ENTRY       hsa05204                    Pathway
NAME        Chemical carcinogenesis - DNA adducts - Homo sapiens (human)
DESCRIPTION It has been estimated that exposure to environmental chemical carcinogens may contribute significantly to the causation of a sizable fraction, perhaps a majority, of human cancers. Human carcinogens act through a variety of genotoxic and non-genotoxic mechanisms. Genotoxic carcinogens can attack biological macromolecules such as DNA and RNA either directly or indirectly through metabolism, resulting in the formation of adducts with these macromolecules. If DNA adducts escape cellular repair mechanisms and persist, they may lead to miscoding, resulting in permanent mutations. Mutations cause an undefined number of cell changes, translated into aberrant protein expression and in changes in cell cycle control.
CLASS       Human Diseases; Cancer: overview
PATHWAY_MAP hsa05204  Chemical carcinogenesis - DNA adducts
NETWORK     nt06250  DNA adduct formation
  ELEMENT   N01369  4-ABP to DNA adducts
            N01370  PhIP to DNA adducts
            N01371  PhIP to DNA adducts
            N01372  IQ to DNA adducts
            N01373  MeIQx to DNA adducts
            N01374  BaP to DNA adducts
            N01375  DMBA to DNA adducts
            N01376  Melphalan to DNA adducts/cross-links
            N01377  Thiotepa to DNA adducts/cross-links
            N01378  AFB1 to DNA adducts
            N01379  NNK to DNA adducts
            N01380  NNK to DNA adducts
            N01381  NNK to DNA adducts
            N01382  NNK to DNA adducts
            N01383  NDMA to DNA adducts
            N01384  EO to DNA adducts
            N01385  VC to DNA adducts
            N01386  DCE to DNA adducts
            N01387  SM to DNA adducts/cross-links
ORGANISM    Homo sapiens (human) [GN:hsa]
GENE        10  NAT2; N-acetyltransferase 2 [KO:K00622] [EC:2.3.1.5]
            9  NAT1; N-acetyltransferase 1 [KO:K00622] [EC:2.3.1.5]
            1544  CYP1A2; cytochrome P450 family 1 subfamily A member 2 [KO:K07409] [EC:1.14.14.1]
            6799  SULT1A2; sulfotransferase family 1A member 2 [KO:K01014] [EC:2.8.2.1]
            6817  SULT1A1; sulfotransferase family 1A member 1 [KO:K01014] [EC:2.8.2.1]
            6818  SULT1A3; sulfotransferase family 1A member 3 [KO:K01014] [EC:2.8.2.1]
            445329  SULT1A4; sulfotransferase family 1A member 4 [KO:K01014] [EC:2.8.2.1]
            1543  CYP1A1; cytochrome P450 family 1 subfamily A member 1 [KO:K07408] [EC:1.14.14.1]
            1545  CYP1B1; cytochrome P450 family 1 subfamily B member 1 [KO:K07410] [EC:1.14.14.1]
            1558  CYP2C8; cytochrome P450 family 2 subfamily C member 8 [KO:K17718] [EC:1.14.14.1]
            1559  CYP2C9; cytochrome P450 family 2 subfamily C member 9 [KO:K17719] [EC:1.14.14.51 1.14.14.52 1.14.14.53 1.14.14.-]
            1562  CYP2C18; cytochrome P450 family 2 subfamily C member 18 [KO:K17720] [EC:1.14.14.1]
            1557  CYP2C19; cytochrome P450 family 2 subfamily C member 19 [KO:K17721] [EC:1.14.14.51 1.14.14.52 1.14.14.53 1.14.14.75 1.14.14.-]
            1576  CYP3A4; cytochrome P450 family 3 subfamily A member 4 [KO:K17689] [EC:1.14.13.32 1.14.14.55 1.14.14.56 1.14.14.57 1.14.14.73 1.14.14.-]
            2052  EPHX1; epoxide hydrolase 1 [KO:K01253] [EC:3.3.2.9]
