ID: ALA236709

Max Phase: Preclinical

Molecular Formula: C11H15F2N4O4P

Molecular Weight: 336.24

Molecule Type: Small molecule

Representations

Canonical SMILES:  Nc1nc2c(CCCCC(F)(F)P(=O)(O)O)c[nH]c2c(=O)[nH]1

Standard InChI:  InChI=1S/C11H15F2N4O4P/c12-11(13,22(19,20)21)4-2-1-3-6-5-15-8-7(6)16-10(14)17-9(8)18/h5,15H,1-4H2,(H2,19,20,21)(H3,14,16,17,18)

Standard InChI Key:  OISKFAFOKMNXNK-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: 336.24

Molecular Weight (Monoisotopic): 336.0799

AlogP: 1.32

#Rotatable Bonds: 6

Polar Surface Area: 145.09

Molecular Species: ACID

HBA: 4

HBD: 5

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 0.57

CX Basic pKa: 4.78

CX LogP: 0.66

CX LogD: -2.16

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.40

Np Likeness Score: 0.15

References

1. Hikishima S, Hashimoto M, Magnowska L, Bzowska A, Yokomatsu T..  (2007)  Synthesis and biological evaluation of 9-deazaguanine derivatives connected by a linker to difluoromethylene phosphonic acid as multi-substrate analogue inhibitors of PNP.,  17  (15): [PMID:17544667] [10.1016/j.bmcl.2007.05.054]

2. Hikishima S, Hashimoto M, Magnowska L, Bzowska A, Yokomatsu T..  (2010)  Structural-based design and synthesis of novel 9-deazaguanine derivatives having a phosphate mimic as multi-substrate analogue inhibitors for mammalian PNPs.,  18  (6): [PMID:20189401] [10.1016/j.bmc.2010.01.062]

3. Wielgus-Kutrowska B, Breer K, Hashimoto M, Hikishima S, Yokomatsu T, Narczyk M, Dyzma A, Girstun A, Staroń K, Bzowska A..  (2012)  Trimeric purine nucleoside phosphorylase: exploring postulated one-third-of-the-sites binding in the transition state.,  20  (22): [PMID:23040896] [10.1016/j.bmc.2012.08.045]

Source

Source(1):

• Scientific Literature