2-[4-(2,6-Dioxo-1,3-dipropyl-2,3,6,9-tetrahydro-1H-purin-8-yl)-3-hydroxy-phenoxy]-acetamide

ID: ALA158077

Chembl Id: CHEMBL158077

PubChem CID: 136191450

Max Phase: Preclinical

Molecular Formula: C19H23N5O5

Molecular Weight: 401.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCn1c(=O)c2nc(-c3ccc(OCC(N)=O)cc3O)[nH]c2n(CCC)c1=O

Standard InChI:  InChI=1S/C19H23N5O5/c1-3-7-23-17-15(18(27)24(8-4-2)19(23)28)21-16(22-17)12-6-5-11(9-13(12)25)29-10-14(20)26/h5-6,9,25H,3-4,7-8,10H2,1-2H3,(H2,20,26)(H,21,22)

Standard InChI Key:  KMGFLGAECJIANY-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA158077

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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: 401.42

Molecular Weight (Monoisotopic): 401.1699

AlogP: 0.94

#Rotatable Bonds: 8

Polar Surface Area: 145.23

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.41

CX Basic pKa: 1.50

CX LogP: 1.18

CX LogD: 0.93

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.51

Np Likeness Score: -0.87

References

1. Shamim MT, Ukena D, Padgett WL, Hong O, Daly JW..  (1988)  8-Aryl-and 8-cycloalkyl-1,3-dipropylxanthines: further potent and selective antagonists for A1-adenosine receptors.,  31  (3): [PMID:3346878] [10.1021/jm00398a020]

2. 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