ACCESSION: MSBNK-Eawag-EQ344602
RECORD_TITLE: Clarithromycin N-Oxide; LC-ESI-QFT; MS2; CE: 30; R=35000; [M+H]+
DATE: 2015.08.25
AUTHORS: Beck B, Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag
LICENSE: CC BY
COPYRIGHT: Copyright (C) 2015 Eawag, Duebendorf, Switzerland
COMMENT: CONFIDENCE standard compound
COMMENT: EAWAG_UCHEM_ID 3446
CH$NAME: Clarithromycin N-Oxide
CH$NAME: (2S,3R,4S,6R)-2-[[(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-14-ethyl-12,13-dihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-7-methoxy-3,5,7,9,11,13-hexamethyl-2,10-dioxo-oxacyclotetradec-6-yl]oxy]-3-hydroxy-N,N,6-trimethyloxan-4-amine oxide
CH$COMPOUND_CLASS: N/A; Environmental Standard
CH$FORMULA: C38H69NO14
CH$EXACT_MASS: 763.47181
CH$SMILES: [O-][N+](C)(C)[C@H]3C[C@@H](C)O[C@@H](O[C@@H]2[C@@H](C)[C@H](O[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1)[C@@H](C)C(=O)O[C@H](CC)[C@@](C)(O)[C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@]2(C)OC)[C@@H]3O
CH$IUPAC: InChI=1S/C38H69NO14/c1-15-26-38(10,45)31(42)21(4)28(40)19(2)17-37(9,48-14)33(53-35-29(41)25(39(11,12)46)16-20(3)49-35)22(5)30(23(6)34(44)51-26)52-27-18-36(8,47-13)32(43)24(7)50-27/h19-27,29-33,35,41-43,45H,15-18H2,1-14H3/t19-,20-,21+,22+,23-,24+,25+,26-,27+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1
CH$LINK: CAS
118074-07-0
CH$LINK: PUBCHEM
CID:11320230
CH$LINK: INCHIKEY
KDRPFIWYMNONLJ-KCBOHYOISA-N
CH$LINK: CHEMSPIDER
9495187
CH$LINK: COMPTOX
DTXSID30891488
AC$INSTRUMENT: Q Exactive Plus Orbitrap Thermo Scientific
AC$INSTRUMENT_TYPE: LC-ESI-QFT
AC$MASS_SPECTROMETRY: MS_TYPE MS2
AC$MASS_SPECTROMETRY: ION_MODE POSITIVE
AC$MASS_SPECTROMETRY: IONIZATION ESI
AC$MASS_SPECTROMETRY: FRAGMENTATION_MODE HCD
AC$MASS_SPECTROMETRY: COLLISION_ENERGY 30 (nominal)
AC$MASS_SPECTROMETRY: RESOLUTION 35000
AC$CHROMATOGRAPHY: COLUMN_NAME XBridge C18 3.5um, 2.1x50mm, Waters
AC$CHROMATOGRAPHY: FLOW_GRADIENT 90/10 at 0 min, 50/50 at 4 min, 5/95 at 17 min, 5/95 at 25 min, 90/10 at 25.1 min, 90/10 at 30 min
AC$CHROMATOGRAPHY: FLOW_RATE 200 ul/min
AC$CHROMATOGRAPHY: RETENTION_TIME 9.7 min
AC$CHROMATOGRAPHY: SOLVENT A water with 0.1% formic acid
AC$CHROMATOGRAPHY: SOLVENT B methanol with 0.1% formic acid
MS$FOCUSED_ION: BASE_PEAK 764.4783
MS$FOCUSED_ION: PRECURSOR_M/Z 764.4791
MS$FOCUSED_ION: PRECURSOR_TYPE [M+H]+
MS$DATA_PROCESSING: RECALIBRATE loess on assigned fragments and MS1
MS$DATA_PROCESSING: REANALYZE Peaks with additional N2/O included
MS$DATA_PROCESSING: WHOLE RMassBank 1.9.6
PK$SPLASH: splash10-05fr-1921001000-3c223d7390797df81a7f
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
