2-[[4-[(E)-3-[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-enyl]-2-(3,4-dihydroxyphenyl)-6-hydroxy-2,3-dihydro-1-benzofuran-3-yl]-hydroxymethoxy]-3-(3,4-dihydroxyphenyl)propanoic acid

Details

• Internal ID: f8f35531-bd8b-4291-98aa-25da7d1708d1
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: 2-[[4-[(E)-3-[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-enyl]-2-(3,4-dihydroxyphenyl)-6-hydroxy-2,3-dihydro-1-benzofuran-3-yl]-hydroxymethoxy]-3-(3,4-dihydroxyphenyl)propanoic acid
• SMILES (Canonical): C1=CC(=C(C=C1CC(C(=O)O)OC(C2C(OC3=CC(=CC(=C23)C=CC(=O)OC(CC4=CC(=C(C=C4)O)O)C(=O)O)O)C5=CC(=C(C=C5)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1CC(C(=O)O)OC(C2C(OC3=CC(=CC(=C23)/C=C/C(=O)OC(CC4=CC(=C(C=C4)O)O)C(=O)O)O)C5=CC(=C(C=C5)O)O)O)O)O
• InChI: InChI=1S/C36H32O16/c37-20-13-18(4-8-30(44)50-28(34(45)46)11-16-1-5-21(38)24(41)9-16)31-27(15-20)51-33(19-3-7-23(40)26(43)14-19)32(31)36(49)52-29(35(47)48)12-17-2-6-22(39)25(42)10-17/h1-10,13-15,28-29,32-33,36-43,49H,11-12H2,(H,45,46)(H,47,48)/b8-4+
• InChI Key: YLSNESYAOIRZEA-XBXARRHUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₃₂O₁₆
• Molecular Weight: 720.60 g/mol
• Exact Mass: 720.16903493 g/mol
• Topological Polar Surface Area (TPSA): 281.00 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.13
• H-Bond Acceptor: 14
• H-Bond Donor: 10
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9386	93.86%
Caco-2	-	0.9023	90.23%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7277	72.77%
OATP2B1 inhibitior	-	0.8448	84.48%
OATP1B1 inhibitior	+	0.8884	88.84%
OATP1B3 inhibitior	+	0.9315	93.15%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8036	80.36%
P-glycoprotein inhibitior	+	0.7108	71.08%
P-glycoprotein substrate	-	0.6578	65.78%
CYP3A4 substrate	+	0.6264	62.64%
CYP2C9 substrate	-	0.8002	80.02%
CYP2D6 substrate	-	0.8473	84.73%
CYP3A4 inhibition	-	0.8491	84.91%
CYP2C9 inhibition	+	0.6147	61.47%
CYP2C19 inhibition	-	0.6025	60.25%
CYP2D6 inhibition	-	0.9293	92.93%
CYP1A2 inhibition	-	0.7427	74.27%
CYP2C8 inhibition	+	0.7932	79.32%
CYP inhibitory promiscuity	-	0.6058	60.58%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9843	98.43%
Carcinogenicity (trinary)	Non-required	0.4149	41.49%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.8920	89.20%
Skin irritation	-	0.7352	73.52%
Skin corrosion	-	0.9432	94.32%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7199	71.99%
Micronuclear	+	0.8218	82.18%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.8114	81.14%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.7969	79.69%
Acute Oral Toxicity (c)	III	0.3187	31.87%
Estrogen receptor binding	+	0.7678	76.78%
Androgen receptor binding	+	0.7817	78.17%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.4883	48.83%
Aromatase binding	-	0.5089	50.89%
PPAR gamma	+	0.6781	67.81%
Honey bee toxicity	-	0.6988	69.88%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9934	99.34%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3729	P22748	Carbonic anhydrase IV	65.6 nM	Ki	via Super-PRED
CHEMBL2326	P43166	Carbonic anhydrase VII	35.5 nM	Ki	via Super-PRED
CHEMBL3242	O43570	Carbonic anhydrase XII	453.6 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.09%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.06%	94.45%
CHEMBL4040	P28482	MAP kinase ERK2	95.62%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.34%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.52%	99.17%
CHEMBL3194	P02766	Transthyretin	94.03%	90.71%
CHEMBL1951	P21397	Monoamine oxidase A	92.90%	91.49%
CHEMBL2581	P07339	Cathepsin D	92.73%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.39%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.20%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.39%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.40%	96.00%
CHEMBL233	P35372	Mu opioid receptor	87.39%	97.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.11%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.38%	97.09%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	82.76%	89.67%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	82.13%	97.53%
CHEMBL3401	O75469	Pregnane X receptor	81.71%	94.73%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	81.22%	95.17%

Plants that contains it

• Isodon serra
• Salvia miltiorrhiza
• Salvia przewalskii

Cross-Links

• PubChem: 56677421
• NPASS: NPC97678