5(S)-Hete

Details

• Internal ID: a32c8263-66da-4239-b324-1380dd9e4031
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Eicosanoids > Hydroxyeicosatetraenoic acids
• IUPAC Name: (5S,6E,8Z,11Z,14Z)-5-hydroxyicosa-6,8,11,14-tetraenoic acid
• SMILES (Canonical): CCCCCC=CCC=CCC=CC=CC(CCCC(=O)O)O
• SMILES (Isomeric): CCCCC/C=C\C/C=C\C/C=C\C=C\[C@H](CCCC(=O)O)O
• InChI: InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h6-7,9-10,12-14,16,19,21H,2-5,8,11,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,13-12-,16-14+/t19-/m1/s1
• InChI Key: KGIJOOYOSFUGPC-JGKLHWIESA-N
• Popularity: 696 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: 5.20
• Atomic LogP (AlogP): 5.19
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 14

Synonyms

• 5S-HETE
• 70608-72-9
• 5-Hete
• 5-Hydroxyeicosatetraenoic acid
• 5-Hydroxy-6,8,11,14-eicosatetraenoic acid
• 5-Hydroxyeicosatetraenoate
• (5S,6E,8Z,11Z,14Z)-5-hydroxyicosa-6,8,11,14-tetraenoic acid
• 5(S)-hydroxyeicosatetraenoic acid
• CHEMBL164813
• CHEBI:28209
• 467RNW8T91
• 6,8,11,14-Eicosatetraenoic acid, 5-hydroxy-, (S-(E,Z,Z,Z))-
• 5-L-Hydroxy-6,8,11,14-eicosatetraenoic acid
• 5S-hydroxy-6E,8Z,11Z,14Z-eicosatetraenoic acid
• 5(S)-Hydroxy-6-trans-8,11,14-cis-eicosatetraenoic acid
• 5(S)-hydroxy-6(E),8(Z),11(Z),14(Z)-eicosatetraenoic acid
• (6E,8Z,11Z,14Z)-(5S)-5-Hydroxyicosa-6,8,11,14-tetraenoic acid
• UNII-467RNW8T91
• 5-(S)-hydroxyeicosatetraenoic acid
• BSPBio_001443
• 5(S)-Hydroxyeicosatetraenoate
• 5-HETE [MI]
• BML1-B01
• GTPL3390
• SCHEMBL1476909
• BCBcMAP01_000020
• 5-HETE, (S)-
• KGIJOOYOSFUGPC-JGKLHWIESA-N
• DTXSID701017281
• HMS1361I05
• HMS1791I05
• HMS1989I05
• HMS3402I05
• BDBM50027525
• LMFA03060002
• IDI1_033913
• 5(S)-HETE Lipid Maps(R) MS Standard
• NCGC00161235-01
• NCGC00161235-02
• NCGC00161235-03
• 5-Hydroxy-6,8,11,14-eicosatetraenoate
• 5S-Hydroxy-6,8,11,14-eicosatetraenoate
• 5-L-Hydroxy-6,8,11,14-eicosatetraenoate
• HY-113434
• CS-0059517
• 5S-Hydroxy-6,8,11,14-eicosatetraenoic acid
• C04805
• SR-01000946914
• Q2823230
• SR-01000946914-1
• 5(S)-Hydroxy-6-trans-8,11,14-cis-eicosatetraenoate
• (S)-(E,Z,Z,Z)-5-hydroxyeicosa-6,8,11,14-tetraenoic acid
• (5S,6E,8Z,11Z,14Z)-5-hydroxyeicosa-6,8,11,14-tetraenoic acid
• 6,8,11,14-Eicosatetraenoic acid, 5-hydroxy-, (5S,6E,8Z,11Z,14Z)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9874	98.74%
Caco-2	-	0.7108	71.08%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6237	62.37%
OATP2B1 inhibitior	-	0.8537	85.37%
OATP1B1 inhibitior	-	0.5251	52.51%
OATP1B3 inhibitior	+	0.8328	83.28%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.5614	56.14%
P-glycoprotein inhibitior	-	0.7644	76.44%
P-glycoprotein substrate	-	0.8874	88.74%
CYP3A4 substrate	-	0.5504	55.04%
CYP2C9 substrate	-	0.5905	59.05%
CYP2D6 substrate	-	0.8674	86.74%
CYP3A4 inhibition	-	0.9015	90.15%
CYP2C9 inhibition	-	0.9132	91.32%
CYP2C19 inhibition	-	0.9359	93.59%
CYP2D6 inhibition	-	0.9424	94.24%
CYP1A2 inhibition	+	0.7040	70.40%
CYP2C8 inhibition	-	0.8520	85.20%
CYP inhibitory promiscuity	-	0.8944	89.44%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.7735	77.35%
Carcinogenicity (trinary)	Non-required	0.7187	71.87%
Eye corrosion	+	0.5094	50.94%
Eye irritation	-	0.5711	57.11%
Skin irritation	+	0.5342	53.42%
Skin corrosion	-	0.6600	66.00%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5661	56.61%
Micronuclear	-	0.9800	98.00%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	+	0.5799	57.99%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	-	0.8217	82.17%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.8292	82.92%
Acute Oral Toxicity (c)	IV	0.6309	63.09%
Estrogen receptor binding	+	0.7703	77.03%
Androgen receptor binding	-	0.7317	73.17%
Thyroid receptor binding	+	0.5898	58.98%
Glucocorticoid receptor binding	+	0.6837	68.37%
Aromatase binding	-	0.5185	51.85%
PPAR gamma	+	0.8748	87.48%
Honey bee toxicity	-	0.9800	98.00%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9570	95.70%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293224	P10636	Microtubule-associated protein tau	125.9 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.39%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	97.88%	99.17%
CHEMBL230	P35354	Cyclooxygenase-2	95.13%	89.63%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.85%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	92.73%	90.17%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	90.85%	92.08%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	89.74%	96.00%
CHEMBL1781	P11387	DNA topoisomerase I	89.51%	97.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	89.35%	93.56%
CHEMBL4227	P25090	Lipoxin A4 receptor	87.85%	100.00%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	86.92%	85.94%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.46%	96.00%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	83.41%	97.29%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	83.21%	100.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 5280733
• LOTUS: LTS0160073
• wikiData: Q2823230