Standard Article

N-Arylhydroxylamines and Chemical Carcinogenicity

Hydroxylamines, Oximes and Hydroxamic Acids (2010)

  1. Michael Novak,
  2. Mrinal Chakraborty

Published Online: 15 SEP 2010

DOI: 10.1002/9780470682531.pat0507

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

Novak, M. and Chakraborty, M. 2010. N-Arylhydroxylamines and Chemical Carcinogenicity. Patai's Chemistry of Functional Groups. .

Author Information

Publication History

  1. Published Online: 15 SEP 2010

Chemistry Terms

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Abstract

  • 1
    Introduction
  • 2
    Metabolic Activation of AAs and HAAs
  • 3
    The Structures of DNA Adducts
  • 4
    The Nitrenium Ion Hypothesis
  • 5
    The Hypothesis Tested
  • 6
    Concluding Remarks

Two related classes of carcinogens, arylamines (AAs) and heterocyclic arylamines (HAAs), have played an important role in the development of our understanding of chemical carcinogenesis. AAs are largely industrial products or by-products, but significant exposure also occurs through inhalation of cigarette smoke. HAAs are produced during broiling or frying of meats and fish and are viewed as significant cancer risks in most human populations. AAs and HAAs are properly characterized as procarcinogens because they require metabolic activation into their ultimate carcinogenic forms. Both classes are activated predominately by cytochrome P450 (CYP450) mediated oxidation into N-arylhydroxylamines that are further metabolized into acetic or sulfuric acid esters of the hydroxylamines by the action of N-acetyltransferases (NATs) or sulfotransferases (SULTs). These esters appear to be the ultimate carcinogens in most cases. Research on the metabolism of AAs and HAAs, the structures of DNA adducts derived from their carcinogenic metabolites, and the relationship of DNA adduct conformations and persistence to observed mutations are reviewed. Evidence for the proposal that the reactive intermediate responsible for the formation of DNA adducts is a nitrenium ion derived from the hydroxylamine esters is the main topic of this review. Future prospects for research in this area are considered.

Keywords:

  • Arylamines;
  • Heterocyclic arylamines;
  • N-arylhydroxylamines;
  • Cytochrome P450;
  • N-acetyltransferase;
  • Sulfotransferase;
  • C-8 Adduct;
  • N2 Adduct;
  • Nitrenium ions

