(2S)-3-[(2S,3S)-5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxo-2,3-dihydrochromen-3-yl]-5,7-dihydroxy-2-(4-methoxyphenyl)-2,3-dihydrochromen-4-one

Details

• Internal ID: 1de9097a-4353-481e-a3a6-6a3d24a28535
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Biflavonoids and polyflavonoids
• IUPAC Name: (2S)-3-[(2S,3S)-5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxo-2,3-dihydrochromen-3-yl]-5,7-dihydroxy-2-(4-methoxyphenyl)-2,3-dihydrochromen-4-one
• SMILES (Canonical): COC1=CC=C(C=C1)C2C(C(=O)C3=C(C=C(C=C3O2)O)O)C4C(OC5=CC(=CC(=C5C4=O)O)O)C6=CC=C(C=C6)OC
• SMILES (Isomeric): COC1=CC=C(C=C1)[C@@H]2[C@@H](C(=O)C3=C(C=C(C=C3O2)O)O)C4[C@H](OC5=CC(=CC(=C5C4=O)O)O)C6=CC=C(C=C6)OC
• InChI: InChI=1S/C32H26O10/c1-39-19-7-3-15(4-8-19)31-27(29(37)25-21(35)11-17(33)13-23(25)41-31)28-30(38)26-22(36)12-18(34)14-24(26)42-32(28)16-5-9-20(40-2)10-6-16/h3-14,27-28,31-36H,1-2H3/t27-,28?,31-,32-/m1/s1
• InChI Key: BTCICADMSGBCKA-VGVWILAUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₂₆O₁₀
• Molecular Weight: 570.50 g/mol
• Exact Mass: 570.15259702 g/mol
• Topological Polar Surface Area (TPSA): 152.00 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 5.09
• H-Bond Acceptor: 10
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

• (2S)-3-[(2S,3S)-5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxo-2,3-dihydrochromen-3-yl]-5,7-dihydroxy-2-(4-methoxyphenyl)-2,3-dihydrochromen-4-one
• SMR000445710
• CHEMBL1545093
• BDBM58173
• cid_16745525
• (2S)-2-(4-methoxyphenyl)-3-[(2S,3S)-2-(4-methoxyphenyl)-5,7-bis(oxidanyl)-4-oxidanylidene-2,3-dihydrochromen-3-yl]-5,7-bis(oxidanyl)-2,3-dihydrochromen-4-one
• (2S)-3-[(2S,3S)-5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl]-5,7-dihydroxy-2-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
• (2S)-3-[(2S,3S)-5,7-dihydroxy-4-keto-2-(4-methoxyphenyl)chroman-3-yl]-5,7-dihydroxy-2-(4-methoxyphenyl)chroman-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9325	93.25%
Caco-2	-	0.8093	80.93%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8148	81.48%
OATP2B1 inhibitior	-	0.5771	57.71%
OATP1B1 inhibitior	+	0.8925	89.25%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7559	75.59%
P-glycoprotein inhibitior	+	0.7719	77.19%
P-glycoprotein substrate	-	0.9618	96.18%
CYP3A4 substrate	+	0.5350	53.50%
CYP2C9 substrate	-	0.8060	80.60%
CYP2D6 substrate	-	0.7896	78.96%
CYP3A4 inhibition	+	0.5831	58.31%
CYP2C9 inhibition	+	0.6590	65.90%
CYP2C19 inhibition	+	0.6234	62.34%
CYP2D6 inhibition	-	0.7411	74.11%
CYP1A2 inhibition	+	0.6533	65.33%
CYP2C8 inhibition	-	0.6806	68.06%
CYP inhibitory promiscuity	+	0.6726	67.26%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6328	63.28%
Eye corrosion	-	0.9860	98.60%
Eye irritation	-	0.7463	74.63%
Skin irritation	-	0.7256	72.56%
Skin corrosion	-	0.9363	93.63%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6837	68.37%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	-	0.5591	55.91%
skin sensitisation	-	0.9458	94.58%
Respiratory toxicity	-	0.6778	67.78%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.7602	76.02%
Acute Oral Toxicity (c)	III	0.6505	65.05%
Estrogen receptor binding	+	0.8446	84.46%
Androgen receptor binding	+	0.7908	79.08%
Thyroid receptor binding	+	0.6157	61.57%
Glucocorticoid receptor binding	+	0.6872	68.72%
Aromatase binding	-	0.6783	67.83%
PPAR gamma	+	0.7207	72.07%
Honey bee toxicity	-	0.9094	90.94%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9066	90.66%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293237	P54132	Bloom syndrome protein	15848.9 nM	Potency	via CMAUP
CHEMBL5514	P42858	Huntingtin	1122 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	17782.8 nM; 11220.2 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.88%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.33%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.90%	99.15%
CHEMBL4208	P20618	Proteasome component C5	91.41%	90.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.39%	96.09%
CHEMBL240	Q12809	HERG	91.37%	89.76%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.69%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.88%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.34%	97.09%
CHEMBL1929	P47989	Xanthine dehydrogenase	87.55%	96.12%
CHEMBL2535	P11166	Glucose transporter	87.43%	98.75%
CHEMBL3401	O75469	Pregnane X receptor	85.66%	94.73%
CHEMBL2581	P07339	Cathepsin D	85.65%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.99%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.58%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.56%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	82.43%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.91%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.34%	85.14%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.12%	93.99%

Plants that contains it

• Stellera chamaejasme
• Wikstroemia sikokiana

Cross-Links

• PubChem: 16745525
• NPASS: NPC287789
• ChEMBL: CHEMBL1545093
• LOTUS: LTS0238894
• wikiData: Q105101541