cis-3,5,3',4'-Tetrahydroxystilbene

Details

• Internal ID: b595a83f-15ed-425a-b5d6-3fceb1a858d4
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes
• IUPAC Name: 4-[(Z)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol
• SMILES (Canonical): C1=CC(=C(C=C1C=CC2=CC(=CC(=C2)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1/C=C\C2=CC(=CC(=C2)O)O)O)O
• InChI: InChI=1S/C14H12O4/c15-11-5-10(6-12(16)8-11)2-1-9-3-4-13(17)14(18)7-9/h1-8,15-18H/b2-1-
• InChI Key: CDRPUGZCRXZLFL-UPHRSURJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₂O₄
• Molecular Weight: 244.24 g/mol
• Exact Mass: 244.07355886 g/mol
• Topological Polar Surface Area (TPSA): 80.90 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 2.68
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

• 106325-86-4
• cis-3,5,3',4'-tetrahydroxystilbene
• 4-[(Z)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol
• CHEBI:76156
• Lopac-P-0453
• CHEMBL1603409
• SCHEMBL19953785
• DTXSID40424968
• CDRPUGZCRXZLFL-UPHRSURJSA-N
• (Z)-3,5,3',4'-tetrahydroxystilbene
• NCGC00015794-01
• (Z)-3,5,3/',4/'-Tetrahydroxystilbene
• J-001574
• Q27145793
• 5-[(1Z)-2-(3,4-dihydroxyphenyl)ethenyl]benzene-1,3-diol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9403	94.03%
Caco-2	+	0.7659	76.59%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5195	51.95%
OATP2B1 inhibitior	-	0.6931	69.31%
OATP1B1 inhibitior	+	0.9789	97.89%
OATP1B3 inhibitior	+	0.9799	97.99%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9088	90.88%
BSEP inhibitior	-	0.6653	66.53%
P-glycoprotein inhibitior	-	0.9568	95.68%
P-glycoprotein substrate	-	0.9936	99.36%
CYP3A4 substrate	-	0.7238	72.38%
CYP2C9 substrate	-	0.5963	59.63%
CYP2D6 substrate	-	0.7204	72.04%
CYP3A4 inhibition	+	0.5427	54.27%
CYP2C9 inhibition	+	0.6182	61.82%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	-	0.6100	61.00%
CYP inhibitory promiscuity	+	0.7651	76.51%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7723	77.23%
Carcinogenicity (trinary)	Non-required	0.5596	55.96%
Eye corrosion	-	0.9698	96.98%
Eye irritation	+	0.9970	99.70%
Skin irritation	+	0.6089	60.89%
Skin corrosion	-	0.5875	58.75%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7864	78.64%
Micronuclear	+	0.7400	74.00%
Hepatotoxicity	-	0.5964	59.64%
skin sensitisation	+	0.9376	93.76%
Respiratory toxicity	-	0.6667	66.67%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	-	0.7250	72.50%
Nephrotoxicity	-	0.5896	58.96%
Acute Oral Toxicity (c)	III	0.7909	79.09%
Estrogen receptor binding	+	0.9138	91.38%
Androgen receptor binding	+	0.8411	84.11%
Thyroid receptor binding	+	0.7823	78.23%
Glucocorticoid receptor binding	+	0.8424	84.24%
Aromatase binding	+	0.9377	93.77%
PPAR gamma	+	0.9167	91.67%
Honey bee toxicity	-	0.8277	82.77%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9851	98.51%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3687	P18054	Arachidonate 12-lipoxygenase	15848.9 nM	Potency	via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	794.3 nM; 794.3 nM	Potency; Potency	via Super-PRED; via CMAUP
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	240 nM	IC50	via Super-PRED
CHEMBL4801	P29466	Caspase-1	31622.8 nM	Potency	via CMAUP
CHEMBL4096	P04637	Cellular tumor antigen p53	10000 nM; 12589.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3356	P05177	Cytochrome P450 1A2	5011.87 nM	AC50	via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	31622.78 nM	AC50	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	19952.6 nM; 19952.6 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	1995.3 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL2424	Q04760	Glyoxalase I	760 nM	IC50	via Super-PRED
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	10000 nM; 10000 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	56.2 nM	Potency	via Super-PRED
CHEMBL1075189	P14618	Pyruvate kinase isozymes M1/M2	2511.9 nM; 2511.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293256	P40225	Thrombopoietin	2511.9 nM; 2511.9 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	98.80%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.61%	91.11%
CHEMBL3194	P02766	Transthyretin	96.88%	90.71%
CHEMBL1929	P47989	Xanthine dehydrogenase	93.27%	96.12%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.51%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.81%	96.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.53%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.72%	86.33%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	83.75%	80.78%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.78%	89.00%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.33%	91.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.93%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	80.66%	94.73%
CHEMBL4208	P20618	Proteasome component C5	80.40%	90.00%

Plants that contains it

• Rheum australe
• Rhodomyrtus tomentosa
• Smilax china

Cross-Links

• PubChem: 6603962
• NPASS: NPC58427
• ChEMBL: CHEMBL1603409