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

ID: ALA2424670

PubChem CID: 73350829

Max Phase: Preclinical

Molecular Formula: C16H18N4O3S

Molecular Weight: 346.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)Nc1sc(-c2cccc(OC3CCNC3)c2)cc1C(N)=O

Standard InChI:  InChI=1S/C16H18N4O3S/c17-14(21)12-7-13(24-15(12)20-16(18)22)9-2-1-3-10(6-9)23-11-4-5-19-8-11/h1-3,6-7,11,19H,4-5,8H2,(H2,17,21)(H3,18,20,22)

Standard InChI Key:  XHUSGSUWISLEJZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   12.5701  -10.7060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5690  -11.5255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2770  -11.9345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9867  -11.5251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9839  -10.7024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2752  -10.2971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6896  -10.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4374  -10.6182    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.9819  -10.0088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5706   -9.3026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7720   -9.4756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9016   -8.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7140   -8.4640    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4187   -7.8933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7950  -10.0912    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1302  -10.8365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9432  -10.9188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6523  -11.4994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8623  -10.2976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8621   -9.4804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5226   -9.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2699   -8.2230    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4526   -8.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2004   -9.0004    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
  1 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2424670

   2-(Carbamoylamino)-5-(3-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: 346.41

Molecular Weight (Monoisotopic): 346.1100

AlogP: 1.75

#Rotatable Bonds: 5

Polar Surface Area: 119.47

Molecular Species: BASE

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.76

CX Basic pKa: 10.12

CX LogP: 0.83

CX LogD: -1.34

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.66

Np Likeness Score: -0.91

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