2-Amino-3,4-dihydroxy-5-methoxybenzoic acid

Details

• Internal ID: 10fd612c-ce29-4910-8dcc-33ae37c3b3af
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzoic acids and derivatives > Hydroxybenzoic acid derivatives > Gallic acid and derivatives
• IUPAC Name: 2-amino-3,4-dihydroxy-5-methoxybenzoic acid
• SMILES (Canonical): COC1=C(C(=C(C(=C1)C(=O)O)N)O)O
• SMILES (Isomeric): COC1=C(C(=C(C(=C1)C(=O)O)N)O)O
• InChI: InChI=1S/C8H9NO5/c1-14-4-2-3(8(12)13)5(9)7(11)6(4)10/h2,10-11H,9H2,1H3,(H,12,13)
• InChI Key: SKSWIIXKACKGED-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₉NO₅
• Molecular Weight: 199.16 g/mol
• Exact Mass: 199.04807239 g/mol
• Topological Polar Surface Area (TPSA): 113.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 0.39
• H-Bond Acceptor: 5
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7822	78.22%
Caco-2	-	0.8747	87.47%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	+	0.8429	84.29%
Subcellular localzation	Mitochondria	0.4481	44.81%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9292	92.92%
OATP1B3 inhibitior	+	0.9621	96.21%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9443	94.43%
P-glycoprotein inhibitior	-	0.9439	94.39%
P-glycoprotein substrate	-	0.8829	88.29%
CYP3A4 substrate	-	0.7479	74.79%
CYP2C9 substrate	-	0.6034	60.34%
CYP2D6 substrate	-	0.8383	83.83%
CYP3A4 inhibition	-	0.8263	82.63%
CYP2C9 inhibition	-	0.8961	89.61%
CYP2C19 inhibition	-	0.7257	72.57%
CYP2D6 inhibition	-	0.9513	95.13%
CYP1A2 inhibition	-	0.8117	81.17%
CYP2C8 inhibition	-	0.7427	74.27%
CYP inhibitory promiscuity	-	0.9164	91.64%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7574	75.74%
Carcinogenicity (trinary)	Non-required	0.7246	72.46%
Eye corrosion	-	0.9907	99.07%
Eye irritation	+	0.9667	96.67%
Skin irritation	-	0.8589	85.89%
Skin corrosion	-	0.9721	97.21%
Ames mutagenesis	-	0.5837	58.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.8090	80.90%
Micronuclear	+	0.6500	65.00%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.8123	81.23%
Respiratory toxicity	-	0.6778	67.78%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.7044	70.44%
Acute Oral Toxicity (c)	III	0.6769	67.69%
Estrogen receptor binding	+	0.6579	65.79%
Androgen receptor binding	-	0.6505	65.05%
Thyroid receptor binding	-	0.8055	80.55%
Glucocorticoid receptor binding	+	0.6116	61.16%
Aromatase binding	-	0.7603	76.03%
PPAR gamma	-	0.7038	70.38%
Honey bee toxicity	-	0.9343	93.43%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.8200	82.00%
Fish aquatic toxicity	-	0.3816	38.16%

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	96.19%	96.09%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	93.30%	94.42%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.19%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.52%	86.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	90.88%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.65%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.50%	99.17%
CHEMBL3194	P02766	Transthyretin	85.51%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.05%	94.45%
CHEMBL1255126	O15151	Protein Mdm4	83.77%	90.20%
CHEMBL2535	P11166	Glucose transporter	81.85%	98.75%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.85%	96.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.45%	93.00%

Plants that contains it

• Cyclocarya paliurus

Cross-Links

• PubChem: 89813231
• LOTUS: LTS0105679
• wikiData: Q105255016