3-[3-(3,7-Dimethylocta-2,6-dienyl)-4,5-dimethoxyphenyl]prop-2-enoic acid

Details

• Internal ID: 283c847e-7f80-4179-a762-664db2417879
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: 3-[3-(3,7-dimethylocta-2,6-dienyl)-4,5-dimethoxyphenyl]prop-2-enoic acid
• SMILES (Canonical): CC(=CCCC(=CCC1=C(C(=CC(=C1)C=CC(=O)O)OC)OC)C)C
• SMILES (Isomeric): CC(=CCCC(=CCC1=C(C(=CC(=C1)C=CC(=O)O)OC)OC)C)C
• InChI: InChI=1S/C21H28O4/c1-15(2)7-6-8-16(3)9-11-18-13-17(10-12-20(22)23)14-19(24-4)21(18)25-5/h7,9-10,12-14H,6,8,11H2,1-5H3,(H,22,23)
• InChI Key: IXDDIYJCTLFLLS-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₈O₄
• Molecular Weight: 344.40 g/mol
• Exact Mass: 344.19875937 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 5.60
• Atomic LogP (AlogP): 5.04
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9921	99.21%
Caco-2	+	0.9002	90.02%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8815	88.15%
OATP2B1 inhibitior	-	0.8576	85.76%
OATP1B1 inhibitior	+	0.9069	90.69%
OATP1B3 inhibitior	+	0.9025	90.25%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.9566	95.66%
P-glycoprotein inhibitior	+	0.5993	59.93%
P-glycoprotein substrate	-	0.8729	87.29%
CYP3A4 substrate	-	0.5081	50.81%
CYP2C9 substrate	-	0.7907	79.07%
CYP2D6 substrate	-	0.8620	86.20%
CYP3A4 inhibition	-	0.6581	65.81%
CYP2C9 inhibition	-	0.6247	62.47%
CYP2C19 inhibition	+	0.6567	65.67%
CYP2D6 inhibition	-	0.8486	84.86%
CYP1A2 inhibition	+	0.5102	51.02%
CYP2C8 inhibition	+	0.5590	55.90%
CYP inhibitory promiscuity	-	0.7385	73.85%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7240	72.40%
Carcinogenicity (trinary)	Non-required	0.7127	71.27%
Eye corrosion	-	0.9854	98.54%
Eye irritation	-	0.7305	73.05%
Skin irritation	-	0.7515	75.15%
Skin corrosion	-	0.9780	97.80%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7552	75.52%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.6573	65.73%
skin sensitisation	-	0.6631	66.31%
Respiratory toxicity	-	0.7000	70.00%
Reproductive toxicity	-	0.5111	51.11%
Mitochondrial toxicity	-	0.8375	83.75%
Nephrotoxicity	-	0.7518	75.18%
Acute Oral Toxicity (c)	III	0.6348	63.48%
Estrogen receptor binding	+	0.8079	80.79%
Androgen receptor binding	+	0.5681	56.81%
Thyroid receptor binding	+	0.6639	66.39%
Glucocorticoid receptor binding	+	0.7316	73.16%
Aromatase binding	+	0.6359	63.59%
PPAR gamma	+	0.7665	76.65%
Honey bee toxicity	-	0.8630	86.30%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5955	59.55%
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	96.79%	96.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.35%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.22%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.22%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.39%	99.17%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	91.52%	92.08%
CHEMBL221	P23219	Cyclooxygenase-1	89.15%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.61%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	86.61%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.42%	85.14%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	85.98%	92.68%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.08%	94.45%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	81.66%	97.21%

Plants that contains it

• Lorandersonia pulchella

Cross-Links

• PubChem: 162915876
• LOTUS: LTS0196848
• wikiData: Q105122055