55.0541 C4H7+ 1 55.0542 -1.94
57.0333 C3H5O+ 1 57.0335 -3.18
57.0698 C4H9+ 1 57.0699 -1.34
58.0651 C3H8N+ 1 58.0651 -0.44
59.0491 C3H7O+ 1 59.0491 -0.53
60.0443 C2H6NO+ 1 60.0444 -1.17
62.06 C2H8NO+ 1 62.06 -0.81
65.0385 C5H5+ 1 65.0386 -0.87
67.0542 C5H7+ 1 67.0542 -0.99
69.0333 C4H5O+ 1 69.0335 -2.48
69.0698 C5H9+ 1 69.0699 -1.11
70.0651 C4H8N+ 1 70.0651 -0.79
71.049 C4H7O+ 1 71.0491 -1.43
71.0728 C4H9N+ 1 71.073 -1.7
72.0443 C3H6NO+ 1 72.0444 -1.39
72.0807 C4H10N+ 1 72.0808 -1.05
73.0648 C4H9O+ 1 73.0648 -0.57
74.06 C3H8NO+ 1 74.06 -1.22
75.0439 C3H7O2+ 1 75.0441 -1.54
79.054 C6H7+ 1 79.0542 -2.49
81.0697 C6H9+ 1 81.0699 -1.69
83.0491 C5H7O+ 1 83.0491 -0.86
84.0807 C5H10N+ 1 84.0808 -0.31
85.0283 C4H5O2+ 1 85.0284 -0.89
85.0647 C5H9O+ 1 85.0648 -0.96
86.06 C4H8NO+ 1 86.06 -0.82
95.0491 C6H7O+ 1 95.0491 -0.43
95.0855 C7H11+ 1 95.0855 -0.6
97.0648 C6H9O+ 1 97.0648 -0.22
98.0965 C6H12N+ 1 98.0964 0.35
99.0678 C5H9NO+ 1 99.0679 -0.66
99.0803 C6H11O+ 1 99.0804 -1.53
99.1042 C6H13N+ 1 99.1043 -0.71
100.112 C6H14N+ 1 100.1121 -0.66
101.0233 C4H5O3+ 1 101.0233 -0.2
102.0913 C5H12NO+ 1 102.0913 -0.59
107.0854 C8H11+ 1 107.0855 -1
109.0648 C7H9O+ 1 109.0648 -0.2
109.1011 C8H13+ 1 109.1012 -0.34
111.0438 C6H7O2+ 1 111.0441 -1.94
111.0804 C7H11O+ 1 111.0804 -0.01
111.1169 C8H15+ 1 111.1168 0.57
112.1121 C7H14N+ 1 112.1121 0.22
113.0596 C6H9O2+ 1 113.0597 -0.76
114.0913 C6H12NO+ 1 114.0913 -0.27
115.0753 C6H11O2+ 1 115.0754 -0.75
116.0707 C5H10NO2+ 1 116.0706 0.47
116.1069 C6H14NO+ 1 116.107 -0.35
119.0853 C9H11+ 1 119.0855 -1.99
121.1012 C9H13+ 1 121.1012 -0.22
123.0803 C8H11O+ 1 123.0804 -0.82
125.0597 C7H9O2+ 1 125.0597 -0.37
125.096 C8H13O+ 1 125.0961 -0.41
126.0912 C7H12NO+ 1 126.0913 -1.19
127.0753 C7H11O2+ 1 127.0754 -0.68
127.1116 C8H15O+ 1 127.1117 -0.88
128.1069 C7H14NO+ 1 128.107 -0.78
129.0546 C6H9O3+ 1 129.0546 0.07
129.091 C7H13O2+ 1 129.091 -0.12
130.0862 C6H12NO2+ 1 130.0863 -0.58
132.0655 C5H10NO3+ 1 132.0655 -0.3
133.1011 C10H13+ 1 133.1012 -0.73
135.0803 C9H11O+ 1 135.0804 -0.97
135.1165 C10H15+ 1 135.1168 -2.27
137.096 C9H13O+ 1 137.0961 -0.38
139.0752 C8H11O2+ 1 139.0754 -1.12
139.1117 C9H15O+ 1 139.1117 -0.51
140.1069 C8H14NO+ 1 140.107 -0.43
141.0547 C7H9O3+ 1 141.0546 0.85
141.0908 C8H13O2+ 1 141.091 -1.67
143.0702 C7H11O3+ 1 143.0703 -0.49
143.1068 C8H15O2+ 1 143.1067 1.08
146.1175 C7H16NO2+ 1 146.1176 -0.58
147.0803 C10H11O+ 1 147.0804 -1.17
147.1168 C11H15+ 1 147.1168 -0.39
149.0961 C10H13O+ 1 149.0961 0.26
149.1324 C11H17+ 1 149.1325 -0.31
151.0751 C9H11O2+ 1 151.0754 -1.63
