5-[3-(2-Amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]-pyrimidin-6-yl)-propyl]-thiophene-2-carboxylic Acid

ID: ALA3335603

PubChem CID: 136044177

Max Phase: Preclinical

Molecular Formula: C14H14N4O3S

Molecular Weight: 318.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc2[nH]c(CCCc3ccc(C(=O)O)s3)cc2c(=O)[nH]1

Standard InChI:  InChI=1S/C14H14N4O3S/c15-14-17-11-9(12(19)18-14)6-7(16-11)2-1-3-8-4-5-10(22-8)13(20)21/h4-6H,1-3H2,(H,20,21)(H4,15,16,17,18,19)

Standard InChI Key:  JDEDSYACCNIRFX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   22.9478   -6.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3564   -7.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8086   -7.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0613   -7.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1494   -6.5760    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.2781   -5.6621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7979   -4.9989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0926   -5.5740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3563   -7.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6472   -7.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9381   -7.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1209   -5.7003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9380   -5.7003    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3466   -6.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9380   -7.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1209   -7.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7123   -6.4094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.1450   -6.5760    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4859   -7.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2290   -7.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7123   -7.8235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7123   -4.9912    0.0000 N   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
  1  5  1  0
  6  7  2  0
  6  8  1  0
  1  6  1  0
  9 10  1  0
 10 11  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 12 17  1  0
 19 20  2  0
 18 20  1  0
 14 18  1  0
 15 19  1  0
 16 21  2  0
 12 22  1  0
 11 20  1  0
  4  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3335603

   ---

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: 318.36

Molecular Weight (Monoisotopic): 318.0787

AlogP: 1.77

#Rotatable Bonds: 5

Polar Surface Area: 124.86

Molecular Species: ACID

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.35

CX Basic pKa: 4.64

CX LogP: 1.21

CX LogD: -1.10

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.57

Np Likeness Score: -0.47

References

1. Golani LK, George C, Zhao S, Raghavan S, Orr S, Wallace A, Wilson MR, Hou Z, Matherly LH, Gangjee A..  (2014)  Structure-activity profiles of novel 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolates with modified amino acids for cellular uptake by folate receptors α and β and the proton-coupled folate transporter.,  57  (19): [PMID:25234128] [10.1021/jm501113m]

Source

Source(1):

• Scientific Literature