(3S)-3beta-Phenyl-3abeta-(1,3-benzodioxol-5-yl)-6,8-dimethoxy-8bbeta-hydroxy-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-1-one

Details

• Internal ID: 500638e7-653a-4713-a9d7-7065b1dc9767
• Taxonomy: Organoheterocyclic compounds > Benzofurans > Flavaglines
• IUPAC Name: (3S,3aR,8bR)-3a-(1,3-benzodioxol-5-yl)-8b-hydroxy-6,8-dimethoxy-3-phenyl-2,3-dihydrocyclopenta[b][1]benzofuran-1-one
• SMILES (Canonical): COC1=CC2=C(C(=C1)OC)C3(C(=O)CC(C3(O2)C4=CC5=C(C=C4)OCO5)C6=CC=CC=C6)O
• SMILES (Isomeric): COC1=CC2=C(C(=C1)OC)[C@@]3(C(=O)C[C@H]([C@@]3(O2)C4=CC5=C(C=C4)OCO5)C6=CC=CC=C6)O
• InChI: InChI=1S/C26H22O7/c1-29-17-11-21(30-2)24-22(12-17)33-26(16-8-9-19-20(10-16)32-14-31-19)18(13-23(27)25(24,26)28)15-6-4-3-5-7-15/h3-12,18,28H,13-14H2,1-2H3/t18-,25+,26-/m0/s1
• InChI Key: YCRUGMHLZHDDGT-IMDCKVJKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₂O₇
• Molecular Weight: 446.40 g/mol
• Exact Mass: 446.13655304 g/mol
• Topological Polar Surface Area (TPSA): 83.40 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.66
• H-Bond Acceptor: 7
• 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	+	0.9802	98.02%
Caco-2	+	0.5116	51.16%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8195	81.95%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8950	89.50%
OATP1B3 inhibitior	+	0.9370	93.70%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9138	91.38%
P-glycoprotein inhibitior	+	0.8855	88.55%
P-glycoprotein substrate	-	0.7842	78.42%
CYP3A4 substrate	+	0.6212	62.12%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6814	68.14%
CYP3A4 inhibition	+	0.8521	85.21%
CYP2C9 inhibition	+	0.7685	76.85%
CYP2C19 inhibition	+	0.6541	65.41%
CYP2D6 inhibition	-	0.7578	75.78%
CYP1A2 inhibition	-	0.8828	88.28%
CYP2C8 inhibition	+	0.4743	47.43%
CYP inhibitory promiscuity	+	0.6162	61.62%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.3954	39.54%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.8672	86.72%
Skin irritation	-	0.7914	79.14%
Skin corrosion	-	0.9490	94.90%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3972	39.72%
Micronuclear	+	0.8033	80.33%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.8219	82.19%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.7155	71.55%
Acute Oral Toxicity (c)	III	0.4609	46.09%
Estrogen receptor binding	+	0.8262	82.62%
Androgen receptor binding	+	0.8224	82.24%
Thyroid receptor binding	+	0.7122	71.22%
Glucocorticoid receptor binding	+	0.8295	82.95%
Aromatase binding	-	0.5140	51.40%
PPAR gamma	+	0.7131	71.31%
Honey bee toxicity	-	0.8575	85.75%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.9316	93.16%

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	98.31%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.83%	95.56%
CHEMBL240	Q12809	HERG	95.52%	89.76%
CHEMBL2581	P07339	Cathepsin D	93.76%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.50%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.12%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.69%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.68%	99.23%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	92.41%	92.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.24%	86.33%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	92.13%	94.80%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.13%	96.77%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.06%	93.99%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.01%	97.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.62%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.23%	95.89%
CHEMBL4208	P20618	Proteasome component C5	84.67%	90.00%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	84.55%	89.44%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.24%	96.00%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	83.18%	94.03%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.02%	94.45%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.59%	95.50%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.34%	99.15%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	80.05%	96.09%

Plants that contains it

• Aglaia elliptica

Cross-Links

• PubChem: 9889764
• LOTUS: LTS0042491
• wikiData: Q105346443