2-(4-Hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

Details

• Internal ID: 96cb96a8-5b76-4996-94ef-e06c29e16637
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Flavan-3-ols
• IUPAC Name: 2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
• SMILES (Canonical): C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC=C(C=C3)O)O
• SMILES (Isomeric): C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC=C(C=C3)O)O
• InChI: InChI=1S/C15H14O5/c16-9-3-1-8(2-4-9)15-13(19)7-11-12(18)5-10(17)6-14(11)20-15/h1-6,13,15-19H,7H2
• InChI Key: RSYUFYQTACJFML-UHFFFAOYSA-N
• Popularity: 12 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₄O₅
• Molecular Weight: 274.27 g/mol
• Exact Mass: 274.08412354 g/mol
• Topological Polar Surface Area (TPSA): 90.20 Ų
• XlogP: 0.70

Synonyms

• 2-(4-Hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
• (+)-Afzelechin ;NSC 135065
• Oc1cc(O)cc2OC(C(O)Cc12)c3ccc(O)cc3
• Afzelechin, (+)-
• Flavan-3-ols + 3O
• (-)-epi-Afzelechin;Epiafzelechin, (-)-; epi-Afzelechin
• 3,4',5,7-tetrahydroxyflavan
• 3,5,7-Flavantetrol (+)-
• CHEMBL1326092
• SCHEMBL10405656
• 3,5,7-Flaventetrol, (+)-
• CHEBI:181768
• (+)-3,4',5,7-Flaventetrol
• DTXSID301189517
• 3,4',5,7-Flavantetrol (+)-
• NSC135065
• NCGC00095516-01
• 3,4-Dihydro-2-(4-hydroxyphenyl)-2H-1-benzopyran-3,5,7-triol
• (2R,3S)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
• 490-61-9

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
CHEMBL340	P08684	Cytochrome P450 3A4	12589.3 nM; 12589.3 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.98%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	93.71%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.00%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.97%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.32%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.92%	95.56%
CHEMBL2581	P07339	Cathepsin D	84.77%	98.95%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	83.96%	93.40%
CHEMBL3194	P02766	Transthyretin	83.51%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	81.47%	94.73%
CHEMBL242	Q92731	Estrogen receptor beta	81.37%	98.35%
CHEMBL2535	P11166	Glucose transporter	81.10%	98.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.18%	94.45%

Plants that contains it

• Actinidia chinensis
• Artocarpus lacucha
• Bergenia pacumbis
• Calophyllum apetalum
• Camellia sinensis
• Cassia fistula
• Cassipourea gummiflua
• Celastrus orbiculatus
• Daphne holosericea
• Dicranopteris pedata
• Kandelia candel
• Phyllanthus emblica
• Prunus persica
• Rhizophora stylosa
• Senegalia catechu
• Typha capensis
• Wisteria floribunda
• Ziziphus jujuba

Cross-Links

• PubChem: 282014
• NPASS: NPC167571
• ChEMBL: CHEMBL1326092
• LOTUS: LTS0039714
• wikiData: Q105244978