2-(3,4-dihydroxyphenyl)-5,6-dihydroxy-7-methoxy-3-[(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one

Details

• Internal ID: 3a877ced-6b79-440c-9385-9e512565289e
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-5,6-dihydroxy-7-methoxy-3-[(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): COC1=C(C(=C2C(=C1)OC(=C(C2=O)OC3C(C(C(C(O3)CO)O)O)O)C4=CC(=C(C=C4)O)O)O)O
• SMILES (Isomeric): COC1=C(C(=C2C(=C1)OC(=C(C2=O)O[C@H]3[C@H]([C@H]([C@H]([C@@H](O3)CO)O)O)O)C4=CC(=C(C=C4)O)O)O)O
• InChI: InChI=1S/C22H22O13/c1-32-11-5-10-13(16(28)14(11)26)17(29)21(20(33-10)7-2-3-8(24)9(25)4-7)35-22-19(31)18(30)15(27)12(6-23)34-22/h2-5,12,15,18-19,22-28,30-31H,6H2,1H3/t12-,15-,18-,19-,22-/m0/s1
• InChI Key: AGKJZAUTPQSZRO-IJHVHCBMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₂O₁₃
• Molecular Weight: 494.40 g/mol
• Exact Mass: 494.10604075 g/mol
• Topological Polar Surface Area (TPSA): 216.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): -0.53
• H-Bond Acceptor: 13
• H-Bond Donor: 8
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4855	48.55%
Caco-2	-	0.8817	88.17%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6190	61.90%
OATP2B1 inhibitior	+	0.5885	58.85%
OATP1B1 inhibitior	+	0.9308	93.08%
OATP1B3 inhibitior	+	0.9740	97.40%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.6979	69.79%
P-glycoprotein inhibitior	-	0.5928	59.28%
P-glycoprotein substrate	-	0.6199	61.99%
CYP3A4 substrate	+	0.6293	62.93%
CYP2C9 substrate	-	0.8415	84.15%
CYP2D6 substrate	-	0.8515	85.15%
CYP3A4 inhibition	-	0.9108	91.08%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9173	91.73%
CYP2D6 inhibition	-	0.9514	95.14%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.8272	82.72%
CYP inhibitory promiscuity	-	0.7292	72.92%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6890	68.90%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.8316	83.16%
Skin irritation	-	0.8153	81.53%
Skin corrosion	-	0.9600	96.00%
Ames mutagenesis	+	0.5936	59.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.4141	41.41%
Micronuclear	+	0.6633	66.33%
Hepatotoxicity	-	0.6448	64.48%
skin sensitisation	-	0.9373	93.73%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.9335	93.35%
Acute Oral Toxicity (c)	III	0.6624	66.24%
Estrogen receptor binding	+	0.7628	76.28%
Androgen receptor binding	+	0.6969	69.69%
Thyroid receptor binding	-	0.5145	51.45%
Glucocorticoid receptor binding	+	0.7139	71.39%
Aromatase binding	+	0.5422	54.22%
PPAR gamma	+	0.6456	64.56%
Honey bee toxicity	-	0.7176	71.76%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5749	57.49%
Fish aquatic toxicity	+	0.7079	70.79%

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	99.49%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.72%	85.14%
CHEMBL2581	P07339	Cathepsin D	97.04%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.70%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.95%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.83%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.20%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.14%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.29%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	88.37%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.75%	94.45%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	85.72%	95.64%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.30%	86.92%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.54%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.33%	92.62%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.91%	90.71%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.21%	96.21%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.18%	95.89%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	81.04%	95.53%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.57%	96.00%

Plants that contains it

• Paepalanthus latipes

Cross-Links

• PubChem: 163057401
• LOTUS: LTS0056593
• wikiData: Q104911851