rac-3-(2-(4-carbamoyl-5-ureidothiophen-2-yl)phenoxy)-1,1-dimethylpyrrolidinium

ID: ALA2425620

PubChem CID: 73352315

Max Phase: Preclinical

Molecular Formula: C18H23N4O3S+

Molecular Weight: 375.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[N+]1(C)CCC(Oc2ccccc2-c2cc(C(N)=O)c(NC(N)=O)s2)C1

Standard InChI:  InChI=1S/C18H22N4O3S/c1-22(2)8-7-11(10-22)25-14-6-4-3-5-12(14)15-9-13(16(19)23)17(26-15)21-18(20)24/h3-6,9,11H,7-8,10H2,1-2H3,(H4-,19,20,21,23,24)/p+1

Standard InChI Key:  ULTDOZRLXLILGZ-UHFFFAOYSA-O

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   14.9241   -8.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6339   -8.8983    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6329   -8.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5323  -11.5108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5311  -12.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2392  -12.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9488  -12.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9460  -11.5072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2374  -11.1019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6518  -11.0935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3995  -11.4230    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.9441  -10.8136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5328  -10.1074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7341  -10.2805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8638   -9.3574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6761   -9.2689    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.3809   -8.6981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7571  -10.8960    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.0923  -11.6413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9053  -11.7236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6145  -12.3042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2349  -10.2848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5260   -9.8783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4363   -9.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2299   -9.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7786  -10.2137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 10  2  0
  8 10  1  0
 15 16  1  0
 15 17  2  0
 13 15  1  0
 12 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
  9 22  1  0
 22 23  1  0
 23 24  1  0
 24  2  1  0
  2 25  1  0
 25 26  1  0
 26 23  1  0
M  CHG  1   2   1
M  END

Alternative Forms

1. Parent:

   

   ALA2425620

   2-(Carbamoylamino)-5-[2-(1,1-dimethylpyrrolidin-1-ium-3-yl)oxyphenyl]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: 375.47

Molecular Weight (Monoisotopic): 375.1485

AlogP: 2.23

#Rotatable Bonds: 5

Polar Surface Area: 107.44

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.55

CX Basic pKa: ┄

CX LogP: -2.38

CX LogD: -2.37

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.70

Np Likeness Score: -0.38

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