M.

Mudassar Ali

Ciprofloxacin
M. Mudassar Ali

Physicochemical Properties
Formula C17H18FN3O3
Molecular weight 331.34 g/mol
Num. heavy atoms 24
Num. arom. heavy atoms 10
Fraction Csp3 0.41
Num. rotatable bonds 3
Num. H-bond acceptors 5
Num. H-bond donors 2
Molar Refractivity 95.25
TPSA 74.57 Ų
Lipophilicity
Log Po/w (iLOGP) 2.24
Log Po/w (XLOGP3) -1.08
Log Po/w (WLOGP) 1.18
Log Po/w (MLOGP) 1.28
Log Po/w (SILICOS-IT) 1.90
Consensus Log Po/w 1.10
Water Solubility
Log S (ESOL) -1.32
Solubility 1.57e+01 mg/ml ; 4.74e-02
mol/l
Class Very soluble
Log S (Ali) 0.00
Solubility 3.34e+02 mg/ml ; 1.01e+00
mol/l
Class Highly soluble
Log S (SILICOS-IT) -3.50
Solubility 1.04e-01 mg/ml ; 3.13e-04
mol/l
Class Soluble
Pharmacokinetics
GI absorption High
BBB permeant No
P-gp substrate Yes
CYP1A2 inhibitor No
CYP2C19 inhibitor No
CYP2C9 inhibitor No
CYP2D6 inhibitor No
CYP3A4 inhibitor No
Log Kp (skin -9.09 cm/s
permeation)
M. Mudassar Ali

Druglikeness
Lipinski Yes; 0 violation
Ghose Yes
Veber Yes
Egan Yes
Muegge Yes
Bioavailability Score 0.55
Medicinal Chemistry

PAINS 0 alert
Brenk 0 alert
Leadlikeness Yes
Synthetic accessibility 2.51

pkCSM:

Property Model Name Predicted Value Unit

Absorption Water solubility Running Numeric (log mol/L)
Absorption Caco2 permeability Running Numeric (log Papp in 10-
6
cm/s)
Absorption Intestinal absorption (human) Running Numeric (% Absorbed)
Absorption Skin Permeability Running Numeric (log Kp)
Absorption P-glycoprotein substrate Running Categorical (Yes/No)
Absorption P-glycoprotein I inhibitor Running Categorical (Yes/No)
Absorption P-glycoprotein II inhibitor Running Categorical (Yes/No)
Distribution VDss (human) Running Numeric (log L/kg)
Distribution Fraction unbound (human) Running Numeric (Fu)
Distribution BBB permeability Running Numeric (log BB)
Distribution CNS permeability Running Numeric (log PS)
Metabolism CYP2D6 substrate Running Categorical (Yes/No)
Metabolism CYP3A4 substrate Running Categorical (Yes/No)
Metabolism CYP1A2 inhibitior Running Categorical (Yes/No)
Metabolism CYP2C19 inhibitior Running Categorical (Yes/No)
Metabolism CYP2C9 inhibitior Running Categorical (Yes/No)
Metabolism CYP2D6 inhibitior Running Categorical (Yes/No)
Metabolism CYP3A4 inhibitior Running Categorical (Yes/No)
Excretion Total Clearance Running Numeric (log ml/min/kg)
Excretion Renal OCT2 substrate Running Categorical (Yes/No)
Toxicity AMES toxicity Running Categorical (Yes/No)
Toxicity Max. tolerated dose (human) Running Numeric (log mg/kg/day)
M. Mudassar Ali

Toxicity hERG I inhibitor Running Categorical (Yes/No)

Toxicity hERG II inhibitor Running Categorical (Yes/No)
Toxicity Oral Rat Acute Toxicity (LD50) Running Numeric (mol/kg)
Toxicity Oral Rat Chronic Toxicity (LOAEL) Running Numeric (log
mg/kg_bw/day)
Toxicity Hepatotoxicity Running Categorical (Yes/No)
Toxicity Skin Sensitisation Running Categorical (Yes/No)
Toxicity T.Pyriformis toxicity Running Numeric (log ug/L)
Toxicity Minnow toxicity Running Numeric (log mM)

Molinspiration:

PCR ligand 0.12

Ion channel modulator -0.04
Kinase inhibitor -0.07
Nuclear receptor ligand -0.19
Protease inhibitor -0.20
Enzyme inhibitor 0.28
M. Mudassar Ali

Rampage:

