20-Hydroxyeicosatetraenoic acid

Details

• Internal ID: befb9eea-82e8-4a86-afa7-b304fbaa3c11
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acids and conjugates > Long-chain fatty acids
• IUPAC Name: (5Z,8Z,11Z,14Z)-20-hydroxyicosa-5,8,11,14-tetraenoic acid
• SMILES (Canonical): C(CCC=CCC=CCC=CCC=CCCCC(=O)O)CCO
• SMILES (Isomeric): C(CC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O)CCO
• InChI: InChI=1S/C20H32O3/c21-19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-20(22)23/h1,3-4,6-7,9-10,12,21H,2,5,8,11,13-19H2,(H,22,23)/b3-1-,6-4-,9-7-,12-10-
• InChI Key: NNDIXBJHNLFJJP-DTLRTWKJSA-N
• Popularity: 668 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₂O₃
• Molecular Weight: 320.50 g/mol
• Exact Mass: 320.23514488 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 4.70
• Atomic LogP (AlogP): 5.19
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 15

Synonyms

• 79551-86-3
• 20-Hydroxyeicosatetraenoic acid
• 20-Hydroxy arachidonic acid
• (5Z,8Z,11Z,14Z)-20-Hydroxyicosa-5,8,11,14-tetraenoic acid
• 20-Hydroxyicosatetraenoic acid
• 20-hydroxy-5,8,11,14-eicosatetraenoic acid
• DTXSID601009895
• 20-hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid
• CHEBI:34306
• RefChem:89565
• DTXCID801436327
• 20-Hydroxyarachidonic acid
• 20-Hydroxyeicosatetraeonic acid
• 20-Hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoic acid
• 20-HETE (>80%)
• 5,8,11,14-Eicosatetraenoicacid, 20-hydroxy-, (5Z,8Z,11Z,14Z)-
• 20-Hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate
• (5Z,8Z,11Z,14Z)-20-Hydroxyicosa-5,8,11,14-tetraenoate
• 20-Hydroxyicosatetraenoate
• SCHEMBL505713
• GTPL4103
• orb1989621
• CHEMBL4085458
• 5,8,11,14-Eicosatetraenoic acid, 20-hydroxy-, (all-Z)-
• LMFA03060009
• 20-HETE - 0.01%, in ethanol
• AKOS027327565
• CS-1451
• FH74911
• HY-15598
• 20-hydroxy-5,8,11,14-eicosatetraenoate
• 20-hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoate
• SR-01000946981
• (all-Z)-20-hydroxy-5,8,11,14-Eicosatetraenoate
• SR-01000946981-1
• Q21099666
• (all-Z)-20-hydroxy-5,8,11,14-Eicosatetraenoic acid
• 20-hydroxy-5(Z),8(Z),11(Z),14(Z)-eicosatetraenoic acid
• 20-Hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoic acid, ~100 mug/mL in ethanol, >=90% (HPLC)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9580	95.80%
Caco-2	-	0.7082	70.82%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8064	80.64%
OATP2B1 inhibitior	-	0.8552	85.52%
OATP1B1 inhibitior	-	0.4375	43.75%
OATP1B3 inhibitior	+	0.9325	93.25%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.4949	49.49%
P-glycoprotein inhibitior	-	0.7324	73.24%
P-glycoprotein substrate	-	0.9791	97.91%
CYP3A4 substrate	-	0.6577	65.77%
CYP2C9 substrate	+	0.5995	59.95%
CYP2D6 substrate	-	0.8503	85.03%
CYP3A4 inhibition	-	0.9228	92.28%
CYP2C9 inhibition	-	0.9109	91.09%
CYP2C19 inhibition	-	0.9524	95.24%
CYP2D6 inhibition	-	0.9623	96.23%
CYP1A2 inhibition	-	0.8724	87.24%
CYP2C8 inhibition	-	0.9095	90.95%
CYP inhibitory promiscuity	-	0.9608	96.08%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7600	76.00%
Carcinogenicity (trinary)	Non-required	0.7168	71.68%
Eye corrosion	+	0.7220	72.20%
Eye irritation	+	0.6918	69.18%
Skin irritation	-	0.7031	70.31%
Skin corrosion	-	0.9077	90.77%
Ames mutagenesis	-	0.8700	87.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3715	37.15%
Micronuclear	-	1.0000	100.00%
Hepatotoxicity	-	0.7385	73.85%
skin sensitisation	-	0.8665	86.65%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	-	0.9333	93.33%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	-	0.7594	75.94%
Acute Oral Toxicity (c)	III	0.7474	74.74%
Estrogen receptor binding	+	0.7453	74.53%
Androgen receptor binding	-	0.8475	84.75%
Thyroid receptor binding	+	0.5664	56.64%
Glucocorticoid receptor binding	+	0.5694	56.94%
Aromatase binding	+	0.5989	59.89%
PPAR gamma	+	0.8614	86.14%
Honey bee toxicity	-	0.9808	98.08%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.6669	66.69%
Fish aquatic toxicity	-	0.3957	39.57%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3060	Q9Y345	Glycine transporter 2	96.00%	99.17%
CHEMBL1781	P11387	DNA topoisomerase I	92.36%	97.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.11%	96.09%
CHEMBL2581	P07339	Cathepsin D	88.70%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.70%	91.11%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 5283157
• LOTUS: LTS0197162
• wikiData: Q21099666