MiMeDB: Showing metabocard for Deoxyguanosine (MMDBc0029470)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:23:35 UTC

Update Date

2022-08-31 08:42:59 UTC

MiMeDB ID

MMDBc0029470

Metabolite Identification

Common Name

Deoxyguanosine

Description

Deoxyguanosine is a nucleoside consisting of the base guanine and the sugar deoxyribose. It is like guanosine, but with one oxygen atom removed. It is a nucleoside component of DNA. Deoxyguanosine can be converted to 8-hydroxy-deoxyguanosine (8-OHdG) due to hydroxyl radical attack at the C8 of guanine. 8-OHdG is a sensitive marker of the DNA damage This damage, if left unrepaired, has been proposed to contribute to mutagenicity and cancer promotion.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₁₀H₁₃N₅O₄

Average Molecular Weight

267.2413

Monoisotopic Molecular Weight

267.096753929

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

961-07-9

SMILES

Not Available

InChI Identifier

InChI=1S/C10H13N5O4/c11-10-13-8-7(9(18)14-10)12-3-15(8)6-1-4(17)5(2-16)19-6/h3-6,16-17H,1-2H2,(H3,11,13,14,18)/t4-,5+,6+/m0/s1

InChI Key

YKBGVTZYEHREMT-KVQBGUIXSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Lysosome
Mitochondria
Nucleus

Biospecimen Locations

All Tissues
Blood
Feces
Saliva
Urine

Tissue Locations

All Tissues

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Proteins

#<MetaboliteProteinLink:0x0000564abb985970>

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference
Purine nucleoside phosphorylase deficiency		This associated disease is originally imported from HMDB metabolite HMDB0000085 concentration id 17126	Association	Human Blood		16131572	details
Purine nucleoside phosphorylase deficiency	Increased	This associated disease is originally imported from HMDB metabolite HMDB0000085 concentration id 912	Association	Human Urine		10102915	details

Microbial Sources

Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
	Proteobacteria	322	Human Feces; Human ; Pig	Unknown; Metabolic reconstruction;
	Firmicutes	569	Human Feces; Pig ; Human ; Cattle	Metabolic reconstruction
	Actinobacteria	159	Human Feces; Human	Metabolic reconstruction
	Verrucomicrobia	2	Human	Metabolic reconstruction
	Bacteroidetes	241	Human Feces; Human	Metabolic reconstruction
	Synergistetes	5	Human Feces	Metabolic reconstruction
	Spirochaetes	1	Human Feces	Metabolic reconstruction
	Thaumarchaeota	2	Human Feces	Metabolic reconstruction
	Fusobacteria	29	Human Feces; Human	Metabolic reconstruction
	Candidatus Melainabacteria	2	Human Feces	Metabolic reconstruction
	Euryarchaeota	6	Cattle ; Human Feces; Human	Metabolic reconstruction
	Tenericutes	5	Human Feces	Metabolic reconstruction
	Planctomycetes	1	Human Feces	Metabolic reconstruction
	Crenarchaeota	1	Human Feces	Metabolic reconstruction
Fungi	Ascomycota	1	Human Feces	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Min	Max	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB		details
Human	Detected and Quantified	11.0	2.0	20.0	Adult (>18 years old)	Both	Purine nucleoside phosphorylase (PNP) deficiency	HMDB	16131572	details
Human	Detected and Quantified		177.0	322.0	Adult (>18 years old)	Not Specified	Purine nucleoside phosphorylase (PNP) deficiency	HMDB	10102915	details
Human	Detected and Quantified	<0.1			Infant (0-1 year old)	Both	Normal	HMDB	30817767	details
Human	Detected and Quantified	<1.0			Adult (>18 years old)	Not Specified	Normal	HMDB	10102915	details
Human	Detected and Quantified	1.00	0.00	2.00	Adult (>18 years old)	Both	Normal	HMDB	16613999	details
Human	Detected and Quantified		0	5	Children (1 - 18 years old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab	details
Human	Detected and Quantified	0			Children (1 - 13 years old)	Both	Normal	HMDB	Physician's Guide to the Laboratory Diagnosis of Metabolic Diseases. 2nd ed. Berlin, Germany, Springer, 2003	details
Human All Tissues	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597	details
Human Saliva	Detected but not Quantified				Adult (>18 years old)	Male	Normal	HMDB	22308371	details
Human Saliva	Detected but not Quantified				Adult (>18 years old)	Male	Normal	HMDB	22308371	details
Human Saliva	Detected but not Quantified				Adult (>18 years old)	Male	Normal	HMDB	22308371	details
Human Saliva	Detected but not Quantified				Adult (>18 years old)	Male	Normal	HMDB	22308371	details
Human Saliva	Detected but not Quantified				Adult (>18 years old)	Male	Normal	HMDB	22308371	details
Human Saliva	Detected but not Quantified				Adult (>18 years old)	Male	Normal	HMDB	22308371	details
Human Saliva	Detected but not Quantified				Adult (>18 years old)	Male	Normal	HMDB	22308371	details
Human Saliva	Detected but not Quantified				Adult (>18 years old)	Male	Normal	HMDB	22308371	details
Human Saliva	Detected but not Quantified				Adult (>18 years old)	Male	Normal	HMDB	22308371	details
Human Saliva	Detected but not Quantified				Adult (>18 years old)	Male	Normal	HMDB	22308371	details
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	27543620	details
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	25037050	details
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	29808030	details

