(R)-S-lactoylglutathione

Details

• Internal ID: 7b07d8f9-4b60-4f85-b894-b8bfa781a082
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides > Oligopeptides
• IUPAC Name: (2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-3-[(2R)-2-hydroxypropanoyl]sulfanyl-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
• SMILES (Canonical): CC(C(=O)SCC(C(=O)NCC(=O)O)NC(=O)CCC(C(=O)O)N)O
• SMILES (Isomeric): C[C@H](C(=O)SC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N)O
• InChI: InChI=1S/C13H21N3O8S/c1-6(17)13(24)25-5-8(11(21)15-4-10(19)20)16-9(18)3-2-7(14)12(22)23/h6-8,17H,2-5,14H2,1H3,(H,15,21)(H,16,18)(H,19,20)(H,22,23)/t6-,7+,8+/m1/s1
• InChI Key: VDYDCVUWILIYQF-CSMHCCOUSA-N
• Popularity: 289 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₂₁N₃O₈S
• Molecular Weight: 379.39 g/mol
• Exact Mass: 379.10493581 g/mol
• Topological Polar Surface Area (TPSA): 221.00 Ų
• XlogP: -4.60
• Atomic LogP (AlogP): -2.50
• H-Bond Acceptor: 8
• H-Bond Donor: 6
• Rotatable Bonds: 11

Synonyms

• (R)-S-lactoylglutathione
• S-Lactoylglutathione
• D-lactoylglutathione
• S-[(2R)-2-hydroxypropanoyl]-gamma-L-glutamyl-L-cysteinylglycine
• S-lactoyl-glutathione
• 25138-66-3
• S-lactateglutathione
• S-lactate glutathione
• delta-lactoylglutathione
• S-D-lactoyl-glutathione
• S-delta-lactoylglutathione
• S-delta-lactoyl-glutathione
• SCHEMBL850658
• CHEBI:15694
• C03451
• Q63395383
• n-(n-l-gamma-glutamyl-S-(2-hydroxy-1-oxopropyl)-l-cysteinyl)-glycine
• (2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-{[(2R)-2-hydroxypropanoyl]sulfanyl}ethyl]carbamoyl}butanoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7696	76.96%
Caco-2	-	0.9344	93.44%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6343	63.43%
OATP2B1 inhibitior	-	0.8585	85.85%
OATP1B1 inhibitior	+	0.9233	92.33%
OATP1B3 inhibitior	+	0.9461	94.61%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7899	78.99%
P-glycoprotein inhibitior	-	0.9070	90.70%
P-glycoprotein substrate	-	0.6952	69.52%
CYP3A4 substrate	-	0.5366	53.66%
CYP2C9 substrate	-	0.6173	61.73%
CYP2D6 substrate	-	0.8032	80.32%
CYP3A4 inhibition	-	0.9072	90.72%
CYP2C9 inhibition	-	0.8795	87.95%
CYP2C19 inhibition	-	0.8686	86.86%
CYP2D6 inhibition	-	0.9473	94.73%
CYP1A2 inhibition	-	0.9173	91.73%
CYP2C8 inhibition	-	0.9111	91.11%
CYP inhibitory promiscuity	-	0.9768	97.68%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.6548	65.48%
Eye corrosion	-	0.9838	98.38%
Eye irritation	-	0.9840	98.40%
Skin irritation	-	0.8127	81.27%
Skin corrosion	-	0.9334	93.34%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6418	64.18%
Micronuclear	+	0.5200	52.00%
Hepatotoxicity	+	0.6326	63.26%
skin sensitisation	-	0.9057	90.57%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	-	0.5333	53.33%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.9164	91.64%
Acute Oral Toxicity (c)	III	0.7137	71.37%
Estrogen receptor binding	-	0.6487	64.87%
Androgen receptor binding	-	0.7253	72.53%
Thyroid receptor binding	+	0.5576	55.76%
Glucocorticoid receptor binding	-	0.6111	61.11%
Aromatase binding	-	0.6792	67.92%
PPAR gamma	+	0.6834	68.34%
Honey bee toxicity	-	0.9385	93.85%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.8100	81.00%
Fish aquatic toxicity	-	0.9026	90.26%

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	99.95%	83.82%
CHEMBL2581	P07339	Cathepsin D	99.25%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	96.57%	90.17%
CHEMBL236	P41143	Delta opioid receptor	96.12%	99.35%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.03%	99.17%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	95.76%	92.29%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.28%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.88%	94.45%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	90.75%	100.00%
CHEMBL230	P35354	Cyclooxygenase-2	89.89%	89.63%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	88.91%	96.47%
CHEMBL1255126	O15151	Protein Mdm4	88.67%	90.20%
CHEMBL2413	P32246	C-C chemokine receptor type 1	88.43%	89.50%
CHEMBL2973	O75116	Rho-associated protein kinase 2	88.34%	96.73%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	88.16%	97.21%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.06%	91.11%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	85.92%	95.71%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.20%	93.56%
CHEMBL1914	P06276	Butyrylcholinesterase	84.66%	95.00%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	84.43%	97.23%
CHEMBL340	P08684	Cytochrome P450 3A4	84.27%	91.19%
CHEMBL3308	P55212	Caspase-6	84.04%	97.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.55%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.40%	96.00%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	81.77%	93.10%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	81.36%	96.00%
CHEMBL1795117	Q8TEK3	Histone-lysine N-methyltransferase, H3 lysine-79 specific	81.31%	93.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.72%	96.95%
CHEMBL2514	O95665	Neurotensin receptor 2	80.34%	100.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 440018
• LOTUS: LTS0012168
• wikiData: Q63395383