4-[(2,4-Diamino-quinazolin-6-ylmethyl)-amino]-benzoic acid ethyl ester

ID: ALA157456

Chembl Id: CHEMBL157456

PubChem CID: 44371104

Max Phase: Preclinical

Molecular Formula: C18H19N5O2

Molecular Weight: 337.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1ccc(NCc2ccc3nc(N)nc(N)c3c2)cc1

Standard InChI:  InChI=1S/C18H19N5O2/c1-2-25-17(24)12-4-6-13(7-5-12)21-10-11-3-8-15-14(9-11)16(19)23-18(20)22-15/h3-9,21H,2,10H2,1H3,(H4,19,20,22,23)

Standard InChI Key:  DJQDLDRRHQWYCG-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA157456

   Ethyl 4-[(2,4-diaminoquinazolin-6-yl)methylamino]benzoate

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: 337.38

Molecular Weight (Monoisotopic): 337.1539

AlogP: 2.58

#Rotatable Bonds: 5

Polar Surface Area: 116.15

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.99

CX LogP: 2.60

CX LogD: 2.46

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.61

Np Likeness Score: -1.00

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. 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]

4. 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