Swerchirin

Details

• Internal ID: 10440758-2d9c-4c5e-966d-32908820be88
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 1,8-dihydroxy-3,5-dimethoxyxanthen-9-one
• SMILES (Canonical): COC1=C2C(=C(C=C1)O)C(=O)C3=C(C=C(C=C3O2)OC)O
• SMILES (Isomeric): COC1=C2C(=C(C=C1)O)C(=O)C3=C(C=C(C=C3O2)OC)O
• InChI: InChI=1S/C15H12O6/c1-19-7-5-9(17)12-11(6-7)21-15-10(20-2)4-3-8(16)13(15)14(12)18/h3-6,16-17H,1-2H3
• InChI Key: GNSHHHWDGOHNPC-UHFFFAOYSA-N
• Popularity: 24 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₂O₆
• Molecular Weight: 288.25 g/mol
• Exact Mass: 288.06338810 g/mol
• Topological Polar Surface Area (TPSA): 85.20 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.37
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• Methylbellidifolin
• 521-65-3
• 1,8-Dihydroxy-3,5-dimethoxyxanthen-9-one
• 5-O-Methylbellidifolin
• 1,8-Dihydroxy-3,5-dimethoxy-9H-xanthen-9-one
• Xanthen-9-one, 1,8-dihydroxy-3,5-dimethoxy-
• 3,5-Dimethoxy-1,8-dihydroxyxanthone
• 9H-Xanthen-9-one, 1,8-dihydroxy-3,5-dimethoxy-
• BRN 0313581
• QQB9X426DM
• 1,8-dihydroxy-3,5-dimethoxyxanthone
• 1,8-dihydroxy-3,5-dimethoxyxanthenone
• C15H12O6
• UNII-QQB9X426DM
• 1,8-DDXO
• CHEBI:9368
• SCHEMBL18240051
• DTXSID80200102
• GNSHHHWDGOHNPC-UHFFFAOYSA-N
• AKOS040754119
• 1,8-dihydroxy-3,5-dimethoxy-xanthenone
• LS-162461
• 1,8-dihydroxy-3,5-dimethoxy-xanthen-9-one
• Q27089378

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9667	96.67%
Caco-2	+	0.7771	77.71%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7124	71.24%
OATP2B1 inhibitior	-	0.7081	70.81%
OATP1B1 inhibitior	+	0.9276	92.76%
OATP1B3 inhibitior	+	0.9684	96.84%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.6534	65.34%
P-glycoprotein inhibitior	-	0.5339	53.39%
P-glycoprotein substrate	-	0.9044	90.44%
CYP3A4 substrate	-	0.5063	50.63%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	+	0.5761	57.61%
CYP2C9 inhibition	-	0.7134	71.34%
CYP2C19 inhibition	+	0.5920	59.20%
CYP2D6 inhibition	-	0.6221	62.21%
CYP1A2 inhibition	+	0.9017	90.17%
CYP2C8 inhibition	+	0.5771	57.71%
CYP inhibitory promiscuity	+	0.5329	53.29%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5697	56.97%
Eye corrosion	-	0.9515	95.15%
Eye irritation	+	0.8648	86.48%
Skin irritation	-	0.6608	66.08%
Skin corrosion	-	0.9812	98.12%
Ames mutagenesis	+	0.9200	92.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7021	70.21%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.9261	92.61%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.5280	52.80%
Acute Oral Toxicity (c)	III	0.7448	74.48%
Estrogen receptor binding	+	0.8734	87.34%
Androgen receptor binding	+	0.8757	87.57%
Thyroid receptor binding	+	0.6492	64.92%
Glucocorticoid receptor binding	+	0.9173	91.73%
Aromatase binding	+	0.7388	73.88%
PPAR gamma	+	0.8391	83.91%
Honey bee toxicity	-	0.9191	91.91%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5649	56.49%
Fish aquatic toxicity	+	0.7067	70.67%

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	96.04%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.84%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.45%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.12%	99.15%
CHEMBL3194	P02766	Transthyretin	92.05%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.30%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.30%	86.33%
CHEMBL4208	P20618	Proteasome component C5	87.97%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.88%	94.45%
CHEMBL2535	P11166	Glucose transporter	87.33%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.61%	99.17%
CHEMBL2581	P07339	Cathepsin D	84.89%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.68%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	83.36%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.28%	85.14%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	81.54%	93.65%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.75%	93.99%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	80.32%	80.78%

Plants that contains it

• Centaurium erythraea
• Centaurium littorale
• Frasera albomarginata
• Gentiana algida
• Gentiana thunbergii
• Gentianella florida
• Gentianella magellanica
• Gentianopsis crinita
• Lomatogonium rotatum
• Schenkia spicata
• Swertia calycina
• Swertia chirata
• Swertia chirayta
• Swertia japonica
• Swertia petiolata
• Swertia pseudochinensis
• Swertia swertopsis
• Vaccaria hispanica

Cross-Links

• PubChem: 5281660
• NPASS: NPC92381
• LOTUS: LTS0018263
• wikiData: Q27089378