5-Amino-2-{4-[(2,4-diamino-pteridin-6-ylmethyl)-amino]-benzoylamino}-pentanoic acid

ID: ALA281656

PubChem CID: 14083106

Max Phase: Preclinical

Molecular Formula: C19H23N9O3

Molecular Weight: 425.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NCCC[C@H](NC(=O)c1ccc(NCc2cnc3nc(N)nc(N)c3n2)cc1)C(=O)O

Standard InChI:  InChI=1S/C19H23N9O3/c20-7-1-2-13(18(30)31)26-17(29)10-3-5-11(6-4-10)23-8-12-9-24-16-14(25-12)15(21)27-19(22)28-16/h3-6,9,13,23H,1-2,7-8,20H2,(H,26,29)(H,30,31)(H4,21,22,24,27,28)/t13-/m0/s1

Standard InChI Key:  WNGBWNCQSARWSJ-ZDUSSCGKSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  1  0  0  0  0  0999 V2000
    0.8792   -4.9000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7917   -5.9875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2792   -4.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4167   -5.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5042   -4.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0250   -5.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9125   -4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6375   -2.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1875   -5.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4042   -2.3667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8292   -2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0875   -1.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0042   -2.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6875   -4.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5042   -1.2667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5125   -1.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0917   -4.1792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3542   -3.5500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8292   -5.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3875   -6.2292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1417   -3.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2250   -2.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3167   -3.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7292   -3.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9000   -3.0792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5917   -2.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5000   -3.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4625    0.4583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0250   -1.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2125    0.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2792   -0.7250    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  3  1  0
  8 13  1  0
  9  4  1  0
 10  8  1  0
 11 12  1  0
 12 10  1  0
 13 21  2  0
 14  7  2  0
 15  8  2  0
 16 11  2  0
 17 23  1  0
 18  5  1  0
 19  9  2  0
 20  6  1  0
 21 27  1  0
 22 26  2  0
 23 14  1  0
 24 17  1  0
 25 11  1  0
 26 24  1  0
 27 24  2  0
 28 30  1  0
 12 29  1  1
 30 31  1  0
 31 29  1  0
  4  3  1  0
 14 19  1  0
 13 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA281656

   (2S)-5-amino-2-[[4-[(2,4-diaminopteridin-6-yl)methylamino]benzoyl]amino]pentanoic 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: 425.45

Molecular Weight (Monoisotopic): 425.1924

AlogP: 0.12

#Rotatable Bonds: 9

Polar Surface Area: 208.05

Molecular Species: ZWITTERION

HBA: 10

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.48

CX Basic pKa: 9.90

CX LogP: -3.12

CX LogD: -3.12

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.27

Np Likeness Score: -0.41

References

1. Rosowsky A, Bader H, Kohler W, Freisheim JH, Moran RG..  (1988)  Methotrexate analogues. 34. Replacement of the glutamate moiety in methotrexate and aminopterin by long-chain 2-aminoalkanedioic acids.,  31  (7): [PMID:2898531] [10.1021/jm00402a014]

Source

Source(1):

• Scientific Literature