Phe-Trp-Ala

Details

• Internal ID: 7133d1c5-28b2-49fc-a468-bd655f7d60ff
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides > Oligopeptides
• IUPAC Name: (2S)-2-[[(2S)-2-[[(2S)-2-amino-3-phenylpropanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]propanoic acid
• SMILES (Canonical): CC(C(=O)O)NC(=O)C(CC1=CNC2=CC=CC=C21)NC(=O)C(CC3=CC=CC=C3)N
• SMILES (Isomeric): C[C@@H](C(=O)O)NC(=O)[C@H](CC1=CNC2=CC=CC=C21)NC(=O)[C@H](CC3=CC=CC=C3)N
• InChI: InChI=1S/C23H26N4O4/c1-14(23(30)31)26-22(29)20(12-16-13-25-19-10-6-5-9-17(16)19)27-21(28)18(24)11-15-7-3-2-4-8-15/h2-10,13-14,18,20,25H,11-12,24H2,1H3,(H,26,29)(H,27,28)(H,30,31)/t14-,18-,20-/m0/s1
• InChI Key: BPIFSOUEUYDJRM-DCPHZVHLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₆N₄O₄
• Molecular Weight: 422.50 g/mol
• Exact Mass: 422.19540532 g/mol
• Topological Polar Surface Area (TPSA): 137.00 Ų
• XlogP: -1.00
• Atomic LogP (AlogP): 1.35
• H-Bond Acceptor: 4
• H-Bond Donor: 5
• Rotatable Bonds: 9

Synonyms

• L-Phe-L-Trp-L-Ala
• F-W-A
• CHEBI:73640
• L-phenylalanyl-L-tryptophyl-L-alanine
• L-Phenylalanyl-L-tryptophanyl-L-alanine
• (2S)-2-(((2S)-2-(((2S)-2-amino-3-phenylpropanoyl)amino)-3-(1H-indol-3-yl)propanoyl)amino)propanoic acid
• (2S)-2-[[(2S)-2-[[(2S)-2-amino-3-phenylpropanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]propanoic acid
• RefChem:172496
• Phenylalanyl-tryptophanyl-alanine
• SCHEMBL29507360
• Q27143594

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9447	94.47%
Caco-2	-	0.8762	87.62%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5283	52.83%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9496	94.96%
OATP1B3 inhibitior	+	0.9461	94.61%
MATE1 inhibitior	-	0.9609	96.09%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.9566	95.66%
P-glycoprotein inhibitior	-	0.6418	64.18%
P-glycoprotein substrate	+	0.6428	64.28%
CYP3A4 substrate	+	0.5577	55.77%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7888	78.88%
CYP3A4 inhibition	-	0.8962	89.62%
CYP2C9 inhibition	-	0.8928	89.28%
CYP2C19 inhibition	-	0.8804	88.04%
CYP2D6 inhibition	-	0.9099	90.99%
CYP1A2 inhibition	-	0.8712	87.12%
CYP2C8 inhibition	-	0.8420	84.20%
CYP inhibitory promiscuity	-	0.8766	87.66%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8200	82.00%
Carcinogenicity (trinary)	Non-required	0.6531	65.31%
Eye corrosion	-	0.9954	99.54%
Eye irritation	-	0.9932	99.32%
Skin irritation	-	0.8484	84.84%
Skin corrosion	-	0.9636	96.36%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6769	67.69%
Micronuclear	+	0.8100	81.00%
Hepatotoxicity	-	0.6641	66.41%
skin sensitisation	-	0.9262	92.62%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.8359	83.59%
Acute Oral Toxicity (c)	III	0.5423	54.23%
Estrogen receptor binding	+	0.5991	59.91%
Androgen receptor binding	-	0.4832	48.32%
Thyroid receptor binding	-	0.6176	61.76%
Glucocorticoid receptor binding	+	0.6142	61.42%
Aromatase binding	-	0.5751	57.51%
PPAR gamma	+	0.5835	58.35%
Honey bee toxicity	-	0.8833	88.33%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.7849	78.49%
Fish aquatic toxicity	+	0.6600	66.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.39%	98.95%
CHEMBL1255126	O15151	Protein Mdm4	97.13%	90.20%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.12%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.56%	91.11%
CHEMBL3837	P07711	Cathepsin L	95.88%	96.61%
CHEMBL221	P23219	Cyclooxygenase-1	95.06%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.97%	95.56%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	92.85%	92.29%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	90.82%	97.23%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	89.23%	95.50%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	89.12%	98.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.86%	94.45%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	87.48%	97.64%
CHEMBL2535	P11166	Glucose transporter	86.86%	98.75%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	86.16%	100.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	85.99%	97.21%
CHEMBL4816	Q9Y243	Serine/threonine-protein kinase AKT3	84.05%	96.28%
CHEMBL3310	Q96DB2	Histone deacetylase 11	84.04%	88.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.98%	99.17%
CHEMBL1287628	Q9Y5S8	NADPH oxidase 1	83.76%	95.48%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	83.28%	83.10%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.19%	96.95%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	81.56%	94.62%
CHEMBL2431	P31751	Serine/threonine-protein kinase AKT2	81.04%	98.33%
CHEMBL1808	P12821	Angiotensin-converting enzyme	80.98%	93.39%
CHEMBL5028	O14672	ADAM10	80.70%	97.50%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 71728356
• LOTUS: LTS0005766
• wikiData: Q27143594