4-((S)-3-((R)-2-(6-benzylpyrazin-2-yl)pyrrolidin-1-yl)-2-((S)-2-(methylamino)propanamido)-3-oxopropyl)benzylphosphonic acid

ID: ALA4291873

PubChem CID: 142585375

Max Phase: Preclinical

Molecular Formula: C29H36N5O5P

Molecular Weight: 565.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN[C@@H](C)C(=O)N[C@@H](Cc1ccc(CP(=O)(O)O)cc1)C(=O)N1CCC[C@@H]1c1cncc(Cc2ccccc2)n1

Standard InChI:  InChI=1S/C29H36N5O5P/c1-20(30-2)28(35)33-25(16-22-10-12-23(13-11-22)19-40(37,38)39)29(36)34-14-6-9-27(34)26-18-31-17-24(32-26)15-21-7-4-3-5-8-21/h3-5,7-8,10-13,17-18,20,25,27,30H,6,9,14-16,19H2,1-2H3,(H,33,35)(H2,37,38,39)/t20-,25-,27+/m0/s1

Standard InChI Key:  WUBYWMCSLYLAKN-QOAWAWRESA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA4291873

   ---

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: 565.61

Molecular Weight (Monoisotopic): 565.2454

AlogP: 2.74

#Rotatable Bonds: 11

Polar Surface Area: 144.75

Molecular Species: ZWITTERION

HBA: 6

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.73

CX Basic pKa: 8.69

CX LogP: -0.09

CX LogD: -0.17

Aromatic Rings: 3

Heavy Atoms: 40

QED Weighted: 0.26

Np Likeness Score: -0.23

References

1. Baggio C, Gambini L, Udompholkul P, Salem AF, Aronson A, Dona A, Troadec E, Pichiorri F, Pellecchia M..  (2018)  Design of Potent pan-IAP and Lys-Covalent XIAP Selective Inhibitors Using a Thermodynamics Driven Approach.,  61  (14): [PMID:29940121] [10.1021/acs.jmedchem.8b00810]

Source

Source(1):

• Scientific Literature