Featured Compounds

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  1. 1 - 184
Compound 2-AF
Molecular Weight:181.2331
Molecular Formula:C13H11N
InChIKey:CFRFHWQYWJMEJN-UHFFFAOYSA-N
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Compound 1
Molecular Weight:239.2692
Molecular Formula:C15H13NO2
InChIKey:SOKUIEGXJHVFDV-UHFFFAOYSA-N
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Compound 3
Molecular Weight:318.325
Molecular Formula:C15H13NO5S
InChIKey:VAQHXJKAFOKQTD-UHFFFAOYSA-M
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Compound 2
Molecular Weight:197.2325
Molecular Formula:C13H11NO
InChIKey:JJCLXJPUTJMRTM-UHFFFAOYSA-N
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Compound 4
Molecular Weight:276.288
Molecular Formula:C13H11NO4S
InChIKey:ASQVEYUODMRXBR-UHFFFAOYSA-M
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Compound 5
Molecular Weight:239.2692
Molecular Formula:C15H13NO2
InChIKey:DAJPHRKDAWYAJZ-UHFFFAOYSA-N
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Compound 7
Molecular Weight:256.26
Molecular Formula:C13H12N4O2
InChIKey:ZNLLBBZONQYLII-UHFFFAOYSA-N
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Compound 6
Molecular Weight:214.2233
Molecular Formula:C11H10N4O
InChIKey:QYFQSQCBYZOECM-UHFFFAOYSA-N
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Compound 8
Molecular Weight:240.2606
Molecular Formula:C13H12N4O
InChIKey:DCVWQAGUQFBCTF-UHFFFAOYSA-N
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Compound 9
Molecular Weight:319.316
Molecular Formula:C13H12N4O4S
InChIKey:LPVOGSWZCYNQGE-UHFFFAOYSA-M
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Compound 10
Molecular Weight:281.3059
Molecular Formula:C17H15NO3
InChIKey:NFOMHWALMFWNAQ-UHFFFAOYSA-N
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Compound 11
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 12
Molecular Weight:330.3434
Molecular Formula:C18H14N6O
InChIKey:XFLKJEFDRUGBPK-UHFFFAOYSA-N
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Compound 13
Molecular Weight:462.458
Molecular Formula:C23H22N6O5
InChIKey:JIZHFPQGDVSPBL-QTQZEZTPSA-N
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Compound 14
Molecular Weight:488.4953
Molecular Formula:C25H24N6O5
InChIKey:QHNMSPBQWLPAMP-XUVXKRRUSA-N
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Compound 15
Molecular Weight:446.4586
Molecular Formula:C23H22N6O4
InChIKey:RMYQNJYFBAYPNG-RCCFBDPRSA-N
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Compound 16
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 17
Molecular Weight:326.3465
Molecular Formula:C18H18N2O4
InChIKey:KNLNOJBZVQVWFQ-UHFFFAOYSA-N
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Compound 18
Molecular Weight:242.2732
Molecular Formula:C14H14N2O2
InChIKey:MZCOYFQGPZRXCS-UHFFFAOYSA-N
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Compound 19
Molecular Weight:533.5359
Molecular Formula:C26H27N7O6
InChIKey:YIZUHBCLBGXHBM-PWRODBHTSA-N
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Compound 20
Molecular Weight:491.4992
Molecular Formula:C24H25N7O5
InChIKey:AHBQGNZJQFIGBI-IPMKNSEASA-N
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Compound 21
Molecular Weight:491.4992
Molecular Formula:C24H25N7O5
InChIKey:BJJUQBWYLRXWNN-IPMKNSEASA-N
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Compound 22
Molecular Weight:449.4625
Molecular Formula:C22H23N7O4
InChIKey:KRXNALOGQHZLOT-GVDBMIGSSA-N
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Compound 23a
Molecular Weight:165.1891
Molecular Formula:C9H11NO2
InChIKey:MZXGZMPPXQETLI-UHFFFAOYSA-N
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Compound 23b
Molecular Weight:165.1891
Molecular Formula:C9H11NO2
InChIKey:JXJRAGXQNMRHHC-UHFFFAOYSA-N
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Compound 23c
Molecular Weight:165.1891
Molecular Formula:C9H11NO2
InChIKey:RXHZTWUCCZNGCI-UHFFFAOYSA-N
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Compound 23d
Molecular Weight:179.2157
Molecular Formula:C10H13NO2
InChIKey:AGGGMIBELKETSL-UHFFFAOYSA-N
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Compound 23e
Molecular Weight:179.2157
Molecular Formula:C10H13NO2
InChIKey:UINUVSSXFUKEEG-UHFFFAOYSA-N
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Compound 24a
Molecular Weight:372.3785
Molecular Formula:C17H20N6O4
InChIKey:LJWQTUFXXNEEIU-QJPTWQEYSA-N
