ID: ALA267803

Max Phase: Preclinical

Molecular Formula: C10H16N5O4P

Molecular Weight: 301.24

Molecule Type: Small molecule

Representations

Synonyms (1): 9-(5-Phosphonopentyl)Guanine
Synonyms from Alternative Forms(1):

Canonical SMILES:  Nc1nc(O)c2ncn(CCCCCP(=O)(O)O)c2n1

Standard InChI:  InChI=1S/C10H16N5O4P/c11-10-13-8-7(9(16)14-10)12-6-15(8)4-2-1-3-5-20(17,18)19/h6H,1-5H2,(H2,17,18,19)(H3,11,13,14,16)

Standard InChI Key:  ZQMIYPAADORARG-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: 301.24

Molecular Weight (Monoisotopic): 301.0940

AlogP: 0.46

#Rotatable Bonds: 6

Polar Surface Area: 147.38

Molecular Species: ACID

HBA: 7

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 1.87

CX Basic pKa: 0.89

CX LogP: -0.62

CX LogD: -2.67

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.44

Np Likeness Score: -0.63

References

1. Chern JW, Lee HY, Chen CS, Shewach DS, Daddona PE, Townsend LB..  (1993)  Nucleosides. 5. Synthesis of guanine and formycin B derivatives as potential inhibitors of purine nucleoside phosphorylase.,  36  (8): [PMID:8478902] [10.1021/jm00060a010]

2. Guida WC, Elliott RD, Thomas HJ, Secrist JA, Babu YS, Bugg CE, Erion MD, Ealick SE, Montgomery JA..  (1994)  Structure-based design of inhibitors of purine nucleoside phosphorylase. 4. A study of phosphate mimics.,  37  (8): [PMID:8164252] [10.1021/jm00034a008]

3. Niwas S, Chand P, Pathak VP, Montgomery JA..  (1994)  Structure-based design of inhibitors of purine nucleoside phosphorylase. 5. 9-Deazahypoxanthines.,  37  (15): [PMID:8057293] [10.1021/jm00041a027]

4. Česnek M, Hocková D, Holý A, Dračínský M, Baszczyňski O, Jersey Jd, Keough DT, Guddat LW..  (2012)  Synthesis of 9-phosphonoalkyl and 9-phosphonoalkoxyalkyl purines: evaluation of their ability to act as inhibitors of Plasmodium falciparum, Plasmodium vivax and human hypoxanthine-guanine-(xanthine) phosphoribosyltransferases.,  20  (2): [PMID:22178188] [10.1016/j.bmc.2011.11.034]

Source

Source(1):

• Scientific Literature