ID: ALA236708

Max Phase: Preclinical

Molecular Formula: C10H14F2N5O4P

Molecular Weight: 337.22

Molecule Type: Small molecule

Representations

Canonical SMILES:  Nc1nc(O)c2ncn(CCCCC(F)(F)P(=O)(O)O)c2n1

Standard InChI:  InChI=1S/C10H14F2N5O4P/c11-10(12,22(19,20)21)3-1-2-4-17-5-14-6-7(17)15-9(13)16-8(6)18/h5H,1-4H2,(H2,19,20,21)(H3,13,15,16,18)

Standard InChI Key:  JANQQPWTLXUSCD-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: 337.22

Molecular Weight (Monoisotopic): 337.0751

AlogP: 1.05

#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: 0.42

CX Basic pKa: 1.10

CX LogP: -0.49

CX LogD: -2.40

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.45

Np Likeness Score: -0.73

References

1. Yokomatsu T, Hayakawa Y, Suemune K, Kihara T, Soeda S, Shimeno H, Shibuya S..  (1999)  Synthesis and biological evaluation of 1,1-difluoro-2-(tetrahydro-3-furanyl)ethylphosphonic acids possessing a N9-purinylmethyl functional group at the ring. a new class of inhibitors for purine nucleoside phosphorylases.,  9  (19): [PMID:10522701] [10.1016/s0960-894x(99)00495-3]

2. Halazy S, Eggenspiller A, Ehrhard A, Danzin C.  (1992)  Phosphonate derivatives of N9-benzylguanine: a new class of potent purine nucleoside phosphorylase inhibitors,  2  (5): [10.1016/S0960-894X(00)80157-2]

3. 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]

4. 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]

5. Diab SA, De Schutter C, Muzard M, Plantier-Royon R, Pfund E, Lequeux T..  (2012)  Fluorophosphonylated nucleoside derivatives as new series of thymidine phosphorylase multisubstrate inhibitors.,  55  (6): [PMID:22372816] [10.1021/jm201694y]

6. 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]

7. Downey AM, Cairo CW.  (2014)  Synthesis of -brominated phosphonates and their application as phosphate bioisosteres,  5  (11): [10.1039/C4MD00255E]

Source

Source(1):

• Scientific Literature