            221357  GSTA5; glutathione S-transferase alpha 5 [KO:K00799] [EC:2.5.1.18]
            2939  GSTA2; glutathione S-transferase alpha 2 [KO:K00799] [EC:2.5.1.18]
            2941  GSTA4; glutathione S-transferase alpha 4 [KO:K00799] [EC:2.5.1.18]
            119391  GSTO2; glutathione S-transferase omega 2 [KO:K00799] [EC:2.5.1.18]
            2948  GSTM4; glutathione S-transferase mu 4 [KO:K00799] [EC:2.5.1.18]
            2953  GSTT2; glutathione S-transferase theta 2 (gene/pseudogene) [KO:K00799] [EC:2.5.1.18]
            2952  GSTT1; glutathione S-transferase theta 1 [KO:K00799] [EC:2.5.1.18]
            2947  GSTM3; glutathione S-transferase mu 3 [KO:K00799] [EC:2.5.1.18]
            4257  MGST1; microsomal glutathione S-transferase 1 [KO:K00799] [EC:2.5.1.18]
            4259  MGST3; microsomal glutathione S-transferase 3 [KO:K00799] [EC:2.5.1.18]
            2944  GSTM1; glutathione S-transferase mu 1 [KO:K00799] [EC:2.5.1.18]
            2949  GSTM5; glutathione S-transferase mu 5 [KO:K00799] [EC:2.5.1.18]
            4258  MGST2; microsomal glutathione S-transferase 2 [KO:K00799] [EC:2.5.1.18]
            2938  GSTA1; glutathione S-transferase alpha 1 [KO:K00799] [EC:2.5.1.18]
            2946  GSTM2; glutathione S-transferase mu 2 [KO:K00799] [EC:2.5.1.18]
            2940  GSTA3; glutathione S-transferase alpha 3 [KO:K00799] [EC:2.5.1.18]
            9446  GSTO1; glutathione S-transferase omega 1 [KO:K00799] [EC:2.5.1.18]
            653689  GSTT2B; glutathione S-transferase theta 2B [KO:K00799] [EC:2.5.1.18]
            2950  GSTP1; glutathione S-transferase pi 1 [KO:K23790] [EC:2.5.1.18]
            373156  GSTK1; glutathione S-transferase kappa 1 [KO:K13299] [EC:2.5.1.18]
            27306  HPGDS; hematopoietic prostaglandin D synthase [KO:K04097] [EC:5.3.99.2 2.5.1.18]
            6822  SULT2A1; sulfotransferase family 2A member 1 [KO:K11822] [EC:2.8.2.14]
            1577  CYP3A5; cytochrome P450 family 3 subfamily A member 5 [KO:K17690] [EC:1.14.14.1]
            1551  CYP3A7; cytochrome P450 family 3 subfamily A member 7 [KO:K17691] [EC:1.14.14.1]
            100861540  CYP3A7-CYP3A51P; CYP3A7-CYP3A51P readthrough [KO:K17691] [EC:1.14.14.1]
            64816  CYP3A43; cytochrome P450 family 3 subfamily A member 43 [KO:K17692] [EC:1.14.14.1]
            5743  PTGS2; prostaglandin-endoperoxide synthase 2 [KO:K11987] [EC:1.14.99.1]
            1548  CYP2A6; cytochrome P450 family 2 subfamily A member 6 [KO:K17683] [EC:1.14.14.-]
            1549  CYP2A7; cytochrome P450 family 2 subfamily A member 7 [KO:K17683] [EC:1.14.14.-]
            1553  CYP2A13; cytochrome P450 family 2 subfamily A member 13 [KO:K17685] [EC:1.14.14.1]
            1646  AKR1C2; aldo-keto reductase family 1 member C2 [KO:K00089] [EC:1.1.1.213 1.1.1.357]
            3290  HSD11B1; hydroxysteroid 11-beta dehydrogenase 1 [KO:K15680] [EC:1.1.1.146]
            374875  HSD11B1L; hydroxysteroid 11-beta dehydrogenase 1 like [KO:K15680] [EC:1.1.1.146]
            873  CBR1; carbonyl reductase 1 [KO:K00079] [EC:1.1.1.184 1.1.1.189 1.1.1.197]
            10941  UGT2A1; UDP glucuronosyltransferase family 2 member A1 complex locus [KO:K00699] [EC:2.4.1.17]
            79799  UGT2A3; UDP glucuronosyltransferase family 2 member A3 [KO:K00699] [EC:2.4.1.17]
