5,6-Dihydroxy-2-(2',4',6'-trihydroxyphenyl)benzofuran-3-carboxylic acid

Details

• Internal ID: afc8ea3a-b966-458f-9a0f-1b06629b3c14
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: 5,6-dihydroxy-2-(2,4,6-trihydroxyphenyl)-1-benzofuran-3-carboxylic acid
• SMILES (Canonical): C1=C(C=C(C(=C1O)C2=C(C3=CC(=C(C=C3O2)O)O)C(=O)O)O)O
• SMILES (Isomeric): C1=C(C=C(C(=C1O)C2=C(C3=CC(=C(C=C3O2)O)O)C(=O)O)O)O
• InChI: InChI=1S/C15H10O8/c16-5-1-9(19)13(10(20)2-5)14-12(15(21)22)6-3-7(17)8(18)4-11(6)23-14/h1-4,16-20H,(H,21,22)
• InChI Key: OYMZVRJQIIYPTP-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₀O₈
• Molecular Weight: 318.23 g/mol
• Exact Mass: 318.03756727 g/mol
• Topological Polar Surface Area (TPSA): 152.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.33
• H-Bond Acceptor: 7
• H-Bond Donor: 6
• Rotatable Bonds: 2

Synonyms

• 5,6-Dihydroxy-2-(2',4',6'-trihydroxyphenyl)benzofuran-3-carboxylic acid
• 100288-12-8
• DTXSID90658074
• LMPK12160052
• 5,6-Dihydroxy-2-(2,4,6-trihydroxyphenyl)-1-benzofuran-3-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9540	95.40%
Caco-2	-	0.8573	85.73%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6025	60.25%
OATP2B1 inhibitior	-	0.5173	51.73%
OATP1B1 inhibitior	+	0.9342	93.42%
OATP1B3 inhibitior	-	0.2596	25.96%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8986	89.86%
P-glycoprotein inhibitior	-	0.9203	92.03%
P-glycoprotein substrate	-	0.9174	91.74%
CYP3A4 substrate	-	0.6115	61.15%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8815	88.15%
CYP3A4 inhibition	-	0.5220	52.20%
CYP2C9 inhibition	-	0.6611	66.11%
CYP2C19 inhibition	-	0.8608	86.08%
CYP2D6 inhibition	-	0.9368	93.68%
CYP1A2 inhibition	+	0.5931	59.31%
CYP2C8 inhibition	+	0.5651	56.51%
CYP inhibitory promiscuity	+	0.5150	51.50%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5234	52.34%
Eye corrosion	-	0.9918	99.18%
Eye irritation	+	0.9504	95.04%
Skin irritation	+	0.5307	53.07%
Skin corrosion	-	0.9525	95.25%
Ames mutagenesis	-	0.6170	61.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.9084	90.84%
Micronuclear	+	0.9400	94.00%
Hepatotoxicity	+	0.5232	52.32%
skin sensitisation	-	0.7658	76.58%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.5713	57.13%
Acute Oral Toxicity (c)	II	0.3740	37.40%
Estrogen receptor binding	+	0.7323	73.23%
Androgen receptor binding	+	0.8098	80.98%
Thyroid receptor binding	+	0.5430	54.30%
Glucocorticoid receptor binding	+	0.8886	88.86%
Aromatase binding	-	0.5231	52.31%
PPAR gamma	+	0.8724	87.24%
Honey bee toxicity	-	0.8938	89.38%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9813	98.13%

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	98.22%	91.11%
CHEMBL3194	P02766	Transthyretin	93.56%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.36%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.83%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.60%	95.56%
CHEMBL1811	P34995	Prostanoid EP1 receptor	87.58%	95.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.89%	99.23%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.43%	99.15%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	84.15%	94.42%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.36%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	81.69%	94.73%

Plants that contains it

• Sphagneticola calendulacea
• Wedelia acapulcensis var. hispida

Cross-Links

• PubChem: 44260115
• LOTUS: LTS0269094
• wikiData: Q82573797