Human Metabolome Database Version 3.5

Showing metabocard for 8-Hydroxy-deoxyguanosine (HMDB03333)

Record Information
Version 3.5
Creation Date 2006-08-07 11:02:10 -0600
Update Date 2013-02-08 17:12:26 -0700
HMDB ID HMDB03333
Secondary Accession Numbers None
Metabolite Identification
Common Name 8-Hydroxy-deoxyguanosine
Description 8-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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C10H13N5O5
Average Molecular Weight 283.2407
Monoisotopic Molecular Weight 283.091668551
IUPAC Name 2-amino-8-hydroxy-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one
Traditional IUPAC Name 8-hydroxydeoxyguanosine
CAS Registry Number 88847-89-6
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 Key HCAJQHYUCKICQH-VPENINKCSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Nucleosides, Nucleotides, and Analogues
Class Purine Nucleosides and Analogues
Sub Class Purine 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 Parent Purine 2'-deoxyribonucleosides and Analogues
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm
  • Nucleus
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 14.8 g/L ALOGPS
LogP -1.71 ALOGPS
LogP -1.4 ChemAxon
LogS -1.28 ALOGPS
pKa (strongest acidic) 10.09 ChemAxon
pKa (strongest basic) 1.59 ChemAxon
Hydrogen Acceptor Count 8 ChemAxon
Hydrogen Donor Count 5 ChemAxon
Polar Surface Area 155.22 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 64.56 ChemAxon
Polarizability 25.82 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Nucleus
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • All Tissues
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Urine Detected and Quantified
0.018 +/- 0.001 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.0063 +/- 0.0005 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.0015 (0.00055-0.0024) umol/mmol creatinine Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 0.0037 +/- 0.00021 uM Adult (>18 years old) Both Comment Kidney disease
Associated Disorders and Diseases
Disease References
Kidney disease
  • 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 Link_out
      Smoking
      • 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 Link_out
          Associated OMIM IDs None
          DrugBank ID Not Available
          DrugBank Metabolite ID Not Available
          Phenol Explorer Compound ID Not Available
          Phenol Explorer Metabolite ID Not Available
          FoodDB ID FDB023145
          KNApSAcK ID Not Available
          Chemspider ID 66049 Link_out
          KEGG Compound ID Not Available
          BioCyc ID Not Available
          BiGG ID Not Available
          Wikipedia Link Not Available
          NuGOwiki Link HMDB03333 Link_out
          Metagene Link HMDB03333 Link_out
          METLIN ID 6890 Link_out
          PubChem Compound 73318 Link_out
          PDB ID 8HG Link_out
          ChEBI ID 40304 Link_out
          References
          Synthesis Reference Kawamoto 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. 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 Link_out
          2. 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 Link_out
          3. 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 Link_out
          4. 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 Link_out
          5. 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 Link_out
          6. 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 Link_out
          7. 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 Link_out
          8. 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 Link_out
          9. 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 Link_out
          10. 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 Link_out
          11. 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 Link_out
          12. 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 Link_out
          13. 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 Link_out
          14. 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 Link_out
          15. 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 Link_out
          16. 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 Link_out
          17. 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 Link_out
          18. 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 Link_out
          19. 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 Link_out
          20. 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 Link_out