2,3,5-trimethoxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxyxanthen-9-one

Details

• Internal ID: 631147ca-47e0-4b26-9044-b4879963f267
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 2,3,5-trimethoxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxyxanthen-9-one
• SMILES (Canonical): COC1=CC=CC2=C1OC3=CC(=C(C(=C3C2=O)OC4C(C(C(C(O4)COC5C(C(C(CO5)O)O)O)O)O)O)OC)OC
• SMILES (Isomeric): COC1=CC=CC2=C1OC3=CC(=C(C(=C3C2=O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO[C@H]5[C@@H]([C@H]([C@@H](CO5)O)O)O)O)O)O)OC)OC
• InChI: InChI=1S/C27H32O15/c1-35-12-6-4-5-10-17(29)16-13(40-23(10)12)7-14(36-2)24(37-3)25(16)42-27-22(34)20(32)19(31)15(41-27)9-39-26-21(33)18(30)11(28)8-38-26/h4-7,11,15,18-22,26-28,30-34H,8-9H2,1-3H3/t11-,15-,18+,19-,20+,21-,22-,26+,27+/m1/s1
• InChI Key: RUASYNDFIPXRFB-WJSXLNBQSA-N
• Popularity: 0 references 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): 212.00 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): -1.39
• H-Bond Acceptor: 15
• H-Bond Donor: 6
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5187	51.87%
Caco-2	-	0.8684	86.84%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5499	54.99%
OATP2B1 inhibitior	-	0.8562	85.62%
OATP1B1 inhibitior	+	0.9036	90.36%
OATP1B3 inhibitior	+	0.9399	93.99%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.6376	63.76%
P-glycoprotein inhibitior	-	0.4878	48.78%
P-glycoprotein substrate	+	0.6154	61.54%
CYP3A4 substrate	+	0.6854	68.54%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8241	82.41%
CYP3A4 inhibition	-	0.9524	95.24%
CYP2C9 inhibition	-	0.9638	96.38%
CYP2C19 inhibition	-	0.9380	93.80%
CYP2D6 inhibition	-	0.9114	91.14%
CYP1A2 inhibition	-	0.8567	85.67%
CYP2C8 inhibition	+	0.5280	52.80%
CYP inhibitory promiscuity	-	0.9232	92.32%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6946	69.46%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9296	92.96%
Skin irritation	-	0.8471	84.71%
Skin corrosion	-	0.9654	96.54%
Ames mutagenesis	+	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7178	71.78%
Micronuclear	+	0.5474	54.74%
Hepatotoxicity	-	0.6073	60.73%
skin sensitisation	-	0.9045	90.45%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.9671	96.71%
Acute Oral Toxicity (c)	III	0.7104	71.04%
Estrogen receptor binding	+	0.8272	82.72%
Androgen receptor binding	+	0.6068	60.68%
Thyroid receptor binding	+	0.5399	53.99%
Glucocorticoid receptor binding	+	0.6480	64.80%
Aromatase binding	+	0.6164	61.64%
PPAR gamma	+	0.7037	70.37%
Honey bee toxicity	-	0.8021	80.21%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.8158	81.58%

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	99.18%	91.11%
CHEMBL220	P22303	Acetylcholinesterase	97.97%	94.45%
CHEMBL2581	P07339	Cathepsin D	96.73%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.11%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.10%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.03%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.02%	89.00%
CHEMBL2535	P11166	Glucose transporter	93.69%	98.75%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.13%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.25%	86.33%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	91.12%	89.62%
CHEMBL4302	P08183	P-glycoprotein 1	90.38%	92.98%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	89.74%	94.03%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.49%	96.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.00%	97.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.92%	99.23%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.55%	92.62%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.06%	97.14%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.72%	95.83%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.52%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.50%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.74%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.64%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	81.23%	94.73%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.18%	95.50%

Plants that contains it

• Halenia corniculata
• Halenia elata
• Halenia elliptica

Cross-Links

• PubChem: 102145651
• LOTUS: LTS0220449
• wikiData: Q105245537