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Compound 24b
Molecular Weight:372.3785
Molecular Formula:C17H20N6O4
InChIKey:JXNAAKWTLCIASO-QJPTWQEYSA-N
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Compound 24c
Molecular Weight:372.3785
Molecular Formula:C17H20N6O4
InChIKey:SHOPSBOWUOUXGM-QJPTWQEYSA-N
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Compound 24d
Molecular Weight:386.4051
Molecular Formula:C18H22N6O4
InChIKey:ABXRLICUWWMCQJ-YNEHKIRRSA-N
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Compound 24e
Molecular Weight:386.4051
Molecular Formula:C18H22N6O4
InChIKey:WMRFYSQGZZOGAD-YNEHKIRRSA-N
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Compound 23f
Molecular Weight:179.2157
Molecular Formula:C10H13NO2
InChIKey:CGTOJFFPAUHSIZ-UHFFFAOYSA-N
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Compound 23g
Molecular Weight:179.2157
Molecular Formula:C10H13NO2
InChIKey:MHIHBHGWEWLFPV-UHFFFAOYSA-N
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Compound 24g
Molecular Weight:386.4051
Molecular Formula:C18H22N6O4
InChIKey:XSEWRIOEEJZMOW-YNEHKIRRSA-N
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Compound 27f
Molecular Weight:370.4057
Molecular Formula:C18H22N6O3
InChIKey:RXKFODGGONFJJR-BFHYXJOUSA-N
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Compound 27g
Molecular Weight:370.4057
Molecular Formula:C18H22N6O3
InChIKey:OWKFBBACIMLHEO-BFHYXJOUSA-N
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Compound 28g
Molecular Weight:370.4057
Molecular Formula:C18H22N6O3
InChIKey:VFNDHJYZAUDEQP-BFHYXJOUSA-N
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Compound 29g
Molecular Weight:346.381
Molecular Formula:C17H22N4O4
InChIKey:SMRUEIMKZODMFH-RRFJBIMHSA-N
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Compound 23
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 24
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 24f
Molecular Weight:386.4051
Molecular Formula:C18H22N6O4
InChIKey:IQRGAHLECAFOBY-QJPTWQEYSA-N
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Compound 25f
Molecular Weight:386.4051
Molecular Formula:C18H22N6O4
InChIKey:WCVJCKWEIGJLJX-YNEHKIRRSA-N
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Compound 26f
Molecular Weight:386.4051
Molecular Formula:C18H22N6O4
InChIKey:LZNNTQLDLHCDET-YNEHKIRRSA-N
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Compound 30
Molecular Weight:463.4493
Molecular Formula:C21H21N9O4
InChIKey:WSJRBAXOXGNYRR-OUCADQQQSA-N
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Compound 31
Molecular Weight:462.4613
Molecular Formula:C22H22N8O4
InChIKey:YPSZQNFUZFCWIO-SQWLQELKSA-N
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Compound 32a
Molecular Weight:448.4347
Molecular Formula:C21H20N8O4
InChIKey:ZRBVUIRPSABEGI-GZBFAFLISA-N
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Compound 32b
Molecular Weight:462.4613
Molecular Formula:C22H22N8O4
InChIKey:OZJVEWFWKNVDGX-RRFJBIMHSA-N
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Compound 32
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 33
Molecular Weight:489.4866
Molecular Formula:C23H23N9O4
InChIKey:UHVGJHQDVDVQHH-ARFHVFGLSA-N
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Compound 34
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 34a
Molecular Weight:463.4493
Molecular Formula:C21H21N9O4
InChIKey:BUWFHGJSHMKENO-BFHYXJOUSA-N
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Compound 34b
Molecular Weight:477.4759
Molecular Formula:C22H23N9O4
InChIKey:XBDWJVFPPWWXOR-BFHYXJOUSA-N
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Compound 34c
Molecular Weight:478.464
Molecular Formula:C21H22N10O4
InChIKey:ATNHUXHBJPMSBV-YNEHKIRRSA-N
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Compound 35
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 35a
Molecular Weight:463.4493
Molecular Formula:C21H21N9O4
InChIKey:JGGDEQWCMVVRSC-BFHYXJOUSA-N
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Compound 35c
Molecular Weight:478.464
Molecular Formula:C21H22N10O4
InChIKey:OYDMPQZHCQFIDK-YNEHKIRRSA-N
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Compound 36
Molecular Weight:358.3519
Molecular Formula:C16H18N6O4
InChIKey:BDNZPDKBUOXLOI-HBNTYKKESA-N
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Compound 37
Molecular Weight:434.4479
Molecular Formula:C22H22N6O4
