4-[(2R,5S)-5-(hydroxymethyl)-4-(4-hydroxyphenyl)-2,5-dihydrofuran-2-yl]phenol

Details

• Internal ID: 5390333b-3233-40cd-8076-620b86acd25e
• Taxonomy: Benzenoids > Phenols > 1-hydroxy-2-unsubstituted benzenoids
• IUPAC Name: 4-[(2R,5S)-5-(hydroxymethyl)-4-(4-hydroxyphenyl)-2,5-dihydrofuran-2-yl]phenol
• SMILES (Canonical): C1=CC(=CC=C1C2C=C(C(O2)CO)C3=CC=C(C=C3)O)O
• SMILES (Isomeric): C1=CC(=CC=C1[C@H]2C=C([C@H](O2)CO)C3=CC=C(C=C3)O)O
• InChI: InChI=1S/C17H16O4/c18-10-17-15(11-1-5-13(19)6-2-11)9-16(21-17)12-3-7-14(20)8-4-12/h1-9,16-20H,10H2/t16-,17-/m1/s1
• InChI Key: JTAOIOJXOYUGRH-IAGOWNOFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₆O₄
• Molecular Weight: 284.31 g/mol
• Exact Mass: 284.10485899 g/mol
• Topological Polar Surface Area (TPSA): 69.90 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.61
• 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	+	0.9821	98.21%
Caco-2	+	0.5061	50.61%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7757	77.57%
OATP2B1 inhibitior	-	0.8595	85.95%
OATP1B1 inhibitior	+	0.8406	84.06%
OATP1B3 inhibitior	+	0.9028	90.28%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.8687	86.87%
P-glycoprotein inhibitior	-	0.8014	80.14%
P-glycoprotein substrate	-	0.9547	95.47%
CYP3A4 substrate	-	0.5851	58.51%
CYP2C9 substrate	-	0.8141	81.41%
CYP2D6 substrate	-	0.7316	73.16%
CYP3A4 inhibition	-	0.7012	70.12%
CYP2C9 inhibition	-	0.5385	53.85%
CYP2C19 inhibition	-	0.5379	53.79%
CYP2D6 inhibition	-	0.9089	90.89%
CYP1A2 inhibition	+	0.6324	63.24%
CYP2C8 inhibition	+	0.7014	70.14%
CYP inhibitory promiscuity	+	0.9474	94.74%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8735	87.35%
Carcinogenicity (trinary)	Danger	0.4654	46.54%
Eye corrosion	-	0.9889	98.89%
Eye irritation	+	0.7225	72.25%
Skin irritation	-	0.7560	75.60%
Skin corrosion	-	0.9439	94.39%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3881	38.81%
Micronuclear	+	0.6318	63.18%
Hepatotoxicity	+	0.5304	53.04%
skin sensitisation	-	0.6592	65.92%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	+	0.6562	65.62%
Acute Oral Toxicity (c)	III	0.6456	64.56%
Estrogen receptor binding	+	0.5769	57.69%
Androgen receptor binding	+	0.7778	77.78%
Thyroid receptor binding	+	0.5181	51.81%
Glucocorticoid receptor binding	-	0.6029	60.29%
Aromatase binding	+	0.7049	70.49%
PPAR gamma	+	0.8061	80.61%
Honey bee toxicity	-	0.9400	94.00%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9334	93.34%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL242	Q92731	Estrogen receptor beta	96.60%	98.35%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.63%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.83%	97.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.01%	86.92%
CHEMBL2581	P07339	Cathepsin D	84.63%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.86%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	82.78%	94.73%
CHEMBL206	P03372	Estrogen receptor alpha	81.96%	97.64%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.03%	86.33%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.38%	91.71%

Plants that contains it

• Araucaria angustifolia
• Chamaecyparis obtusa
• Cryptomeria japonica

Cross-Links

• PubChem: 101461988
• LOTUS: LTS0059244
• wikiData: Q104401615