(S)-diethyl 2-(4-((2,4-diamino-5-chloroquinazolin-6-yl)methylamino)benzamido)succinate

ID: ALA3244848

PubChem CID: 90672039

Max Phase: Preclinical

Molecular Formula: C24H27ClN6O5

Molecular Weight: 514.97

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C[C@H](NC(=O)c1ccc(NCc2ccc3nc(N)nc(N)c3c2Cl)cc1)C(=O)OCC

Standard InChI:  InChI=1S/C24H27ClN6O5/c1-3-35-18(32)11-17(23(34)36-4-2)29-22(33)13-5-8-15(9-6-13)28-12-14-7-10-16-19(20(14)25)21(26)31-24(27)30-16/h5-10,17,28H,3-4,11-12H2,1-2H3,(H,29,33)(H4,26,27,30,31)/t17-/m0/s1

Standard InChI Key:  URPAFRKXOBUJCQ-KRWDZBQOSA-N

Molfile:  

     RDKit          2D

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   25.2009   -0.8750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   28.7379   -2.1131    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.9724   -3.7723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   23.7893   -0.8750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.9642   -4.5895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6699   -4.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3881   -3.7723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.6711   -5.8123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.3788   -4.5899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1988   -3.3265    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.0963   -3.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8035   -3.7740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   34.3807   -7.0370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6088   -3.3265    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  6  2  0
  3  5  1  0
  4  2  1  0
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  3  4  1  0
 11 20  2  0
 21 15  2  0
 27 29  1  0
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  5 31  1  0
 28 32  1  0
 32 33  1  0
 29 34  1  0
 34 35  1  0
  7 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3244848

   diethyl (2S)-2-[[4-[(2,4-diamino-5-chloroquinazolin-6-yl)methylamino]benzoyl]amino]butanedioate

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: 514.97

Molecular Weight (Monoisotopic): 514.1731

AlogP: 2.67

#Rotatable Bonds: 10

Polar Surface Area: 171.55

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: ┄

CX Basic pKa: 6.72

CX LogP: 2.33

CX LogD: 2.29

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.29

Np Likeness Score: -0.81

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