Drug Details

General Information of the Drug (ID: DR5834)
Name
Docosahexaenoic acid
Synonyms
Docosahexaenoic acid; Doconexent; Cervonic acid; 6217-54-5; (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid; all-cis-DHA; Doconexento; Doconexentum; Doxonexent; Docosahexaenoate; cis-4,7,10,13,16,19-Docosahexaenoic acid; AquaGrow Advantage; all-Z-Docosahexaenoic acid; Martek DHA HM; Ropufa 60; UNII-ZAD9OKH9JC; all-cis-4,7,10,13,16,19-Docosahexaenoic acid; (4Z,7Z,10Z,13Z,16Z,19Z)-Docosahexaenoic acid; Docosahexaenoic acid (all-Z); CCRIS 7670; ZAD9OKH9JC; all-cis-docosa-4,7,10,13,16,19-hexaenoic acid; DOCOSA-4,7,10,13,16,19-HEXAENOIC ACID; 4,7,10,13,16,19-Docosahexaenoic acid, (all-Z)-; CHEMBL367149; docosahexaenoic acid(DHA); CHEBI:28125; delta4,7,10,13,16,19-Docosahexaenoic acid; 4-cis,7-cis,10-cis,13-cis,16-cis,19-cis-Docosahexaenoic acid; 4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoic acid; (4Z,7Z,10Z,13Z,16Z,19Z)-4,7,10,13,16,19-Docosahexaenoic acid; (all-Z)-4,7,10,13,16,19-Docosahexaenoic acid; OMEGA-3 MARINE TRIGLYCERIDES; MFCD00065722; efalex; NCGC00161345-04; DOCOSAHEXAENOIC ACID (22:6 n-3); 22:6(n-3); cis-4,7,10,13,16,19-Docosahexanoic acid; 4,7,10,13,16,19-Docosahexaenoic acid; C22:6n-3,6,9,12,15,18; Monolife 50; Doconexent [INN]; Marinol D 50TG; 4,7,10,13,16,19-Docosahexaenoic acid, (4Z,7Z,10Z,13Z,16Z,19Z)-; SR-05000002130; Doconexentum [INN-Latin]; Doconexento [INN-Spanish]; DHA-[21,21,22,22,22-d5]; Cervonate; 1fdq; FA 22:6; Algal DHA; cis-4,7,13,16,19-docosahexaenoic acid; Omega 3 fatty acid; all-Z-Docosahexaenoate; Cervonic acid; ; ; DHA; Spectrum5_002062; Docosahexaenoic acid (6CI); DSSTox_CID_20465; DSSTox_RID_79498; DSSTox_GSID_40465; SCHEMBL19577; BSPBio_001298; Docoshexaenoic Acid (Powder); MLS004773950; BML3-B02; GTPL1051; Retriacyl (proposed trade name); DTXSID5040465; BCBcMAP01_000145; HMS1361A20; HMS1791A20; HMS1989A20; HMS3402A20; HMS3649J15; HY-B2167; ZINC4474564; Tox21_111992; BDBM50210259; LMFA01030185; AKOS015962159; AC-1010; CCG-207958; CCG-208135; CS-6261; DB03756; KL-0761; IDI1_033768; 4,7,10,13,16,19-Docosahexaenoate; NCGC00161345-01; NCGC00161345-02; NCGC00161345-03; NCGC00161345-05; NCGC00161345-07; all cis- Docosahexaenoic acid (cis-DHA); M355; SMR001881493; CAS-6217-54-5; cis-4,7,10,13,16,19-Docosahexanoate; D2226; S6454; C06429; AB01563379_01; 217D545; Q423345; SR-05000002130-1; SR-05000002130-4; BRD-K39965020-001-02-6; 4,7,10,13,16,19-Docosahexaenoic acid, (all cis)-; A320050000; cis-4,7,10,13,16,19-Docosahexaenoic acid, >=98%; z,z,z,z,z,z-docosa-4,7,10,13,16,19-hexaenoic acid; (all-Z)-4,7,10,13,16,19-Docosahexaenoic Acid, DHA; 800E8E72-BBF4-46F7-A60B-B8F2B54669C7; C22H32O2 (cis-4,7,10,13,16,19-docosahexaenoic acid); UNII-71M78END5S component MBMBGCFOFBJSGT-KUBAVDMBSA-N; UNII-96GS7P39SN component MBMBGCFOFBJSGT-KUBAVDMBSA-N; UNII-9B22238JYI component MBMBGCFOFBJSGT-KUBAVDMBSA-N; UNII-F85N2YHE4E component MBMBGCFOFBJSGT-KUBAVDMBSA-N; 4,7,10,13,16,19-Docosahexaenoic acid, (all-Z)- (8CI); cis-4,7,10,13,16,19-Docosahexaenoic acid, analytical standard; (4Z,7Z,10Z,13Z,16Z, 19Z)-docosa-4,7,10,13,16,19-hexaenoic acid; (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4, 7,10,13,16,19-hexaenoic acid; (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19- hexaenoic acid; cis-4,7,13,16,19-Docosahexaenoic acid (stabilized with vitamine E); 4,7,10,13,16,19-Docosahexaenoic acid, (4Z,7Z,10Z,13Z,16Z,19Z)- (9CI); 1024594-51-1; cis-4,7,10,13,16,19-Docosahexaenoic acid, 500 mug/mL in ethanol, certified reference material
    Click to Show/Hide
Molecular Type
Small molecule
Disease Hypertriglyceridaemia [ICD-11: 5C80] Approved [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Half-life
The concentration or amount of drug in body reduced by one-half in 20 hours
Metabolism
The drug is metabolized via the COX-2 and 15-LOX and 5-LOX activity
    Click to Show/Hide
    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C22H32O2
