2-{4-[(2,4-Diamino-quinazolin-6-ylmethyl)-formyl-amino]-benzoylamino}-pentanedioic acid

ID: ALA303654

Chembl Id: CHEMBL303654

Cas Number: 61075-41-0

PubChem CID: 324357

Max Phase: Preclinical

Molecular Formula: C22H22N6O6

Molecular Weight: 466.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N)c2cc(CN(C=O)c3ccc(C(=O)NC(CCC(=O)O)C(=O)O)cc3)ccc2n1

Standard InChI:  InChI=1S/C22H22N6O6/c23-19-15-9-12(1-6-16(15)26-22(24)27-19)10-28(11-29)14-4-2-13(3-5-14)20(32)25-17(21(33)34)7-8-18(30)31/h1-6,9,11,17H,7-8,10H2,(H,25,32)(H,30,31)(H,33,34)(H4,23,24,26,27)

Standard InChI Key:  WFKZHYAJLQEESN-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA303654

   2-[[4-[(2,4-Diaminoquinazolin-6-yl)methyl-formylamino]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: 466.45

Molecular Weight (Monoisotopic): 466.1601

AlogP: 1.00

#Rotatable Bonds: 10

Polar Surface Area: 201.83

Molecular Species: ACID

HBA: 8

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.33

CX Basic pKa: 7.05

CX LogP: -1.38

CX LogD: -5.18

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.27

Np Likeness Score: -0.37

References

1. Hynes JB, Harmon SJ, Floyd GG, Farrington M, Hart LD, Gale GR, Washtien WL, Susten SS, Freisheim JH..  (1985)  Chemistry and antitumor evaluation of selected classical 2,4-diaminoquinazoline analogues of folic acid.,  28  (2): [PMID:3968685] [10.1021/jm00380a011]

2. Hynes JB, Patil SA, Tomazic A, Kumar A, Pathak A, Tan XH, Li XQ, Ratnam M, Delcamp TJ, Freisheim JH..  (1988)  Inhibition of murine thymidylate synthase and human dihydrofolate reductase by 5,8-dideaza analogues of folic acid and aminopterin.,  31  (2): [PMID:3339615] [10.1021/jm00397a031]

3. Crippen GM..  (1980)  Quantitative structure-activity relationships by distance geometry: systematic analysis of dihydrofolate reductase inhibitors.,  23  (6): [PMID:7392027] [10.1021/jm00180a004]

4. Ghose AK, Crippen GM..  (1982)  Quantitative structure-activity relationship by distance geometry: quinazolines as dihydrofolate reductase inhibitors.,  25  (8): [PMID:7120278] [10.1021/jm00350a003]

5. Chen BK, Horváth C, Bertino JR..  (1979)  Multivariate analysis and quantitative structure-activity relationships. Inhibition of dihydrofolate reductase and thymidylate synthetase by quinazolines.,  22  (5): [PMID:110930] [10.1021/jm00191a005]

6. Hansch C, Fukunaga JY, Jow PY..  (1977)  Quantitative structure-activity relationships of antimalarial and dihydrofolate reductase inhibition by quinazolines and 5-substituted benzyl-2,4-diaminopyrimidines.,  20  (1): [PMID:319234] [10.1021/jm00211a020]

Source

Source(1):

• Scientific Literature