3-Methyl-4-(2,3-dihydroxyphenyl)-4-oxo-butanoic acid

Details

• Internal ID: 7caa15df-5e23-4779-8961-69711027701e
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Phenylketones > Alkyl-phenylketones
• IUPAC Name: 4-(2,3-dihydroxyphenyl)-3-methyl-4-oxobutanoic acid
• SMILES (Canonical): CC(CC(=O)O)C(=O)C1=C(C(=CC=C1)O)O
• SMILES (Isomeric): CC(CC(=O)O)C(=O)C1=C(C(=CC=C1)O)O
• InChI: InChI=1S/C11H12O5/c1-6(5-9(13)14)10(15)7-3-2-4-8(12)11(7)16/h2-4,6,12,16H,5H2,1H3,(H,13,14)
• InChI Key: SGNALGPYOOQHOT-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₂O₅
• Molecular Weight: 224.21 g/mol
• Exact Mass: 224.06847348 g/mol
• Topological Polar Surface Area (TPSA): 94.80 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.39
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• 3-Methyl-4-(2,3-dihydroxyphenyl)-4-oxo-butanoic acid
• 4-(2,3-Dihydroxyphenyl)-3-methyl-4-oxobutanoic acid #

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9319	93.19%
Caco-2	-	0.7294	72.94%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	+	0.8286	82.86%
Subcellular localzation	Mitochondria	0.8211	82.11%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9200	92.00%
OATP1B3 inhibitior	+	0.9572	95.72%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9016	90.16%
P-glycoprotein inhibitior	-	0.9923	99.23%
P-glycoprotein substrate	-	0.8689	86.89%
CYP3A4 substrate	-	0.7118	71.18%
CYP2C9 substrate	+	0.5853	58.53%
CYP2D6 substrate	-	0.8791	87.91%
CYP3A4 inhibition	-	0.9524	95.24%
CYP2C9 inhibition	-	0.9477	94.77%
CYP2C19 inhibition	-	0.9776	97.76%
CYP2D6 inhibition	-	0.9174	91.74%
CYP1A2 inhibition	-	0.8847	88.47%
CYP2C8 inhibition	-	0.9092	90.92%
CYP inhibitory promiscuity	-	0.9910	99.10%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7342	73.42%
Carcinogenicity (trinary)	Non-required	0.7125	71.25%
Eye corrosion	-	0.9254	92.54%
Eye irritation	+	0.7914	79.14%
Skin irritation	+	0.5425	54.25%
Skin corrosion	-	0.6823	68.23%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.9005	90.05%
Micronuclear	+	0.6459	64.59%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	+	0.5855	58.55%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	-	0.7237	72.37%
Acute Oral Toxicity (c)	III	0.6845	68.45%
Estrogen receptor binding	-	0.8781	87.81%
Androgen receptor binding	-	0.6033	60.33%
Thyroid receptor binding	-	0.8261	82.61%
Glucocorticoid receptor binding	-	0.5354	53.54%
Aromatase binding	-	0.9393	93.93%
PPAR gamma	-	0.6042	60.42%
Honey bee toxicity	-	0.9849	98.49%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.9200	92.00%
Fish aquatic toxicity	+	0.9469	94.69%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.69%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.84%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.01%	91.11%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	90.19%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.92%	95.56%
CHEMBL3359	P21462	Formyl peptide receptor 1	89.38%	93.56%
CHEMBL1907588	P02708	Acetylcholine receptor; alpha1/beta1/delta/gamma	88.49%	98.33%
CHEMBL3401	O75469	Pregnane X receptor	87.51%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.10%	99.15%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.59%	95.50%
CHEMBL221	P23219	Cyclooxygenase-1	84.40%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.07%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.88%	86.33%

Plants that contains it

• Plumbago zeylanica
• Thuja plicata

Cross-Links

• PubChem: 586465
• NPASS: NPC254407