synthase 2 (COX-2) DME0114 Homo sapiens
PGH2_HUMAN
1.14.99.1
[8]
⏷ Show the Full List of 9  DME(s)
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Prostaglandin G/H synthase 1 (COX-1) DME0091 Km = 0.0017 microM
PGH1_HUMAN
[9]
Prostaglandin G/H synthase 2 (COX-2) DME0114 Km = 0.0017 microM
PGH2_HUMAN
[9]
References
1 The IUPHAR/BPS Guide to PHARMACOLOGY in 2020: extending immunopharmacology content and introducing the IUPHAR/MMV Guide to MALARIA PHARMACOLOGY. Nucleic Acids Res. 2020 Jan 8;48(D1):D1006-D1021. (Ligand id: 2391).
2 Mitochondrial uncoupling reveals a novel therapeutic opportunity for p53-defective cancers. Nat Commun. 2018 Sep 26;9(1):3931.
3 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.
4 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.
5 Role of cytochrome P450 enzymes in the bioactivation of polyunsaturated fatty acids. Biochim Biophys Acta. 2011 Jan;1814(1):210-22.
6 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.
7 Identification and functional characterization of polymorphisms in human cyclooxygenase-1 (PTGS1). Pharmacogenet Genomics. 2007 Feb;17(2):145-60.
8 PharmGKB summary: very important pharmacogene information for PTGS2. Pharmacogenet Genomics. 2011 Sep;21(9):607-13.
9 Divergent cyclooxygenase responses to fatty acid structure and peroxide level in fish and mammalian prostaglandin H synthases. FASEB J. 2006 Jun;20(8):1097-108.
10 Role of acyl-CoA synthetase ACSL4 in arachidonic acid metabolism

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