4-[2-(2,4-Diamino-pteridin-6-yl)-ethylsulfanyl]-benzoic acid

ID: ALA170135

PubChem CID: 12658994

Max Phase: Preclinical

Molecular Formula: C15H14N6O2S

Molecular Weight: 342.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N)c2nc(CCSc3ccc(C(=O)O)cc3)cnc2n1

Standard InChI:  InChI=1S/C15H14N6O2S/c16-12-11-13(21-15(17)20-12)18-7-9(19-11)5-6-24-10-3-1-8(2-4-10)14(22)23/h1-4,7H,5-6H2,(H,22,23)(H4,16,17,18,20,21)

Standard InChI Key:  ZTOXAVMHQGAQFJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   -2.2958   -3.2292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5958   -4.4875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8625   -3.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8833   -4.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5708   -2.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3083   -4.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1583   -2.8417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1708   -4.4917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8917   -3.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0667   -3.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2917   -2.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5417   -3.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5583   -2.0042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0250   -4.4667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6417   -2.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6750   -4.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5500   -4.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7125   -2.8917    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.3250   -3.9542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4167   -3.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2792   -2.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8500   -4.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8125   -2.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  2  0
  3  5  1  0
  4  2  1  0
  5  1  2  0
  6  1  1  0
  7  3  1  0
  8  4  1  0
  9 10  1  0
 10 15  2  0
 11  9  2  0
 12  7  2  0
 13  5  1  0
 14  6  1  0
 15 23  1  0
 16 22  2  0
 17  8  2  0
 18 24  1  0
 19  9  1  0
 20 18  1  0
 21 12  1  0
 22 20  1  0
 23 20  2  0
 24 21  1  0
  3  4  2  0
 17 12  1  0
 16 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA170135

   4-[2-(2,4-Diaminopteridin-6-yl)ethylsulfanyl]benzoic 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: 342.38

Molecular Weight (Monoisotopic): 342.0899

AlogP: 1.62

#Rotatable Bonds: 5

Polar Surface Area: 140.90

Molecular Species: ACID

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.11

CX Basic pKa: 2.04

CX LogP: 1.54

CX LogD: -1.56

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.59

Np Likeness Score: -0.80

References

1. Nair MG, Chen SY, Kisliuk RL, Gaumont Y, Strumpf D..  (1980)  Folate analogues altered in the C9-N10 bridge region. 16. Synthesis and antifolate activity of 11-thiohomoaminopterin.,  23  (8): [PMID:6772788] [10.1021/jm00182a017]

Source

Source(1):

• Scientific Literature