2-[(E)-2-[(1R,4aS,8aR)-3-hydroxy-2,5,5,8a-tetramethyl-4-oxo-4a,6,7,8-tetrahydro-1H-naphthalen-1-yl]ethenyl]-2H-furan-5-one

Details

• Internal ID: 2af73095-da76-4879-9153-dce6a3d4d762
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: 2-[(E)-2-[(1R,4aS,8aR)-3-hydroxy-2,5,5,8a-tetramethyl-4-oxo-4a,6,7,8-tetrahydro-1H-naphthalen-1-yl]ethenyl]-2H-furan-5-one
• SMILES (Canonical): CC1=C(C(=O)C2C(CCCC2(C1C=CC3C=CC(=O)O3)C)(C)C)O
• SMILES (Isomeric): CC1=C(C(=O)[C@@H]2[C@@]([C@H]1/C=C/C3C=CC(=O)O3)(CCCC2(C)C)C)O
• InChI: InChI=1S/C20H26O4/c1-12-14(8-6-13-7-9-15(21)24-13)20(4)11-5-10-19(2,3)18(20)17(23)16(12)22/h6-9,13-14,18,22H,5,10-11H2,1-4H3/b8-6+/t13?,14-,18-,20+/m0/s1
• InChI Key: BGBIOFODGUKISW-YFTISJBYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₄
• Molecular Weight: 330.40 g/mol
• Exact Mass: 330.18310931 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 3.89
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9897	98.97%
Caco-2	+	0.5769	57.69%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7295	72.95%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8011	80.11%
OATP1B3 inhibitior	+	0.9015	90.15%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.7516	75.16%
P-glycoprotein inhibitior	-	0.6520	65.20%
P-glycoprotein substrate	-	0.8514	85.14%
CYP3A4 substrate	+	0.6071	60.71%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9052	90.52%
CYP3A4 inhibition	-	0.8075	80.75%
CYP2C9 inhibition	-	0.8667	86.67%
CYP2C19 inhibition	-	0.8892	88.92%
CYP2D6 inhibition	-	0.9029	90.29%
CYP1A2 inhibition	-	0.5334	53.34%
CYP2C8 inhibition	-	0.7856	78.56%
CYP inhibitory promiscuity	-	0.8815	88.15%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5097	50.97%
Eye corrosion	-	0.9920	99.20%
Eye irritation	-	0.9686	96.86%
Skin irritation	+	0.5602	56.02%
Skin corrosion	-	0.8627	86.27%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7063	70.63%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.5882	58.82%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.6663	66.63%
Acute Oral Toxicity (c)	III	0.6749	67.49%
Estrogen receptor binding	+	0.7412	74.12%
Androgen receptor binding	+	0.5305	53.05%
Thyroid receptor binding	+	0.6490	64.90%
Glucocorticoid receptor binding	+	0.5848	58.48%
Aromatase binding	+	0.7450	74.50%
PPAR gamma	-	0.5506	55.06%
Honey bee toxicity	-	0.8555	85.55%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9938	99.38%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.29%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.26%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	90.33%	91.49%
CHEMBL1937	Q92769	Histone deacetylase 2	89.84%	94.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.80%	94.45%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	84.50%	93.40%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.73%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.52%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.31%	97.25%
CHEMBL1871	P10275	Androgen Receptor	82.33%	96.43%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.11%	95.89%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	81.27%	90.93%
CHEMBL3012	Q13946	Phosphodiesterase 7A	80.10%	99.29%

Plants that contains it

• Picrasma quassioides

Cross-Links

• PubChem: 5317380
• NPASS: NPC50628