(S)-5-Amino-2-{5-[(2-amino-4-oxo-3,4,5,6,7,8-hexahydro-pyrido[2,3-d]pyrimidin-6-ylmethyl)-amino]-1-oxo-1,3-dihydro-isoindol-2-yl}-pentanoic acid

ID: ALA331279

PubChem CID: 135423924

Max Phase: Preclinical

Molecular Formula: C21H27N7O4

Molecular Weight: 441.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NCCC[C@@H](C(=O)O)N1Cc2cc(NCC3CNc4nc(N)nc(O)c4C3)ccc2C1=O

Standard InChI:  InChI=1S/C21H27N7O4/c22-5-1-2-16(20(31)32)28-10-12-7-13(3-4-14(12)19(28)30)24-8-11-6-15-17(25-9-11)26-21(23)27-18(15)29/h3-4,7,11,16,24H,1-2,5-6,8-10,22H2,(H,31,32)(H4,23,25,26,27,29)/t11?,16-/m0/s1

Standard InChI Key:  DICBKNYXDPKLRB-NBFOKTCDSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  1  0  0  0  0  0999 V2000
   10.3167   -3.5667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0500   -5.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3375   -5.6375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0500   -4.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8292   -2.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6167   -4.4000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3375   -3.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6167   -5.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0500   -3.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0500   -3.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8292   -4.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7625   -5.6375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1417   -3.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1375   -2.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7625   -3.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3292   -2.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0000   -2.1167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3375   -3.1625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3292   -4.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5042   -2.3292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4792   -4.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9000   -5.6375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9042   -4.4000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4792   -5.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6167   -3.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1917   -3.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6167   -3.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8500   -2.3292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7167   -6.0417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1417   -4.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4292   -5.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4292   -4.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9667   -3.5625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2 12  1  0
  3  2  2  0
  4 15  1  0
  5  1  1  0
  6  7  1  0
  7  4  2  0
  8  3  1  0
  9  5  1  0
 10 11  1  0
 11  1  1  0
 12 24  1  0
 13  1  1  0
 14 13  1  0
 15 21  1  0
 16  9  2  0
 17  5  2  0
 18  7  1  0
 19 10  2  0
 20 14  2  0
 21 26  1  0
 22  8  1  0
 23 25  1  0
 24 21  1  0
 25 19  1  0
 26 23  1  0
 27 16  1  0
 28 14  1  0
 29 31  1  0
 30 13  1  0
 31 32  1  0
 32 30  1  0
 13 33  1  1
  9 10  1  0
 27 25  2  0
  4  2  1  0
  6  8  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA331279

   ---

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: 441.49

Molecular Weight (Monoisotopic): 441.2125

AlogP: 0.61

#Rotatable Bonds: 8

Polar Surface Area: 179.72

Molecular Species: ZWITTERION

HBA: 9

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.48

CX Basic pKa: 9.89

CX LogP: -2.07

CX LogD: -2.07

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.34

Np Likeness Score: 0.10

References

1. Rosowsky A, Forsch RA, Null A, Moran RG..  (1999)  5-deazafolate analogues with a rotationally restricted glutamate or ornithine side chain: synthesis and binding interaction with folylpolyglutamate synthetase.,  42  (18): [PMID:10479284] [10.1021/jm9807205]

Source

Source(1):

• Scientific Literature