CID 12304094

Details

• Internal ID: 24deeb1e-4884-4507-bb1a-df9f22b355c7
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): C1=CC(=CC=C1C2=CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C2=CC(=O)C3=C(C=C(C=C3O2)O[C@H]4[C@@H]([C@@H]([C@H]([C@H](O4)CO)O)O)O)O)O
• InChI: InChI=1S/C21H20O10/c22-8-16-18(26)19(27)20(28)21(31-16)29-11-5-12(24)17-13(25)7-14(30-15(17)6-11)9-1-3-10(23)4-2-9/h1-7,16,18-24,26-28H,8H2/t16-,18+,19-,20-,21-/m1/s1
• InChI Key: KMOUJOKENFFTPU-RSRIQPTJSA-N
• Popularity: 134 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: -0.10
• Atomic LogP (AlogP): 0.05
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

• 5-Hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5548	55.48%
Caco-2	-	0.9236	92.36%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6433	64.33%
OATP2B1 inhibitior	-	0.5298	52.98%
OATP1B1 inhibitior	+	0.9514	95.14%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.4704	47.04%
P-glycoprotein inhibitior	-	0.8532	85.32%
P-glycoprotein substrate	-	0.8587	85.87%
CYP3A4 substrate	+	0.5537	55.37%
CYP2C9 substrate	-	0.6762	67.62%
CYP2D6 substrate	-	0.8575	85.75%
CYP3A4 inhibition	-	0.9192	91.92%
CYP2C9 inhibition	-	0.9435	94.35%
CYP2C19 inhibition	-	0.9426	94.26%
CYP2D6 inhibition	-	0.9501	95.01%
CYP1A2 inhibition	-	0.9203	92.03%
CYP2C8 inhibition	+	0.6928	69.28%
CYP inhibitory promiscuity	-	0.7833	78.33%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6688	66.88%
Eye corrosion	-	0.9926	99.26%
Eye irritation	-	0.8716	87.16%
Skin irritation	-	0.8111	81.11%
Skin corrosion	-	0.9715	97.15%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5745	57.45%
Micronuclear	+	0.6133	61.33%
Hepatotoxicity	-	0.8696	86.96%
skin sensitisation	-	0.9256	92.56%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.7945	79.45%
Acute Oral Toxicity (c)	III	0.4522	45.22%
Estrogen receptor binding	+	0.6847	68.47%
Androgen receptor binding	+	0.7434	74.34%
Thyroid receptor binding	+	0.5224	52.24%
Glucocorticoid receptor binding	+	0.5840	58.40%
Aromatase binding	+	0.6524	65.24%
PPAR gamma	+	0.8225	82.25%
Honey bee toxicity	-	0.6936	69.36%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6450	64.50%
Fish aquatic toxicity	+	0.7773	77.73%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1825	P01375	TNF-alpha	200 nM	Kd	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.32%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.74%	94.00%
CHEMBL2581	P07339	Cathepsin D	95.39%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.51%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.74%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.90%	86.92%
CHEMBL3194	P02766	Transthyretin	91.80%	90.71%
CHEMBL1951	P21397	Monoamine oxidase A	89.31%	91.49%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.73%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	88.56%	94.73%
CHEMBL242	Q92731	Estrogen receptor beta	87.75%	98.35%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	87.54%	95.78%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.44%	94.45%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.10%	96.21%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.28%	86.33%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	84.61%	83.57%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.41%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.50%	95.89%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.44%	91.71%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.74%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.42%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.32%	85.14%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.77%	95.89%

Plants that contains it

• Apium graveolens
• Euphorbia hyssopifolia
• Helichrysum arenarium
• Itoa orientalis
• Stachys schtschegleevii

Cross-Links

• PubChem: 12304094
• LOTUS: LTS0180546
• wikiData: Q104399660