Doconexent

Details

• Internal ID: 72c930ea-bca5-4152-a3e2-73b597ac0ad0
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acids and conjugates > Very long-chain fatty acids
• IUPAC Name: (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid
• SMILES (Canonical): CCC=CCC=CCC=CCC=CCC=CCC=CCCC(=O)O
• SMILES (Isomeric): CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O
• 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/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-
• InChI Key: MBMBGCFOFBJSGT-KUBAVDMBSA-N
• Popularity: 21,710 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₂O₂
• Molecular Weight: 328.50 g/mol
• Exact Mass: 328.240230259 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 6.20
• Atomic LogP (AlogP): 6.55
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 14

Synonyms

• Doconexent
• Cervonic acid
• 6217-54-5
• cis-4,7,10,13,16,19-Docosahexaenoic acid
• Docosahexaenoate
• Doconexentum
• Doconexento
• Doxonexent
• (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid
• all-cis-DHA
• AquaGrow Advantage
• Martek DHA HM
• efalex
• Ropufa 60
• all-Z-Docosahexaenoic acid
• Docosaheaenoic-acid
• Monolife 50
• Doconexent [INN]
• Marinol D 50TG
• all-cis-4,7,10,13,16,19-Docosahexaenoic acid
• Docosahexaenoic acid (all-Z)
• (4Z,7Z,10Z,13Z,16Z,19Z)-Docosahexaenoic acid
• CCRIS 7670
• UNII-ZAD9OKH9JC
• ZAD9OKH9JC
• DOCOSAHEXANOIC ACID
• all-cis-docosa-4,7,10,13,16,19-hexaenoic acid
• Algal DHA
• DTXSID5040465
• (all-Z)-4,7,10,13,16,19-Docosahexaenoic acid
• CHEBI:28125
• (4Z,7Z,10Z,13Z,16Z,19Z)-4,7,10,13,16,19-Docosahexaenoic acid
• Docosahexaenoic acid (c22:6 n3)
• delta4,7,10,13,16,19-Docosahexaenoic acid
• Doconexentum [INN-Latin]
• 4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoic acid
• Doconexento [INN-Spanish]
• 4-cis,7-cis,10-cis,13-cis,16-cis,19-cis-Docosahexaenoic acid
• FA 22:6
• 4,7,10,13,16,19-Docosahexaenoic acid, (all-Z)-
• C22:6 (n-3)
• CHEMBL367149
• 22:6 n-3
• docosahexaenoic acid(DHA)
• Retriacyl (proposed trade name)
• 22:6(n-3)
• OMEGA-3 MARINE TRIGLYCERIDES
• MFCD00065722
• DOCOSA-4,7,10,13,16,19-HEXAENOIC ACID
• NCGC00161345-04
• DOCOSAHEXAENOIC ACID (22:6 n-3)
• cis-4,7,10,13,16,19-Docosahexanoic acid
• DOCOSAHEXAENOIC ACID (DHA) (C22:6 N3)
• A320050000
• C22:6n-3,6,9,12,15,18
• DOCOSAHEXAENOIC ACID (MART.)
• DOCOSAHEXAENOIC ACID [MART.]
• DOCOSAHEXAENOIC ACID (USP-RS)
• DOCOSAHEXAENOIC ACID [USP-RS]
• SR-05000002130
• Cervonate
• 1fdq
• Docohexanenoic Acid
• Espanova (TN)
• Docosahexanenoic acid
• all-Z-Docosahexaenoate
• Spectrum5_002062
• Docosahexaenoic Acid n-3
• D0Q5XX
• D0R9ZP
• Docosahexaenoic acid (6CI)
• Fatty Acid 22:6 n-3
• SCHEMBL19577
• BSPBio_001298
• Docoshexaenoic Acid (Powder)
• MLS004773950
• BML3-B02
• GTPL1051
• DTXCID3020465
• BCBcMAP01_000145
• CHEBI:36005
• DOCOSAHEXAENOIC ACID [MI]
• DTXSID401018161
• HMS1361A20
• HMS1791A20
• HMS1989A20
• HMS3402A20
• HMS3649J15
• DOCOSAHEXAENOIC ACID [INCI]
• HY-B2167
• DOCOSAHEXAENOIC ACID [VANDF]
• Tox21_111992
• BDBM50210259
• LMFA01030185
• DOCOSAHEXAENOIC ACID [WHO-DD]
• AKOS015962159
• AC-1010
• CCG-207958
• CCG-208135
• CS-6261
• CS-P-00408
• 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)
• BP-29833
• SMR001881493
• CAS-6217-54-5
• Eicosapentaenoic acid/docosa-hexaenoic acid
• cis-4,7,10,13,16,19-Docosahexanoate
• D2226
• S6454
• C06429
• H10987
• AB01563379_01
• Q423345
• DHA-[21,21,22,22,22-d5]
• SR-05000002130-1
• SR-05000002130-4
• BRD-K39965020-001-02-6
