4-[(2,4-Diamino-5-chloro-quinazolin-6-ylmethyl)-amino]-benzoic acid

ID: ALA155141

Chembl Id: CHEMBL155141

Cas Number: 57343-54-1

PubChem CID: 14560075

Max Phase: Preclinical

Molecular Formula: C16H14ClN5O2

Molecular Weight: 343.77

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N)c2c(Cl)c(CNc3ccc(C(=O)O)cc3)ccc2n1

Standard InChI:  InChI=1S/C16H14ClN5O2/c17-13-9(3-6-11-12(13)14(18)22-16(19)21-11)7-20-10-4-1-8(2-5-10)15(23)24/h1-6,20H,7H2,(H,23,24)(H4,18,19,21,22)

Standard InChI Key:  OARHSEZBVKKLFI-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA155141

   4-{[(2,4-Diamino-5-chloroquinazolin-6-yl)methyl]amino}benzoic 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: 343.77

Molecular Weight (Monoisotopic): 343.0836

AlogP: 2.76

#Rotatable Bonds: 4

Polar Surface Area: 127.15

Molecular Species: ACID

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.43

CX Basic pKa: 6.72

CX LogP: 0.66

CX LogD: 0.01

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.57

Np Likeness Score: -0.90

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