ACCESSION: MSBNK-Eawag-EQ344606
RECORD_TITLE: Clarithromycin N-Oxide; LC-ESI-QFT; MS2; CE: 90; 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$MASS_SPECTROMETRY: COLLISION_ENERGY 90 (nominal)
AC$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$SPLASH: splash10-0aw9-9500000000-3021e1630fed2761f8df
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
53.9975 C2NO+ 1 53.9974 0.74
55.0179 C3H3O+ 1 55.0178 0.16
55.0543 C4H7+ 1 55.0542 0.42
56.0495 C3H6N+ 1 56.0495 -0.1
57.0335 C3H5O+ 1 57.0335 0.15
57.0573 C3H7N+ 1 57.0573 -0.01
57.0699 C4H9+ 1 57.0699 0.06
58.0651 C3H8N+ 1 58.0651 0.25
59.0491 C3H7O+ 1 59.0491 -0.02
60.0444 C2H6NO+ 1 60.0444 -0.5
61.0284 C2H5O2+ 1 61.0284 -0.26
62.06 C2H8NO+ 1 62.06 -0.17
65.0386 C5H5+ 1 65.0386 0.21
66.0463 C5H6+ 1 66.0464 -0.93
67.0542 C5H7+ 1 67.0542 -0.1
67.9892 C3O2+ 1 67.9893 -0.6
68.0494 C4H6N+ 1 68.0495 -0.38
69.0335 C4H5O+ 1 69.0335 -0.16
69.0699 C5H9+ 1 69.0699 -0.24
70.0651 C4H8N+ 1 70.0651 -0.22
71.0127 C3H3O2+ 1 71.0128 -0.08
71.0491 C4H7O+ 1 71.0491 -0.16
71.0729 C4H9N+ 1 71.073 -0.15
72.0444 C3H6NO+ 1 72.0444 -0.28
72.0808 C4H10N+ 1 72.0808 -0.22
73.0284 C3H5O2+ 1 73.0284 0.06
73.0521 C3H7NO+ 1 73.0522 -1.17
73.0648 C4H9O+ 1 73.0648 -0.16
74.0362 C3H6O2+ 1 74.0362 -0.42
74.06 C3H8NO+ 1 74.06 -0.81
75.0439 C3H7O2+ 1 75.0441 -1.41
77.0385 C6H5+ 1 77.0386 -1.25
78.0086 C3N3+ 1 78.0087 -0.68
78.0464 C6H6+ 1 78.0464 0.49
79.0542 C6H7+ 1 79.0542 -0.21
80.062 C6H8+ 1 80.0621 -0.27
81.0699 C6H9+ 1 81.0699 0.29
82.0651 C5H8N+ 1 82.0651 -0.68
83.0127 C4H3O2+ 1 83.0128 -0.31
83.0491 C5H7O+ 1 83.0491 -0.38
84.0808 C5H10N+ 1 84.0808 0.05
85.0284 C4H5O2+ 1 85.0284 -0.07
85.0648 C5H9O+ 1 85.0648 -0.13
86.06 C4H8NO+ 1 86.06 -0.24
87.0441 C4H7O2+ 1 87.0441 0.05
87.0678 C4H9NO+ 1 87.0679 -0.52
87.0803 C5H11O+ 1 87.0804 -1.62
88.0757 C4H10NO+ 1 88.0757 0.22
91.0543 C7H7+ 1 91.0542 0.37
92.062 C7H8+ 1 92.0621 -0.24
93.0699 C7H9+ 1 93.0699 0.57
94.0653 C6H8N+ 1 94.0651 1.32
94.0778 C7H10+ 1 94.0777 1.15
95.0492 C6H7O+ 1 95.0491 0.2
95.0855 C7H11+ 1 95.0855 0.24
