Lethedioside A

Details

• Internal ID: 4079128f-0818-456b-93a2-201a7cbc4609
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides
• IUPAC Name: 2-(3,4-dimethoxyphenyl)-7-methoxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): COC1=C(C=C(C=C1)C2=CC(=O)C3=C(O2)C=C(C=C3OC4C(C(C(C(O4)COC5C(C(C(CO5)O)O)O)O)O)O)OC)OC
• SMILES (Isomeric): COC1=C(C=C(C=C1)C2=CC(=O)C3=C(O2)C=C(C=C3O[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/C29H34O15/c1-37-13-7-19-22(14(30)9-17(42-19)12-4-5-16(38-2)18(6-12)39-3)20(8-13)43-29-27(36)25(34)24(33)21(44-29)11-41-28-26(35)23(32)15(31)10-40-28/h4-9,15,21,23-29,31-36H,10-11H2,1-3H3/t15-,21-,23+,24-,25+,26-,27-,28+,29-/m1/s1
• InChI Key: OQEZCWWFGXYLQY-YUYUGGDUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₄O₁₅
• Molecular Weight: 622.60 g/mol
• Exact Mass: 622.18977037 g/mol
• Topological Polar Surface Area (TPSA): 212.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): -0.87
• H-Bond Acceptor: 15
• H-Bond Donor: 6
• Rotatable Bonds: 9

Synonyms

• 221289-31-2
• 2-(3,4-dimethoxyphenyl)-7-methoxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
• CHEMBL442846
• AKOS032961787
• 2-(3,4-Dimethoxyphenyl)-7-methoxy-5-[(6-O--D-xylopyranosyl--D-glucopyranosyl)oxy]-4H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5725	57.25%
Caco-2	-	0.8651	86.51%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6292	62.92%
OATP2B1 inhibitior	-	0.7156	71.56%
OATP1B1 inhibitior	+	0.8802	88.02%
OATP1B3 inhibitior	+	0.9356	93.56%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.6805	68.05%
P-glycoprotein inhibitior	-	0.4664	46.64%
P-glycoprotein substrate	+	0.5713	57.13%
CYP3A4 substrate	+	0.6333	63.33%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8241	82.41%
CYP3A4 inhibition	-	0.9614	96.14%
CYP2C9 inhibition	-	0.9537	95.37%
CYP2C19 inhibition	-	0.9382	93.82%
CYP2D6 inhibition	-	0.9374	93.74%
CYP1A2 inhibition	-	0.9184	91.84%
CYP2C8 inhibition	+	0.6295	62.95%
CYP inhibitory promiscuity	-	0.8791	87.91%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6942	69.42%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9273	92.73%
Skin irritation	-	0.8485	84.85%
Skin corrosion	-	0.9632	96.32%
Ames mutagenesis	+	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8092	80.92%
Micronuclear	+	0.6174	61.74%
Hepatotoxicity	-	0.8625	86.25%
skin sensitisation	-	0.9243	92.43%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.9380	93.80%
Acute Oral Toxicity (c)	III	0.6930	69.30%
Estrogen receptor binding	+	0.8511	85.11%
Androgen receptor binding	+	0.5877	58.77%
Thyroid receptor binding	+	0.5452	54.52%
Glucocorticoid receptor binding	+	0.6539	65.39%
Aromatase binding	+	0.5527	55.27%
PPAR gamma	+	0.7216	72.16%
Honey bee toxicity	-	0.7694	76.94%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7349	73.49%
Fish aquatic toxicity	+	0.8517	85.17%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.39%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.01%	94.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.94%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.81%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.37%	98.95%
CHEMBL220	P22303	Acetylcholinesterase	94.01%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.68%	89.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.88%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.55%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.44%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.12%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.67%	95.89%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.13%	97.36%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	85.32%	95.78%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.23%	92.94%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.07%	95.83%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.76%	96.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.27%	96.77%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.27%	96.21%
CHEMBL3401	O75469	Pregnane X receptor	81.75%	94.73%
CHEMBL4208	P20618	Proteasome component C5	81.27%	90.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.79%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.70%	94.45%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.18%	97.14%

Plants that contains it

• Aquilaria sinensis
• Lethedon tannensis

Cross-Links

• PubChem: 10394124
• NPASS: NPC284277
• LOTUS: LTS0115039
• wikiData: Q105196751