gamma-Glutamylalanine

Details

• Internal ID: 398322ad-d917-4583-baf9-0097bc35cff5
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides > Dipeptides
• IUPAC Name: (2S)-2-amino-5-[[(1S)-1-carboxyethyl]amino]-5-oxopentanoic acid
• SMILES (Canonical): CC(C(=O)O)NC(=O)CCC(C(=O)O)N
• SMILES (Isomeric): C[C@@H](C(=O)O)NC(=O)CC[C@@H](C(=O)O)N
• InChI: InChI=1S/C8H14N2O5/c1-4(7(12)13)10-6(11)3-2-5(9)8(14)15/h4-5H,2-3,9H2,1H3,(H,10,11)(H,12,13)(H,14,15)/t4-,5-/m0/s1
• InChI Key: WQXXXVRAFAKQJM-WHFBIAKZSA-N
• Popularity: 19 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₁₄N₂O₅
• Molecular Weight: 218.21 g/mol
• Exact Mass: 218.09027155 g/mol
• Topological Polar Surface Area (TPSA): 130.00 Ų
• XlogP: -3.80
• Atomic LogP (AlogP): -1.23
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 6

Synonyms

• gamma-Glutamylalanine
• gamma-Gln-ala
• (2S)-2-Amino-5-[[(1S)-1-carboxyethyl]amino]-5-oxopentanoic acid
• CHEBI:50621
• (2S)-2-amino-5-(((1S)-1-carboxyethyl)amino)-5-oxopentanoic acid
• RefChem:922048
• H-GAMMA-GLU-ALA-OH
• gamma-Glu-Ala
• gamma-L-Glutamyl-L-alanine
• H-Glu(Ala-OH)-OH
• 5-L-Glutamyl-L-alanine
• g-Glu-Ala
• MFCD00037215
• L-gamma-glutamyl-L-alanine
• (2S)-2-amino-4-{[(1S)-1-carboxyethyl]carbamoyl}butanoic acid
• (S)-2-Amino-5-(((S)-1-carboxyethyl)amino)-5-oxopentanoic acid
• H-?-Glu-Ala-OH
• g-Glu-Ala-OH
• (S)-2-Amino-5-[[(S)-1-carboxyethyl]amino]-5-oxopentanoic Acid
• g-Glutamylalanine
• 5-L-glutamylalanine
• L-gamma-Glu-L-Ala
• gamma-Glutamyl-alanine
• H--Glu-Ala-OH
• g-L-Glutamyl-L-alanine
• H-| pound-Glu-Ala-Oh
• H-GLU(ALA)-OH
• N-L-gamma-glutamyl-L-alanine
• orb1299758
• SCHEMBL3707747
• CHEBI:50619
• DTXSID80974270
• L-Alanine, N-L-gamma-glutamyl-
• gamma-L-Glutamyl-L-alanine, 98%
• EBC-616177
• AS-83087
• BP-41264
• DA-74123
• SY401821
• HY-112171
• CS-0043596
• 5-[(1-Carboxyethyl)imino]-5-hydroxynorvaline
• E85624
• F492881
• Q27122149
• (2S)-2-amino-5-[[(1S)-1-carboxyethyl]amino]-5-oxo-pentanoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6079	60.79%
Caco-2	-	0.9090	90.90%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6926	69.26%
OATP2B1 inhibitior	-	0.8518	85.18%
OATP1B1 inhibitior	+	0.9605	96.05%
OATP1B3 inhibitior	+	0.9561	95.61%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9822	98.22%
BSEP inhibitior	-	0.9810	98.10%
P-glycoprotein inhibitior	-	0.9856	98.56%
P-glycoprotein substrate	-	0.8781	87.81%
CYP3A4 substrate	-	0.6819	68.19%
CYP2C9 substrate	-	0.6346	63.46%
CYP2D6 substrate	-	0.8048	80.48%
CYP3A4 inhibition	-	0.9177	91.77%
CYP2C9 inhibition	-	0.9651	96.51%
CYP2C19 inhibition	-	0.9716	97.16%
CYP2D6 inhibition	-	0.9651	96.51%
CYP1A2 inhibition	-	0.9212	92.12%
CYP2C8 inhibition	-	0.9948	99.48%
CYP inhibitory promiscuity	-	0.9931	99.31%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.6641	66.41%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.9750	97.50%
Skin irritation	-	0.8851	88.51%
Skin corrosion	-	0.7591	75.91%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7954	79.54%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.9633	96.33%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	-	0.6010	60.10%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.7736	77.36%
Acute Oral Toxicity (c)	IV	0.6404	64.04%
Estrogen receptor binding	-	0.7994	79.94%
Androgen receptor binding	-	0.9058	90.58%
Thyroid receptor binding	-	0.8740	87.40%
Glucocorticoid receptor binding	-	0.7047	70.47%
Aromatase binding	-	0.8133	81.33%
PPAR gamma	-	0.8428	84.28%
Honey bee toxicity	-	0.9692	96.92%
Biodegradation	+	0.5250	52.50%
Crustacea aquatic toxicity	-	0.9100	91.00%
Fish aquatic toxicity	-	0.8978	89.78%

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	99.41%	83.82%
CHEMBL230	P35354	Cyclooxygenase-2	96.92%	89.63%
CHEMBL221	P23219	Cyclooxygenase-1	94.83%	90.17%
CHEMBL2581	P07339	Cathepsin D	94.69%	98.95%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	94.64%	92.29%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.49%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.32%	99.17%
CHEMBL236	P41143	Delta opioid receptor	91.16%	99.35%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	90.95%	100.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	87.49%	96.47%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.56%	93.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.84%	90.71%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.52%	89.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.37%	94.33%
CHEMBL1255126	O15151	Protein Mdm4	81.37%	90.20%
CHEMBL2514	O95665	Neurotensin receptor 2	80.35%	100.00%

Plants that contains it

• Dietes bicolor

Cross-Links

• PubChem: 440103
• LOTUS: LTS0047058
• wikiData: Q27122149