Evaluation of residues
Residue [A 7 :ASP] ( 70.85,-108.86) in Allowed region
Residue [A 9 :ASN] (-109.84, 52.05) in Allowed region
Residue [A 30 :LYS] ( -85.63, 45.78) in Allowed region
Residue [A 31 :ASN] ( -37.12, 126.12) in Allowed region
Residue [A 37 :ALA] (-114.52,-164.52) in Allowed region
Residue [A 49 :THR] ( -38.77, -33.67) in Allowed region
Residue [A 56 :GLN] (-178.26, 138.82) in Allowed region
Residue [A 61 :THR] (-142.91, 74.23) in Allowed region
Residue [A 66 :ALA] ( -48.59, 158.06) in Allowed region
Residue [A 74 :ASN] (-138.34, 55.98) in Allowed region
Residue [A 79 :ALA] (-162.74, 105.16) in Allowed region
Residue [A 88 :VAL] ( -75.69, -65.34) in Allowed region
Residue [A 90 :SER] (-148.79, 68.86) in Allowed region
Residue [A 93 :TYR] (-170.71, 116.64) in Allowed region
Residue [A 106 :TYR] ( -45.80, -26.63) in Allowed region
Residue [A 108 :ASP] ( -72.79, 81.92) in Allowed region
Residue [A 112 :TYR] ( 61.06, -70.85) in Allowed region
Residue [A 117 :THR] (-120.28,-125.59) in Allowed region
Residue [A 126 :TYR] ( 47.06,-102.30) in Allowed region
Residue [A 129 :SER] (-149.93,-150.06) in Allowed region
Residue [A 133 :GLY] ( 57.75, 78.13) in Allowed region
Residue [A 142 :PHE] ( 47.53, 81.59) in Allowed region
Residue [A 143 :PHE] ( 48.64, 20.61) in Allowed region
Residue [A 161 :ASP] ( -43.47, -81.58) in Allowed region
Residue [A 164 :SER] ( -66.89,-174.41) in Allowed region
Residue [A 166 :ASN] ( -67.70, 13.50) in Allowed region
Residue [A 182 :ASP] ( 45.24,-128.95) in Allowed region
Residue [A 197 :ASN] ( -60.48, 9.03) in Allowed region
Residue [A 198 :ASP] (-108.39, 62.01) in Allowed region
Residue [A 201 :ASP] ( -65.49, 15.03) in Allowed region
Residue [A 220 :ALA] ( 170.14, 169.42) in Allowed region
Residue [A 222 :ASN] ( 57.46, 4.77) in Allowed region
Residue [A 233 :ARG] ( -87.78, -92.42) in Allowed region
Residue [A 241 :THR] ( -48.30, -18.60) in Allowed region
Residue [A 244 :ASP] ( 44.83, 74.58) in Allowed region
Residue [A 250 :ASN] ( -35.96, -61.37) in Allowed region
Residue [A 265 :PHE] ( -69.75, 17.60) in Allowed region
Residue [A 279 :LYS] ( -97.68,-109.46) in Allowed region
Residue [A 283 :GLY] ( 73.51, -67.83) in Allowed region
Residue [A 287 :SER] (-164.91, 110.13) in Allowed region
Residue [A 302 :PHE] (-126.79, -77.05) in Allowed region
Residue [A 304 :LYS] ( -58.48, -9.13) in Allowed region
Residue [A 307 :ASN] ( 178.65, 153.33) in Allowed region
Residue [A 322 :TYR] (-110.78, -96.20) in Allowed region
Residue [A 323 :SER] ( 59.08,-120.06) in Allowed region
Residue [A 327 :VAL] (-154.79, -31.70) in Allowed region
Residue [B 3 :ILE] (-143.06,-132.33) in Allowed region
Residue [B 4 :TYR] ( -41.64, 117.22) in Allowed region
Residue [B 11 :LEU] (-163.13, 112.82) in Allowed region
Residue [B 12 :ASP] (-114.95, 81.03) in Allowed region
Residue [B 27 :GLY] ( 55.80,-101.98) in Allowed region
M. Mudassar Ali

