(S)-2-(4-((2,4-diamino-5-methylquinazolin-6-ylamino)methyl)benzamido)pentanedioic acid

ID: ALA3244859

Chembl Id: CHEMBL3244859

PubChem CID: 90672047

Max Phase: Preclinical

Molecular Formula: C22H24N6O5

Molecular Weight: 452.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(NCc2ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc2)ccc2nc(N)nc(N)c12

Standard InChI:  InChI=1S/C22H24N6O5/c1-11-14(6-7-15-18(11)19(23)28-22(24)27-15)25-10-12-2-4-13(5-3-12)20(31)26-16(21(32)33)8-9-17(29)30/h2-7,16,25H,8-10H2,1H3,(H,26,31)(H,29,30)(H,32,33)(H4,23,24,27,28)/t16-/m0/s1

Standard InChI Key:  MKOYTAPWWOTATD-INIZCTEOSA-N

Alternative Forms

1. Parent:

   

   ALA3244859

   (2S)-2-[[4-[[(2,4-diamino-5-methylquinazolin-6-yl)amino]methyl]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: 452.47

Molecular Weight (Monoisotopic): 452.1808

AlogP: 1.76

#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: 3.52

CX Basic pKa: 8.04

CX LogP: -0.93

CX LogD: -3.92

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.28

Np Likeness Score: -0.59

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]

2. Fukunaga JY, Hansch C, Steller EE..  (1976)  Inhibition of dihydrofolate reductase. Structure-activity correlations of quinazolines.,  19  (5): [PMID:1271401] [10.1021/jm00227a006]

Source

Source(1):

• Scientific Literature