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Details

Stereochemistry ACHIRAL
Molecular Formula C22H32O2
Molecular Weight 328.4883
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 6
Charge 0

SHOW SMILES / InChI
Structure of DOCONEXENT

SMILES

CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O

InChI

InChIKey=MBMBGCFOFBJSGT-KUBAVDMBSA-N
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-

HIDE SMILES / InChI
Molecular Formula C22H32O2
Molecular Weight 328.4883
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 6
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.hsph.harvard.edu/nutritionsource/omega-3-fats/ | https://www.ncbi.nlm.nih.gov/pubmed/24352849 | https://www.fda.gov/Cosmetics/ProductsIngredients/Products/ucm134064.htm

Doconexent (Docosahexaenoic acid, DHA) is an omega-3 fatty acid that is a primary structural component of the human brain, cerebral cortex, skin, and retina. DHA is widely used as a food supplement, and is beleived to support healthy brain development in young childred, prevent cardiovascular disease and cognitive decline during Alzheimer's disease. Most of these claims, however, were not supported by clinical trials. DHA spray is used as a tanner.

CNS Activity

Originator

Approval Year

2007
205
Targets

Targets

Primary TargetPharmacologyConditionPotency
Modulator
828
Modulator
828
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
Unknown

Approved Use

Unknown
Preventing
Approved
8429
Unknown

Approved Use

Unknown
Primary
Phase III
656
Unknown

Approved Use

Unknown
Palliative
Phase III
656
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Discovery of novel brain lipoxygenase products formed from docosahexaenoic acid (22:6w3).
1988
Severe deficiency of docosahexaenoic acid in peroxisomal disorders: a defect of delta 4 desaturation?
1990 Aug
Hydrolysis of phosphatidylethanolamine by human pancreatic phospholipase A2. Effect of bile salts.
1994 Feb
Nutrition and cognitive function.
1997 Apr
Human plasma albumin transports [13C]docosahexaenoic acid in two lipid forms to blood cells.
1997 Aug
Differential distribution and metabolism of arachidonic acid and docosahexaenoic acid by human placental choriocarcinoma (BeWo) cells.
1998 Aug
Evidence for the unique function of docosahexaenoic acid during the evolution of the modern hominid brain.
1999
Low plasma levels of docosahexaenoic acid in patients with liver cirrhosis and its correction with a polyunsaturated fatty acid-enriched soft oil capsule.
1999 Apr
Maternal plasma homocysteine, placenta status and docosahexaenoic acid concentration in erythrocyte phospholipids of the newborn.
1999 Mar
Polyunsaturated fatty acids in the food chain in Europe.
2000 Jan
Is there a relation between docosahexaenoic acid concentration in mothers' milk and visual development in term infants?
2001 Mar
Phytanic acid and docosahexaenoic acid increase the metabolism of all-trans-retinoic acid and CYP26 gene expression in intestinal cells.
2001 Oct 31
Effects of purified eicosapentaenoic acid and docosahexaenoic acid on platelet, fibrinolytic and vascular function in hypertensive type 2 diabetic patients.
2003 Jan
Free fatty acids regulate insulin secretion from pancreatic beta cells through GPR40.
2003 Mar 13
Omega-3 status and cerebrospinal fluid corticotrophin releasing hormone in perpetrators of domestic violence.
2004 Dec 1
Effects of hyperglycemia and hypercapnia on lipid metabolism during complete brain ischemia.
2004 Dec 24
Protective effects of dietary enrichment with docosahexaenoic acid plus protein in 5-fluorouracil-induced intestinal injury in the rat.
2004 May
Rainbow trout (Oncorhynchus mykiss) brain cells biosynthesize novel docosahexaenoic acid-derived resolvins and protectins-Mediator lipidomic analysis.
2005 Dec
Free fatty acids regulate gut incretin glucagon-like peptide-1 secretion through GPR120.
2005 Jan
Differential modulation of the glutamate transporters GLT1, GLAST and EAAC1 by docosahexaenoic acid.
2005 Mar 10
Mechanism of docosahexaenoic acid-induced inhibition of in vitro Abeta1-42 fibrillation and Abeta1-42-induced toxicity in SH-S5Y5 cells.
2009 Oct
TRPA1 is a polyunsaturated fatty acid sensor in mammals.
2012
Four-year placebo-controlled trial of docosahexaenoic acid in X-linked retinitis pigmentosa (DHAX trial): a randomized clinical trial.
2014 Jul
Safety of docosahexaenoic acid (DHA) administered as DHA ethyl ester in a 9-month toxicity study in dogs.
2016 Jun
Highly Cross-Linked Epoxy Nanofiltration Membranes for the Separation of Organic Chemicals and Fish Oil Ethyl Esters.
2016 Sep 14
Bioequivalence Demonstration for Ω-3 Acid Ethyl Ester Formulations: Rationale for Modification of Current Guidance.
2017 Mar
The hydroxylated form of docosahexaenoic acid (DHA-H) modifies the brain lipid composition in a model of Alzheimer's disease, improving behavioral motor function and survival.
2017 Sep
Double-blind, randomized, multicenter phase 2 study of SC411 in children with sickle cell disease (SCOT trial).
2018 Aug 14
[Separation of eicosapentaenoic acid ethyl ester and docosahexaenoic acid ethyl ester by simulated moving bed chromatography].
2018 Sep 8
Patents

