2-{4-[(2-Amino-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-methyl-amino]-benzoylamino}-pentanedioic acid

ID: ALA347223

Chembl Id: CHEMBL347223

PubChem CID: 135777640

Max Phase: Preclinical

Molecular Formula: C22H23N5O6

Molecular Weight: 453.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(Cc1ccc2nc(N)nc(O)c2c1)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1

Standard InChI:  InChI=1S/C22H23N5O6/c1-27(11-12-2-7-16-15(10-12)20(31)26-22(23)25-16)14-5-3-13(4-6-14)19(30)24-17(21(32)33)8-9-18(28)29/h2-7,10,17H,8-9,11H2,1H3,(H,24,30)(H,28,29)(H,32,33)(H3,23,25,26,31)/t17-/m0/s1

Standard InChI Key:  ZRFBRXIIMGWDFH-KRWDZBQOSA-N

Alternative Forms

1. Parent:

   

   ALA347223

   ---

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: 453.46

Molecular Weight (Monoisotopic): 453.1648

AlogP: 1.60

#Rotatable Bonds: 9

Polar Surface Area: 178.97

Molecular Species: ACID

HBA: 8

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.25

CX Basic pKa: 2.77

CX LogP: 1.61

CX LogD: -4.39

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.32

Np Likeness Score: -0.81

References

1. Brixner DI, Ueda T, Cheng YC, Hynes JB, Broom AD..  (1987)  Folate analogues as inhibitors of thymidylate synthase.,  30  (4): [PMID:3470522] [10.1021/jm00387a016]

2. Hynes JB, Eason DE, Garrett CM, Colvin PL..  (1977)  Quinazolines as inhibitors of dihydrofolate reductase. 4. Classical analogues of folic and isofolic acids.,  20  (4): [PMID:850245] [10.1021/jm00214a030]

3. Kisliuk RL, Strumpf D, Gaumont Y, Leary RP, Plante L..  (1977)  Diastereoisomers of 5,10-methylene-5,6,7,8-tetrahydropteroyl-D-glutamic acid.,  20  (11): [PMID:410932] [10.1021/jm00221a038]

Source

Source(1):

• Scientific Literature