[(1R)-1-[[(2S)-3-phenyl-2-[((S)-(-)-1,2,3,4-tetrahedro-naphthoic-1-carbonyl)amino]-1-oxopropyl]amino]-3-methylbutyl]boronic Acid

ID: ALA499361

Chembl Id: CHEMBL499361

PubChem CID: 44191199

Max Phase: Preclinical

Molecular Formula: C25H33BN2O4

Molecular Weight: 436.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H]1CCCc2ccccc21)B(O)O

Standard InChI:  InChI=1S/C25H33BN2O4/c1-17(2)15-23(26(31)32)28-25(30)22(16-18-9-4-3-5-10-18)27-24(29)21-14-8-12-19-11-6-7-13-20(19)21/h3-7,9-11,13,17,21-23,31-32H,8,12,14-16H2,1-2H3,(H,27,29)(H,28,30)/t21-,22-,23-/m0/s1

Standard InChI Key:  HLDAUCRRBXUURL-VABKMULXSA-N

Alternative Forms

1. Parent:

   

   ALA499361

   [(1R)-3-methyl-1-[[(2S)-3-phenyl-2-[[(1S)-1,2,3,4-tetrahydronaphthalene-1-carbonyl]amino]propanoyl]amino]butyl]boronic acid

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: 436.36

Molecular Weight (Monoisotopic): 436.2533

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References

1. Zhu Y, Zhao X, Zhu X, Wu G, Li Y, Ma Y, Yuan Y, Yang J, Hu Y, Ai L, Gao Q..  (2009)  Design, synthesis, biological evaluation, and structure-activity relationship (SAR) discussion of dipeptidyl boronate proteasome inhibitors, part I: comprehensive understanding of the SAR of alpha-amino acid boronates.,  52  (14): [PMID:19537716] [10.1021/jm9005093]

2. Shi J, Lei M, Wu W, Feng H, Wang J, Chen S, Zhu Y, Hu S, Liu Z, Jiang C..  (2016)  Design, synthesis and docking studies of novel dipeptidyl boronic acid proteasome inhibitors constructed from αα- and αβ-amino acids.,  26  (8): [PMID:26965867] [10.1016/j.bmcl.2016.03.007]

3. Lei M, Feng H, Wang C, Li H, Shi J, Wang J, Liu Z, Chen S, Hu S, Zhu Y..  (2016)  3D-QSAR-aided design, synthesis, in vitro and in vivo evaluation of dipeptidyl boronic acid proteasome inhibitors and mechanism studies.,  24  (11): [PMID:27117691] [10.1016/j.bmc.2016.04.025]

Source

Source(1):

• Scientific Literature