6-[5-(5,7-Dihydroxy-4-oxo-chromen-2-yl)-2-methoxy-phenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one

Details

• Internal ID: c5d1065b-0547-4fc6-addf-d47be73e444a
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Biflavonoids and polyflavonoids
• IUPAC Name: 6-[5-(5,7-dihydroxy-4-oxochromen-2-yl)-2-methoxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• SMILES (Canonical): COC1=C(C=C(C=C1)C2=CC(=O)C3=C(C=C(C=C3O2)O)O)C4=C(C5=C(C=C4O)OC(=CC5=O)C6=CC=C(C=C6)O)O
• SMILES (Isomeric): COC1=C(C=C(C=C1)C2=CC(=O)C3=C(C=C(C=C3O2)O)O)C4=C(C5=C(C=C4O)OC(=CC5=O)C6=CC=C(C=C6)O)O
• InChI: InChI=1S/C31H20O10/c1-39-23-7-4-15(25-11-21(36)29-19(34)9-17(33)10-26(29)41-25)8-18(23)28-20(35)13-27-30(31(28)38)22(37)12-24(40-27)14-2-5-16(32)6-3-14/h2-13,32-35,38H,1H3
• InChI Key: ZBOKFHZIWKIWRZ-UHFFFAOYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₂₀O₁₀
• Molecular Weight: 552.50 g/mol
• Exact Mass: 552.10564683 g/mol
• Topological Polar Surface Area (TPSA): 163.00 Ų
• XlogP: 5.40
• Atomic LogP (AlogP): 5.44
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

• robustaflavone-4'-methyl ether
• Robustaflavone-4''''-Methyl Ether
• BDBM50457775
• 4''',5,5'',7,7''-Pentahydroxy-4'-methoxy-3',6''-biflavone
• 6-[5-(5,7-Dihydroxy-4-oxo-4H-chromen-2-yl)-2-methoxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
• 6-[5-(5,7-dihydroxy-4-oxo-chromen-2-yl)-2-methoxy-phenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9430	94.30%
Caco-2	-	0.8131	81.31%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.8174	81.74%
OATP2B1 inhibitior	-	0.5602	56.02%
OATP1B1 inhibitior	-	0.3358	33.58%
OATP1B3 inhibitior	+	0.9706	97.06%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8040	80.40%
P-glycoprotein inhibitior	+	0.7536	75.36%
P-glycoprotein substrate	-	0.5957	59.57%
CYP3A4 substrate	+	0.6413	64.13%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	+	0.5760	57.60%
CYP2C9 inhibition	+	0.7647	76.47%
CYP2C19 inhibition	+	0.7471	74.71%
CYP2D6 inhibition	-	0.7766	77.66%
CYP1A2 inhibition	+	0.8002	80.02%
CYP2C8 inhibition	+	0.9252	92.52%
CYP inhibitory promiscuity	+	0.6806	68.06%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5868	58.68%
Eye corrosion	-	0.9861	98.61%
Eye irritation	-	0.8111	81.11%
Skin irritation	-	0.6647	66.47%
Skin corrosion	-	0.9266	92.66%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6931	69.31%
Micronuclear	+	0.8900	89.00%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.9499	94.99%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.6376	63.76%
Acute Oral Toxicity (c)	III	0.6544	65.44%
Estrogen receptor binding	+	0.9067	90.67%
Androgen receptor binding	+	0.9325	93.25%
Thyroid receptor binding	+	0.6161	61.61%
Glucocorticoid receptor binding	+	0.8914	89.14%
Aromatase binding	+	0.5411	54.11%
PPAR gamma	+	0.7828	78.28%
Honey bee toxicity	-	0.7172	71.72%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5849	58.49%
Fish aquatic toxicity	+	0.8837	88.37%

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	98.47%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.28%	94.00%
CHEMBL3194	P02766	Transthyretin	97.24%	90.71%
CHEMBL2581	P07339	Cathepsin D	96.41%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.19%	89.00%
CHEMBL242	Q92731	Estrogen receptor beta	95.11%	98.35%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	92.89%	95.64%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.14%	86.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	92.04%	96.21%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.54%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.19%	95.56%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	90.61%	95.78%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.06%	85.14%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.05%	90.71%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	84.05%	83.57%
CHEMBL2002	P12268	Inosine-5'-monophosphate dehydrogenase 2	83.61%	98.21%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.90%	99.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.75%	99.17%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.28%	91.71%
CHEMBL1255126	O15151	Protein Mdm4	82.20%	90.20%
CHEMBL4208	P20618	Proteasome component C5	82.16%	90.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.05%	97.28%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.34%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	80.43%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.40%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.12%	95.89%

Plants that contains it

• Selaginella delicatula
• Selaginella doederleinii
• Selaginella labordei

Cross-Links

• PubChem: 11757331
• NPASS: NPC72425
• LOTUS: LTS0009845
• wikiData: Q104400018