N-{4-[2-(2-Amino-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-6-yl)-ethyl]benzoyl}-L-glutamic Acid

ID: ALA522455

PubChem CID: 42637226

Max Phase: Preclinical

Molecular Formula: C20H20N4O6S

Molecular Weight: 444.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc2sc(CCc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)cc2c(=O)[nH]1

Standard InChI:  InChI=1S/C20H20N4O6S/c21-20-23-17(28)13-9-12(31-18(13)24-20)6-3-10-1-4-11(5-2-10)16(27)22-14(19(29)30)7-8-15(25)26/h1-2,4-5,9,14H,3,6-8H2,(H,22,27)(H,25,26)(H,29,30)(H3,21,23,24,28)/t14-/m0/s1

Standard InChI Key:  SPLMCWYQFZQLIA-AWEZNQCLSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   -2.8201    1.9947    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8235    1.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1127    0.7563    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1058    2.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3992    1.9888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4027    1.1628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6180    0.9055    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1278    1.5683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6123    2.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5397    0.7571    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1024    3.2312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6970    1.5648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1146    2.2781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9396    2.2746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3443    1.5584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1685    1.5545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5868    2.2683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1709    2.9874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3480    2.9877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4118    2.2660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8201    1.5498    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8243    2.9797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6451    1.5474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0576    0.8313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0617    2.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8867    2.2588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6492    2.9774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8826    0.8289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2910    0.1168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1159    0.1144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8785   -0.5970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  2  0
  3  6  1  0
 15 16  1  0
  6  7  1  0
 16 17  2  0
  7  8  1  0
 17 18  1  0
  8  9  2  0
 18 19  2  0
 19 14  1  0
  9  5  1  0
 17 20  1  0
  5  4  1  0
 20 21  1  0
  2 10  1  0
 20 22  2  0
  5  6  2  0
 21 23  1  0
  4 11  2  0
 23 24  1  0
 23 25  1  6
  8 12  1  0
 25 26  1  0
  1  2  1  0
 25 27  2  0
 12 13  1  0
 24 28  1  0
  1  4  1  0
 28 29  1  0
 13 14  1  0
 29 30  2  0
  2  3  2  0
 29 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA522455

   (2S)-2-[[4-[2-(2-amino-4-oxo-3H-thieno[2,3-d]pyrimidin-6-yl)ethyl]benzoyl]amino]pentanedioic acid

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: 444.47

Molecular Weight (Monoisotopic): 444.1104

AlogP: 1.40

#Rotatable Bonds: 9

Polar Surface Area: 175.47

Molecular Species: ACID

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.34

CX Basic pKa: 2.31

CX LogP: 1.63

CX LogD: -4.65

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.33

Np Likeness Score: -0.50

References

1. Deng Y, Zhou X, Kugel Desmoulin S, Wu J, Cherian C, Hou Z, Matherly LH, Gangjee A..  (2009)  Synthesis and biological activity of a novel series of 6-substituted thieno[2,3-d]pyrimidine antifolate inhibitors of purine biosynthesis with selectivity for high affinity folate receptors over the reduced folate carrier and proton-coupled folate transporter for cellular entry.,  52  (9): [PMID:19371039] [10.1021/jm8011323]

Source

Source(1):

• Scientific Literature