l-Pyroglutamyl-l-glutaminyl-l-tryptophan

Details

• Internal ID: dee7b930-5fba-4ca2-94aa-f4b1abbaf729
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides > Oligopeptides
• IUPAC Name: (2S)-2-[[(2S)-5-amino-5-oxo-2-[[(2S)-5-oxopyrrolidine-2-carbonyl]amino]pentanoyl]amino]-3-(1H-indol-3-yl)propanoic acid
• SMILES (Canonical): C1CC(=O)NC1C(=O)NC(CCC(=O)N)C(=O)NC(CC2=CNC3=CC=CC=C32)C(=O)O
• SMILES (Isomeric): C1CC(=O)N[C@@H]1C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CC2=CNC3=CC=CC=C32)C(=O)O
• InChI: InChI=1S/C21H25N5O6/c22-17(27)7-5-15(25-19(29)14-6-8-18(28)24-14)20(30)26-16(21(31)32)9-11-10-23-13-4-2-1-3-12(11)13/h1-4,10,14-16,23H,5-9H2,(H2,22,27)(H,24,28)(H,25,29)(H,26,30)(H,31,32)/t14-,15-,16-/m0/s1
• InChI Key: QLEHEZFFHZSERE-JYJNAYRXSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₅N₅O₆
• Molecular Weight: 443.50 g/mol
• Exact Mass: 443.18048353 g/mol
• Topological Polar Surface Area (TPSA): 184.00 Ų
• XlogP: -1.30
• Atomic LogP (AlogP): -0.69
• H-Bond Acceptor: 5
• H-Bond Donor: 6
• Rotatable Bonds: 10

Synonyms

• l-pyroglutamyl-l-glutaminyl-l-tryptophan

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8770	87.70%
Caco-2	-	0.9382	93.82%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5830	58.30%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9021	90.21%
OATP1B3 inhibitior	+	0.9468	94.68%
MATE1 inhibitior	-	0.9009	90.09%
OCT2 inhibitior	-	0.9433	94.33%
BSEP inhibitior	+	0.6376	63.76%
P-glycoprotein inhibitior	-	0.5231	52.31%
P-glycoprotein substrate	+	0.6032	60.32%
CYP3A4 substrate	+	0.6593	65.93%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8359	83.59%
CYP3A4 inhibition	-	0.9667	96.67%
CYP2C9 inhibition	-	0.9479	94.79%
CYP2C19 inhibition	-	0.9503	95.03%
CYP2D6 inhibition	-	0.9226	92.26%
CYP1A2 inhibition	-	0.9415	94.15%
CYP2C8 inhibition	-	0.6851	68.51%
CYP inhibitory promiscuity	-	0.9870	98.70%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.6993	69.93%
Eye corrosion	-	0.9934	99.34%
Eye irritation	-	0.9856	98.56%
Skin irritation	-	0.8396	83.96%
Skin corrosion	-	0.9399	93.99%
Ames mutagenesis	-	0.8570	85.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6906	69.06%
Micronuclear	+	0.7400	74.00%
Hepatotoxicity	+	0.5033	50.33%
skin sensitisation	-	0.9060	90.60%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.9287	92.87%
Acute Oral Toxicity (c)	III	0.6498	64.98%
Estrogen receptor binding	+	0.5643	56.43%
Androgen receptor binding	-	0.5570	55.70%
Thyroid receptor binding	-	0.5915	59.15%
Glucocorticoid receptor binding	-	0.6201	62.01%
Aromatase binding	-	0.6606	66.06%
PPAR gamma	+	0.6584	65.84%
Honey bee toxicity	-	0.8390	83.90%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7349	73.49%
Fish aquatic toxicity	-	0.8139	81.39%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.25%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	98.51%	83.82%
CHEMBL2581	P07339	Cathepsin D	98.30%	98.95%
CHEMBL3310	Q96DB2	Histone deacetylase 11	97.71%	88.56%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.34%	95.56%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	95.67%	97.64%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.97%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.56%	96.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	93.83%	82.69%
CHEMBL3192	Q9BY41	Histone deacetylase 8	93.19%	93.99%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	93.06%	83.10%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	92.32%	98.33%
CHEMBL5103	Q969S8	Histone deacetylase 10	91.76%	90.08%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	91.74%	91.81%
CHEMBL213	P08588	Beta-1 adrenergic receptor	90.19%	95.56%
CHEMBL4979	P13866	Sodium/glucose cotransporter 1	89.13%	98.24%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.37%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.17%	99.23%
CHEMBL259	P32245	Melanocortin receptor 4	87.67%	95.38%
CHEMBL1255126	O15151	Protein Mdm4	87.67%	90.20%
CHEMBL5028	O14672	ADAM10	86.72%	97.50%
CHEMBL5939	Q9NZ08	Endoplasmic reticulum aminopeptidase 1	86.72%	100.00%
CHEMBL221	P23219	Cyclooxygenase-1	86.41%	90.17%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.41%	89.62%
CHEMBL3837	P07711	Cathepsin L	86.27%	96.61%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	86.06%	94.23%
CHEMBL2093869	P05106	Integrin alpha-IIb/beta-3	85.01%	95.42%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.51%	100.00%
CHEMBL255	P29275	Adenosine A2b receptor	84.49%	98.59%
CHEMBL2492	P36544	Neuronal acetylcholine receptor protein alpha-7 subunit	84.41%	88.42%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	84.40%	97.23%
CHEMBL4644	P41968	Melanocortin receptor 3	84.38%	99.52%
CHEMBL340	P08684	Cytochrome P450 3A4	84.34%	91.19%
CHEMBL4101	P17612	cAMP-dependent protein kinase alpha-catalytic subunit	83.37%	82.86%
CHEMBL1937	Q92769	Histone deacetylase 2	83.02%	94.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.77%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.87%	94.45%
CHEMBL2535	P11166	Glucose transporter	81.47%	98.75%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 446809
• LOTUS: LTS0213151
• wikiData: Q76116303