4,2'-Dihydroxychalcone 4-glucoside

Details

• Internal ID: 3b3a91db-7fcf-4d34-807e-fdd7cee72546
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides
• IUPAC Name: (E)-1-(2-hydroxyphenyl)-3-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-en-1-one
• SMILES (Canonical): C1=CC=C(C(=C1)C(=O)C=CC2=CC=C(C=C2)OC3C(C(C(C(O3)CO)O)O)O)O
• SMILES (Isomeric): C1=CC=C(C(=C1)C(=O)/C=C/C2=CC=C(C=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O
• InChI: InChI=1S/C21H22O8/c22-11-17-18(25)19(26)20(27)21(29-17)28-13-8-5-12(6-9-13)7-10-16(24)14-3-1-2-4-15(14)23/h1-10,17-23,25-27H,11H2/b10-7+/t17-,18-,19+,20-,21-/m1/s1
• InChI Key: HKSOEGFPZGFKTM-WXHGGZEVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₈
• Molecular Weight: 402.40 g/mol
• Exact Mass: 402.13146766 g/mol
• Topological Polar Surface Area (TPSA): 137.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 0.47
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

• LMPK12120190

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6182	61.82%
Caco-2	-	0.8912	89.12%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6013	60.13%
OATP2B1 inhibitior	-	0.5690	56.90%
OATP1B1 inhibitior	+	0.9284	92.84%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5801	58.01%
P-glycoprotein inhibitior	-	0.7261	72.61%
P-glycoprotein substrate	-	0.9445	94.45%
CYP3A4 substrate	+	0.5297	52.97%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8653	86.53%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.8632	86.32%
CYP2C19 inhibition	-	0.8903	89.03%
CYP2D6 inhibition	-	0.9150	91.50%
CYP1A2 inhibition	-	0.9266	92.66%
CYP2C8 inhibition	+	0.6127	61.27%
CYP inhibitory promiscuity	-	0.6278	62.78%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7420	74.20%
Eye corrosion	-	0.9936	99.36%
Eye irritation	-	0.8993	89.93%
Skin irritation	-	0.8211	82.11%
Skin corrosion	-	0.9659	96.59%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6109	61.09%
Micronuclear	+	0.5633	56.33%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.7646	76.46%
Respiratory toxicity	-	0.6889	68.89%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.7167	71.67%
Acute Oral Toxicity (c)	III	0.6845	68.45%
Estrogen receptor binding	-	0.5354	53.54%
Androgen receptor binding	+	0.6508	65.08%
Thyroid receptor binding	+	0.5275	52.75%
Glucocorticoid receptor binding	-	0.6260	62.60%
Aromatase binding	+	0.5575	55.75%
PPAR gamma	+	0.8125	81.25%
Honey bee toxicity	-	0.7875	78.75%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	+	0.9057	90.57%

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	99.29%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.17%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.17%	95.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	90.92%	95.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.18%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.93%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.90%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.84%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	88.40%	94.73%
CHEMBL2581	P07339	Cathepsin D	85.91%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.34%	89.00%
CHEMBL4208	P20618	Proteasome component C5	81.49%	90.00%
CHEMBL3194	P02766	Transthyretin	80.74%	90.71%

Plants that contains it

• Justicia adhatoda

Cross-Links

• PubChem: 42607583
• LOTUS: LTS0245874
• wikiData: Q76534970