S-(4-Hydroxybenzyl)glutathione

Details

• Internal ID: f70ea0c3-3029-42e5-bd3a-603059e2a5c6
• 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-hydroxyphenyl)methylsulfanyl]-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
• SMILES (Canonical): C1=CC(=CC=C1CSCC(C(=O)NCC(=O)O)NC(=O)CCC(C(=O)O)N)O
• SMILES (Isomeric): C1=CC(=CC=C1CSC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N)O
• InChI: InChI=1S/C17H23N3O7S/c18-12(17(26)27)5-6-14(22)20-13(16(25)19-7-15(23)24)9-28-8-10-1-3-11(21)4-2-10/h1-4,12-13,21H,5-9,18H2,(H,19,25)(H,20,22)(H,23,24)(H,26,27)/t12-,13-/m0/s1
• InChI Key: GZQWDMACVJFPRW-STQMWFEESA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₃N₃O₇S
• Molecular Weight: 413.40 g/mol
• Exact Mass: 413.12567125 g/mol
• Topological Polar Surface Area (TPSA): 204.00 Ų
• XlogP: -3.00
• Atomic LogP (AlogP): -0.50
• H-Bond Acceptor: 7
• H-Bond Donor: 6
• Rotatable Bonds: 12

Synonyms

• 129636-38-0
• L-Gamma-Glutamyl-S-[(4-hydroxyphenyl)methyl]-L-cysteinylglycine
• (2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-3-[(4-hydroxyphenyl)methylsulfanyl]-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
• S-(4-hydroxybenzyl) glutathione
• HY-N8115
• AKOS040763792
• MS-27149
• CS-0140161
• E88623
• L-|A-Glutamyl-S-[(4-hydroxyphenyl)methyl]-L-cysteinylglycine

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7855	78.55%
Caco-2	-	0.9578	95.78%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6830	68.30%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9109	91.09%
OATP1B3 inhibitior	+	0.9509	95.09%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.4923	49.23%
P-glycoprotein inhibitior	-	0.7094	70.94%
P-glycoprotein substrate	-	0.6536	65.36%
CYP3A4 substrate	-	0.5156	51.56%
CYP2C9 substrate	-	0.6307	63.07%
CYP2D6 substrate	-	0.7852	78.52%
CYP3A4 inhibition	-	0.9357	93.57%
CYP2C9 inhibition	-	0.9382	93.82%
CYP2C19 inhibition	-	0.8702	87.02%
CYP2D6 inhibition	-	0.9223	92.23%
CYP1A2 inhibition	-	0.9037	90.37%
CYP2C8 inhibition	+	0.4586	45.86%
CYP inhibitory promiscuity	-	0.9870	98.70%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8100	81.00%
Carcinogenicity (trinary)	Non-required	0.7216	72.16%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9650	96.50%
Skin irritation	-	0.7806	78.06%
Skin corrosion	-	0.9397	93.97%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6842	68.42%
Micronuclear	+	0.6400	64.00%
Hepatotoxicity	+	0.7052	70.52%
skin sensitisation	-	0.8917	89.17%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.9632	96.32%
Acute Oral Toxicity (c)	III	0.6983	69.83%
Estrogen receptor binding	+	0.6927	69.27%
Androgen receptor binding	-	0.5380	53.80%
Thyroid receptor binding	+	0.5252	52.52%
Glucocorticoid receptor binding	-	0.5090	50.90%
Aromatase binding	-	0.5828	58.28%
PPAR gamma	+	0.6843	68.43%
Honey bee toxicity	-	0.8605	86.05%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	-	0.7691	76.91%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.58%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	99.12%	83.82%
CHEMBL3060	Q9Y345	Glycine transporter 2	97.78%	99.17%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	96.66%	92.29%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.33%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.20%	94.45%
CHEMBL236	P41143	Delta opioid receptor	94.09%	99.35%
CHEMBL1255126	O15151	Protein Mdm4	93.93%	90.20%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	93.80%	97.23%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	93.04%	85.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.15%	96.09%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	90.60%	100.00%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	88.50%	93.10%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	88.08%	97.21%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	87.59%	94.01%
CHEMBL2514	O95665	Neurotensin receptor 2	87.35%	100.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.59%	96.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.54%	95.56%
CHEMBL4101	P17612	cAMP-dependent protein kinase alpha-catalytic subunit	85.07%	82.86%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.68%	99.15%
CHEMBL340	P08684	Cytochrome P450 3A4	84.59%	91.19%
CHEMBL3891	P07384	Calpain 1	84.46%	93.04%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.97%	93.56%
CHEMBL5261	Q7L7X3	Serine/threonine-protein kinase TAO1	83.70%	89.33%
CHEMBL221	P23219	Cyclooxygenase-1	83.13%	90.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.89%	95.50%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.61%	90.71%

Plants that contains it

• Gastrodia elata

Cross-Links

• PubChem: 10364396
• NPASS: NPC108908
• LOTUS: LTS0209643
• wikiData: Q105024540