3-[2,4-Dihydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenoic acid

Details

• Internal ID: 00671a82-5533-445e-a5ab-6fe2b2b4a5ac
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acids
• IUPAC Name: 3-[2,4-dihydroxy-3-(3-methylbut-2-enyl)phenyl]prop-2-enoic acid
• InChI: InChI=1S/C14H16O4/c1-9(2)3-6-11-12(15)7-4-10(14(11)18)5-8-13(16)17/h3-5,7-8,15,18H,6H2,1-2H3,(H,16,17)
• InChI Key: MRMWRWJVPXDMEJ-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₆O₄
• Molecular Weight: 248.27 g/mol
• Exact Mass: 248.10485899 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.70
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9902	99.02%
Caco-2	+	0.7241	72.41%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8171	81.71%
OATP2B1 inhibitior	-	0.5735	57.35%
OATP1B1 inhibitior	+	0.8637	86.37%
OATP1B3 inhibitior	+	0.9574	95.74%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8588	85.88%
BSEP inhibitior	-	0.5942	59.42%
P-glycoprotein inhibitior	-	0.9527	95.27%
P-glycoprotein substrate	-	0.9145	91.45%
CYP3A4 substrate	-	0.6028	60.28%
CYP2C9 substrate	-	0.5994	59.94%
CYP2D6 substrate	-	0.8717	87.17%
CYP3A4 inhibition	-	0.7312	73.12%
CYP2C9 inhibition	+	0.8138	81.38%
CYP2C19 inhibition	+	0.7465	74.65%
CYP2D6 inhibition	-	0.8192	81.92%
CYP1A2 inhibition	+	0.6360	63.60%
CYP2C8 inhibition	-	0.7519	75.19%
CYP inhibitory promiscuity	+	0.6152	61.52%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7542	75.42%
Carcinogenicity (trinary)	Non-required	0.7811	78.11%
Eye corrosion	-	0.9511	95.11%
Eye irritation	+	0.9327	93.27%
Skin irritation	-	0.5469	54.69%
Skin corrosion	-	0.8561	85.61%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6912	69.12%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	+	0.7816	78.16%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.7014	70.14%
Acute Oral Toxicity (c)	III	0.6007	60.07%
Estrogen receptor binding	+	0.8632	86.32%
Androgen receptor binding	+	0.5658	56.58%
Thyroid receptor binding	+	0.6038	60.38%
Glucocorticoid receptor binding	+	0.8777	87.77%
Aromatase binding	+	0.5932	59.32%
PPAR gamma	+	0.8745	87.45%
Honey bee toxicity	-	0.9625	96.25%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.8700	87.00%
Fish aquatic toxicity	+	0.9960	99.60%

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	98.09%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	92.57%	90.17%
CHEMBL2581	P07339	Cathepsin D	89.62%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.50%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.46%	96.00%
CHEMBL1951	P21397	Monoamine oxidase A	87.46%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	86.49%	94.73%
CHEMBL3194	P02766	Transthyretin	86.36%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.64%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.24%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.45%	96.09%

Plants that contains it

• Baccharis linearis

Cross-Links

• PubChem: 129686660
• LOTUS: LTS0144021
• wikiData: Q105170723