(S)-2-(4-((2,4-diamino-5-chloroquinazolin-6-yl)methylamino)benzamido)pentanedioic acid

ID: ALA3244853

PubChem CID: 13833750

Max Phase: Preclinical

Molecular Formula: C21H21ClN6O5

Molecular Weight: 472.89

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N)c2c(Cl)c(CNc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)ccc2n1

Standard InChI:  InChI=1S/C21H21ClN6O5/c22-17-11(3-6-13-16(17)18(23)28-21(24)27-13)9-25-12-4-1-10(2-5-12)19(31)26-14(20(32)33)7-8-15(29)30/h1-6,14,25H,7-9H2,(H,26,31)(H,29,30)(H,32,33)(H4,23,24,27,28)/t14-/m0/s1

Standard InChI Key:  PFAJRSFHQCUKQB-AWEZNQCLSA-N

Molfile:  

     RDKit          2D

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    7.8582  -18.5271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5640  -18.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2821  -17.7099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0928  -17.2642    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5630  -19.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8547  -20.1644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2701  -20.1660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5028  -17.2642    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
  5  1  2  0
  6  1  1  0
  7  3  2  0
  8 15  1  0
  9  4  2  0
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 11  7  1  0
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 14 10  1  6
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 18  8  2  0
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 21 23  1  0
 22 24  2  0
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 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
 27 30  1  0
 30 31  1  0
 30 32  2  0
  7 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3244853

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

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: 472.89

Molecular Weight (Monoisotopic): 472.1262

AlogP: 2.11

#Rotatable Bonds: 9

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: 3.53

CX Basic pKa: 6.72

CX LogP: -0.90

CX LogD: -4.39

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.27

Np Likeness Score: -0.60

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