• 4,7,10,13,16,19-Docosahexaenoic acid, (all cis)-
• cis-4,7,10,13,16,19-Docosahexaenoic acid, >=98%
• FA(22:6(4Z,7Z,10Z,13Z,16Z,19Z))
• 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
• All-cis-4, 7, 10, 13, 16, 19-Docosahexaenoic Acid
• C22H32O2 (cis-4,7,10,13,16,19-docosahexaenoic acid)
• 4,7,10,13,16,19-Docosahexaenoic acid, (all-Z)- (8CI)
• cis-4,7,10,13,16,19-Docosahexaenoic acid, analytical standard
• Docosa-4Z,7Z,10Z,13Z,16Z,19Z-hexaenoic Acid (22:6, n-3)
• (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)
• DOCOSAHEXAENOIC ACID (DHA) (C22:6) (CONSTITUENT OF KRILL OIL)
• 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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9955	99.55%
Caco-2	-	0.7582	75.82%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Plasma membrane	0.6160	61.60%
OATP2B1 inhibitior	-	0.8570	85.70%
OATP1B1 inhibitior	-	0.3607	36.07%
OATP1B3 inhibitior	-	0.2579	25.79%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8783	87.83%
P-glycoprotein inhibitior	-	0.6248	62.48%
P-glycoprotein substrate	-	0.9781	97.81%
CYP3A4 substrate	-	0.7269	72.69%
CYP2C9 substrate	+	0.6276	62.76%
CYP2D6 substrate	-	0.8766	87.66%
CYP3A4 inhibition	-	0.9440	94.40%
CYP2C9 inhibition	-	0.9094	90.94%
CYP2C19 inhibition	-	0.9717	97.17%
CYP2D6 inhibition	-	0.9640	96.40%
CYP1A2 inhibition	+	0.6216	62.16%
CYP2C8 inhibition	-	0.9687	96.87%
CYP inhibitory promiscuity	-	0.9588	95.88%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6435	64.35%
Carcinogenicity (trinary)	Non-required	0.6635	66.35%
Eye corrosion	+	0.9532	95.32%
Eye irritation	-	0.6852	68.52%
Skin irritation	+	0.7514	75.14%
Skin corrosion	-	0.7017	70.17%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4512	45.12%
Micronuclear	-	0.9900	99.00%
Hepatotoxicity	-	0.8625	86.25%
skin sensitisation	+	0.8140	81.40%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	-	0.7219	72.19%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.8449	84.49%
Acute Oral Toxicity (c)	IV	0.6395	63.95%
Estrogen receptor binding	+	0.7041	70.41%
Androgen receptor binding	-	0.9209	92.09%
Thyroid receptor binding	-	0.5946	59.46%
Glucocorticoid receptor binding	+	0.6682	66.82%
Aromatase binding	+	0.6192	61.92%
PPAR gamma	+	0.7960	79.60%
Honey bee toxicity	-	0.9901	99.01%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	+	0.7885	78.85%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	22387.2 nM; 22387.2 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1978	P11511	Cytochrome P450 19A1	33200 nM	IC50	PMID: 16643058
CHEMBL4422	O14842	Free fatty acid receptor 1	36000 nM; 11700 nM	EC50; EC50	PMID: 24900539; PMID: 27326330
CHEMBL1293224	P10636	Microtubule-associated protein tau	11220.2 nM; 15848.9 nM; 25118.9 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL1628461	Q8TDS5	Oxoeicosanoid receptor 1	2000 nM	IC50	PMID: 24351031
CHEMBL2061	P19793	Retinoid X receptor alpha	0.05 nM	ED50	PMID: 24959987

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.11%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.98%	99.17%
CHEMBL2581	P07339	Cathepsin D	90.37%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	87.98%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.80%	86.33%
CHEMBL1781	P11387	DNA topoisomerase I	80.07%	97.00%

Plants that contains it

• Carthamus tinctorius
• Citrus × aurantium
• Citrus deliciosa
• Xylocarpus granatum

Cross-Links

• PubChem: 445580
• NPASS: NPC270796
• ChEMBL: CHEMBL367149
• LOTUS: LTS0108086
• wikiData: Q423345