2-Amino-3-(4-hydroxyphenyl)-propanoic acid

Details

• Internal ID: 8a8e1066-189f-4248-8355-6fc66e91b92e
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Tyrosine and derivatives
• IUPAC Name: (2R)-2-azaniumyl-3-(4-hydroxyphenyl)propanoate
• SMILES (Canonical): C1=CC(=CC=C1CC(C(=O)[O-])[NH3+])O
• SMILES (Isomeric): C1=CC(=CC=C1C[C@H](C(=O)[O-])[NH3+])O
• InChI: InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13)/t8-/m1/s1
• InChI Key: OUYCCCASQSFEME-MRVPVSSYSA-N
• Popularity: 10 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₁NO₃
• Molecular Weight: 181.19 g/mol
• Exact Mass: 181.07389321 g/mol
• Topological Polar Surface Area (TPSA): 88.00 Ų
• XlogP: -1.60
• Atomic LogP (AlogP): -1.70
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• 2-amino-3-(4-hydroxyphenyl)-propanoic acid
• CHEBI:58570
• (2R)-2-ammonio-3-(4-hydroxyphenyl)propanoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9877	98.77%
Caco-2	+	0.5662	56.62%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6702	67.02%
OATP2B1 inhibitior	-	0.8663	86.63%
OATP1B1 inhibitior	+	0.9241	92.41%
OATP1B3 inhibitior	+	0.9481	94.81%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9206	92.06%
P-glycoprotein inhibitior	-	0.9927	99.27%
P-glycoprotein substrate	-	0.9280	92.80%
CYP3A4 substrate	-	0.6725	67.25%
CYP2C9 substrate	-	0.6136	61.36%
CYP2D6 substrate	-	0.8073	80.73%
CYP3A4 inhibition	-	0.9691	96.91%
CYP2C9 inhibition	-	0.9777	97.77%
CYP2C19 inhibition	-	0.9177	91.77%
CYP2D6 inhibition	-	0.9298	92.98%
CYP1A2 inhibition	-	0.9486	94.86%
CYP2C8 inhibition	-	0.8054	80.54%
CYP inhibitory promiscuity	-	0.9562	95.62%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.6458	64.58%
Carcinogenicity (trinary)	Non-required	0.7274	72.74%
Eye corrosion	-	0.9929	99.29%
Eye irritation	-	0.6277	62.77%
Skin irritation	-	0.5201	52.01%
Skin corrosion	-	0.9208	92.08%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8311	83.11%
Micronuclear	+	0.7474	74.74%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.5801	58.01%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.6726	67.26%
Acute Oral Toxicity (c)	III	0.6265	62.65%
Estrogen receptor binding	-	0.9338	93.38%
Androgen receptor binding	-	0.5573	55.73%
Thyroid receptor binding	-	0.8761	87.61%
Glucocorticoid receptor binding	-	0.7793	77.93%
Aromatase binding	-	0.9025	90.25%
PPAR gamma	-	0.7324	73.24%
Honey bee toxicity	-	0.9110	91.10%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	-	0.5698	56.98%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	94.88%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.22%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.24%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.23%	94.45%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	86.66%	97.21%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	85.81%	91.71%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.86%	96.95%
CHEMBL1255126	O15151	Protein Mdm4	82.66%	90.20%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.96%	95.56%
CHEMBL1944	P08473	Neprilysin	81.79%	92.63%
CHEMBL2535	P11166	Glucose transporter	80.87%	98.75%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	80.74%	100.00%

Plants that contains it

• Allium sativum
• Brassica juncea
• Ginkgo biloba
• Pinellia ternata
• Selaginella pulvinata
• Selaginella tamariscina
• Sinapis alba

Cross-Links

• PubChem: 6919035
• NPASS: NPC188867
• ChEMBL: CHEMBL1076637