ACCESSION: MSBNK-Eawag-EQ344609
RECORD_TITLE: Clarithromycin N-Oxide; LC-ESI-QFT; MS2; CE: 180; 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$MASS_SPECTROMETRY: COLLISION_ENERGY 180 (nominal)
AC$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$SPLASH: splash10-0aor-9200000000-98f1a13cb6e303d00f9f
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
53.9974 C2NO+ 1 53.9974 0
54.0339 C3H4N+ 1 54.0338 0.82
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 0.16
57.0699 C4H9+ 1 57.0699 0.06
58.0288 C2H4NO+ 1 58.0287 0.86
58.0651 C3H8N+ 1 58.0651 0.25
59.0491 C3H7O+ 1 59.0491 -0.02
60.0444 C2H6NO+ 1 60.0444 -0.67
61.0284 C2H5O2+ 1 61.0284 0.07
62.0601 C2H8NO+ 1 62.06 0.32
63.0229 C5H3+ 1 63.0229 -0.1
65.0386 C5H5+ 1 65.0386 0.21
66.0464 C5H6+ 1 66.0464 -0.33
67.0542 C5H7+ 1 67.0542 0.05
67.9892 C3O2+ 1 67.9893 -1.04
68.0495 C4H6N+ 1 68.0495 0.36
69.0335 C4H5O+ 1 69.0335 -0.16
69.0573 C4H7N+ 1 69.0573 -0.3
69.0699 C5H9+ 1 69.0699 -0.24
70.0651 C4H8N+ 1 70.0651 -0.08
71.0127 C3H3O2+ 1 71.0128 -0.5
71.0492 C4H7O+ 1 71.0491 0.4
71.0729 C4H9N+ 1 71.073 -0.43
72.0444 C3H6NO+ 1 72.0444 0
72.0808 C4H10N+ 1 72.0808 0.06
73.0522 C3H7NO+ 1 73.0522 0.2
73.0648 C4H9O+ 1 73.0648 0.26
74.0363 C3H6O2+ 1 74.0362 1.07
74.06 C3H8NO+ 1 74.06 -0.14
75.044 C3H7O2+ 1 75.0441 -1.01
77.0385 C6H5+ 1 77.0386 -0.86
78.0087 C3N3+ 1 78.0087 -0.17
78.0464 C6H6+ 1 78.0464 -0.41
79.0542 C6H7+ 1 79.0542 -0.08
80.062 C6H8+ 1 80.0621 -0.77
81.0335 C5H5O+ 1 81.0335 0.11
81.0699 C6H9+ 1 81.0699 0.04
82.0413 C5H6O+ 1 82.0413 -0.56
82.0651 C5H8N+ 1 82.0651 0.17
83.0128 C4H3O2+ 1 83.0128 0.05
83.0491 C5H7O+ 1 83.0491 -0.26
84.0808 C5H10N+ 1 84.0808 0.29
85.0284 C4H5O2+ 1 85.0284 0.17
85.0649 C5H9O+ 1 85.0648 0.69
86.06 C4H8NO+ 1 86.06 -0.35
87.0679 C4H9NO+ 1 87.0679 0.63
88.0756 C4H10NO+ 1 88.0757 -0.8
89.0386 C7H5+ 1 89.0386 -0.3
90.0464 C7H6+ 1 90.0464 -0.24
91.0543 C7H7+ 1 91.0542 0.37
92.0621 C7H8+ 1 92.0621 0.2
93.0699 C7H9+ 1 93.0699 0.47
94.0414 C6H6O+ 1 94.0413 0.47
94.0651 C6H8N+ 1 94.0651 -0.06
94.0778 C7H10+ 1 94.0777 0.62
95.0492 C6H7O+ 1 95.0491 0.2
95.0855 C7H11+ 1 95.0855 0.03
96.0807 C6H10N+ 1 96.0808 -0.37
97.0648 C6H9O+ 1 97.0648 -0.01
98.06 C5H8NO+ 1 98.06 -0.31
98.0964 C6H12N+ 1 98.0964 0.14
100.1122 C6H14N+ 1 100.1121 0.94
102.0464 C8H6+ 1 102.0464 -0.02
103.0542 C8H7+ 1 103.0542 0.13
104.062 C8H8+ 1 104.0621 -0.78
105.0448 C6H5N2+ 1 105.0447 0.34
105.0699 C8H9+ 1 105.0699 0.32
106.0777 C8H10+ 1 106.0777 -0.49
107.0491 C7H7O+ 1 107.0491 -0.01
107.0856 C8H11+ 1 107.0855 0.5
108.0569 C7H8O+ 1 108.057 -0.24
109.0648 C7H9O+ 1 109.0648 0.26
109.1012 C8H13+ 1 109.1012 0.67
111.0806 C7H11O+ 1 111.0804 0.98
115.0543 C9H7+ 1 115.0542 0.29
116.062 C9H8+ 1 116.0621 -0.1
117.0699 C9H9+ 1 117.0699 0.03
118.0778 C9H10+ 1 118.0777 0.49
119.0604 C7H7N2+ 1 119.0604 0.55
119.0855 C9H11+ 1 119.0855 0.2
121.0648 C8H9O+ 1 121.0648 -0.01
121.101 C9H13+ 1 121.1012 -1.71
122.0726 C8H10O+ 1 122.0726 -0.54
123.0804 C8H11O+ 1 123.0804 -0.09
125.0597 C7H9O2+ 1 125.0597 -0.37
128.0621 C10H8+ 1 128.0621 0.3
129.0699 C10H9+ 1 129.0699 0.1
130.0776 C10H10+ 1 130.0777 -0.47
131.0493 C9H7O+ 1 131.0491 0.98
131.0856 C10H11+ 1 131.0855 0.48
133.0648 C9H9O+ 1 133.0648 -0.09
133.1011 C10H13+ 1 133.1012 -0.28
135.0806 C9H11O+ 1 135.0804 1.4
136.0884 C9H12O+ 1 136.0883 1.28
