Podocarpusflavone A

Details

• Internal ID: 4dffead5-c671-4698-8ddb-4b60870e14da
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Biflavonoids and polyflavonoids
• IUPAC Name: 8-[5-(5,7-dihydroxy-4-oxochromen-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one
• SMILES (Canonical): COC1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)C4=C(C=CC(=C4)C5=CC(=O)C6=C(C=C(C=C6O5)O)O)O
• SMILES (Isomeric): COC1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)C4=C(C=CC(=C4)C5=CC(=O)C6=C(C=C(C=C6O5)O)O)O
• InChI: InChI=1S/C31H20O10/c1-39-17-5-2-14(3-6-17)25-13-24(38)30-22(36)11-21(35)28(31(30)41-25)18-8-15(4-7-19(18)33)26-12-23(37)29-20(34)9-16(32)10-27(29)40-26/h2-13,32-36H,1H3
• InChI Key: RBTRUVNXLDXHBJ-UHFFFAOYSA-N
• Popularity: 13 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

• 22136-74-9
• Podocarpusflavonea
• 41583-83-9
• Mono-O-methylamentoflavone
• 8-[5-(5,7-dihydroxy-4-oxochromen-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one
• 8-(5-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenyl)-5,7-dihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one
• 8-[5-(5,7-dihydroxy-4-oxo-chromen-2-yl)-2-hydroxy-phenyl]-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one
• 4H-1-Benzopyran-4-one, 8-(5-(5,7-dihydroxy-4-oxo-4H-1-benzopyran-2-yl)-2-hydroxyphenyl)-5,7-dihydroxy-2-(4-hydroxyphenyl)-, monomethyl ether
• 8-[5-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one
• DTXSID10944784
• CHEBI:191156
• HY-N2198
• AKOS032962454
• CS-5764
• MS-30092
• E80809
• 4H-1-Benzopyran-4-one, 8-(5-(5,7-dihydroxy-4-oxo-4H-1-benzopyran-2-yl)-2-hydroxyphenyl)-5,7-dihydroxy-2-(4-methoxyphenyl)-
• 8-[5-(5,7-Dihydroxy-4-oxo-4H-1-benzopyran-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9430	94.30%
Caco-2	-	0.8394	83.94%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8174	81.74%
OATP2B1 inhibitior	+	0.5771	57.71%
OATP1B1 inhibitior	-	0.4881	48.81%
OATP1B3 inhibitior	+	0.9706	97.06%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8852	88.52%
P-glycoprotein inhibitior	+	0.6939	69.39%
P-glycoprotein substrate	-	0.7051	70.51%
CYP3A4 substrate	+	0.6419	64.19%
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	+	0.8607	86.07%
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	-	0.8183	81.83%
Skin irritation	-	0.6647	66.47%
Skin corrosion	-	0.9266	92.66%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4083	40.83%
Micronuclear	+	0.8900	89.00%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.9499	94.99%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.6230	62.30%
Acute Oral Toxicity (c)	III	0.6544	65.44%
Estrogen receptor binding	+	0.8786	87.86%
Androgen receptor binding	+	0.9544	95.44%
Thyroid receptor binding	+	0.6457	64.57%
Glucocorticoid receptor binding	+	0.8190	81.90%
Aromatase binding	-	0.4901	49.01%
PPAR gamma	+	0.7698	76.98%
Honey bee toxicity	-	0.7797	77.97%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.8837	88.37%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4822	P56817	Beta-secretase 1	990 nM	IC50	PMID: 20598535

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.83%	91.11%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	98.19%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.83%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	96.60%	91.49%
CHEMBL2581	P07339	Cathepsin D	95.80%	98.95%
CHEMBL242	Q92731	Estrogen receptor beta	95.60%	98.35%
CHEMBL3194	P02766	Transthyretin	95.28%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.65%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.87%	89.00%
CHEMBL308	P06493	Cyclin-dependent kinase 1	93.40%	91.73%
CHEMBL4208	P20618	Proteasome component C5	91.20%	90.00%
CHEMBL1907	P15144	Aminopeptidase N	91.06%	93.31%
CHEMBL1929	P47989	Xanthine dehydrogenase	89.75%	96.12%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.51%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.33%	86.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	88.13%	96.21%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.44%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	85.12%	94.73%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	84.33%	93.65%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.01%	99.17%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	82.32%	89.23%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.88%	91.71%
CHEMBL3192	Q9BY41	Histone deacetylase 8	81.27%	93.99%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.99%	95.50%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.53%	90.71%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.51%	97.28%
CHEMBL6029	Q9BQI3	Eukaryotic translation initiation factor 2-alpha kinase 1	80.24%	88.67%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.17%	94.45%

Plants that contains it

• Afrocarpus gracilior
• Aglaia forbesii
• Cupressus sempervirens
• Cycas revoluta
• Dacrycarpus imbricatus
• Dendrobium chrysotoxum
• Eurybia divaricata
• Garcinia dulcis
• Garcinia intermedia
• Garcinia subelliptica
• Ginkgo biloba
• Hydnocarpus hainanensis
• Isophysis tasmanica
• Juniperus sabina var. sabina
• Leycesteria formosa
• Manihot esculenta
• Ouratea multiflora
• Pinus palustris
• Piranhea mexicana
• Platycladus orientalis
• Podocalyx loranthoides
• Podocarpus fasciculus
• Podocarpus macrophyllus
• Quercus canariensis
• Retrophyllum rospigliosii
• Sciadotenia toxifera
• Selaginella moellendorffii
• Sequoiadendron giganteum
• Soulamea pancheri
• Taxodium huegelii
• Trattinnickia glaziovii
• Valeriana microphylla

Cross-Links

• PubChem: 5320644
• NPASS: NPC303485
• ChEMBL: CHEMBL220745
• LOTUS: LTS0254320
• wikiData: Q72501173