16-Hydroxy-9,12,14-octadecatrienoic acid

Details

• Internal ID: 655928d7-c6bd-4cd2-845a-6e84da4575a3
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Lineolic acids and derivatives
• IUPAC Name: 16-hydroxyoctadeca-9,12,14-trienoic acid
• SMILES (Canonical): CCC(C=CC=CCC=CCCCCCCCC(=O)O)O
• SMILES (Isomeric): CCC(C=CC=CCC=CCCCCCCCC(=O)O)O
• InChI: InChI=1S/C18H30O3/c1-2-17(19)15-13-11-9-7-5-3-4-6-8-10-12-14-16-18(20)21/h3,5,9,11,13,15,17,19H,2,4,6-8,10,12,14,16H2,1H3,(H,20,21)
• InChI Key: ILSZLGCGBGSHFR-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₃₀O₃
• Molecular Weight: 294.40 g/mol
• Exact Mass: 294.21949481 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 4.80
• Atomic LogP (AlogP): 4.63
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9815	98.15%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6840	68.40%
OATP2B1 inhibitior	-	0.8536	85.36%
OATP1B1 inhibitior	-	0.4327	43.27%
OATP1B3 inhibitior	+	0.9104	91.04%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.5455	54.55%
P-glycoprotein inhibitior	-	0.8254	82.54%
P-glycoprotein substrate	-	0.9072	90.72%
CYP3A4 substrate	-	0.5731	57.31%
CYP2C9 substrate	-	0.5905	59.05%
CYP2D6 substrate	-	0.8674	86.74%
CYP3A4 inhibition	-	0.9391	93.91%
CYP2C9 inhibition	-	0.8949	89.49%
CYP2C19 inhibition	-	0.9299	92.99%
CYP2D6 inhibition	-	0.9559	95.59%
CYP1A2 inhibition	-	0.6959	69.59%
CYP2C8 inhibition	-	0.8728	87.28%
CYP inhibitory promiscuity	-	0.9198	91.98%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.7335	73.35%
Carcinogenicity (trinary)	Non-required	0.6822	68.22%
Eye corrosion	+	0.6225	62.25%
Eye irritation	+	0.5783	57.83%
Skin irritation	-	0.5833	58.33%
Skin corrosion	-	0.6700	67.00%
Ames mutagenesis	-	0.8500	85.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4617	46.17%
Micronuclear	-	0.9800	98.00%
Hepatotoxicity	-	0.5949	59.49%
skin sensitisation	-	0.5757	57.57%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	-	0.7756	77.56%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.8509	85.09%
Acute Oral Toxicity (c)	III	0.5061	50.61%
Estrogen receptor binding	+	0.6494	64.94%
Androgen receptor binding	-	0.7325	73.25%
Thyroid receptor binding	+	0.6240	62.40%
Glucocorticoid receptor binding	-	0.5773	57.73%
Aromatase binding	-	0.4916	49.16%
PPAR gamma	+	0.8757	87.57%
Honey bee toxicity	-	0.9699	96.99%
Biodegradation	+	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.7589	75.89%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.24%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.62%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.40%	99.17%
CHEMBL1781	P11387	DNA topoisomerase I	87.96%	97.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.13%	96.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.69%	93.56%
CHEMBL221	P23219	Cyclooxygenase-1	83.66%	90.17%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	83.07%	97.21%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	82.52%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.32%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	80.85%	91.11%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.51%	96.95%

Plants that contains it

• Cannabis sativa

Cross-Links

• PubChem: 53922940
• LOTUS: LTS0145927
• wikiData: Q105115456