(3aR,6S,8aS)-6-methyl-3-methylidene-5-[(E)-3-oxobut-1-enyl]-6,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one

Details

• Internal ID: f5ddf5f6-1028-4feb-a715-d598e3184250
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (3aR,6S,8aS)-6-methyl-3-methylidene-5-[(E)-3-oxobut-1-enyl]-6,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one
• SMILES (Canonical): CC1CCC2C(C=C1C=CC(=O)C)C(=C)C(=O)O2
• SMILES (Isomeric): C[C@H]1CC[C@H]2[C@H](C=C1/C=C/C(=O)C)C(=C)C(=O)O2
• InChI: InChI=1S/C15H18O3/c1-9-4-7-14-13(11(3)15(17)18-14)8-12(9)6-5-10(2)16/h5-6,8-9,13-14H,3-4,7H2,1-2H3/b6-5+/t9-,13+,14-/m0/s1
• InChI Key: UXQSNQPHEOKTFP-MRGAMWLOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₃
• Molecular Weight: 246.30 g/mol
• Exact Mass: 246.125594432 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.59
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9951	99.51%
Caco-2	+	0.6924	69.24%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5529	55.29%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8963	89.63%
OATP1B3 inhibitior	+	0.9368	93.68%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.8533	85.33%
P-glycoprotein inhibitior	-	0.9062	90.62%
P-glycoprotein substrate	-	0.8788	87.88%
CYP3A4 substrate	+	0.5299	52.99%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8918	89.18%
CYP3A4 inhibition	-	0.8679	86.79%
CYP2C9 inhibition	-	0.9307	93.07%
CYP2C19 inhibition	-	0.8569	85.69%
CYP2D6 inhibition	-	0.9108	91.08%
CYP1A2 inhibition	+	0.6990	69.90%
CYP2C8 inhibition	-	0.7507	75.07%
CYP inhibitory promiscuity	-	0.9167	91.67%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5993	59.93%
Eye corrosion	-	0.8905	89.05%
Eye irritation	-	0.6972	69.72%
Skin irritation	-	0.5129	51.29%
Skin corrosion	-	0.7964	79.64%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5059	50.59%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.7552	75.52%
skin sensitisation	+	0.5159	51.59%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	-	0.5333	53.33%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.6305	63.05%
Acute Oral Toxicity (c)	III	0.5425	54.25%
Estrogen receptor binding	-	0.7583	75.83%
Androgen receptor binding	-	0.7007	70.07%
Thyroid receptor binding	-	0.7211	72.11%
Glucocorticoid receptor binding	-	0.6080	60.80%
Aromatase binding	-	0.8112	81.12%
PPAR gamma	-	0.8085	80.85%
Honey bee toxicity	-	0.8830	88.30%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9656	96.56%

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	95.69%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.36%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.86%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.84%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.52%	86.33%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.21%	93.03%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.35%	95.50%
CHEMBL2581	P07339	Cathepsin D	80.06%	98.95%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 122182540
• LOTUS: LTS0158081
• wikiData: Q105280987