            7367  UGT2B17; UDP glucuronosyltransferase family 2 member B17 [KO:K00699] [EC:2.4.1.17]
            10720  UGT2B11; UDP glucuronosyltransferase family 2 member B11 [KO:K00699] [EC:2.4.1.17]
            54490  UGT2B28; UDP glucuronosyltransferase family 2 member B28 [KO:K00699] [EC:2.4.1.17]
            54578  UGT1A6; UDP glucuronosyltransferase family 1 member A6 [KO:K00699] [EC:2.4.1.17]
            54657  UGT1A4; UDP glucuronosyltransferase family 1 member A4 [KO:K00699] [EC:2.4.1.17]
            54658  UGT1A1; UDP glucuronosyltransferase family 1 member A1 [KO:K00699] [EC:2.4.1.17]
            54659  UGT1A3; UDP glucuronosyltransferase family 1 member A3 [KO:K00699] [EC:2.4.1.17]
            7365  UGT2B10; UDP glucuronosyltransferase family 2 member B10 [KO:K00699] [EC:2.4.1.17]
            54600  UGT1A9; UDP glucuronosyltransferase family 1 member A9 [KO:K00699] [EC:2.4.1.17]
            7364  UGT2B7; UDP glucuronosyltransferase family 2 member B7 [KO:K00699] [EC:2.4.1.17]
            54575  UGT1A10; UDP glucuronosyltransferase family 1 member A10 [KO:K00699] [EC:2.4.1.17]
            54576  UGT1A8; UDP glucuronosyltransferase family 1 member A8 [KO:K00699] [EC:2.4.1.17]
            54579  UGT1A5; UDP glucuronosyltransferase family 1 member A5 [KO:K00699] [EC:2.4.1.17]
            7366  UGT2B15; UDP glucuronosyltransferase family 2 member B15 [KO:K00699] [EC:2.4.1.17]
            54577  UGT1A7; UDP glucuronosyltransferase family 1 member A7 [KO:K00699] [EC:2.4.1.17]
            7363  UGT2B4; UDP glucuronosyltransferase family 2 member B4 [KO:K00699] [EC:2.4.1.17]
            574537  UGT2A2; UDP glucuronosyltransferase family 2 member A2 [KO:K00699] [EC:2.4.1.17]
            1571  CYP2E1; cytochrome P450 family 2 subfamily E member 1 [KO:K07415] [EC:1.14.14.-]
COMPOUND    C00027  Hydrogen peroxide
            C03012  Naphthalene-1,2-diol
            C03621  N-Acetoxy-4-aminobiphenyl
            C03622  N-Hydroxy-4-aminobiphenyl
            C06268  Chromium
            C06547  Ethylene
            C06548  Ethylene oxide
            C06752  1,2-Dichloroethane
            C06754  Chloroacetaldehyde
            C06793  Vinyl chloride
            C06800  Aflatoxin B1
            C07122  Melphalan
            C07535  Benzo[a]pyrene
            C07641  Thiotepa
            C10998  4-Aminobiphenyl
            C14556  9-Hydroxybenzo[a]pyrene
            C14704  N-Nitrosodimethylamine
            C14783  1,2-Naphthoquinone
            C14849  Benzo[a]pyrene-9,10-oxide
            C14850  Benzo[a]pyrene-7,8-oxide
            C14851  Benzo[a]pyrene-4,5-oxide
            C14852  Benzo[a]pyrene-7,8-dihydrodiol
            C14853  Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide
            C14854  9-Hydroxybenzo[a]pyrene-4,5-oxide
            C14855  4,5-Dihydro-4-hydroxy-5-S-glutathionyl-benzo[a]pyrene
            C14856  7,8-Dihydro-7-hydroxy-8-S-glutathionyl-benzo[a]pyrene
            C14874  Glutathione episulfonium ion
            C16038  2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine
            C16453  4-(N-Nitrosomethylamino)-1-(3-pyridyl)-1-butanone
            C16844  Hydroxyl radical
            C19164  Sulfur mustard
            C19180  2-Amino-3-methylimidazo[4,5-f]quinoline
            C19255  MeIQx
            C19488  7,12-Dimethylbenz[a]anthracene
