[(1R)-1-[[(2S)-3-phenyl-2-[(pyrazin-2-carbonyl)amino]-1-oxopropyl]amino]-2-(4-fluorophenyl)ethyl]boronic Acid

ID: ALA499083

Chembl Id: CHEMBL499083

PubChem CID: 44190246

Max Phase: Preclinical

Molecular Formula: C22H22BFN4O4

Molecular Weight: 436.25

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  O=C(N[C@@H](Cc1ccccc1)C(=O)N[C@@H](Cc1ccc(F)cc1)B(O)O)c1cnccn1

Standard InChI:  InChI=1S/C22H22BFN4O4/c24-17-8-6-16(7-9-17)13-20(23(31)32)28-21(29)18(12-15-4-2-1-3-5-15)27-22(30)19-14-25-10-11-26-19/h1-11,14,18,20,31-32H,12-13H2,(H,27,30)(H,28,29)/t18-,20-/m0/s1

Standard InChI Key:  NTJSAWYQEMEWSC-ICSRJNTNSA-N

Associated Targets(Human)

PSMB5 Tclin Proteasome Macropain subunit MB1 (2451 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 436.25Molecular Weight (Monoisotopic): 436.1718AlogP: #Rotatable Bonds:
Polar Surface Area: Molecular Species: HBA: HBD:
#RO5 Violations: HBA (Lipinski): HBD (Lipinski): #RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: CX LogP: CX LogD:
Aromatic Rings: Heavy Atoms: QED Weighted: Np Likeness Score:

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. 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