methyl (4aR,5S,6R,8aR)-5,6,8a-trimethyl-5-[2-(5-oxo-2H-furan-4-yl)ethyl]-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate

Details

• Internal ID: f20408f1-bc45-40eb-8b4b-11e3dfacc644
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: methyl (4aR,5S,6R,8aR)-5,6,8a-trimethyl-5-[2-(5-oxo-2H-furan-4-yl)ethyl]-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate
• SMILES (Canonical): CC1CCC2(C(C1(C)CCC3=CCOC3=O)CCC=C2C(=O)OC)C
• SMILES (Isomeric): C[C@@H]1CC[C@@]2([C@@H]([C@@]1(C)CCC3=CCOC3=O)CCC=C2C(=O)OC)C
• InChI: InChI=1S/C21H30O4/c1-14-8-11-21(3)16(19(23)24-4)6-5-7-17(21)20(14,2)12-9-15-10-13-25-18(15)22/h6,10,14,17H,5,7-9,11-13H2,1-4H3/t14-,17-,20+,21+/m1/s1
• InChI Key: SIFADWAWFOYYKC-LPNJYYIDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₀O₄
• Molecular Weight: 346.50 g/mol
• Exact Mass: 346.21440943 g/mol
• Topological Polar Surface Area (TPSA): 52.60 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 4.20
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9929	99.29%
Caco-2	+	0.7843	78.43%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7331	73.31%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8626	86.26%
OATP1B3 inhibitior	+	0.9588	95.88%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.6827	68.27%
P-glycoprotein inhibitior	+	0.5989	59.89%
P-glycoprotein substrate	-	0.6638	66.38%
CYP3A4 substrate	+	0.6612	66.12%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8923	89.23%
CYP3A4 inhibition	-	0.6766	67.66%
CYP2C9 inhibition	-	0.7337	73.37%
CYP2C19 inhibition	-	0.7741	77.41%
CYP2D6 inhibition	-	0.9054	90.54%
CYP1A2 inhibition	-	0.6005	60.05%
CYP2C8 inhibition	+	0.4788	47.88%
CYP inhibitory promiscuity	-	0.6073	60.73%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6243	62.43%
Eye corrosion	-	0.9830	98.30%
Eye irritation	-	0.9096	90.96%
Skin irritation	-	0.6494	64.94%
Skin corrosion	-	0.9556	95.56%
Ames mutagenesis	-	0.6454	64.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.8438	84.38%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.6026	60.26%
skin sensitisation	-	0.8334	83.34%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	+	0.6270	62.70%
Acute Oral Toxicity (c)	III	0.7077	70.77%
Estrogen receptor binding	+	0.6222	62.22%
Androgen receptor binding	+	0.5724	57.24%
Thyroid receptor binding	+	0.6371	63.71%
Glucocorticoid receptor binding	+	0.7232	72.32%
Aromatase binding	+	0.6035	60.35%
PPAR gamma	+	0.5425	54.25%
Honey bee toxicity	-	0.8271	82.71%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
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	98.39%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.02%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.65%	96.09%
CHEMBL2581	P07339	Cathepsin D	92.79%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.92%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.90%	86.33%
CHEMBL4072	P07858	Cathepsin B	85.17%	93.67%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.74%	94.45%
CHEMBL5028	O14672	ADAM10	84.12%	97.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.72%	97.14%
CHEMBL340	P08684	Cytochrome P450 3A4	82.02%	91.19%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.73%	100.00%

Plants that contains it

• Grangea maderaspatana
• Malvaviscus arboreus

Cross-Links

• PubChem: 14037454
• LOTUS: LTS0139639
• wikiData: Q105382681