[(2R)-3-hydroxy-3-methyl-2-[6-(3-methylbut-2-enyl)-1H-indol-3-yl]butyl] (9Z,12Z)-octadeca-9,12-dienoate

Details

• Internal ID: 41e7ee34-9927-4c7d-9f1d-e462a8ef736c
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Lineolic acids and derivatives
• IUPAC Name: [(2R)-3-hydroxy-3-methyl-2-[6-(3-methylbut-2-enyl)-1H-indol-3-yl]butyl] (9Z,12Z)-octadeca-9,12-dienoate
• SMILES (Canonical): CCCCCC=CCC=CCCCCCCCC(=O)OCC(C1=CNC2=C1C=CC(=C2)CC=C(C)C)C(C)(C)O
• SMILES (Isomeric): CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@@H](C1=CNC2=C1C=CC(=C2)CC=C(C)C)C(C)(C)O
• InChI: InChI=1S/C36H55NO3/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-35(38)40-28-33(36(4,5)39)32-27-37-34-26-30(23-22-29(2)3)24-25-31(32)34/h10-11,13-14,22,24-27,33,37,39H,6-9,12,15-21,23,28H2,1-5H3/b11-10-,14-13-/t33-/m0/s1
• InChI Key: BQQKCKIBBZWMIK-ZHSNJTGJSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₅₅NO₃
• Molecular Weight: 549.80 g/mol
• Exact Mass: 549.41819462 g/mol
• Topological Polar Surface Area (TPSA): 62.30 Ų
• XlogP: 10.60
• Atomic LogP (AlogP): 9.89
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 20

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9972	99.72%
Caco-2	-	0.7396	73.96%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6296	62.96%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7888	78.88%
OATP1B3 inhibitior	+	0.9344	93.44%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.9900	99.00%
P-glycoprotein inhibitior	+	0.7780	77.80%
P-glycoprotein substrate	+	0.6859	68.59%
CYP3A4 substrate	+	0.6480	64.80%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8423	84.23%
CYP3A4 inhibition	+	0.5320	53.20%
CYP2C9 inhibition	+	0.5714	57.14%
CYP2C19 inhibition	-	0.5195	51.95%
CYP2D6 inhibition	-	0.8487	84.87%
CYP1A2 inhibition	+	0.6074	60.74%
CYP2C8 inhibition	+	0.6568	65.68%
CYP inhibitory promiscuity	+	0.8872	88.72%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.5525	55.25%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.9393	93.93%
Skin irritation	-	0.7961	79.61%
Skin corrosion	-	0.9487	94.87%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3773	37.73%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.7980	79.80%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.9385	93.85%
Acute Oral Toxicity (c)	III	0.5457	54.57%
Estrogen receptor binding	+	0.7201	72.01%
Androgen receptor binding	+	0.6242	62.42%
Thyroid receptor binding	-	0.5600	56.00%
Glucocorticoid receptor binding	+	0.7154	71.54%
Aromatase binding	+	0.5423	54.23%
PPAR gamma	+	0.5801	58.01%
Honey bee toxicity	-	0.8311	83.11%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.7778	77.78%
Fish aquatic toxicity	+	0.9923	99.23%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	99.43%	94.45%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	99.26%	92.08%
CHEMBL2581	P07339	Cathepsin D	99.25%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	99.06%	99.17%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	96.60%	85.94%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.58%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.18%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	94.29%	91.49%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	93.52%	97.29%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	91.39%	97.21%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	91.30%	96.95%
CHEMBL2535	P11166	Glucose transporter	89.81%	98.75%
CHEMBL3401	O75469	Pregnane X receptor	89.10%	94.73%
CHEMBL1781	P11387	DNA topoisomerase I	88.86%	97.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	88.16%	100.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	88.09%	96.90%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	88.07%	92.68%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	88.02%	92.86%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.24%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.53%	95.89%
CHEMBL213	P08588	Beta-1 adrenergic receptor	84.63%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.69%	89.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.91%	93.03%
CHEMBL2996	Q05655	Protein kinase C delta	81.68%	97.79%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	81.31%	92.88%
CHEMBL340	P08684	Cytochrome P450 3A4	81.03%	91.19%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	80.76%	94.62%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	80.25%	91.81%

Plants that contains it

• Hexalobus crispiflorus
• Isolona congolana
• Xanthium strumarium subsp. strumarium

Cross-Links

• PubChem: 101925114
• NPASS: NPC310350
• LOTUS: LTS0259124
• wikiData: Q104944510