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

ID: ALA117353

PubChem CID: 136076369

Max Phase: Preclinical

Molecular Formula: C22H27N5O6

Molecular Weight: 457.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(O)c2c(n1)NCC(CCCc1ccc(C(=O)N[C@H](CCC(=O)O)C(=O)O)cc1)C2

Standard InChI:  InChI=1S/C22H27N5O6/c23-22-26-18-15(20(31)27-22)10-13(11-24-18)3-1-2-12-4-6-14(7-5-12)19(30)25-16(21(32)33)8-9-17(28)29/h4-7,13,16H,1-3,8-11H2,(H,25,30)(H,28,29)(H,32,33)(H4,23,24,26,27,31)/t13?,16-/m1/s1

Standard InChI Key:  GFHUCCQIBDDMRG-FQNRMIAFSA-N

Molfile:  

     RDKit          2D

 34 36  0  0  1  0  0  0  0  0999 V2000
   -2.4250   -1.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1333   -1.5125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4208   -0.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8375   -0.2750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1333    0.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8375   -1.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7125   -1.5125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0167   -1.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7292   -1.1000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5500   -1.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5500   -1.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7083    0.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -1.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1333    0.9625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2500    0.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0250   -2.3375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8375   -2.3375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5375    1.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5500   -0.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5875   -1.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -0.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9958   -1.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2625    0.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2625   -2.3417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9625    1.3833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9958   -0.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5792    0.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8750   -1.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8667   -0.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4375   -0.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1500    0.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2750    0.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3750   -1.1000    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
 11 10  1  6
 11  9  1  1
 12  3  1  0
 13 21  1  0
 14  5  1  0
 15 24  1  0
 16  8  2  0
 17 10  2  0
 18  6  1  0
 19 15  2  0
 11 20  1  6
 21 29  2  0
 22 28  1  0
 23  7  1  0
 24 20  1  0
 25 10  1  0
 26 15  1  0
 27 23  1  0
 28 30  2  0
 29 30  1  0
 30 32  1  0
 31 33  1  0
 32 31  1  0
 33 27  1  0
 11 34  1  1
  6  4  2  0
 12 27  1  0
 22 13  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA117353

   ---

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: 457.49

Molecular Weight (Monoisotopic): 457.1961

AlogP: 1.42

#Rotatable Bonds: 10

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: 1.84

CX LogD: -4.18

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.30

Np Likeness Score: 0.29

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