2-Acetyl-4-hydroxy-3-methoxybenzoic acid

Details

• Internal ID: c887da4a-050f-403b-b854-ca6658ad6f48
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Phenylketones > Alkyl-phenylketones
• IUPAC Name: 2-acetyl-4-hydroxy-3-methoxybenzoic acid
• SMILES (Canonical): CC(=O)C1=C(C=CC(=C1OC)O)C(=O)O
• SMILES (Isomeric): CC(=O)C1=C(C=CC(=C1OC)O)C(=O)O
• InChI: InChI=1S/C10H10O5/c1-5(11)8-6(10(13)14)3-4-7(12)9(8)15-2/h3-4,12H,1-2H3,(H,13,14)
• InChI Key: GMYHGDFFXVALJH-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₀O₅
• Molecular Weight: 210.18 g/mol
• Exact Mass: 210.05282342 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.30
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• 93762-15-3
• EINECS 297-729-1
• Acetylvanillinsaure
• acetyl vanillic acid
• SCHEMBL111734
• DTXSID40239574
• GMYHGDFFXVALJH-UHFFFAOYSA-N

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9486	94.86%
Caco-2	-	0.6377	63.77%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8795	87.95%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9694	96.94%
OATP1B3 inhibitior	+	0.9329	93.29%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9833	98.33%
P-glycoprotein inhibitior	-	0.9460	94.60%
P-glycoprotein substrate	-	0.9706	97.06%
CYP3A4 substrate	-	0.7500	75.00%
CYP2C9 substrate	-	0.5842	58.42%
CYP2D6 substrate	-	0.8541	85.41%
CYP3A4 inhibition	-	0.9719	97.19%
CYP2C9 inhibition	-	0.9023	90.23%
CYP2C19 inhibition	-	0.9189	91.89%
CYP2D6 inhibition	-	0.9147	91.47%
CYP1A2 inhibition	-	0.9035	90.35%
CYP2C8 inhibition	-	0.8680	86.80%
CYP inhibitory promiscuity	-	0.9504	95.04%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.6884	68.84%
Carcinogenicity (trinary)	Non-required	0.7273	72.73%
Eye corrosion	-	0.6659	66.59%
Eye irritation	+	0.9783	97.83%
Skin irritation	+	0.5446	54.46%
Skin corrosion	-	0.8751	87.51%
Ames mutagenesis	-	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7707	77.07%
Micronuclear	+	0.7000	70.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.8472	84.72%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	-	0.7000	70.00%
Nephrotoxicity	+	0.5275	52.75%
Acute Oral Toxicity (c)	II	0.6071	60.71%
Estrogen receptor binding	-	0.5145	51.45%
Androgen receptor binding	-	0.7339	73.39%
Thyroid receptor binding	-	0.7949	79.49%
Glucocorticoid receptor binding	-	0.7613	76.13%
Aromatase binding	-	0.8374	83.74%
PPAR gamma	-	0.8431	84.31%
Honey bee toxicity	-	0.9587	95.87%
Biodegradation	+	0.6250	62.50%
Crustacea aquatic toxicity	-	0.9300	93.00%
Fish aquatic toxicity	+	0.9355	93.55%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.03%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.91%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	90.24%	83.82%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.93%	99.15%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	84.76%	94.08%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.94%	95.50%
CHEMBL2581	P07339	Cathepsin D	82.79%	98.95%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	82.16%	87.67%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.04%	94.45%
CHEMBL2535	P11166	Glucose transporter	81.39%	98.75%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	81.17%	94.42%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.11%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.69%	86.33%

Plants that contains it

• Buddleja cordata

Cross-Links

• PubChem: 3022207
• LOTUS: LTS0238231
• wikiData: Q83121955