[(1S,2S,5S,8R,9R,10S,12R,14S)-10-hydroxy-5,9,14-trimethyl-4-oxo-3,13-dioxatetracyclo[7.5.0.02,6.012,14]tetradecan-8-yl] 3-methylpentanoate

Details

• Internal ID: c37f8e7c-0c44-4402-bdea-78743f82fe57
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: [(1S,2S,5S,8R,9R,10S,12R,14S)-10-hydroxy-5,9,14-trimethyl-4-oxo-3,13-dioxatetracyclo[7.5.0.02,6.012,14]tetradecan-8-yl] 3-methylpentanoate
• SMILES (Canonical): CCC(C)CC(=O)OC1CC2C(C(=O)OC2C3C1(C(CC4C3(O4)C)O)C)C
• SMILES (Isomeric): CCC(C)CC(=O)O[C@@H]1CC2[C@@H](C(=O)O[C@@H]2[C@@H]3[C@@]1([C@H](C[C@@H]4[C@]3(O4)C)O)C)C
• InChI: InChI=1S/C21H32O6/c1-6-10(2)7-16(23)25-14-8-12-11(3)19(24)26-17(12)18-20(14,4)13(22)9-15-21(18,5)27-15/h10-15,17-18,22H,6-9H2,1-5H3/t10?,11-,12?,13-,14+,15+,17-,18+,20+,21+/m0/s1
• InChI Key: QWKAKCREJKJTMQ-TVAZECOCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₂O₆
• Molecular Weight: 380.50 g/mol
• Exact Mass: 380.21988874 g/mol
• Topological Polar Surface Area (TPSA): 85.40 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 2.46
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9813	98.13%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.4715	47.15%
OATP2B1 inhibitior	-	0.8591	85.91%
OATP1B1 inhibitior	+	0.8761	87.61%
OATP1B3 inhibitior	+	0.8192	81.92%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.6786	67.86%
P-glycoprotein inhibitior	-	0.5839	58.39%
P-glycoprotein substrate	+	0.5391	53.91%
CYP3A4 substrate	+	0.6728	67.28%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8504	85.04%
CYP3A4 inhibition	+	0.5928	59.28%
CYP2C9 inhibition	-	0.7755	77.55%
CYP2C19 inhibition	-	0.8165	81.65%
CYP2D6 inhibition	-	0.9510	95.10%
CYP1A2 inhibition	-	0.8588	85.88%
CYP2C8 inhibition	-	0.7840	78.40%
CYP inhibitory promiscuity	-	0.8948	89.48%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5642	56.42%
Eye corrosion	-	0.9873	98.73%
Eye irritation	-	0.9404	94.04%
Skin irritation	-	0.6025	60.25%
Skin corrosion	-	0.8743	87.43%
Ames mutagenesis	-	0.5182	51.82%
Human Ether-a-go-go-Related Gene inhibition	-	0.6562	65.62%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	+	0.6931	69.31%
skin sensitisation	-	0.8214	82.14%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.6081	60.81%
Acute Oral Toxicity (c)	I	0.3335	33.35%
Estrogen receptor binding	+	0.8344	83.44%
Androgen receptor binding	+	0.6146	61.46%
Thyroid receptor binding	+	0.5576	55.76%
Glucocorticoid receptor binding	+	0.7258	72.58%
Aromatase binding	+	0.6280	62.80%
PPAR gamma	+	0.6876	68.76%
Honey bee toxicity	-	0.7620	76.20%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9727	97.27%

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	97.22%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.28%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.44%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.36%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.87%	94.45%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	89.64%	96.47%
CHEMBL218	P21554	Cannabinoid CB1 receptor	89.61%	96.61%
CHEMBL2581	P07339	Cathepsin D	89.54%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.20%	97.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.54%	96.95%
CHEMBL299	P17252	Protein kinase C alpha	86.59%	98.03%
CHEMBL340	P08684	Cytochrome P450 3A4	85.37%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.96%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.04%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.79%	86.33%
CHEMBL2996	Q05655	Protein kinase C delta	83.28%	97.79%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	82.64%	82.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.48%	92.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.28%	99.23%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.64%	96.77%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.05%	97.28%

Plants that contains it

• Pluchea dioscoridis

Cross-Links

• PubChem: 162816870
• LOTUS: LTS0000691
• wikiData: Q105229233