ethyl 3,4-dihydroxy-5-[(2R)-2-hydroxy-3-methylbut-3-enyl]benzoate

Details

• Internal ID: a37dafe4-41a5-4c26-a401-7f151fc24560
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzoic acids and derivatives > p-Hydroxybenzoic acid esters > p-Hydroxybenzoic acid alkyl esters
• IUPAC Name: ethyl 3,4-dihydroxy-5-[(2R)-2-hydroxy-3-methylbut-3-enyl]benzoate
• SMILES (Canonical): CCOC(=O)C1=CC(=C(C(=C1)O)O)CC(C(=C)C)O
• SMILES (Isomeric): CCOC(=O)C1=CC(=C(C(=C1)O)O)C[C@H](C(=C)C)O
• InChI: InChI=1S/C14H18O5/c1-4-19-14(18)10-5-9(6-11(15)8(2)3)13(17)12(16)7-10/h5,7,11,15-17H,2,4,6H2,1,3H3/t11-/m1/s1
• InChI Key: FBWJQVPCOKDVIM-LLVKDONJSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₈O₅
• Molecular Weight: 266.29 g/mol
• Exact Mass: 266.11542367 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 1.75
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9830	98.30%
Caco-2	-	0.5393	53.93%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8821	88.21%
OATP2B1 inhibitior	-	0.8546	85.46%
OATP1B1 inhibitior	+	0.8334	83.34%
OATP1B3 inhibitior	+	0.9612	96.12%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.8318	83.18%
P-glycoprotein inhibitior	-	0.9325	93.25%
P-glycoprotein substrate	-	0.9042	90.42%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8017	80.17%
CYP3A4 inhibition	-	0.8012	80.12%
CYP2C9 inhibition	-	0.6520	65.20%
CYP2C19 inhibition	-	0.7144	71.44%
CYP2D6 inhibition	-	0.7614	76.14%
CYP1A2 inhibition	+	0.5083	50.83%
CYP2C8 inhibition	-	0.5653	56.53%
CYP inhibitory promiscuity	-	0.7826	78.26%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8107	81.07%
Carcinogenicity (trinary)	Non-required	0.7520	75.20%
Eye corrosion	-	0.9890	98.90%
Eye irritation	+	0.6714	67.14%
Skin irritation	-	0.6906	69.06%
Skin corrosion	-	0.9238	92.38%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5171	51.71%
Micronuclear	-	0.6075	60.75%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	+	0.5197	51.97%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.7806	78.06%
Acute Oral Toxicity (c)	III	0.6291	62.91%
Estrogen receptor binding	+	0.6456	64.56%
Androgen receptor binding	-	0.5673	56.73%
Thyroid receptor binding	-	0.5737	57.37%
Glucocorticoid receptor binding	+	0.7492	74.92%
Aromatase binding	-	0.4948	49.48%
PPAR gamma	-	0.6846	68.46%
Honey bee toxicity	-	0.9041	90.41%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.9947	99.47%

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	94.69%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.71%	98.95%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	93.43%	97.21%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.16%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	92.07%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.50%	99.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	88.60%	96.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.01%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.55%	94.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.78%	95.50%
CHEMBL4208	P20618	Proteasome component C5	81.03%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.80%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.72%	90.71%
CHEMBL1951	P21397	Monoamine oxidase A	80.49%	91.49%

Plants that contains it

• Piper glabratum

Cross-Links

• PubChem: 163007224
• LOTUS: LTS0259038
• wikiData: Q104992984