ID: ALA383917

Max Phase: Preclinical

Molecular Formula: C18H24FN5O2

Molecular Weight: 361.42

Molecule Type: Small molecule

Representations

Synonyms (1): PD-0305970
Synonyms from Alternative Forms(1):

Canonical SMILES:  Cc1c(N2CC[C@@H]([C@H](C)N)C2)c(F)cc2c(=O)n(N)c(=O)n(C3CC3)c12

Standard InChI:  InChI=1S/C18H24FN5O2/c1-9-15-13(17(25)24(21)18(26)23(15)12-3-4-12)7-14(19)16(9)22-6-5-11(8-22)10(2)20/h7,10-12H,3-6,8,20-21H2,1-2H3/t10-,11+/m0/s1

Standard InChI Key:  SMONLCFJGCJROJ-WDEREUQCSA-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: 361.42

Molecular Weight (Monoisotopic): 361.1914

AlogP: 0.83

#Rotatable Bonds: 3

Polar Surface Area: 99.28

Molecular Species: BASE

HBA: 7

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 10.07

CX LogP: 1.23

CX LogD: -1.28

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.79

Np Likeness Score: -0.76

References

1. Ellsworth EL, Tran TP, Showalter HD, Sanchez JP, Watson BM, Stier MA, Domagala JM, Gracheck SJ, Joannides ET, Shapiro MA, Dunham SA, Hanna DL, Huband MD, Gage JW, Bronstein JC, Liu JY, Nguyen DQ, Singh R..  (2006)  3-aminoquinazolinediones as a new class of antibacterial agents demonstrating excellent antibacterial activity against wild-type and multidrug resistant organisms.,  49  (22): [PMID:17064062] [10.1021/jm060505l]

2. Huband MD, Cohen MA, Zurack M, Hanna DL, Skerlos LA, Sulavik MC, Gibson GW, Gage JW, Ellsworth E, Stier MA, Gracheck SJ..  (2007)  In vitro and in vivo activities of PD 0305970 and PD 0326448, new bacterial gyrase/topoisomerase inhibitors with potent antibacterial activities versus multidrug-resistant gram-positive and fastidious organism groups.,  51  (4): [PMID:17261623] [10.1128/aac.01321-06]

3. Tran TP, Ellsworth EL, Sanchez JP, Watson BM, Stier MA, Showalter HD, Domagala JM, Shapiro MA, Joannides ET, Gracheck SJ, Nguyen DQ, Bird P, Yip J, Sharadendu A, Ha C, Ramezani S, Wu X, Singh R..  (2007)  Structure-activity relationships of 3-aminoquinazolinediones, a new class of bacterial type-2 topoisomerase (DNA gyrase and topo IV) inhibitors.,  17  (5): [PMID:17196390] [10.1016/j.bmcl.2006.12.005]

4. Hutchings KM, Tran TP, Ellsworth EL, Watson BM, Sanchez JP, Showalter HD, Stier MA, Shapiro M, Themis Joannides E, Huband M, Nguyen DQ, Maiti S, Li T, Tailor J, Thomas G, Ha C, Singh R..  (2008)  Synthesis and antibacterial activity of the C-7 side chain of 3-aminoquinazolinediones.,  18  (18): [PMID:18752951] [10.1016/j.bmcl.2008.07.117]

5. Skepper CK, Armstrong D, Balibar CJ, Bauer D, Bellamacina C, Benton BM, Bussiere D, De Pascale G, De Vicente J, Dean CR, Dhumale B, Fisher LM, Fuller J, Fulsunder M, Holder LM, Hu C, Kantariya B, Lapointe G, Leeds JA, Li X, Lu P, Lvov A, Ma S, Madhavan S, Malekar S, McKenney D, Mergo W, Metzger L, Moser HE, Mutnick D, Noeske J, Osborne C, Patel A, Patel D, Patel T, Prajapati K, Prosen KR, Reck F, Richie DL, Rico A, Sanderson MR, Satasia S, Sawyer WS, Selvarajah J, Shah N, Shanghavi K, Shu W, Thompson KV, Traebert M, Vala A, Vala L, Veselkov DA, Vo J, Wang M, Widya M, Williams SL, Xu Y, Yue Q, Zang R, Zhou B, Rivkin A..  (2020)  Topoisomerase Inhibitors Addressing Fluoroquinolone Resistance in Gram-Negative Bacteria.,  63  (14): [PMID:32634310] [10.1021/acs.jmedchem.0c00347]

Source

Source(1):

• Scientific Literature