3-[4-Hydroxy-2,6-bis(3-methylbut-2-enyl)phenyl]prop-2-enoic acid

Details

• Internal ID: cd7667e1-e8f5-4155-8723-d0a69808bedd
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acids
• IUPAC Name: 3-[4-hydroxy-2,6-bis(3-methylbut-2-enyl)phenyl]prop-2-enoic acid
• SMILES (Canonical): CC(=CCC1=CC(=CC(=C1C=CC(=O)O)CC=C(C)C)O)C
• SMILES (Isomeric): CC(=CCC1=CC(=CC(=C1C=CC(=O)O)CC=C(C)C)O)C
• InChI: InChI=1S/C19H24O3/c1-13(2)5-7-15-11-17(20)12-16(8-6-14(3)4)18(15)9-10-19(21)22/h5-6,9-12,20H,7-8H2,1-4H3,(H,21,22)
• InChI Key: QNSRZGLDNYHDKG-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₄O₃
• Molecular Weight: 300.40 g/mol
• Exact Mass: 300.17254462 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 5.40
• Atomic LogP (AlogP): 4.51
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9961	99.61%
Caco-2	+	0.7964	79.64%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.9093	90.93%
OATP2B1 inhibitior	-	0.7105	71.05%
OATP1B1 inhibitior	+	0.8986	89.86%
OATP1B3 inhibitior	+	0.9450	94.50%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8230	82.30%
P-glycoprotein inhibitior	-	0.8638	86.38%
P-glycoprotein substrate	-	0.9088	90.88%
CYP3A4 substrate	-	0.6403	64.03%
CYP2C9 substrate	-	0.5994	59.94%
CYP2D6 substrate	-	0.8717	87.17%
CYP3A4 inhibition	-	0.7033	70.33%
CYP2C9 inhibition	+	0.6811	68.11%
CYP2C19 inhibition	+	0.7262	72.62%
CYP2D6 inhibition	-	0.7272	72.72%
CYP1A2 inhibition	+	0.5264	52.64%
CYP2C8 inhibition	-	0.8357	83.57%
CYP inhibitory promiscuity	+	0.7233	72.33%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.6827	68.27%
Carcinogenicity (trinary)	Non-required	0.7499	74.99%
Eye corrosion	-	0.9589	95.89%
Eye irritation	+	0.8656	86.56%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.8788	87.88%
Ames mutagenesis	-	0.6554	65.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5173	51.73%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.5302	53.02%
skin sensitisation	+	0.6351	63.51%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.5560	55.60%
Acute Oral Toxicity (c)	III	0.7275	72.75%
Estrogen receptor binding	+	0.6451	64.51%
Androgen receptor binding	+	0.6644	66.44%
Thyroid receptor binding	+	0.5523	55.23%
Glucocorticoid receptor binding	+	0.7875	78.75%
Aromatase binding	+	0.6389	63.89%
PPAR gamma	+	0.9026	90.26%
Honey bee toxicity	-	0.9504	95.04%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.7600	76.00%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.55%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	90.14%	94.73%
CHEMBL2581	P07339	Cathepsin D	89.06%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.05%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.68%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.72%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.74%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.17%	99.17%
CHEMBL221	P23219	Cyclooxygenase-1	81.68%	90.17%

Plants that contains it

• Baccharis trinervis
• Salvia limbata

Cross-Links

• PubChem: 162967528
• LOTUS: LTS0192461
• wikiData: Q105283320