rac-5-(5-cyano-2-(pyrrolidin-3-yloxy)phenyl)-2-ureidothiophene-3-carboxamide

ID: ALA2425626

PubChem CID: 73355316

Max Phase: Preclinical

Molecular Formula: C17H17N5O3S

Molecular Weight: 371.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1ccc(OC2CCNC2)c(-c2cc(C(N)=O)c(NC(N)=O)s2)c1

Standard InChI:  InChI=1S/C17H17N5O3S/c18-7-9-1-2-13(25-10-3-4-21-8-10)11(5-9)14-6-12(15(19)23)16(26-14)22-17(20)24/h1-2,5-6,10,21H,3-4,8H2,(H2,19,23)(H3,20,22,24)

Standard InChI Key:  LSURYHMYIRZBGK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   12.6898  -10.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6887  -11.6352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4034  -12.0481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1199  -11.6348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1170  -10.8043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4016  -10.3951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8294  -10.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5844  -10.7193    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.1340  -10.1041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7188   -9.3912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9126   -9.5658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0530   -8.6340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8731   -8.5446    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5655   -7.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9549  -10.1873    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2933  -10.9397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1140  -11.0227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8108  -11.6089    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3933   -9.5692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6747   -9.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4062  -12.8691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4060  -13.6940    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5782   -8.3449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7696   -8.1816    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3643   -8.9002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9225   -9.5076    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
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11  7  2  0
  5  7  1  0
 12 13  1  0
 12 14  2  0
 10 12  1  0
  9 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
  6 19  1  0
 19 20  1  0
 21 22  3  0
  3 21  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2425626

   2-(Carbamoylamino)-5-(5-cyano-2-pyrrolidin-3-yloxyphenyl)thiophene-3-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: 371.42

Molecular Weight (Monoisotopic): 371.1052

AlogP: 1.62

#Rotatable Bonds: 5

Polar Surface Area: 143.26

Molecular Species: BASE

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.73

CX Basic pKa: 10.08

CX LogP: 0.70

CX LogD: -1.46

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.63

Np Likeness Score: -0.97

References

1. Hendrickx R, Johansson JG, Lohmann C, Jenvert RM, Blomgren A, Börjesson L, Gustavsson L..  (2013)  Identification of novel substrates and structure-activity relationship of cellular uptake mediated by human organic cation transporters 1 and 2.,  56  (18): [PMID:23984907] [10.1021/jm400966v]

Source

Source(1):

• Scientific Literature