2(6H)-Benzofuranone, 7,7a-dihydro-6-hydroxy-, (6S,7aR)-

Details

• Internal ID: 4b64d7ce-5b35-4a81-a3cf-8440a1629d1d
• Taxonomy: Organoheterocyclic compounds > Benzofurans
• IUPAC Name: (6S,7aR)-6-hydroxy-7,7a-dihydro-6H-1-benzofuran-2-one
• SMILES (Canonical): C1C(C=CC2=CC(=O)OC21)O
• SMILES (Isomeric): C1[C@@H](C=CC2=CC(=O)O[C@@H]21)O
• InChI: InChI=1S/C8H8O3/c9-6-2-1-5-3-8(10)11-7(5)4-6/h1-3,6-7,9H,4H2/t6-,7-/m1/s1
• InChI Key: RAXNUTINVDSFEU-RNFRBKRXSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₈O₃
• Molecular Weight: 152.15 g/mol
• Exact Mass: 152.047344113 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): 0.16
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 67765-59-7
• 2(6H)-Benzofuranone, 7,7a-dihydro-6-hydroxy-, (6S,7aR)-
• CHEBI:81370
• CHEMBL454480
• DTXSID30218030
• AKOS040763330
• C17900
• Q27155307

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.6843	68.43%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.4698	46.98%
OATP2B1 inhibitior	-	0.8653	86.53%
OATP1B1 inhibitior	+	0.9232	92.32%
OATP1B3 inhibitior	+	0.9656	96.56%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9558	95.58%
P-glycoprotein inhibitior	-	0.9878	98.78%
P-glycoprotein substrate	-	0.9443	94.43%
CYP3A4 substrate	-	0.5569	55.69%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8620	86.20%
CYP3A4 inhibition	-	0.9272	92.72%
CYP2C9 inhibition	-	0.9614	96.14%
CYP2C19 inhibition	-	0.8926	89.26%
CYP2D6 inhibition	-	0.9438	94.38%
CYP1A2 inhibition	-	0.8016	80.16%
CYP2C8 inhibition	-	0.9675	96.75%
CYP inhibitory promiscuity	-	0.9001	90.01%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9419	94.19%
Carcinogenicity (trinary)	Non-required	0.4629	46.29%
Eye corrosion	+	0.4723	47.23%
Eye irritation	+	0.9389	93.89%
Skin irritation	+	0.6297	62.97%
Skin corrosion	-	0.8917	89.17%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7418	74.18%
Micronuclear	+	0.5218	52.18%
Hepatotoxicity	+	0.6427	64.27%
skin sensitisation	-	0.5529	55.29%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.5575	55.75%
Acute Oral Toxicity (c)	III	0.4920	49.20%
Estrogen receptor binding	-	0.8774	87.74%
Androgen receptor binding	-	0.7668	76.68%
Thyroid receptor binding	-	0.7948	79.48%
Glucocorticoid receptor binding	-	0.6717	67.17%
Aromatase binding	-	0.8639	86.39%
PPAR gamma	-	0.7449	74.49%
Honey bee toxicity	-	0.8756	87.56%
Biodegradation	+	0.5750	57.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	-	0.4690	46.90%

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	95.35%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.70%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.50%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.24%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.80%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.47%	100.00%

Plants that contains it

• Campylospermum reticulatum
• Cocculus laurifolius
• Phyllanthus angkorensis
• Phyllanthus anisolobus
• Phyllanthus klotzschianus
• Sinomenium acutum

Cross-Links

• PubChem: 155054
• LOTUS: LTS0018983
• wikiData: Q27155307