ACCESSION: MSBNK-Eawag-EQ344605
RECORD_TITLE: Clarithromycin N-Oxide; LC-ESI-QFT; MS2; CE: 75; 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$MASS_SPECTROMETRY: COLLISION_ENERGY 75 (nominal)
AC$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$SPLASH: splash10-00e9-9800000000-e1cb1b1f43b0c532ab4e
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
53.9975 C2NO+ 1 53.9974 0.18
55.0178 C3H3O+ 1 55.0178 -0.02
55.0542 C4H7+ 1 55.0542 0.24
56.0495 C3H6N+ 1 56.0495 0.08
57.0335 C3H5O+ 1 57.0335 -0.02
57.0699 C4H9+ 1 57.0699 -0.12
58.0651 C3H8N+ 1 58.0651 -0.1
59.0491 C3H7O+ 1 59.0491 -0.19
60.0444 C2H6NO+ 1 60.0444 0
62.06 C2H8NO+ 1 62.06 -0.17
65.0386 C5H5+ 1 65.0386 -0.25
67.0542 C5H7+ 1 67.0542 -0.1
67.9893 C3O2+ 1 67.9893 0.28
68.0495 C4H6N+ 1 68.0495 -0.23
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 -0.3
71.0729 C4H9N+ 1 71.073 -0.57
71.0856 C5H11+ 1 71.0855 0.47
72.0444 C3H6NO+ 1 72.0444 -0.28
72.0807 C4H10N+ 1 72.0808 -0.36
73.0284 C3H5O2+ 1 73.0284 -0.76
73.0522 C3H7NO+ 1 73.0522 -0.21
73.0648 C4H9O+ 1 73.0648 -0.29
74.0599 C3H8NO+ 1 74.06 -1.62
75.0441 C3H7O2+ 1 75.0441 0.05
77.0384 C6H5+ 1 77.0386 -1.77
79.0542 C6H7+ 1 79.0542 -0.46
80.062 C6H8+ 1 80.0621 -1.02
81.0699 C6H9+ 1 81.0699 0.04
82.0651 C5H8N+ 1 82.0651 -0.43
83.0491 C5H7O+ 1 83.0491 -0.5
84.0808 C5H10N+ 1 84.0808 -0.07
85.0284 C4H5O2+ 1 85.0284 -0.19
85.0648 C5H9O+ 1 85.0648 -0.25
86.06 C4H8NO+ 1 86.06 -0.47
87.0441 C4H7O2+ 1 87.0441 0.39
87.0679 C4H9NO+ 1 87.0679 0.05
87.0805 C5H11O+ 1 87.0804 0.33
88.0757 C4H10NO+ 1 88.0757 0
91.0542 C7H7+ 1 91.0542 0.15
93.0699 C7H9+ 1 93.0699 0.36
95.0492 C6H7O+ 1 95.0491 0.2
95.0855 C7H11+ 1 95.0855 0.03
97.0284 C5H5O2+ 1 97.0284 0.35
97.0648 C6H9O+ 1 97.0648 0.19
98.0602 C5H8NO+ 1 98.06 1.53
98.0964 C6H12N+ 1 98.0964 0.14
99.0442 C5H7O2+ 1 99.0441 1.05
99.0804 C6H11O+ 1 99.0804 -0.22
99.1043 C6H13N+ 1 99.1043 0.19
100.0757 C5H10NO+ 1 100.0757 0.6
100.1121 C6H14N+ 1 100.1121 -0.16
