Ethyl 2,4-dihydroxy-6-methylbenzoate

Details

• Internal ID: 67964404-c1c9-4c6c-8ef3-5a7fcebcace0
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzoic acids and derivatives > p-Hydroxybenzoic acid esters > p-Hydroxybenzoic acid alkyl esters
• IUPAC Name: ethyl 2,4-dihydroxy-6-methylbenzoate
• SMILES (Canonical): CCOC(=O)C1=C(C=C(C=C1C)O)O
• SMILES (Isomeric): CCOC(=O)C1=C(C=C(C=C1C)O)O
• InChI: InChI=1S/C10H12O4/c1-3-14-10(13)9-6(2)4-7(11)5-8(9)12/h4-5,11-12H,3H2,1-2H3
• InChI Key: UQSRXQMIXSZGLA-UHFFFAOYSA-N
• Popularity: 41 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₂O₄
• Molecular Weight: 196.20 g/mol
• Exact Mass: 196.07355886 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 1.58
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 2524-37-0
• Ethyl orsellinate
• Orsellinic acid, ethyl ester
• Benzoic acid, 2,4-dihydroxy-6-methyl-, ethyl ester
• o-Orsellinic acid, ethyl ester
• 2,4-Dihydroxy-6-methylbenzoic Acid Ethyl Ester
• orsellinic acid ethyl ester
• UNII-3035H4GP23
• .beta.-Resorcylic acid, 6-methyl-, ethyl ester
• 3035H4GP23
• NSC 149781
• NSC-149781
• 2,4-DIHYDROXY-6-METHYLBENZOICACIDETHYLESTER
• Spectrum_000785
• SpecPlus_000248
• Spectrum2_000390
• Spectrum3_000694
• Spectrum4_001427
• Spectrum5_000254
• BSPBio_002447
• KBioGR_001874
• KBioSS_001265
• SPECTRUM200002
• MLS002695995
• DivK1c_006344
• SPBio_000579
• SCHEMBL1648471
• 4-Carbethoxy-5-methylresorcinol
• CHEMBL1601166
• DTXSID4062488
• KBio1_001288
• KBio2_001265
• KBio2_003833
• KBio2_006401
• KBio3_001667
• CHEBI:113535
• 2-Carbethoxy-3,5-dihydroxytoluene
• 4-Ethoxycarbonyl-5-methylresorcinol
• .beta.-Resorcylic acid, ethyl ester
• CCG-38661
• MFCD00010821
• NSC149781
• s5128
• 2-Ethoxycarbonyl-3,5-dihydroxytoluene
• AKOS015889573
• CS-W000427
• HY-W000427
• SDCCGMLS-0066439.P001
• NCGC00095458-01
• NCGC00095458-02
• SMR001562139
• TS-02774
• Ethyl 2,4-dihydroxy-6-methylbenzoate, 98%
• FT-0634342
• ss-Resorcylic acid, 6-methyl-, ethyl ester
• beta-Resorcylic acid, 6-methyl-, ethyl ester
• 2,4-Dihydroxy-6-methyl-benzoic acid ethyl ester
• Benzoic acid,4-dihydroxy-6-methyl-, ethyl ester
• SR-05000002432
• J-015886
• SR-05000002432-1
• BRD-K97487499-001-02-2
• Q27194425
• InChI=1/C10H12O4/c1-3-14-10(13)9-6(2)4-7(11)5-8(9)12/h4-5,11-12H,3H2,1-2H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9730	97.30%
Caco-2	+	0.8241	82.41%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.9184	91.84%
OATP2B1 inhibitior	-	0.8582	85.82%
OATP1B1 inhibitior	+	0.9649	96.49%
OATP1B3 inhibitior	+	0.9693	96.93%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9131	91.31%
P-glycoprotein inhibitior	-	0.9601	96.01%
P-glycoprotein substrate	-	0.9744	97.44%
CYP3A4 substrate	-	0.5761	57.61%
CYP2C9 substrate	-	0.7977	79.77%
CYP2D6 substrate	-	0.8718	87.18%
CYP3A4 inhibition	-	0.8420	84.20%
CYP2C9 inhibition	-	0.6824	68.24%
CYP2C19 inhibition	-	0.5683	56.83%
CYP2D6 inhibition	-	0.9318	93.18%
CYP1A2 inhibition	-	0.6542	65.42%
CYP2C8 inhibition	-	0.6085	60.85%
CYP inhibitory promiscuity	-	0.6173	61.73%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7300	73.00%
Carcinogenicity (trinary)	Non-required	0.8159	81.59%
Eye corrosion	-	0.9431	94.31%
Eye irritation	+	0.9897	98.97%
Skin irritation	-	0.5717	57.17%
Skin corrosion	-	0.9564	95.64%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6998	69.98%
Micronuclear	-	0.6167	61.67%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	+	0.5772	57.72%
Respiratory toxicity	-	0.7333	73.33%
Reproductive toxicity	-	0.5778	57.78%
Mitochondrial toxicity	-	0.7000	70.00%
Nephrotoxicity	-	0.5814	58.14%
Acute Oral Toxicity (c)	III	0.8560	85.60%
Estrogen receptor binding	+	0.8036	80.36%
Androgen receptor binding	-	0.5270	52.70%
Thyroid receptor binding	-	0.7676	76.76%
Glucocorticoid receptor binding	-	0.7097	70.97%
Aromatase binding	-	0.5631	56.31%
PPAR gamma	-	0.7715	77.15%
Honey bee toxicity	-	0.9546	95.46%
Biodegradation	+	0.5500	55.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9645	96.45%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL340	P08684	Cytochrome P450 3A4	25118.9 nM; 25118.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	25118.9 nM	Potency	via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	1000 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.09%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	91.96%	94.73%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	88.88%	93.65%
CHEMBL2581	P07339	Cathepsin D	87.42%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.00%	91.11%
CHEMBL4208	P20618	Proteasome component C5	85.89%	90.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.72%	96.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.46%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.45%	86.33%
CHEMBL1929	P47989	Xanthine dehydrogenase	83.44%	96.12%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	83.02%	97.21%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.83%	94.00%
CHEMBL3194	P02766	Transthyretin	81.12%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.19%	95.56%

Plants that contains it

• Calypogeia integristipula
• Cirsium brevistylum
• Diospyros maritima
• Euonymus alatus
• Gentiana dahurica
• Gymnanthemum amygdalinum
• Hylodesmum podocarpum subsp. oxyphyllum
• Putterlickia verrucosa
• Sideritis marmorea

Cross-Links

• PubChem: 75653
• NPASS: NPC153783
• ChEMBL: CHEMBL1601166
• LOTUS: LTS0242382
• wikiData: Q27194425