Pyroglutamyllysyltryptophan

Details

• Internal ID: d7ed6d7d-ea84-41be-9c70-7954edc38436
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides > Oligopeptides
• IUPAC Name: (2S)-2-[[(2S)-6-amino-2-[[(2S)-5-oxopyrrolidine-2-carbonyl]amino]hexanoyl]amino]-3-(1H-indol-3-yl)propanoic acid
• InChI: InChI=1S/C22H29N5O5/c23-10-4-3-7-16(26-21(30)17-8-9-19(28)25-17)20(29)27-18(22(31)32)11-13-12-24-15-6-2-1-5-14(13)15/h1-2,5-6,12,16-18,24H,3-4,7-11,23H2,(H,25,28)(H,26,30)(H,27,29)(H,31,32)/t16-,17-,18-/m0/s1
• InChI Key: DDCLBYSFIHXSIU-BZSNNMDCSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₉N₅O₅
• Molecular Weight: 443.50 g/mol
• Exact Mass: 443.21686904 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: -2.70
• Atomic LogP (AlogP): 0.17
• H-Bond Acceptor: 5
• H-Bond Donor: 6
• Rotatable Bonds: 11

Synonyms

• 1kuk
• pEKW
• Pyr-Lys-Trp
• CHEBI:194214
• L-pyroglutamyl-L-lysyl-L-tryptophan

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8820	88.20%
Caco-2	-	0.9386	93.86%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5255	52.55%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9113	91.13%
OATP1B3 inhibitior	+	0.9483	94.83%
MATE1 inhibitior	-	0.9009	90.09%
OCT2 inhibitior	-	0.9112	91.12%
BSEP inhibitior	-	0.4563	45.63%
P-glycoprotein inhibitior	-	0.5600	56.00%
P-glycoprotein substrate	+	0.6661	66.61%
CYP3A4 substrate	+	0.6678	66.78%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7746	77.46%
CYP3A4 inhibition	-	0.9859	98.59%
CYP2C9 inhibition	-	0.9321	93.21%
CYP2C19 inhibition	-	0.9291	92.91%
CYP2D6 inhibition	-	0.9519	95.19%
CYP1A2 inhibition	-	0.8638	86.38%
CYP2C8 inhibition	-	0.6710	67.10%
CYP inhibitory promiscuity	-	0.9867	98.67%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.7133	71.33%
Eye corrosion	-	0.9934	99.34%
Eye irritation	-	0.9889	98.89%
Skin irritation	-	0.8267	82.67%
Skin corrosion	-	0.9456	94.56%
Ames mutagenesis	-	0.8500	85.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6622	66.22%
Micronuclear	+	0.6600	66.00%
Hepatotoxicity	-	0.5467	54.67%
skin sensitisation	-	0.9056	90.56%
Respiratory toxicity	+	0.9000	90.00%
Reproductive toxicity	+	0.9040	90.40%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.8620	86.20%
Acute Oral Toxicity (c)	III	0.6594	65.94%
Estrogen receptor binding	+	0.6453	64.53%
Androgen receptor binding	-	0.5394	53.94%
Thyroid receptor binding	-	0.6250	62.50%
Glucocorticoid receptor binding	-	0.5935	59.35%
Aromatase binding	-	0.5972	59.72%
PPAR gamma	+	0.6736	67.36%
Honey bee toxicity	-	0.8601	86.01%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	-	0.7706	77.06%

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	99.39%	91.11%
CHEMBL3310	Q96DB2	Histone deacetylase 11	98.48%	88.56%
CHEMBL2581	P07339	Cathepsin D	98.27%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.22%	95.56%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	96.20%	98.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.83%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.68%	97.09%
CHEMBL5103	Q969S8	Histone deacetylase 10	93.56%	90.08%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	92.59%	97.64%
CHEMBL3192	Q9BY41	Histone deacetylase 8	92.54%	93.99%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.05%	99.17%
CHEMBL3837	P07711	Cathepsin L	91.80%	96.61%
CHEMBL1255126	O15151	Protein Mdm4	91.72%	90.20%
CHEMBL4040	P28482	MAP kinase ERK2	90.46%	83.82%
CHEMBL4101	P17612	cAMP-dependent protein kinase alpha-catalytic subunit	89.17%	82.86%
CHEMBL5028	O14672	ADAM10	87.98%	97.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	87.89%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	87.66%	94.75%
CHEMBL4979	P13866	Sodium/glucose cotransporter 1	87.55%	98.24%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	87.46%	97.23%
CHEMBL1829	O15379	Histone deacetylase 3	86.89%	95.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.45%	94.45%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	85.76%	91.71%
CHEMBL213	P08588	Beta-1 adrenergic receptor	84.28%	95.56%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.01%	82.69%
CHEMBL1808	P12821	Angiotensin-converting enzyme	83.55%	93.39%
CHEMBL2514	O95665	Neurotensin receptor 2	83.53%	100.00%
CHEMBL255	P29275	Adenosine A2b receptor	83.44%	98.59%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	83.38%	83.10%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.66%	93.56%
CHEMBL2492	P36544	Neuronal acetylcholine receptor protein alpha-7 subunit	81.76%	88.42%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.70%	99.23%
CHEMBL4816	Q9Y243	Serine/threonine-protein kinase AKT3	81.38%	96.28%
CHEMBL2973	O75116	Rho-associated protein kinase 2	81.03%	96.73%
CHEMBL5939	Q9NZ08	Endoplasmic reticulum aminopeptidase 1	80.85%	100.00%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	80.34%	91.81%
CHEMBL340	P08684	Cytochrome P450 3A4	80.21%	91.19%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 446810
• LOTUS: LTS0141155
• wikiData: Q76116309