ACCESSION: MSBNK-Eawag-EQ344608
RECORD_TITLE: Clarithromycin N-Oxide; LC-ESI-QFT; MS2; CE: 150; 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$MASS_SPECTROMETRY: COLLISION_ENERGY 150 (nominal)
AC$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$SPLASH: splash10-0aor-9200000000-9ca7376ca2eaa6b2e1aa
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
53.9975 C2NO+ 1 53.9974 0.18
54.0339 C3H4N+ 1 54.0338 0.45
55.0179 C3H3O+ 1 55.0178 0.34
55.0542 C4H7+ 1 55.0542 0.24
56.0495 C3H6N+ 1 56.0495 0.08
57.0335 C3H5O+ 1 57.0335 -0.02
57.0573 C3H7N+ 1 57.0573 -0.19
57.0699 C4H9+ 1 57.0699 0.06
58.0287 C2H4NO+ 1 58.0287 -0.35
58.0651 C3H8N+ 1 58.0651 0.25
59.0491 C3H7O+ 1 59.0491 -0.02
60.0444 C2H6NO+ 1 60.0444 -0.34
61.0284 C2H5O2+ 1 61.0284 -0.91
62.06 C2H8NO+ 1 62.06 0
63.0228 C5H3+ 1 63.0229 -1.37
65.0386 C5H5+ 1 65.0386 0.05
66.0464 C5H6+ 1 66.0464 -0.63
67.0542 C5H7+ 1 67.0542 0.05
67.9892 C3O2+ 1 67.9893 -1.04
68.0495 C4H6N+ 1 68.0495 0.21
69.0335 C4H5O+ 1 69.0335 -0.31
69.0573 C4H7N+ 1 69.0573 -0.01
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
72.0443 C3H6NO+ 1 72.0444 -0.56
72.0807 C4H10N+ 1 72.0808 -0.36
73.0522 C3H7NO+ 1 73.0522 -0.48
73.0648 C4H9O+ 1 73.0648 0.12
74.06 C3H8NO+ 1 74.06 -0.68
75.044 C3H7O2+ 1 75.0441 -1.14
77.0385 C6H5+ 1 77.0386 -0.6
78.0087 C3N3+ 1 78.0087 0.21
78.0464 C6H6+ 1 78.0464 -0.41
79.0542 C6H7+ 1 79.0542 -0.21
80.062 C6H8+ 1 80.0621 -0.52
81.0334 C5H5O+ 1 81.0335 -0.63
81.0699 C6H9+ 1 81.0699 0.04
82.0413 C5H6O+ 1 82.0413 -0.32
82.0651 C5H8N+ 1 82.0651 -0.56
83.0127 C4H3O2+ 1 83.0128 -0.07
83.0491 C5H7O+ 1 83.0491 -0.38
84.0808 C5H10N+ 1 84.0808 0.05
85.0284 C4H5O2+ 1 85.0284 0.05
85.0648 C5H9O+ 1 85.0648 -0.02
86.0601 C4H8NO+ 1 86.06 0.23
87.0678 C4H9NO+ 1 87.0679 -0.52
88.0757 C4H10NO+ 1 88.0757 -0.12
89.0384 C7H5+ 1 89.0386 -2.43
90.0463 C7H6+ 1 90.0464 -0.68
91.0542 C7H7+ 1 91.0542 0.26
92.062 C7H8+ 1 92.0621 -0.45
93.0699 C7H9+ 1 93.0699 0.47
94.0413 C6H6O+ 1 94.0413 0.25
94.0651 C6H8N+ 1 94.0651 -0.38
94.0777 C7H10+ 1 94.0777 0.51
95.0492 C6H7O+ 1 95.0491 0.2
95.0855 C7H11+ 1 95.0855 0.03
97.0649 C6H9O+ 1 97.0648 1.12
98.06 C5H8NO+ 1 98.06 -0.31
98.0964 C6H12N+ 1 98.0964 -0.16
100.112 C6H14N+ 1 100.1121 -0.26
102.0463 C8H6+ 1 102.0464 -1.49
103.0542 C8H7+ 1 103.0542 0.13
104.0621 C8H8+ 1 104.0621 0.27
105.0448 C6H5N2+ 1 105.0447 0.34
105.0699 C8H9+ 1 105.0699 0.32
106.0775 C8H10+ 1 106.0777 -1.52
107.0491 C7H7O+ 1 107.0491 -0.2
107.0855 C8H11+ 1 107.0855 0.22
108.057 C7H8O+ 1 108.057 -0.06
109.0648 C7H9O+ 1 109.0648 0.26
109.1012 C8H13+ 1 109.1012 0.58
111.0442 C6H7O2+ 1 111.0441 1.48
111.0805 C7H11O+ 1 111.0804 0.35
115.0543 C9H7+ 1 115.0542 0.29
116.062 C9H8+ 1 116.0621 -0.19
117.0698 C9H9+ 1 117.0699 -0.31
119.0604 C7H7N2+ 1 119.0604 0.13
119.0856 C9H11+ 1 119.0855 0.36
121.0648 C8H9O+ 1 121.0648 0.15
121.1011 C9H13+ 1 121.1012 -0.3
122.0726 C8H10O+ 1 122.0726 -0.3
123.0804 C8H11O+ 1 123.0804 -0.01
128.062 C10H8+ 1 128.0621 -0.09
129.0698 C10H9+ 1 129.0699 -0.36
130.0777 C10H10+ 1 130.0777 -0.17
131.0493 C9H7O+ 1 131.0491 1.13
131.0855 C10H11+ 1 131.0855 0.1
133.0649 C9H9O+ 1 133.0648 0.82
133.076 C8H9N2+ 1 133.076 -0.04
133.1012 C10H13+ 1 133.1012 0.02
135.0804 C9H11O+ 1 135.0804 -0.6
