Doconexent

HCID 445580

Basic information

CAS
25167-62-8
Standard SMILES
CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O
InChIKey
MBMBGCFOFBJSGT-KUBAVDMBSA-N
Molecular formula
C22H32O2
Average molar mass
328.5 g/mol
Monoisotopic mass
328.24023026

Overview

All-cis-docosa-4,7,10,13,16,19-hexaenoic acid is a docosahexaenoic acid having six cis-double bonds at positions 4, 7, 10, 13, 16 and 19. It has a role as an antineoplastic agent, a nutraceutical, a mouse metabolite, a human metabolite, a Daphnia tenebrosa metabolite and an algal metabolite. It is an omega-3 fatty acid and a docosahexaenoic acid. It is a conjugate acid of a (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate.

Names & identifiers

Preferred name
Doconexent
IUPAC
(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid
English name
DOCOSAHEXAENOIC ACID
Molecular formula
C22H32O2
Molecular weight
0

Names & synonyms

DoconexentDoconexentoDoconexentumDoxonexentAquaGrow AdvantageMartek DHA HMRopufa 60Monolife 50CCRIS 7670UNII-ZAD9OKH9JCZAD9OKH9JCDoconexentum [INN-Latin]
Show more names
DHA-FAHY-17031-25gDocosahexaenoic AcidsDocosahexaenoic acid(mix)Docosa-2,4,6,8,10,12-hexaenoic acid(2E,4E,6E,8E,10E,12E)-docosa-2,4,6,8,10,12-hexaenoic acid
Doconexento [INN-Spanish]C22:6 (n-3)22:6 n-3CHEBI:28125Doconexentum (INN-Latin)Doconexento (INN-Spanish)Complete Natal DHAWesNatal DHA Complete

Database identifiers

CAS
25167-62-8、6217-54-5
PubChem CID
445580
DTXSID
DTXSID5040465
ChEMBL
CHEMBL367149
ChEBI
CHEBI:28125
UNII
ZAD9OKH9JC
EC Number
612-950-9
Nikkaji
J381.483A

Properties

Computed structural properties

XLogP
6.2
Topological polar surface area
37.3 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
14
Heavy atoms
24

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
Lipids · 2 items

Lipids -> Unambiguous Lipids

Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Unsaturated fatty acids [FA0103]

CosmeticsAntistatic; Skin conditioning
SpringerMaterials PropertiesChemical diffusion
Physical DescriptionLiquid
Collision Cross Section · 3 items

187.9 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Sample Type: Human bronchoalveolar lavage fluid (BALF); Dataset: Unambiguous Lipids]

184.62 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]

183.5 Ų [M+H]+

Physicochemical properties

Cosmetics Ingredients Functions
ANTISTATICSKIN CONDITIONING
InChI
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/h10-21H,2-9H2,1H3,(H,23,24)/b11-10+,13-12+,15-14+,17-16+,19-18+,21-20+
InChIKey
DVSZKTAMJJTWFG-SKCDLICFSA-N
SMILES
C(O)(=O)/C=C/C=C/C=C/C=C/C=C/C=C/CCCCCCCCC
LogP
7.78 · 7.780 (est)
FDA UNII
9 OKH9JC · ZAD9OKH9JC

Safety & regulation

GHS classification

GHS Classification · 3 items

This chemical does not meet GHS hazard criteria for 98.2% (56 of 57) of all reports.

Not Classified

Aggregated GHS information provided per 57 reports by companies from 2 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 2 items

Docosahexaenoic acid: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

4,7,10,13,16,19-Docosahexaenoic acid, (4Z,7Z,10Z,13Z,16Z,19Z)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Hazard Classes and CategoriesNot Classified

Safety data

Signal word
Warning
Symbol(GHS)
GHS07
Hazard statements
H302-H315-H319-H335
Precautionary statements
P261-P280-P302+P352-P305+P351+P338

Chemistry & industry

Pharmacology

Pharmacodynamics · 1 item

DHA in the central nervous system is found in the phospholipid bilayers where it modulates the physical environment and increase the free volume within the membrane bilayer. It influences the G-protein coupled receptor activity and affects transmembrane transport and cell interaction with the exterior world. It is also reported to promote apoptosis, neuronal differentiation and ion channel activity. Like other polyunsaturated fatty acids, DHA acts as a ligand at PPARs that plays an anti-inflammatory effect and regulate inflammatory gene expression and NFκB activation. DHA also gives rise to resolvins and related compounds (e.g., protectins) through pathways involving cyclooxygenase and lipoxygenase enzymes to resolve the inflammatory responses.

