L-gamma-Glutamyl-L-cysteinylglycinamide

Details

• Internal ID: 1abebe75-f424-4d01-980f-77ec5dbf24a3
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides > Oligopeptides
• IUPAC Name: (2S)-2-amino-5-[[(2R)-1-[(2-amino-2-oxoethyl)amino]-1-oxo-3-sulfanylpropan-2-yl]amino]-5-oxopentanoic acid
• InChI: InChI=1S/C10H18N4O5S/c11-5(10(18)19)1-2-8(16)14-6(4-20)9(17)13-3-7(12)15/h5-6,20H,1-4,11H2,(H2,12,15)(H,13,17)(H,14,16)(H,18,19)/t5-,6-/m0/s1
• InChI Key: FBCIXVYKFFJYFT-WDSKDSINSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₈N₄O₅S
• Molecular Weight: 306.34 g/mol
• Exact Mass: 306.09979086 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: -5.10
• Atomic LogP (AlogP): -2.81
• H-Bond Acceptor: 6
• H-Bond Donor: 6
• Rotatable Bonds: 9

Synonyms

• 82147-51-1
• L-gamma-Glutamyl-L-cysteinylglycinamide
• GASH
• L-gamma-glutamyl-L-cysteinylglycine amide
• GASH cpd
• SCHEMBL2266897
• CHEBI:59399
• AKOS040751924
• (2S)-2-amino-5-[[(2R)-1-[(2-amino-2-oxoethyl)amino]-1-oxo-3-sulfanylpropan-2-yl]amino]-5-oxopentanoic acid
• gamma-L-Glutamyl-L-cysteinylglycine amide
• Glycinamide, L-gamma-glutamyl-L-cysteinyl-
• C19689
• Q27126679
• N5-((R)-1-((2-amino-2-oxoethyl)amino)-3-mercapto-1-oxopropan-2-yl)-L-glutamine

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8377	83.77%
Caco-2	-	0.9409	94.09%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5536	55.36%
OATP2B1 inhibitior	-	0.8554	85.54%
OATP1B1 inhibitior	+	0.9463	94.63%
OATP1B3 inhibitior	+	0.9486	94.86%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9159	91.59%
P-glycoprotein inhibitior	-	0.9235	92.35%
P-glycoprotein substrate	-	0.7945	79.45%
CYP3A4 substrate	-	0.5792	57.92%
CYP2C9 substrate	-	0.8064	80.64%
CYP2D6 substrate	-	0.7953	79.53%
CYP3A4 inhibition	-	0.9390	93.90%
CYP2C9 inhibition	-	0.9179	91.79%
CYP2C19 inhibition	-	0.9190	91.90%
CYP2D6 inhibition	-	0.9502	95.02%
CYP1A2 inhibition	-	0.9437	94.37%
CYP2C8 inhibition	-	0.9435	94.35%
CYP inhibitory promiscuity	-	0.9898	98.98%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.7183	71.83%
Eye corrosion	-	0.9852	98.52%
Eye irritation	-	0.9907	99.07%
Skin irritation	-	0.8365	83.65%
Skin corrosion	-	0.9419	94.19%
Ames mutagenesis	+	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7001	70.01%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	+	0.7899	78.99%
skin sensitisation	-	0.9338	93.38%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	-	0.5889	58.89%
Mitochondrial toxicity	-	0.6875	68.75%
Nephrotoxicity	-	0.9020	90.20%
Acute Oral Toxicity (c)	III	0.6713	67.13%
Estrogen receptor binding	+	0.5816	58.16%
Androgen receptor binding	-	0.8590	85.90%
Thyroid receptor binding	-	0.5612	56.12%
Glucocorticoid receptor binding	+	0.5526	55.26%
Aromatase binding	-	0.6773	67.73%
PPAR gamma	+	0.6571	65.71%
Honey bee toxicity	-	0.9129	91.29%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7900	79.00%
Fish aquatic toxicity	-	0.9148	91.48%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.15%	83.82%
CHEMBL2581	P07339	Cathepsin D	97.14%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	96.73%	90.17%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.49%	99.17%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	94.47%	92.29%
CHEMBL236	P41143	Delta opioid receptor	93.16%	99.35%
CHEMBL230	P35354	Cyclooxygenase-2	91.61%	89.63%
CHEMBL1255126	O15151	Protein Mdm4	91.35%	90.20%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	91.23%	97.21%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.23%	94.45%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	89.81%	100.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	89.60%	96.95%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	89.31%	95.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.75%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.64%	96.09%
CHEMBL233	P35372	Mu opioid receptor	87.14%	97.93%
CHEMBL4394	Q9NYA1	Sphingosine kinase 1	86.08%	96.03%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	85.83%	97.23%
CHEMBL340	P08684	Cytochrome P450 3A4	85.59%	91.19%
CHEMBL5261	Q7L7X3	Serine/threonine-protein kinase TAO1	85.08%	89.33%
CHEMBL3784	Q09472	Histone acetyltransferase p300	84.33%	93.33%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	84.06%	96.47%
CHEMBL4101	P17612	cAMP-dependent protein kinase alpha-catalytic subunit	84.00%	82.86%
CHEMBL1795117	Q8TEK3	Histone-lysine N-methyltransferase, H3 lysine-79 specific	83.14%	93.56%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.75%	89.50%
CHEMBL5701	Q9H2K8	Serine/threonine-protein kinase TAO3	82.56%	96.67%
CHEMBL4816	Q9Y243	Serine/threonine-protein kinase AKT3	82.33%	96.28%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.65%	93.00%
CHEMBL2514	O95665	Neurotensin receptor 2	81.47%	100.00%
CHEMBL4979	P13866	Sodium/glucose cotransporter 1	81.23%	98.24%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 448816
• LOTUS: LTS0229889
• wikiData: Q27126679