ID: ALA418333

Max Phase: Preclinical

Molecular Formula: C17H20N4O5S

Molecular Weight: 392.44

Molecule Type: Small molecule

Representations

Canonical SMILES:  CCCn1c(=O)c2nc(-c3ccc(S(=O)(=O)O)cc3)[nH]c2n(CCC)c1=O

Standard InChI:  InChI=1S/C17H20N4O5S/c1-3-9-20-15-13(16(22)21(10-4-2)17(20)23)18-14(19-15)11-5-7-12(8-6-11)27(24,25)26/h5-8H,3-4,9-10H2,1-2H3,(H,18,19)(H,24,25,26)

Standard InChI Key:  IWALGNIFYOBRKC-UHFFFAOYSA-N

Molecule Features

Natural Product: Yes

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: 392.44

Molecular Weight (Monoisotopic): 392.1154

AlogP: 1.62

#Rotatable Bonds: 6

Polar Surface Area: 127.05

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: -2.35

CX Basic pKa: 1.70

CX LogP: -0.50

CX LogD: -0.38

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.61

Np Likeness Score: -0.94

References

1. Yan L, Müller CE..  (2004)  Preparation, properties, reactions, and adenosine receptor affinities of sulfophenylxanthine nitrophenyl esters: toward the development of sulfonic acid prodrugs with peroral bioavailability.,  47  (4): [PMID:14761205] [10.1021/jm0310030]

2. 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]

3. 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]

4. Daly JW, Padgett WL, Shamim MT..  (1986)  Analogues of 1,3-dipropyl-8-phenylxanthine: enhancement of selectivity at A1-adenosine receptors by aryl substituents.,  29  (8): [PMID:3016270] [10.1021/jm00158a034]

5. Jacobson KA, Shi D, Gallo-Rodriguez C, Manning M, Müller C, Daly JW, Neumeyer JL, Kiriasis L, Pfleiderer W..  (1993)  Effect of trifluoromethyl and other substituents on activity of xanthines at adenosine receptors.,  36  (18): [PMID:8410976] [10.1021/jm00070a007]

6. Kim HO, Ji XD, Melman N, Olah ME, Stiles GL, Jacobson KA..  (1994)  Structure-activity relationships of 1,3-dialkylxanthine derivatives at rat A3 adenosine receptors.,  37  (20): [PMID:7932565] [10.1021/jm00046a022]

7. 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]

8. Ivanov AA, Baskin II, Palyulin VA, Piccagli L, Baraldi PG, Zefirov NS..  (2005)  Molecular modeling and molecular dynamics simulation of the human A2B adenosine receptor. The study of the possible binding modes of the A2B receptor antagonists.,  48  (22): [PMID:16250640] [10.1021/jm049418o]

9. Yan L, Bertarelli DC, Hayallah AM, Meyer H, Klotz KN, Müller CE..  (2006)  A new synthesis of sulfonamides by aminolysis of p-nitrophenylsulfonates yielding potent and selective adenosine A2B receptor antagonists.,  49  (14): [PMID:16821798] [10.1021/jm060277v]

10. Diamandis P, Wildenhain J, Clarke ID, Sacher AG, Graham J, Bellows DS, Ling EK, Ward RJ, Jamieson LG, Tyers M, Dirks PB..  (2007)  Chemical genetics reveals a complex functional ground state of neural stem cells.,  3  (5): [PMID:17417631] [10.1038/nchembio873]

11. PubChem BioAssay data set, 

12. PubChem BioAssay data set, 

13. PubChem BioAssay data set, 

14. PubChem BioAssay data set, 

15. PubChem BioAssay data set, 

16. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays