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

Details

• Internal ID: d8138784-2bf9-4680-b188-84b9996f4c3a
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 2,3,5-trimethoxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-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(C(O5)CO)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]([C@H](O5)CO)O)O)O)O)O)O)OC)OC
• InChI: InChI=1S/C28H34O16/c1-37-11-6-4-5-10-17(30)16-12(41-24(10)11)7-13(38-2)25(39-3)26(16)44-28-23(36)21(34)19(32)15(43-28)9-40-27-22(35)20(33)18(31)14(8-29)42-27/h4-7,14-15,18-23,27-29,31-36H,8-9H2,1-3H3/t14-,15-,18-,19-,20+,21+,22-,23-,27-,28+/m1/s1
• InChI Key: OQGAMLATFWOIDP-ZEACKCBFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₄O₁₆
• Molecular Weight: 626.60 g/mol
• Exact Mass: 626.18468499 g/mol
• Topological Polar Surface Area (TPSA): 233.00 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): -2.03
• H-Bond Acceptor: 16
• H-Bond Donor: 7
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6438	64.38%
Caco-2	-	0.8788	87.88%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.4956	49.56%
OATP2B1 inhibitior	-	0.8552	85.52%
OATP1B1 inhibitior	+	0.8870	88.70%
OATP1B3 inhibitior	+	0.9658	96.58%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7173	71.73%
P-glycoprotein inhibitior	-	0.4641	46.41%
P-glycoprotein substrate	+	0.5115	51.15%
CYP3A4 substrate	+	0.6579	65.79%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8291	82.91%
CYP3A4 inhibition	-	0.9611	96.11%
CYP2C9 inhibition	-	0.9472	94.72%
CYP2C19 inhibition	-	0.9245	92.45%
CYP2D6 inhibition	-	0.9420	94.20%
CYP1A2 inhibition	-	0.9014	90.14%
CYP2C8 inhibition	+	0.5446	54.46%
CYP inhibitory promiscuity	-	0.8280	82.80%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6867	68.67%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9260	92.60%
Skin irritation	-	0.8519	85.19%
Skin corrosion	-	0.9664	96.64%
Ames mutagenesis	+	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7762	77.62%
Micronuclear	+	0.5633	56.33%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.9185	91.85%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.8428	84.28%
Acute Oral Toxicity (c)	III	0.7088	70.88%
Estrogen receptor binding	+	0.8406	84.06%
Androgen receptor binding	+	0.5807	58.07%
Thyroid receptor binding	+	0.5283	52.83%
Glucocorticoid receptor binding	+	0.6470	64.70%
Aromatase binding	+	0.6424	64.24%
PPAR gamma	+	0.7013	70.13%
Honey bee toxicity	-	0.8021	80.21%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.6682	66.82%

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	98.72%	91.11%
CHEMBL220	P22303	Acetylcholinesterase	97.80%	94.45%
CHEMBL2581	P07339	Cathepsin D	95.76%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.83%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.61%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.60%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.87%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.63%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.62%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.45%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.22%	99.17%
CHEMBL2535	P11166	Glucose transporter	89.37%	98.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.86%	99.23%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	86.64%	94.03%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.77%	95.83%
CHEMBL3401	O75469	Pregnane X receptor	84.76%	94.73%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.09%	97.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.77%	92.62%
CHEMBL4302	P08183	P-glycoprotein 1	83.57%	92.98%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.43%	89.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.27%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.78%	95.89%

Plants that contains it

• Halenia corniculata
• Halenia elata
• Halenia elliptica

Cross-Links

• PubChem: 102154410
• LOTUS: LTS0272111
• wikiData: Q105196777