137.0965 C9H13O+ 1 137.0961 3.13
141.0698 C11H9+ 1 141.0699 -0.4
142.0777 C11H10+ 1 142.0777 0.06
143.0856 C11H11+ 1 143.0855 0.51
145.0646 C10H9O+ 1 145.0648 -1.18
145.1012 C11H13+ 1 145.1012 0.02
147.0805 C10H11O+ 1 147.0804 0.6
149.0959 C10H13O+ 1 149.0961 -1.35
151.0758 C9H11O2+ 1 151.0754 2.87
152.062 C12H8+ 1 152.0621 -0.47
153.0699 C12H9+ 1 153.0699 -0.04
154.0775 C12H10+ 1 154.0777 -1.37
155.0604 C10H7N2+ 1 155.0604 0.1
155.0856 C12H11+ 1 155.0855 0.54
156.0934 C12H12+ 1 156.0934 0.63
157.0651 C11H9O+ 1 157.0648 2.09
157.1012 C12H13+ 1 157.1012 0.47
159.0804 C11H11O+ 1 159.0804 -0.2
163.1115 C11H15O+ 1 163.1117 -1.48
165.0694 C13H9+ 1 165.0699 -3.13
166.0776 C13H10+ 1 166.0777 -0.43
167.0855 C13H11+ 1 167.0855 -0.1
179.1069 C11H15O2+ 1 179.1067 1.36
PK$NUM_PEAK: 121
PK$PEAK: m/z int. rel.int.
53.9974 489329.1 22
54.0339 59928.8 2
55.0179 1750035.5 82
55.0543 21301314 999
56.0495 1707015.9 80
57.0335 2039248.9 95
57.0573 454759.2 21
57.0699 590622.8 27
58.0288 139715.9 6
58.0651 2683745.8 125
59.0491 900939.4 42
60.0444 289693.7 13
61.0284 33942.9 1
62.0601 168546.3 7
63.0229 69492.1 3
65.0386 7826796 367
66.0464 536032.2 25
67.0542 15510187 727
67.9892 143270.4 6
68.0495 873581 40
69.0335 1553046.9 72
69.0573 150656.7 7
69.0699 2183041 102
70.0651 1414867.6 66
71.0127 182904.2 8
71.0492 391931.4 18
71.0729 890374.4 41
72.0444 799054.9 37
72.0808 1279059 59
73.0522 74839.1 3
73.0648 241083.2 11
74.0363 67945.9 3
74.06 80194 3
75.044 50024.2 2
77.0385 1627589.6 76
78.0087 166235.8 7
78.0464 545737.8 25
79.0542 13976725 655
80.062 735711.5 34
81.0335 416297.4 19
81.0699 3863489 181
82.0413 67047 3
82.0651 403446.4 18
83.0128 908852.8 42
83.0491 8085323 379
84.0808 2430127 113
85.0284 679432.3 31
85.0649 263990.2 12
86.06 233988.6 10
87.0679 147015.6 6
88.0756 47827.4 2
89.0386 34748.1 1
90.0464 45445.4 2
91.0543 15032212 704
92.0621 170848.8 8
93.0699 2354399.8 110
94.0414 223361.5 10
94.0651 43761 2
94.0778 154950 7
95.0492 7807283 366
95.0855 1635233.4 76
96.0807 38931.1 1
97.0648 333336 15
98.06 85019.2 3
98.0964 584791.8 27
100.1122 131392.4 6
102.0464 75686.1 3
103.0542 3660693 171
104.062 604580.1 28
105.0448 4019432 188
105.0699 6311539.5 296
106.0777 299694.2 14
107.0491 2054079.2 96
107.0856 542684.5 25
108.0569 1138777.5 53
109.0648 1697229.2 79
109.1012 234812.2 11
111.0806 56124.6 2
115.0543 2209021.5 103
116.062 384616.4 18
117.0699 1679928.5 78
118.0778 47662.2 2
119.0604 166907.3 7
119.0855 1792707.5 84
121.0648 803791.4 37
121.101 183905.6 8
122.0726 626549.4 29
123.0804 3555564.2 166
125.0597 42584 1
128.0621 1585323.1 74
129.0699 1502178 70
130.0776 299184.7 14
131.0493 81601.7 3
131.0856 297967.2 13
133.0648 125129.6 5
133.1011 82175.6 3
135.0806 330561.2 15
136.0884 59821.7 2
137.0965 43379.6 2
141.0698 1080190.8 50
142.0777 663748.5 31
143.0856 473971.7 22
145.0646 383578.3 17
145.1012 79082.1 3
147.0805 133989.9 6
149.0959 55009.1 2
151.0758 45459.1 2
152.062 185991.1 8
153.0699 201274.7 9
154.0775 61755.8 2
155.0604 211422.4 9
155.0856 300727.9 14
156.0934 56458.2 2
157.0651 41433.3 1
157.1012 211073.9 9
159.0804 227794.5 10
163.1115 121474.8 5
165.0694 278601.5 13
166.0776 63951 2
167.0855 72268.1 3
179.1069 35707.9 1
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