2-{4-[(2-Amino-4-hydroxy-quinazolin-6-ylmethyl)-methyl-amino]-benzoylamino}-pentanedioic acid diethyl ester

ID: ALA156039

Chembl Id: CHEMBL156039

PubChem CID: 135467498

Max Phase: Preclinical

Molecular Formula: C26H31N5O6

Molecular Weight: 509.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)CCC(NC(=O)c1ccc(N(C)Cc2ccc3nc(N)nc(O)c3c2)cc1)C(=O)OCC

Standard InChI:  InChI=1S/C26H31N5O6/c1-4-36-22(32)13-12-21(25(35)37-5-2)28-23(33)17-7-9-18(10-8-17)31(3)15-16-6-11-20-19(14-16)24(34)30-26(27)29-20/h6-11,14,21H,4-5,12-13,15H2,1-3H3,(H,28,33)(H3,27,29,30,34)

Standard InChI Key:  ICWKNDJRQZHJHN-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA156039

   ---

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: 509.56

Molecular Weight (Monoisotopic): 509.2274

AlogP: 2.56

#Rotatable Bonds: 11

Polar Surface Area: 156.97

Molecular Species: NEUTRAL

HBA: 10

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.47

CX Basic pKa: 2.92

CX LogP: 3.17

CX LogD: 3.17

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.33

Np Likeness Score: -0.93

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