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

ID: ALA2425623

PubChem CID: 58072132

Max Phase: Preclinical

Molecular Formula: C16H18N4O3S

Molecular Weight: 346.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)Nc1sc(-c2ccccc2O[C@H]2CCNC2)cc1C(N)=O

Standard InChI:  InChI=1S/C16H18N4O3S/c17-14(21)11-7-13(24-15(11)20-16(18)22)10-3-1-2-4-12(10)23-9-5-6-19-8-9/h1-4,7,9,19H,5-6,8H2,(H2,17,21)(H3,18,20,22)/t9-/m0/s1

Standard InChI Key:  PIXFUHWDLQWBQS-VIFPVBQESA-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
   13.2670   -9.4790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5552   -9.0776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4596   -8.2662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6586   -8.1044    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2571   -8.8163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8101   -9.4179    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
 20 19  1  1
 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:

   

   ALA2425623

   2-(carbamoylamino)-5-[2-[(3S)-pyrrolidin-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: 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: 10.74

CX Basic pKa: 10.09

CX LogP: 0.84

CX LogD: -1.32

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.66

Np Likeness Score: -0.62

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