3,3',4,5'-Tetrahydroxybibenzyl

Details

• Internal ID: 3d473077-a975-4645-bfba-bf5b456234ad
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes
• IUPAC Name: 4-[2-(3,5-dihydroxyphenyl)ethyl]benzene-1,2-diol
• SMILES (Canonical): C1=CC(=C(C=C1CCC2=CC(=CC(=C2)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1CCC2=CC(=CC(=C2)O)O)O)O
• InChI: InChI=1S/C14H14O4/c15-11-5-10(6-12(16)8-11)2-1-9-3-4-13(17)14(18)7-9/h3-8,15-18H,1-2H2
• InChI Key: KTLRRKBJXAJHJD-UHFFFAOYSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₄O₄
• Molecular Weight: 246.26 g/mol
• Exact Mass: 246.08920892 g/mol
• Topological Polar Surface Area (TPSA): 80.90 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 2.29
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

• 22318-80-5
• 4-[2-(3,5-dihydroxyphenyl)ethyl]benzene-1,2-diol
• CHEMBL329520
• Dihydropiceatannol
• SCHEMBL4542482
• DTXSID10176861
• 3,3',4',5-Tetrahydroxybibenzyl
• 3,3'',4'',5-tetrahydroxybibenzyl
• BDBM50045930
• 4-(3,5-dihydroxyphenethyl)-1,2-benzenediol
• 1,2-Benzenediol, 4-(2-(3,5-dihydroxyphenyl)ethyl)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7093	70.93%
Caco-2	+	0.5597	55.97%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7231	72.31%
OATP2B1 inhibitior	-	0.5646	56.46%
OATP1B1 inhibitior	+	0.9627	96.27%
OATP1B3 inhibitior	+	0.9651	96.51%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6662	66.62%
P-glycoprotein inhibitior	-	0.9636	96.36%
P-glycoprotein substrate	-	0.9431	94.31%
CYP3A4 substrate	-	0.6949	69.49%
CYP2C9 substrate	-	0.8019	80.19%
CYP2D6 substrate	+	0.4041	40.41%
CYP3A4 inhibition	-	0.5857	58.57%
CYP2C9 inhibition	+	0.7410	74.10%
CYP2C19 inhibition	-	0.6677	66.77%
CYP2D6 inhibition	-	0.8412	84.12%
CYP1A2 inhibition	+	0.7960	79.60%
CYP2C8 inhibition	+	0.4484	44.84%
CYP inhibitory promiscuity	+	0.6231	62.31%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7423	74.23%
Carcinogenicity (trinary)	Non-required	0.6342	63.42%
Eye corrosion	-	0.9696	96.96%
Eye irritation	+	0.9884	98.84%
Skin irritation	+	0.5282	52.82%
Skin corrosion	-	0.6500	65.00%
Ames mutagenesis	+	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6180	61.80%
Micronuclear	-	0.5441	54.41%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	+	0.7282	72.82%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	-	0.6359	63.59%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.6978	69.78%
Acute Oral Toxicity (c)	III	0.8171	81.71%
Estrogen receptor binding	+	0.8793	87.93%
Androgen receptor binding	+	0.8352	83.52%
Thyroid receptor binding	+	0.6459	64.59%
Glucocorticoid receptor binding	+	0.7383	73.83%
Aromatase binding	+	0.8504	85.04%
PPAR gamma	+	0.8773	87.73%
Honey bee toxicity	-	0.8741	87.41%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.9333	93.33%

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	97.28%	91.11%
CHEMBL2581	P07339	Cathepsin D	88.61%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	87.71%	91.49%
CHEMBL3194	P02766	Transthyretin	87.18%	90.71%
CHEMBL4208	P20618	Proteasome component C5	86.19%	90.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.89%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.53%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.24%	99.17%
CHEMBL3492	P49721	Proteasome Macropain subunit	82.39%	90.24%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.40%	96.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.08%	86.33%

Plants that contains it

• Dioscorea antaly
• Rheum rhabarbarum
• Senna garrettiana

Cross-Links

• PubChem: 152444
• NPASS: NPC268032
• ChEMBL: CHEMBL329520
• LOTUS: LTS0246045
• wikiData: Q83047189