PubChem CID
445580
Canonical SMILES
CCC=CCC=CCC=CCC=CCC=CCC=CCCC(=O)O
InChI
1S/C22H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h3-4,6-7,9-10,12-13,15-16,18-19H,2,5,8,11,14,17,20-21H2,1H3,(H,23,24)/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18-
InChIKey
MBMBGCFOFBJSGT-KUBAVDMBSA-N
CAS Number
CAS 6217-54-5
ChEBI ID
CHEBI:28125
TTD Drug ID
D0Q5XX
DrugBank ID
DB03756
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Arsenic trioxide      Realgar and orpiment     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Cleavage CASP3  Molecule Info 
Pathway MAP
                    In-vitro Model HL-60 CVCL_0002 Adult acute myeloid leukemia Homo sapiens
                    Experimental
                    Result(s)		 Docosahexaenoic acid enhances arsenic trioxide-mediated apoptosis in arsenic trioxide-resistant HL-60 cells.
          Isoliquiritigenin      Robinia pseudoacacia     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Biological
                    Regulation		 Up-regulation Cytochrome c release
Up-regulation ROS generation
                    In-vitro Model HCT 116 CVCL_0291 Colon carcinoma Homo sapiens
                    Experimental
                    Result(s)		 Isoliquiritigenin in combination with docosahexaenoic acid has synergistic anticancer effect on human colorectal cancer cells through ROS-mediated regulation of the JNK and cytochrome c release.
Target and Pathway
Target(s) Prostaglandin G/H synthase 1 (COX-1)  Molecule Info  [4]
Prostaglandin G/H synthase 2 (COX-2)  Molecule Info  [4]
BioCyc Aspirin-triggered lipoxin biosynthesis Click to Show/Hide
2 Aspirin triggered resolvin D biosynthesis
3 C20 prostanoid biosynthesis
4 Aspirin triggered resolvin E biosynthesis
KEGG Pathway Arachidonic acid metabolism Click to Show/Hide
2 Metabolic pathways
3 NF-kappa B signaling pathway
4 VEGF signaling pathway
5 TNF signaling pathway
6 Retrograde endocannabinoid signaling
7 Serotonergic synapse
8 Ovarian steroidogenesis
9 Oxytocin signaling pathway
10 Regulation of lipolysis in adipocytes
11 Leishmaniasis
12 Pathways in cancer
13 Chemical carcinogenesis
14 MicroRNAs in cancer
15 Small cell lung cancer
16 Platelet activation
NetPath Pathway IL1 Signaling Pathway Click to Show/Hide
2 TSH Signaling Pathway
3 IL4 Signaling Pathway
4 TGF_beta_Receptor Signaling Pathway
5 IL5 Signaling Pathway
Panther Pathway Endothelin signaling pathway Click to Show/Hide
2 Inflammation mediated by chemokine and cytokine signaling pathway
3 Toll receptor signaling pathway
4 CCKR signaling map ST
Pathwhiz Pathway Arachidonic Acid Metabolism Click to Show/Hide
Pathway Interaction Database Calcineurin-regulated NFAT-dependent transcription in lymphocytes Click to Show/Hide
2 S1P1 pathway
3 C-MYB transcription factor network
4 Signaling mediated by p38-alpha and p38-beta
5 Calcium signaling in the CD4+ TCR pathway
WikiPathways Prostaglandin Synthesis and Regulation Click to Show/Hide
2 Arachidonic acid metabolism
3 Aryl Hydrocarbon Receptor
4 Quercetin and Nf-kB/ AP-1 Induced Cell Apoptosis
5 Spinal Cord Injury
6 Integrated Pancreatic Cancer Pathway
7 Eicosanoid Synthesis
8 Selenium Micronutrient Network
9 Phase 1 - Functionalization of compounds
References
Reference 1 FDA approves EPANOVA for the treatment of adults with severe hypertriglyceridemia
Reference 2 Docosahexaenoic acid enhances arsenic trioxide-mediated apoptosis in arsenic trioxide-resistant HL-60 cells. Blood. 2003 Jun 15;101(12):4990-7.
Reference 3 Synergistic anticancer effect of docosahexaenoic acid and isoliquiritigenin on human colorectal cancer cells through ROS-mediated regulation of the JNK and cytochrome c release. Mol Biol Rep. 2021 Feb;48(2):1171-1180.
Reference 4 Cox-2 inhibitory effects of naturally occurring and modified fatty acids. J Nat Prod. 2001 Jun;64(6):745-9.
 Download Picture         KEGG Link      
 Download Picture         KEGG Link