            C19489  1a,11b-Dihydro-4,9-dimethylbenz[a]anthra[3,4-b]oxirene
            C19490  trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene
            C19525  Sudan I
            C19559  (1aalpha,2beta,3alpha,11calpha)-1a,2,3,11c-Tetrahydro-6,11-dimethylbenzo[6,7]phenanthro[3,4-b]oxirene-2,3-diol
            C19561  7-Hydroxymethyl-12-methylbenz[a]anthracene
            C19562  7-Hydroxymethyl-12-methylbenz[a]anthracene sulfate
            C19563  4-[(Hydroxymethyl)nitrosoamino]-1-(3-pyridinyl)-1-butanone
            C19564  4-(Nitrosoamino)-1-(3-pyridinyl)-1-butanone
            C19565  4-Hydroxy-1-(3-pyridinyl)-1-butanone
            C19566  4-Hydroxy-4-(methylnitrosoamino)-1-(3-pyridinyl)-1-butanone
            C19567  4-Oxo-1-(3-pyridyl)-1-butanone
            C19568  N-Nitrosomethanamine
            C19569  3-Succinoylpyridine
            C19574  4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol
            C19577  1-(Methylnitrosoamino)-4-(3-pyridinyl)-1,4-butanediol
            C19578  5-(3-Pyridyl)-2-hydroxytetrahydrofuran
            C19579  gamma-Hydroxy-3-pyridinebutanoate
            C19580  alpha-[3-[(Hydroxymethyl)nitrosoamino]propyl]-3-pyridinemethanol
            C19581  alpha-[3-(Nitrosoamino)propyl]-3-pyridinemethanol
            C19582  1-(3-Pyridinyl)-1,4-butanediol
            C19586  Aflatoxin B1-exo-8,9-epoxide
            C19602  4-(Methylnitrosamino)-1-(1-oxido-3-pyridinyl)-1-butanone
            C19603  4-(Methylnitrosamino)-1-(3-pyridyl-N-oxide)-1-butanol
            C19605  4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol glucuronide
            C19606  NNAL-N-glucuronide
            C20280  1-Phenylazo-2,6-dihydroxynaphthalene
            C20281  1-(4-Hydroxyphenylazo)-2-naphthol
            C20282  1-(4-Hydroxyphenylazo)-naphthalene-2,6-diol
            C20283  1-(3,4-Dihydroxyphenylazo)-2-naphthol
            C20284  Benzenediazonium
            C20285  4-Acetylaminobiphenyl
            C20286  2-Hydroxyamino-1-methyl-6-phenylimidazo[4,5-b]pyridine
            C20287  2-Acetoxyamino-1-methyl-6-phenylimidazo[4,5-b]pyridine
            C20288  N-Sulfonyloxy-PhIP
            C20289  N-Hydroxy-IQ
            C20290  N-Acetoxy-IQ
            C20291  N-Hydroxy-MeIQx
            C20293  N-Acetoxy-MeIQx
            C20301  alpha-Hydroxy-NDMA
            C20302  Methyldiazonium ion
            C20303  Chloroethylene oxide
            C20304  S-(2-Chloroethyl)glutathione
            C20305  1,2-Dichloroethanol
            C20306  Methyldiazohydroxide
REFERENCE   PMID:15660110
  AUTHORS   Luch A.
  TITLE     Nature and nurture - lessons from chemical carcinogenesis.
  JOURNAL   Nat Rev Cancer 5:113-25 (2005)
            DOI:10.1038/nrc1546
REFERENCE   PMID:14570033
  AUTHORS   Hecht SS
  TITLE     Tobacco carcinogens, their biomarkers and tobacco-induced cancer.
  JOURNAL   Nat Rev Cancer 3:733-44 (2003)
            DOI:10.1038/nrc1190
REFERENCE   PMID:18066431
  AUTHORS   Oliveira PA, Colaco A, Chaves R, Guedes-Pinto H, De-La-Cruz P LF, Lopes C
  TITLE     Chemical carcinogenesis.
  JOURNAL   An Acad Bras Cienc 79:593-616 (2007)
            DOI:10.1590/S0001-37652007000400004
REFERENCE   PMID:15489140
  AUTHORS   Wogan GN, Hecht SS, Felton JS, Conney AH, Loeb LA.
  TITLE     Environmental and chemical carcinogenesis.
