[(1R,2S,3R,4aS,8aS)-3-hydroxy-1,6-dimethyl-4-propan-2-ylidene-2,3,4a,7,8,8a-hexahydro-1H-naphthalen-2-yl] acetate

Details

• Internal ID: 59ecd47f-7466-42d7-ab7d-e6621dd77bae
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(1R,2S,3R,4aS,8aS)-3-hydroxy-1,6-dimethyl-4-propan-2-ylidene-2,3,4a,7,8,8a-hexahydro-1H-naphthalen-2-yl] acetate
• SMILES (Canonical): CC1C2CCC(=CC2C(=C(C)C)C(C1OC(=O)C)O)C
• SMILES (Isomeric): C[C@@H]1[C@H]2CCC(=C[C@H]2C(=C(C)C)[C@H]([C@H]1OC(=O)C)O)C
• InChI: InChI=1S/C17H26O3/c1-9(2)15-14-8-10(3)6-7-13(14)11(4)17(16(15)19)20-12(5)18/h8,11,13-14,16-17,19H,6-7H2,1-5H3/t11-,13-,14-,16-,17+/m1/s1
• InChI Key: SCEHLOUGQMHTKA-RYECPLHJSA-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: 2.80
• Atomic LogP (AlogP): 3.24
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9964	99.64%
Caco-2	+	0.8719	87.19%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7186	71.86%
OATP2B1 inhibitior	-	0.8570	85.70%
OATP1B1 inhibitior	+	0.9183	91.83%
OATP1B3 inhibitior	+	0.9495	94.95%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.7308	73.08%
P-glycoprotein inhibitior	-	0.7993	79.93%
P-glycoprotein substrate	-	0.8909	89.09%
CYP3A4 substrate	+	0.5648	56.48%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8379	83.79%
CYP3A4 inhibition	-	0.9006	90.06%
CYP2C9 inhibition	-	0.7383	73.83%
CYP2C19 inhibition	-	0.7484	74.84%
CYP2D6 inhibition	-	0.8508	85.08%
CYP1A2 inhibition	-	0.6459	64.59%
CYP2C8 inhibition	-	0.8773	87.73%
CYP inhibitory promiscuity	-	0.7960	79.60%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9343	93.43%
Carcinogenicity (trinary)	Non-required	0.5483	54.83%
Eye corrosion	-	0.9864	98.64%
Eye irritation	-	0.9254	92.54%
Skin irritation	-	0.5350	53.50%
Skin corrosion	-	0.9556	95.56%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6795	67.95%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	+	0.7125	71.25%
skin sensitisation	+	0.5702	57.02%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.7918	79.18%
Acute Oral Toxicity (c)	III	0.7177	71.77%
Estrogen receptor binding	-	0.6694	66.94%
Androgen receptor binding	-	0.4867	48.67%
Thyroid receptor binding	-	0.5064	50.64%
Glucocorticoid receptor binding	-	0.7179	71.79%
Aromatase binding	-	0.9262	92.62%
PPAR gamma	-	0.7448	74.48%
Honey bee toxicity	-	0.8682	86.82%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5055	50.55%
Fish aquatic toxicity	+	0.9887	98.87%

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	96.52%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.52%	91.11%
CHEMBL2581	P07339	Cathepsin D	87.77%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.08%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.57%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.03%	85.14%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.19%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	83.04%	91.19%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.76%	89.00%

Plants that contains it

• Verbesina occidentalis

Cross-Links

• PubChem: 162958928
• LOTUS: LTS0170555
• wikiData: Q105250047