5-Amino-2-{4-[(2-amino-4-oxo-3,4-dihydro-pteridin-6-ylmethyl)-amino]-benzoylamino}-pentanoic acid

ID: ALA41743

PubChem CID: 136046101

Max Phase: Preclinical

Molecular Formula: C19H22N8O4

Molecular Weight: 426.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NCCCC(NC(=O)c1ccc(NCc2cnc3nc(N)nc(O)c3n2)cc1)C(=O)O

Standard InChI:  InChI=1S/C19H22N8O4/c20-7-1-2-13(18(30)31)25-16(28)10-3-5-11(6-4-10)22-8-12-9-23-15-14(24-12)17(29)27-19(21)26-15/h3-6,9,13,22H,1-2,7-8,20H2,(H,25,28)(H,30,31)(H3,21,23,26,27,29)

Standard InChI Key:  ODGLNGSSLASZFM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    2.0042   -1.1042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292   -0.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4917   -0.2042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5250   -0.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0042    0.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4875   -0.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0417    0.0958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6667    1.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0417   -1.1042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1917    0.7208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7042    1.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7125    1.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1542    0.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5625   -0.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0042    0.6958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6667    1.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1792    1.9208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9667   -1.1000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6000   -0.1917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5625   -0.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6292    1.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1542    0.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0792    0.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1167    0.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2250    1.9208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6375   -0.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1125    0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7625   -0.7792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2292    0.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7542   -0.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2375    0.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  3  6  2  0
  4  1  2  0
  5  3  1  0
  6  1  1  0
  7  2  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 20  1  0
 15  5  1  0
 16  8  2  0
 17 11  2  0
 18  6  1  0
 19 23  1  0
 20  9  2  0
 21 27  1  0
 22 26  2  0
 23 14  1  0
 24 19  1  0
 25 11  1  0
 26 24  1  0
 27 24  2  0
 28 30  1  0
 29 12  1  0
 30 31  1  0
 31 29  1  0
  2  5  2  0
 14  7  2  0
 22 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA41743

   ---

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: 426.44

Molecular Weight (Monoisotopic): 426.1764

AlogP: 0.24

#Rotatable Bonds: 9

Polar Surface Area: 202.26

Molecular Species: ZWITTERION

HBA: 10

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.48

CX Basic pKa: 11.10

CX LogP: -2.60

CX LogD: -2.60

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.27

Np Likeness Score: -0.44

References

1. Patil SA, Shane B, Freisheim JH, Singh SK, Hynes JB..  (1989)  Inhibition of mammalian folylpolyglutamate synthetase and human dihydrofolate reductase by 5,8-dideaza analogues of folic acid and aminopterin bearing a terminal L-ornithine.,  32  (7): [PMID:2738891] [10.1021/jm00127a026]

2. Singh SK, Singer SC, Ferone R, Waters KA, Mullin RJ, Hynes JB..  (1992)  Synthesis and biological evaluation of N alpha-(5-deaza-5,6,7,8-tetrahydropteroyl)-L-ornithine.,  35  (11): [PMID:1375963] [10.1021/jm00089a009]

3. Hynes JB, Singh SK, Fetzer O, Shane B..  (1992)  Inhibition of hog liver folylpolyglutamate synthetase by 5-substituted 5,8-dideaza analogues of folic acid bearing a terminal L-ornithine residue.,  35  (22): [PMID:1433214] [10.1021/jm00100a013]

Source

Source(1):

• Scientific Literature