[5,6-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-7-yl] (2S,3S,4S,5R,6S)-3,4,5,6-tetrahydroxyoxane-2-carboxylate

Details

• Internal ID: 743fcc22-e62c-4b74-9fbe-f292a8f09e40
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 3-O-methylated flavonoids
• IUPAC Name: [5,6-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-7-yl] (2S,3S,4S,5R,6S)-3,4,5,6-tetrahydroxyoxane-2-carboxylate
• SMILES (Canonical): COC1=C(C=CC(=C1)C2=CC(=O)C3=C(C(=C(C=C3O2)OC(=O)C4C(C(C(C(O4)O)O)O)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C2=CC(=O)C3=C(C(=C(C=C3O2)OC(=O)[C@@H]4[C@H]([C@@H]([C@H]([C@H](O4)O)O)O)O)O)O)O
• InChI: InChI=1S/C22H20O13/c1-32-11-4-7(2-3-8(11)23)10-5-9(24)14-12(33-10)6-13(15(25)16(14)26)34-22(31)20-18(28)17(27)19(29)21(30)35-20/h2-6,17-21,23,25-30H,1H3/t17-,18-,19+,20-,21-/m0/s1
• InChI Key: SCUOFHFSRPWCKS-WHZJULEDSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₀O₁₃
• Molecular Weight: 492.40 g/mol
• Exact Mass: 492.09039069 g/mol
• Topological Polar Surface Area (TPSA): 213.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): -0.71
• H-Bond Acceptor: 13
• H-Bond Donor: 7
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7483	74.83%
Caco-2	-	0.9129	91.29%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6619	66.19%
OATP2B1 inhibitior	+	0.5952	59.52%
OATP1B1 inhibitior	+	0.8704	87.04%
OATP1B3 inhibitior	+	0.9857	98.57%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7076	70.76%
P-glycoprotein inhibitior	-	0.6354	63.54%
P-glycoprotein substrate	-	0.6154	61.54%
CYP3A4 substrate	+	0.6316	63.16%
CYP2C9 substrate	-	0.6356	63.56%
CYP2D6 substrate	-	0.8614	86.14%
CYP3A4 inhibition	-	0.7674	76.74%
CYP2C9 inhibition	-	0.8642	86.42%
CYP2C19 inhibition	-	0.8511	85.11%
CYP2D6 inhibition	-	0.9471	94.71%
CYP1A2 inhibition	-	0.6411	64.11%
CYP2C8 inhibition	+	0.8051	80.51%
CYP inhibitory promiscuity	-	0.7677	76.77%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5903	59.03%
Eye corrosion	-	0.9867	98.67%
Eye irritation	-	0.8815	88.15%
Skin irritation	-	0.6835	68.35%
Skin corrosion	-	0.9231	92.31%
Ames mutagenesis	-	0.5992	59.92%
Human Ether-a-go-go-Related Gene inhibition	-	0.6223	62.23%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.9291	92.91%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.9089	90.89%
Acute Oral Toxicity (c)	III	0.5786	57.86%
Estrogen receptor binding	+	0.8259	82.59%
Androgen receptor binding	+	0.7647	76.47%
Thyroid receptor binding	+	0.5236	52.36%
Glucocorticoid receptor binding	+	0.7133	71.33%
Aromatase binding	+	0.5434	54.34%
PPAR gamma	+	0.7284	72.84%
Honey bee toxicity	-	0.5524	55.24%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5549	55.49%
Fish aquatic toxicity	+	0.9235	92.35%

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	98.88%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.94%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.73%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.32%	89.00%
CHEMBL2581	P07339	Cathepsin D	95.26%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.99%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.50%	86.33%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.94%	90.71%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	87.73%	95.64%
CHEMBL3194	P02766	Transthyretin	87.12%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.93%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.95%	86.92%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.62%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.48%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	85.43%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.85%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.28%	95.89%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	83.62%	89.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.05%	97.14%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	81.01%	95.78%
CHEMBL1287628	Q9Y5S8	NADPH oxidase 1	80.34%	95.48%

Plants that contains it

• Gratiola officinalis

Cross-Links

• PubChem: 163039092
• LOTUS: LTS0168484
• wikiData: Q105250416