ethyl 2-[(1R,2R,5R,7S,8S,11S,12R)-11-acetyloxy-2,8-dihydroxy-7-methoxy-2,8,12-trimethyl-15-oxabicyclo[10.2.1]pentadecan-5-yl]prop-2-enoate

Details

• Internal ID: f17db085-93ac-43b0-9391-4bd9b82fb4c1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: ethyl 2-[(1R,2R,5R,7S,8S,11S,12R)-11-acetyloxy-2,8-dihydroxy-7-methoxy-2,8,12-trimethyl-15-oxabicyclo[10.2.1]pentadecan-5-yl]prop-2-enoate
• SMILES (Canonical): CCOC(=O)C(=C)C1CCC(C2CCC(O2)(C(CCC(C(C1)OC)(C)O)OC(=O)C)C)(C)O
• SMILES (Isomeric): CCOC(=O)C(=C)[C@@H]1CC[C@@]([C@H]2CC[C@@](O2)([C@H](CC[C@]([C@H](C1)OC)(C)O)OC(=O)C)C)(C)O
• InChI: InChI=1S/C25H42O8/c1-8-31-22(27)16(2)18-9-12-23(4,28)19-11-14-25(6,33-19)20(32-17(3)26)10-13-24(5,29)21(15-18)30-7/h18-21,28-29H,2,8-15H2,1,3-7H3/t18-,19-,20+,21+,23-,24+,25-/m1/s1
• InChI Key: DNCNDFBVUIHHRL-GQNHKQCPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₄₂O₈
• Molecular Weight: 470.60 g/mol
• Exact Mass: 470.28796829 g/mol
• Topological Polar Surface Area (TPSA): 112.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 3.07
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9838	98.38%
Caco-2	-	0.5503	55.03%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7275	72.75%
OATP2B1 inhibitior	-	0.8623	86.23%
OATP1B1 inhibitior	+	0.9107	91.07%
OATP1B3 inhibitior	+	0.9574	95.74%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7407	74.07%
BSEP inhibitior	+	0.8042	80.42%
P-glycoprotein inhibitior	-	0.4354	43.54%
P-glycoprotein substrate	-	0.6633	66.33%
CYP3A4 substrate	+	0.7100	71.00%
CYP2C9 substrate	-	0.8042	80.42%
CYP2D6 substrate	-	0.8936	89.36%
CYP3A4 inhibition	+	0.7755	77.55%
CYP2C9 inhibition	-	0.7024	70.24%
CYP2C19 inhibition	-	0.7915	79.15%
CYP2D6 inhibition	-	0.9208	92.08%
CYP1A2 inhibition	-	0.6821	68.21%
CYP2C8 inhibition	+	0.5235	52.35%
CYP inhibitory promiscuity	-	0.8794	87.94%
UGT catelyzed	-	0.8000	80.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6119	61.19%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.8971	89.71%
Skin irritation	+	0.5087	50.87%
Skin corrosion	-	0.9405	94.05%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3897	38.97%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.5887	58.87%
skin sensitisation	-	0.8978	89.78%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.5451	54.51%
Acute Oral Toxicity (c)	III	0.3809	38.09%
Estrogen receptor binding	+	0.8380	83.80%
Androgen receptor binding	+	0.5506	55.06%
Thyroid receptor binding	+	0.5848	58.48%
Glucocorticoid receptor binding	+	0.7713	77.13%
Aromatase binding	+	0.7824	78.24%
PPAR gamma	+	0.6897	68.97%
Honey bee toxicity	-	0.7254	72.54%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5155	51.55%
Fish aquatic toxicity	+	0.9840	98.40%

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	97.83%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.08%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.94%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.63%	91.11%
CHEMBL340	P08684	Cytochrome P450 3A4	89.54%	91.19%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.02%	92.94%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.96%	97.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.11%	92.62%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.94%	96.95%
CHEMBL2996	Q05655	Protein kinase C delta	85.54%	97.79%
CHEMBL3922	P50579	Methionine aminopeptidase 2	84.61%	97.28%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.58%	94.45%
CHEMBL230	P35354	Cyclooxygenase-2	83.80%	89.63%
CHEMBL5028	O14672	ADAM10	83.61%	97.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.15%	95.89%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.92%	89.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.87%	100.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.28%	91.24%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	81.17%	97.50%
CHEMBL259	P32245	Melanocortin receptor 4	81.05%	95.38%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.91%	89.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.44%	91.07%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.12%	100.00%

Plants that contains it

• Abies mariesii

Cross-Links

• PubChem: 102395385
• LOTUS: LTS0221976
• wikiData: Q104977599