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

Details

• Internal ID: 506d761e-cbe8-465f-85ac-40c5ce188b6a
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(3R,4S,5S,6R)-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)OC4[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?/m1/s1
• InChI Key: OVSQVDMCBVZWGM-CAWYGJOUSA-N
• Popularity: 128 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

Synonyms

• 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SCHEMBL561412
• DTXSID3041110
• AKOS015965147
• 3',4',5,7-Tetrahydroxy-3beta-(D-glucopyranosyloxy)flavone
• 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

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

• Abelmoschus manihot
• Apocynum venetum
• Artemisia capillaris
• Eleutherococcus nodiflorus
• Epimedium brevicornu
• Epimedium grandiflorum
• Epimedium koreanum
• Epimedium pubescens
• Epimedium sagittatum
• Epimedium sempervirens
• Epimedium wushanense
• Erodium stephanianum
• Forsythia suspensa
• Forsythia viridissima
• Geranium carolinianum
• Geranium thunbergii
• Geranium wilfordii
• Grona styracifolia
• Houttuynia cordata
• Hypericum perforatum
• Lysimachia christinae
• Morus alba
• Nelumbo nucifera
• Pyrola japonica
• Reynoutria multiflora
• Sanguisorba officinalis
• Taraxacum coreanum
• Taraxacum mongolicum
• Taraxacum officinale
• Taraxacum platycarpum
• Taraxacum sinicum

Cross-Links

• PubChem: 11557027
• NPASS: NPC135088