ACCESSION: MSBNK-Eawag-EQ344604
RECORD_TITLE: Clarithromycin N-Oxide; LC-ESI-QFT; MS2; CE: 60; 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$MASS_SPECTROMETRY: COLLISION_ENERGY 60 (nominal)
AC$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$SPLASH: splash10-00di-5900000000-4bcee5a5a90f7fedd473
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
55.0178 C3H3O+ 1 55.0178 -0.75
55.0542 C4H7+ 1 55.0542 -0.12
56.0495 C3H6N+ 1 56.0495 0.26
57.0335 C3H5O+ 1 57.0335 -0.2
57.0699 C4H9+ 1 57.0699 -0.12
58.0651 C3H8N+ 1 58.0651 -0.1
59.0491 C3H7O+ 1 59.0491 -0.36
60.0444 C2H6NO+ 1 60.0444 -0.34
62.06 C2H8NO+ 1 62.06 -0.33
65.0386 C5H5+ 1 65.0386 -0.25
67.0542 C5H7+ 1 67.0542 -0.1
67.9893 C3O2+ 1 67.9893 -0.3
68.0494 C4H6N+ 1 68.0495 -0.38
69.0335 C4H5O+ 1 69.0335 -0.31
69.0699 C5H9+ 1 69.0699 -0.24
70.0651 C4H8N+ 1 70.0651 -0.37
71.0491 C4H7O+ 1 71.0491 -0.58
71.073 C4H9N+ 1 71.073 -0.01
71.0855 C5H11+ 1 71.0855 -0.24
72.0443 C3H6NO+ 1 72.0444 -0.56
72.0807 C4H10N+ 1 72.0808 -0.63
73.0284 C3H5O2+ 1 73.0284 -0.22
73.0522 C3H7NO+ 1 73.0522 0.2
73.0647 C4H9O+ 1 73.0648 -0.84
74.06 C3H8NO+ 1 74.06 -0.95
77.0383 C6H5+ 1 77.0386 -3.07
79.0542 C6H7+ 1 79.0542 -0.59
81.0699 C6H9+ 1 81.0699 0.04
82.0652 C5H8N+ 1 82.0651 0.3
83.0491 C5H7O+ 1 83.0491 -0.5
84.0808 C5H10N+ 1 84.0808 -0.07
85.0284 C4H5O2+ 1 85.0284 -0.3
85.0648 C5H9O+ 1 85.0648 -0.25
86.06 C4H8NO+ 1 86.06 -0.58
87.0441 C4H7O2+ 1 87.0441 0.05
87.0679 C4H9NO+ 1 87.0679 -0.06
87.0805 C5H11O+ 1 87.0804 0.33
88.0757 C4H10NO+ 1 88.0757 0
91.0542 C7H7+ 1 91.0542 -0.07
93.0699 C7H9+ 1 93.0699 0.25
95.0491 C6H7O+ 1 95.0491 0.09
95.0855 C7H11+ 1 95.0855 -0.07
97.0284 C5H5O2+ 1 97.0284 -0.16
97.0648 C6H9O+ 1 97.0648 0.19
98.0601 C5H8NO+ 1 98.06 0.81
98.0964 C6H12N+ 1 98.0964 0.04
99.0441 C5H7O2+ 1 99.0441 0.45
99.0804 C6H11O+ 1 99.0804 -0.22
99.1041 C6H13N+ 1 99.1043 -1.12
100.0757 C5H10NO+ 1 100.0757 0.5
100.112 C6H14N+ 1 100.1121 -0.36
101.0234 C4H5O3+ 1 101.0233 0.59
101.0597 C5H9O2+ 1 101.0597 0.14
102.0913 C5H12NO+ 1 102.0913 -0.79
103.0542 C8H7+ 1 103.0542 -0.65
105.0699 C8H9+ 1 105.0699 0.13
106.0777 C8H10+ 1 106.0777 -0.3
107.0855 C8H11+ 1 107.0855 -0.06
