You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
StatusDetected and Quantified
Creation Date2006-08-07 17:02:10 UTC
Update Date2020-02-26 21:24:31 UTC
Secondary Accession Numbers
  • HMDB03333
Metabolite Identification
Common Name8-Hydroxy-deoxyguanosine
Description8-Hydroxy-deoxyguanosine, also known as 8-ohdg or 8-oxo-DG, belongs to the class of organic compounds known as purine 2'-deoxyribonucleosides. Purine 2'-deoxyribonucleosides are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 2. 1) small, water-soluble, non-protein-bound compounds, such as urea;. Uremic toxins such as 8-Hydroxy-2Х-deoxyguanosine are actively transported into the kidneys via organic ion transporters (especially OAT3). 8-Hydroxy-deoxyguanosine is a moderately basic compound (based on its pKa). 8-Hydroxy-deoxyguanosine is a potentially toxic compound. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.
8-OHdG compoundHMDB
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 Name8-hydroxy-2'-deoxyguanosine
CAS Registry Number88847-89-6
InChI Identifier
Chemical Taxonomy
Description belongs to the class of organic compounds known as purine 2'-deoxyribonucleosides. Purine 2'-deoxyribonucleosides are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 2.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleosides
Sub ClassPurine 2'-deoxyribonucleosides
Direct ParentPurine 2'-deoxyribonucleosides
Alternative Parents
  • Purine 2'-deoxyribonucleoside
  • Imidazopyrimidine
  • Purine
  • Hydroxypyrimidine
  • N-substituted imidazole
  • Pyrimidine
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Azole
  • Imidazole
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physiological effect

Health effect:


Route of exposure:


Biological location:


Industrial application:

Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility14.8 g/LALOGPS
pKa (Strongest Acidic)10.09ChemAxon
pKa (Strongest Basic)1.59ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area155.22 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity64.56 m³·mol⁻¹ChemAxon
Polarizability25.82 ųChemAxon
Number of Rings3ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9270000000-cbf066db8be0f3462b6dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0006-9503400000-ff14681f666eee936938Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-Ion Trap , Positivesplash10-0a4i-1649170600-b830f720eac21d5be0a6Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-0900000000-bda7c71c752f3e3c4c51Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-279a84bf501a3d5c6555Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-8b53d5aeced1f8b887aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-0900000000-1db539ae30cc3fae45efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0290000000-77880ee90b3d77e9f3f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kf-0920000000-8ab5275c7f1f98f7c143Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dm-4900000000-4c65e34bf57ca440e280Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Nucleus
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • All Tissues
Normal Concentrations
BloodDetected and Quantified0.002 +/- 0.0008 uMAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
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
BloodDetected and Quantified0.0037 +/- 0.00021 uMAdult (>18 years old)Both
Kidney disease
BloodDetected and Quantified0.003 +/- 0.0009 uMAdult (>18 years old)Bothuremia details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Breast cancer
UrineDetected and Quantified0.018 +/- 0.001 umol/mmol creatinineAdult (>18 years old)BothSmoking 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 ]
  1. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
  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 ]
Perillyl alcohol administration for cancer treatment
  1. Woo HM, Kim KM, Choi MH, Jung BH, Lee J, Kong G, Nam SJ, Kim S, Bai SW, Chung BC: Mass spectrometry based metabolomic approaches in urinary biomarker study of women's cancers. Clin Chim Acta. 2009 Feb;400(1-2):63-9. doi: 10.1016/j.cca.2008.10.014. Epub 2008 Oct 30. [PubMed:19010317 ]
Associated OMIM IDsNone
DrugBank IDDB02502
Phenol Explorer Compound IDNot Available
FooDB IDFDB023145
KNApSAcK IDNot Available
Chemspider ID66049
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link8-Oxo-2'-deoxyguanosine
PubChem Compound73318
PDB IDNot Available
ChEBI ID40304
Food Biomarker OntologyNot Available
VMH IDNot Available
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. 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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  21. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]