96.057 C6H8O+ 1 96.057 0.14
96.0808 C6H10N+ 1 96.0808 0.46
97.0285 C5H5O2+ 1 97.0284 0.46
97.0648 C6H9O+ 1 97.0648 0.5
98.0601 C5H8NO+ 1 98.06 0.4
98.0964 C6H12N+ 1 98.0964 0.14
99.0806 C6H11O+ 1 99.0804 1.3
100.0756 C5H10NO+ 1 100.0757 -0.7
100.112 C6H14N+ 1 100.1121 -0.26
101.0234 C4H5O3+ 1 101.0233 0.39
101.0597 C5H9O2+ 1 101.0597 -0.45
102.0914 C5H12NO+ 1 102.0913 0.68
103.0542 C8H7+ 1 103.0542 0.13
104.0621 C8H8+ 1 104.0621 0.66
105.0448 C6H5N2+ 1 105.0447 0.62
105.0699 C8H9+ 1 105.0699 0.32
106.0777 C8H10+ 1 106.0777 -0.02
107.0492 C7H7O+ 1 107.0491 0.36
107.0855 C8H11+ 1 107.0855 0.12
108.0569 C7H8O+ 1 108.057 -0.52
108.0933 C8H12+ 1 108.0934 -0.29
109.0648 C7H9O+ 1 109.0648 0.35
109.1012 C8H13+ 1 109.1012 0.3
110.0725 C7H10O+ 1 110.0726 -0.69
111.044 C6H7O2+ 1 111.0441 -0.41
111.0805 C7H11O+ 1 111.0804 0.26
113.0597 C6H9O2+ 1 113.0597 -0.05
113.0961 C7H13O+ 1 113.0961 -0.19
114.0914 C6H12NO+ 1 114.0913 0.08
115.0542 C9H7+ 1 115.0542 0.12
116.0621 C9H8+ 1 116.0621 0.16
116.0705 C5H10NO2+ 1 116.0706 -0.47
117.0699 C9H9+ 1 117.0699 0.2
118.0777 C9H10+ 1 118.0777 -0.1
119.0604 C7H7N2+ 1 119.0604 0.46
119.0856 C9H11+ 1 119.0855 0.36
120.0934 C9H12+ 1 120.0934 0.32
121.0648 C8H9O+ 1 121.0648 -0.01
121.1012 C9H13+ 1 121.1012 0.19
122.0727 C8H10O+ 1 122.0726 0.52
123.0804 C8H11O+ 1 123.0804 -0.09
124.0884 C8H12O+ 1 124.0883 0.67
125.0597 C7H9O2+ 1 125.0597 -0.21
125.0962 C8H13O+ 1 125.0961 0.63
127.0753 C7H11O2+ 1 127.0754 -0.52
128.062 C10H8+ 1 128.0621 -0.17
128.1071 C7H14NO+ 1 128.107 1.01
129.0698 C10H9+ 1 129.0699 -0.28
130.0778 C10H10+ 1 130.0777 0.91
131.0855 C10H11+ 1 131.0855 0.02
132.0654 C5H10NO3+ 1 132.0655 -0.91
132.0934 C10H12+ 1 132.0934 0.59
133.0651 C9H9O+ 1 133.0648 1.94
133.076 C8H9N2+ 1 133.076 -0.56
133.1012 C10H13+ 1 133.1012 0.02
134.1091 C10H14+ 1 134.109 1.1
135.0804 C9H11O+ 1 135.0804 -0.38
135.1167 C10H15+ 1 135.1168 -1.16
136.0884 C9H12O+ 1 136.0883 0.98
137.0961 C9H13O+ 1 137.0961 -0.01
138.0676 C8H10O2+ 1 138.0675 0.64
139.0754 C8H11O2+ 1 139.0754 0.68
139.1119 C9H15O+ 1 139.1117 0.78
