ID: ALA11048

Max Phase: Preclinical

Molecular Formula: C14H12N4O4

Molecular Weight: 300.27

Molecule Type: Small molecule

Representations

Canonical SMILES:  Cn1c(=O)c2nc(-c3ccc(C(=O)O)cc3)[nH]c2n(C)c1=O

Standard InChI:  InChI=1S/C14H12N4O4/c1-17-11-9(12(19)18(2)14(17)22)15-10(16-11)7-3-5-8(6-4-7)13(20)21/h3-6H,1-2H3,(H,15,16)(H,20,21)

Standard InChI Key:  VOGIMZNURUXDIJ-UHFFFAOYSA-N

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

Properties

Molecular Weight: 300.27

Molecular Weight (Monoisotopic): 300.0859

AlogP: 0.33

#Rotatable Bonds: 2

Polar Surface Area: 109.98

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 3.90

CX Basic pKa: 1.66

CX LogP: 0.87

CX LogD: -2.47

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.71

Np Likeness Score: -0.65

References

1. Hamilton HW, Ortwine DF, Worth DF, Badger EW, Bristol JA, Bruns RF, Haleen SJ, Steffen RP..  (1985)  Synthesis of xanthines as adenosine antagonists, a practical quantitative structure-activity relationship application.,  28  (8): [PMID:2991519] [10.1021/jm00146a016]

2. Shamim MT, Ukena D, Padgett WL, Daly JW..  (1989)  Effects of 8-phenyl and 8-cycloalkyl substituents on the activity of mono-, di-, and trisubstituted alkylxanthines with substitution at the 1-, 3-, and 7-positions.,  32  (6): [PMID:2724296] [10.1021/jm00126a014]

3. Daly JW, Padgett W, Shamim MT, Butts-Lamb P, Waters J..  (1985)  1,3-Dialkyl-8-(p-sulfophenyl)xanthines: potent water-soluble antagonists for A1- and A2-adenosine receptors.,  28  (4): [PMID:2984420] [10.1021/jm00382a018]

4. Faudone G, Arifi S, Merk D..  (2021)  The Medicinal Chemistry of Caffeine.,  64  (11.0): [PMID:34019396] [10.1021/acs.jmedchem.1c00261]

Source

Source(1):

• Scientific Literature