Patents

JP1048898A
9
JP1050890A
4
JP1066118A
9
JP1066119A
9
JP1080250A
9
JP2000014392A
12
JP2000032954A
9
JP2000044470A
9
JP2000060439A
4
JP2000060587A
5
JP2000086425A
9
JP2000095683A
9
JP2000128805A
9
JP2000159667A
4
JP2000159682A
4
JP2000159792A
10
JP2000175630A
4
JP2000191525A
9
JP2000212588A
9
JP2000217538A
6
JP2000217582A
9
JP2000239168A
4
JP2000270885A
12
JP2000281572A
9
JP2000290178A
12
JP2000325040A
4
JP2000327570A
9
JP2000342291A
4
JP2001031566A
7
JP2001054396A
10
JP2001072993A
9
JP2001089380A
9
JP2001128642A
6
JP2001164286A
4
JP2001169780A
4
JP2001192328A
9
JP2001199892A
4
JP2001240558A
9
JP2001275656A
4
JP2001286234A
9
JP2001288079A
9
JP2001335794A
4
JP2002058435A
4
JP2002069475A
4
JP2002180082A
4
JP2002345452A
10
JP2002363131A
9
JP2002532687A
6
JP2002536294A
4
JP2003009818A
4
JP2003063942A
9
JP2004307428A
4
JP4761771B2
4
JP4828062B2
6
JPH00222228A
4
JPH02188574A
7
JPH0222228A
4
JPH07233058A
4
JPH0912456A
4
JPS60169418A
4
JPS62258362A
4

