Tripteroside

Details

• Internal ID: 4f816669-f537-4650-9354-3f11a062f4b5
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 1,3,7-trihydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyxanthen-9-one
• SMILES (Canonical): C1=C(C=C2C(=C1O)C(=O)C3=CC(=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O)O
• SMILES (Isomeric): C1=C(C=C2C(=C1O)C(=O)C3=CC(=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O
• InChI: InChI=1S/C19H18O11/c20-5-13-16(25)17(26)18(27)19(30-13)29-11-4-10-7(3-8(11)22)15(24)14-9(23)1-6(21)2-12(14)28-10/h1-4,13,16-23,25-27H,5H2/t13-,16-,17+,18-,19-/m1/s1
• InChI Key: DSJIWZUDANJKCU-LQDZTQBFSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₈O₁₁
• Molecular Weight: 422.30 g/mol
• Exact Mass: 422.08491139 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): -0.76
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 3

Synonyms

• Norathyriol-6-O-beta-D-glucoside
• 82855-00-3
• C10095
• 1,3,7-trihydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyxanthen-9-one
• AC1NQYUG
• CHEBI:9746
• DTXSID60415171
• Q27108487
• 2,6,8-trihydroxy-9-oxo-9H-xanthen-3-yl beta-D-glucopyranoside
• 1,3,7-trihydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-xanthen-9-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5923	59.23%
Caco-2	-	0.9222	92.22%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.5362	53.62%
OATP2B1 inhibitior	+	0.5922	59.22%
OATP1B1 inhibitior	+	0.8911	89.11%
OATP1B3 inhibitior	+	0.9389	93.89%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.7551	75.51%
P-glycoprotein inhibitior	-	0.8047	80.47%
P-glycoprotein substrate	-	0.7176	71.76%
CYP3A4 substrate	+	0.5729	57.29%
CYP2C9 substrate	-	0.6762	67.62%
CYP2D6 substrate	-	0.8575	85.75%
CYP3A4 inhibition	-	0.9207	92.07%
CYP2C9 inhibition	-	0.9414	94.14%
CYP2C19 inhibition	-	0.9119	91.19%
CYP2D6 inhibition	-	0.9327	93.27%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.4882	48.82%
CYP inhibitory promiscuity	-	0.8472	84.72%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7090	70.90%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.7999	79.99%
Skin irritation	-	0.7983	79.83%
Skin corrosion	-	0.9715	97.15%
Ames mutagenesis	+	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6258	62.58%
Micronuclear	+	0.6033	60.33%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.8796	87.96%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.7927	79.27%
Acute Oral Toxicity (c)	III	0.4513	45.13%
Estrogen receptor binding	+	0.7637	76.37%
Androgen receptor binding	+	0.5734	57.34%
Thyroid receptor binding	+	0.6037	60.37%
Glucocorticoid receptor binding	+	0.7550	75.50%
Aromatase binding	+	0.6371	63.71%
PPAR gamma	+	0.6735	67.35%
Honey bee toxicity	-	0.7484	74.84%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6699	66.99%
Fish aquatic toxicity	+	0.7790	77.90%

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	98.85%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.75%	89.00%
CHEMBL2581	P07339	Cathepsin D	92.48%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.14%	94.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.07%	96.21%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.61%	99.17%
CHEMBL3194	P02766	Transthyretin	89.96%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	87.45%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.47%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	84.57%	91.49%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.83%	86.92%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.92%	92.94%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.65%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.55%	94.45%

Plants that contains it

• Delairea odorata
• Hypericum patulum
• Tripterospermum taiwanense
• Tripterygium wilfordii

Cross-Links

• PubChem: 5281664
• NPASS: NPC255184
• LOTUS: LTS0210431
• wikiData: Q27108487