(E)-5-(4-Methoxystyryl)benzene-1,3-diol

Details

• Internal ID: 9bde558e-168b-42f9-8318-3e5f3c8a91e5
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes
• IUPAC Name: 5-[(E)-2-(4-methoxyphenyl)ethenyl]benzene-1,3-diol
• SMILES (Canonical): COC1=CC=C(C=C1)C=CC2=CC(=CC(=C2)O)O
• SMILES (Isomeric): COC1=CC=C(C=C1)/C=C/C2=CC(=CC(=C2)O)O
• InChI: InChI=1S/C15H14O3/c1-18-15-6-4-11(5-7-15)2-3-12-8-13(16)10-14(17)9-12/h2-10,16-17H,1H3/b3-2+
• InChI Key: IHVRWFJGOIWMGC-NSCUHMNNSA-N
• Popularity: 42 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₄O₃
• Molecular Weight: 242.27 g/mol
• Exact Mass: 242.094294304 g/mol
• Topological Polar Surface Area (TPSA): 49.70 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.28
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• (E)-5-(4-Methoxystyryl)benzene-1,3-diol
• 4'-Methoxyresveratrol
• RESVERATROL 4'-METHYL ETHER
• Desoxyrhapontigenin
• Deoxyrhapontigenin
• 4-Methoxyresveratrol
• 3,5-Dihydroxy-4'-methoxystilbene
• RU7RRY3RUW
• CHEMBL291501
• BML 233
• 1,3-Benzenediol, 5-[(1E)-2-(4-methoxyphenyl)ethenyl]-
• DHMS cpd
• 5-[(E)-2-(4-methoxyphenyl)ethenyl]benzene-1,3-diol
• Desoxyrhaponigenin
• UNII-RU7RRY3RUW
• 5-[2-(4-Methoxyphenyl)ethenyl]-1,3-benzenediol
• Spectrum5_000570
• BSPBio_003527
• SCHEMBL563261
• SCHEMBL563262
• 4'-Methoxystilbene-3,5-diol
• 4/'-Methoxystilbene-3,5-diol
• BML-233
• CHEBI:108593
• IHVRWFJGOIWMGC-NSCUHMNNSA-N
• DTXSID101031720
• 3,5-dihydroxy-4''-methoxystilbene
• HY-N2485
• BDBM50085541
• CCG-38350
• MFCD12407152
• s3939
• 5-(4-methoxystyryl)benzene-1,3-diol
• AKOS015915073
• AC-7025
• SDCCGMLS-0066773.P001
• QTL1_000070
• trans-3,5-dihydroxy-4'-methoxystilbene
• (E)-3,5-dihydroxy-4''-methoxystilbene
• 13E-3,5-dihydroxy-4''-methoxystilbene
• NCGC00094628-01
• NCGC00094628-02
• 3,5-dihydroxy-4'-methoxy-trans-stilbene
• DS-15252
• trans-3,5-dihydroxy-4''-methoxystilbene
• (E)-5-(4-Methoxystyryl)benzene-13-diol
• CS-0022756
• (E)-3,5-DIHYDROXY-4'-METHOXYSTILBENE
• 3,5-STILBENEDIOL, 4'-METHOXY-, (E)-
• A821880
• SR-05000002490
• 1,3-Benzenediol, 5-[2-(4-methoxyphenyl)ethenyl]-
• 5-[2-(4-Methoxy-phenyl)-vinyl]-benzene-1,3-diol
• SR-05000002490-1
• 5-[(E)-2-(4-methoxyphenyl)vinyl]benzene-1,3-diol
• BRD-K02671211-001-02-2
• BRD-K02671211-001-03-0
• E 5-[2-(4-Methoxy-phenyl)-vinyl]-benzene-1,3-diol
• Q17299987
• 5-[(E)-2-(4-Methoxy-phenyl)-vinyl]-benzene-1,3-diol
• 5-[2-((E)-4-Methoxy-phenyl)-vinyl]-benzene-1,3-diol
• 1,3-Benzenediol, 5-[(E)-2-(4-methoxyphenyl)ethenyl]-
• 5-((1E)-2-(4-METHOXYPHENYL)ETHENYL)-1,3-BENZENEDIOL
• 1,3-BENZENEDIOL, 5-(2-(4-METHOXYPHENYL)ETHENYL)-, (E)-
• 5-[2-(4-methoxyphenyl)vinyl]benzene-1,3-diol;(E)-5-(4-Methoxystyryl)benzene-1,3-diol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9888	98.88%
Caco-2	+	0.8688	86.88%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7441	74.41%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9489	94.89%
OATP1B3 inhibitior	+	0.9749	97.49%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8838	88.38%
BSEP inhibitior	-	0.5572	55.72%
P-glycoprotein inhibitior	-	0.9055	90.55%
