2-{4-[(2-Amino-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-formyl-amino]-benzoylamino}-pentanedioic acid

ID: ALA140448

Chembl Id: CHEMBL140448

PubChem CID: 135488791

Max Phase: Preclinical

Molecular Formula: C22H21N5O7

Molecular Weight: 467.44

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H21N5O7/c23-22-25-16-6-1-12(9-15(16)20(32)26-22)10-27(11-28)14-4-2-13(3-5-14)19(31)24-17(21(33)34)7-8-18(29)30/h1-6,9,11,17H,7-8,10H2,(H,24,31)(H,29,30)(H,33,34)(H3,23,25,26,32)

Standard InChI Key:  QHUBQNFYSLRYQG-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA140448

   ---

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: 467.44

Molecular Weight (Monoisotopic): 467.1441

AlogP: 1.13

#Rotatable Bonds: 10

Polar Surface Area: 196.04

Molecular Species: ACID

HBA: 8

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.13

CX Basic pKa: 2.64

CX LogP: 0.62

CX LogD: -5.56

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.27

Np Likeness Score: -0.43

References

1. Caperelli CA, Conigliaro J..  (1986)  Synthesis of 10-acetyl-5,8-dideazafolic acid: a potent inhibitor of glycinamide ribonucleotide transformylase.,  29  (10): [PMID:3761327] [10.1021/jm00160a056]

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