Spirobenzofuran

Details

• Internal ID: 569f3cc0-5eca-458e-ac12-2117b9b176f8
• Taxonomy: Organoheterocyclic compounds > Benzofurans
• IUPAC Name: 2,5-dihydroxy-4',4',6-trimethylspiro[2H-1-benzofuran-3,3'-cyclopentane]-1'-one
• SMILES (Canonical): CC1=CC2=C(C=C1O)C3(CC(=O)CC3(C)C)C(O2)O
• SMILES (Isomeric): CC1=CC2=C(C=C1O)C3(CC(=O)CC3(C)C)C(O2)O
• InChI: InChI=1S/C15H18O4/c1-8-4-12-10(5-11(8)17)15(13(18)19-12)7-9(16)6-14(15,2)3/h4-5,13,17-18H,6-7H2,1-3H3
• InChI Key: GASOCDUVJSYZGK-UHFFFAOYSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₄
• Molecular Weight: 262.30 g/mol
• Exact Mass: 262.12050905 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 2.04
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• 2,5-dihydroxy-4',4',6-trimethylspiro[2H-1-benzofuran-3,3'-cyclopentane]-1'-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9892	98.92%
Caco-2	+	0.7807	78.07%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7925	79.25%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9078	90.78%
OATP1B3 inhibitior	+	0.9192	91.92%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8913	89.13%
P-glycoprotein inhibitior	-	0.9753	97.53%
P-glycoprotein substrate	-	0.8822	88.22%
CYP3A4 substrate	+	0.5505	55.05%
CYP2C9 substrate	-	0.5628	56.28%
CYP2D6 substrate	-	0.7468	74.68%
CYP3A4 inhibition	-	0.5871	58.71%
CYP2C9 inhibition	-	0.7445	74.45%
CYP2C19 inhibition	-	0.7978	79.78%
CYP2D6 inhibition	-	0.9117	91.17%
CYP1A2 inhibition	+	0.7155	71.55%
CYP2C8 inhibition	-	0.9058	90.58%
CYP inhibitory promiscuity	-	0.8122	81.22%
UGT catelyzed	+	0.7362	73.62%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.5557	55.57%
Eye corrosion	-	0.9868	98.68%
Eye irritation	+	0.7797	77.97%
Skin irritation	-	0.6239	62.39%
Skin corrosion	-	0.8887	88.87%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6764	67.64%
Micronuclear	-	0.7341	73.41%
Hepatotoxicity	-	0.5823	58.23%
skin sensitisation	-	0.7718	77.18%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.5982	59.82%
Acute Oral Toxicity (c)	III	0.6013	60.13%
Estrogen receptor binding	-	0.6111	61.11%
Androgen receptor binding	+	0.5633	56.33%
Thyroid receptor binding	+	0.5359	53.59%
Glucocorticoid receptor binding	-	0.6710	67.10%
Aromatase binding	-	0.6117	61.17%
PPAR gamma	+	0.6349	63.49%
Honey bee toxicity	-	0.9288	92.88%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9941	99.41%

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	94.72%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.54%	95.56%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	93.46%	93.40%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.13%	89.00%
CHEMBL1913	P09619	Platelet-derived growth factor receptor beta	88.05%	95.70%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.36%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.57%	100.00%
CHEMBL2581	P07339	Cathepsin D	84.24%	98.95%
CHEMBL4208	P20618	Proteasome component C5	83.53%	90.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.60%	99.15%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.28%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.86%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	80.53%	94.73%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.35%	91.07%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 10061243
• LOTUS: LTS0148029
• wikiData: Q77515133