2-[(6S,6aR,10aR)-1-hydroxy-3-(6-hydroxy-1-benzofuran-2-yl)-7,7,9-trimethyl-6,6a,8,10a-tetrahydrobenzo[c]chromen-6-yl]-5-(6-hydroxy-1-benzofuran-2-yl)benzene-1,3-diol

Details

• Internal ID: 41e94e0e-dacf-4913-b461-a36b39a1e788
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: 2-[(6S,6aR,10aR)-1-hydroxy-3-(6-hydroxy-1-benzofuran-2-yl)-7,7,9-trimethyl-6,6a,8,10a-tetrahydrobenzo[c]chromen-6-yl]-5-(6-hydroxy-1-benzofuran-2-yl)benzene-1,3-diol
• SMILES (Canonical): CC1=CC2C(C(OC3=CC(=CC(=C23)O)C4=CC5=C(O4)C=C(C=C5)O)C6=C(C=C(C=C6O)C7=CC8=C(O7)C=C(C=C8)O)O)C(C1)(C)C
• SMILES (Isomeric): CC1=C[C@@H]2[C@@H]([C@H](OC3=CC(=CC(=C23)O)C4=CC5=C(O4)C=C(C=C5)O)C6=C(C=C(C=C6O)C7=CC8=C(O7)C=C(C=C8)O)O)C(C1)(C)C
• InChI: InChI=1S/C38H32O8/c1-18-8-25-34-26(41)11-22(30-13-20-5-7-24(40)16-32(20)45-30)14-33(34)46-37(36(25)38(2,3)17-18)35-27(42)9-21(10-28(35)43)29-12-19-4-6-23(39)15-31(19)44-29/h4-16,25,36-37,39-43H,17H2,1-3H3/t25-,36-,37+/m0/s1
• InChI Key: GKHRLTCUMXVTAV-YRVPZNQBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₃₂O₈
• Molecular Weight: 616.70 g/mol
• Exact Mass: 616.20971797 g/mol
• Topological Polar Surface Area (TPSA): 137.00 Ų
• XlogP: 7.80
• Atomic LogP (AlogP): 9.25
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

• 5-(6-Hydroxy-2-benzofuranyl)-2-[(6S,6aR,10aR)-6a,7,8,10a-tetrahydro-1-hydroxy-3-(6-hydroxy-2-benzofuranyl)-7,7,9-trimethyl-6H-dibenzo[b,d]pyran-6-yl]-1,3-benzenediol
• 84323-11-5

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9854	98.54%
Caco-2	-	0.8478	84.78%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6893	68.93%
OATP2B1 inhibitior	+	0.7190	71.90%
OATP1B1 inhibitior	+	0.8027	80.27%
OATP1B3 inhibitior	+	0.9438	94.38%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.8485	84.85%
P-glycoprotein inhibitior	+	0.8070	80.70%
P-glycoprotein substrate	+	0.5668	56.68%
CYP3A4 substrate	+	0.6508	65.08%
CYP2C9 substrate	-	0.8135	81.35%
CYP2D6 substrate	+	0.3822	38.22%
CYP3A4 inhibition	+	0.6448	64.48%
CYP2C9 inhibition	+	0.9007	90.07%
CYP2C19 inhibition	+	0.7888	78.88%
CYP2D6 inhibition	-	0.8380	83.80%
CYP1A2 inhibition	+	0.6860	68.60%
CYP2C8 inhibition	+	0.7888	78.88%
CYP inhibitory promiscuity	+	0.9512	95.12%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Danger	0.4615	46.15%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.8577	85.77%
Skin irritation	-	0.7449	74.49%
Skin corrosion	-	0.9230	92.30%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7792	77.92%
Micronuclear	+	0.6100	61.00%
Hepatotoxicity	-	0.6958	69.58%
skin sensitisation	-	0.7492	74.92%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.7283	72.83%
Acute Oral Toxicity (c)	III	0.5348	53.48%
Estrogen receptor binding	+	0.8349	83.49%
Androgen receptor binding	+	0.8112	81.12%
Thyroid receptor binding	+	0.6795	67.95%
Glucocorticoid receptor binding	+	0.8346	83.46%
Aromatase binding	+	0.6025	60.25%
PPAR gamma	+	0.8014	80.14%
Honey bee toxicity	-	0.8362	83.62%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9924	99.24%

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	98.07%	91.11%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	95.38%	93.40%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.05%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.30%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.22%	89.00%
CHEMBL2581	P07339	Cathepsin D	88.95%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.79%	99.23%
CHEMBL2996	Q05655	Protein kinase C delta	87.74%	97.79%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.55%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.96%	95.56%
CHEMBL4208	P20618	Proteasome component C5	84.33%	90.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.33%	99.15%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	84.32%	85.11%
CHEMBL3038469	P24941	CDK2/Cyclin A	83.59%	91.38%
CHEMBL3227	P41594	Metabotropic glutamate receptor 5	83.46%	96.42%
CHEMBL242	Q92731	Estrogen receptor beta	82.10%	98.35%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	81.01%	85.49%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.00%	92.94%

Plants that contains it

• Morus alba

Cross-Links

• PubChem: 102150173
• NPASS: NPC198026