101.0234 C4H5O3+ 1 101.0233 0.39
101.0597 C5H9O2+ 1 101.0597 -0.55
102.0914 C5H12NO+ 1 102.0913 0.39
103.0542 C8H7+ 1 103.0542 -0.06
104.062 C8H8+ 1 104.0621 -0.5
105.0448 C6H5N2+ 1 105.0447 0.53
105.0699 C8H9+ 1 105.0699 0.22
106.0777 C8H10+ 1 106.0777 -0.11
107.0492 C7H7O+ 1 107.0491 0.36
107.0855 C8H11+ 1 107.0855 -0.06
108.0569 C7H8O+ 1 108.057 -0.61
108.0934 C8H12+ 1 108.0934 0.08
109.0648 C7H9O+ 1 109.0648 0.26
109.1012 C8H13+ 1 109.1012 0.12
110.0725 C7H10O+ 1 110.0726 -1.24
111.044 C6H7O2+ 1 111.0441 -0.5
111.0804 C7H11O+ 1 111.0804 -0.01
113.0597 C6H9O2+ 1 113.0597 -0.32
113.096 C7H13O+ 1 113.0961 -0.45
114.0913 C6H12NO+ 1 114.0913 -0.09
115.0542 C9H7+ 1 115.0542 -0.14
115.0753 C6H11O2+ 1 115.0754 -0.4
116.0707 C5H10NO2+ 1 116.0706 0.9
116.107 C6H14NO+ 1 116.107 0.43
117.0698 C9H9+ 1 117.0699 -0.4
119.0856 C9H11+ 1 119.0855 0.36
120.0935 C9H12+ 1 120.0934 0.82
121.0648 C8H9O+ 1 121.0648 -0.34
121.1012 C9H13+ 1 121.1012 0.19
122.0726 C8H10O+ 1 122.0726 -0.05
123.0804 C8H11O+ 1 123.0804 -0.34
124.0883 C8H12O+ 1 124.0883 0.19
125.0597 C7H9O2+ 1 125.0597 0.11
125.0961 C8H13O+ 1 125.0961 -0.09
127.0754 C7H11O2+ 1 127.0754 0.11
127.1117 C8H15O+ 1 127.1117 -0.41
128.0619 C10H8+ 1 128.0621 -1.5
128.107 C7H14NO+ 1 128.107 -0.32
129.0698 C10H9+ 1 129.0699 -0.28
130.0778 C10H10+ 1 130.0777 0.6
131.0855 C10H11+ 1 131.0855 0.02
132.0656 C5H10NO3+ 1 132.0655 0.23
133.0648 C9H9O+ 1 133.0648 -0.24
133.076 C8H9N2+ 1 133.076 -0.34
133.1012 C10H13+ 1 133.1012 0.02
134.109 C10H14+ 1 134.109 -0.16
135.0804 C9H11O+ 1 135.0804 -0.53
135.1168 C10H15+ 1 135.1168 -0.35
136.0883 C9H12O+ 1 136.0883 0.61
137.0961 C9H13O+ 1 137.0961 0.14
139.0753 C8H11O2+ 1 139.0754 -0.26
139.1117 C9H15O+ 1 139.1117 -0.15
140.1069 C8H14NO+ 1 140.107 -0.57
142.0777 C11H10+ 1 142.0777 0.13
143.0856 C11H11+ 1 143.0855 0.16
144.0934 C11H12+ 1 144.0934 0.06
145.0648 C10H9O+ 1 145.0648 -0.08
145.1011 C11H13+ 1 145.1012 -0.18
