gammaGluCys(4MeOI3M)Gly

Details

• Internal ID: b372091b-6800-4b41-98fb-dbb14e2bdaaa
• 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-[(4-methoxy-1H-indol-3-yl)methylsulfanyl]-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
• SMILES (Canonical): COC1=CC=CC2=C1C(=CN2)CSCC(C(=O)NCC(=O)O)NC(=O)CCC(C(=O)O)N
• SMILES (Isomeric): COC1=CC=CC2=C1C(=CN2)CSC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N
• InChI: InChI=1S/C20H26N4O7S/c1-31-15-4-2-3-13-18(15)11(7-22-13)9-32-10-14(19(28)23-8-17(26)27)24-16(25)6-5-12(21)20(29)30/h2-4,7,12,14,22H,5-6,8-10,21H2,1H3,(H,23,28)(H,24,25)(H,26,27)(H,29,30)/t12-,14-/m0/s1
• InChI Key: VQCJUVLBCCMWJY-JSGCOSHPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆N₄O₇S
• Molecular Weight: 466.50 g/mol
• Exact Mass: 466.15222035 g/mol
• Topological Polar Surface Area (TPSA): 209.00 Ų
• XlogP: -2.50
• Atomic LogP (AlogP): 0.29
• H-Bond Acceptor: 7
• H-Bond Donor: 6
• Rotatable Bonds: 13

Synonyms

• L-gammaGlu-L-Cys-(4MeOI3M)-Gly
• S-(4-methoxyindol-3-ylmethyl)-glutathione
• L-gamma-glutamyl-S-[(4-methoxy-1H-indol-3-yl)methyl]-L-cysteinylglycine
• CHEBI:65007
• Q27133567

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9310	93.10%
Caco-2	-	0.9332	93.32%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6021	60.21%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9030	90.30%
OATP1B3 inhibitior	+	0.9450	94.50%
MATE1 inhibitior	-	0.9009	90.09%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.5222	52.22%
P-glycoprotein inhibitior	-	0.5121	51.21%
P-glycoprotein substrate	+	0.5728	57.28%
CYP3A4 substrate	+	0.6235	62.35%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7633	76.33%
CYP3A4 inhibition	-	0.9692	96.92%
CYP2C9 inhibition	-	0.7826	78.26%
CYP2C19 inhibition	-	0.8285	82.85%
CYP2D6 inhibition	-	0.9086	90.86%
CYP1A2 inhibition	-	0.8166	81.66%
CYP2C8 inhibition	+	0.5527	55.27%
CYP inhibitory promiscuity	-	0.8797	87.97%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.6663	66.63%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.9743	97.43%
Skin irritation	-	0.7854	78.54%
Skin corrosion	-	0.9377	93.77%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6066	60.66%
Micronuclear	+	0.7400	74.00%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.8956	89.56%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.9440	94.40%
Acute Oral Toxicity (c)	III	0.6165	61.65%
Estrogen receptor binding	+	0.6839	68.39%
Androgen receptor binding	-	0.6211	62.11%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.4785	47.85%
Aromatase binding	-	0.4861	48.61%
PPAR gamma	+	0.6578	65.78%
Honey bee toxicity	-	0.8327	83.27%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	-	0.8558	85.58%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.69%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.72%	96.09%
CHEMBL1255126	O15151	Protein Mdm4	98.37%	90.20%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.21%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.73%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.39%	99.17%
CHEMBL4040	P28482	MAP kinase ERK2	96.28%	83.82%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.90%	95.56%
CHEMBL2535	P11166	Glucose transporter	92.55%	98.75%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.07%	96.00%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	91.76%	97.23%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	91.57%	92.29%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.44%	89.62%
CHEMBL1287628	Q9Y5S8	NADPH oxidase 1	87.93%	95.48%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	87.42%	97.21%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.86%	96.95%
CHEMBL340	P08684	Cytochrome P450 3A4	85.68%	91.19%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	84.66%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.45%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.73%	97.14%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.55%	95.50%
CHEMBL4101	P17612	cAMP-dependent protein kinase alpha-catalytic subunit	83.51%	82.86%
CHEMBL1914	P06276	Butyrylcholinesterase	83.00%	95.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.92%	89.50%
CHEMBL213	P08588	Beta-1 adrenergic receptor	82.80%	95.56%
CHEMBL5028	O14672	ADAM10	80.66%	97.50%

Plants that contains it

• Arabidopsis thaliana

Cross-Links

• PubChem: 70678641
• LOTUS: LTS0251684
• wikiData: Q27133567