Residue [B 31 :ASN] (-179.22, 115.50) in Allowed region

Residue [B 42 :LYS] (-130.14, 77.95) in Allowed region
Residue [B 48 :ASN] (-136.45,-143.89) in Allowed region
Residue [B 64 :ASP] ( -79.71, -76.29) in Allowed region
Residue [B 65 :ARG] ( -41.38, 153.96) in Allowed region
Residue [B 71 :GLN] ( -44.31, -70.66) in Allowed region
Residue [B 86 :ALA] ( -33.17, -62.44) in Allowed region
Residue [B 105 :SER] ( -36.74, -37.00) in Allowed region
Residue [B 108 :ASP] ( -73.14, 83.01) in Allowed region
Residue [B 109 :MET] (-143.31, -3.70) in Allowed region
Residue [B 112 :TYR] (-133.32, -56.47) in Allowed region
Residue [B 117 :THR] ( -79.83,-151.99) in Allowed region
Residue [B 119 :GLY] ( -90.34, 98.82) in Allowed region
Residue [B 121 :ALA] ( 65.99, -35.53) in Allowed region
Residue [B 123 :THR] ( -73.05, -66.47) in Allowed region
Residue [B 126 :TYR] (-128.48,-150.97) in Allowed region
Residue [B 129 :SER] (-139.94,-155.73) in Allowed region
Residue [B 140 :SER] ( -46.83, -64.30) in Allowed region
Residue [B 142 :PHE] ( -69.09, 59.98) in Allowed region
Residue [B 143 :PHE] ( 71.14, 38.13) in Allowed region
Residue [B 145 :LEU] (-110.85, -81.96) in Allowed region
Residue [B 146 :VAL] ( -72.88, 83.84) in Allowed region
Residue [B 148 :GLY] ( 130.81, -45.15) in Allowed region
Residue [B 158 :LYS] ( -56.18, 105.47) in Allowed region
Residue [B 160 :GLN] (-123.65,-138.75) in Allowed region
Residue [B 161 :ASP] ( 58.64,-107.03) in Allowed region
Residue [B 195 :ARG] ( -51.67, 172.50) in Allowed region
Residue [B 204 :GLY] ( -48.33, 99.92) in Allowed region
Residue [B 205 :ASN] ( 75.07, 33.61) in Allowed region
Residue [B 208 :ARG] (-113.84,-157.37) in Allowed region
Residue [B 221 :ASN] ( 41.87,-103.61) in Allowed region
Residue [B 233 :ARG] (-108.13, 50.46) in Allowed region
Residue [B 248 :MET] ( -58.20, 107.60) in Allowed region
Residue [B 278 :GLY] (-123.96, 90.28) in Allowed region
Residue [B 293 :TYR] ( 177.64, 162.74) in Allowed region
Residue [B 307 :ASN] ( 178.68, 142.74) in Allowed region
Residue [B 322 :TYR] (-114.59, -78.98) in Allowed region
Residue [B 323 :SER] ( 57.39, -53.63) in Allowed region
Residue [B 328 :GLY] ( -78.25,-111.76) in Allowed region
Residue [C 5 :ASN] (-145.28, -79.68) in Allowed region
Residue [C 10 :LYS] ( 61.63, 68.52) in Allowed region
Residue [C 23 :TRP] (-114.88,-162.00) in Allowed region
Residue [C 31 :ASN] (-175.85, 138.69) in Allowed region
Residue [C 35 :THR] ( -44.52, 147.76) in Allowed region
Residue [C 47 :ILE] ( -59.02, -68.30) in Allowed region
Residue [C 48 :ASN] (-130.21,-164.13) in Allowed region
Residue [C 70 :GLN] ( -83.10, 29.09) in Allowed region
Residue [C 87 :GLU] ( 76.02, -5.53) in Allowed region
Residue [C 102 :ASP] ( -44.72, -31.58) in Allowed region
Residue [C 109 :MET] (-139.19, -6.73) in Allowed region
Residue [C 113 :PHE] ( 75.31, 63.88) in Allowed region
Residue [C 119 :GLY] ( -81.34, 60.97) in Allowed region
Residue [C 123 :THR] ( -90.60, -86.60) in Allowed region
Residue [C 126 :TYR] ( -49.43, 99.77) in Allowed region
Residue [C 130 :ARG] ( -24.99, 116.74) in Allowed region
Residue [C 141 :ASP] (-152.43, 60.22) in Allowed region
Residue [C 145 :LEU] ( -88.94, -73.92) in Allowed region
M. Mudassar Ali