InChIKey:JPQHAFBEGLGQRF-GVDBMIGSSA-N
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Compound 38
Molecular Weight:482.4907
Molecular Formula:C26H22N6O4
InChIKey:QBMJHUSBJZIUSS-IPMKNSEASA-N
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Compound 39
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 40a
Molecular Weight:295.3325
Molecular Formula:C18H17NO3
InChIKey:DQOBUTWTHQJLSG-CMDGGOBGSA-N
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Compound 40b
Molecular Weight:269.2952
Molecular Formula:C16H15NO3
InChIKey:UJDATCBZIHYYMW-UHFFFAOYSA-N
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Compound 40c
Molecular Weight:293.3166
Molecular Formula:C18H15NO3
InChIKey:PBUJMRDTXSUQHF-UHFFFAOYSA-N
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Compound 40d
Molecular Weight:243.2579
Molecular Formula:C14H13NO3
InChIKey:SAUDWTVJBPRWGL-UHFFFAOYSA-N
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Compound 40e
Molecular Weight:243.2579
Molecular Formula:C14H13NO3
InChIKey:RLBVXZVYDBANEV-UHFFFAOYSA-N
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Compound 41a
Molecular Weight:281.3059
Molecular Formula:C17H15NO3
InChIKey:UUFCCPUIZIGBPJ-UHFFFAOYSA-N
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Compound 41b
Molecular Weight:281.3059
Molecular Formula:C17H15NO3
InChIKey:ZNJHDEZOETZXIX-UHFFFAOYSA-N
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Compound 42a
Molecular Weight:239.2692
Molecular Formula:C15H13NO2
InChIKey:IQPIBKBOFOVHBP-UHFFFAOYSA-N
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Compound 42b
Molecular Weight:239.2692
Molecular Formula:C15H13NO2
InChIKey:MNPABTKJCQDDNY-UHFFFAOYSA-N
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Compound 43a
Molecular Weight:244.245
Molecular Formula:C9H11NO5S
InChIKey:NZXBMWJDGLMCRT-UHFFFAOYSA-M
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Compound 43b
Molecular Weight:230.218
Molecular Formula:C8H9NO5S
InChIKey:GKEQAUATBSENAJ-UHFFFAOYSA-M
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Compound 43c
Molecular Weight:264.663
Molecular Formula:C8H8ClNO5S
InChIKey:CQBHMVRFIRQQBT-UHFFFAOYSA-M
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Compound 43d
Molecular Weight:309.114
Molecular Formula:C8H8BrNO5S
InChIKey:WXXGDGOGFOMDFC-UHFFFAOYSA-M
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Compound 41
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 42
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 43
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 46
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 47
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 48
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 49
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 50
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 51
Molecular Weight:149.1467
Molecular Formula:C8H7NO2
InChIKey:URNSECGXFRDEDC-UHFFFAOYSA-N
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Compound 52
Molecular Weight:151.1626
Molecular Formula:C8H9NO2
InChIKey:RZVAJINKPMORJF-UHFFFAOYSA-N
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Compound 53
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 53a
Molecular Weight:263.698
Molecular Formula:C9H10ClNO4S
InChIKey:LGJXDBQAIZFZEJ-UHFFFAOYSA-N
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Compound 53b
Molecular Weight:287.289
Molecular Formula:C11H13NO6S
InChIKey:IREYPMNZAYDZEY-UHFFFAOYSA-N
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Compound 53c
Molecular Weight:297.251
Molecular Formula:C10H10F3NO4S
InChIKey:CTMUNFUTQSRCPK-UHFFFAOYSA-N
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Compound 53d
Molecular Weight:254.262
Molecular Formula:C10H10N2O4S
InChIKey:SYEYLLNIDFNGFB-UHFFFAOYSA-N
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Compound 53e
Molecular Weight:297.251
Molecular Formula:C10H10F3NO4S
InChIKey:VFNLFYQNFJTHIY-UHFFFAOYSA-N
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Compound 53f
Molecular Weight:254.262
Molecular Formula:C10H10N2O4S
InChIKey:KUVAQPQBVKVSER-UHFFFAOYSA-N
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Compound 53g
Molecular Weight:274.251
Molecular Formula:C9H10N2O6S
InChIKey:CNUNSFYNHGATDX-UHFFFAOYSA-N
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Compound 53h
Molecular Weight:243.28
Molecular Formula:C10H13NO4S
InChIKey:MTXHHOSTTMHQHJ-UHFFFAOYSA-N
