(S)-2-({2-[4-(2-Amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]-pyrimidin-6-yl)butyl]thiophene-3-carbonyl}amino)pentanedioic Acid

ID: ALA2158678

PubChem CID: 136020100

Max Phase: Preclinical

Molecular Formula: C20H23N5O6S

Molecular Weight: 461.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc2[nH]c(CCCCc3sccc3C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc2c(=O)[nH]1

Standard InChI:  InChI=1S/C20H23N5O6S/c21-20-24-16-12(18(29)25-20)9-10(22-16)3-1-2-4-14-11(7-8-32-14)17(28)23-13(19(30)31)5-6-15(26)27/h7-9,13H,1-6H2,(H,23,28)(H,26,27)(H,30,31)(H4,21,22,24,25,29)/t13-/m0/s1

Standard InChI Key:  KPLUEWVRYVJTJJ-ZDUSSCGKSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
    3.7034   -3.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6762   -2.2345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3739   -1.8013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1016   -2.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8023   -1.7506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4312   -3.4480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0056   -3.4936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5260   -2.1394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7709   -0.9259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9483   -1.8470    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9183   -1.0262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6418   -0.6255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4267   -0.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2154   -0.6012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2212    0.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4435    0.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9484   -0.1730    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0230   -1.5650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1993   -1.5746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2209   -0.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0446   -0.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4079   -4.1422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7020   -3.7221    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7116   -2.8983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4270   -2.4947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1370   -2.9149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1275   -3.7387    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1024   -2.3431    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2684   -1.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4482   -1.5936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8566   -2.5112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3983   -4.9660    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  1  6  2  0
  1  7  1  0
  5  8  2  0
  5  9  1  0
 11 12  2  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 13 17  1  0
 11 14  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 22 27  1  0
 29 30  2  0
 28 30  1  0
 24 28  1  0
 25 29  1  0
 26 31  2  0
 22 32  1  0
 21 30  1  0
 13 18  1  0
 10 11  1  0
  2 10  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA2158678

   ---

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: 461.50

Molecular Weight (Monoisotopic): 461.1369

AlogP: 1.51

#Rotatable Bonds: 11

Polar Surface Area: 191.26

Molecular Species: ACID

HBA: 7

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.73

CX Basic pKa: 4.90

CX LogP: 0.61

CX LogD: -4.39

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.23

Np Likeness Score: -0.27

References

1. Wang L, Cherian C, Kugel Desmoulin S, Mitchell-Ryan S, Hou Z, Matherly LH, Gangjee A..  (2012)  Synthesis and biological activity of 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl regioisomers as inhibitors of de novo purine biosynthesis with selectivity for cellular uptake by high affinity folate receptors and the proton-coupled folate transporter over the reduced folate carrier.,  55  (4): [PMID:22243528] [10.1021/jm201688n]

Source

Source(1):

• Scientific Literature