(2S,3R)-3-(hydroxymethyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-carboxylic acid

Details

• Internal ID: ef088992-6498-4881-a5a8-fe73ae4f11ac
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: (2S,3R)-3-(hydroxymethyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-carboxylic acid
• SMILES (Canonical): C1=CC(=CC=C1C2C(C3=C(O2)C=CC(=C3)C(=O)O)CO)O
• SMILES (Isomeric): C1=CC(=CC=C1[C@@H]2[C@H](C3=C(O2)C=CC(=C3)C(=O)O)CO)O
• InChI: InChI=1S/C16H14O5/c17-8-13-12-7-10(16(19)20)3-6-14(12)21-15(13)9-1-4-11(18)5-2-9/h1-7,13,15,17-18H,8H2,(H,19,20)/t13-,15+/m0/s1
• InChI Key: ACJPWQXRDQNVEB-DZGCQCFKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₄O₅
• Molecular Weight: 286.28 g/mol
• Exact Mass: 286.08412354 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.30
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9909	99.09%
Caco-2	-	0.8122	81.22%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7839	78.39%
OATP2B1 inhibitior	-	0.7169	71.69%
OATP1B1 inhibitior	+	0.7696	76.96%
OATP1B3 inhibitior	-	0.2331	23.31%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8491	84.91%
P-glycoprotein inhibitior	-	0.8900	89.00%
P-glycoprotein substrate	-	0.9076	90.76%
CYP3A4 substrate	-	0.5757	57.57%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8242	82.42%
CYP3A4 inhibition	-	0.8740	87.40%
CYP2C9 inhibition	+	0.6865	68.65%
CYP2C19 inhibition	-	0.5731	57.31%
CYP2D6 inhibition	-	0.9167	91.67%
CYP1A2 inhibition	-	0.5159	51.59%
CYP2C8 inhibition	+	0.7707	77.07%
CYP inhibitory promiscuity	+	0.7106	71.06%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5771	57.71%
Eye corrosion	-	0.9902	99.02%
Eye irritation	+	0.8805	88.05%
Skin irritation	-	0.6253	62.53%
Skin corrosion	-	0.9767	97.67%
Ames mutagenesis	-	0.5723	57.23%
Human Ether-a-go-go-Related Gene inhibition	-	0.7084	70.84%
Micronuclear	+	0.8133	81.33%
Hepatotoxicity	-	0.5790	57.90%
skin sensitisation	-	0.8631	86.31%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	+	0.7063	70.63%
Acute Oral Toxicity (c)	III	0.4234	42.34%
Estrogen receptor binding	-	0.5384	53.84%
Androgen receptor binding	+	0.6207	62.07%
Thyroid receptor binding	+	0.6170	61.70%
Glucocorticoid receptor binding	+	0.5458	54.58%
Aromatase binding	+	0.5462	54.62%
PPAR gamma	+	0.5737	57.37%
Honey bee toxicity	-	0.9398	93.98%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.9725	97.25%

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	92.07%	91.11%
CHEMBL3194	P02766	Transthyretin	91.92%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.60%	99.17%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	91.18%	89.44%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.46%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.80%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.46%	97.09%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	84.76%	89.67%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.59%	96.09%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	82.57%	87.67%
CHEMBL1811	P34995	Prostanoid EP1 receptor	82.45%	95.71%
CHEMBL2581	P07339	Cathepsin D	82.27%	98.95%
CHEMBL5896	O75164	Lysine-specific demethylase 4A	81.18%	99.09%

Plants that contains it

• Selaginella moellendorffii

Cross-Links

• PubChem: 102262565
• LOTUS: LTS0268883
• wikiData: Q104909133