Residue [C 160 :GLN] (-141.32, -36.11) in Allowed region

Residue [C 166 :ASN] ( -75.21, 44.78) in Allowed region
Residue [C 174 :GLY] (-174.20, 110.65) in Allowed region
Residue [C 182 :ASP] ( 46.41,-132.04) in Allowed region
Residue [C 201 :ASP] (-151.81, 17.61) in Allowed region
Residue [C 206 :GLY] (-138.04, -93.91) in Allowed region
Residue [C 219 :ASP] (-130.58, 73.71) in Allowed region
Residue [C 244 :ASP] ( -74.49, 59.64) in Allowed region
Residue [C 266 :GLY] ( 101.95, 47.71) in Allowed region
Residue [C 280 :GLN] ( 63.72, 56.87) in Allowed region
Residue [C 290 :LEU] (-103.37, -67.10) in Allowed region
Residue [C 302 :PHE] ( -44.56, -29.07) in Allowed region
Residue [C 304 :LYS] ( -37.17, -27.78) in Allowed region
Residue [C 311 :ASP] (-171.23, 113.25) in Allowed region
Residue [C 319 :GLU] ( -39.61, 103.86) in Allowed region
Residue [C 321 :ASP] ( -48.49, 100.43) in Allowed region
Residue [C 324 :SER] ( -53.87, 107.67) in Allowed region
Residue [C 326 :TYR] ( -77.23, -66.55) in Allowed region
Residue [A 4 :TYR] ( 156.23, 63.37) in Outlier region
Residue [A 29 :SER] ( 86.48, 68.09) in Outlier region
Residue [A 38 :GLN] ( 169.71, 138.98) in Outlier region
Residue [A 87 :GLU] ( 50.08, -21.82) in Outlier region
Residue [A 148 :GLY] (-165.69, -26.99) in Outlier region
Residue [A 171 :ASP] ( -40.50, 94.69) in Outlier region
Residue [A 200 :GLN] ( -66.44, 17.90) in Outlier region
Residue [A 202 :ARG] ( 89.72,-118.29) in Outlier region
Residue [A 205 :ASN] ( -60.65, 81.98) in Outlier region
Residue [A 206 :GLY] ( 14.34, -96.82) in Outlier region
Residue [A 208 :ARG] ( 97.55, 116.37) in Outlier region
Residue [A 236 :SER] ( 174.88, 121.64) in Outlier region
Residue [A 249 :ALA] ( 54.05, 98.56) in Outlier region
Residue [A 266 :GLY] ( 120.38, -79.57) in Outlier region
Residue [A 267 :LEU] ( -39.05, 154.21) in Outlier region
Residue [A 280 :GLN] ( -56.74, 80.74) in Outlier region
Residue [A 285 :GLY] ( -39.99, 67.40) in Outlier region
Residue [A 319 :GLU] ( -30.61, 102.69) in Outlier region
Residue [A 324 :SER] ( 33.56, -59.19) in Outlier region
Residue [A 326 :TYR] ( 101.86, -62.17) in Outlier region
Residue [B 2 :GLU] ( 136.06, 132.89) in Outlier region
Residue [B 7 :ASP] ( 59.44, -80.72) in Outlier region
Residue [B 9 :ASN] ( 102.48,-172.90) in Outlier region
Residue [B 95 :ARG] ( -25.45, 109.85) in Outlier region
Residue [B 103 :VAL] ( 91.11, -64.87) in Outlier region
Residue [B 125 :ASN] ( -50.72, -84.61) in Outlier region
Residue [B 182 :ASP] ( 19.75, 49.15) in Outlier region
Residue [B 183 :GLY] ( 133.88, -79.15) in Outlier region
Residue [B 197 :ASN] ( -41.86, -6.49) in Outlier region
Residue [B 201 :ASP] ( -48.41, 71.42) in Outlier region
Residue [B 202 :ARG] ( 23.12, 103.47) in Outlier region
Residue [B 206 :GLY] ( -12.96, -45.40) in Outlier region
Residue [B 209 :ALA] ( 177.73, 108.20) in Outlier region
Residue [B 234 :ASN] ( 141.86, -28.78) in Outlier region
Residue [B 251 :LYS] ( -5.15, 106.83) in Outlier region
Residue [B 319 :GLU] ( -39.95, 77.28) in Outlier region
Residue [B 326 :TYR] ( 169.81, 25.52) in Outlier region
Residue [B 327 :VAL] ( 59.75, 124.88) in Outlier region
Residue [C 117 :THR] ( -73.66,-120.21) in Outlier region
M. Mudassar Ali

Residue [C 121 :ALA] ( 60.32, -77.85) in Outlier region

Residue [C 127 :MET] ( 19.98, 39.09) in Outlier region
Residue [C 165 :ILE] ( 8.48, -73.44) in Outlier region
Residue [C 167 :SER] (-164.10, -5.35) in Outlier region
Residue [C 200 :GLN] ( -48.72, 82.42) in Outlier region
Residue [C 207 :ASP] ( 30.35, -76.87) in Outlier region
Residue [C 221 :ASN] ( 2.51, -83.12) in Outlier region
Residue [C 234 :ASN] ( 169.36, -8.13) in Outlier region
Residue [C 278 :GLY] (-116.88, 81.10) in Outlier region
Residue [C 303 :ASN] ( 154.72, 154.28) in Outlier region
Residue [C 322 :TYR] ( 133.30, 47.10) in Outlier region
Residue [C 323 :SER] ( 21.78, 115.22) in Outlier region
Residue [C 336 :GLY] (-167.38, 90.47) in Outlier region
Number of residues in favoured region (~98.0% expected) : 826 ( 82.3%)
Number of residues in allowed region ( ~2.0% expected) : 126 ( 12.5%)
Number of residues in outlier region : 52 ( 5.2%)

ProSA: