3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-1,5,6-trihydroxyxanthen-9-one

Details

• Internal ID: 347d400a-aa76-49cc-9898-d45a1941f177
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-1,5,6-trihydroxyxanthen-9-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=CC(=C4C(=C3)OC5=C(C4=O)C=CC(=C5O)O)O)CO)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=CC(=C4C(=C3)OC5=C(C4=O)C=CC(=C5O)O)O)CO)O)O)O)O)O
• InChI: InChI=1S/C25H28O15/c1-7-15(29)19(33)21(35)24(36-7)40-23-20(34)18(32)13(6-26)39-25(23)37-8-4-11(28)14-12(5-8)38-22-9(16(14)30)2-3-10(27)17(22)31/h2-5,7,13,15,18-21,23-29,31-35H,6H2,1H3/t7-,13+,15-,18+,19+,20-,21+,23+,24-,25+/m0/s1
• InChI Key: RNQYOSSVXKYFDR-RLHLSZHWSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₈O₁₅
• Molecular Weight: 568.50 g/mol
• Exact Mass: 568.14282018 g/mol
• Topological Polar Surface Area (TPSA): 245.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -1.91
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5561	55.61%
Caco-2	-	0.9216	92.16%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.6195	61.95%
OATP2B1 inhibitior	-	0.5648	56.48%
OATP1B1 inhibitior	+	0.9071	90.71%
OATP1B3 inhibitior	+	0.9627	96.27%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.5623	56.23%
P-glycoprotein inhibitior	-	0.7515	75.15%
P-glycoprotein substrate	-	0.5092	50.92%
CYP3A4 substrate	+	0.6445	64.45%
CYP2C9 substrate	-	0.6847	68.47%
CYP2D6 substrate	-	0.8618	86.18%
CYP3A4 inhibition	-	0.9351	93.51%
CYP2C9 inhibition	-	0.9441	94.41%
CYP2C19 inhibition	-	0.9268	92.68%
CYP2D6 inhibition	-	0.9507	95.07%
CYP1A2 inhibition	-	0.8659	86.59%
CYP2C8 inhibition	+	0.5782	57.82%
CYP inhibitory promiscuity	-	0.8021	80.21%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6996	69.96%
Eye corrosion	-	0.9925	99.25%
Eye irritation	-	0.9238	92.38%
Skin irritation	-	0.8140	81.40%
Skin corrosion	-	0.9645	96.45%
Ames mutagenesis	+	0.6499	64.99%
Human Ether-a-go-go-Related Gene inhibition	-	0.5303	53.03%
Micronuclear	+	0.5933	59.33%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.9073	90.73%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.9384	93.84%
Acute Oral Toxicity (c)	III	0.6235	62.35%
Estrogen receptor binding	+	0.7611	76.11%
Androgen receptor binding	+	0.5529	55.29%
Thyroid receptor binding	+	0.5774	57.74%
Glucocorticoid receptor binding	+	0.5963	59.63%
Aromatase binding	+	0.6903	69.03%
PPAR gamma	+	0.7364	73.64%
Honey bee toxicity	-	0.7329	73.29%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5350	53.50%
Fish aquatic toxicity	+	0.7880	78.80%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.90%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.81%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.54%	89.00%
CHEMBL2581	P07339	Cathepsin D	95.65%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.44%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	92.04%	94.73%
CHEMBL3714130	P46095	G-protein coupled receptor 6	91.88%	97.36%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.71%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.43%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.56%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.89%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.75%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.53%	94.45%
CHEMBL3194	P02766	Transthyretin	85.51%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.84%	97.09%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.48%	96.21%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.29%	99.23%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.59%	86.92%
CHEMBL220	P22303	Acetylcholinesterase	80.98%	94.45%

Plants that contains it

• Hypericum patulum

Cross-Links

• PubChem: 54276319
• LOTUS: LTS0138515
• wikiData: Q105241781