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Compound 54
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 54a
Molecular Weight:263.698
Molecular Formula:C9H10ClNO4S
InChIKey:LFNRHKSVGLXDLF-UHFFFAOYSA-N
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Compound 54b
Molecular Weight:287.289
Molecular Formula:C11H13NO6S
InChIKey:KTUVPGYKUHEMTR-UHFFFAOYSA-N
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Compound 54c
Molecular Weight:297.251
Molecular Formula:C10H10F3NO4S
InChIKey:ZRHUHGCONIHNSH-UHFFFAOYSA-N
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Compound 54d
Molecular Weight:254.262
Molecular Formula:C10H10N2O4S
InChIKey:XUSPAHFHWIYLCP-UHFFFAOYSA-N
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Compound 54e
Molecular Weight:297.251
Molecular Formula:C10H10F3NO4S
InChIKey:PYPUVONJONMRRZ-UHFFFAOYSA-N
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Compound 54f
Molecular Weight:254.262
Molecular Formula:C10H10N2O4S
InChIKey:IVADUNJYNGOXIW-UHFFFAOYSA-N
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Compound 54g
Molecular Weight:274.251
Molecular Formula:C9H10N2O6S
InChIKey:GUAXMZGYPPUVIW-UHFFFAOYSA-N
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Compound 54h
Molecular Weight:243.28
Molecular Formula:C10H13NO4S
InChIKey:XAKOGFVSONPQLI-UHFFFAOYSA-N
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Compound 45
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 55e
Molecular Weight:137.179
Molecular Formula:C8H11NO
InChIKey:YFVSZHCWKQTSGT-UHFFFAOYSA-N
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Compound 43f
Molecular Weight:269.3383
Molecular Formula:C17H19NO2
InChIKey:LWWBXIKGLAORBQ-UHFFFAOYSA-N
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Compound 43g
Molecular Weight:306.314
Molecular Formula:C14H13NO5S
InChIKey:UOXPZUNAFALTKU-UHFFFAOYSA-M
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Compound 48f
Molecular Weight:210.2346
Molecular Formula:C12H10N4
InChIKey:JMSBEGOMMGKDED-UHFFFAOYSA-N
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Compound 48g
Molecular Weight:252.2713
Molecular Formula:C14H12N4O
InChIKey:ROVZZGOHGUIMGK-UHFFFAOYSA-N
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Compound 56f
Molecular Weight:185.2218
Molecular Formula:C12H11NO
InChIKey:ILGJVPVZCNNBKI-UHFFFAOYSA-N
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Compound 56g
Molecular Weight:227.2585
Molecular Formula:C14H13NO2
InChIKey:USYQPRSFXFKSHI-UHFFFAOYSA-N
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Compound 46f
Molecular Weight:269.3383
Molecular Formula:C17H19NO2
InChIKey:UKTMBKWJXAUWCD-UHFFFAOYSA-N
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Compound 46g
Molecular Weight:306.314
Molecular Formula:C14H13NO5S
InChIKey:RMPDXTPCSCWMIK-UHFFFAOYSA-M
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Compound 50f
Molecular Weight:186.2066
Molecular Formula:C12H10O2
InChIKey:AKRVCGPAANXFME-UHFFFAOYSA-N
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Compound 50g
Molecular Weight:186.2066
Molecular Formula:C12H10O2
InChIKey:AKRVCGPAANXFME-UHFFFAOYSA-N
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Compound 56
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 43i
Molecular Weight:323.3856
Molecular Formula:C20H21NO3
InChIKey:OPQUPQPNJLYMJS-UHFFFAOYSA-N
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Compound 57
Molecular Weight:476.4846
Molecular Formula:C24H24N6O5
InChIKey:WATHXMDHESQEHM-IPMKNSEASA-N
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Compound 59
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 58
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 60
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 61
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 58f
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 58g
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 59f
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 59g
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 60f
Molecular Weight:437.4485
Molecular Formula:C22H23N5O5
InChIKey:ZFAMJVMPZIMXLP-SYDIUPFYSA-N
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Compound 60g
Molecular Weight:477.4693
Molecular Formula:C24H23N5O6
InChIKey:AFXSUQKEWIHMKI-UMCMBGNQSA-N
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Compound 61f
Molecular Weight:434.4479
Molecular Formula:C22H22N6O4
