(S)-N-(4-(((2S,5R)-5-((R)-Hydroxy(pyridin-3-yl)methyl)-pyrrolidin-2-yl)methyl)phenyl)-5,6-dihydro-4H-pyrrolo[1,2-b]-pyrazole-6-carboxamide

ID: ALA3128188

PubChem CID: 70792359

Max Phase: Preclinical

Molecular Formula: C24H27N5O2

Molecular Weight: 417.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(C[C@@H]2CC[C@H]([C@H](O)c3cccnc3)N2)cc1)[C@@H]1CCc2ccnn21

Standard InChI:  InChI=1S/C24H27N5O2/c30-23(17-2-1-12-25-15-17)21-9-7-19(27-21)14-16-3-5-18(6-4-16)28-24(31)22-10-8-20-11-13-26-29(20)22/h1-6,11-13,15,19,21-23,27,30H,7-10,14H2,(H,28,31)/t19-,21+,22-,23+/m0/s1

Standard InChI Key:  VXXIYUBYYXZZOE-FCJDFRRUSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
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   12.9590   -7.9944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1784   -7.7296    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1550   -9.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.6621   -9.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6199   -7.8735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7800   -5.8788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8061   -6.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6788   -7.1869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2197   -7.3640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.6625   -6.8343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3614   -7.2705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7818   -7.3160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5350   -7.0913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4297   -8.4037    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7027   -8.0155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0342   -8.5315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2118   -6.6061    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1378   -7.9695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4595   -8.5785    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1914   -8.1887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8759   -7.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3841   -6.7535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  1  2  1  0
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  8  4  1  0
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  6 30  1  1
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 31 20  1  6
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 15 13  1  1
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 16 32  2  0
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 15 23  1  0
 20 21  1  0
  9 21  1  0
 23 10  1  1
 26 11  2  0
 22  9  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3128188

   (6S)-N-[4-[[(2S,5R)-5-[(R)-hydroxy(pyridin-3-yl)methyl]pyrrolidin-2-yl]methyl]phenyl]-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-6-carboxamide

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: 417.51

Molecular Weight (Monoisotopic): 417.2165

AlogP: 2.80

#Rotatable Bonds: 6

Polar Surface Area: 92.07

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.16

CX Basic pKa: 10.44

CX LogP: 2.02

CX LogD: -0.81

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.57

Np Likeness Score: -0.55

References

1. Moyes CR, Berger R, Goble SD, Harper B, Shen DM, Wang L, Bansal A, Brown PN, Chen AS, Dingley KH, Di Salvo J, Fitzmaurice A, Gichuru LN, Hurley AL, Jochnowitz N, Miller RR, Mistry S, Nagabukuro H, Salituro GM, Sanfiz A, Stevenson AS, Villa K, Zamlynny B, Struthers M, Weber AE, Edmondson SD..  (2014)  Design, synthesis, and evaluation of conformationally restricted acetanilides as potent and selective β3 adrenergic receptor agonists for the treatment of overactive bladder.,  57  (4): [PMID:24437735] [10.1021/jm4017224]

2. 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