Adrenic Acid

Details

• Internal ID: b1e50f5f-205c-47c7-9dff-5e10cd40ff0c
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acids and conjugates > Very long-chain fatty acids
• IUPAC Name: (7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoic acid
• InChI: InChI=1S/C22H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21H2,1H3,(H,23,24)/b7-6-,10-9-,13-12-,16-15-
• InChI Key: TWSWSIQAPQLDBP-DOFZRALJSA-N
• Popularity: 532 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₆O₂
• Molecular Weight: 332.50 g/mol
• Exact Mass: 332.271530387 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 7.40
• Atomic LogP (AlogP): 7.00
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 16

Synonyms

• RefChem:915189
• 2091-25-0
• 28874-58-0
• (7Z,10Z,13Z,16Z)-Docosa-7,10,13,16-tetraenoic acid
• 7Z,10Z,13Z,16Z-Docosatetraenoic acid
• cis-7,10,13,16-Docosatetraenoic acid
• SODIUM DOCOSATETRAENOATE
• 7,10,13,16-Docosatetraenoic acid
• all-cis-7,10,13,16-Docosatetraenoic acid
• 7,10,13,16-Docosatetraenoic acid, (all-Z)-
• all-cis-docosa-7,10,13,16-tetraenoic acid
• (All-Z)-7,10,13,16-docosatetraenoic acid
• Adrenic Acid (22:4, n-6)
• FA 22:4
• 7,10,13,16-docosatetraenoic acid, (7Z,10Z,13Z,16Z)-
• 2692623-45-1
• C22:4n-6,9,12,15
• 64F675W6EN
• MFCD00673435
• SCHEMBL19452
• BSPBio_001499
• BML3-C01
• orb1307112
• orb3141160
• CHEMBL1491103
• CHEBI:53487
• MSK1771
• 7,10,13,16-Docosatetraenoate
• TWSWSIQAPQLDBP-DOFZRALJSA-N
• HMS1361K21
• HMS1791K21
• HMS1989K21
• HMS3402K21
• HMS3649J13
• (7Z,10Z,13Z,16Z)-7,10,13,16-DOCOSATETRAENOIC ACID
• Adrenic Acid (Solution In Ethanol)
• LMFA01030178
• 7Z,10Z,13Z,16Z-Docosatetraenoate
• ADRENIC ACID (22:4 n-6)
• AKOS037646461
• EBC-616092
• 22:4n6
• IDI1_033969
• NCGC00161352-01
• NCGC00161352-02
• NCGC00161352-03
• AS-68942
• BP-40909
• Delta7,10,13,16-Docosatetraenoic acid
• FD178368
• NS00074065
• T19180
• F865909
• FA(22:4(7Z,10Z,13Z,16Z))
• SR-01000946666
• 7,10,13,16-Docosatetraenoic acid (VAN) Adrenate
• cis,cis,cis,cis-Docosa-7,10,13,16-tetraensaeure
• Q4351606
• SR-01000946666-1
• BRD-K17040651-001-02-0
• 7,10,13,16-Docosatetraenoic acid (VAN) Adrenic acid
• 7,10,13,16-Docosatetraenoic acid, (all-Z)- (8CI)
• cis-7,10,13,16-Docosatetraenoic acid, >=98% (GC)
• 7,10,13,16-Docosatetraenoic acid, (7Z,10Z,13Z,16Z)- (9CI)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9947	99.47%
Caco-2	-	0.6857	68.57%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Plasma membrane	0.5465	54.65%
OATP2B1 inhibitior	-	0.8541	85.41%
OATP1B1 inhibitior	-	0.6267	62.67%
OATP1B3 inhibitior	-	0.5698	56.98%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8193	81.93%
P-glycoprotein inhibitior	-	0.6063	60.63%
P-glycoprotein substrate	-	0.9531	95.31%
CYP3A4 substrate	-	0.6641	66.41%
CYP2C9 substrate	+	0.6276	62.76%
CYP2D6 substrate	-	0.8766	87.66%
CYP3A4 inhibition	-	0.9295	92.95%
CYP2C9 inhibition	-	0.8972	89.72%
CYP2C19 inhibition	-	0.9467	94.67%
CYP2D6 inhibition	-	0.9545	95.45%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	-	0.8932	89.32%
CYP inhibitory promiscuity	-	0.9349	93.49%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7035	70.35%
Carcinogenicity (trinary)	Non-required	0.7021	70.21%
Eye corrosion	+	0.9611	96.11%
Eye irritation	+	0.6506	65.06%
Skin irritation	+	0.8622	86.22%
Skin corrosion	+	0.6450	64.50%
Ames mutagenesis	-	0.9900	99.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4655	46.55%
Micronuclear	-	1.0000	100.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	+	0.8676	86.76%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	-	0.7866	78.66%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.7711	77.11%
Acute Oral Toxicity (c)	IV	0.8289	82.89%
Estrogen receptor binding	+	0.7083	70.83%
Androgen receptor binding	-	0.8475	84.75%
Thyroid receptor binding	+	0.5377	53.77%
Glucocorticoid receptor binding	+	0.5499	54.99%
Aromatase binding	-	0.5152	51.52%
PPAR gamma	+	0.8286	82.86%
Honey bee toxicity	-	0.9963	99.63%
Biodegradation	+	0.5250	52.50%
Crustacea aquatic toxicity	+	0.8400	84.00%
Fish aquatic toxicity	+	0.9649	96.49%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	158.5 nM	Potency	via Super-PRED
CHEMBL4422	O14842	Free fatty acid receptor 1	540 nM	EC50	via Super-PRED
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	316.23 nM	EC50	via Super-PRED
CHEMBL239	Q07869	Peroxisome proliferator-activated receptor alpha	4.8 nM	Kd	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	177.8 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3060	Q9Y345	Glycine transporter 2	98.02%	99.17%
CHEMBL2581	P07339	Cathepsin D	96.79%	98.95%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	95.05%	92.08%
CHEMBL230	P35354	Cyclooxygenase-2	94.84%	89.63%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.03%	96.09%
CHEMBL1781	P11387	DNA topoisomerase I	92.92%	97.00%
CHEMBL221	P23219	Cyclooxygenase-1	90.48%	90.17%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	88.44%	85.94%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.54%	93.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.76%	96.95%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 5497181
• LOTUS: LTS0043938
• wikiData: Q4351606