(R)-N-(4-(((2S,5R)-5-((R)-Hydroxy(pyridin-3-yl)methyl)-pyrrolidin-2-yl)methyl)phenyl)-5,6-dihydro-4H-cyclopenta[d]-thiazole-4-carboxamide

ID: ALA3128178

PubChem CID: 76322043

Max Phase: Preclinical

Molecular Formula: C24H26N4O2S

Molecular Weight: 434.57

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]1CCc2scnc21

Standard InChI:  InChI=1S/C24H26N4O2S/c29-23(16-2-1-11-25-13-16)20-9-7-18(27-20)12-15-3-5-17(6-4-15)28-24(30)19-8-10-21-22(19)26-14-31-21/h1-6,11,13-14,18-20,23,27,29H,7-10,12H2,(H,28,30)/t18-,19+,20+,23+/m0/s1

Standard InChI Key:  OYURTPRHVJSKRC-DZCCDHAISA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
   16.4647  -11.8628    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.4793  -11.0317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6989  -10.7657    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6755  -12.0947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2009  -11.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4124  -11.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3996  -12.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1802  -12.7545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6092   -9.9172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0560   -9.3032    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2765  -11.1813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1421  -10.9103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3015   -8.9143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8547  -11.1329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3278   -9.7389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6342  -10.1779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2027  -10.2245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7390  -10.4025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3168  -10.9073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1855   -9.8702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8837  -10.3085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3026  -10.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0560  -10.1285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9531  -11.4390    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2267  -11.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5555  -11.5673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7320   -9.6409    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6605  -11.0067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9795  -11.6145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7107  -11.2271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3994  -10.1306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9072   -9.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  1  2  1  0
  3  5  1  0
  4  1  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  4  1  0
 28 16  1  0
  6 30  1  1
 24 28  2  0
 14 26  1  0
 17 25  2  0
 31 20  1  6
 31 27  1  0
 30 18  2  0
 15 13  1  1
 31 12  1  0
 25 24  1  0
 23 19  1  0
 29 30  1  0
 16 15  1  0
 27 23  1  0
 16 32  2  0
 11 29  1  0
 21 14  2  0
 32 17  1  0
 19 12  1  0
 11 22  1  0
 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:

   

   ALA3128178

   (4R)-N-[4-[[(2S,5R)-5-[(R)-hydroxy(pyridin-3-yl)methyl]pyrrolidin-2-yl]methyl]phenyl]-5,6-dihydro-4H-cyclopenta[d][1,3]thiazole-4-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: 434.57

Molecular Weight (Monoisotopic): 434.1776

AlogP: 3.60

#Rotatable Bonds: 6

Polar Surface Area: 87.14

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.48

CX Basic pKa: 10.44

CX LogP: 3.06

CX LogD: 0.23

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.55

Np Likeness Score: -0.54

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