Ethyl 3,4-dihydroxybenzoate

Details

• Internal ID: 64ef4552-95aa-4678-ac27-f5c660f3dd55
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzoic acids and derivatives > p-Hydroxybenzoic acid esters > p-Hydroxybenzoic acid alkyl esters
• IUPAC Name: ethyl 3,4-dihydroxybenzoate
• SMILES (Canonical): CCOC(=O)C1=CC(=C(C=C1)O)O
• SMILES (Isomeric): CCOC(=O)C1=CC(=C(C=C1)O)O
• InChI: InChI=1S/C9H10O4/c1-2-13-9(12)6-3-4-7(10)8(11)5-6/h3-5,10-11H,2H2,1H3
• InChI Key: KBPUBCVJHFXPOC-UHFFFAOYSA-N
• Popularity: 179 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₀O₄
• Molecular Weight: 182.17 g/mol
• Exact Mass: 182.05790880 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.27
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 3943-89-3
• Ethyl protocatechuate
• 3,4-Dihydroxybenzoic Acid Ethyl Ester
• Protocatechuic acid ethyl ester
• Benzoic acid, 3,4-dihydroxy-, ethyl ester
• MFCD00002199
• UNII-4YGJ96WTBG
• 4YGJ96WTBG
• CHEMBL486216
• DTXSID2057732
• EINECS 223-529-0
• NSC 86130
• NSC-86130
• Ethyl-3,4-dihydroxybenzoate
• EC 223-529-0
• EDHB
• 3,4-DHBEEOP
• 3,4-dihydroxyethyl benzoate
• SCHEMBL39791
• Ethyl-3,4-dihydroxy-benzoate
• DTXCID3031521
• Protocatechuic acid, ethyl ester
• CHEBI:132364
• AMY40110
• BCP26356
• NSC86130
• Tox21_113836
• BDBM50428394
• NSC619681
• AKOS015856218
• Protocatechuic acid ethyl ester, 97%
• AC-9614
• CS-W017125
• FD16015
• HY-W016409
• NSC-619681
• PS-4053
• 3,4-Dihydroxy-benzoic acid ethyl ester
• 3,4-Dihydroxybenzoic acid, ethyl ester
• Benzoic acid,4-dihydroxy-, ethyl ester
• NCGC00253717-01
• SY017737
• CAS-3943-89-3
• A6602
• D0571
• FT-0625754
• SR-01000944711
• Q3277971
• SR-01000944711-1
• W-106433
• F0001-1109
• InChI=1/C9H10O4/c1-2-13-9(12)6-3-4-7(10)8(11)5-6/h3-5,10-11H,2H2,1H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9750	97.50%
Caco-2	+	0.5169	51.69%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.9358	93.58%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9501	95.01%
OATP1B3 inhibitior	+	0.9648	96.48%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9579	95.79%
P-glycoprotein inhibitior	-	0.9789	97.89%
P-glycoprotein substrate	-	0.9824	98.24%
CYP3A4 substrate	-	0.6445	64.45%
CYP2C9 substrate	-	0.6017	60.17%
CYP2D6 substrate	-	0.8370	83.70%
CYP3A4 inhibition	-	0.9591	95.91%
CYP2C9 inhibition	-	0.7250	72.50%
CYP2C19 inhibition	-	0.8823	88.23%
CYP2D6 inhibition	-	0.9512	95.12%
CYP1A2 inhibition	-	0.7518	75.18%
CYP2C8 inhibition	+	0.4867	48.67%
CYP inhibitory promiscuity	-	0.8485	84.85%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7170	71.70%
Carcinogenicity (trinary)	Non-required	0.6657	66.57%
Eye corrosion	-	0.9310	93.10%
Eye irritation	+	0.9905	99.05%
Skin irritation	+	0.5315	53.15%
Skin corrosion	-	0.8918	89.18%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8026	80.26%
Micronuclear	+	0.5088	50.88%
Hepatotoxicity	-	0.5447	54.47%
skin sensitisation	+	0.5087	50.87%
Respiratory toxicity	-	0.6889	68.89%
Reproductive toxicity	-	0.5778	57.78%
Mitochondrial toxicity	-	0.7875	78.75%
Nephrotoxicity	-	0.6604	66.04%
Acute Oral Toxicity (c)	III	0.8197	81.97%
Estrogen receptor binding	+	0.7747	77.47%
Androgen receptor binding	+	0.5260	52.60%
Thyroid receptor binding	-	0.7674	76.74%
Glucocorticoid receptor binding	-	0.5679	56.79%
Aromatase binding	-	0.5085	50.85%
PPAR gamma	-	0.8468	84.68%
Honey bee toxicity	-	0.9695	96.95%
Biodegradation	+	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7250	72.50%
Fish aquatic toxicity	+	0.9630	96.30%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL261	P00915	Carbonic anhydrase I	650 nM; 650 nM	Ki; Ki	PMID: 22668600; via Super-PRED
CHEMBL205	P00918	Carbonic anhydrase II	610 nM; 610 nM	Ki; Ki	PMID: 22668600; via Super-PRED
CHEMBL3594	Q16790	Carbonic anhydrase IX	780 nM; 780 nM	Ki; Ki	PMID: 22668600; via Super-PRED
CHEMBL2326	P43166	Carbonic anhydrase VII	750 nM; 750 nM	Ki; Ki	PMID: 22668600; via Super-PRED
CHEMBL3242	O43570	Carbonic anhydrase XII	830 nM; 830 nM	Ki; Ki	PMID: 22668600; via Super-PRED
CHEMBL3510	Q9ULX7	Carbonic anhydrase XIV	860 nM; 860 nM	Ki; Ki	via Super-PRED; PMID: 22668600

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	93.61%	91.49%
CHEMBL4208	P20618	Proteasome component C5	89.21%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.10%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.79%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.56%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	86.54%	94.73%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	86.34%	97.21%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.00%	91.11%
CHEMBL2581	P07339	Cathepsin D	85.75%	98.95%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.52%	96.95%
CHEMBL3194	P02766	Transthyretin	83.73%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.04%	95.56%

Plants that contains it

• Abrus melanospermus subsp. melanospermus
• Acacia confusa
• Arachis hypogaea
• Canarium album
• Chaenomeles sinensis
• Leucaena leucocephala
• Rhaponticoides africana
• Rumex chalepensis
• Rumex japonicus
• Spatholobus suberectus
• Tadehagi triquetrum
• Xanthium strumarium subsp. strumarium
• Xylocarpus granatum

Cross-Links

• PubChem: 77547
• NPASS: NPC226855
• ChEMBL: CHEMBL486216
• LOTUS: LTS0006328
• wikiData: Q3277971