Methyl 3,4-dihydroxy-5-(2-hydroxy-3-methylbut-3-enyl)benzoate

Details

• Internal ID: 1aca8c7f-7c86-418a-a935-5b8c3b0d5acc
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzoic acids and derivatives > p-Hydroxybenzoic acid esters > p-Hydroxybenzoic acid alkyl esters
• IUPAC Name: methyl 3,4-dihydroxy-5-(2-hydroxy-3-methylbut-3-enyl)benzoate
• SMILES (Canonical): CC(=C)C(CC1=C(C(=CC(=C1)C(=O)OC)O)O)O
• SMILES (Isomeric): CC(=C)C(CC1=C(C(=CC(=C1)C(=O)OC)O)O)O
• InChI: InChI=1S/C13H16O5/c1-7(2)10(14)5-8-4-9(13(17)18-3)6-11(15)12(8)16/h4,6,10,14-16H,1,5H2,2-3H3
• InChI Key: KVDSAANFJMQAKH-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₆O₅
• Molecular Weight: 252.26 g/mol
• Exact Mass: 252.09977361 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.36
• H-Bond Acceptor: 5
• 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	+	0.9692	96.92%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7649	76.49%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7726	77.26%
OATP1B3 inhibitior	+	0.9538	95.38%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9124	91.24%
P-glycoprotein inhibitior	-	0.9645	96.45%
P-glycoprotein substrate	-	0.8454	84.54%
CYP3A4 substrate	-	0.5208	52.08%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8017	80.17%
CYP3A4 inhibition	-	0.9027	90.27%
CYP2C9 inhibition	-	0.7751	77.51%
CYP2C19 inhibition	-	0.7257	72.57%
CYP2D6 inhibition	-	0.7740	77.40%
CYP1A2 inhibition	-	0.7151	71.51%
CYP2C8 inhibition	-	0.6243	62.43%
CYP inhibitory promiscuity	-	0.8532	85.32%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8050	80.50%
Carcinogenicity (trinary)	Non-required	0.7514	75.14%
Eye corrosion	-	0.9731	97.31%
Eye irritation	+	0.5855	58.55%
Skin irritation	-	0.6021	60.21%
Skin corrosion	-	0.9139	91.39%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4592	45.92%
Micronuclear	+	0.5277	52.77%
Hepatotoxicity	-	0.6284	62.84%
skin sensitisation	-	0.5894	58.94%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.7212	72.12%
Acute Oral Toxicity (c)	III	0.5619	56.19%
Estrogen receptor binding	-	0.5452	54.52%
Androgen receptor binding	-	0.7015	70.15%
Thyroid receptor binding	-	0.6005	60.05%
Glucocorticoid receptor binding	+	0.5966	59.66%
Aromatase binding	-	0.7038	70.38%
PPAR gamma	-	0.7606	76.06%
Honey bee toxicity	-	0.8968	89.68%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	+	0.9874	98.74%

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	99.15%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.59%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.48%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.91%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	88.86%	94.73%
CHEMBL4208	P20618	Proteasome component C5	86.12%	90.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.05%	91.07%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	83.90%	97.21%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.54%	96.95%
CHEMBL1255126	O15151	Protein Mdm4	82.59%	90.20%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.42%	96.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.89%	94.00%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	80.89%	95.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.86%	86.33%

Plants that contains it

• Piper glabratum

Cross-Links

• PubChem: 25058113
• LOTUS: LTS0115104
• wikiData: Q105146478