[(1R,2S,4aR,8aR)-7-acetyl-1,8a-dimethyl-6-oxo-1,2,3,4,4a,5-hexahydronaphthalen-2-yl] 2-methylprop-2-enoate

Details

• Internal ID: 1866d7c5-f509-48df-9bee-c295edcfa464
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: [(1R,2S,4aR,8aR)-7-acetyl-1,8a-dimethyl-6-oxo-1,2,3,4,4a,5-hexahydronaphthalen-2-yl] 2-methylprop-2-enoate
• SMILES (Canonical): CC1C(CCC2C1(C=C(C(=O)C2)C(=O)C)C)OC(=O)C(=C)C
• SMILES (Isomeric): C[C@H]1[C@H](CC[C@H]2[C@@]1(C=C(C(=O)C2)C(=O)C)C)OC(=O)C(=C)C
• InChI: InChI=1S/C18H24O4/c1-10(2)17(21)22-16-7-6-13-8-15(20)14(12(4)19)9-18(13,5)11(16)3/h9,11,13,16H,1,6-8H2,2-5H3/t11-,13+,16-,18+/m0/s1
• InChI Key: LLFNQWDJWWUKMU-QRKZQPCCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₄O₄
• Molecular Weight: 304.40 g/mol
• Exact Mass: 304.16745924 g/mol
• Topological Polar Surface Area (TPSA): 60.40 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.01
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9921	99.21%
Caco-2	+	0.8205	82.05%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7585	75.85%
OATP2B1 inhibitior	-	0.8616	86.16%
OATP1B1 inhibitior	+	0.9249	92.49%
OATP1B3 inhibitior	+	0.8979	89.79%
MATE1 inhibitior	+	0.7800	78.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.7628	76.28%
P-glycoprotein inhibitior	-	0.6358	63.58%
P-glycoprotein substrate	-	0.7161	71.61%
CYP3A4 substrate	+	0.6308	63.08%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8967	89.67%
CYP3A4 inhibition	+	0.5691	56.91%
CYP2C9 inhibition	-	0.8828	88.28%
CYP2C19 inhibition	-	0.8438	84.38%
CYP2D6 inhibition	-	0.9523	95.23%
CYP1A2 inhibition	-	0.7101	71.01%
CYP2C8 inhibition	-	0.8354	83.54%
CYP inhibitory promiscuity	-	0.8678	86.78%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8943	89.43%
Carcinogenicity (trinary)	Non-required	0.5808	58.08%
Eye corrosion	-	0.9810	98.10%
Eye irritation	-	0.9374	93.74%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9458	94.58%
Ames mutagenesis	-	0.6254	62.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.6984	69.84%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	+	0.7000	70.00%
skin sensitisation	-	0.5698	56.98%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.6377	63.77%
Acute Oral Toxicity (c)	III	0.7372	73.72%
Estrogen receptor binding	+	0.6968	69.68%
Androgen receptor binding	-	0.6630	66.30%
Thyroid receptor binding	+	0.6110	61.10%
Glucocorticoid receptor binding	+	0.5901	59.01%
Aromatase binding	-	0.5101	51.01%
PPAR gamma	-	0.4855	48.55%
Honey bee toxicity	-	0.8169	81.69%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5250	52.50%
Fish aquatic toxicity	+	0.9959	99.59%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	96.17%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.09%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.37%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	92.74%	91.19%
CHEMBL2581	P07339	Cathepsin D	89.69%	98.95%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	86.26%	93.04%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.16%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.73%	99.23%
CHEMBL1951	P21397	Monoamine oxidase A	82.09%	91.49%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.15%	92.94%

Plants that contains it

• Ligularia virgaurea

Cross-Links

• PubChem: 163009429
• LOTUS: LTS0252566
• wikiData: Q105153494