Swertianin

Details

• Internal ID: d373fa52-13eb-4dcb-9c9f-f9494ecfdc31
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 1,2,8-trihydroxy-6-methoxyxanthen-9-one
• SMILES (Canonical): COC1=CC(=C2C(=C1)OC3=C(C2=O)C(=C(C=C3)O)O)O
• SMILES (Isomeric): COC1=CC(=C2C(=C1)OC3=C(C2=O)C(=C(C=C3)O)O)O
• InChI: InChI=1S/C14H10O6/c1-19-6-4-8(16)11-10(5-6)20-9-3-2-7(15)13(17)12(9)14(11)18/h2-5,15-17H,1H3
• InChI Key: BDBVOZGRVBXANN-UHFFFAOYSA-N
• Popularity: 11 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

• 20882-75-1
• Gentiakochianin
• 1,2,8-Trihydroxy-6-methoxy-9H-xanthen-9-one
• SWERTIANINE
• 1,2,8-trihydroxy-6-methoxyxanthen-9-one
• Xanthen-9-one, 6-methoxy-1,2,8-trihydroxy-
• 1,7,8-trihydroxy-3-methoxyxanthone
• NSC 289490
• 9H-Xanthen-9-one, 1,2,8-trihydroxy-6-methoxy-
• BRN 1351024
• 890WXQ4KC0
• CHEBI:9371
• CHEMBL187044
• 1,2,8-Trihydroxy-6-methoxyxanthone
• NSC-289490
• 6-Methoxy-1,2,8-trihydroxyxanthen-9-one
• 1,2,8-Trihydroxy-6-methoxy-xanthen-9-one
• GENTIAKOXIANIN
• UNII-890WXQ4KC0
• DTXSID60174998
• BDBM50155435
• NSC289490
• AKOS016010617
• LS-162497
• 3-METHOXY-1,7,8-TRIHYDROXYXANTHONE
• FT-0697995
• Q-100263
• 1,3,7,8-TETRAHYDROXYXANTHONE 3-METHYL ETHER
• Q27108364
• XANTHEN-9-ONE, 1,2,8-TRIHYDROXY-6-METHOXY-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9448	94.48%
Caco-2	+	0.5381	53.81%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7176	71.76%
OATP2B1 inhibitior	-	0.6898	68.98%
OATP1B1 inhibitior	+	0.8920	89.20%
OATP1B3 inhibitior	+	1.0000	100.00%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8879	88.79%
P-glycoprotein inhibitior	-	0.8131	81.31%
P-glycoprotein substrate	-	0.9410	94.10%
CYP3A4 substrate	-	0.5391	53.91%
CYP2C9 substrate	-	0.6887	68.87%
CYP2D6 substrate	-	0.8370	83.70%
CYP3A4 inhibition	-	0.7681	76.81%
CYP2C9 inhibition	-	0.8896	88.96%
CYP2C19 inhibition	-	0.5820	58.20%
CYP2D6 inhibition	-	0.8589	85.89%
CYP1A2 inhibition	+	0.9796	97.96%
CYP2C8 inhibition	+	0.4710	47.10%
CYP inhibitory promiscuity	-	0.5398	53.98%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5599	55.99%
Eye corrosion	-	0.9632	96.32%
Eye irritation	+	0.8491	84.91%
Skin irritation	-	0.5421	54.21%
Skin corrosion	-	0.9458	94.58%
Ames mutagenesis	+	0.8500	85.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7670	76.70%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.8982	89.82%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.7547	75.47%
Acute Oral Toxicity (c)	III	0.7485	74.85%
Estrogen receptor binding	+	0.7716	77.16%
Androgen receptor binding	+	0.8830	88.30%
Thyroid receptor binding	+	0.5404	54.04%
Glucocorticoid receptor binding	+	0.9288	92.88%
Aromatase binding	+	0.8676	86.76%
PPAR gamma	+	0.8318	83.18%
Honey bee toxicity	-	0.9255	92.55%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.8510	85.10%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1951	P21397	Monoamine oxidase A	8500 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	98.45%	91.11%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	94.52%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.18%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.22%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	92.34%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.65%	94.45%
CHEMBL2581	P07339	Cathepsin D	89.26%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.89%	89.00%
CHEMBL3194	P02766	Transthyretin	87.48%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	87.21%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.19%	86.33%
CHEMBL4208	P20618	Proteasome component C5	86.56%	90.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	85.77%	93.99%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.74%	85.14%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	84.60%	93.65%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.51%	99.17%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	84.04%	94.42%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.49%	99.23%
CHEMBL2535	P11166	Glucose transporter	81.00%	98.75%

Plants that contains it

• Brocchia cinerea
• Calophyllum apetalum
• Chironia krebsii
• Delphinium oliverianum
• Drypetes molunduana
• Euphorbia makinoi
• Gentiana acaulis
• Gentiana brachyphylla
• Gentiana scabra
• Gentiana verna
• Gentianella amarella subsp. acuta
• Gentianella nitida
• Gentianopsis simplex
• Lophozia barbata
• Monnina emarginata
• Orphium frutescens
• Polygala fallax
• Pyrus calleryana
• Swertia angustifolia
• Swertia calycina
• Swertia decora
• Swertia iberica
• Swertia japonica
• Swertia perennis
• Swertia pseudochinensis
• Swertia swertopsis
• Swertia thomsonii
• Wettsteinia inversa

Cross-Links

• PubChem: 5281661
• NPASS: NPC62042
• ChEMBL: CHEMBL187044
• LOTUS: LTS0004992
• wikiData: Q27108364