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Record Information
Version3.6
Creation Date2006-08-07 17:02:10 UTC
Update Date2013-02-09 00:12:26 UTC
HMDB IDHMDB03333
Secondary Accession NumbersNone
Metabolite Identification
Common Name8-Hydroxy-deoxyguanosine
Description8-hydroxy-deoxyguanosine (8-OHdG) is a sensitive marker of the DNA damage due to hydroxyl radical attack at the C8 of guanine. This damage, if left unrepaired, has been proposed to contribute to mutagenicity and cancer promotion.
Structure
Thumb
Synonyms
  1. 7,8-Dihydro-8-oxo-2'-deoxyguanosine
  2. 7,8-Dihydro-8-oxodeoxyguanosine
  3. 8-Hydroxy-2'-deoxyguanosine
  4. 8-Hydroxy-2'deoxyguanosine
  5. 8-Hydroxy-2-deoxyguanosine
  6. 8-Hydroxydeoxy-guanosine
  7. 8-Hydroxydeoxyguanine
  8. 8-Hydroxydeoxyguanosine
  9. 8-OHdG
  10. 8-Oxo-7,8-dihydro-2'-deoxyguanosine
  11. 8-Oxo-7,8-dihydrodeoxyguanosine
  12. 8-Oxo-dG
  13. 8-Oxodg
  14. Oh8dG
Chemical FormulaC10H13N5O5
Average Molecular Weight283.2407
Monoisotopic Molecular Weight283.091668551
IUPAC Name2-amino-8-hydroxy-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one
Traditional IUPAC Name8-hydroxydeoxyguanosine
CAS Registry Number88847-89-6
SMILES
NC1=NC2=C(N=C(O)N2[C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)N1
InChI Identifier
InChI=1S/C10H13N5O5/c11-9-13-7-6(8(18)14-9)12-10(19)15(7)5-1-3(17)4(2-16)20-5/h3-5,16-17H,1-2H2,(H,12,19)(H3,11,13,14,18)/t3-,4+,5+/m0/s1
InChI KeyHCAJQHYUCKICQH-VPENINKCSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassNucleosides, Nucleotides, and Analogues
ClassPurine Nucleosides and Analogues
Sub ClassPurine 2'-deoxyribonucleosides and Analogues
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • guanosines(ChEBI)
Substituents
  • Aminopyrimidine
  • Hypoxanthine
  • Imidazole
  • Imidazopyrimidine
  • Oxolane
  • Primary Alcohol
  • Purine
  • Purinone
  • Pyrimidine
  • Pyrimidone
  • Secondary Alcohol
Direct ParentPurine 2'-deoxyribonucleosides and Analogues
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Nucleus
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility14.8 g/LALOGPS
logP-1.7ALOGPS
logP-1.4ChemAxon
logS-1.3ALOGPS
pKa (strongest acidic)10.09ChemAxon
pKa (strongest basic)1.59ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count8ChemAxon
hydrogen donor count5ChemAxon
polar surface area155.22ChemAxon
rotatable bond count2ChemAxon
refractivity64.56ChemAxon
polarizability25.82ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Nucleus
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • All Tissues
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.018 +/- 0.001 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0063 +/- 0.0005 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0015 (0.00055-0.0024) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0037 +/- 0.00021 uMAdult (>18 years old)Both
Kidney disease
details
Associated Disorders and Diseases
Disease References
Kidney disease
  1. Stenvinkel P, Rodriguez-Ayala E, Massy ZA, Qureshi AR, Barany P, Fellstrom B, Heimburger O, Lindholm B, Alvestrand A: Statin treatment and diabetes affect myeloperoxidase activity in maintenance hemodialysis patients. Clin J Am Soc Nephrol. 2006 Mar;1(2):281-7. Epub 2006 Feb 1. Pubmed: 17699218
Smoking
  1. Li N, Jia X, Chen CY, Blumberg JB, Song Y, Zhang W, Zhang X, Ma G, Chen J: Almond consumption reduces oxidative DNA damage and lipid peroxidation in male smokers. J Nutr. 2007 Dec;137(12):2717-22. Pubmed: 18029489
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023145
KNApSAcK IDNot Available
Chemspider ID66049
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB03333
Metagene LinkHMDB03333
METLIN ID6890
PubChem Compound73318
PDB ID8HG
ChEBI ID40304
References
Synthesis ReferenceKawamoto T; Ikeuchi Y; Mikata Y; Kishigami M K; Yano S; Murayama C; Mori T; Yoneda F Promotion of radiation-induced formation of 8-oxo-7,8-dihydro-2'-deoxyguanosine by nitro 5-deazaflavin derivatives. Bioorganic & medicinal chemistry letters (2001), 11(13), 1745-8.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Xu D, Ong C, Shen H: [The associations between concentration of selenium in semen and sperm parameters as well as oxidative DNA damage in human sperm] Zhonghua Yu Fang Yi Xue Za Zhi. 2001 Nov;35(6):394-6. Pubmed: 11840768
  2. Tarng DC, Huang TP, Wei YH, Liu TY, Chen HW, Wen Chen T, Yang WC: 8-hydroxy-2'-deoxyguanosine of leukocyte DNA as a marker of oxidative stress in chronic hemodialysis patients. Am J Kidney Dis. 2000 Nov;36(5):934-44. Pubmed: 11054349