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Zaidi SN, Laidlaw I, Howell A, Potten CS, Cooper DP, O'Connor PJ: Normal human breast xenografts activate N-nitrosodimethylamine: identification of potential target cells for an environmental nitrosamine. Br J Cancer. 1992 Jul;66(1):79-83. doi: 10.1038/bjc.1992.220. [PubMed:1637681 ]
Markert ML: Purine nucleoside phosphorylase deficiency. Immunodefic Rev. 1991;3(1):45-81. [PubMed:1931007 ]
Staal GE, Stoop JW, Zegers BJ, Siegenbeek van Heukelom LH, van der Vlist MJ, Wadman SK, Martin DW: Erythrocyte metabolism in purine nucleoside phosphorylase deficiency after enzyme replacement therapy by infusion of erythrocytes. J Clin Invest. 1980 Jan;65(1):103-8. doi: 10.1172/JCI109639. [PubMed:6765955 ]
Schilderman PA, Rhijnsburger E, Zwingmann I, Kleinjans JC: Induction of oxidative DNA damages and enhancement of cell proliferation in human lymphocytes in vitro by butylated hydroxyanisole. Carcinogenesis. 1995 Mar;16(3):507-12. doi: 10.1093/carcin/16.3.507. [PubMed:7697806 ]
Bialkowski K, Kowara R, Windorbska W, Olinski R: 8-Oxo-2'-deoxyguanosine level in lymphocytes DNA of cancer patients undergoing radiotherapy. Cancer Lett. 1996 Jan 19;99(1):93-7. doi: 10.1016/0304-3835(95)04042-0. [PubMed:8564935 ]
Hou SM, Nori P, Fang JL, Vaca CE: Methylglyoxal induces hprt mutation and DNA adducts in human T-lymphocytes in vitro. Environ Mol Mutagen. 1995;26(4):286-91. doi: 10.1002/em.2850260404. [PubMed:8575417 ]
Podmore K, Farmer PB, Herbert KE, Jones GD, Martin EA: 32P-postlabelling approaches for the detection of 8-oxo-2'-deoxyguanosine-3'-monophosphate in DNA. Mutat Res. 1997 Aug 1;378(1-2):139-49. doi: 10.1016/s0027-5107(97)00104-8. [PubMed:9288892 ]
Wevers RA, Engelke UF, Moolenaar SH, Brautigam C, de Jong JG, Duran R, de Abreu RA, van Gennip AH: 1H-NMR spectroscopy of body fluids: inborn errors of purine and pyrimidine metabolism. Clin Chem. 1999 Apr;45(4):539-48. [PubMed:10102915 ]
Kaneko T, Tahara S: Formation of 8-oxo-2'-deoxyguanosine in the DNA of human diploid fibroblasts by treatment with linoleic acid hydroperoxide and ferric ion. Lipids. 2000 Sep;35(9):961-5. doi: 10.1007/s11745-000-0606-y. [PubMed:11026616 ]
Blair IA: Lipid hydroperoxide-mediated DNA damage. Exp Gerontol. 2001 Sep;36(9):1473-81. doi: 10.1016/s0531-5565(01)00133-4. [PubMed:11525870 ]
Izzedine H, Launay-Vacher V, Aymard G, Legrand M, Deray G: Pharmacokinetics of abacavir in HIV-1-infected patients with impaired renal function. Nephron. 2001 Sep;89(1):62-7. doi: 10.1159/000046045. [PubMed:11528234 ]
Takamura-Enya T, Watanabe M, Totsuka Y, Kanazawa T, Matsushima-Hibiya Y, Koyama K, Sugimura T, Wakabayashi K: Mono(ADP-ribosyl)ation of 2'-deoxyguanosine residue in DNA by an apoptosis-inducing protein, pierisin-1, from cabbage butterfly. Proc Natl Acad Sci U S A. 2001 Oct 23;98(22):12414-9. doi: 10.1073/pnas.221444598. Epub 2001 Oct 9. [PubMed:11592983 ]
