Swertiajaponin

Details

• Internal ID: 8507500a-6454-4925-b448-21b2ef0f33ee
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
• SMILES (Canonical): COC1=C(C(=C2C(=C1)OC(=CC2=O)C3=CC(=C(C=C3)O)O)O)C4C(C(C(C(O4)CO)O)O)O
• SMILES (Isomeric): COC1=C(C(=C2C(=C1)OC(=CC2=O)C3=CC(=C(C=C3)O)O)O)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
• InChI: InChI=1S/C22H22O11/c1-31-13-6-14-16(11(26)5-12(32-14)8-2-3-9(24)10(25)4-8)19(28)17(13)22-21(30)20(29)18(27)15(7-23)33-22/h2-6,15,18,20-25,27-30H,7H2,1H3/t15-,18-,20+,21-,22+/m1/s1
• InChI Key: DLVLXOYLQKCAME-DGHBBABESA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₂O₁₁
• Molecular Weight: 462.40 g/mol
• Exact Mass: 462.11621151 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 0.10
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 4

Synonyms

• 6980-25-2
• Leucanthoside
• C10187
• 4H-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-6-beta-D-glucopyranosyl-5 -hydroxy-7-methoxy-
• 2-(3,4-Dihydroxyphenyl)-5-hydroxy-7-methoxy-6-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-oneertiajaponin
• 4H-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-6-beta-D-glucopyranosyl-5-hydroxy-7-methoxy-
• AC1L9D6B
• 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
• SureCN4783737
• SCHEMBL4783737
• CHEMBL4160301
• DTXSID90990062
• HY-N2204
• AKOS037515193
• MS-28491
• CS-0019510
• 1,5-Anhydro-1-[2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4-oxo-4H-1-benzopyran-6-yl]hexitol
• 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6545	65.45%
Caco-2	-	0.8871	88.71%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6233	62.33%
OATP2B1 inhibitior	+	0.5894	58.94%
OATP1B1 inhibitior	+	0.8363	83.63%
OATP1B3 inhibitior	+	0.9830	98.30%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.4791	47.91%
P-glycoprotein inhibitior	-	0.6230	62.30%
P-glycoprotein substrate	-	0.6288	62.88%
CYP3A4 substrate	+	0.6091	60.91%
CYP2C9 substrate	-	0.8129	81.29%
CYP2D6 substrate	-	0.8347	83.47%
CYP3A4 inhibition	-	0.7983	79.83%
CYP2C9 inhibition	-	0.8483	84.83%
CYP2C19 inhibition	-	0.8386	83.86%
CYP2D6 inhibition	-	0.9339	93.39%
CYP1A2 inhibition	-	0.8015	80.15%
CYP2C8 inhibition	+	0.7272	72.72%
CYP inhibitory promiscuity	-	0.6314	63.14%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6988	69.88%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9016	90.16%
Skin irritation	-	0.8040	80.40%
Skin corrosion	-	0.9556	95.56%
Ames mutagenesis	+	0.6135	61.35%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	+	0.6359	63.59%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.9200	92.00%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.9001	90.01%
Acute Oral Toxicity (c)	III	0.6599	65.99%
Estrogen receptor binding	+	0.7285	72.85%
Androgen receptor binding	+	0.7622	76.22%
Thyroid receptor binding	+	0.5631	56.31%
Glucocorticoid receptor binding	+	0.7039	70.39%
Aromatase binding	-	0.5547	55.47%
PPAR gamma	+	0.7204	72.04%
Honey bee toxicity	-	0.7249	72.49%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6549	65.49%
Fish aquatic toxicity	-	0.4258	42.58%

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	99.74%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.23%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.04%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.55%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.85%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.51%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.34%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.06%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.90%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.69%	86.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	88.46%	96.21%
CHEMBL3401	O75469	Pregnane X receptor	85.37%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.68%	99.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.59%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.21%	96.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.03%	97.14%

Plants that contains it

• Alliaria petiolata
• Arrhenatherum elatius
• Carex fraseriana
• Cornus officinalis
• Cymbopogon citratus
• Deschampsia antarctica
• Gnetum gnemon
• Iris lactea
• Leiothrix flavescens
• Lophatherum gracile
• Passiflora biflora
• Passiflora sexflora
• Phragmites australis
• Pterocephalus plumosus
• Saccharum officinarum
• Swertia japonica
• Swertia pseudochinensis

Cross-Links

• PubChem: 442659
• NPASS: NPC29565
• LOTUS: LTS0139353
• wikiData: Q104984738