N-Acetyl-L-phenylalanine

Details

• Internal ID: de6ff34a-f2b9-444b-a764-f4733abb61db
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Phenylalanine and derivatives
• IUPAC Name: (2S)-2-acetamido-3-phenylpropanoic acid
• SMILES (Canonical): CC(=O)NC(CC1=CC=CC=C1)C(=O)O
• SMILES (Isomeric): CC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O
• InChI: InChI=1S/C11H13NO3/c1-8(13)12-10(11(14)15)7-9-5-3-2-4-6-9/h2-6,10H,7H2,1H3,(H,12,13)(H,14,15)/t10-/m0/s1
• InChI Key: CBQJSKKFNMDLON-JTQLQIEISA-N
• Popularity: 278 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₃NO₃
• Molecular Weight: 207.23 g/mol
• Exact Mass: 207.08954328 g/mol
• Topological Polar Surface Area (TPSA): 66.40 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 0.82
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• 2018-61-3
• Acetyl-L-phenylalanine
• L-Phenylalanine, N-acetyl-
• L-N-Acetylphenylalanine
• (2S)-2-acetamido-3-phenylpropanoic acid
• acetylphenylalanine
• Alanine, N-acetyl-3-phenyl-, L-
• NP5BT39467
• CHEBI:16259
• DTXSID20883539
• NSC-45699
• CHEBI:21626
• RefChem:927006
• DTXCID901023062
• 217-959-8
• (2S)-2-acetamido-3-phenylpropanoate
• N-Acetylphenylalanine
• Ac-Phe-OH
• (S)-2-Acetamido-3-phenylpropanoic acid
• MFCD00063158
• Phenylalanine, N-acetyl-
• N-Acetyl-3-phenyl-L-alanine
• N-Acetyl-l-phenalanine
• NSC 45699
• (2S)-2-(acetylamino)-3-phenylpropanoic acid
• M02987
• UNII-NP5BT39467
• 5CR
• EINECS 217-959-8
• N-Ac-L-Phe
• N-Acetyl Phenylalanine
• N-Acetyl-Phenylalanine
• N-Acetyl L-phenylalanine
• Maybridge1_002391
• AFALANINE, (S)-
• N-Acetyl-(S)-phenylalanine
• DivK1c_001143
• SCHEMBL158613
• (S)-2-(ACETYLAMINO)-3-PHENYLPROPANOIC ACID
• ACETYLPHENYLALANINE, L-
• HMS548E15
• HY-Y0068R
• MSK2368
• N-ACETYLPHENYLALANINE, L-
• (+)-N-ACETYLPHENYLALANINE
• HMS3264C06
• Pharmakon1600-01506105
• HY-Y0068
• CCG-46423
• EBC-03687
• N-Acetyl-L-phenylalanine (Standard)
• NSC760131
• s6362
• SBB028538
• (+)-N-ACETYL-L-PHENYLALANINE
• AKOS001051290
• AKOS015837745
• CS-W020567
• FA37492
• NSC-760131
• CDS1_000103
• NCGC00264266-02
• AC-24138
• BP-12302
• SY018098
• TS-00391
• (S)-2-acetylamino-3-phenyl-propionic acid
• A1541
• NS00014789
• (E)-N-(1-Hydroxyethylidene)-L-phenylalanine
• C03519
• EN300-937150
• AB01209616-01
• AB01209616-04
• AB01209616_05
• N-Acetyl-L-phenylalanine, ReagentPlus(R), 99%
• 018A613
• SR-01000636121-1
• BRD-K53205568-001-01-8
• BRD-K53205568-001-02-6
• Q27101819
• Z56968155
• N-Acetyl-L-phenylalanine, Vetec(TM) reagent grade, 98%
• 545BBBE7-685F-4C55-87D5-4AB08113ECE0

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9580	95.80%
Caco-2	-	0.8273	82.73%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7550	75.50%
OATP2B1 inhibitior	-	0.8625	86.25%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9545	95.45%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8526	85.26%
P-glycoprotein inhibitior	-	0.9840	98.40%
P-glycoprotein substrate	-	0.8302	83.02%
CYP3A4 substrate	-	0.6337	63.37%
CYP2C9 substrate	+	0.6265	62.65%
CYP2D6 substrate	-	0.8586	85.86%
CYP3A4 inhibition	-	0.9634	96.34%
CYP2C9 inhibition	-	0.9609	96.09%
CYP2C19 inhibition	-	0.9705	97.05%
CYP2D6 inhibition	-	0.9668	96.68%
CYP1A2 inhibition	-	0.8804	88.04%
CYP2C8 inhibition	-	0.9801	98.01%
CYP inhibitory promiscuity	-	0.9875	98.75%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7424	74.24%
Carcinogenicity (trinary)	Non-required	0.7360	73.60%
Eye corrosion	-	0.9970	99.70%
Eye irritation	-	0.9731	97.31%
Skin irritation	-	0.8071	80.71%
Skin corrosion	-	0.9664	96.64%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7765	77.65%
Micronuclear	+	0.6200	62.00%
Hepatotoxicity	-	0.5657	56.57%
skin sensitisation	-	0.9110	91.10%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.5242	52.42%
Acute Oral Toxicity (c)	IV	0.5011	50.11%
Estrogen receptor binding	-	0.8786	87.86%
Androgen receptor binding	-	0.8026	80.26%
Thyroid receptor binding	-	0.9393	93.93%
Glucocorticoid receptor binding	-	0.6598	65.98%
Aromatase binding	-	0.6334	63.34%
PPAR gamma	-	0.7825	78.25%
Honey bee toxicity	-	0.9679	96.79%
Biodegradation	-	0.5000	50.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.6478	64.78%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.92%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	98.20%	90.17%
CHEMBL1255126	O15151	Protein Mdm4	94.79%	90.20%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	90.30%	95.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.48%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.67%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.65%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.32%	91.11%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	82.03%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	81.65%	94.73%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 74839
• LOTUS: LTS0151653
• wikiData: Q27101819