[(1S,4aR,6R,8aS)-8a-(hydroxymethyl)-4-methylidene-6-prop-1-en-2-yl-1,2,3,4a,5,6,7,8-octahydronaphthalen-1-yl] acetate

Details

• Internal ID: 52d57708-4b9a-4e01-96eb-0185b1c3e6c6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: [(1S,4aR,6R,8aS)-8a-(hydroxymethyl)-4-methylidene-6-prop-1-en-2-yl-1,2,3,4a,5,6,7,8-octahydronaphthalen-1-yl] acetate
• SMILES (Canonical): CC(=C)C1CCC2(C(CCC(=C)C2C1)OC(=O)C)CO
• SMILES (Isomeric): CC(=C)[C@@H]1CC[C@@]2([C@H](CCC(=C)[C@H]2C1)OC(=O)C)CO
• InChI: InChI=1S/C17H26O3/c1-11(2)14-7-8-17(10-18)15(9-14)12(3)5-6-16(17)20-13(4)19/h14-16,18H,1,3,5-10H2,2,4H3/t14-,15-,16+,17-/m1/s1
• InChI Key: JBGVFWYCWFYYEQ-WCXIOVBPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₆O₃
• Molecular Weight: 278.40 g/mol
• Exact Mass: 278.18819469 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.24
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9927	99.27%
Caco-2	+	0.6379	63.79%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8568	85.68%
OATP2B1 inhibitior	-	0.8558	85.58%
OATP1B1 inhibitior	+	0.9203	92.03%
OATP1B3 inhibitior	+	0.9265	92.65%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	+	0.5500	55.00%
BSEP inhibitior	-	0.6864	68.64%
P-glycoprotein inhibitior	-	0.8758	87.58%
P-glycoprotein substrate	-	0.8033	80.33%
CYP3A4 substrate	+	0.6125	61.25%
CYP2C9 substrate	-	0.8092	80.92%
CYP2D6 substrate	-	0.8657	86.57%
CYP3A4 inhibition	-	0.7748	77.48%
CYP2C9 inhibition	-	0.7202	72.02%
CYP2C19 inhibition	-	0.6165	61.65%
CYP2D6 inhibition	-	0.9227	92.27%
CYP1A2 inhibition	-	0.7137	71.37%
CYP2C8 inhibition	-	0.7898	78.98%
CYP inhibitory promiscuity	-	0.8181	81.81%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6072	60.72%
Eye corrosion	-	0.9872	98.72%
Eye irritation	-	0.5890	58.90%
Skin irritation	-	0.6525	65.25%
Skin corrosion	-	0.9703	97.03%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4525	45.25%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.5646	56.46%
skin sensitisation	-	0.7472	74.72%
Respiratory toxicity	-	0.6444	64.44%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.4603	46.03%
Acute Oral Toxicity (c)	III	0.7135	71.35%
Estrogen receptor binding	+	0.7528	75.28%
Androgen receptor binding	+	0.5303	53.03%
Thyroid receptor binding	-	0.5328	53.28%
Glucocorticoid receptor binding	+	0.7235	72.35%
Aromatase binding	-	0.5743	57.43%
PPAR gamma	-	0.6270	62.70%
Honey bee toxicity	-	0.8040	80.40%
Biodegradation	-	0.5000	50.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9901	99.01%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.84%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.54%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.58%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.38%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	87.99%	91.19%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.86%	96.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.83%	92.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.38%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.10%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.43%	95.50%

Plants that contains it

• Polyachyrus sphaerocephalus

Cross-Links

• PubChem: 14890305
• LOTUS: LTS0119630
• wikiData: Q105124325