2-({6-[Methyl-(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-amino]-pyridine-3-carbonyl}-amino)-pentanedioic acid;monosodium salt

ID: ALA1788164

PubChem CID: 136130202

Max Phase: Preclinical

Molecular Formula: C22H22N5NaO6

Molecular Weight: 453.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc2ccc(CN(C)c3ccc(C(=O)N[C@@H](CCC(=O)[O-])C(=O)O)cn3)cc2c(=O)[nH]1.[Na+]

Standard InChI:  InChI=1S/C22H23N5O6.Na/c1-12-24-16-5-3-13(9-15(16)21(31)25-12)11-27(2)18-7-4-14(10-23-18)20(30)26-17(22(32)33)6-8-19(28)29;/h3-5,7,9-10,17H,6,8,11H2,1-2H3,(H,26,30)(H,28,29)(H,32,33)(H,24,25,31);/q;+1/p-1/t17-;/m0./s1

Standard InChI Key:  GVXLJMJARFTARX-LMOVPXPDSA-M

Molfile:  

     RDKit          2D

 34 35  0  0  0  0  0  0  0  0999 V2000
   -5.1464   -3.9751    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1464   -4.8001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4344   -5.2084    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4344   -3.5584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4344   -2.7334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7224   -3.9751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7240   -4.7982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0131   -5.2094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3000   -4.7986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3024   -3.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0139   -3.5648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5892   -3.5575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8735   -3.9677    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1603   -3.5529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5569   -3.9655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695   -3.5514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2673   -2.7256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5465   -2.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1632   -2.7320    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9799   -2.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9762   -1.4848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6927   -2.7165    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4051   -2.3004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1216   -2.7093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4009   -1.4754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1130   -1.0589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6841   -1.0661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8340   -2.2932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5505   -2.7021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5556   -3.5284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2639   -2.2873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8603   -5.2136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8708   -4.7927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8616   -0.5009    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
 15 16  1  0
  7  8  1  0
 16 17  2  0
  3  7  1  0
 17 18  1  0
  8  9  2  0
 18 19  2  0
 19 14  1  0
  6  4  1  0
 17 20  1  0
  9 10  1  0
 20 21  2  0
 20 22  1  0
 10 11  2  0
 22 23  1  0
 11  6  1  0
 23 24  1  6
  4  5  2  0
 23 25  1  0
 10 12  1  0
  1  2  1  0
 25 26  1  0
 25 27  2  0
 12 13  1  0
 24 28  1  0
  1  4  1  0
 28 29  1  0
 13 14  1  0
  6  7  2  0
 29 30  1  0
 29 31  2  0
 14 15  2  0
  2 32  1  0
  2  3  2  0
 13 33  1  0
M  CHG  2  30  -1  34   1
M  END

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: 453.46

Molecular Weight (Monoisotopic): 453.1648

AlogP: 1.31

#Rotatable Bonds: 9

Polar Surface Area: 165.58

Molecular Species: ACID

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.91

CX Basic pKa: 6.10

CX LogP: -1.41

CX LogD: -4.64

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.37

Np Likeness Score: -1.17

References

1. Marsham PR, Hughes LR, Jackman AL, Hayter AJ, Oldfield J, Wardleworth JM, Bishop JA, O'Connor BM, Calvert AH..  (1991)  Quinazoline antifolate thymidylate synthase inhibitors: heterocyclic benzoyl ring modifications.,  34  (5): [PMID:2033585] [10.1021/jm00109a011]

Source

Source(1):

• Scientific Literature