ID: ALA414157

Max Phase: Phase

Molecular Formula: C22H32N4O4

Molecular Weight: 416.52

Molecule Type: Small molecule

Representations

Synonyms (3): Tonapofylline | BG-9928 | BG9928
Synonyms from Alternative Forms(3):

Canonical SMILES:  CCCn1c(=O)c2[nH]c(C34CCC(CCC(=O)O)(CC3)CC4)nc2n(CCC)c1=O

Standard InChI:  InChI=1S/C22H32N4O4/c1-3-13-25-17-16(18(29)26(14-4-2)20(25)30)23-19(24-17)22-10-7-21(8-11-22,9-12-22)6-5-15(27)28/h3-14H2,1-2H3,(H,23,24)(H,27,28)

Standard InChI Key:  ZWTVVWUOTJRXKM-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: Yes

Availability: No

Prodrug: No

Properties

Molecular Weight: 416.52

Molecular Weight (Monoisotopic): 416.2424

AlogP: 3.16

#Rotatable Bonds: 8

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: 4.13

CX Basic pKa:

CX LogP: 3.47

CX LogD: 0.29

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.69

Np Likeness Score: -0.11

References

1. Vu CB, Kiesman WF, Conlon PR, Lin KC, Tam M, Petter RC, Smits G, Lutterodt F, Jin X, Chen L, Zhang J..  (2006)  Tricyclic imidazoline derivatives as potent and selective adenosine A1 receptor antagonists.,  49  (24): [PMID:17125265] [10.1021/jm060539t]

2. Scheiff AB, Yerande SG, El-Tayeb A, Li W, Inamdar GS, Vasu KK, Sudarsanam V, Müller CE..  (2010)  2-Amino-5-benzoyl-4-phenylthiazoles: Development of potent and selective adenosine A1 receptor antagonists.,  18  (6): [PMID:20188574] [10.1016/j.bmc.2010.01.072]

3. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

4. Unpublished dataset, 

Source

Source(3):

• Scientific Literature
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names