ID: ALA52306

Max Phase: Preclinical

Molecular Formula: C19H24FN3O9P2

Molecular Weight: 519.36

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C(O)c1cn(C2CC2)c2cc(N3CCN(CC(P(=O)(O)O)P(=O)(O)O)CC3)c(F)cc2c1=O

Standard InChI:  InChI=1S/C19H24FN3O9P2/c20-14-7-12-15(23(11-1-2-11)9-13(18(12)24)19(25)26)8-16(14)22-5-3-21(4-6-22)10-17(33(27,28)29)34(30,31)32/h7-9,11,17H,1-6,10H2,(H,25,26)(H2,27,28,29)(H2,30,31,32)

Standard InChI Key:  HUOZBLSEUZMUDA-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: 519.36

Molecular Weight (Monoisotopic): 519.0972

AlogP: 0.98

#Rotatable Bonds: 7

Polar Surface Area: 180.84

Molecular Species: ACID

HBA: 7

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 0.69

CX Basic pKa: 7.80

CX LogP: -2.31

CX LogD: -6.60

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.33

Np Likeness Score: -0.69

References

1. Ghosh S, Chan JM, Lea CR, Meints GA, Lewis JC, Tovian ZS, Flessner RM, Loftus TC, Bruchhaus I, Kendrick H, Croft SL, Kemp RG, Kobayashi S, Nozaki T, Oldfield E..  (2004)  Effects of bisphosphonates on the growth of Entamoeba histolytica and Plasmodium species in vitro and in vivo.,  47  (1): [PMID:14695831] [10.1021/jm030084x]

2. Herczegh P, Buxton TB, McPherson JC, Kovács-Kulyassa A, Brewer PD, Sztaricskai F, Stroebel GG, Plowman KM, Farcasiu D, Hartmann JF..  (2002)  Osteoadsorptive bisphosphonate derivatives of fluoroquinolone antibacterials.,  45  (11): [PMID:12014972] [10.1021/jm0105326]

3. Houghton TJ, Tanaka KS, Kang T, Dietrich E, Lafontaine Y, Delorme D, Ferreira SS, Viens F, Arhin FF, Sarmiento I, Lehoux D, Fadhil I, Laquerre K, Liu J, Ostiguy V, Poirier H, Moeck G, Parr TR, Far AR..  (2008)  Linking bisphosphonates to the free amino groups in fluoroquinolones: preparation of osteotropic prodrugs for the prevention of osteomyelitis.,  51  (21): [PMID:18834106] [10.1021/jm801007z]

4. Prado-Prado FJ, García-Mera X, González-Díaz H..  (2010)  Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.,  18  (6): [PMID:20185316] [10.1016/j.bmc.2010.01.068]

Source

Source(1):

• Scientific Literature