(2S)-5-hydroxy-2-[2-hydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-7,8-dimethoxy-2,3-dihydrochromen-4-one

Details

• Internal ID: e4c9b206-ac7d-4562-9f4e-9edb50fa433e
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 8-O-methylated flavonoids
• IUPAC Name: (2S)-5-hydroxy-2-[2-hydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-7,8-dimethoxy-2,3-dihydrochromen-4-one
• SMILES (Canonical): COC1=C(C2=C(C(=O)CC(O2)C3=C(C=CC=C3OC4C(C(C(C(O4)CO)O)O)O)O)C(=C1)O)OC
• SMILES (Isomeric): COC1=C(C2=C(C(=O)C[C@H](O2)C3=C(C=CC=C3O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)C(=C1)O)OC
• InChI: InChI=1S/C23H26O12/c1-31-14-7-11(27)16-10(26)6-13(33-22(16)21(14)32-2)17-9(25)4-3-5-12(17)34-23-20(30)19(29)18(28)15(8-24)35-23/h3-5,7,13,15,18-20,23-25,27-30H,6,8H2,1-2H3/t13-,15+,18+,19-,20+,23+/m0/s1
• InChI Key: JWFFWURECCTPGO-DYRYEQCVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₆O₁₂
• Molecular Weight: 494.40 g/mol
• Exact Mass: 494.14242626 g/mol
• Topological Polar Surface Area (TPSA): 185.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 0.00
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5074	50.74%
Caco-2	-	0.8058	80.58%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6238	62.38%
OATP2B1 inhibitior	-	0.8491	84.91%
OATP1B1 inhibitior	+	0.8969	89.69%
OATP1B3 inhibitior	+	0.9678	96.78%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.6983	69.83%
P-glycoprotein inhibitior	-	0.5947	59.47%
P-glycoprotein substrate	-	0.7267	72.67%
CYP3A4 substrate	+	0.6328	63.28%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8374	83.74%
CYP3A4 inhibition	-	0.8862	88.62%
CYP2C9 inhibition	-	0.9258	92.58%
CYP2C19 inhibition	-	0.9329	93.29%
CYP2D6 inhibition	-	0.9457	94.57%
CYP1A2 inhibition	-	0.9089	90.89%
CYP2C8 inhibition	+	0.4734	47.34%
CYP inhibitory promiscuity	-	0.7195	71.95%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7238	72.38%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9021	90.21%
Skin irritation	-	0.8305	83.05%
Skin corrosion	-	0.9609	96.09%
Ames mutagenesis	+	0.5063	50.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.5517	55.17%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	-	0.6301	63.01%
skin sensitisation	-	0.9389	93.89%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.6315	63.15%
Acute Oral Toxicity (c)	III	0.6799	67.99%
Estrogen receptor binding	+	0.7251	72.51%
Androgen receptor binding	+	0.5558	55.58%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.5980	59.80%
Aromatase binding	-	0.5382	53.82%
PPAR gamma	+	0.5578	55.78%
Honey bee toxicity	-	0.8001	80.01%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.7522	75.22%

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	99.02%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.63%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.83%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.43%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.33%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.71%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.91%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.31%	89.00%
CHEMBL2535	P11166	Glucose transporter	88.26%	98.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.18%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.93%	85.14%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.93%	96.21%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	85.04%	94.03%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.85%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.31%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	83.40%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.15%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.72%	92.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.43%	99.23%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.16%	99.15%

Plants that contains it

• Scutellaria indica

Cross-Links

• PubChem: 118727139
• LOTUS: LTS0181589
• wikiData: Q105136122