108.0569 C7H8O+ 1 108.057 -0.34
109.0648 C7H9O+ 1 109.0648 0.26
109.1012 C8H13+ 1 109.1012 0.12
110.0964 C7H12N+ 1 110.0964 -0.33
111.044 C6H7O2+ 1 111.0441 -0.05
111.0804 C7H11O+ 1 111.0804 -0.19
111.1169 C8H15+ 1 111.1168 0.3
113.0597 C6H9O2+ 1 113.0597 -0.32
113.0961 C7H13O+ 1 113.0961 -0.28
114.0914 C6H12NO+ 1 114.0913 0.35
115.0754 C6H11O2+ 1 115.0754 -0.05
116.0706 C5H10NO2+ 1 116.0706 0.13
116.1069 C6H14NO+ 1 116.107 -0.35
117.0698 C9H9+ 1 117.0699 -1
119.0856 C9H11+ 1 119.0855 0.28
121.1012 C9H13+ 1 121.1012 0.19
122.0727 C8H10O+ 1 122.0726 0.77
123.0804 C8H11O+ 1 123.0804 -0.42
124.0883 C8H12O+ 1 124.0883 -0.13
125.0597 C7H9O2+ 1 125.0597 0.03
125.0961 C8H13O+ 1 125.0961 -0.09
126.0913 C7H12NO+ 1 126.0913 -0.72
127.0753 C7H11O2+ 1 127.0754 -0.2
127.1117 C8H15O+ 1 127.1117 -0.09
128.107 C7H14NO+ 1 128.107 -0.32
129.0547 C6H9O3+ 1 129.0546 0.54
129.0698 C10H9+ 1 129.0699 -0.59
129.091 C7H13O2+ 1 129.091 0.26
129.1147 C7H15NO+ 1 129.1148 -0.97
131.0855 C10H11+ 1 131.0855 0.1
132.0655 C5H10NO3+ 1 132.0655 0
133.0759 C8H9N2+ 1 133.076 -0.94
133.1011 C10H13+ 1 133.1012 -0.2
135.0804 C9H11O+ 1 135.0804 -0.38
135.1167 C10H15+ 1 135.1168 -0.57
136.0883 C9H12O+ 1 136.0883 0.39
137.0961 C9H13O+ 1 137.0961 0.14
139.0753 C8H11O2+ 1 139.0754 -0.26
139.1117 C9H15O+ 1 139.1117 -0.15
140.107 C8H14NO+ 1 140.107 0.07
141.0545 C7H9O3+ 1 141.0546 -1.07
141.091 C8H13O2+ 1 141.091 -0.04
142.0777 C11H10+ 1 142.0777 -0.29
143.0703 C7H11O3+ 1 143.0703 -0.07
143.0857 C11H11+ 1 143.0855 1.21
144.0934 C11H12+ 1 144.0934 0.68
145.1011 C11H13+ 1 145.1012 -0.18
147.0804 C10H11O+ 1 147.0804 -0.08
147.1168 C11H15+ 1 147.1168 -0.05
149.0961 C10H13O+ 1 149.0961 0.12
149.1325 C11H17+ 1 149.1325 0.22
150.1041 C10H14O+ 1 150.1039 1.29
151.0754 C9H11O2+ 1 151.0754 0.03
151.1118 C10H15O+ 1 151.1117 0.12
152.0831 C9H12O2+ 1 152.0832 -0.53
153.091 C9H13O2+ 1 153.091 0.03
153.1274 C10H17O+ 1 153.1274 0.05
155.1066 C9H15O2+ 1 155.1067 -0.36
156.0933 C12H12+ 1 156.0934 -0.52
156.102 C8H14NO2+ 1 156.1019 0.8
157.1012 C12H13+ 1 157.1012 -0.11
158.1091 C12H14+ 1 158.109 0.68
158.1174 C8H16NO2+ 1 158.1176 -0.73
