5-Amino-2-{4-[2-(2-amino-4-oxo-3,4,5,6,7,8-hexahydro-quinazolin-6-yl)-ethyl]-benzoylamino}-pentanoic acid

ID: ALA440190

PubChem CID: 136055864

Max Phase: Preclinical

Molecular Formula: C22H29N5O4

Molecular Weight: 427.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NCCCC(NC(=O)c1ccc(CCC2CCc3nc(N)nc(O)c3C2)cc1)C(=O)O

Standard InChI:  InChI=1S/C22H29N5O4/c23-11-1-2-18(21(30)31)25-19(28)15-8-5-13(6-9-15)3-4-14-7-10-17-16(12-14)20(29)27-22(24)26-17/h5-6,8-9,14,18H,1-4,7,10-12,23H2,(H,25,28)(H,30,31)(H3,24,26,27,29)

Standard InChI Key:  FLERDSAOIKEJCT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   -1.1583   -8.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5833   -8.6167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8708   -8.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1708   -9.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8708   -9.8542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5833   -9.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5542   -6.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2667   -7.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9792   -6.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4458   -8.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9792   -7.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8417   -7.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8708   -7.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4583   -9.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5542   -6.1667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2667   -5.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2958   -9.8542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1292   -6.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8417   -8.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7042   -5.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2667   -8.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4042   -8.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4167   -7.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1167   -8.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2667   -9.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6917   -8.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8417   -7.0042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9792   -8.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6917   -7.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1292   -7.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4167   -7.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  1  1  0
  4  1  2  0
  5  4  1  0
  6  5  2  0
  7 12  1  0
  8  7  1  0
  9 11  1  0
 10  1  1  0
 11  8  1  0
 12 19  2  0
 13  3  1  0
 14  4  1  0
 15  7  2  0
 16  9  2  0
 17  6  1  0
 18 23  2  0
 19 24  1  0
 20  9  1  0
 21 10  1  0
 22 26  1  0
 23 22  1  0
 24 22  2  0
 25 21  1  0
 26 28  1  0
 27 30  1  0
 28 21  1  0
 29 11  1  0
 30 31  1  0
 31 29  1  0
 14 25  1  0
  6  2  1  0
 12 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA440190

   ---

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: 427.51

Molecular Weight (Monoisotopic): 427.2220

AlogP: 1.42

#Rotatable Bonds: 9

Polar Surface Area: 164.45

Molecular Species: ZWITTERION

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.52

CX Basic pKa: 9.89

CX LogP: 0.11

CX LogD: 0.11

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.40

Np Likeness Score: 0.06

References

1. Rosowsky A, Forsch RA, Moran RG..  (1989)  (6R,6S)-5,8,10-trideaza-5,6,7,8-tetrahydrofolate and 6(R,6S)-5,8,10-trideaza-5,6,7,8-tetrahydropteroyl-L-ornithine as potential antifolates and antitumor agents.,  32  (3): [PMID:2918520] [10.1021/jm00123a037]

Source

Source(1):

• Scientific Literature