  JOURNAL   Semin Cancer Biol 14:473-86 (2004)
            DOI:10.1016/j.semcancer.2004.06.010
REFERENCE   PMID:21234336
  AUTHORS   Hang B
  TITLE     Formation and repair of tobacco carcinogen-derived bulky DNA adducts.
  JOURNAL   J Nucleic Acids 2010:709521 (2010)
            DOI:10.4061/2010/709521
REFERENCE   PMID:12928348
  AUTHORS   Tsuneoka Y, Dalton TP, Miller ML, Clay CD, Shertzer HG, Talaska G, Medvedovic M, Nebert DW
  TITLE     4-aminobiphenyl-induced liver and urinary bladder DNA adduct formation in Cyp1a2(-/-) and Cyp1a2(+/+) mice.
  JOURNAL   J Natl Cancer Inst 95:1227-37 (2003)
            DOI:10.1093/jnci/djg025
REFERENCE   PMID:11978484
  AUTHORS   Kawanishi S, Hiraku Y, Murata M, Oikawa S
  TITLE     The role of metals in site-specific DNA damage with reference to carcinogenesis.
  JOURNAL   Free Radic Biol Med 32:822-32 (2002)
            DOI:10.1016/S0891-5849(02)00779-7
REFERENCE   PMID:20232918
  AUTHORS   Patterson AD, Gonzalez FJ, Idle JR
  TITLE     Xenobiotic metabolism: a view through the metabolometer.
  JOURNAL   Chem Res Toxicol 23:851-60 (2010)
            DOI:10.1021/tx100020p
REFERENCE   PMID:9202760
  AUTHORS   Turesky RJ, Box RM, Markovic J, Gremaud E, Snyderwine EG
  TITLE     Formation and persistence of DNA adducts of 2-amino-3-methylimidazo[4,5-f]quinoline in the rat and nonhuman primates.
  JOURNAL   Mutat Res 376:235-41 (1997)
            DOI:10.1016/S0027-5107(97)00048-1
REFERENCE   PMID:20570348
  AUTHORS   Immonen E, Kummu M, Petsalo A, Pihlaja T, Mathiesen L, Nielsen JK, Knudsen LE, Vahakangas K, Myllynen P
  TITLE     Toxicokinetics of the food-toxin IQ in human placental perfusion is not affected by ABCG2 or xenobiotic metabolism.
  JOURNAL   Placenta 31:641-8 (2010)
            DOI:10.1016/j.placenta.2010.05.002
REFERENCE   PMID:8702479
  AUTHORS   Solomon MS, Morgenthaler PM, Turesky RJ, Essigmann JM
  TITLE     Mutational and DNA binding specificity of the carcinogen 2-amino-3, 8-dimethylimidazo[4,5-f]quinoxaline.
  JOURNAL   J Biol Chem 271:18368-74 (1996)
            DOI:10.1074/jbc.271.31.18368
REFERENCE   PMID:21456541
  AUTHORS   Nauwelaers G, Bessette EE, Gu D, Tang Y, Rageul J, Fessard V, Yuan JM, Yu MC, Langouet S, Turesky RJ
  TITLE     DNA adduct formation of 4-aminobiphenyl and heterocyclic aromatic amines in human hepatocytes.
  JOURNAL   Chem Res Toxicol 24:913-25 (2011)
            DOI:10.1021/tx200091y
REFERENCE   PMID:20669524
  AUTHORS   
  TITLE     The Health Consequences of Involuntary Exposure to Tobacco Smoke: A Report of the Surgeon General.
  JOURNAL   The Health Consequences of Involuntary Exposure to Tobacco Smoke: A Report of the  (2006)
REFERENCE   PMID:17445838
  AUTHORS   Singh R, Sram RJ, Binkova B, Kalina I, Popov TA, Georgieva T, Garte S, Taioli E, Farmer PB
  TITLE     The relationship between biomarkers of oxidative DNA damage, polycyclic aromatic hydrocarbon DNA adducts, antioxidant status and genetic susceptibility following exposure to environmental air pollution in humans.
  JOURNAL   Mutat Res 620:83-92 (2007)
            DOI:10.1016/j.mrfmmm.2007.02.025
REFERENCE   PMID:15298956
  AUTHORS   Lodovici M, Luceri C, Guglielmi F, Bacci C, Akpan V, Fonnesu ML, Boddi V, Dolara P.