159.1168 C12H15+ 1 159.1168 0.08
160.0881 C11H12O+ 1 160.0883 -0.79
161.0961 C11H13O+ 1 161.0961 -0.13
161.1324 C12H17+ 1 161.1325 -0.35
163.0753 C10H11O2+ 1 163.0754 -0.65
163.1117 C11H15O+ 1 163.1117 -0.13
163.1481 C12H19+ 1 163.1481 -0.23
164.1196 C11H16O+ 1 164.1196 0.08
165.091 C10H13O2+ 1 165.091 0.21
165.1274 C11H17O+ 1 165.1274 0.29
167.1069 C10H15O2+ 1 167.1067 1.22
167.1427 C11H19O+ 1 167.143 -1.92
169.0858 C9H13O3+ 1 169.0859 -0.6
169.1012 C13H13+ 1 169.1012 0.31
170.1092 C13H14+ 1 170.109 0.99
171.1015 C9H15O3+ 1 171.1016 -0.53
171.1167 C13H15+ 1 171.1168 -0.51
172.1247 C13H16+ 1 172.1247 0.34
173.096 C12H13O+ 1 173.0961 -0.41
173.1326 C13H17+ 1 173.1325 0.77
174.1042 C12H14O+ 1 174.1039 1.46
174.1124 C8H16NO3+ 1 174.1125 -0.17
175.1118 C12H15O+ 1 175.1117 0.11
175.148 C13H19+ 1 175.1481 -0.73
176.1194 C12H16O+ 1 176.1196 -0.83
177.1274 C12H17O+ 1 177.1274 -0.01
179.1068 C11H15O2+ 1 179.1067 0.58
179.1428 C12H19O+ 1 179.143 -1.52
181.0858 C10H13O3+ 1 181.0859 -0.5
181.1222 C11H17O2+ 1 181.1223 -0.75
183.1017 C10H15O3+ 1 183.1016 0.82
183.1166 C14H15+ 1 183.1168 -1.46
185.1324 C14H17+ 1 185.1325 -0.63
187.1119 C13H15O+ 1 187.1117 0.85
187.1481 C14H19+ 1 187.1481 -0.41
188.1197 C13H16O+ 1 188.1196 0.92
189.1273 C13H17O+ 1 189.1274 -0.59
191.1068 C12H15O2+ 1 191.1067 0.65
191.1428 C13H19O+ 1 191.143 -1.26
193.1224 C12H17O2+ 1 193.1223 0.33
195.1379 C12H19O2+ 1 195.138 -0.39
197.1325 C15H17+ 1 197.1325 -0.14
199.1484 C15H19+ 1 199.1481 1.22
200.1194 C14H16O+ 1 200.1196 -0.73
201.1275 C14H17O+ 1 201.1274 0.39
201.1638 C15H21+ 1 201.1638 0.26
203.1065 C13H15O2+ 1 203.1067 -0.67
203.1429 C14H19O+ 1 203.143 -0.8
205.159 C14H21O+ 1 205.1587 1.26
210.1404 C16H18+ 1 210.1403 0.42
211.1328 C12H19O3+ 1 211.1329 -0.15
213.1273 C15H17O+ 1 213.1274 -0.34
215.1431 C15H19O+ 1 215.143 0.27
221.1169 C13H17O3+ 1 221.1172 -1.63
221.1537 C14H21O2+ 1 221.1536 0.47
225.1636 C17H21+ 1 225.1638 -0.61
229.1587 C16H21O+ 1 229.1587 -0.14
231.1379 C15H19O2+ 1 231.138 -0.16
233.1531 C15H21O2+ 1 233.1536 -2.17
249.1485 C15H21O3+ 1 249.1485 -0.24
251.164 C15H23O3+ 1 251.1642 -0.52
PK$NUM_PEAK: 182
PK$PEAK: m/z int. rel.int.
