(3R,3aR,6S)-3-(furan-2-yl)-6-hydroxy-3a,7-dimethyl-3,4,5,6-tetrahydro-2-benzofuran-1-one

Details

• Internal ID: 77af0127-6bef-4e83-8d4e-4eb245c088d1
• Taxonomy: Organoheterocyclic compounds > Isobenzofurans
• IUPAC Name: (3R,3aR,6S)-3-(furan-2-yl)-6-hydroxy-3a,7-dimethyl-3,4,5,6-tetrahydro-2-benzofuran-1-one
• SMILES (Canonical): CC1=C2C(=O)OC(C2(CCC1O)C)C3=CC=CO3
• SMILES (Isomeric): CC1=C2C(=O)O[C@H]([C@@]2(CC[C@@H]1O)C)C3=CC=CO3
• InChI: InChI=1S/C14H16O4/c1-8-9(15)5-6-14(2)11(8)13(16)18-12(14)10-4-3-7-17-10/h3-4,7,9,12,15H,5-6H2,1-2H3/t9-,12-,14+/m0/s1
• InChI Key: NXIVBEINPTVKFF-DUFXMDAXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₆O₄
• Molecular Weight: 248.27 g/mol
• Exact Mass: 248.10485899 g/mol
• Topological Polar Surface Area (TPSA): 59.70 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 2.36
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9960	99.60%
Caco-2	+	0.6609	66.09%
Blood Brain Barrier	+	0.5605	56.05%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7727	77.27%
OATP2B1 inhibitior	-	0.8593	85.93%
OATP1B1 inhibitior	+	0.9032	90.32%
OATP1B3 inhibitior	+	0.9101	91.01%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.9473	94.73%
P-glycoprotein inhibitior	-	0.9331	93.31%
P-glycoprotein substrate	-	0.9153	91.53%
CYP3A4 substrate	+	0.5790	57.90%
CYP2C9 substrate	-	0.8046	80.46%
CYP2D6 substrate	-	0.8567	85.67%
CYP3A4 inhibition	-	0.5912	59.12%
CYP2C9 inhibition	-	0.8668	86.68%
CYP2C19 inhibition	-	0.8865	88.65%
CYP2D6 inhibition	-	0.8948	89.48%
CYP1A2 inhibition	-	0.6299	62.99%
CYP2C8 inhibition	-	0.8870	88.70%
CYP inhibitory promiscuity	-	0.8798	87.98%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.3983	39.83%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.8846	88.46%
Skin irritation	-	0.5171	51.71%
Skin corrosion	-	0.8320	83.20%
Ames mutagenesis	-	0.6470	64.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.6577	65.77%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	+	0.5805	58.05%
skin sensitisation	-	0.7638	76.38%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.5970	59.70%
Acute Oral Toxicity (c)	III	0.4180	41.80%
Estrogen receptor binding	-	0.7110	71.10%
Androgen receptor binding	-	0.6104	61.04%
Thyroid receptor binding	-	0.7062	70.62%
Glucocorticoid receptor binding	-	0.6714	67.14%
Aromatase binding	-	0.5904	59.04%
PPAR gamma	+	0.5606	56.06%
Honey bee toxicity	-	0.9446	94.46%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9617	96.17%

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	94.43%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.04%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.93%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.44%	89.00%
CHEMBL2581	P07339	Cathepsin D	85.32%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.84%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.01%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.42%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.10%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.05%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.63%	100.00%

Plants that contains it

• Dictamnus dasycarpus

Cross-Links

• PubChem: 162985620
• LOTUS: LTS0238811
• wikiData: Q105187201