140.1071 C8H14NO+ 1 140.107 1.14
141.0699 C11H9+ 1 141.0699 0.02
142.0777 C11H10+ 1 142.0777 0.13
143.0856 C11H11+ 1 143.0855 0.72
144.0934 C11H12+ 1 144.0934 0.2
145.0648 C10H9O+ 1 145.0648 -0.28
145.1013 C11H13+ 1 145.1012 0.92
146.0728 C10H10O+ 1 146.0726 0.91
147.0805 C10H11O+ 1 147.0804 0.13
147.1168 C11H15+ 1 147.1168 -0.18
148.0882 C10H12O+ 1 148.0883 -0.52
149.0962 C10H13O+ 1 149.0961 0.8
149.1326 C11H17+ 1 149.1325 0.89
150.1041 C10H14O+ 1 150.1039 1.49
151.0754 C9H11O2+ 1 151.0754 0.29
151.1116 C10H15O+ 1 151.1117 -0.67
152.0831 C9H12O2+ 1 152.0832 -0.4
153.0703 C12H9+ 1 153.0699 2.5
153.0908 C9H13O2+ 1 153.091 -1.41
155.0603 C10H7N2+ 1 155.0604 -0.61
155.0855 C12H11+ 1 155.0855 -0.17
156.0934 C12H12+ 1 156.0934 0.24
157.1012 C12H13+ 1 157.1012 -0.11
158.1089 C12H14+ 1 158.109 -0.58
159.0803 C11H11O+ 1 159.0804 -0.76
159.117 C12H15+ 1 159.1168 1.03
160.0881 C11H12O+ 1 160.0883 -1.1
161.0962 C11H13O+ 1 161.0961 0.61
162.104 C11H14O+ 1 162.1039 0.76
163.0755 C10H11O2+ 1 163.0754 0.76
163.1116 C11H15O+ 1 163.1117 -0.56
164.1196 C11H16O+ 1 164.1196 0.45
165.0699 C13H9+ 1 165.0699 0.2
165.091 C10H13O2+ 1 165.091 0.21
165.1273 C11H17O+ 1 165.1274 -0.74
167.0856 C13H11+ 1 167.0855 0.44
168.0936 C13H12+ 1 168.0934 1.36
169.1012 C13H13+ 1 169.1012 0.26
170.109 C13H14+ 1 170.109 0.17
171.0799 C12H11O+ 1 171.0804 -2.87
171.1166 C13H15+ 1 171.1168 -1.21
172.0881 C12H12O+ 1 172.0883 -0.73
172.1249 C13H16+ 1 172.1247 1.38
173.0961 C12H13O+ 1 173.0961 -0.07
173.132 C13H17+ 1 173.1325 -2.81
175.1119 C12H15O+ 1 175.1117 0.85
177.1274 C12H17O+ 1 177.1274 -0.12
179.1073 C11H15O2+ 1 179.1067 3.71
181.1013 C14H13+ 1 181.1012 0.57
182.1088 C14H14+ 1 182.109 -1.16
183.1164 C14H15+ 1 183.1168 -2.28
185.0959 C13H13O+ 1 185.0961 -1.03
185.1321 C14H17+ 1 185.1325 -2.2
186.1038 C13H14O+ 1 186.1039 -0.68
187.1116 C13H15O+ 1 187.1117 -0.54
189.0904 C12H13O2+ 1 189.091 -3.21
195.1168 C15H15+ 1 195.1168 -0.19
197.133 C15H17+ 1 197.1325 2.65
200.1194 C14H16O+ 1 200.1196 -1.03
PK$NUM_PEAK: 177
PK$PEAK: m/z int. rel.int.
