(S)-N-(4-(((2S,5R)-5-((R)-Hydroxy(phenyl)methyl)pyrrolidin-2-yl)-methyl)phenyl)-2-(6-oxopyridazin-1(6H)-yl)propanamide

ID: ALA3765335

PubChem CID: 127037832

Max Phase: Preclinical

Molecular Formula: C25H28N4O3

Molecular Weight: 432.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](C(=O)Nc1ccc(C[C@@H]2CC[C@H]([C@H](O)c3ccccc3)N2)cc1)n1ncccc1=O

Standard InChI:  InChI=1S/C25H28N4O3/c1-17(29-23(30)8-5-15-26-29)25(32)28-20-11-9-18(10-12-20)16-21-13-14-22(27-21)24(31)19-6-3-2-4-7-19/h2-12,15,17,21-22,24,27,31H,13-14,16H2,1H3,(H,28,32)/t17-,21-,22+,24+/m0/s1

Standard InChI Key:  PBXGYXYBIGMVQD-KBABAZTHSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6375   -0.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2809   -2.3599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2755   -3.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0234   -4.7733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4911   -4.4637    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4090   -6.1397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0841   -6.2921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4523   -5.2233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9597   -5.0741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5630   -6.7368    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4373   -5.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9417   -4.4240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4603   -3.5054    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9309   -5.6632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8052   -4.4433    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1835   -3.0781    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0548   -1.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2983   -4.5873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7957   -5.6793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1696   -3.3663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5479   -2.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4265   -6.7561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  6
  8 10  1  0
 10 11  1  0
 12 11  1  0
 12 13  1  0
 13  8  1  0
 12 14  1  1
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 18 21  1  0
 21 22  1  0
 22 23  2  0
  8 24  1  6
 22 25  1  0
 25 26  1  0
 26 27  1  0
 26 29  1  0
 27 28  2  0
 28 32  1  0
 31 29  1  0
 29 30  2  0
 31 32  2  0
 25 33  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA3765335

   ---

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: 432.52

Molecular Weight (Monoisotopic): 432.2161

AlogP: 2.84

#Rotatable Bonds: 7

Polar Surface Area: 96.25

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.55

CX Basic pKa: 10.61

CX LogP: 2.62

CX LogD: -0.31

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.53

Np Likeness Score: -0.57

References

1. Edmondson SD, Zhu C, Kar NF, Di Salvo J, Nagabukuro H, Sacre-Salem B, Dingley K, Berger R, Goble SD, Morriello G, Harper B, Moyes CR, Shen DM, Wang L, Ball R, Fitzmaurice A, Frenkl T, Gichuru LN, Ha S, Hurley AL, Jochnowitz N, Levorse D, Mistry S, Miller RR, Ormes J, Salituro GM, Sanfiz A, Stevenson AS, Villa K, Zamlynny B, Green S, Struthers M, Weber AE..  (2016)  Discovery of Vibegron: A Potent and Selective β3 Adrenergic Receptor Agonist for the Treatment of Overactive Bladder.,  59  (2): [PMID:26709102] [10.1021/acs.jmedchem.5b01372]

Source

Source(1):

• Scientific Literature