2-{4-[(2,4-Diamino-5-chloro-quinazolin-6-ylmethyl)-amino]-benzoylamino}-succinic acid diethyl ester

ID: ALA346513

Chembl Id: CHEMBL346513

PubChem CID: 44370335

Max Phase: Preclinical

Molecular Formula: C24H27ClN6O5

Molecular Weight: 514.97

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)CC(NC(=O)c1ccc(NCc2ccc3nc(N)nc(N)c3c2Cl)cc1)C(=O)OCC

Standard InChI:  InChI=1S/C24H27ClN6O5/c1-3-35-18(32)11-17(23(34)36-4-2)29-22(33)13-5-8-15(9-6-13)28-12-14-7-10-16-19(20(14)25)21(26)31-24(27)30-16/h5-10,17,28H,3-4,11-12H2,1-2H3,(H,29,33)(H4,26,27,30,31)

Standard InChI Key:  URPAFRKXOBUJCQ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA346513

   Diethyl 2-[[4-[(2,4-diamino-5-chloroquinazolin-6-yl)methylamino]benzoyl]amino]butanedioate

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: 514.97

Molecular Weight (Monoisotopic): 514.1731

AlogP: 2.67

#Rotatable Bonds: 10

Polar Surface Area: 171.55

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: ┄

CX Basic pKa: 6.72

CX LogP: 2.33

CX LogD: 2.29

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.29

Np Likeness Score: -0.81

References

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

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

3. 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