5-[(2S,3R,4S,5R)-4-[(2S,3S)-3-[(2R,3R)-3-(3,5-dihydroxyphenyl)-7-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-yl]-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-2,5-bis(4-hydroxyphenyl)oxolan-3-yl]benzene-1,3-diol

Details

• Internal ID: 62d4bc4b-a543-4eca-bacb-f0879e7543ea
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: 5-[(2S,3R,4S,5R)-4-[(2S,3S)-3-[(2R,3R)-3-(3,5-dihydroxyphenyl)-7-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-yl]-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-2,5-bis(4-hydroxyphenyl)oxolan-3-yl]benzene-1,3-diol
• SMILES (Canonical): C1=CC(=CC=C1C2C(C(C(O2)C3=CC=C(C=C3)O)C4=C5C(C(OC5=CC(=C4)O)C6=CC=C(C=C6)O)C7=CC8=C(C(=C7)O)OC(C8C9=CC(=CC(=C9)O)O)C1=CC=C(C=C1)O)C1=CC(=CC(=C1)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1[C@@H]2[C@H]([C@H]([C@@H](O2)C3=CC=C(C=C3)O)C4=C5[C@@H]([C@H](OC5=CC(=C4)O)C6=CC=C(C=C6)O)C7=CC8=C(C(=C7)O)O[C@H]([C@@H]8C9=CC(=CC(=C9)O)O)C1=CC=C(C=C1)O)C1=CC(=CC(=C1)O)O)O
• InChI: InChI=1S/C56H44O13/c57-34-9-1-27(2-10-34)52-47(31-17-38(61)23-39(62)18-31)44-21-33(22-45(66)56(44)69-52)48-50-43(25-42(65)26-46(50)67-53(48)28-3-11-35(58)12-4-28)51-49(32-19-40(63)24-41(64)20-32)54(29-5-13-36(59)14-6-29)68-55(51)30-7-15-37(60)16-8-30/h1-26,47-49,51-55,57-66H/t47-,48+,49+,51-,52+,53-,54-,55+/m1/s1
• InChI Key: INNCSLAJOWLWJY-DTHXJHJPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₆H₄₄O₁₃
• Molecular Weight: 924.90 g/mol
• Exact Mass: 924.27819145 g/mol
• Topological Polar Surface Area (TPSA): 230.00 Ų
• XlogP: 8.80
• Atomic LogP (AlogP): 10.65
• H-Bond Acceptor: 13
• H-Bond Donor: 10
• Rotatable Bonds: 8

Synonyms

• SCHEMBL30011042

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9720	97.20%
Caco-2	-	0.8757	87.57%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6025	60.25%
OATP2B1 inhibitior	-	0.7058	70.58%
OATP1B1 inhibitior	+	0.7997	79.97%
OATP1B3 inhibitior	-	0.3317	33.17%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.7085	70.85%
P-glycoprotein inhibitior	+	0.7199	71.99%
P-glycoprotein substrate	-	0.7972	79.72%
CYP3A4 substrate	+	0.5690	56.90%
CYP2C9 substrate	-	0.7850	78.50%
CYP2D6 substrate	+	0.4564	45.64%
CYP3A4 inhibition	+	0.5389	53.89%
CYP2C9 inhibition	+	0.8857	88.57%
CYP2C19 inhibition	+	0.6764	67.64%
CYP2D6 inhibition	-	0.7943	79.43%
CYP1A2 inhibition	+	0.8759	87.59%
CYP2C8 inhibition	+	0.6825	68.25%
CYP inhibitory promiscuity	+	0.9107	91.07%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.4216	42.16%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.8411	84.11%
Skin irritation	+	0.5479	54.79%
Skin corrosion	-	0.9306	93.06%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8418	84.18%
Micronuclear	+	0.8300	83.00%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.7265	72.65%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	+	0.5736	57.36%
Acute Oral Toxicity (c)	III	0.4482	44.82%
Estrogen receptor binding	+	0.7440	74.40%
Androgen receptor binding	+	0.7834	78.34%
Thyroid receptor binding	+	0.6483	64.83%
Glucocorticoid receptor binding	+	0.6137	61.37%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.7227	72.27%
Honey bee toxicity	-	0.8016	80.16%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.6500	65.00%
Fish aquatic toxicity	+	0.9342	93.42%

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	98.84%	91.11%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.28%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.73%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	88.65%	94.73%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	88.63%	93.10%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	88.48%	93.40%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.41%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.35%	94.45%
CHEMBL2581	P07339	Cathepsin D	83.26%	98.95%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	83.12%	90.93%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	82.43%	85.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.67%	89.00%
CHEMBL4208	P20618	Proteasome component C5	81.25%	90.00%

Plants that contains it

• Caragana sinica

Cross-Links

• PubChem: 44427222
• NPASS: NPC202104