2-{4-[(2-Amino-4-oxo-1,4-dihydro-quinazolin-6-ylmethyl)-amino]-benzoylamino}-pentanedioic acid (DDF)

ID: ALA22973

Chembl Id: CHEMBL22973

PubChem CID: 135600305

Max Phase: Preclinical

Molecular Formula: C21H21N5O6

Molecular Weight: 439.43

Molecule Type: Small molecule

Names and Identifiers

Synonyms: TCMDC-132046 | TCMDC-132046

Canonical SMILES:  Nc1nc(O)c2cc(CNc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)ccc2n1

Standard InChI:  InChI=1S/C21H21N5O6/c22-21-25-15-6-1-11(9-14(15)19(30)26-21)10-23-13-4-2-12(3-5-13)18(29)24-16(20(31)32)7-8-17(27)28/h1-6,9,16,23H,7-8,10H2,(H,24,29)(H,27,28)(H,31,32)(H3,22,25,26,30)/t16-/m0/s1

Standard InChI Key:  UQFCLENKCDVITL-INIZCTEOSA-N

Alternative Forms

1. Parent:

   

   ALA22973

   ---

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: 439.43

Molecular Weight (Monoisotopic): 439.1492

AlogP: 1.58

#Rotatable Bonds: 9

Polar Surface Area: 187.76

Molecular Species: ACID

HBA: 8

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.32

CX Basic pKa: 3.56

CX LogP: 0.76

CX LogD: -5.00

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.29

Np Likeness Score: -0.66

References

1. Nair MG, Dhawan R, Ghazala M, Kalman TI, Ferone R, Gaumont Y, Kisliuk RL..  (1987)  Folate analogues. 30. Synthesis and biological evaluation of N10-propargyl-5,8-dideaza-5,6,7,8-tetrahydrofolic acid and related compounds.,  30  (7): [PMID:3599032] [10.1021/jm00390a025]

2. 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]

3. Gamo FJ, Sanz LM, Vidal J, de Cozar C, Alvarez E, Lavandera JL, Vanderwall DE, Green DV, Kumar V, Hasan S, Brown JR, Peishoff CE, Cardon LR, Garcia-Bustos JF..  (2010)  Thousands of chemical starting points for antimalarial lead identification.,  465  (7296): [PMID:20485427] [10.1038/nature09107]

4. 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]

Source

Source(2):

• Scientific Literature
• GSK Malaria Screening