53.9975 291861 7
55.0179 1467007.8 36
55.0543 21247176 522
56.0495 1291766 31
57.0335 4882640.5 120
57.0573 314732.8 7
57.0699 2210751 54
58.0651 3519745.8 86
59.0491 1197936.8 29
60.0444 538244.2 13
61.0284 155031.4 3
62.06 973610.9 23
65.0386 4171183.5 102
66.0463 94871 2
67.0542 30393350 747
67.9892 163393.6 4
68.0494 318349 7
69.0335 3814888 93
69.0699 10287906 253
70.0651 4630280.5 113
71.0127 251506.1 6
71.0491 1494774.2 36
71.0729 1174003.4 28
72.0444 1616265 39
72.0808 2466042.8 60
73.0284 163010 4
73.0521 370302.7 9
73.0648 858566.9 21
74.0362 47087.5 1
74.06 356050.9 8
75.0439 76915.8 1
77.0385 842445.5 20
78.0086 73020.5 1
78.0464 97334.3 2
79.0542 12931330 318
80.062 406365.9 9
81.0699 11623323 285
82.0651 524675.8 12
83.0127 1765717.8 43
83.0491 30389562 747
84.0808 6421873 157
85.0284 2500778.2 61
85.0648 1539122 37
86.06 1479632 36
87.0441 161701.2 3
87.0678 355712.7 8
87.0803 48374.7 1
88.0757 1216671.6 29
91.0543 10988509 270
92.062 163646.8 4
93.0699 7119666.5 175
94.0653 98693.7 2
94.0778 286649.8 7
95.0492 6624450.5 162
95.0855 8813226 216
96.057 51309.1 1
96.0808 65442.7 1
97.0285 242587.8 5
97.0648 2975567 73
98.0601 408011.6 10
98.0964 2176496.5 53
99.0806 230533.7 5
100.0756 253359.8 6
100.112 1277323 31
101.0234 55779.8 1
101.0597 422448.2 10
102.0914 91639.8 2
103.0542 2543589 62
104.0621 242754.7 5
105.0448 1347608.5 33
105.0699 14742013 362
106.0777 720621.9 17
107.0492 875582.2 21
107.0855 4403383.5 108
108.0569 1223789 30
108.0933 76260.2 1
109.0648 9387555 230
109.1012 4789291.5 117
110.0725 81742.9 2
111.044 403043.7 9
111.0805 849318.4 20
113.0597 934039.5 22
113.0961 88818.9 2
114.0914 354951 8
115.0542 658922.6 16
116.0621 375472.6 9
116.0705 53932.5 1
117.0699 1665948.1 40
118.0777 186583 4
119.0604 511797.7 12
119.0856 8747978 215
120.0934 224650.9 5
121.0648 950326.5 23
121.1012 6065025 149
122.0727 1097124.9 26
123.0804 40617468 999
124.0884 198550.6 4
125.0597 531072.4 13
125.0962 842525.5 20
127.0753 207659.3 5
128.062 676059 16
128.1071 82606.8 2
129.0698 1311457 32
130.0778 614101.9 15
131.0855 1246077.1 30
132.0654 70021.9 1
132.0934 90477.8 2
133.0651 289823 7
133.076 822722.8 20
133.1012 1438631.5 35
134.1091 85041.6 2
135.0804 1258364.9 30
135.1167 419781.7 10
136.0884 694136.6 17
137.0961 3117632.8 76
138.0676 90933 2
139.0754 157879.5 3
139.1119 70526.7 1
140.1071 251256.9 6
141.0699 485912.3 11
142.0777 1137162.4 27
143.0856 1012519.1 24
144.0934 728738.7 17
145.0648 411465.1 10
145.1013 1101646.2 27
146.0728 140707.6 3
147.0805 533400.1 13
147.1168 907582.2 22
148.0882 76240.7 1
149.0962 665352 16
149.1326 182639.5 4
150.1041 64050.4 1
151.0754 246344.4 6
151.1116 293366 7
152.0831 155019 3
153.0703 72567 1
153.0908 55642.1 1
155.0603 49254 1
155.0855 406536.3 9
156.0934 451673.8 11
157.1012 1131844.6 27
158.1089 418880.9 10
159.0803 291165.6 7
159.117 438642.6 10
160.0881 298110.8 7
161.0962 620107.3 15
162.104 56124.7 1
163.0755 82810.2 2
163.1116 855344.2 21
164.1196 57680.7 1
165.0699 91705.9 2
165.091 71816.9 1
165.1273 71393.3 1
167.0856 93900.7 2
168.0936 48204 1
169.1012 224104 5
170.109 176870.4 4
171.0799 52620.1 1
171.1166 295113.6 7
172.0881 88519.7 2
172.1249 187620.7 4
173.0961 237833.1 5
173.132 78085.8 1
175.1119 447736.8 11
177.1274 294025.8 7
179.1073 49054.6 1
181.1013 158165.4 3
182.1088 45821.8 1
183.1164 140240.2 3
185.0959 76193.9 1
185.1321 54204.8 1
186.1038 51055.2 1
187.1116 84638 2
189.0904 57137.7 1
195.1168 180830.6 4
197.133 47581.3 1
200.1194 54987.7 1
//
