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

General Information of Drug (ID: DR1988)
Drug Name
Alpha-linolenic acid
Synonyms
Industrene 120; Linolenic acid (8CI); a-Linolenic acid; alpha-Linolenate; alpha-Linolenic acid; alpha-Lnn; linolenate; linolenic acid; (9,12,15)-linolenic acid; (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid; (Z,Z,Z)-9,12,15-Octadecatrienoic acid; 463-40-1; 9,12,15-Octadecatrienoic acid; 9,12,15-Octadecatrienoic acid, (Z,Z,Z)-; 9-cis,12-cis,15-cis-Octadecatrienoic acid; 9Z,12Z,15Z-Octadecatrienoic acid; CCRIS 656; UNII-0RBV727H71; all-cis-9,12,15-Octadecatrienoic acid; cis,cis,cis-9,12,15-Octadecatrienoic acid
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 278.4 Topological Polar Surface Area 37.3
Heavy Atom Count 20 Rotatable Bond Count 13
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
5280934
PubChem SID
8662 ; 68740 ; 819802 ; 841483 ; 3139635 ; 7850017 ; 7888669 ; 8144514 ; 8616449 ; 10523461 ; 14750830 ; 17388945 ; 24882198 ; 24882199 ; 24896311 ; 26752891 ; 26752892 ; 29204335 ; 29215108 ; 39289903 ; 46507620 ; 47216552 ; 47588760 ; 48423612 ; 48425247 ; 48496160 ; 50105513 ; 50105514 ; 53787037 ; 57260459 ; 57260460 ; 57299395 ; 57357935 ; 57651877 ; 80135193 ; 85209429 ; 85272559 ; 85787693 ; 87572018 ; 92298206 ; 92309792 ; 99300706 ; 99302224 ; 103167706 ; 104046526 ; 104098240 ; 113854245 ; 124573768 ; 124800395 ; 124890383
ChEBI ID
CHEBI:27432
CAS Number
463-40-1
TTD Drug ID
D0C5SV
Formula
C18H30O2
Canonical SMILES
CCC=CCC=CCC=CCCCCCCCC(=O)O
InChI
1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10H,2,5,8,11-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9-
InChIKey
DTOSIQBPPRVQHS-PDBXOOCHSA-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
18:4n-3 DM003788 N. A. Unclear 1 [4]
20:4n-3 DM003789 N. A. Unclear 2 [4]
20:5n-3 DM003790 N. A. Other reaction - Desaturation 3 [4]
22:5n-3 DM003791 N. A. Unclear 4 [4]
24:5n-3 DM003792
14647861
Unclear 6 [4]
24:6n-3 DM003793
14647862
Unclear 7 [4]
22:6n-3 DM003794 N. A. Oxidation - Beta-oxidation 8 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004144 Alpha-linolenic acid 18:4n-3 Unclear FADS2 [4]
MR004145 18:4n-3 20:4n-3 Unclear Unclear [4]
MR004146 20:4n-3 20:5n-3 Other reaction - Desaturation FADS1 [4]
MR004147 20:5n-3 22:5n-3 Unclear Unclear [4]
MR004148 22:5n-3 24:5n-3 Unclear FADS2 [4]
MR004149 24:5n-3 24:6n-3 Unclear Unclear [4]
MR004150 24:6n-3 22:6n-3 Oxidation - Beta-oxidation Unclear [4]
⏷ 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
Carboxylic ester hydrolase (CEH) DME1112 Butyrivibrio fibrisolvens
A0A317G4I6_BUTFI
3.1.1.1
[2] , [3]
Fatty acid desaturase 1 (FADS1) DME0202 Homo sapiens
FADS1_HUMAN
1.14.19.44
[4]
Fatty acid desaturase 2 (FADS2) DME0203 Homo sapiens
FADS2_HUMAN
1.14.19.3
[4]
Prostaglandin G/H synthase 1 (COX-1) DME0091 Homo sapiens
PGH1_HUMAN
1.14.99.1
[5]
Prostaglandin G/H synthase 2 (COX-2) DME0114 Homo sapiens
PGH2_HUMAN
1.14.99.1
[5]
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 = 0.0031 microM
PGH1_HUMAN
[5]
Prostaglandin G/H synthase 2 (COX-2) DME0114 Km = 0.0031 microM
PGH2_HUMAN
[5]
References
1 Cox-2 inhibitory effects of naturally occurring and modified fatty acids. J Nat Prod. 2001 Jun;64(6):745-9.
2 Immunogenic inhibition of prominent ruminal bacteria as a means to reduce lipolysis and biohydrogenation activity in vitro. Food Chem. 2017 Mar 1;218:372-377.
3 Cell-associated alpha-amylases of butyrate-producing Firmicute bacteria from the human colon. Microbiology. 2006 Nov;152(Pt 11):3281-3290.
4 Metabolism of alpha-linolenic acid in humans
5 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.

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