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

ID: ALA156237

Chembl Id: CHEMBL156237

PubChem CID: 419263

Max Phase: Preclinical

Molecular Formula: C20H20N6O5

Molecular Weight: 424.42

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  Nc1nc(N)c2cc(CNc3ccc(C(=O)NC(CC(=O)O)C(=O)O)cc3)ccc2n1

Standard InChI:  InChI=1S/C20H20N6O5/c21-17-13-7-10(1-6-14(13)25-20(22)26-17)9-23-12-4-2-11(3-5-12)18(29)24-15(19(30)31)8-16(27)28/h1-7,15,23H,8-9H2,(H,24,29)(H,27,28)(H,30,31)(H4,21,22,25,26)

Standard InChI Key:  RJMVWPJFVJJJLO-UHFFFAOYSA-N

Associated Targets(Human)

DHFR Tclin Dihydrofolate reductase (3072 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Dhfr Dihydrofolate reductase (711 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
folA Dihydrofolate reductase (93 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 424.42Molecular Weight (Monoisotopic): 424.1495AlogP: 1.06#Rotatable Bonds: 8
Polar Surface Area: 193.55Molecular Species: ACIDHBA: 8HBD: 6
#RO5 Violations: 1HBA (Lipinski): 11HBD (Lipinski): 8#RO5 Violations (Lipinski): 2
CX Acidic pKa: 4.75CX Basic pKa: 7.06CX LogP: -1.52CX LogD: -4.16
Aromatic Rings: 3Heavy Atoms: 31QED Weighted: 0.30Np Likeness Score: -0.68

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