151.1117 C10H15O+ 1 151.1117 -0.01
151.1483 C11H19+ 1 151.1481 1.48
153.0909 C9H13O2+ 1 153.091 -0.37
155.1065 C9H15O2+ 1 155.1067 -1.01
156.1019 C8H14NO2+ 1 156.1019 -0.16
157.0858 C8H13O3+ 1 157.0859 -0.7
158.1175 C8H16NO2+ 1 158.1176 -0.35
159.1169 C12H15+ 1 159.1168 0.27
159.1252 C8H17NO2+ 1 159.1254 -0.94
161.1322 C12H17+ 1 161.1325 -1.59
163.0754 C10H11O2+ 1 163.0754 0.58
163.1117 C11H15O+ 1 163.1117 -0.32
165.0909 C10H13O2+ 1 165.091 -0.4
165.1274 C11H17O+ 1 165.1274 -0.19
167.1066 C10H15O2+ 1 167.1067 -0.34
167.143 C11H19O+ 1 167.143 -0.49
169.0858 C9H13O3+ 1 169.0859 -0.71
169.1222 C10H17O2+ 1 169.1223 -0.39
171.1015 C9H15O3+ 1 171.1016 -0.53
173.1326 C13H17+ 1 173.1325 0.71
174.1124 C8H16NO3+ 1 174.1125 -0.17
175.1116 C12H15O+ 1 175.1117 -0.98
177.1273 C12H17O+ 1 177.1274 -0.4
179.1065 C11H15O2+ 1 179.1067 -0.87
179.143 C12H19O+ 1 179.143 -0.4
181.0857 C10H13O3+ 1 181.0859 -1.16
181.1222 C11H17O2+ 1 181.1223 -0.64
183.1015 C10H15O3+ 1 183.1016 -0.22
183.1379 C11H19O2+ 1 183.138 -0.36
185.1171 C10H17O3+ 1 185.1172 -0.76
185.1325 C14H17+ 1 185.1325 0.12
187.148 C14H19+ 1 187.1481 -0.52
188.1283 C9H18NO3+ 1 188.1281 0.96
189.127 C13H17O+ 1 189.1274 -2.18
189.1636 C14H21+ 1 189.1638 -1.09
191.1066 C12H15O2+ 1 191.1067 -0.19
191.143 C13H19O+ 1 191.143 -0.11
192.1229 C8H18NO4+ 1 192.123 -0.75
193.1223 C12H17O2+ 1 193.1223 -0.14
195.1379 C12H19O2+ 1 195.138 -0.24
197.1172 C11H17O3+ 1 197.1172 0.1
199.0964 C10H15O4+ 1 199.0965 -0.68
199.1484 C15H19+ 1 199.1481 1.42
201.1637 C15H21+ 1 201.1638 -0.33
203.1065 C13H15O2+ 1 203.1067 -0.77
203.1433 C14H19O+ 1 203.143 1.17
205.1225 C13H17O2+ 1 205.1223 0.8
205.1587 C14H21O+ 1 205.1587 -0.15
207.1381 C13H19O2+ 1 207.138 0.69
207.1741 C14H23O+ 1 207.1743 -1.22
209.1171 C12H17O3+ 1 209.1172 -0.58
209.1534 C13H21O2+ 1 209.1536 -0.84
211.1328 C12H19O3+ 1 211.1329 -0.43
213.1485 C12H21O3+ 1 213.1485 0.04
215.143 C15H19O+ 1 215.143 -0.24
217.1589 C15H21O+ 1 217.1587 1.1
219.1382 C14H19O2+ 1 219.138 1.29
219.1747 C15H23O+ 1 219.1743 1.45
221.1172 C13H17O3+ 1 221.1172 -0.18
221.1535 C14H21O2+ 1 221.1536 -0.39
223.1331 C13H19O3+ 1 223.1329 1.03
223.1693 C14H23O2+ 1 223.1693 0.11
225.1642 C17H21+ 1 225.1638 1.74
227.1789 C17H23+ 1 227.1794 -2.19
229.1587 C16H21O+ 1 229.1587 -0.14
231.1381 C15H19O2+ 1 231.138 0.71
233.1535 C15H21O2+ 1 233.1536 -0.37
235.1335 C14H19O3+ 1 235.1329 2.59
235.1692 C15H23O2+ 1 235.1693 -0.2
239.1277 C13H19O4+ 1 239.1278 -0.4
243.1743 C17H23O+ 1 243.1743 -0.13
245.1899 C17H25O+ 1 245.19 -0.29
247.169 C16H23O2+ 1 247.1693 -0.96
249.1484 C15H21O3+ 1 249.1485 -0.57
251.1641 C15H23O3+ 1 251.1642 -0.44
