(S)-diethyl 2-(4-((2,4-diaminoquinazolin-6-yl)methylamino)benzamido)pentanedioate

ID: ALA3244850

PubChem CID: 90672041

Max Phase: Preclinical

Molecular Formula: C25H30N6O5

Molecular Weight: 494.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)CC[C@H](NC(=O)c1ccc(NCc2ccc3nc(N)nc(N)c3c2)cc1)C(=O)OCC

Standard InChI:  InChI=1S/C25H30N6O5/c1-3-35-21(32)12-11-20(24(34)36-4-2)29-23(33)16-6-8-17(9-7-16)28-14-15-5-10-19-18(13-15)22(26)31-25(27)30-19/h5-10,13,20,28H,3-4,11-12,14H2,1-2H3,(H,29,33)(H4,26,27,30,31)/t20-/m0/s1

Standard InChI Key:  LPCYHYYLOMBMSO-FQEVSTJZSA-N

Molfile:  

     RDKit          2D

 36 38  0  0  0  0  0  0  0  0999 V2000
   -3.9126   -9.4926    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151   -8.2668    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5094   -9.4926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5094   -8.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151   -9.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9126   -8.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8036   -9.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1367  -11.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8036   -8.2668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8507  -10.7514    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0978   -9.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2663  -10.7556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3219   -9.5050    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5565  -11.1642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4309  -10.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3921   -9.9136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0194   -9.9219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1367  -11.9690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2663   -9.9384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0978   -8.6837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7211  -11.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4309   -9.9260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0194  -10.7390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7252   -9.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6266   -8.2668    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5482  -11.9813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2540  -12.3899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9721  -11.1642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2213  -10.7184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6803  -10.7564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3875  -11.1658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2530  -13.2071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5447  -13.6186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9601  -13.6203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8359  -13.2118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1293  -13.6223    0.0000 C   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
  5 29  1  0
 28 30  1  0
 30 31  1  0
 27 32  1  0
 32 33  1  0
 32 34  2  0
 33 35  1  0
 35 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3244850

   diethyl (2S)-2-[[4-[(2,4-diaminoquinazolin-6-yl)methylamino]benzoyl]amino]pentanedioate

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: 494.55

Molecular Weight (Monoisotopic): 494.2278

AlogP: 2.41

#Rotatable Bonds: 11

Polar Surface Area: 171.55

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 7.05

CX LogP: 2.01

CX LogD: 1.87

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.29

Np Likeness Score: -0.77

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