137.0961 C9H13O+ 1 137.0961 -0.01
138.0676 C8H10O2+ 1 138.0675 0.21
141.0699 C11H9+ 1 141.0699 0.31
142.0778 C11H10+ 1 142.0777 0.34
143.0857 C11H11+ 1 143.0855 1
145.0648 C10H9O+ 1 145.0648 0.27
145.101 C11H13+ 1 145.1012 -0.94
146.0722 C10H10O+ 1 146.0726 -3.06
147.0804 C10H11O+ 1 147.0804 -0.49
148.0883 C10H12O+ 1 148.0883 -0.04
149.0962 C10H13O+ 1 149.0961 0.66
152.0621 C12H8+ 1 152.0621 0.25
153.0696 C12H9+ 1 153.0699 -1.48
154.0773 C12H10+ 1 154.0777 -2.87
155.0605 C10H7N2+ 1 155.0604 0.94
155.0855 C12H11+ 1 155.0855 -0.17
156.0936 C12H12+ 1 156.0934 1.53
157.0646 C11H9O+ 1 157.0648 -1.03
157.1012 C12H13+ 1 157.1012 -0.11
159.0803 C11H11O+ 1 159.0804 -0.64
163.1117 C11H15O+ 1 163.1117 -0.32
165.0698 C13H9+ 1 165.0699 -0.34
167.0857 C13H11+ 1 167.0855 0.8
PK$NUM_PEAK: 118
PK$PEAK: m/z int. rel.int.
53.9975 545808.9 28
54.0339 135206.1 6
55.0179 1528561.8 78
55.0542 19425912 999
56.0495 1721009.6 88
57.0335 1827824.1 93
57.0573 498063.1 25
57.0699 508820.8 26
58.0287 134484.7 6
58.0651 2101378 108
59.0491 867371.9 44
60.0444 235275.3 12
61.0284 35347.9 1
62.06 221027.4 11
63.0228 61614.2 3
65.0386 7612564.5 391
66.0464 533803.9 27
67.0542 14591380 750
67.9892 83500.1 4
68.0495 799335.7 41
69.0335 1553850.5 79
69.0573 153005.3 7
69.0699 2181317.5 112
70.0651 1528265 78
71.0127 136799 7
71.0491 404984.8 20
71.0729 663900.6 34
72.0443 697860.5 35
72.0807 1177562.9 60
73.0522 142021.9 7
73.0648 314528.5 16
74.06 133617.8 6
75.044 44115 2
77.0385 1339560.1 68
78.0087 77262.5 3
78.0464 505031.8 25
79.0542 13140507 675
80.062 573760.7 29
81.0334 378263.2 19
81.0699 3841950.8 197
82.0413 38026.8 1
82.0651 468421.4 24
83.0127 882851.6 45
83.0491 7025438.5 361
84.0808 2477118.2 127
85.0284 595946.2 30
85.0648 162516.5 8
86.0601 244503.3 12
87.0678 59132.5 3
88.0757 52354 2
89.0384 72868.4 3
90.0463 131482.8 6
91.0542 13505690 694
92.062 197785.9 10
93.0699 2344316.2 120
94.0413 255357 13
94.0651 34352.4 1
94.0777 149969.9 7
95.0492 8074004.5 415
95.0855 1377709.9 70
97.0649 321179.6 16
98.06 188134.4 9
98.0964 545794.6 28
100.112 125364.5 6
102.0463 68313.9 3
103.0542 3212256.2 165
104.0621 661868.9 34
105.0448 3798762.2 195
105.0699 5443534 279
106.0775 244085.5 12
107.0491 1809857.5 93
107.0855 492263.8 25
108.057 1210491.8 62
109.0648 1788166.8 91
109.1012 254338.6 13
111.0442 37399.2 1
111.0805 53826.7 2
115.0543 1918026.6 98
116.062 419936.3 21
117.0698 1426905.9 73
119.0604 79815.3 4
119.0856 1264886.5 65
121.0648 580512.7 29
121.1011 145722.8 7
122.0726 443662 22
123.0804 3020172.8 155
128.062 1760504 90
129.0698 1376392.6 70
130.0777 232173.1 11
131.0493 82179.8 4
131.0855 292790.4 15
133.0649 64877.2 3
133.076 53741.2 2
133.1012 124189.2 6
135.0804 330594 17
137.0961 59375.4 3
138.0676 43791.2 2
141.0699 1091410.8 56
142.0778 589959.1 30
143.0857 368834.1 18
145.0648 300831.5 15
145.101 45820.1 2
146.0722 38157 1
147.0804 175281.5 9
148.0883 56809.9 2
149.0962 48917.5 2
152.0621 131342.5 6
153.0696 214404.5 11
154.0773 40588.1 2
155.0605 306467.8 15
155.0855 275402.9 14
156.0936 58903.4 3
157.0646 38409.8 1
157.1012 136371.3 7
159.0803 217847 11
163.1117 68304.8 3
165.0698 227982.1 11
167.0857 73734.4 3
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