(S)-2-(4-((2,4-diaminoquinazolin-6-ylamino)methyl)benzamido)pentanedioic acid

ID: ALA464048

Chembl Id: CHEMBL464048

Cas Number: 56239-22-6

PubChem CID: 44570512

Max Phase: Preclinical

Molecular Formula: C21H22N6O5

Molecular Weight: 438.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N)c2cc(NCc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)ccc2n1

Standard InChI:  InChI=1S/C21H22N6O5/c22-18-14-9-13(5-6-15(14)26-21(23)27-18)24-10-11-1-3-12(4-2-11)19(30)25-16(20(31)32)7-8-17(28)29/h1-6,9,16,24H,7-8,10H2,(H,25,30)(H,28,29)(H,31,32)(H4,22,23,26,27)/t16-/m0/s1

Standard InChI Key:  SSPKJOYJIAOUSU-INIZCTEOSA-N

Alternative Forms

1. Parent:

   

   ALA464048

   (S)-2-(4-(((2,4-Diaminoquinazolin-6-yl)amino)methyl)benzamido)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: 438.44

Molecular Weight (Monoisotopic): 438.1652

AlogP: 1.45

#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: 7.71

CX LogP: -1.43

CX LogD: -4.53

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.28

Np Likeness Score: -0.66

References

1. Tomasić T, Zidar N, Rupnik V, Kovac A, Blanot D, Gobec S, Kikelj D, Masic LP..  (2009)  Synthesis and biological evaluation of new glutamic acid-based inhibitors of MurD ligase.,  19  (1): [PMID:19014883] [10.1016/j.bmcl.2008.10.129]

2. 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]

3. 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