1-[(1R,3S,3aS,5'S,7aR)-5'-ethenyl-7a-hydroxy-3a,5',7,7-tetramethylspiro[1,4,5,6-tetrahydro-2-benzofuran-3,2'-oxolane]-1-yl]propan-2-one

Details

• Internal ID: c7196087-d502-43ed-81f9-138e7095682f
• Taxonomy: Organoheterocyclic compounds > Isobenzofurans
• IUPAC Name: 1-[(1R,3S,3aS,5'S,7aR)-5'-ethenyl-7a-hydroxy-3a,5',7,7-tetramethylspiro[1,4,5,6-tetrahydro-2-benzofuran-3,2'-oxolane]-1-yl]propan-2-one
• SMILES (Canonical): CC(=O)CC1C2(C(CCCC2(C3(O1)CCC(O3)(C)C=C)C)(C)C)O
• SMILES (Isomeric): CC(=O)C[C@@H]1[C@@]2([C@](CCCC2(C)C)([C@]3(O1)CC[C@@](O3)(C)C=C)C)O
• InChI: InChI=1S/C20H32O4/c1-7-17(5)11-12-19(24-17)18(6)10-8-9-16(3,4)20(18,22)15(23-19)13-14(2)21/h7,15,22H,1,8-13H2,2-6H3/t15-,17-,18-,19+,20-/m1/s1
• InChI Key: JZZGZPDAPNARSZ-RACLHMPKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₂O₄
• Molecular Weight: 336.50 g/mol
• Exact Mass: 336.23005950 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 3.76
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9740	97.40%
Caco-2	+	0.6518	65.18%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7096	70.96%
OATP2B1 inhibitior	-	0.8561	85.61%
OATP1B1 inhibitior	+	0.8957	89.57%
OATP1B3 inhibitior	-	0.3167	31.67%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.8103	81.03%
P-glycoprotein inhibitior	-	0.7948	79.48%
P-glycoprotein substrate	-	0.6865	68.65%
CYP3A4 substrate	+	0.6319	63.19%
CYP2C9 substrate	-	0.8114	81.14%
CYP2D6 substrate	-	0.8330	83.30%
CYP3A4 inhibition	-	0.6899	68.99%
CYP2C9 inhibition	-	0.8511	85.11%
CYP2C19 inhibition	-	0.7735	77.35%
CYP2D6 inhibition	-	0.9645	96.45%
CYP1A2 inhibition	-	0.7214	72.14%
CYP2C8 inhibition	-	0.8341	83.41%
CYP inhibitory promiscuity	-	0.9409	94.09%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5878	58.78%
Eye corrosion	-	0.9862	98.62%
Eye irritation	-	0.7388	73.88%
Skin irritation	+	0.5380	53.80%
Skin corrosion	-	0.8782	87.82%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6624	66.24%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	+	0.6023	60.23%
skin sensitisation	-	0.7864	78.64%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.7267	72.67%
Acute Oral Toxicity (c)	III	0.5177	51.77%
Estrogen receptor binding	+	0.7684	76.84%
Androgen receptor binding	+	0.6689	66.89%
Thyroid receptor binding	+	0.6678	66.78%
Glucocorticoid receptor binding	+	0.7204	72.04%
Aromatase binding	+	0.6561	65.61%
PPAR gamma	+	0.5606	56.06%
Honey bee toxicity	-	0.8216	82.16%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9901	99.01%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.60%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.59%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.18%	91.11%
CHEMBL233	P35372	Mu opioid receptor	87.10%	97.93%
CHEMBL218	P21554	Cannabinoid CB1 receptor	87.09%	96.61%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.66%	95.50%
CHEMBL2581	P07339	Cathepsin D	82.37%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	82.23%	91.19%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.12%	100.00%
CHEMBL1951	P21397	Monoamine oxidase A	82.09%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.26%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.53%	85.14%

Plants that contains it

• Haplopappus parvifolius

Cross-Links

• PubChem: 15715636
• LOTUS: LTS0210488
• wikiData: Q105137734