5-[(2R,3S)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol

Details

• Internal ID: bf07c90b-846c-4ad2-ac35-68ba7707d33d
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: 5-[(2R,3S)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol
• SMILES (Canonical): C1=CC(=CC=C1C=CC2=C3C(C(OC3=CC(=C2)O)C4=CC=C(C=C4)O)C5=CC(=CC(=C5)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1/C=C/C2=C3[C@@H]([C@@H](OC3=CC(=C2)O)C4=CC=C(C=C4)O)C5=CC(=CC(=C5)O)O)O
• InChI: InChI=1S/C28H22O6/c29-20-7-2-16(3-8-20)1-4-18-11-24(33)15-25-26(18)27(19-12-22(31)14-23(32)13-19)28(34-25)17-5-9-21(30)10-6-17/h1-15,27-33H/b4-1+/t27-,28-/m0/s1
• InChI Key: FQWLMRXWKZGLFI-PAKBJIOWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₂₂O₆
• Molecular Weight: 454.50 g/mol
• Exact Mass: 454.14163842 g/mol
• Topological Polar Surface Area (TPSA): 110.00 Ų
• XlogP: 5.40
• Atomic LogP (AlogP): 5.65
• H-Bond Acceptor: 6
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

• 5-[(2R,3S)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol
• 5-{(2R,3S)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl}benzene-1,3-diol
• CHEBI:76143
• AKOS040736044
• Q27145781

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9898	98.98%
Caco-2	-	0.7883	78.83%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.4875	48.75%
OATP2B1 inhibitior	+	0.5645	56.45%
OATP1B1 inhibitior	+	0.7618	76.18%
OATP1B3 inhibitior	-	0.2406	24.06%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7425	74.25%
P-glycoprotein inhibitior	-	0.4509	45.09%
P-glycoprotein substrate	-	0.9067	90.67%
CYP3A4 substrate	-	0.5114	51.14%
CYP2C9 substrate	+	0.6202	62.02%
CYP2D6 substrate	+	0.3681	36.81%
CYP3A4 inhibition	+	0.5901	59.01%
CYP2C9 inhibition	+	0.9088	90.88%
CYP2C19 inhibition	+	0.8471	84.71%
CYP2D6 inhibition	-	0.8727	87.27%
CYP1A2 inhibition	+	0.9282	92.82%
CYP2C8 inhibition	+	0.7203	72.03%
CYP inhibitory promiscuity	+	0.9725	97.25%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Danger	0.3539	35.39%
Eye corrosion	-	0.9885	98.85%
Eye irritation	+	0.6988	69.88%
Skin irritation	+	0.5230	52.30%
Skin corrosion	-	0.9281	92.81%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7668	76.68%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	-	0.6104	61.04%
skin sensitisation	-	0.6951	69.51%
Respiratory toxicity	-	0.6333	63.33%
Reproductive toxicity	-	0.5000	50.00%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	+	0.5498	54.98%
Acute Oral Toxicity (c)	III	0.4075	40.75%
Estrogen receptor binding	+	0.6454	64.54%
Androgen receptor binding	+	0.8361	83.61%
Thyroid receptor binding	+	0.7223	72.23%
Glucocorticoid receptor binding	+	0.7239	72.39%
Aromatase binding	+	0.6474	64.74%
PPAR gamma	+	0.8238	82.38%
Honey bee toxicity	-	0.8502	85.02%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9844	98.44%

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	98.34%	91.11%
CHEMBL3194	P02766	Transthyretin	95.21%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.33%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.10%	95.56%
CHEMBL242	Q92731	Estrogen receptor beta	88.61%	98.35%
CHEMBL1951	P21397	Monoamine oxidase A	87.09%	91.49%
CHEMBL4040	P28482	MAP kinase ERK2	85.85%	83.82%
CHEMBL3401	O75469	Pregnane X receptor	85.84%	94.73%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.03%	96.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	84.88%	93.99%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.25%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.87%	86.33%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	83.15%	89.67%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.38%	94.45%

Plants that contains it

• Acacia adunca
• Adiantum philippense
• Aldama incana
• Annona cornifolia
• Aristeguietia glutinosa
• Artemisia pedemontana subsp. assoana
• Astragalus sempervirens
• Calostephane divaricata
• Caragana aurantiaca
• Chaenomeles sinensis
• Cinnamosma macrocarpa
• Dumortiera hirsuta
• Echeveria secunda
• Eucalyptus melliodora
• Gnetum latifolium
• Goniothalamus malayanus
• Hedysarum inundatum
• Hypericum laricifolium
• Ipomoea digitata
• Lepisorus ussuriensis
• Leptinella filicula
• Leucosceptrum canum
• Lysimachia mauritiana
• Marrubium anisodon
• Maytenus imbricata
• Naucleopsis ternstroemiiflora
• Ocotea pittieri
• Packera toluccana
• Pastinaca sativa
• Peltostigma guatemalense
• Piper caninum
• Polyalthia evecta
• Premna odorata
• Rauvolfia vomitoria
• Rhodanthe chlorocephala subsp. rosea
• Rumex maritimus
• Salvia syriaca
• Scutellaria amoena
• Sideritis chamaedryfolia
• Solanum laxum
• Swertia franchetiana
• Vaccinium oxycoccos
• Vatica affinis
• Vatica rassak
• Vitis vinifera
• Wikstroemia retusa
• Zanthoxylum tetraspermum

Cross-Links

• PubChem: 5315234
• NPASS: NPC201170
• LOTUS: LTS0101887
• wikiData: Q27145781