Gackowski D, Ciecierski M, Jawien A, Olinski R: Background level of 8-oxo-2'-deoxyguanosine in lymphocyte DNA does not correlate with the concentration of antioxidant vitamins in blood plasma. Acta Biochim Pol. 2001;48(2):535-9. [PubMed:11732622 ]
Schramm VL: Development of transition state analogues of purine nucleoside phosphorylase as anti-T-cell agents. Biochim Biophys Acta. 2002 Jul 18;1587(2-3):107-17. doi: 10.1016/s0925-4439(02)00073-x. [PubMed:12084452 ]
Gackowski D, Banaszkiewicz Z, Rozalski R, Jawien A, Olinski R: Persistent oxidative stress in colorectal carcinoma patients. Int J Cancer. 2002 Oct 1;101(4):395-7. doi: 10.1002/ijc.10610. [PubMed:12209966 ]
Bowen P, Chen L, Stacewicz-Sapuntzakis M, Duncan C, Sharifi R, Ghosh L, Kim HS, Christov-Tzelkov K, van Breemen R: Tomato sauce supplementation and prostate cancer: lycopene accumulation and modulation of biomarkers of carcinogenesis. Exp Biol Med (Maywood). 2002 Nov;227(10):886-93. doi: 10.1177/153537020222701008. [PubMed:12424330 ]
Araki S, Hayashi M, Tamagawa K, Saito M, Kato S, Komori T, Sakakihara Y, Mizutani T, Oda M: Neuropathological analysis in spinal muscular atrophy type II. Acta Neuropathol. 2003 Nov;106(5):441-8. doi: 10.1007/s00401-003-0743-9. Epub 2003 Jul 25. [PubMed:12898156 ]
Palozza P, Serini S, Di Nicuolo F, Boninsegna A, Torsello A, Maggiano N, Ranelletti FO, Wolf FI, Calviello G, Cittadini A: beta-Carotene exacerbates DNA oxidative damage and modifies p53-related pathways of cell proliferation and apoptosis in cultured cells exposed to tobacco smoke condensate. Carcinogenesis. 2004 Aug;25(8):1315-25. doi: 10.1093/carcin/bgh142. Epub 2004 Apr 8. [PubMed:15073048 ]
Gao K, Henning SM, Niu Y, Youssefian AA, Seeram NP, Xu A, Heber D: The citrus flavonoid naringenin stimulates DNA repair in prostate cancer cells. J Nutr Biochem. 2006 Feb;17(2):89-95. doi: 10.1016/j.jnutbio.2005.05.009. Epub 2005 Jun 20. [PubMed:16111881 ]
Shibata T, Iio K, Kawai Y, Shibata N, Kawaguchi M, Toi S, Kobayashi M, Kobayashi M, Yamamoto K, Uchida K: Identification of a lipid peroxidation product as a potential trigger of the p53 pathway. J Biol Chem. 2006 Jan 13;281(2):1196-204. doi: 10.1074/jbc.M509065200. Epub 2005 Oct 26. [PubMed:16251187 ]
Kato I, Ren J, Heilbrun LK, Djuric Z: Intra- and inter-individual variability in measurements of biomarkers for oxidative damage in vivo: Nutrition and Breast Health Study. Biomarkers. 2006 Mar-Apr;11(2):143-52. doi: 10.1080/13547500600565693. [PubMed:16766390 ]

Showing metabocard for Deoxyguanosine (MMDBc0029470)

MOL for #<Metabolite:0x0000564abc22b138>

3D MOL for #<Metabolite:0x0000564abc22b138>

3D SDF for #<Metabolite:0x0000564abc22b138>

3D-SDF for #<Metabolite:0x0000564abc22b138>

PDB for #<Metabolite:0x0000564abc22b138>

3D PDB for #<Metabolite:0x0000564abc22b138>

SMILES for #<Metabolite:0x0000564abc22b138>

INCHI for #<Metabolite:0x0000564abc22b138>

Structure for #<Metabolite:0x0000564abc22b138>

3D Structure for #<Metabolite:0x0000564abc22b138>