  TITLE     Benzo(a)pyrene diolepoxide (BPDE)-DNA adduct levels in leukocytes of smokers in relation to polymorphism of CYP1A1, GSTM1, GSTP1, GSTT1, and mEH.
  JOURNAL   Cancer Epidemiol Biomarkers Prev 13:1342-8 (2004)
REFERENCE   PMID:19531241
  AUTHORS   Androutsopoulos VP, Tsatsakis AM, Spandidos DA
  TITLE     Cytochrome P450 CYP1A1: wider roles in cancer progression and prevention.
  JOURNAL   BMC Cancer 9:187 (2009)
            DOI:10.1186/1471-2407-9-187
REFERENCE   PMID:11376689
  AUTHORS   Gonzalez FJ, Kimura S
  TITLE     Understanding the role of xenobiotic-metabolism in chemical carcinogenesis using gene knockout mice.
  JOURNAL   Mutat Res 477:79-87 (2001)
            DOI:10.1016/S0027-5107(01)00109-9
REFERENCE   PMID:11467078
  AUTHORS   Banoglu E
  TITLE     Current status of the cytosolic sulfotransferases in the metabolic activation of promutagens and procarcinogens.
  JOURNAL   Curr Drug Metab 1:1-30 (2000)
            DOI:10.2174/1389200003339234
REFERENCE   PMID:15532073
  AUTHORS   Lehner AF, Horn J, Flesher JW
  TITLE     Mass spectrometric analysis of 7-sulfoxymethyl-12-methylbenz[a]anthracene and related electrophilic polycyclic aromatic hydrocarbon metabolites.
  JOURNAL   J Mass Spectrom 39:1366-78 (2004)
            DOI:10.1002/jms.730
REFERENCE   PMID:21217854
  AUTHORS   Stiborova M, Martinek V, Semanska M, Hodek P, Dracinsky M, Cvacka J, Schmeiser HH, Frei E
  TITLE     Oxidation of the carcinogenic non-aminoazo dye 1-phenylazo-2-hydroxy-naphthalene (Sudan I) by cytochromes P450 and peroxidases: a comparative study.
  JOURNAL   Interdiscip Toxicol 2:195-200 (2009)
            DOI:10.2478/v10102-009-0017-z
REFERENCE   PMID:10913381
  AUTHORS   Maanen MJ, Smeets CJ, Beijnen JH
  TITLE     Chemistry, pharmacology and pharmacokinetics of N,N',N" -triethylenethiophosphoramide (ThioTEPA).
  JOURNAL   Cancer Treat Rev 26:257-68 (2000)
            DOI:10.1053/ctrv.2000.0170
REFERENCE   PMID:11092599
  AUTHORS   Hoes I, Van Dongen W, Lemiere F, Esmans EL, Van Bockstaele D, Berneman ZN
  TITLE     Comparison between capillary and nano liquid chromatography-electrospray mass spectrometry for the analysis of minor DNA-melphalan adducts.
  JOURNAL   J Chromatogr B Biomed Sci Appl 748:197-212 (2000)
            DOI:10.1016/S0378-4347(00)00400-X
REFERENCE   PMID:22705365
  AUTHORS   Lee JC, Son YO, Pratheeshkumar P, Shi X
  TITLE     Oxidative stress and metal carcinogenesis.
  JOURNAL   Free Radic Biol Med 53:742-57 (2012)
            DOI:10.1016/j.freeradbiomed.2012.06.002
REFERENCE   PMID:12435844
  AUTHORS   Wild CP, Turner PC
  TITLE     The toxicology of aflatoxins as a basis for public health decisions.
  JOURNAL   Mutagenesis 17:471-81 (2002)
            DOI:10.1093/mutage/17.6.471
REFERENCE   PMID:9275165
  AUTHORS   Kobertz WR, Wang D, Wogan GN, Essigmann JM
  TITLE     An intercalation inhibitor altering the target selectivity of DNA damaging agents: synthesis of site-specific aflatoxin B1 adducts in a p53 mutational hotspot.
