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

Details

• Internal ID: d284121a-0db4-4374-ad65-352866b5ce4e
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 3-O-methylated flavonoids
• IUPAC Name: [5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-7-yl] (2S,3S,4S,5R,6R)-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
• 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
• InChI: InChI=1S/C22H20O12/c1-31-14-4-8(2-3-10(14)23)13-7-12(25)16-11(24)5-9(6-15(16)33-13)32-22(30)20-18(27)17(26)19(28)21(29)34-20/h2-7,17-21,23-24,26-29H,1H3/t17-,18-,19+,20-,21+/m0/s1
• InChI Key: XEBPNCWIPRFZFV-JRSUCEMESA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₀O₁₂
• Molecular Weight: 476.40 g/mol
• Exact Mass: 476.09547607 g/mol
• Topological Polar Surface Area (TPSA): 192.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): -0.41
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• 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	-	0.8871	88.71%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6619	66.19%
OATP2B1 inhibitior	+	0.5904	59.04%
OATP1B1 inhibitior	+	0.9007	90.07%
OATP1B3 inhibitior	+	0.9857	98.57%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6410	64.10%
P-glycoprotein inhibitior	-	0.5859	58.59%
P-glycoprotein substrate	-	0.6809	68.09%
CYP3A4 substrate	+	0.6174	61.74%
CYP2C9 substrate	-	0.6338	63.38%
CYP2D6 substrate	-	0.8619	86.19%
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	+	0.8157	81.57%
CYP inhibitory promiscuity	-	0.7677	76.77%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5903	59.03%
Eye corrosion	-	0.9867	98.67%
Eye irritation	-	0.8916	89.16%
Skin irritation	-	0.6835	68.35%
Skin corrosion	-	0.9231	92.31%
Ames mutagenesis	-	0.5892	58.92%
Human Ether-a-go-go-Related Gene inhibition	-	0.5943	59.43%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	-	0.7907	79.07%
skin sensitisation	-	0.9291	92.91%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.7690	76.90%
Acute Oral Toxicity (c)	III	0.5786	57.86%
Estrogen receptor binding	+	0.8381	83.81%
Androgen receptor binding	+	0.7365	73.65%
Thyroid receptor binding	+	0.5148	51.48%
Glucocorticoid receptor binding	+	0.7631	76.31%
Aromatase binding	+	0.5771	57.71%
PPAR gamma	+	0.7258	72.58%
Honey bee toxicity	-	0.5787	57.87%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6249	62.49%
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	98.50%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.45%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.90%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.40%	85.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.30%	99.15%
CHEMBL2581	P07339	Cathepsin D	92.15%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.47%	95.56%
CHEMBL3194	P02766	Transthyretin	91.21%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.45%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.50%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.21%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.11%	90.71%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	87.83%	95.78%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.83%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	85.91%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.60%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.31%	96.09%
CHEMBL3438	Q05513	Protein kinase C zeta	83.95%	88.48%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.63%	97.14%
CHEMBL1287628	Q9Y5S8	NADPH oxidase 1	83.12%	95.48%
CHEMBL2179	P04062	Beta-glucocerebrosidase	81.07%	85.31%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.33%	95.89%

Plants that contains it

• Gratiola officinalis
• Rosa rugosa

Cross-Links

• PubChem: 162910162
• LOTUS: LTS0117437
• wikiData: Q104981186