Robustaflavone

Details

• Internal ID: 75edd7da-486d-4014-9c8e-a3b16b126bdb
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Biflavonoids and polyflavonoids
• IUPAC Name: 6-[5-(5,7-dihydroxy-4-oxochromen-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• SMILES (Canonical): C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C=C(C(=C3O)C4=C(C=CC(=C4)C5=CC(=O)C6=C(C=C(C=C6O5)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C=C(C(=C3O)C4=C(C=CC(=C4)C5=CC(=O)C6=C(C=C(C=C6O5)O)O)O)O)O
• InChI: InChI=1S/C30H18O10/c31-15-4-1-13(2-5-15)23-11-22(37)29-26(39-23)12-20(35)27(30(29)38)17-7-14(3-6-18(17)33)24-10-21(36)28-19(34)8-16(32)9-25(28)40-24/h1-12,31-35,38H
• InChI Key: BORWSEZUWHQTOK-UHFFFAOYSA-N
• Popularity: 69 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₁₈O₁₀
• Molecular Weight: 538.50 g/mol
• Exact Mass: 538.08999677 g/mol
• Topological Polar Surface Area (TPSA): 174.00 Ų
• XlogP: 5.00
• Atomic LogP (AlogP): 5.13
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 3

Synonyms

• 49620-13-5
• 3',6''-Biapigenin
• CHEBI:8881
• 6-(5-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenyl)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
• 6-[5-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
• SCHEMBL561807
• DTXSID30197937
• BORWSEZUWHQTOK-UHFFFAOYSA-N
• LMPK12040005
• AKOS040747412
• 6-[5-(5,7-dihydroxy-4-oxochromen-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• FT-0776777
• Q27089374
• 4H-1-Benzopyran-4-one, 6-(5-(5,7-dihydroxy-4-oxo-4H-1-benzopyran-2-yl)-2-hydroxyphenyl)-5,7-dihydroxy-2-(4-hydroxyphenyl)
• 4H-1-Benzopyran-4-one, 6-[5-(5,7-dihydroxy-4-oxo-4H-1-benzopyran-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl-
• 6-(5-(5,7-dihydroxy-4-oxo-4H-1-benzopyran-2-yl)-2-hydroxyphenyl)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
• 6-[5-(5,7-Dihydroxy-4-oxo-chromen-2-yl)-2-hydroxy-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	+	0.9336	93.36%
Caco-2	-	0.8764	87.64%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8010	80.10%
OATP2B1 inhibitior	+	0.5795	57.95%
OATP1B1 inhibitior	+	0.8224	82.24%
OATP1B3 inhibitior	-	0.2208	22.08%
MATE1 inhibitior	+	0.6600	66.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7448	74.48%
P-glycoprotein inhibitior	+	0.5969	59.69%
P-glycoprotein substrate	-	0.7787	77.87%
CYP3A4 substrate	+	0.5938	59.38%
CYP2C9 substrate	-	0.6443	64.43%
CYP2D6 substrate	-	0.8503	85.03%
CYP3A4 inhibition	+	0.6172	61.72%
CYP2C9 inhibition	+	0.8920	89.20%
CYP2C19 inhibition	+	0.6827	68.27%
CYP2D6 inhibition	-	0.9322	93.22%
CYP1A2 inhibition	+	0.6838	68.38%
CYP2C8 inhibition	+	0.9010	90.10%
CYP inhibitory promiscuity	+	0.5157	51.57%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7320	73.20%
Eye corrosion	-	0.9929	99.29%
Eye irritation	-	0.7218	72.18%
Skin irritation	+	0.5256	52.56%
Skin corrosion	-	0.9525	95.25%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3712	37.12%
Micronuclear	+	0.9200	92.00%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.8881	88.81%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.7138	71.38%
Acute Oral Toxicity (c)	II	0.6295	62.95%
Estrogen receptor binding	+	0.8526	85.26%
Androgen receptor binding	+	0.9299	92.99%
Thyroid receptor binding	+	0.5838	58.38%
Glucocorticoid receptor binding	+	0.8565	85.65%
Aromatase binding	+	0.5598	55.98%
PPAR gamma	+	0.8419	84.19%
Honey bee toxicity	-	0.7491	74.91%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9283	92.83%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	6200 nM	IC50	PMID: 25907369

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.22%	91.11%
CHEMBL242	Q92731	Estrogen receptor beta	98.81%	98.35%
CHEMBL3194	P02766	Transthyretin	97.44%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.78%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	96.16%	99.15%
CHEMBL2581	P07339	Cathepsin D	95.42%	98.95%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	93.14%	95.64%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.84%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	91.97%	91.49%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	91.21%	83.57%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	88.70%	96.21%
CHEMBL1978	P11511	Cytochrome P450 19A1	88.61%	91.76%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	88.55%	91.71%
CHEMBL1929	P47989	Xanthine dehydrogenase	88.14%	96.12%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.76%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.69%	90.71%
CHEMBL2208	P49137	MAP kinase-activated protein kinase 2	85.37%	95.20%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	84.70%	98.11%
CHEMBL3038469	P24941	CDK2/Cyclin A	84.68%	91.38%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	84.43%	89.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.31%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.04%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	83.27%	94.73%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	83.12%	85.11%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.63%	95.78%
CHEMBL4530	P00488	Coagulation factor XIII	81.36%	96.00%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	81.26%	83.10%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.62%	97.28%

Plants that contains it

• Aronia arbutifolia
• Clibadium sodiroi
• Cupressus nootkatensis
• Dacrycarpus imbricatus
• Discaria serratifolia
• Garcinia multiflora
• Luxemburgia nobilis
• Pteris dactylina
• Pyrostegia venusta
• Rostellularia hayatae
• Schinus terebinthifolia
• Selaginella delicatula
• Selaginella denticulata
• Selaginella labordei
• Selaginella lepidophylla
• Selaginella nothohybrida
• Selaginella pulvinata
• Selaginella selaginoides
• Selaginella sinensis
• Selaginella tamariscina
• Selaginella willdenowii
• Silene viscaria
• Toxicodendron succedaneum

Cross-Links

• PubChem: 5281694
• NPASS: NPC111112
• ChEMBL: CHEMBL63677
• LOTUS: LTS0213241
• wikiData: Q27089374