(2S,3R,4R,5S,6R)-2-[2-[(1S,2S)-2-[(2R,3R)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-5-yl]-1-hydroxy-2-(4-hydroxyphenyl)ethyl]-4,6-dihydroxyphenyl]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 6a1567fb-5112-468e-b043-3cc178c9a05d
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: (2S,3R,4R,5S,6R)-2-[2-[(1S,2S)-2-[(2R,3R)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-5-yl]-1-hydroxy-2-(4-hydroxyphenyl)ethyl]-4,6-dihydroxyphenyl]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C1=CC(=CC=C1C=CC2=C(C(=CC3=C2C(C(O3)C4=CC=C(C=C4)O)C5=CC(=CC(=C5)O)O)O)C(C6=CC=C(C=C6)O)C(C7=C(C(=CC(=C7)O)O)C8C(C(C(C(O8)CO)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1/C=C/C2=C(C(=CC3=C2[C@H]([C@@H](O3)C4=CC=C(C=C4)O)C5=CC(=CC(=C5)O)O)O)[C@H](C6=CC=C(C=C6)O)[C@@H](C7=C(C(=CC(=C7)O)O)[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O)O
• InChI: InChI=1S/C48H44O15/c49-21-37-44(59)45(60)46(61)48(63-37)41-33(18-31(55)19-34(41)56)43(58)38(23-4-10-27(51)11-5-23)40-32(14-3-22-1-8-26(50)9-2-22)42-36(20-35(40)57)62-47(24-6-12-28(52)13-7-24)39(42)25-15-29(53)17-30(54)16-25/h1-20,37-39,43-61H,21H2/b14-3+/t37-,38+,39-,43-,44-,45+,46-,47+,48+/m1/s1
• InChI Key: PKDHDJWDFKGODJ-OAUDXBQJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₄₄O₁₅
• Molecular Weight: 860.90 g/mol
• Exact Mass: 860.26802069 g/mol
• Topological Polar Surface Area (TPSA): 281.00 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 5.15
• H-Bond Acceptor: 15
• H-Bond Donor: 13
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7968	79.68%
Caco-2	-	0.9082	90.82%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.5879	58.79%
OATP2B1 inhibitior	-	0.5667	56.67%
OATP1B1 inhibitior	+	0.7785	77.85%
OATP1B3 inhibitior	+	0.9796	97.96%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7692	76.92%
P-glycoprotein inhibitior	+	0.6444	64.44%
P-glycoprotein substrate	-	0.5252	52.52%
CYP3A4 substrate	+	0.6558	65.58%
CYP2C9 substrate	-	0.6104	61.04%
CYP2D6 substrate	-	0.7359	73.59%
CYP3A4 inhibition	-	0.8486	84.86%
CYP2C9 inhibition	-	0.8260	82.60%
CYP2C19 inhibition	-	0.7769	77.69%
CYP2D6 inhibition	-	0.8634	86.34%
CYP1A2 inhibition	-	0.7567	75.67%
CYP2C8 inhibition	+	0.7656	76.56%
CYP inhibitory promiscuity	+	0.5780	57.80%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5645	56.45%
Eye corrosion	-	0.9924	99.24%
Eye irritation	-	0.8814	88.14%
Skin irritation	-	0.7687	76.87%
Skin corrosion	-	0.9431	94.31%
Ames mutagenesis	-	0.5998	59.98%
Human Ether-a-go-go-Related Gene inhibition	+	0.9095	90.95%
Micronuclear	+	0.6459	64.59%
Hepatotoxicity	-	0.7175	71.75%
skin sensitisation	-	0.8069	80.69%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.7397	73.97%
Acute Oral Toxicity (c)	III	0.4153	41.53%
Estrogen receptor binding	+	0.7634	76.34%
Androgen receptor binding	+	0.7146	71.46%
Thyroid receptor binding	+	0.6131	61.31%
Glucocorticoid receptor binding	-	0.5693	56.93%
Aromatase binding	-	0.5319	53.19%
PPAR gamma	+	0.7222	72.22%
Honey bee toxicity	-	0.6667	66.67%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.8467	84.67%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.98%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.87%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.71%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	92.86%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.66%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.45%	85.14%
CHEMBL2581	P07339	Cathepsin D	92.40%	98.95%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.33%	86.92%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.72%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.06%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.20%	95.56%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	89.90%	89.67%
CHEMBL3192	Q9BY41	Histone deacetylase 8	88.89%	93.99%
CHEMBL3194	P02766	Transthyretin	87.63%	90.71%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	85.70%	89.44%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.93%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.82%	99.17%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	83.82%	91.71%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	83.78%	85.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.11%	89.62%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.71%	100.00%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	80.50%	96.37%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.37%	95.83%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.37%	86.33%

Plants that contains it

• Hopea indica

Cross-Links

• PubChem: 51042328
• LOTUS: LTS0202082
• wikiData: Q105210340