253.1589 C18H21O+ 1 253.1587 0.94
259.133 C16H19O3+ 1 259.1329 0.38
261.1486 C16H21O3+ 1 261.1485 0.42
261.1848 C17H25O2+ 1 261.1849 -0.52
263.2005 C17H27O2+ 1 263.2006 -0.25
265.1799 C16H25O3+ 1 265.1798 0.26
267.1588 C15H23O4+ 1 267.1591 -1.03
271.1541 C14H23O5+ 1 271.154 0.44
271.1688 C18H23O2+ 1 271.1693 -1.61
277.1433 C16H21O4+ 1 277.1434 -0.42
279.159 C16H23O4+ 1 279.1591 -0.38
289.1797 C18H25O3+ 1 289.1798 -0.45
291.1952 C18H27O3+ 1 291.1955 -0.93
301.2166 C20H29O2+ 1 301.2162 1.34
303.2316 C20H31O2+ 1 303.2319 -0.85
307.1903 C18H27O4+ 1 307.1904 -0.34
311.2007 C21H27O2+ 1 311.2006 0.36
320.2067 C15H30NO6+ 1 320.2068 -0.11
325.201 C18H29O5+ 1 325.201 0.24
329.211 C21H29O3+ 1 329.2111 -0.34
335.1852 C19H27O5+ 1 335.1853 -0.27
339.2167 C19H31O5+ 1 339.2166 0.23
347.2217 C21H31O4+ 1 347.2217 -0.05
365.2323 C21H33O5+ 1 365.2323 0.05
379.248 C22H35O5+ 1 379.2479 0.37
383.2428 C21H35O6+ 1 383.2428 -0.12
393.2272 C22H33O6+ 1 393.2272 0.01
397.2585 C22H37O6+ 1 397.2585 0.06
411.2377 C22H35O7+ 1 411.2377 -0.12
425.2531 C23H37O7+ 1 425.2534 -0.75
556.3483 C29H50NO9+ 1 556.348 0.43
574.3586 C29H52NO10+ 2 574.3586 0.03
588.3744 C30H54NO10+ 2 588.3742 0.35
606.3848 C30H56NO11+ 1 606.3848 0.09
PK$NUM_PEAK: 190
PK$PEAK: m/z int. rel.int.
55.0541 728207.1 6
57.0333 1176383.4 10
57.0698 397524.5 3
58.0651 793221 6
59.0491 203140.1 1
60.0443 274070.5 2
62.06 1504824.1 12
65.0385 240896.3 2
67.0542 2529629.5 21
69.0333 636141.6 5
69.0698 3466751 29
70.0651 3477561.5 29
71.049 343462.1 2
71.0728 443835.4 3
72.0443 258244.2 2
72.0807 697932.8 5
73.0648 242481.6 2
74.06 235254.8 2
75.0439 235759.7 2
79.054 117844.4 1
81.0697 490030 4
83.0491 17006326 145
84.0807 2201420.2 18
85.0283 2065823.9 17
85.0647 2372634.5 20
86.06 2049264.8 17
95.0491 3681471.2 31
95.0855 770629.8 6
97.0648 13060347 111
98.0965 898617.9 7
99.0678 248824.4 2
99.0803 921032.6 7
99.1042 793063.5 6
100.112 4140545.2 35
101.0233 121281.6 1
102.0913 1457498.1 12
107.0854 793618.5 6
109.0648 4513018.5 38
109.1011 5504483.5 47
111.0438 623833.8 5
111.0804 876389.9 7
111.1169 544945.2 4
112.1121 213258.8 1
113.0596 51971644 444
114.0913 16155406 138
115.0753 2588193.2 22
116.0707 657192.3 5
116.1069 5324366.5 45
119.0853 694238.7 5
121.1012 15425703 131
123.0803 116893504 999
125.0597 994860.7 8
125.096 5425001.5 46
126.0912 340251.1 2
127.0753 3793857 32
127.1116 1839515.5 15
128.1069 12381024 105
129.0546 452356.7 3
129.091 320183.4 2
130.0862 220132.8 1
132.0655 706165.5 6
133.1011 318670.5 2
135.0803 572566.8 4
135.1165 845339.6 7
137.096 8919133 76
