Demethylbellidifolin

Details

• Internal ID: 3ada30f8-e306-4ed4-89c0-0e13d84bf17a
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 1,3,5,8-tetrahydroxyxanthen-9-one
• InChI: InChI=1S/C13H8O6/c14-5-3-8(17)10-9(4-5)19-13-7(16)2-1-6(15)11(13)12(10)18/h1-4,14-17H
• InChI Key: MPXAWSABMVLIBU-UHFFFAOYSA-N
• Popularity: 40 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₈O₆
• Molecular Weight: 260.20 g/mol
• Exact Mass: 260.03208797 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 1.77
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 0

Synonyms

• Demethylbellidifolin
• Bellidin
• 1,3,5,8-Tetrahydroxyxanthen-9-one
• 9H-Xanthen-9-one, 1,3,5,8-tetrahydroxy-
• CHEBI:65480
• DTXSID80183941
• RefChem:919833
• DTXCID20106432
• Desmethylbellidifolin
• 1,3,5,8-Tetrahydroxyxanthone
• 1,3,5,8-Tetrahydroxy-9H-xanthen-9-one
• tetrahydroxyxanthone
• Desmethybellidifolin
• Xanthen-9-one, 1,3,5,8-tetrahydroxy-
• 1,3,5,8-Tetrahydroxylxanthone
• CHEMBL184574
• G78B8Y1AI5
• MFCD01741488
• 1,3,5,8-tetrakis(oxidanyl)xanthen-9-one
• Bellidin (Demethylbellidifolin)
• Norbellidifodin
• CCRIS 3853
• BRN 0286545
• NORBELLIDIFOLIN
• Xanthen-9-one, 1.0
• DESMETHYLBELLIDIFOLINE
• UNII-G78B8Y1AI5
• orb1297564
• SCHEMBL9838546
• SCHEMBL29935551
• MPXAWSABMVLIBU-UHFFFAOYSA-N
• HY-N2050
• 1,3,5,8-Tetrahyroxyxanthen-9-one
• BDBM50155426
• 1,3,5,8-Tetrahydroxyxanthone,85%
• AKOS030562784
• 1,3,5,8-Tetrahydroxy-xanthen-9-one
• AC-34631
• DA-72686
• MS-23662
• CS-0018539
• AA-504/21125006
• AN-668/21246007
• 1,3,5,8-Tetrahydroxyxanthone; Desmethylbellidifolin
• Q27133925
• EKU

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9361	93.61%
Caco-2	-	0.7653	76.53%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.5131	51.31%
OATP2B1 inhibitior	-	0.6423	64.23%
OATP1B1 inhibitior	+	0.8976	89.76%
OATP1B3 inhibitior	+	0.9503	95.03%
MATE1 inhibitior	-	0.5200	52.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8719	87.19%
P-glycoprotein inhibitior	-	0.9371	93.71%
P-glycoprotein substrate	-	0.9398	93.98%
CYP3A4 substrate	-	0.5904	59.04%
CYP2C9 substrate	-	0.6265	62.65%
CYP2D6 substrate	-	0.8495	84.95%
CYP3A4 inhibition	+	0.8524	85.24%
CYP2C9 inhibition	-	0.5893	58.93%
CYP2C19 inhibition	-	0.6902	69.02%
CYP2D6 inhibition	-	0.8729	87.29%
CYP1A2 inhibition	+	0.9342	93.42%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	+	0.5294	52.94%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6043	60.43%
Eye corrosion	-	0.9785	97.85%
Eye irritation	+	0.9676	96.76%
Skin irritation	+	0.6154	61.54%
Skin corrosion	-	0.9716	97.16%
Ames mutagenesis	+	0.9500	95.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8941	89.41%
Micronuclear	+	0.8000	80.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.7699	76.99%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	+	0.5394	53.94%
Acute Oral Toxicity (c)	III	0.6625	66.25%
Estrogen receptor binding	+	0.7749	77.49%
Androgen receptor binding	+	0.8439	84.39%
Thyroid receptor binding	+	0.6067	60.67%
Glucocorticoid receptor binding	+	0.9336	93.36%
Aromatase binding	+	0.7870	78.70%
PPAR gamma	+	0.8976	89.76%
Honey bee toxicity	-	0.9268	92.68%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.7280	72.80%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1951	P21397	Monoamine oxidase A	13000 nM	IC50	PMID: 15482934

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.00%	91.11%
CHEMBL3194	P02766	Transthyretin	94.96%	90.71%
CHEMBL1929	P47989	Xanthine dehydrogenase	92.74%	96.12%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.31%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.93%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	86.08%	94.73%
CHEMBL2581	P07339	Cathepsin D	85.46%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.20%	99.15%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.57%	99.23%
CHEMBL1951	P21397	Monoamine oxidase A	84.12%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.99%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.64%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.17%	86.33%
CHEMBL4208	P20618	Proteasome component C5	81.69%	90.00%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	80.16%	93.65%

Plants that contains it

• Barbilophozia barbata
• Calophyllum apetalum
• Delphinium oliverianum
• Drypetes stipularis
• Euphorbia makinoi
• Gentiana acaulis
• Gentiana taliensis
• Gentiana thunbergii
• Gentianella amarella
• Gentianella amarella subsp. acuta
• Gentianella bellidifolia
• Gentianella campestris
• Gentianella florida
• Gentianella nitida
• Gentianopsis ciliata
• Hypericum henryi
• Iris nigricans
• Monnina emarginata
• Polygala fallax
• Pyrus calleryana
• Schkuhria schkuhrioides
• Swertia calycina
• Swertia chirayita
• Swertia davidii
• Swertia hookeri
• Swertia japonica
• Swertia lawii
• Swertia macrosperma
• Swertia pseudochinensis
• Wettsteinia inversa

Cross-Links

• PubChem: 5281626
• NPASS: NPC61620
• ChEMBL: CHEMBL184574
• LOTUS: LTS0039247
• wikiData: Q105340793