(1R,4aS,8aS)-5,5,8a-trimethyl-1-[2-(5-oxo-2H-furan-3-yl)ethyl]-1,4,4a,6,7,8-hexahydronaphthalene-2-carbaldehyde

Details

• Internal ID: b0ff2329-d00d-4550-bd20-7f81c2d694dd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: (1R,4aS,8aS)-5,5,8a-trimethyl-1-[2-(5-oxo-2H-furan-3-yl)ethyl]-1,4,4a,6,7,8-hexahydronaphthalene-2-carbaldehyde
• SMILES (Canonical): CC1(CCCC2(C1CC=C(C2CCC3=CC(=O)OC3)C=O)C)C
• SMILES (Isomeric): C[C@]12CCCC([C@@H]1CC=C([C@@H]2CCC3=CC(=O)OC3)C=O)(C)C
• InChI: InChI=1S/C20H28O3/c1-19(2)9-4-10-20(3)16(15(12-21)6-8-17(19)20)7-5-14-11-18(22)23-13-14/h6,11-12,16-17H,4-5,7-10,13H2,1-3H3/t16-,17-,20+/m0/s1
• InChI Key: FURMTLFRXKAGLX-ABSDTBQOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₃
• Molecular Weight: 316.40 g/mol
• Exact Mass: 316.20384475 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 4.20
• Atomic LogP (AlogP): 4.23
• H-Bond Acceptor: 3
• 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	+	0.9964	99.64%
Caco-2	+	0.6630	66.30%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7495	74.95%
OATP2B1 inhibitior	-	0.8643	86.43%
OATP1B1 inhibitior	+	0.8024	80.24%
OATP1B3 inhibitior	+	0.9238	92.38%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	+	0.6000	60.00%
BSEP inhibitior	+	0.8638	86.38%
P-glycoprotein inhibitior	-	0.4347	43.47%
P-glycoprotein substrate	-	0.7002	70.02%
CYP3A4 substrate	+	0.6305	63.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9045	90.45%
CYP3A4 inhibition	-	0.7929	79.29%
CYP2C9 inhibition	-	0.7027	70.27%
CYP2C19 inhibition	-	0.6223	62.23%
CYP2D6 inhibition	-	0.8905	89.05%
CYP1A2 inhibition	-	0.5933	59.33%
CYP2C8 inhibition	-	0.5912	59.12%
CYP inhibitory promiscuity	-	0.6337	63.37%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5823	58.23%
Eye corrosion	-	0.9797	97.97%
Eye irritation	-	0.9235	92.35%
Skin irritation	-	0.6087	60.87%
Skin corrosion	-	0.9335	93.35%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7469	74.69%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	+	0.5899	58.99%
skin sensitisation	-	0.6313	63.13%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.6205	62.05%
Acute Oral Toxicity (c)	III	0.7357	73.57%
Estrogen receptor binding	+	0.7388	73.88%
Androgen receptor binding	+	0.5817	58.17%
Thyroid receptor binding	+	0.6047	60.47%
Glucocorticoid receptor binding	+	0.8092	80.92%
Aromatase binding	+	0.5580	55.80%
PPAR gamma	+	0.7629	76.29%
Honey bee toxicity	-	0.7700	77.00%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
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	98.37%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.96%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.22%	97.25%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	93.59%	93.40%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.11%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.42%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.31%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	83.38%	94.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.09%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	81.08%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.75%	96.09%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	80.52%	85.30%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.27%	89.00%

Plants that contains it

• Baccharis trinervis

Cross-Links

• PubChem: 163047680
• LOTUS: LTS0001207
• wikiData: Q105001964