(R)-2-[4-(2-Amino-4-oxo-3,4,5,6,7,8-hexahydro-pyrido[2,3-d]pyrimidin-6-ylmethyl)-benzoylamino]-pentanedioic acid

ID: ALA326511

PubChem CID: 136076368

Max Phase: Preclinical

Molecular Formula: C20H23N5O6

Molecular Weight: 429.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(O)c2c(n1)NCC(Cc1ccc(C(=O)N[C@H](CCC(=O)O)C(=O)O)cc1)C2

Standard InChI:  InChI=1S/C20H23N5O6/c21-20-24-16-13(18(29)25-20)8-11(9-22-16)7-10-1-3-12(4-2-10)17(28)23-14(19(30)31)5-6-15(26)27/h1-4,11,14H,5-9H2,(H,23,28)(H,26,27)(H,30,31)(H4,21,22,24,25,29)/t11?,14-/m1/s1

Standard InChI Key:  RPRBLFOFJVUMAP-SBXXRYSUSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  1  0  0  0  0  0999 V2000
   -1.1125   -1.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8208   -1.8125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1083   -0.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5333   -0.5792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8208   -0.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5333   -1.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4000   -1.8167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9000   -1.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6125   -1.4000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4292   -2.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3958   -0.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4292   -1.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1792   -1.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8208    0.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1292    0.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9042   -2.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7167   -2.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4167    1.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3167   -0.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4292   -0.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3167   -1.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4667   -1.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1792   -0.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1417   -0.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0292   -0.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1417   -2.6417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7500   -0.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8417    1.0875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4625   -0.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7542   -1.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2542   -1.4000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  5  1  0
  5  3  2  0
  6  2  1  0
  7  1  1  0
  8 13  1  0
  9  8  1  0
 12 10  1  6
 11  3  1  0
 12  9  1  1
 13 23  1  0
 14  5  1  0
 15 25  1  0
 16  8  2  0
 17 10  2  0
 18  6  1  0
 19 15  2  0
 20 22  1  0
 12 21  1  6
 22  7  1  0
 23 31  2  0
 24 30  1  0
 25 21  1  0
 26 20  1  0
 27 10  1  0
 28 26  1  0
 29 15  1  0
 30 28  2  0
 31 28  1  0
 12 32  1  1
  6  4  2  0
 11 20  1  0
 24 13  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA326511

   ---

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: 429.43

Molecular Weight (Monoisotopic): 429.1648

AlogP: 0.64

#Rotatable Bonds: 8

Polar Surface Area: 187.76

Molecular Species: ACID

HBA: 8

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.34

CX Basic pKa: 3.83

CX LogP: 0.95

CX LogD: -5.07

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.35

Np Likeness Score: 0.17

References

1. Shih C, Grindey G, Taylor E, Harrington P.  (1992)  Synthesis and biological activity of nor- and homo-5,10-dideazatetrahydrofolic acid,  2  (4): [10.1016/S0960-894X(01)80214-6]

Source

Source(1):

• Scientific Literature