E-Combretastatin A-4

Details

• Internal ID: ced217ad-2605-4db1-9661-d1f124d39940
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes
• IUPAC Name: 2-methoxy-5-[(E)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenol
• SMILES (Canonical): COC1=C(C=C(C=C1)C=CC2=CC(=C(C(=C2)OC)OC)OC)O
• SMILES (Isomeric): COC1=C(C=C(C=C1)/C=C/C2=CC(=C(C(=C2)OC)OC)OC)O
• InChI: InChI=1S/C18H20O5/c1-20-15-8-7-12(9-14(15)19)5-6-13-10-16(21-2)18(23-4)17(11-13)22-3/h5-11,19H,1-4H3/b6-5+
• InChI Key: HVXBOLULGPECHP-AATRIKPKSA-N
• Popularity: 13 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₀O₅
• Molecular Weight: 316.30 g/mol
• Exact Mass: 316.13107373 g/mol
• Topological Polar Surface Area (TPSA): 57.20 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 3.60
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

• Trans-Combretastatin A-4
• Combretastatin A4, trans-
• NSC-609397
• E-Combretastatin A-4
• UNII-ND4BUQ9WHL
• CHEMBL36455
• NSC609397
• NSC613729
• 2-methoxy-5-[(E)-2-(3,4,5-trimethoxyphenyl)vinyl]phenol
• 2-methoxy-5-[(E)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenol
• 2-Methoxy-5-((1E)-2-(3,4,5-trimethoxyphenyl)ethenyl)phenol
• Phenol, 2-methoxy-5-((1E)-2-(3,4,5-trimethoxyphenyl)ethenyl)-
• 117048-62-1
• 2-Methoxy-5-[(1E)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenol
• Phenol, 2-methoxy-5-[(1E)-2-(3,4,5-trimethoxyphenyl)ethenyl]-
• 2-methoxy-5-(3,4,5-trimethoxystyryl)phenol
• trans-(E)-Combretastatin
• 2-Methoxy-5-[2-(3,4,5-trimethoxy-phenyl)-vinyl]-phenol
• From Combretum caffrum plant
• SCHEMBL18946
• SCHEMBL9707931
• HVXBOLULGPECHP-AATRIKPKSA-N
• BDBM50009561
• CCG-35662
• CCG-36400
• AKOS015915109
• ND-2980
• B817373K328
• (E)-5-(3,4,5-trimethoxystyryl)-2-methoxyphenol
• A803704
• J-003498
• 2-Methoxy-5-(2-(3,4,5-trimethoxyphenyl)vinyl)phenol
• 2-Methoxy-5-[(E)-2-(3,4,5-trimethoxy-phenyl)-vinyl]-phenol
• trans-2-Methoxy-5-[(Z)-2-(3,4,5-trimethoxy-phenyl)-vinyl]-phenol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9904	99.04%
Caco-2	+	0.9065	90.65%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7414	74.14%
OATP2B1 inhibitior	-	0.8650	86.50%
OATP1B1 inhibitior	+	0.9620	96.20%
OATP1B3 inhibitior	+	0.9710	97.10%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.5904	59.04%
P-glycoprotein inhibitior	-	0.6057	60.57%
P-glycoprotein substrate	-	0.9672	96.72%
CYP3A4 substrate	-	0.6196	61.96%
CYP2C9 substrate	-	0.5963	59.63%
CYP2D6 substrate	-	0.6581	65.81%
CYP3A4 inhibition	-	0.5175	51.75%
CYP2C9 inhibition	-	0.9658	96.58%
CYP2C19 inhibition	-	0.5529	55.29%
CYP2D6 inhibition	-	0.8911	89.11%
CYP1A2 inhibition	+	0.6781	67.81%
CYP2C8 inhibition	+	0.6888	68.88%
CYP inhibitory promiscuity	+	0.7126	71.26%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7721	77.21%
Carcinogenicity (trinary)	Non-required	0.5763	57.63%
Eye corrosion	-	0.9724	97.24%
Eye irritation	-	0.5104	51.04%
Skin irritation	-	0.7622	76.22%
Skin corrosion	-	0.9708	97.08%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7315	73.15%
Micronuclear	-	0.5367	53.67%
Hepatotoxicity	-	0.6163	61.63%
skin sensitisation	-	0.7766	77.66%
Respiratory toxicity	-	0.8444	84.44%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	-	0.8250	82.50%
Nephrotoxicity	-	0.7669	76.69%
Acute Oral Toxicity (c)	III	0.6026	60.26%
Estrogen receptor binding	+	0.8501	85.01%
Androgen receptor binding	+	0.7195	71.95%
Thyroid receptor binding	+	0.7853	78.53%
Glucocorticoid receptor binding	-	0.5334	53.34%
Aromatase binding	+	0.7142	71.42%
PPAR gamma	-	0.5323	53.23%
Honey bee toxicity	-	0.9108	91.08%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9791	97.91%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4302	P08183	P-glycoprotein 1	6.6 nM	IC50	via Super-PRED
CHEMBL2597	Q13509	Tubulin beta-3 chain	5.2 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.74%	96.00%
CHEMBL3194	P02766	Transthyretin	94.34%	90.71%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.83%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.60%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.05%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	88.97%	91.49%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	88.76%	92.68%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.32%	96.09%
CHEMBL1255126	O15151	Protein Mdm4	85.25%	90.20%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.41%	89.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	82.83%	89.62%
CHEMBL3788	O00444	Serine/threonine-protein kinase PLK4	82.48%	83.65%
CHEMBL2535	P11166	Glucose transporter	81.55%	98.75%

Plants that contains it

• Combretum caffrum

Cross-Links

• PubChem: 5386397
• LOTUS: LTS0271753
• wikiData: Q105110565