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

ID: ALA154418

Chembl Id: CHEMBL154418

PubChem CID: 29335

Max Phase: Preclinical

Molecular Formula: C21H22N6O5

Molecular Weight: 438.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(CNc2ccc(C(=O)NC(CC(=O)O)C(=O)O)cc2)ccc2nc(N)nc(N)c12

Standard InChI:  InChI=1S/C21H22N6O5/c1-10-12(4-7-14-17(10)18(22)27-21(23)26-14)9-24-13-5-2-11(3-6-13)19(30)25-15(20(31)32)8-16(28)29/h2-7,15,24H,8-9H2,1H3,(H,25,30)(H,28,29)(H,31,32)(H4,22,23,26,27)

Standard InChI Key:  NTKNUVXCGJPJQP-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA154418

   Methasquin

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: 438.44

Molecular Weight (Monoisotopic): 438.1652

AlogP: 1.37

#Rotatable Bonds: 8

Polar Surface Area: 193.55

Molecular Species: ACID

HBA: 8

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.75

CX Basic pKa: 7.86

CX LogP: -1.03

CX LogD: -3.46

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.30

Np Likeness Score: -0.60

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. PubChem BioAssay data set, 

4. 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]

5. 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(2):

• Scientific Literature
• PubChem BioAssays