3-[(2R,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-1,7-dihydroxyxanthen-9-one

Details

• Internal ID: 315bcf22-cc3c-49ef-a191-91d7ca90d1f3
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 3-[(2R,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-1,7-dihydroxyxanthen-9-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=CC(=C4C(=C3)OC5=C(C4=O)C=C(C=C5)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=C(C=C5)O)O)CO)O)O)O)O)O
• InChI: InChI=1S/C25H28O14/c1-8-17(29)20(32)22(34)24(35-8)39-23-21(33)19(31)15(7-26)38-25(23)36-10-5-12(28)16-14(6-10)37-13-3-2-9(27)4-11(13)18(16)30/h2-6,8,15,17,19-29,31-34H,7H2,1H3/t8-,15+,17-,19+,20+,21-,22+,23+,24-,25-/m0/s1
• InChI Key: VWOARAFDOWHQIV-WMUVIVARSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₈O₁₄
• Molecular Weight: 552.50 g/mol
• Exact Mass: 552.14790556 g/mol
• Topological Polar Surface Area (TPSA): 225.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -1.61
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5998	59.98%
Caco-2	-	0.9112	91.12%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6483	64.83%
OATP2B1 inhibitior	-	0.7007	70.07%
OATP1B1 inhibitior	+	0.8988	89.88%
OATP1B3 inhibitior	+	0.9671	96.71%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.6044	60.44%
P-glycoprotein inhibitior	-	0.8025	80.25%
P-glycoprotein substrate	-	0.5095	50.95%
CYP3A4 substrate	+	0.6417	64.17%
CYP2C9 substrate	-	0.6986	69.86%
CYP2D6 substrate	-	0.8617	86.17%
CYP3A4 inhibition	-	0.9417	94.17%
CYP2C9 inhibition	-	0.9552	95.52%
CYP2C19 inhibition	-	0.9427	94.27%
CYP2D6 inhibition	-	0.9493	94.93%
CYP1A2 inhibition	-	0.9020	90.20%
CYP2C8 inhibition	+	0.5393	53.93%
CYP inhibitory promiscuity	-	0.8183	81.83%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6495	64.95%
Eye corrosion	-	0.9920	99.20%
Eye irritation	-	0.9370	93.70%
Skin irritation	-	0.8214	82.14%
Skin corrosion	-	0.9690	96.90%
Ames mutagenesis	+	0.7463	74.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.4168	41.68%
Micronuclear	+	0.5633	56.33%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.9235	92.35%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.9411	94.11%
Acute Oral Toxicity (c)	III	0.6607	66.07%
Estrogen receptor binding	+	0.7644	76.44%
Androgen receptor binding	+	0.5359	53.59%
Thyroid receptor binding	+	0.5817	58.17%
Glucocorticoid receptor binding	+	0.5609	56.09%
Aromatase binding	+	0.6871	68.71%
PPAR gamma	+	0.7857	78.57%
Honey bee toxicity	-	0.7077	70.77%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.7355	73.55%

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	99.45%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.35%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.72%	89.00%
CHEMBL2581	P07339	Cathepsin D	96.67%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.30%	94.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	93.33%	97.36%
CHEMBL3401	O75469	Pregnane X receptor	92.69%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.86%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.11%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.63%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.22%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.14%	97.09%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	84.56%	93.10%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.52%	95.89%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.01%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.53%	94.45%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.69%	95.83%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.48%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.34%	86.92%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.06%	97.33%

Plants that contains it

• Polygala tenuifolia

Cross-Links

• PubChem: 163069413
• LOTUS: LTS0235688
• wikiData: Q105298195