6-[(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-hydroxy-3,7-dimethoxyxanthen-9-one

Details

• Internal ID: 0a648587-d123-4eac-aefb-09c0fc533381
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 6-[(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-hydroxy-3,7-dimethoxyxanthen-9-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=C(C=C4C(=C3)OC5=CC(=CC(=C5C4=O)O)OC)OC)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=C(C=C4C(=C3)OC5=CC(=CC(=C5C4=O)O)OC)OC)CO)O)O)O)O)O
• InChI: InChI=1S/C27H32O15/c1-9-19(30)22(33)24(35)26(38-9)42-25-23(34)21(32)17(8-28)41-27(25)40-15-7-13-11(6-14(15)37-3)20(31)18-12(29)4-10(36-2)5-16(18)39-13/h4-7,9,17,19,21-30,32-35H,8H2,1-3H3/t9-,17+,19-,21+,22+,23-,24+,25+,26-,27+/m0/s1
• InChI Key: LCUUDEGZJCYIRC-CQUWOCBCSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₂O₁₅
• Molecular Weight: 596.50 g/mol
• Exact Mass: 596.17412031 g/mol
• Topological Polar Surface Area (TPSA): 223.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -1.30
• H-Bond Acceptor: 15
• H-Bond Donor: 7
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5904	59.04%
Caco-2	-	0.8866	88.66%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.5170	51.70%
OATP2B1 inhibitior	-	0.7226	72.26%
OATP1B1 inhibitior	+	0.8881	88.81%
OATP1B3 inhibitior	+	0.9530	95.30%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.6108	61.08%
P-glycoprotein inhibitior	-	0.6371	63.71%
P-glycoprotein substrate	+	0.5785	57.85%
CYP3A4 substrate	+	0.6394	63.94%
CYP2C9 substrate	-	0.8740	87.40%
CYP2D6 substrate	-	0.8547	85.47%
CYP3A4 inhibition	-	0.9367	93.67%
CYP2C9 inhibition	-	0.9525	95.25%
CYP2C19 inhibition	-	0.9383	93.83%
CYP2D6 inhibition	-	0.9272	92.72%
CYP1A2 inhibition	-	0.8728	87.28%
CYP2C8 inhibition	+	0.5567	55.67%
CYP inhibitory promiscuity	-	0.8307	83.07%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7093	70.93%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9358	93.58%
Skin irritation	-	0.8380	83.80%
Skin corrosion	-	0.9663	96.63%
Ames mutagenesis	+	0.6472	64.72%
Human Ether-a-go-go-Related Gene inhibition	-	0.3917	39.17%
Micronuclear	+	0.5833	58.33%
Hepatotoxicity	-	0.7601	76.01%
skin sensitisation	-	0.9269	92.69%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.9426	94.26%
Acute Oral Toxicity (c)	III	0.6857	68.57%
Estrogen receptor binding	+	0.8062	80.62%
Androgen receptor binding	-	0.5125	51.25%
Thyroid receptor binding	+	0.5487	54.87%
Glucocorticoid receptor binding	+	0.6515	65.15%
Aromatase binding	+	0.6119	61.19%
PPAR gamma	+	0.7548	75.48%
Honey bee toxicity	-	0.7195	71.95%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.7092	70.92%

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	99.34%	91.11%
CHEMBL3714130	P46095	G-protein coupled receptor 6	96.55%	97.36%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.30%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.98%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.13%	85.14%
CHEMBL1951	P21397	Monoamine oxidase A	93.64%	91.49%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.17%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.02%	95.56%
CHEMBL2581	P07339	Cathepsin D	92.72%	98.95%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.14%	96.21%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.94%	92.94%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.48%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.02%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	86.55%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.30%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.94%	97.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.26%	99.15%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.42%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.40%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.11%	96.00%

Plants that contains it

• Polygala tenuifolia

Cross-Links

• PubChem: 11972435
• NPASS: NPC20377
• LOTUS: LTS0055275
• wikiData: Q105150003