[(2R,4aR,5R,8R,8aS)-5-hydroxy-3,8-dimethyl-5-propan-2-yl-2,4a,6,7,8,8a-hexahydro-1H-naphthalen-2-yl] acetate

Details

• Internal ID: 8c341a12-b6d3-46e1-a693-e0216b719951
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(2R,4aR,5R,8R,8aS)-5-hydroxy-3,8-dimethyl-5-propan-2-yl-2,4a,6,7,8,8a-hexahydro-1H-naphthalen-2-yl] acetate
• SMILES (Canonical): CC1CCC(C2C1CC(C(=C2)C)OC(=O)C)(C(C)C)O
• SMILES (Isomeric): C[C@@H]1CC[C@]([C@@H]2[C@H]1C[C@H](C(=C2)C)OC(=O)C)(C(C)C)O
• InChI: InChI=1S/C17H28O3/c1-10(2)17(19)7-6-11(3)14-9-16(20-13(5)18)12(4)8-15(14)17/h8,10-11,14-16,19H,6-7,9H2,1-5H3/t11-,14+,15+,16-,17-/m1/s1
• InChI Key: CPTQILMAQBXIFM-RDZAWVCESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₈O₃
• Molecular Weight: 280.40 g/mol
• Exact Mass: 280.20384475 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 3.32
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 2

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	+	0.7253	72.53%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8679	86.79%
OATP2B1 inhibitior	-	0.8510	85.10%
OATP1B1 inhibitior	+	0.9254	92.54%
OATP1B3 inhibitior	+	0.9568	95.68%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	-	0.8069	80.69%
P-glycoprotein inhibitior	-	0.8468	84.68%
P-glycoprotein substrate	-	0.6551	65.51%
CYP3A4 substrate	+	0.6064	60.64%
CYP2C9 substrate	-	0.7948	79.48%
CYP2D6 substrate	-	0.8666	86.66%
CYP3A4 inhibition	-	0.7848	78.48%
CYP2C9 inhibition	-	0.7572	75.72%
CYP2C19 inhibition	-	0.6834	68.34%
CYP2D6 inhibition	-	0.9505	95.05%
CYP1A2 inhibition	-	0.8822	88.22%
CYP2C8 inhibition	-	0.8198	81.98%
CYP inhibitory promiscuity	-	0.9029	90.29%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9743	97.43%
Carcinogenicity (trinary)	Non-required	0.5607	56.07%
Eye corrosion	-	0.9941	99.41%
Eye irritation	-	0.8968	89.68%
Skin irritation	+	0.6463	64.63%
Skin corrosion	-	0.9712	97.12%
Ames mutagenesis	-	0.8270	82.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4412	44.12%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.6877	68.77%
skin sensitisation	+	0.5641	56.41%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.7660	76.60%
Acute Oral Toxicity (c)	III	0.7836	78.36%
Estrogen receptor binding	-	0.4914	49.14%
Androgen receptor binding	-	0.5145	51.45%
Thyroid receptor binding	+	0.5154	51.54%
Glucocorticoid receptor binding	+	0.5712	57.12%
Aromatase binding	-	0.7941	79.41%
PPAR gamma	-	0.5595	55.95%
Honey bee toxicity	-	0.7425	74.25%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5855	58.55%
Fish aquatic toxicity	+	0.9955	99.55%

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	96.82%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.82%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.46%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.79%	98.95%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	93.64%	94.80%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.92%	94.45%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.13%	93.56%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.02%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.15%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.83%	91.19%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.67%	82.69%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	81.58%	86.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.46%	97.09%

Plants that contains it

• Artemisia annua

Cross-Links

• PubChem: 21575639
• NPASS: NPC308508
• LOTUS: LTS0130182
• wikiData: Q105124836