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

Details

• Internal ID: 2f0b1a47-d5d2-492b-b135-2ef6542bb6ec
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)CO)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O[C@H]4[C@H]([C@@H]([C@H]([C@@H](O4)CO)O)O)O)O)O
• InChI: InChI=1S/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/t13-,15-,17+,18-,21-/m0/s1
• InChI Key: OVSQVDMCBVZWGM-YSBXYMAXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₁₂
• Molecular Weight: 464.40 g/mol
• Exact Mass: 464.09547607 g/mol
• Topological Polar Surface Area (TPSA): 207.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): -0.54
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5116	51.16%
Caco-2	-	0.9010	90.10%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6068	60.68%
OATP2B1 inhibitior	+	0.5930	59.30%
OATP1B1 inhibitior	+	0.9271	92.71%
OATP1B3 inhibitior	+	0.9265	92.65%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.6488	64.88%
P-glycoprotein inhibitior	-	0.6240	62.40%
P-glycoprotein substrate	-	0.8086	80.86%
CYP3A4 substrate	+	0.6155	61.55%
CYP2C9 substrate	-	0.6709	67.09%
CYP2D6 substrate	-	0.8582	85.82%
CYP3A4 inhibition	-	0.9193	91.93%
CYP2C9 inhibition	-	0.9296	92.96%
CYP2C19 inhibition	-	0.9289	92.89%
CYP2D6 inhibition	-	0.9513	95.13%
CYP1A2 inhibition	-	0.9084	90.84%
CYP2C8 inhibition	+	0.8882	88.82%
CYP inhibitory promiscuity	-	0.7728	77.28%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7144	71.44%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.7321	73.21%
Skin irritation	-	0.8036	80.36%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	+	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.5196	51.96%
skin sensitisation	-	0.9122	91.22%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.7975	79.75%
Acute Oral Toxicity (c)	III	0.4045	40.45%
Estrogen receptor binding	+	0.7470	74.70%
Androgen receptor binding	+	0.7633	76.33%
Thyroid receptor binding	-	0.5202	52.02%
Glucocorticoid receptor binding	+	0.7040	70.40%
Aromatase binding	+	0.5913	59.13%
PPAR gamma	+	0.7022	70.22%
Honey bee toxicity	-	0.7417	74.17%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6250	62.50%
Fish aquatic toxicity	+	0.8218	82.18%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL205	P00918	Carbonic anhydrase II	410 nM	Ki	via Super-PRED
CHEMBL3729	P22748	Carbonic anhydrase IV	75.7 nM	Ki	via Super-PRED
CHEMBL2326	P43166	Carbonic anhydrase VII	3.8 nM	Ki	via Super-PRED
CHEMBL3242	O43570	Carbonic anhydrase XII	52.1 nM	Ki	via Super-PRED
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	950 nM	IC50	via Super-PRED
CHEMBL1293232	Q16637	Survival motor neuron protein	446.7 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.54%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.43%	89.00%
CHEMBL2581	P07339	Cathepsin D	95.28%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.96%	99.15%
CHEMBL1951	P21397	Monoamine oxidase A	92.68%	91.49%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.26%	94.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	90.17%	95.64%
CHEMBL3401	O75469	Pregnane X receptor	89.84%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.58%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.11%	86.33%
CHEMBL3194	P02766	Transthyretin	88.77%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.32%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.77%	86.92%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.50%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.84%	95.56%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	84.25%	95.78%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.96%	97.09%

Plants that contains it

• Centaurea depressa
• Gaillardia aristata
• Hymenoxys hoopesii
• Myrsine africana
• Viburnum dilatatum

Cross-Links

• PubChem: 5318574
• NPASS: NPC145571
• LOTUS: LTS0102788
• wikiData: Q105201331