(9S,10E,12S,13S,14E,16R)-9,12,13,16-tetrahydroxyoctadeca-10,14-dienoic acid

Details

• Internal ID: ecf4651b-2ac0-4cdd-84eb-1ec49954a5b2
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Lineolic acids and derivatives
• IUPAC Name: (9S,10E,12S,13S,14E,16R)-9,12,13,16-tetrahydroxyoctadeca-10,14-dienoic acid
• SMILES (Canonical): CCC(C=CC(C(C=CC(CCCCCCCC(=O)O)O)O)O)O
• SMILES (Isomeric): CC[C@H](/C=C/[C@@H]([C@H](/C=C/[C@H](CCCCCCCC(=O)O)O)O)O)O
• InChI: InChI=1S/C18H32O6/c1-2-14(19)10-12-16(21)17(22)13-11-15(20)8-6-4-3-5-7-9-18(23)24/h10-17,19-22H,2-9H2,1H3,(H,23,24)/b12-10+,13-11+/t14-,15+,16+,17+/m1/s1
• InChI Key: FJZXLCCATXFBKE-YTWVVPENSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₃₂O₆
• Molecular Weight: 344.40 g/mol
• Exact Mass: 344.21988874 g/mol
• Topological Polar Surface Area (TPSA): 118.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 1.77
• H-Bond Acceptor: 5
• H-Bond Donor: 5
• Rotatable Bonds: 14

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8832	88.32%
Caco-2	-	0.7881	78.81%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7756	77.56%
OATP2B1 inhibitior	-	0.8544	85.44%
OATP1B1 inhibitior	+	0.9076	90.76%
OATP1B3 inhibitior	+	0.9297	92.97%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9109	91.09%
P-glycoprotein inhibitior	-	0.8454	84.54%
P-glycoprotein substrate	-	0.9142	91.42%
CYP3A4 substrate	-	0.5938	59.38%
CYP2C9 substrate	+	0.6040	60.40%
CYP2D6 substrate	-	0.8592	85.92%
CYP3A4 inhibition	-	0.9432	94.32%
CYP2C9 inhibition	-	0.8940	89.40%
CYP2C19 inhibition	-	0.9139	91.39%
CYP2D6 inhibition	-	0.9460	94.60%
CYP1A2 inhibition	-	0.7423	74.23%
CYP2C8 inhibition	-	0.9618	96.18%
CYP inhibitory promiscuity	-	0.9658	96.58%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7820	78.20%
Carcinogenicity (trinary)	Non-required	0.7235	72.35%
Eye corrosion	-	0.7478	74.78%
Eye irritation	-	0.9547	95.47%
Skin irritation	-	0.6817	68.17%
Skin corrosion	-	0.8707	87.07%
Ames mutagenesis	-	0.8778	87.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.3963	39.63%
Micronuclear	-	0.9300	93.00%
Hepatotoxicity	-	0.6821	68.21%
skin sensitisation	-	0.6850	68.50%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	-	0.8317	83.17%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.7454	74.54%
Acute Oral Toxicity (c)	IV	0.5241	52.41%
Estrogen receptor binding	+	0.6760	67.60%
Androgen receptor binding	-	0.7732	77.32%
Thyroid receptor binding	-	0.5220	52.20%
Glucocorticoid receptor binding	+	0.6530	65.30%
Aromatase binding	-	0.6712	67.12%
PPAR gamma	+	0.6336	63.36%
Honey bee toxicity	-	0.9663	96.63%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.7852	78.52%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.54%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.64%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.59%	99.17%
CHEMBL5285	Q99683	Mitogen-activated protein kinase kinase kinase 5	85.91%	92.26%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	85.02%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.05%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.14%	93.56%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	83.11%	97.29%
CHEMBL1781	P11387	DNA topoisomerase I	80.31%	97.00%

Plants that contains it

• Chaenomeles sinensis
• Chaenomeles speciosa

Cross-Links

• PubChem: 102339345
• NPASS: NPC205140