  JOURNAL   Proc Natl Acad Sci U S A 94:9579-84 (1997)
            DOI:10.1073/pnas.94.18.9579
REFERENCE   PMID:8759017
  AUTHORS   Bailey EA, Iyer RS, Harris TM, Essigmann JM
  TITLE     A viral genome containing an unstable aflatoxin B1-N7-guanine DNA adduct situated at a unique site.
  JOURNAL   Nucleic Acids Res 24:2821-8 (1996)
            DOI:10.1093/nar/24.14.2821
REFERENCE   PMID:21473878
  AUTHORS   Chiang HC, Wang CY, Lee HL, Tsou TC
  TITLE     Metabolic effects of CYP2A6 and CYP2A13 on 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK)-induced gene mutation--a mammalian cell-based mutagenesis approach.
  JOURNAL   Toxicol Appl Pharmacol 253:145-52 (2011)
            DOI:10.1016/j.taap.2011.03.022
REFERENCE   PMID:21154658
  AUTHORS   Bhat SH, Gelhaus SL, Mesaros C, Vachani A, Blair IA
  TITLE     A new liquid chromatography/mass spectrometry method for 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) in urine.
  JOURNAL   Rapid Commun Mass Spectrom 25:115-21 (2011)
            DOI:10.1002/rcm.4824
REFERENCE   PMID:20159989
  AUTHORS   Maertens LA, Upadhyaya P, Hecht SS, Zimmerman CL
  TITLE     Formation and distribution of NNK metabolites in an isolated perfused rat lung.
  JOURNAL   Drug Metab Dispos 38:752-60 (2010)
            DOI:10.1124/dmd.109.031492
REFERENCE   PMID:8951235
  AUTHORS   Lee VM, Keefer LK, Archer MC
  TITLE     An evaluation of the roles of metabolic denitrosation and alpha-hydroxylation in the hepatotoxicity of N-Nitrosodimethylamine.
  JOURNAL   Chem Res Toxicol 9:1319-24 (1996)
            DOI:10.1021/tx960077u
REFERENCE   PMID:21163908
  AUTHORS   Swenberg JA, Lu K, Moeller BC, Gao L, Upton PB, Nakamura J, Starr TB
  TITLE     Endogenous versus exogenous DNA adducts: their role in carcinogenesis, epidemiology, and risk assessment.
  JOURNAL   Toxicol Sci 120 Suppl 1:S130-45 (2011)
            DOI:10.1093/toxsci/kfq371
REFERENCE   PMID:10753215
  AUTHORS   Yang Y, Nair J, Barbin A, Bartsch H
  TITLE     Immunohistochemical detection of 1,N(6)-ethenodeoxyadenosine, a promutagenic DNA adduct, in liver of rats exposed to vinyl chloride or an iron overload.
  JOURNAL   Carcinogenesis 21:777-81 (2000)
            DOI:10.1093/carcin/21.4.777
REFERENCE   PMID:15582261
  AUTHORS   Bartsch H, Nair J
  TITLE     Oxidative stress and lipid peroxidation-derived DNA-lesions in inflammation driven carcinogenesis.
  JOURNAL   Cancer Detect Prev 28:385-91 (2004)
            DOI:10.1016/j.cdp.2004.07.004
REFERENCE   PMID:16084004
  AUTHORS   Kehe K, Szinicz L
  TITLE     Medical aspects of sulphur mustard poisoning.
  JOURNAL   Toxicology 214:198-209 (2005)
            DOI:10.1016/j.tox.2005.06.014
REFERENCE   PMID:17292678
  AUTHORS   Matijasevic Z, Volkert MR
  TITLE     Base excision repair sensitizes cells to sulfur mustard and chloroethyl ethyl sulfide.
  JOURNAL   DNA Repair (Amst) 6:733-41 (2007)
            DOI:10.1016/j.dnarep.2006.12.014
REL_PATHWAY hsa00980  Metabolism of xenobiotics by cytochrome P450
            hsa05210  Colorectal cancer
            hsa05211  Renal cell carcinoma
            hsa05215  Prostate cancer
            hsa05219  Bladder cancer
            hsa05221  Acute myeloid leukemia
            hsa05222  Small cell lung cancer
            hsa05223  Non-small cell lung cancer
            hsa05224  Breast cancer
            hsa05225  Hepatocellular carcinoma
            hsa05226  Gastric cancer
KO_PATHWAY  ko05204
///
