(S)-2-(4-((2,4-diaminoquinazolin-6-yl)methylamino)benzamido)succinic acid

ID: ALA3244847

Cas Number: 18921-65-8

PubChem CID: 29334

Max Phase: Preclinical

Molecular Formula: C20H20N6O5

Molecular Weight: 424.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N)c2cc(CNc3ccc(C(=O)N[C@@H](CC(=O)O)C(=O)O)cc3)ccc2n1

Standard InChI:  InChI=1S/C20H20N6O5/c21-17-13-7-10(1-6-14(13)25-20(22)26-17)9-23-12-4-2-11(3-5-12)18(29)24-15(19(30)31)8-16(27)28/h1-7,15,23H,8-9H2,(H,24,29)(H,27,28)(H,30,31)(H4,21,22,25,26)/t15-/m0/s1

Standard InChI Key:  RJMVWPJFVJJJLO-HNNXBMFYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   11.4696   -0.9616    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1671    0.2641    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8728   -0.9616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8728   -0.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1671   -1.3702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4696   -0.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5786   -1.3702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5189   -2.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5786    0.2641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2329   -2.2204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2843   -0.9699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6485   -2.2246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7041   -0.9740    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9386   -2.6332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8131   -2.2122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9901   -1.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4016   -1.3909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5189   -3.4380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6485   -1.4074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2843   -0.1527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1032   -2.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8131   -1.3950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4016   -2.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1074   -0.9864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7556    0.2641    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9304   -3.4504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6361   -3.8590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3543   -2.6332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6374   -4.6732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3451   -3.4508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1650   -2.1874    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  2  0
  3  5  1  0
  4  2  1  0
  5  1  2  0
  6  1  1  0
  7  3  2  0
  8 15  1  0
  9  4  2  0
 10  8  1  0
 11  7  1  0
 12 14  1  0
 13 16  1  0
 14 10  1  6
 15 22  1  0
 16 11  1  0
 17 13  1  0
 18  8  2  0
 19 12  2  0
 20  9  1  0
 21 23  1  0
 22 24  2  0
 23 17  2  0
 24 17  1  0
 25  6  1  0
 26 14  1  0
 27 26  1  0
 28 12  1  0
  3  4  1  0
 11 20  2  0
 21 15  2  0
 27 29  1  0
 27 30  2  0
  5 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3244847

   Quinaspar

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: 424.42

Molecular Weight (Monoisotopic): 424.1495

AlogP: 1.06

#Rotatable Bonds: 8

Polar Surface Area: 193.55

Molecular Species: ACID

HBA: 8

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.75

CX Basic pKa: 7.06

CX LogP: -1.52

CX LogD: -4.16

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.30

Np Likeness Score: -0.68

References

1. Hynes JB, Eason DE, Garrett CM, Colvin PL..  (1977)  Quinazolines as inhibitors of dihydrofolate reductase. 4. Classical analogues of folic and isofolic acids.,  20  (4): [PMID:850245] [10.1021/jm00214a030]

Source

Source(1):

• Scientific Literature