5-Amino-2-{4-[(2-amino-4-hydroxy-5,6,7,8-tetrahydro-pteridin-6-ylmethyl)-amino]-benzoylamino}-pentanoic acid

ID: ALA83868

PubChem CID: 136026478

Max Phase: Preclinical

Molecular Formula: C19H26N8O4

Molecular Weight: 430.47

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/C19H26N8O4/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/h3-6,12-13,22,24H,1-2,7-9,20H2,(H,25,28)(H,30,31)(H4,21,23,26,27,29)

Standard InChI Key:  AFOJGUSQUHNDAR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    1.8667   -3.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1500   -5.0500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8625   -4.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4375   -3.8125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1500   -3.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4375   -4.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5792   -3.3917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5792   -2.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5792   -5.0500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2917   -2.5792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0125   -1.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0125   -2.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8667   -2.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2917   -3.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5792   -1.3417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3000   -0.9292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7250   -3.8125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2917   -4.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2833   -5.0500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1500   -2.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8667   -3.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1417   -2.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4417   -3.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0125   -3.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7292   -0.9375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4375   -2.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1500   -3.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4375   -4.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7250   -2.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4375   -3.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7250   -3.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  1  1  0
  4  5  1  0
  5  1  2  0
  6  4  2  0
  7  1  1  0
  8 13  1  0
  9  3  1  0
 10  8  1  0
 11 12  1  0
 12 10  1  0
 13 21  2  0
 14  7  1  0
 15  8  2  0
 16 11  2  0
 17 24  1  0
 18 14  1  0
 19  6  1  0
 20 26  2  0
 21 27  1  0
 22  5  1  0
 23 17  1  0
 24 14  1  0
 25 11  1  0
 26 23  1  0
 27 23  2  0
 28 30  1  0
 29 12  1  0
 30 31  1  0
 31 29  1  0
  9 18  1  0
  6  2  1  0
 20 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA83868

   ---

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: 430.47

Molecular Weight (Monoisotopic): 430.2077

AlogP: 0.00

#Rotatable Bonds: 9

Polar Surface Area: 200.54

Molecular Species: ZWITTERION

HBA: 10

HBD: 8

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 10

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.48

CX Basic pKa: 9.90

CX LogP: -2.83

CX LogD: -2.83

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.27

Np Likeness Score: 0.19

References

1. Tsukamoto T, Haile WH, McGuire JJ, Coward JK..  (1996)  Synthesis and biological evaluation of N alpha-(4-amino-4-deoxy-10-methylpteroyl)-DL-4,4-difluoroornithine.,  39  (13): [PMID:8691451] [10.1021/jm960046w]

Source

Source(1):

• Scientific Literature