InChIKey:CUJUEJZQRDUDDQ-HPTNYFNFSA-N
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Compound 61g
Molecular Weight:476.4846
Molecular Formula:C24H24N6O5
InChIKey:HZNAZUHXHGGXHZ-RTHHWUBTSA-N
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Compound 39j
Molecular Weight:225.2653
Molecular Formula:C14H13N2O
InChIKey:UFGHOEVTEIKPCF-UHFFFAOYSA-O
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Compound 39j'
Molecular Weight:225.2653
Molecular Formula:C14H13N2O
InChIKey:MQYXWVUHCIRDKM-UHFFFAOYSA-N
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Compound 64j
Molecular Weight:224.2579
Molecular Formula:C14H12N2O
InChIKey:UFGHOEVTEIKPCF-ABUMBURPSA-N
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Compound 50j
Molecular Weight:243.2579
Molecular Formula:C14H13NO3
InChIKey:CJKXJTAPUXLJBY-UHFFFAOYSA-N
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Compound 45j
Molecular Weight:242.2732
Molecular Formula:C14H14N2O2
InChIKey:IXQPZWJQUNHYQR-UHFFFAOYSA-N
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Compound 39k
Molecular Weight:182.2212
Molecular Formula:C12H10N2
InChIKey:OAPDFXXWYYMLSW-UTVYSCCESA-N
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Compound 64k
Molecular Weight:182.2212
Molecular Formula:C12H10N2
InChIKey:OAPDFXXWYYMLSW-UTVYSCCESA-N
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Compound 65k
Molecular Weight:182.2212
Molecular Formula:C12H10N2
InChIKey:OAPDFXXWYYMLSW-UTVYSCCESA-N
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Compound 66a
Molecular Weight:270.3263
Molecular Formula:C16H18N2O2
InChIKey:BRVAHEGGXQBHNS-UHFFFAOYSA-N
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Compound 66b
Molecular Weight:284.3529
Molecular Formula:C17H20N2O2
InChIKey:WZKHOPLXOWJOHU-UHFFFAOYSA-N
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Compound 66c
Molecular Weight:270.3258
Molecular Formula:C16H18N2O2
InChIKey:BXANMCDVPFDTCG-UHFFFAOYSA-N
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Compound 66d
Molecular Weight:284.2701
Molecular Formula:C14H12N4O3
InChIKey:FVESDAATIUPMOB-UHFFFAOYSA-N
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Compound 66e
Molecular Weight:298.2967
Molecular Formula:C15H14N4O3
InChIKey:STIJFDWDZYAECG-UHFFFAOYSA-N
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Compound 66f
Molecular Weight:299.2847
Molecular Formula:C14H13N5O3
InChIKey:UUMMMKKSHUZXRH-UHFFFAOYSA-N
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Compound 66g
Molecular Weight:313.3113
Molecular Formula:C15H15N5O3
InChIKey:YLXJUMYHYJALFF-UHFFFAOYSA-N
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Compound 66h
Molecular Weight:283.3251
Molecular Formula:C16H17N3O2
InChIKey:PEQDJJWOTWFWQO-UHFFFAOYSA-N
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Compound 66i
Molecular Weight:297.3517
Molecular Formula:C17H19N3O2
InChIKey:HSOZYWNPIWJMJS-UHFFFAOYSA-N
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Compound 66I
Molecular Weight:324.377
Molecular Formula:C18H20N4O2
InChIKey:FNDDUQGIQFNCKP-UHFFFAOYSA-N
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Compound 66j
Molecular Weight:285.2979
Molecular Formula:C15H15N3O3
InChIKey:PYLLDVDOUORGQE-UHFFFAOYSA-N
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Compound 66k
Molecular Weight:339.3883
Molecular Formula:C19H21N3O3
InChIKey:HALNWILYIMTMLU-UHFFFAOYSA-N
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Compound 67m
Molecular Weight:208.2187
Molecular Formula:C12H8N4
InChIKey:ZHQUPPKQHPIIBX-UHFFFAOYSA-N
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Compound 67n
Molecular Weight:222.2453
Molecular Formula:C13H10N4
InChIKey:PXJOHKPPZQFUEL-UHFFFAOYSA-N
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Compound 68a
Molecular Weight:169.202
Molecular Formula:C11H9N2
InChIKey:YYHKTIDBSDMRRL-UHFFFAOYSA-N
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Compound 68b
Molecular Weight:183.2286
Molecular Formula:C12H11N2
InChIKey:LYCJAIUNBLRDAJ-UHFFFAOYSA-N
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Compound 68c
Molecular Weight:170.2105
Molecular Formula:C11H10N2
InChIKey:PVBGDCBNIWATFK-UHFFFAOYSA-N
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Compound 68d
Molecular Weight:225.2255
Molecular Formula:C12H9N4O
InChIKey:SQOLPYXLYADDCC-RAXLEYEMSA-N
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Compound 68e