139.0752 703038.2 6
139.1117 2951589.2 25
140.1069 357656.8 3
141.0547 217855.3 1
141.0908 569893.6 4
143.0702 1786441.5 15
143.1068 182791 1
146.1175 3012326.5 25
147.0803 224663 1
147.1168 1084213.6 9
149.0961 310900.2 2
149.1324 4935977.5 42
151.0751 647023.8 5
151.1117 805536.4 6
151.1483 249684.1 2
153.0909 6201213.5 52
155.1065 2388719.5 20
156.1019 8310007.5 71
157.0858 1374110.1 11
158.1175 4567342 39
159.1169 1510645 12
159.1252 287556 2
161.1322 394013.6 3
163.0754 242725.4 2
163.1117 2717829 23
165.0909 4144949 35
165.1274 2730203.5 23
167.1066 696091.3 5
167.143 4266630 36
169.0858 1403832.5 11
169.1222 590133.4 5
171.1015 5524024.5 47
173.1326 332020.5 2
174.1124 25848458 220
175.1116 1453834.2 12
177.1273 10654963 91
179.1065 1096339.6 9
179.143 578960.3 4
181.0857 1417989.1 12
181.1222 3616276.5 30
183.1015 14093948 120
183.1379 1166359.8 9
185.1171 973141.8 8
185.1325 199879.1 1
187.148 1955437.4 16
188.1283 210748.4 1
189.127 344783.9 2
189.1636 676262.2 5
191.1066 315856.9 2
191.143 337725.5 2
192.1229 7306694.5 62
193.1223 11899563 101
195.1379 15850967 135
197.1172 1931752.5 16
199.0964 1300987 11
199.1484 262425.6 2
201.1637 590246.2 5
203.1065 881821.1 7
203.1433 621681.6 5
205.1225 425837 3
205.1587 5373049.5 45
207.1381 434197.9 3
207.1741 520306.3 4
209.1171 359913.8 3
209.1534 748538.5 6
211.1328 2561585.8 21
213.1485 1568259.1 13
215.143 1228097.4 10
217.1589 647232.9 5
219.1382 119455.1 1
219.1747 238318.6 2
221.1172 8226840.5 70
221.1535 2455032 20
223.1331 693615.6 5
223.1693 2363352.5 20
225.1642 118626.6 1
227.1789 389653.3 3
229.1587 768167.2 6
231.1381 1094266 9
233.1535 8604043 73
235.1335 252192.4 2
235.1692 949484.9 8
239.1277 6137866 52
243.1743 1016230.3 8
245.1899 5126225.5 43
247.169 704224.4 6
249.1484 1797098.1 15
251.1641 10510071 89
253.1589 442760.2 3
259.133 545430.5 4
261.1486 223403.3 1
261.1848 1181582.6 10
263.2005 7076443 60
265.1799 1222986.2 10
267.1588 623012.7 5
271.1541 323437.8 2
271.1688 2364464.2 20
277.1433 1350258.2 11
279.159 6069489 51
289.1797 19357440 165
291.1952 1763946.6 15
301.2166 495856.2 4
303.2316 487988.5 4
307.1903 20888978 178
311.2007 291927.1 2
320.2067 251165.6 2
321.206 2659823 22
325.201 1350095.8 11
329.211 2535034.5 21
335.1852 5915497.5 50
339.2167 541547.5 4
347.2217 11447831 97
353.1959 1971875.125 16
365.2323 19304502 164
379.248 5967088.5 50
383.2428 3670041.8 31
393.2272 9862391 84
397.2585 313743.3 2
411.2377 3207023.2 27
425.2531 555671 4
538.3374 1574236.875 13
556.3483 2161153.8 18
574.3586 9410035 80
588.3744 452462 3
606.3848 52430236 448
//