146.0727 C10H10O+ 1 146.0726 0.57
147.0804 C10H11O+ 1 147.0804 -0.08
147.1168 C11H15+ 1 147.1168 -0.18
149.0962 C10H13O+ 1 149.0961 0.46
149.1326 C11H17+ 1 149.1325 0.62
150.1039 C10H14O+ 1 150.1039 -0.04
151.0754 C9H11O2+ 1 151.0754 0.03
151.1117 C10H15O+ 1 151.1117 -0.08
152.0832 C9H12O2+ 1 152.0832 0.39
153.091 C9H13O2+ 1 153.091 0.09
155.0856 C12H11+ 1 155.0855 0.73
155.1065 C9H15O2+ 1 155.1067 -0.75
156.0935 C12H12+ 1 156.0934 1.01
157.1012 C12H13+ 1 157.1012 -0.11
158.1089 C12H14+ 1 158.109 -0.45
159.0805 C11H11O+ 1 159.0804 0.31
159.1168 C12H15+ 1 159.1168 -0.04
160.0883 C11H12O+ 1 160.0883 -0.04
161.0961 C11H13O+ 1 161.0961 -0.13
161.1327 C12H17+ 1 161.1325 1.26
162.1041 C11H14O+ 1 162.1039 0.82
163.0751 C10H11O2+ 1 163.0754 -1.51
163.1117 C11H15O+ 1 163.1117 -0.32
164.1197 C11H16O+ 1 164.1196 1.06
165.0911 C10H13O2+ 1 165.091 0.39
165.1275 C11H17O+ 1 165.1274 0.47
168.0935 C13H12+ 1 168.0934 1
169.1011 C13H13+ 1 169.1012 -0.22
170.1092 C13H14+ 1 170.109 1.16
171.1169 C13H15+ 1 171.1168 0.54
172.0882 C12H12O+ 1 172.0883 -0.15
172.1246 C13H16+ 1 172.1247 -0.07
173.0959 C12H13O+ 1 173.0961 -1.39
173.1323 C13H17+ 1 173.1325 -0.96
174.104 C12H14O+ 1 174.1039 0.59
174.1121 C8H16NO3+ 1 174.1125 -2.01
175.1118 C12H15O+ 1 175.1117 0.16
176.1197 C12H16O+ 1 176.1196 0.53
177.1274 C12H17O+ 1 177.1274 -0.01
179.1066 C11H15O2+ 1 179.1067 -0.26
181.0855 C10H13O3+ 1 181.0859 -2.27
181.101 C14H13+ 1 181.1012 -1.03
183.117 C14H15+ 1 183.1168 0.73
185.1326 C14H17+ 1 185.1325 0.83
186.1036 C13H14O+ 1 186.1039 -1.81
187.1119 C13H15O+ 1 187.1117 0.58
187.148 C14H19+ 1 187.1481 -0.68
188.1194 C13H16O+ 1 188.1196 -0.94
189.1273 C13H17O+ 1 189.1274 -0.75
193.1222 C12H17O2+ 1 193.1223 -0.76
195.1168 C15H15+ 1 195.1168 0.12
197.1325 C15H17+ 1 197.1325 -0.14
201.1272 C14H17O+ 1 201.1274 -1.2
203.1429 C14H19O+ 1 203.143 -0.7
213.1271 C15H17O+ 1 213.1274 -1.27
215.1429 C15H19O+ 1 215.143 -0.57
PK$NUM_PEAK: 168
PK$PEAK: m/z int. rel.int.