Sample Use Guides

In Vivo Use Guide
Doconexent is administered with food or as an oral supplement, or topically with food.
Route of Administration: Other
In Vitro Use Guide
DHA reduces calcium uptake in rat cardiac myocytes exposed to oubain (0.1 mM) after incubation for 4 days with 5 uM DHA added to medium. Calcium uptake was measured after addition of tracer 45Ca2+ to the 1.0 mM calcium in the bathing medium.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:32:21 UTC 2023
Edited
by admin
on Fri Dec 15 15:32:21 UTC 2023
Record UNII
ZAD9OKH9JC
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DOCONEXENT
INN  
INN  
Official Name English
DOCOSAHEXAENOIC ACID [USP-RS]
Common Name English
DOCOSAHEXAENOIC ACID (DHA) (C22:6) (CONSTITUENT OF KRILL OIL) [DSC]
Common Name English
DOCOSAHEXAENOATE
Common Name English
Docosahexaenoic acid [WHO-DD]
Common Name English
C22:6 (N-3)
Common Name English
DOCOSAHEAENOIC-ACID
Common Name English
(ALL-Z)-4,7,10,13,16,19-DOCOSAHEXAENOIC ACID
Common Name English
DOCOSAHEXAENOIC ACID [MART.]
Common Name English
DOCOSAHEXAENOIC ACID-RICH SINGLE CELL OIL
Common Name English
DOCOSAHEXAENOIC ACID
INCI   MART.   MI   VANDF   WHO-DD  
INCI  
Official Name English
DOCOSAHEXANOIC ACID
Common Name English
DOCOSAHEXAENOIC ACID [INCI]
Common Name English
doconexent [INN]
Common Name English
DOCOSAHEXAENOIC ACID [MI]
Common Name English
DOCOSAHEXAENOIC ACID (DHA) (C22:6 N3)
Common Name English
22:6 N-3
Common Name English
22:6
Common Name English
ALL-CIS-DOCOSA-4,7,10,13,16,19-HEXAENOIC ACID
Common Name English
CERVONIC ACID
Common Name English
DOCOSAHEXAENOIC ACID (C22:6 N3)
Common Name English
DOCOSAHEXAENOIC ACID [VANDF]
Common Name English
(4Z,7Z,10Z,13Z,16Z,19Z)-4,7,10,13,16,19-DOCOSAHEXAENOIC ACID
Systematic Name English
DHA
Common Name English
Classification Tree Code System Code
LIVERTOX 319
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
NCI_THESAURUS C493
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
LOINC 75095-0
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
LOINC 90914-3
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
FDA ORPHAN DRUG 432814
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
FDA ORPHAN DRUG 141701
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
LOINC 90908-5
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
LOINC 88999-8
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
LOINC 88998-0
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
LOINC 35174-2
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
FDA ORPHAN DRUG 456414
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
DSLD 1010 (Number of products:2932)
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
NCI_THESAURUS C68345
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
FDA ORPHAN DRUG 454314
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
FDA ORPHAN DRUG 450214
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
LOINC 90911-9
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
DSLD 4096 (Number of products:5)
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
LOINC 88995-6
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID5040465
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
PRIMARY
GRAS Notification (GRN No.)
732
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
PRIMARY
CAS
25167-62-8
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
NON-SPECIFIC STEREOCHEMISTRY
RXCUI
1006469
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
ALTERNATIVE
MERCK INDEX
m4713
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
PRIMARY Merck Index
CAS
25377-50-8
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
SUPERSEDED
DAILYMED
ZAD9OKH9JC
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
PRIMARY
FDA UNII
ZAD9OKH9JC
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
PRIMARY
CHEBI
36005
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
PRIMARY
SMS_ID
100000144929
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
PRIMARY
CAS
2091-24-9
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
NON-SPECIFIC STEREOCHEMISTRY
DRUG BANK
DB03756
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
PRIMARY
WIKIPEDIA
DOCOSAHEXAENOIC ACID
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
PRIMARY
CHEBI
28125
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
PRIMARY
RXCUI
144450
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
PRIMARY
INN
6428
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
PRIMARY
GRAS Notification (GRN No.)
731
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
PRIMARY
CAS
6217-54-5
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
PRIMARY
EVMPD
SUB121918
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
PRIMARY
RXCUI
73
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
ALTERNATIVE
DRUG CENTRAL
4289
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
PRIMARY
PUBCHEM
445580
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
PRIMARY
ChEMBL
CHEMBL367149
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
PRIMARY
NCI_THESAURUS
C68346
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
PRIMARY
RS_ITEM_NUM
1224609
Created by admin on Fri Dec 15 15:32:21 UTC 2023 , Edited by admin on Fri Dec 15 15:32:21 UTC 2023
PRIMARY
Related Record Type Details
Structure of EDASALONEXENT
DERIVATIVE -> PARENT
COD LIVER OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
Structure of Doconexent lysine salt
SALT/SOLVATE -> PARENT
KRILL OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
Structure of DOCONEXENT SODIUM
SALT/SOLVATE -> PARENT
FISH OIL
LIPID -> FATTY ACID
Related Record Type Details
Structure of DOCONEXENT
ACTIVE MOIETY
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