55.0178 621690.2 6
55.0542 7318075 71
56.0495 757016.1 7
57.0335 6237827.5 60
57.0699 3527694.8 34
58.0651 2453922.8 23
59.0491 1192218.8 11
60.0444 867436.1 8
62.06 1532104 14
65.0386 1734820 16
67.0542 19257250 186
67.9893 176585.4 1
68.0494 276958 2
69.0335 4792645.5 46
69.0699 17135278 166
70.0651 6454297 62
71.0491 1677030.9 16
71.073 855728.4 8
71.0855 329835.5 3
72.0443 1381398.9 13
72.0807 2603291.2 25
73.0284 256584.5 2
73.0522 222510.2 2
73.0647 1110075 10
74.06 357553.5 3
77.0383 427299.7 4
79.0542 3656002.2 35
81.0699 7725828.5 74
82.0652 579511.9 5
83.0491 38546948 374
84.0808 6610224 64
85.0284 3819770.2 37
85.0648 4233889.5 41
86.06 2966897 28
87.0441 683750.3 6
87.0679 384179.9 3
87.0805 297437.3 2
88.0757 2154284 20
91.0542 2869307.2 27
93.0699 4943836.5 47
95.0491 10023242 97
95.0855 9091651 88
97.0284 738684.6 7
97.0648 12463696 120
98.0601 250427 2
98.0964 2918769.5 28
99.0441 232832.3 2
99.0804 1271237.1 12
99.1041 222523.4 2
100.0757 360595.7 3
100.112 3027344.2 29
101.0234 387892 3
101.0597 609367.9 5
102.0913 564822.2 5
103.0542 355135.6 3
105.0699 5696873.5 55
106.0777 263325.9 2
107.0855 8159019 79
108.0569 198736.9 1
109.0648 15039008 145
109.1012 15201299 147
110.0964 203357.6 1
111.044 1823656.1 17
111.0804 2469499.8 23
111.1169 284852.2 2
113.0597 12071393 117
113.0961 1389740.5 13
114.0914 2292654.8 22
115.0754 824380.6 8
116.0706 738996 7
116.1069 583586.1 5
117.0698 680683.9 6
119.0856 9087183 88
121.1012 25685322 249
122.0727 388077.5 3
123.0804 102909552 999
124.0883 206721 2
125.0597 1865465.4 18
125.0961 7446957.5 72
126.0913 192226.9 1
127.0753 2029052.9 19
127.1117 837345.4 8
128.107 2706767.8 26
129.0547 183472 1
129.0698 314703.8 3
129.091 189639.4 1
129.1147 306614.8 2
131.0855 1363185.4 13
132.0655 2883815.2 27
133.0759 559904.6 5
133.1011 2556208.5 24
135.0804 2093572.6 20
135.1167 2498151 24
136.0883 458119.6 4
137.0961 19360750 187
139.0753 1096234.4 10
139.1117 1504596.2 14
140.107 517119.5 5
141.0545 350564.6 3
141.091 358804.6 3
142.0777 345345.8 3
143.0703 267144.2 2
143.0857 381168.9 3
144.0934 687659.3 6
145.1011 2095775.1 20
147.0804 1494081.4 14
147.1168 5141741.5 49
149.0961 1541494.8 14
149.1325 3609348.5 35
150.1041 110444.2 1
151.0754 3902267.8 37
151.1118 2934297.8 28
152.0831 177304 1
153.091 2019364.8 19
153.1274 322876.4 3
155.1066 629542.4 6
156.0933 259562.8 2
156.102 379174.9 3
157.1012 1674477.2 16
158.1091 432040.2 4
158.1174 223496.2 2
159.1168 4078344 39
160.0881 316497.5 3
161.0961 887199.9 8
161.1324 865218.9 8
163.0753 511429.6 4
163.1117 4019958.2 39
163.1481 285926.3 2
164.1196 650904.4 6
165.091 3461773.5 33
165.1274 2784545.2 27
167.1069 199455.3 1
167.1427 392737.5 3
169.0858 257382.1 2
169.1012 257784 2
170.1092 457928.4 4
171.1015 179717.5 1
171.1167 683259.4 6
172.1247 731150.3 7
173.096 353950.8 3
173.1326 1279572.4 12
174.1042 228970 2
174.1124 951770.1 9
175.1118 3712181 36
175.148 270885.8 2
176.1194 263001.3 2
177.1274 3057926.8 29
179.1068 621176.9 6
179.1428 187344.7 1
181.0858 483639.7 4
181.1222 434548.3 4
183.1017 348860.4 3
183.1166 202991.7 1
185.1324 634877.4 6
187.1119 281006.2 2
187.1481 1841707.6 17
188.1197 186155.8 1
189.1273 525643.9 5
191.1068 317604 3
191.1428 247727.4 2
193.1224 2238021 21
195.1379 616681.2 5
197.1325 277082.5 2
199.1484 104775 1
200.1194 224277.9 2
201.1275 312429.3 3
201.1638 269800 2
203.1065 435439.9 4
203.1429 517753.9 5
205.159 726134.2 7
210.1404 262156.4 2
211.1328 230860.9 2
213.1273 203693.6 1
215.1431 498893.9 4
221.1169 232566.2 2
221.1537 302527.6 2
225.1636 208589.3 2
229.1587 243440.5 2
231.1379 169869.5 1
233.1531 420481.5 4
249.1485 169722.6 1
251.164 205844.5 1
//
