2-Amino-4-[2-(4-bromo-benzylsulfanyl)-1-(carboxymethyl-carbamoyl)-ethylcarbamoyl]-butyric acid

ID: ALA218644

Chembl Id: CHEMBL218644

PubChem CID: 97537

Max Phase: Preclinical

Molecular Formula: C17H22BrN3O6S

Molecular Weight: 476.35

Molecule Type: Small molecule

Names and Identifiers

Synonyms: S-(P-Bromobenzyl)Glutathione | S-P-Bromobenzyl Glutatione | S-P-Bromobenzylglutathione | S-p-bromobenzyl glutatione|S-P-Bromobenzylglutathione|S-(p-Bromobenzyl)glutathione|CHEMBL218644|S-(4-Bromobenzyl)glutathione|NSC 131115|0HG|SCHEMBL3280215|BDBM50241121|N-(S-((4-Bromophenyl)methyl)-N-L-gamma-glutamyl-L-cysteinyl)glycine|(S)-5-((R)-3-(4-bromobenzylthio)-1-(carboxymethylamino)-1-oxopropan-2-ylamino)-2-amino-5-oxopentanoic acid

Canonical SMILES:  N[C@@H](CCC(=O)N[C@@H](CSCc1ccc(Br)cc1)C(=O)NCC(=O)O)C(=O)O

Standard InChI:  InChI=1S/C17H22BrN3O6S/c18-11-3-1-10(2-4-11)8-28-9-13(16(25)20-7-15(23)24)21-14(22)6-5-12(19)17(26)27/h1-4,12-13H,5-9,19H2,(H,20,25)(H,21,22)(H,23,24)(H,26,27)/t12-,13-/m0/s1

Standard InChI Key:  HMNYAPVDRLKBJH-STQMWFEESA-N

Alternative Forms

1. Parent:

   

   ALA218644

   S-(p-Bromobenzyl)glutathione

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 476.35

Molecular Weight (Monoisotopic): 475.0413

AlogP: 0.56

#Rotatable Bonds: 12

Polar Surface Area: 158.82

Molecular Species: ZWITTERION

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.81

CX Basic pKa: 9.31

CX LogP: -2.12

CX LogD: -5.34

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.29

Np Likeness Score: -0.05

References

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2. D'Silva C, Daunes S..  (2000)  Structure-activity study on the in vitro antiprotozoal activity of glutathione derivatives.,  43  (10): [PMID:10821719] [10.1021/jm990259w]

3. Ly HD, Clugston SL, Sampson PB, Honek JF..  (1998)  Syntheses and kinetic evaluation of hydroxamate-based peptide inhibitors of glyoxalase I.,  8  (7): [PMID:9871526] [10.1016/s0960-894x(98)00116-4]

4. Vince R, Brownell J, Akella LB..  (1999)  Synthesis and activity of gamma-(L-gamma-azaglutamyl)-S-(p-bromobenzyl)-L-cysteinylglycine: a metabolically stable inhibitor of glyoxalase I.,  9  (6): [PMID:10206549] [10.1016/s0960-894x(99)00097-9]

5. More SS, Vince R..  (2006)  A metabolically stable tight-binding transition-state inhibitor of glyoxalase-I.,  16  (23): [PMID:16997560] [10.1016/j.bmcl.2006.08.121]

6. Takasawa R, Takahashi S, Saeki K, Sunaga S, Yoshimori A, Tanuma S..  (2008)  Structure-activity relationship of human GLO I inhibitory natural flavonoids and their growth inhibitory effects.,  16  (7): [PMID:18258440] [10.1016/j.bmc.2008.01.031]

7. More SS, Vince R..  (2009)  Inhibition of glyoxalase I: the first low-nanomolar tight-binding inhibitors.,  52  (15): [PMID:19610604] [10.1021/jm900382u]

8. Takasawa R, Saeki K, Tao A, Yoshimori A, Uchiro H, Fujiwara M, Tanuma S..  (2010)  Delphinidin, a dietary anthocyanidin in berry fruits, inhibits human glyoxalase I.,  18  (19): [PMID:20801663] [10.1016/j.bmc.2010.08.012]

9. Takasawa R, Tao A, Saeki K, Shionozaki N, Tanaka R, Uchiro H, Takahashi S, Yoshimori A, Tanuma S..  (2011)  Discovery of a new type inhibitor of human glyoxalase I by myricetin-based 4-point pharmacophore.,  21  (14): [PMID:21669529] [10.1016/j.bmcl.2011.05.046]

10. Chiba T, Ohwada J, Sakamoto H, Kobayashi T, Fukami TA, Irie M, Miura T, Ohara K, Koyano H..  (2012)  Design and evaluation of azaindole-substituted N-hydroxypyridones as glyoxalase I inhibitors.,  22  (24): [PMID:23122816] [10.1016/j.bmcl.2012.10.045]

11. Lyon PA, Vince R..  (1977)  Synthesis and kinetic evaluation of S- and N-substituted cysteinylglycines as inhibitors of glyoxalase I.,  20  (1): [PMID:833829] [10.1021/jm00211a015]

12. Holewinski RJ, Creighton DJ..  (2014)  Inhibition by active site directed covalent modification of human glyoxalase I.,  22  (13): [PMID:24856185] [10.1016/j.bmc.2014.04.055]

13. Jin T, Zhao L, Wang HP, Huang ML, Yue Y, Lu C, Zheng ZB..  (2020)  Recent advances in the discovery and development of glyoxalase I inhibitors.,  28  (4): [PMID:31879183] [10.1016/j.bmc.2019.115243]

Source

Source(1):

• Scientific Literature