Bellidifolin

Details

• Internal ID: 24de5f82-18da-4566-a884-5392027c509f
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 1,5,8-trihydroxy-3-methoxyxanthen-9-one
• SMILES (Canonical): COC1=CC(=C2C(=C1)OC3=C(C=CC(=C3C2=O)O)O)O
• SMILES (Isomeric): COC1=CC(=C2C(=C1)OC3=C(C=CC(=C3C2=O)O)O)O
• InChI: InChI=1S/C14H10O6/c1-19-6-4-9(17)11-10(5-6)20-14-8(16)3-2-7(15)12(14)13(11)18/h2-5,15-17H,1H3
• InChI Key: JDIORNFCMMYMLF-UHFFFAOYSA-N
• Popularity: 38 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₀O₆
• Molecular Weight: 274.22 g/mol
• Exact Mass: 274.04773803 g/mol
• Topological Polar Surface Area (TPSA): 96.20 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.07
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• 2798-25-6
• 1,5,8-Trihydroxy-3-methoxy-9H-xanthen-9-one
• Bellidifoline
• Bellidifolium
• CCRIS 5471
• 1,5,8-trihydroxy-3-methoxyxanthen-9-one
• Xanthen-9-one, 3-methoxy-1,5,8-trihydroxy-
• 3-Methoxy-1,5,8-trihydroxyxanthone
• 9H-Xanthen-9-one, 1,5,8-trihydroxy-3-methoxy-
• BRN 0288441
• 3-Methoxy-1,5,8-trihydroxyxanthen-9-one
• CHEBI:3008
• CHEMBL185776
• 1,5,8-Trihydroxy-3-methoxy-xanthen-9-one
• Xanthen-9-one, 1.1
• MLS002473044
• X522Q6XJR9
• DTXSID30182262
• HMS2270C16
• CAA79825
• HY-N2000
• 1,5,8-trihydroxy-3-methoxyxanthone
• BDBM50155420
• AKOS016010654
• 1,5,8-trihydroxyl-3-methoxy xanthone
• NCGC00247483-01
• 3-Methoxy-1,5,8-trihyroxyxanthen-9-one
• AC-34445
• MS-23889
• SMR001397148
• LS-162496
• CS-0018319
• FT-0698157
• C10053
• Xanthen-9-one, 1,5,8-trihydroxy-3-methoxy-
• Q-100356
• Q27067443

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9733	97.33%
Caco-2	+	0.5074	50.74%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7066	70.66%
OATP2B1 inhibitior	-	0.6877	68.77%
OATP1B1 inhibitior	+	0.9289	92.89%
OATP1B3 inhibitior	+	0.9925	99.25%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.8120	81.20%
P-glycoprotein inhibitior	-	0.7830	78.30%
P-glycoprotein substrate	-	0.9399	93.99%
CYP3A4 substrate	-	0.5371	53.71%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	-	0.5248	52.48%
CYP2C9 inhibition	-	0.5620	56.20%
CYP2C19 inhibition	+	0.6608	66.08%
CYP2D6 inhibition	-	0.7551	75.51%
CYP1A2 inhibition	+	0.9602	96.02%
CYP2C8 inhibition	-	0.5812	58.12%
CYP inhibitory promiscuity	+	0.5452	54.52%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4815	48.15%
Eye corrosion	-	0.9346	93.46%
Eye irritation	+	0.8889	88.89%
Skin irritation	-	0.5868	58.68%
Skin corrosion	-	0.9760	97.60%
Ames mutagenesis	+	0.9600	96.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8475	84.75%
Micronuclear	+	0.8300	83.00%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.9346	93.46%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.9071	90.71%
Estrogen receptor binding	+	0.7603	76.03%
Androgen receptor binding	+	0.8479	84.79%
Thyroid receptor binding	+	0.5778	57.78%
Glucocorticoid receptor binding	+	0.9438	94.38%
Aromatase binding	+	0.8246	82.46%
PPAR gamma	+	0.8954	89.54%
Honey bee toxicity	-	0.9333	93.33%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.6561	65.61%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1951	P21397	Monoamine oxidase A	660 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	98.29%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.80%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.27%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.94%	94.00%
CHEMBL3194	P02766	Transthyretin	89.89%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.78%	94.45%
CHEMBL4208	P20618	Proteasome component C5	87.80%	90.00%
CHEMBL3401	O75469	Pregnane X receptor	87.20%	94.73%
CHEMBL2581	P07339	Cathepsin D	87.18%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.50%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.94%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.30%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.05%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.58%	99.23%
CHEMBL2535	P11166	Glucose transporter	83.54%	98.75%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	82.76%	93.65%

Plants that contains it

• Gentiana acaulis
• Gentiana algida
• Gentiana lutea
• Gentiana thunbergii
• Gentianella campestris
• Gentianella florida
• Gentianella magellanica
• Gentianella turkestanorum
• Iris nigricans
• Swertia chirata
• Swertia chirayta
• Swertia ciliata
• Swertia hookeri
• Swertia japonica
• Swertia pseudochinensis
• Swertia speciosa

Cross-Links

• PubChem: 5281623
• NPASS: NPC199100
• ChEMBL: CHEMBL185776
• LOTUS: LTS0107270
• wikiData: Q27067443