Mechanism of Action · 1 item

DHA and its conversion to other lipid signalling moleccules compete with the arachidonic acid cascade from endogenous phospholipids and shift the inflammatory state to being more anti-inflammatory. DHA inhibits endotoxin-stimulated production of IL-6 and IL-8 in human endothelial cells. Derivatives of DHA are anti-inflammatory lipid mediators. Lipid mediators resolvin D1 and protectin D1 all inhibit transendothelial migration of neutrophils, so preventing neutrophilic infiltration at sites of inflammation, resolvin D1 inhibits IL-1β production, and protectin D1 inhibits TNF and IL-1β production. Monoxydroxy derivative of DHA converted by LOX inhibit thromboxane-induced platelet aggregation. DHA supplementation has also shown to reduce the levels of serum C-reactive protein (CRP) and other circulating markers of inflammation such as neutrophils in hypertriglyceridemic men. DHA acts as a ligand at peroxisome proliferator-activated receptor (PPAR) gamma and alpha that regulate lipid signalling molecule-mediated transduction pathways and modulate inflammation. As a natural ligand, DHA induces a protective effect in retinal tissues by activating retinoid x receptors and subsequent ERK/MAPK signaling pathway in photoreceptors to promote their survival and differentiation, stimulating the expression of antiapoptotic proteins such as Bcl-2 and preserving mitochondrial membrane potential.

Biological Half-LifeApproximately 20 hours.
Metabolism/Metabolites · 1 item

DHA can be metabolized into DHA-derived specialized pro-resolving mediators (SPMs), DHA epoxides, electrophilic oxo-derivatives (EFOX) of DHA, neuroprostanes, ethanolamines, acylglycerols, docosahexaenoyl amides of amino acids or neurotransmitters, and branched DHA esters of hydroxy fatty acids, among others. It is converted to 17-hydroperoxy-DHA derivatives via COX-2 and 15-LOX and 5-LOX activity. These derivatives are further converted into D-series resolvins and protectins with potent anti-inflammatory potential and potent neuroprotective effect. DHA may also be metabolized to 19,20-epoxydocosapentaenoic acids (EDPs) and isomers via CYP2C9 activity. Epoxy metabolites are reported to mediate anti-tumor activity by inhibiting angiogenesis, tumor growth, and metastasis.

Absorption, Distribution and Excretion · 2 items

Like other omega-3 fatty acids, DHA is hydrolyzed from the intestines and delivered through the lymphatic circulation. Plasma DHA concentrations increase in a dose-dependent and saturable manner.

DHA is the most abundant n−3 fatty acid in membranes and is present in all organs. It is also the most variable among organs and is particularly abundant in neural tissue, such as brain and retina, where it is several hundred-fold more abundant than EPA.

Tissue LocationsAdipose Tissue

Uses & manufacturing

UsesUse (kg; approx.) in Germany (2009): ?5000
Use ClassificationCosmetics -> Antistatic; Skin conditioning
Applications · 2 items

UsesDocosahexaenoic acid (DHA) can promote brain development and enhance memory in infants and young children. It can also be used as an antistatic agent, a hair conditioner in cosmetics, and in aquaculture.

DescriptionDocosahexaenoic acid (DHA) is an omega-3 fatty acid found in cold-water, fatty fish, such as salmon.It is also found in fish oil supplements, along with eicosapentaenoic acid (EPA). Vegetarian sources of DHA come from seaweed. Docosahexaenoic acid (DHA) is essential for the growth and functional development of the brain in infants. DHA is also required for maintenance of normal brain function in adults. The inclusion of plentiful DHA in the diet improves learning ability, whereas deficiencies of DHA are associated with deficits in learning. DHA is taken up by the brain in preference to other fatty acids. The turnover of DHA in the brain is very fast, more so than is generally realized. The visual acuity of healthy, full-term, formula-fed infants is increased when their formula includes DHA[1].

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]
郑州阿尔法化工有限公司+86-18530059196 · [email protected]
山西锦洋药用辅料有限公司18234787927
深圳市星凯越生物科技有限公司0755-18589069862 18589069862 · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]

Related reactions

38 records

Compound notes

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