(9S,10E,12S,13S,14E)-9,12,13-trihydroxy-16-oxooctadeca-10,14-dienoic acid

Details

• Internal ID: f9475b0d-92fd-431d-875b-ba0f67d8e7d8
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Lineolic acids and derivatives
• IUPAC Name: (9S,10E,12S,13S,14E)-9,12,13-trihydroxy-16-oxooctadeca-10,14-dienoic acid
• SMILES (Canonical): CCC(=O)C=CC(C(C=CC(CCCCCCCC(=O)O)O)O)O
• SMILES (Isomeric): CCC(=O)/C=C/[C@@H]([C@H](/C=C/[C@H](CCCCCCCC(=O)O)O)O)O
• InChI: InChI=1S/C18H30O6/c1-2-14(19)10-12-16(21)17(22)13-11-15(20)8-6-4-3-5-7-9-18(23)24/h10-13,15-17,20-22H,2-9H2,1H3,(H,23,24)/b12-10+,13-11+/t15-,16-,17-/m0/s1
• InChI Key: RWRZWXXOIGHLQX-RHCFWTIKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₃₀O₆
• Molecular Weight: 342.40 g/mol
• Exact Mass: 342.20423867 g/mol
• Topological Polar Surface Area (TPSA): 115.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.98
• H-Bond Acceptor: 5
• H-Bond Donor: 4
• Rotatable Bonds: 14

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7960	79.60%
Caco-2	-	0.8155	81.55%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8545	85.45%
OATP2B1 inhibitior	-	0.8567	85.67%
OATP1B1 inhibitior	+	0.9239	92.39%
OATP1B3 inhibitior	+	0.9431	94.31%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8673	86.73%
P-glycoprotein inhibitior	-	0.8200	82.00%
P-glycoprotein substrate	-	0.8580	85.80%
CYP3A4 substrate	-	0.5358	53.58%
CYP2C9 substrate	-	0.5976	59.76%
CYP2D6 substrate	-	0.8914	89.14%
CYP3A4 inhibition	-	0.9217	92.17%
CYP2C9 inhibition	-	0.8995	89.95%
CYP2C19 inhibition	-	0.9221	92.21%
CYP2D6 inhibition	-	0.9434	94.34%
CYP1A2 inhibition	-	0.8093	80.93%
CYP2C8 inhibition	-	0.9011	90.11%
CYP inhibitory promiscuity	-	0.9837	98.37%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8020	80.20%
Carcinogenicity (trinary)	Non-required	0.7406	74.06%
Eye corrosion	-	0.7571	75.71%
Eye irritation	-	0.9249	92.49%
Skin irritation	-	0.7280	72.80%
Skin corrosion	-	0.9204	92.04%
Ames mutagenesis	-	0.8600	86.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6904	69.04%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.7800	78.00%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	-	0.8507	85.07%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.8236	82.36%
Acute Oral Toxicity (c)	III	0.5039	50.39%
Estrogen receptor binding	+	0.6448	64.48%
Androgen receptor binding	-	0.8210	82.10%
Thyroid receptor binding	-	0.5641	56.41%
Glucocorticoid receptor binding	+	0.6694	66.94%
Aromatase binding	-	0.6864	68.64%
PPAR gamma	+	0.5819	58.19%
Honey bee toxicity	-	0.9615	96.15%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.8534	85.34%

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	96.18%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.71%	99.17%
CHEMBL2581	P07339	Cathepsin D	95.68%	98.95%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	84.42%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.05%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.71%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.61%	85.14%
CHEMBL5285	Q99683	Mitogen-activated protein kinase kinase kinase 5	83.24%	92.26%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.15%	96.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.11%	93.56%
CHEMBL221	P23219	Cyclooxygenase-1	81.42%	90.17%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	81.24%	97.29%
CHEMBL4040	P28482	MAP kinase ERK2	80.17%	83.82%

Plants that contains it

• Chaenomeles sinensis
• Chaenomeles speciosa

Cross-Links

• PubChem: 102339346
• NPASS: NPC152818