2-({4-[(2,4-Diamino-pteridin-6-ylmethyl)-amino]-naphthalene-1-carbonyl}-amino)-pentanedioic acid

ID: ALA335716

PubChem CID: 44354669

Max Phase: Preclinical

Molecular Formula: C23H22N8O5

Molecular Weight: 490.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N)c2nc(CNc3ccc(C(=O)NC(CCC(=O)O)C(=O)O)c4ccccc34)cnc2n1

Standard InChI:  InChI=1S/C23H22N8O5/c24-19-18-20(31-23(25)30-19)27-10-11(28-18)9-26-15-6-5-14(12-3-1-2-4-13(12)15)21(34)29-16(22(35)36)7-8-17(32)33/h1-6,10,16,26H,7-9H2,(H,29,34)(H,32,33)(H,35,36)(H4,24,25,27,30,31)

Standard InChI Key:  NXSOQESYOFTIRJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 36 39  0  0  0  0  0  0  0  0999 V2000
    0.0667   -3.9375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7792   -5.1792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4917   -3.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4917   -4.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7792   -3.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0667   -4.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1167   -2.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4042   -2.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2042   -3.5167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9750   -3.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7000   -3.1167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2125   -5.1750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1417   -3.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6250   -1.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4125   -2.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0042   -2.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7500   -2.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9250   -2.9167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9167   -3.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3667   -4.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1125   -1.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4167   -1.6875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1792   -2.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9500   -5.2417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7750   -2.7000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9250   -4.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6500   -5.1750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9917   -3.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7167   -3.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7792   -4.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9042   -1.4917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9500   -4.0667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3667   -4.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7167   -4.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9417   -5.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1125   -5.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  1  0
  3  5  2  0
  4  2  2  0
  5  1  1  0
  6  1  2  0
  7  8  1  0
  8 16  2  0
  9  3  1  0
 10 13  1  0
 11  7  1  0
 12  4  1  0
 13 17  1  0
 14 15  1  0
 15 11  1  0
 16 23  1  0
 17 18  1  0
 18 29  1  0
 19  9  2  0
 20 30  1  0
 21  7  2  0
 22 14  2  0
 23 17  2  0
 24 20  2  0
 25  5  1  0
 26 12  2  0
 27  6  1  0
 28 15  1  0
 29 19  1  0
 30 28  1  0
 31 14  1  0
 32 20  1  0
 33 10  2  0
 34 13  2  0
 35 36  2  0
 36 34  1  0
  3  4  1  0
 26 19  1  0
 10  8  1  0
 35 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA335716

   2-({4-[(2,4-Diamino-pteridin-6-ylmethyl)-amino]-naphthalene-1-carbonyl}-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: 490.48

Molecular Weight (Monoisotopic): 490.1713

AlogP: 1.40

#Rotatable Bonds: 9

Polar Surface Area: 219.33

Molecular Species: ACID

HBA: 10

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.53

CX Basic pKa: 2.89

CX LogP: 0.18

CX LogD: -6.03

Aromatic Rings: 4

Heavy Atoms: 36

QED Weighted: 0.20

Np Likeness Score: -0.47

References

1. Piper JR, Johnson CA, Maddry JA, Malik ND, McGuire JJ, Otter GM, Sirotnak FM..  (1993)  Studies on analogues of classical antifolates bearing the naphthoyl group in place of benzoyl in the side chain.,  36  (26): [PMID:8277497] [10.1021/jm00078a004]

Source

Source(1):

• Scientific Literature