(2R,3aR,5S)-3a-hydroxy-2-(2-methoxypropan-2-yl)-5-prop-2-enyl-2,3,4,5-tetrahydro-1-benzofuran-6-one

Details

• Internal ID: f18aa105-db07-4690-8edf-cd5c4aac56ef
• Taxonomy: Organoheterocyclic compounds > Benzofurans
• IUPAC Name: (2R,3aR,5S)-3a-hydroxy-2-(2-methoxypropan-2-yl)-5-prop-2-enyl-2,3,4,5-tetrahydro-1-benzofuran-6-one
• SMILES (Canonical): CC(C)(C1CC2(CC(C(=O)C=C2O1)CC=C)O)OC
• SMILES (Isomeric): CC(C)([C@H]1C[C@@]2(C[C@@H](C(=O)C=C2O1)CC=C)O)OC
• InChI: InChI=1S/C15H22O4/c1-5-6-10-8-15(17)9-13(14(2,3)18-4)19-12(15)7-11(10)16/h5,7,10,13,17H,1,6,8-9H2,2-4H3/t10-,13+,15+/m0/s1
• InChI Key: RCVGOPRPKQYSPZ-PSOPSSQASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.98
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9906	99.06%
Caco-2	-	0.5706	57.06%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6235	62.35%
OATP2B1 inhibitior	-	0.8528	85.28%
OATP1B1 inhibitior	+	0.8999	89.99%
OATP1B3 inhibitior	+	0.8896	88.96%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8104	81.04%
P-glycoprotein inhibitior	-	0.8929	89.29%
P-glycoprotein substrate	-	0.8151	81.51%
CYP3A4 substrate	+	0.5831	58.31%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8622	86.22%
CYP3A4 inhibition	-	0.6648	66.48%
CYP2C9 inhibition	-	0.8618	86.18%
CYP2C19 inhibition	-	0.7251	72.51%
CYP2D6 inhibition	-	0.9222	92.22%
CYP1A2 inhibition	-	0.7387	73.87%
CYP2C8 inhibition	-	0.8367	83.67%
CYP inhibitory promiscuity	-	0.7837	78.37%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5864	58.64%
Eye corrosion	-	0.9806	98.06%
Eye irritation	-	0.8351	83.51%
Skin irritation	-	0.5807	58.07%
Skin corrosion	-	0.9247	92.47%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8172	81.72%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.5714	57.14%
skin sensitisation	-	0.6982	69.82%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.4553	45.53%
Acute Oral Toxicity (c)	III	0.4088	40.88%
Estrogen receptor binding	+	0.6968	69.68%
Androgen receptor binding	-	0.5874	58.74%
Thyroid receptor binding	-	0.5665	56.65%
Glucocorticoid receptor binding	+	0.6881	68.81%
Aromatase binding	-	0.6251	62.51%
PPAR gamma	-	0.5612	56.12%
Honey bee toxicity	-	0.7364	73.64%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9063	90.63%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.73%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.41%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.02%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.56%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.90%	86.33%
CHEMBL2581	P07339	Cathepsin D	85.92%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.34%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.65%	95.89%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.82%	91.07%
CHEMBL4208	P20618	Proteasome component C5	82.47%	90.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.45%	97.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.70%	89.00%

Plants that contains it

• Illicium tashiroi

Cross-Links

• PubChem: 101672252
• LOTUS: LTS0011704
• wikiData: Q105233993