P-glycoprotein substrate	-	0.9826	98.26%
CYP3A4 substrate	-	0.6515	65.15%
CYP2C9 substrate	-	0.5963	59.63%
CYP2D6 substrate	-	0.6581	65.81%
CYP3A4 inhibition	+	0.5761	57.61%
CYP2C9 inhibition	+	0.7138	71.38%
CYP2C19 inhibition	+	0.8614	86.14%
CYP2D6 inhibition	-	0.9055	90.55%
CYP1A2 inhibition	+	0.9338	93.38%
CYP2C8 inhibition	-	0.6524	65.24%
CYP inhibitory promiscuity	+	0.8533	85.33%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.6739	67.39%
Carcinogenicity (trinary)	Non-required	0.5484	54.84%
Eye corrosion	-	0.9699	96.99%
Eye irritation	+	0.9716	97.16%
Skin irritation	-	0.6370	63.70%
Skin corrosion	-	0.7135	71.35%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5947	59.47%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	-	0.7267	72.67%
skin sensitisation	-	0.5559	55.59%
Respiratory toxicity	-	0.8000	80.00%
Reproductive toxicity	-	0.5667	56.67%
Mitochondrial toxicity	-	0.7750	77.50%
Nephrotoxicity	+	0.4771	47.71%
Acute Oral Toxicity (c)	III	0.6259	62.59%
Estrogen receptor binding	+	0.8785	87.85%
Androgen receptor binding	+	0.7056	70.56%
Thyroid receptor binding	+	0.7059	70.59%
Glucocorticoid receptor binding	+	0.6209	62.09%
Aromatase binding	+	0.8888	88.88%
PPAR gamma	+	0.8077	80.77%
Honey bee toxicity	-	0.9553	95.53%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.6600	66.00%
Fish aquatic toxicity	+	0.9231	92.31%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3687	P18054	Arachidonate 12-lipoxygenase	19952.6 nM	Potency	via CMAUP
CHEMBL221	P23219	Cyclooxygenase-1	25800 nM	IC50	PMID: 18487053
CHEMBL230	P35354	Cyclooxygenase-2	19600 nM	IC50	PMID: 18487053
CHEMBL2231	P04798	Cytochrome P450 1A1	160 nM	Ki	DOI: 10.1039/C0MD00242A
CHEMBL4878	Q16678	Cytochrome P450 1B1	800 nM; 800 nM	IC50; IC50	DOI: 10.1039/C3MD00317E; via Super-PRED
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	22387.2 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	11220.2 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.78%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.80%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.39%	96.00%
CHEMBL4208	P20618	Proteasome component C5	90.59%	90.00%
CHEMBL3194	P02766	Transthyretin	89.75%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.49%	86.33%
CHEMBL1929	P47989	Xanthine dehydrogenase	89.08%	96.12%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.56%	96.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	86.64%	93.99%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.27%	99.17%
CHEMBL1951	P21397	Monoamine oxidase A	82.20%	91.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.29%	99.15%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	80.72%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	80.29%	94.73%

Plants that contains it

• Dracaena cochinchinensis
• Knema austrosiamensis
• Rheum australe
• Rheum officinale
• Rheum palmatum
• Rheum rhabarbarum
• Rheum tanguticum
• Rumex bucephalophorus

Cross-Links

• PubChem: 6255462
• NPASS: NPC296920
• ChEMBL: CHEMBL291501
• LOTUS: LTS0110115
• wikiData: Q17299987