3-[4-Acetyloxy-3,5-bis(3-methylbut-2-enyl)phenyl]prop-2-enoic acid

Details

• Internal ID: 9399c5ec-f3bf-4706-82b6-1dd1153c71f7
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Cinnamic acids
• IUPAC Name: 3-[4-acetyloxy-3,5-bis(3-methylbut-2-enyl)phenyl]prop-2-enoic acid
• SMILES (Canonical): CC(=CCC1=CC(=CC(=C1OC(=O)C)CC=C(C)C)C=CC(=O)O)C
• SMILES (Isomeric): CC(=CCC1=CC(=CC(=C1OC(=O)C)CC=C(C)C)C=CC(=O)O)C
• InChI: InChI=1S/C21H26O4/c1-14(2)6-9-18-12-17(8-11-20(23)24)13-19(10-7-15(3)4)21(18)25-16(5)22/h6-8,11-13H,9-10H2,1-5H3,(H,23,24)
• InChI Key: YIJFXHBHKCTAET-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₆O₄
• Molecular Weight: 342.40 g/mol
• Exact Mass: 342.18310931 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 5.50
• Atomic LogP (AlogP): 4.73
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9952	99.52%
Caco-2	+	0.6288	62.88%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.9202	92.02%
OATP2B1 inhibitior	-	0.8525	85.25%
OATP1B1 inhibitior	+	0.9209	92.09%
OATP1B3 inhibitior	+	0.9012	90.12%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8297	82.97%
P-glycoprotein inhibitior	-	0.5809	58.09%
P-glycoprotein substrate	-	0.9345	93.45%
CYP3A4 substrate	-	0.6327	63.27%
CYP2C9 substrate	-	0.5853	58.53%
CYP2D6 substrate	-	0.8899	88.99%
CYP3A4 inhibition	-	0.8315	83.15%
CYP2C9 inhibition	+	0.5706	57.06%
CYP2C19 inhibition	+	0.7205	72.05%
CYP2D6 inhibition	-	0.7292	72.92%
CYP1A2 inhibition	+	0.5575	55.75%
CYP2C8 inhibition	-	0.7975	79.75%
CYP inhibitory promiscuity	-	0.6209	62.09%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6331	63.31%
Carcinogenicity (trinary)	Non-required	0.7551	75.51%
Eye corrosion	-	0.9747	97.47%
Eye irritation	+	0.6604	66.04%
Skin irritation	-	0.6805	68.05%
Skin corrosion	-	0.9610	96.10%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4644	46.44%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	-	0.5948	59.48%
skin sensitisation	-	0.5294	52.94%
Respiratory toxicity	-	0.6667	66.67%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	-	0.7750	77.50%
Nephrotoxicity	-	0.5612	56.12%
Acute Oral Toxicity (c)	III	0.6976	69.76%
Estrogen receptor binding	+	0.8123	81.23%
Androgen receptor binding	+	0.6336	63.36%
Thyroid receptor binding	-	0.5985	59.85%
Glucocorticoid receptor binding	+	0.7518	75.18%
Aromatase binding	+	0.7444	74.44%
PPAR gamma	+	0.8142	81.42%
Honey bee toxicity	-	0.8427	84.27%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6655	66.55%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.17%	96.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.64%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.44%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.34%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	90.04%	94.73%
CHEMBL221	P23219	Cyclooxygenase-1	87.75%	90.17%
CHEMBL2581	P07339	Cathepsin D	86.82%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.93%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.64%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.28%	99.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.19%	96.95%

Plants that contains it

• Baccharis polifolia

Cross-Links

• PubChem: 162996866
• LOTUS: LTS0018021
• wikiData: Q105348867