(4aR,5R,6S)-3-acetyl-6-hydroxy-4a,5-dimethyl-5,6,7,8-tetrahydronaphthalen-2-one

Details

• Internal ID: e92bea2d-a8a6-4b1d-ae77-c75e08299d98
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: (4aR,5R,6S)-3-acetyl-6-hydroxy-4a,5-dimethyl-5,6,7,8-tetrahydronaphthalen-2-one
• SMILES (Canonical): CC1C(CCC2=CC(=O)C(=CC12C)C(=O)C)O
• SMILES (Isomeric): C[C@H]1[C@H](CCC2=CC(=O)C(=C[C@]12C)C(=O)C)O
• InChI: InChI=1S/C14H18O3/c1-8-12(16)5-4-10-6-13(17)11(9(2)15)7-14(8,10)3/h6-8,12,16H,4-5H2,1-3H3/t8-,12-,14+/m0/s1
• InChI Key: COUZLISOMSOQSA-ORUWWINDSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₈O₃
• Molecular Weight: 234.29 g/mol
• Exact Mass: 234.125594432 g/mol
• Topological Polar Surface Area (TPSA): 54.40 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.81
• 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	+	1.0000	100.00%
Caco-2	+	0.8185	81.85%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7858	78.58%
OATP2B1 inhibitior	-	0.8609	86.09%
OATP1B1 inhibitior	+	0.9011	90.11%
OATP1B3 inhibitior	+	0.9709	97.09%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.8934	89.34%
P-glycoprotein inhibitior	-	0.9502	95.02%
P-glycoprotein substrate	-	0.7843	78.43%
CYP3A4 substrate	+	0.6048	60.48%
CYP2C9 substrate	-	0.7411	74.11%
CYP2D6 substrate	-	0.8673	86.73%
CYP3A4 inhibition	-	0.8090	80.90%
CYP2C9 inhibition	-	0.8761	87.61%
CYP2C19 inhibition	-	0.8771	87.71%
CYP2D6 inhibition	-	0.9193	91.93%
CYP1A2 inhibition	-	0.8559	85.59%
CYP2C8 inhibition	-	0.9391	93.91%
CYP inhibitory promiscuity	-	0.9251	92.51%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.4658	46.58%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.9254	92.54%
Skin irritation	+	0.6165	61.65%
Skin corrosion	-	0.9016	90.16%
Ames mutagenesis	-	0.6328	63.28%
Human Ether-a-go-go-Related Gene inhibition	-	0.5628	56.28%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.6301	63.01%
skin sensitisation	+	0.4764	47.64%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.5972	59.72%
Acute Oral Toxicity (c)	III	0.5352	53.52%
Estrogen receptor binding	-	0.7504	75.04%
Androgen receptor binding	+	0.5461	54.61%
Thyroid receptor binding	-	0.6672	66.72%
Glucocorticoid receptor binding	-	0.7383	73.83%
Aromatase binding	-	0.6888	68.88%
PPAR gamma	-	0.7244	72.44%
Honey bee toxicity	-	0.9403	94.03%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9057	90.57%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.84%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	95.15%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.46%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.14%	97.25%
CHEMBL2581	P07339	Cathepsin D	91.81%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.03%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.56%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.96%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.16%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.98%	92.94%
CHEMBL340	P08684	Cytochrome P450 3A4	81.23%	91.19%

Plants that contains it

• Ligularia japonica

Cross-Links

• PubChem: 102280061
• LOTUS: LTS0219742
• wikiData: Q104967315