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4-[(2-Amino-4-hydroxy-quinazolin-6-ylmethyl)-amino]-benzoic acid

ID: ALA422159

Chembl Id: CHEMBL422159

PubChem CID: 136040428

Max Phase: Preclinical

Molecular Formula: C16H14N4O3

Molecular Weight: 310.31

Molecule Type: Small molecule

Associated Items:

Bioactivity Summary Target Summary Assay Summary

Names and Identifiers

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

Standard InChI: InChI=1S/C16H14N4O3/c17-16-19-13-6-1-9(7-12(13)14(21)20-16)8-18-11-4-2-10(3-5-11)15(22)23/h1-7,18H,8H2,(H,22,23)(H3,17,19,20,21)

Standard InChI Key: OKJTWJFPULDSSA-UHFFFAOYSA-N

DHFR Tclin Dihydrofolate reductase (3072 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Tyms Thymidylate synthase (842 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

thyA Thymidylate synthase (501 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

folA Dihydrofolate reductase (93 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

MESH ID	MESH Heading	EFO IDs	EFO Terms	Max Phase for Indication	References

Mechanism of Action	Action Type	target ID	Target Name	Target Type	Target Organism	Binding Site Name	References

Molecular Weight: 310.31	Molecular Weight (Monoisotopic): 310.1066	AlogP: 2.23	#Rotatable Bonds: 4
Polar Surface Area: 121.36	Molecular Species: ACID	HBA: 6	HBD: 4
#RO5 Violations: ┄	HBA (Lipinski): 7	HBD (Lipinski): 5	#RO5 Violations (Lipinski): ┄
CX Acidic pKa: 4.74	CX Basic pKa: 2.97	CX LogP: 2.30	CX LogD: -0.20
Aromatic Rings: 3	Heavy Atoms: 23	QED Weighted: 0.58	Np Likeness Score: -0.99

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]

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