53.9975 191518.3 2
55.0178 973297.7 13
55.0542 14065284 196
56.0495 1210690.8 16
57.0335 5874393 82
57.0699 3047627.8 42
58.0651 3525622.2 49
59.0491 1361838.9 19
60.0444 781800.1 10
62.06 1112355.9 15
65.0386 3159600.8 44
67.0542 26861600 375
67.9893 81608.2 1
68.0495 286766.3 4
69.0335 5249273 73
69.0699 15318933 214
70.0651 5750890 80
71.0491 1925189.5 26
71.0729 914170.4 12
71.0856 244361.6 3
72.0444 1790657.6 25
72.0807 2951949 41
73.0284 314589.6 4
73.0522 251700 3
73.0648 970809.2 13
74.0599 430067.2 6
75.0441 88642.8 1
77.0384 434698.5 6
79.0542 7867016 109
80.062 79993.4 1
81.0699 10527988 147
82.0651 581908.6 8
83.0491 37407884 522
84.0808 7198662.5 100
85.0284 3097384 43
85.0648 2810161.2 39
86.06 2140368.8 29
87.0441 525188.2 7
87.0679 456545.2 6
87.0805 73099.1 1
88.0757 2469962.5 34
91.0542 7254694 101
93.0699 7472476.5 104
95.0492 7759677.5 108
95.0855 10763705 150
97.0284 481486 6
97.0648 6384630 89
98.0602 301363.4 4
98.0964 2863186.5 40
99.0442 97780 1
99.0804 787853.3 11
99.1043 181507.5 2
100.0757 256018.7 3
100.1121 2489898 34
101.0234 106345.6 1
101.0597 698211.7 9
102.0914 276822.9 3
103.0542 1153167.4 16
104.062 90268.8 1
105.0448 770489.4 10
105.0699 11922062 166
106.0777 370331 5
107.0492 496603.7 6
107.0855 7239089.5 101
108.0569 641730.9 8
108.0934 77194.8 1
109.0648 12105400 169
109.1012 10048493 140
110.0725 74302.6 1
111.044 1104320.9 15
111.0804 1667767.9 23
113.0597 3231254.2 45
113.096 614757 8
114.0913 854366.1 11
115.0542 326468.8 4
115.0753 229309.9 3
116.0707 181504.9 2
116.107 163560.9 2
117.0698 1445643 20
119.0856 9899110 138
120.0935 211580.2 2
121.0648 876779.6 12
121.1012 14202146 198
122.0726 1077103.4 15
123.0804 71482688 999
124.0883 250629.5 3
125.0597 1046858.3 14
125.0961 3454124.5 48
127.0754 587177.9 8
127.1117 186182.3 2
128.0619 302048.6 4
128.107 713382.8 9
129.0698 850585.2 11
130.0778 265431.2 3
131.0855 1662140.2 23
132.0656 845280.4 11
133.0648 302160.9 4
133.076 812310.9 11
133.1012 2375332 33
134.109 102753.8 1
135.0804 1924212.2 26
135.1168 1006327.4 14
136.0883 742548 10
137.0961 8607946 120
139.0753 512256.4 7
139.1117 597415.9 8
140.1069 378036.3 5
142.0777 798917.8 11
143.0856 656713.3 9
144.0934 1179054.5 16
145.0648 228552.4 3
145.1011 1833340.6 25
146.0727 89112.9 1
147.0804 995457 13
147.1168 2905004 40
149.0962 1084460.8 15
149.1326 851257.1 11
150.1039 87013.4 1
151.0754 988030.6 13
151.1117 1034684.7 14
152.0832 260275.7 3
153.091 427675.3 5
155.0856 292156.7 4
155.1065 93654.7 1
156.0935 430426.4 6
157.1012 1658787.2 23
158.1089 557931 7
159.0805 305316.9 4
159.1168 1925197.8 26
160.0883 430113.2 6
161.0961 700965.6 9
161.1327 213962.1 2
162.1041 102916.2 1
163.0751 230264.9 3
163.1117 1797330.8 25
164.1197 457751.7 6
165.0911 877019.6 12
165.1275 751256.8 10
168.0935 74756.9 1
169.1011 260236.5 3
170.1092 516968.3 7
171.1169 427728.5 5
172.0882 184123.6 2
172.1246 597847.9 8
173.0959 265778.8 3
173.1323 563152.2 7
174.104 192842 2
174.1121 79479.1 1
175.1118 1234212.2 17
176.1197 77518.2 1
177.1274 976717.4 13
179.1066 315483.4 4
181.0855 87072.8 1
181.101 100443.3 1
183.117 105787.2 1
185.1326 226509.4 3
186.1036 86214.7 1
187.1119 256050.1 3
187.148 260413.5 3
188.1194 103199.4 1
189.1273 244388.9 3
193.1222 292264.6 4
195.1168 255458.8 3
197.1325 93801.3 1
201.1272 257264.3 3
203.1429 94416.1 1
213.1271 77739.5 1
215.1429 102366.6 1
//