  3. Sumida S, Doi T, Sakurai M, Yoshioka Y, Okamura K: Effect of a single bout of exercise and beta-carotene supplementation on the urinary excretion of 8-hydroxy-deoxyguanosine in humans. Free Radic Res. 1997 Dec;27(6):607-18. Pubmed: 9455696
  4. Takane M, Sugano N, Iwasaki H, Iwano Y, Shimizu N, Ito K: New biomarker evidence of oxidative DNA damage in whole saliva from clinically healthy and periodontally diseased individuals. J Periodontol. 2002 May;73(5):551-4. Pubmed: 12027259
  5. Shen HM, Chia SE, Ni ZY, New AL, Lee BL, Ong CN: Detection of oxidative DNA damage in human sperm and the association with cigarette smoking. Reprod Toxicol. 1997 Sep-Oct;11(5):675-80. Pubmed: 9311575
  6. Farinati F, Cardin R, Degan P, De Maria N, Floyd RA, Van Thiel DH, Naccarato R: Oxidative DNA damage in circulating leukocytes occurs as an early event in chronic HCV infection. Free Radic Biol Med. 1999 Dec;27(11-12):1284-91. Pubmed: 10641722
  7. Lagorio S, Tagesson C, Forastiere F, Iavarone I, Axelson O, Carere A: Exposure to benzene and urinary concentrations of 8-hydroxydeoxyguanosine, a biological marker of oxidative damage to DNA. Occup Environ Med. 1994 Nov;51(11):739-43. Pubmed: 7849850
  8. Okamura K, Doi T, Hamada K, Sakurai M, Yoshioka Y, Mitsuzono R, Migita T, Sumida S, Sugawa-Katayama Y: Effect of repeated exercise on urinary 8-hydroxy-deoxyguanosine excretion in humans. Free Radic Res. 1997 Jun;26(6):507-14. Pubmed: 9212344
  9. Ni ZY, Liu YQ, Shen HM, Chia SE, Ong CN: Does the increase of 8-hydroxydeoxyguanosine lead to poor sperm quality? Mutat Res. 1997 Nov 19;381(1):77-82. Pubmed: 9403033
  10. Mitsui T, Umaki Y, Nagasawa M, Akaike M, Ohtsuka S, Odomi M, Aki K, Matsumoto T: Motor neuron involvement in a patient with long-term corticosteroid administration. Intern Med. 2003 Sep;42(9):862-6. Pubmed: 14518677
  11. Bergman V, Leanderson P, Starkhammar H, Tagesson C: Urinary excretion of 8-hydroxydeoxyguanosine and malondialdehyde after high dose radiochemotherapy preceding stem cell transplantation. Free Radic Biol Med. 2004 Feb 1;36(3):300-6. Pubmed: 15036349
  12. Wakai K, Ando M, Ozasa K, Ito Y, Suzuki K, Nishino Y, Kuriyama S, Seki N, Kondo T, Watanabe Y, Ohno Y, Tamakoshi A: Updated information on risk factors for lung cancer: findings from the JACC Study. J Epidemiol. 2005 Jun;15 Suppl 2:S134-9. Pubmed: 16127225
  13. Tarng DC, Huang TP, Liu TY, Chen HW, Sung YJ, Wei YH: Effect of vitamin E-bonded membrane on the 8-hydroxy 2'-deoxyguanosine level in leukocyte DNA of hemodialysis patients. Kidney Int. 2000 Aug;58(2):790-9. Pubmed: 10916104
  14. Kitada T, Seki S, Iwai S, Yamada T, Sakaguchi H, Wakasa K: In situ detection of oxidative DNA damage, 8-hydroxydeoxyguanosine, in chronic human liver disease. J Hepatol. 2001 Nov;35(5):613-8. Pubmed: 11690707
  15. Schmidt MC, Askew EW, Roberts DE, Prior RL, Ensign WY Jr, Hesslink RE Jr: Oxidative stress in humans training in a cold, moderate altitude environment and their response to a phytochemical antioxidant supplement. Wilderness Environ Med. 2002 Summer;13(2):94-105. Pubmed: 12092978
  16. Sabatini L, Barbieri A, Tosi M, Roda A, Violante FS: A method for routine quantitation of urinary 8-hydroxy-2'-deoxyguanosine based on solid-phase extraction and micro-high-performance liquid chromatography/electrospray ionization tandem mass spectrometry. Rapid Commun Mass Spectrom. 2005;19(2):147-52. Pubmed: 15593068
  17. Sumida S, Okamura K, Doi T, Sakurai M, Yoshioka Y, Sugawa-Katayama Y: No influence of a single bout of exercise on urinary excretion of 8-hydroxy-deoxyguanosine in humans. Biochem Mol Biol Int. 1997 Jul;42(3):601-9. Pubmed: 9247718
  18. Sugano N, Yokoyama K, Oshikawa M, Kumagai K, Takane M, Tanaka H, Ito K: Detection of Streptococcus anginosus and 8-hydroxydeoxyguanosine in saliva. J Oral Sci. 2003 Dec;45(4):181-4. Pubmed: 14763512
  19. Leighton F, Cuevas A, Guasch V, Perez DD, Strobel P, San Martin A, Urzua U, Diez MS, Foncea R, Castillo O, Mizon C, Espinoza MA, Urquiaga I, Rozowski J, Maiz A, Germain A: Plasma polyphenols and antioxidants, oxidative DNA damage and endothelial function in a diet and wine intervention study in humans. Drugs Exp Clin Res. 1999;25(2-3):133-41. Pubmed: 10370876
  20. Xu DX, Shen HM, Zhu QX, Chua L, Wang QN, Chia SE, Ong CN: The associations among semen quality, oxidative DNA damage in human spermatozoa and concentrations of cadmium, lead and selenium in seminal plasma. Mutat Res. 2003 Jan 10;534(1-2):155-63. Pubmed: 12504764