Molecular Weight:239.2521
Molecular Formula:C13H11N4O
InChIKey:SUSADRYRYVJTOZ-KAMYIIQDSA-N
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Compound 68f
Molecular Weight:240.2402
Molecular Formula:C12H10N5O
InChIKey:FXXOZNBXFXLGKK-QINSGFPZSA-N
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Compound 68g
Molecular Weight:254.2667
Molecular Formula:C13H12N5O
InChIKey:OHRDWRRMRLWFNN-SSZFMOIBSA-N
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Compound 68h
Molecular Weight:182.2008
Molecular Formula:C11H7N3
InChIKey:FCHFBFCUMRNSMH-UHFFFAOYSA-O
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Compound 68i
Molecular Weight:196.2274
Molecular Formula:C12H10N3
InChIKey:YOUBIFRJGVJGIY-QBFSEMIESA-N
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Compound 68j
Molecular Weight:224.2375
Molecular Formula:C13H9N3O
InChIKey:WRZZVXBKWSKGRX-OWBHPGMISA-O
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Compound 68k
Molecular Weight:238.264
Molecular Formula:C14H12N3O
InChIKey:SASSVWFBZNPZAI-DTQAZKPQSA-O
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Compound 68l
Molecular Weight:223.2527
Molecular Formula:C13H11N4
InChIKey:FFCOGQACCWGKLD-UHFFFAOYSA-N
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Compound 68m
Molecular Weight:181.2127
Molecular Formula:C12H9N2
InChIKey:HGONOJYEDAADDC-UHFFFAOYSA-O
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Compound 68n
Molecular Weight:195.2393
Molecular Formula:C13H11N2
InChIKey:PJWKBRAAUJKYTP-UHFFFAOYSA-N
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Compound 69f
Molecular Weight:257.248
Molecular Formula:C12H11N5O2
InChIKey:ACYNJLZXBYHHCF-UHFFFAOYSA-N
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Compound 69g
Molecular Weight:271.2746
Molecular Formula:C13H13N5O2
InChIKey:JWLOULMNVGYQSR-UHFFFAOYSA-N
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Compound 70f
Molecular Weight:282.2608
Molecular Formula:C12H10N8O
InChIKey:MGUPFUXAKDABBE-UHFFFAOYSA-N
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Compound 70g
Molecular Weight:296.2874
Molecular Formula:C13H12N8O
InChIKey:RRPOBWUAAGSOTE-UHFFFAOYSA-N
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Compound 71f
Molecular Weight:506.4741
Molecular Formula:C22H22N10O5
InChIKey:DLWHSNZKBPWWPN-BFHYXJOUSA-N
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Compound 71g
Molecular Weight:520.5007
Molecular Formula:C23H24N10O5
InChIKey:DNIGMTGRYWRFPD-RRFJBIMHSA-N
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Compound 72f
Molecular Weight:506.4741
Molecular Formula:C22H22N10O5
InChIKey:HDYILVNOMANWJZ-RDBSUJKOSA-N
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Compound 72g
Molecular Weight:520.5007
Molecular Formula:C23H24N10O5
InChIKey:HZGWAZYKPSNDMO-ILXRZTDVSA-N
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Compound 73h
Molecular Weight:182.2008
Molecular Formula:C11H7N3
InChIKey:FCHFBFCUMRNSMH-UHFFFAOYSA-O
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Compound 73m
Molecular Weight:180.2053
Molecular Formula:C12H8N2
InChIKey:HGONOJYEDAADDC-UHFFFAOYSA-N
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Compound 74
Molecular Weight:226.297
Molecular Formula:C13H10N2S
InChIKey:WKRCOZSCENDENK-UHFFFAOYSA-N
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Compound 75
Molecular Weight:258.314
Molecular Formula:C14H11FN2S
InChIKey:IFWLHIIUGSEKKE-UHFFFAOYSA-N
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Compound 76
Molecular Weight:459.408
Molecular Formula:C20H25Cl2FN4OS
InChIKey:QZSMNTOCJVVFEU-CKUXDGONSA-N
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Compound 77
Molecular Weight:284.333
Molecular Formula:C15H12N2O2S
InChIKey:RYGFGYGUMVTESQ-UHFFFAOYSA-N
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Compound 80
Molecular Weight:243.281
Molecular Formula:C13H9NO2S
InChIKey:SDYBYKXWYDVVKP-UHFFFAOYSA-N
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Compound 79
Molecular Weight:242.296
Molecular Formula:C13H10N2OS
InChIKey:PYLFJPWQQKHRBZ-UHFFFAOYSA-N
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Compound 81
Molecular Weight:267.309
Molecular Formula:C13H9N5S
InChIKey:UUJSTTANRQBQHG-UHFFFAOYSA-N
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Compound 82
Molecular Weight:211.282
Molecular Formula:C13H9NS
InChIKey:XBHOUXSGHYZCNH-UHFFFAOYSA-N
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