7-[(2S,3R,4R,5R)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-yl]oxy-5-hydroxy-3-(4-hydroxyphenyl)chromen-4-one

Details

• Internal ID: 79c5b91c-77f5-4223-a70c-c8b4ccf9ef01
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavonoid O-glycosides
• IUPAC Name: 7-[(2S,3R,4R,5R)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-yl]oxy-5-hydroxy-3-(4-hydroxyphenyl)chromen-4-one
• SMILES (Canonical): C1=CC(=CC=C1C2=COC3=CC(=CC(=C3C2=O)O)OC4C(C(C(O4)C(CO)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C2=COC3=CC(=CC(=C3C2=O)O)O[C@H]4[C@@H]([C@H]([C@H](O4)[C@@H](CO)O)O)O)O
• InChI: InChI=1S/C21H20O10/c22-7-14(25)20-18(27)19(28)21(31-20)30-11-5-13(24)16-15(6-11)29-8-12(17(16)26)9-1-3-10(23)4-2-9/h1-6,8,14,18-25,27-28H,7H2/t14-,18-,19-,20-,21-/m1/s1
• InChI Key: UGXMGGSZJRLQAB-QUMCUXDJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₁₀
• Molecular Weight: 432.40 g/mol
• Exact Mass: 432.10564683 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 0.05
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6907	69.07%
Caco-2	-	0.9224	92.24%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6366	63.66%
OATP2B1 inhibitior	+	0.5857	58.57%
OATP1B1 inhibitior	+	0.9486	94.86%
OATP1B3 inhibitior	+	0.9023	90.23%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.5605	56.05%
P-glycoprotein inhibitior	-	0.7430	74.30%
P-glycoprotein substrate	-	0.8010	80.10%
CYP3A4 substrate	+	0.6265	62.65%
CYP2C9 substrate	-	0.6762	67.62%
CYP2D6 substrate	-	0.8575	85.75%
CYP3A4 inhibition	-	0.7521	75.21%
CYP2C9 inhibition	-	0.8969	89.69%
CYP2C19 inhibition	-	0.9036	90.36%
CYP2D6 inhibition	-	0.8355	83.55%
CYP1A2 inhibition	-	0.8729	87.29%
CYP2C8 inhibition	+	0.6814	68.14%
CYP inhibitory promiscuity	-	0.6453	64.53%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6205	62.05%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.8349	83.49%
Skin irritation	-	0.7918	79.18%
Skin corrosion	-	0.9586	95.86%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5878	58.78%
Micronuclear	+	0.6833	68.33%
Hepatotoxicity	-	0.6446	64.46%
skin sensitisation	-	0.8682	86.82%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.4746	47.46%
Acute Oral Toxicity (c)	III	0.5569	55.69%
Estrogen receptor binding	+	0.6919	69.19%
Androgen receptor binding	+	0.7375	73.75%
Thyroid receptor binding	+	0.5683	56.83%
Glucocorticoid receptor binding	+	0.5521	55.21%
Aromatase binding	+	0.5774	57.74%
PPAR gamma	+	0.7876	78.76%
Honey bee toxicity	-	0.7653	76.53%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.8004	80.04%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.86%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.64%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.86%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.65%	99.15%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	89.68%	90.71%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.48%	86.92%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.19%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.75%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.66%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.71%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.62%	97.09%
CHEMBL242	Q92731	Estrogen receptor beta	87.40%	98.35%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	87.27%	91.71%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.15%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.00%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.99%	95.56%
CHEMBL3922	P50579	Methionine aminopeptidase 2	83.93%	97.28%
CHEMBL3194	P02766	Transthyretin	82.54%	90.71%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.38%	95.78%
CHEMBL4208	P20618	Proteasome component C5	81.71%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.54%	94.45%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.16%	96.21%

Plants that contains it

• Thermopsis dolichocarpa

Cross-Links

• PubChem: 162972772
• LOTUS: LTS0033749
• wikiData: Q105272628