methyl 2-[(2R,4aS)-4a,8-dimethyl-7-oxo-1,2,3,4-tetrahydronaphthalen-2-yl]prop-2-enoate

Details

• Internal ID: 99ed20cb-f288-4de7-91f7-4fbfd2cbeb84
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: methyl 2-[(2R,4aS)-4a,8-dimethyl-7-oxo-1,2,3,4-tetrahydronaphthalen-2-yl]prop-2-enoate
• SMILES (Canonical): CC1=C2CC(CCC2(C=CC1=O)C)C(=C)C(=O)OC
• SMILES (Isomeric): CC1=C2C[C@@H](CC[C@]2(C=CC1=O)C)C(=C)C(=O)OC
• InChI: InChI=1S/C16H20O3/c1-10(15(18)19-4)12-5-7-16(3)8-6-14(17)11(2)13(16)9-12/h6,8,12H,1,5,7,9H2,2-4H3/t12-,16+/m1/s1
• InChI Key: DRRPONQYYUWLRC-WBMJQRKESA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₀O₃
• Molecular Weight: 260.33 g/mol
• Exact Mass: 260.14124450 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 2.98
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• 2-(2,4a,5,6,7,8-Hexahydro-1,4abeta-dimethyl-2-oxonaphthalene-7beta-yl)acrylic acid methyl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9961	99.61%
Caco-2	+	0.8976	89.76%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7889	78.89%
OATP2B1 inhibitior	-	0.8594	85.94%
OATP1B1 inhibitior	+	0.9126	91.26%
OATP1B3 inhibitior	+	0.9335	93.35%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.8687	86.87%
P-glycoprotein inhibitior	-	0.8553	85.53%
P-glycoprotein substrate	-	0.7854	78.54%
CYP3A4 substrate	+	0.6473	64.73%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9131	91.31%
CYP3A4 inhibition	-	0.7560	75.60%
CYP2C9 inhibition	-	0.7100	71.00%
CYP2C19 inhibition	-	0.5900	59.00%
CYP2D6 inhibition	-	0.9475	94.75%
CYP1A2 inhibition	-	0.6914	69.14%
CYP2C8 inhibition	-	0.7976	79.76%
CYP inhibitory promiscuity	-	0.8649	86.49%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9063	90.63%
Carcinogenicity (trinary)	Non-required	0.5391	53.91%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.8141	81.41%
Skin irritation	-	0.5846	58.46%
Skin corrosion	-	0.9751	97.51%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7781	77.81%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	+	0.5817	58.17%
skin sensitisation	-	0.6177	61.77%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.7302	73.02%
Acute Oral Toxicity (c)	III	0.8206	82.06%
Estrogen receptor binding	-	0.5051	50.51%
Androgen receptor binding	-	0.6301	63.01%
Thyroid receptor binding	-	0.5346	53.46%
Glucocorticoid receptor binding	-	0.5129	51.29%
Aromatase binding	-	0.7316	73.16%
PPAR gamma	+	0.5224	52.24%
Honey bee toxicity	-	0.8829	88.29%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	95.20%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.79%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.34%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.21%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.89%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.25%	94.45%
CHEMBL2581	P07339	Cathepsin D	85.98%	98.95%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.67%	93.03%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.51%	97.09%
CHEMBL5028	O14672	ADAM10	81.19%	97.50%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.06%	93.04%

Plants that contains it

• Kandelia candel

Cross-Links

• PubChem: 14864224
• NPASS: NPC40353
• LOTUS: LTS0124886
• wikiData: Q104987596