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

ID: ALA366851

PubChem CID: 12659001

Max Phase: Preclinical

Molecular Formula: C16H16N6O2S

Molecular Weight: 356.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1ccc(SCCc2cnc3nc(N)nc(N)c3n2)cc1

Standard InChI:  InChI=1S/C16H16N6O2S/c1-24-15(23)9-2-4-11(5-3-9)25-7-6-10-8-19-14-12(20-10)13(17)21-16(18)22-14/h2-5,8H,6-7H2,1H3,(H4,17,18,19,21,22)

Standard InChI Key:  NHPOFMMJDAXFMC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    0.8750    0.0458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5750   -1.2042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3042    0.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2917   -0.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6000    0.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8667   -0.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0167    0.4375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0042   -1.2167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0667    0.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2417    0.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4625    0.7500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7167   -0.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6125    1.2708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1417   -1.1917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8125    0.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8417   -0.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7167   -0.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8792    0.3833    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.5917   -0.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4917   -0.6792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4542    0.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0167   -0.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9792    0.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1625   -0.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3167   -0.6542    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 18  1  0
 20  9  1  0
 21 12  1  0
 22 19  1  0
 23 19  2  0
 24 21  1  0
 25 20  1  0
  3  4  2  0
 17 12  1  0
 16 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA366851

   Methyl 4-[2-(2,4-diaminopteridin-6-yl)ethylsulfanyl]benzoate

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: 356.41

Molecular Weight (Monoisotopic): 356.1055

AlogP: 1.71

#Rotatable Bonds: 5

Polar Surface Area: 129.90

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.05

CX LogP: 1.89

CX LogD: 1.89

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.52

Np Likeness Score: -0.85

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