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

2024-10-17 18:31:41 UTC

Metabolite 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

Value	Source
2-Amino-9-(2-deoxy-9-beta-D-ribofuranosyl)-9H-purin-6-ol	ChEBI
9-(2-Deoxy-beta-D-erythro-pentofuranosyl)-guanine	ChEBI
dG	ChEBI
Guanine deoxy nucleoside	ChEBI
2'-Deoxyguanosine	Kegg
2-Amino-9-(2-deoxy-9-b-D-ribofuranosyl)-9H-purin-6-ol	Generator
2-Amino-9-(2-deoxy-9-β-D-ribofuranosyl)-9H-purin-6-ol	Generator
9-(2-Deoxy-b-D-erythro-pentofuranosyl)-guanine	Generator
9-(2-Deoxy-β-D-erythro-pentofuranosyl)-guanine	Generator
2'-Deoxy-guanosine	HMDB
2-Deoxyguanosine	HMDB
9-(2-Deoxy-b-D-erythro-pentofuranosyl)guanine	HMDB
9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)-guanine	HMDB
9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)guanine	HMDB
Desoxyguanosine	HMDB
Guanine deoxyriboside	HMDB
Deoxyguanosine	ChEBI

Molecular Formula

C₁₀H₁₃N₅O₄

Average Mass

267.2413

Monoisotopic Mass

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

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.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleosides

Sub Class

Purine 2'-deoxyribonucleosides

Direct Parent

Purine 2'-deoxyribonucleosides

Alternative Parents

Substituents

Purine 2'-deoxyribonucleoside
6-oxopurine
Hypoxanthine
Purinone
Imidazopyrimidine
Purine
Aminopyrimidine
Pyrimidone
N-substituted imidazole
Pyrimidine
Azole
Imidazole
Heteroaromatic compound
Vinylogous amide
Tetrahydrofuran
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Amine
Primary amine
Primary alcohol
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

purine 2'-deoxyribonucleoside (CHEBI:17172 )
Deoxyribonucleosides (C00330 )

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

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191677	5'-nucleotidase	Unknown	P21589	Homo sapiens
MMDBp0191680	Cytosolic 5'-nucleotidase 1B	Unknown	Q96P26	Homo sapiens
MMDBp0191681	Cytosolic 5'-nucleotidase 1A	Unknown	Q9BXI3	Homo sapiens
MMDBp0191682	5'(3')-deoxyribonucleotidase, cytosolic type	Unknown	Q8TCD5	Homo sapiens
MMDBp0191684	5'(3')-deoxyribonucleotidase, mitochondrial	Unknown	Q9NPB1	Homo sapiens
MMDBp0192388	Deoxyguanosine kinase, mitochondrial	Enzyme	Q16854	Homo sapiens
MMDBp0193860	Cytosolic 5'-nucleotidase 3	Enzyme	Q9H0P0	Homo sapiens
MMDBp0193932	Cytosolic purine 5'-nucleotidase	Unknown	P49902	Homo sapiens
MMDBp0193933	Purine nucleoside phosphorylase	Enzyme	P00491	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0000660	Deoxyguanosine	2'-Deoxyguanosine 5'-monophosphate	deoxyguanosine kinase	VMH; KEGG	12535661 8692979
MMDBr0001797	2'-Deoxyguanosine 5'-monophosphate	Deoxyguanosine	acid phosphatase 2, lysosomal	VMH	30371894
MMDBr0002565	Deoxyguanosine	2'-Deoxyguanosine 5'-monophosphate	Not Available	VMH	15748706
MMDBr0007556	Deoxyguanosine	Deoxyribose 1-phosphate	Not Available	VMH; KEGG	30371894
MMDBr0007642	2'-Deoxyguanosine 5'-monophosphate	Deoxyguanosine	Not Available	VMH; KEGG	30371894
MMDBr0007924	dGTP	Deoxyguanosine	Not Available	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Purine nucleoside phosphorylase deficiency		Association	Human Blood	HMDB	16131572
Purine nucleoside phosphorylase deficiency	Increased	Association	Human Urine	HMDB	10102915

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	322	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	569	Human feces; Human pleural fluid plaque; Pig ; Human ; Human urine; Human mucosa; Human sputum; Human saliva; Human supragingival plaque; Cattle ; Human stool; Human subgingival plaque	Metabolic reconstruction
Bacteria	Actinobacteria	159	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria	Verrucomicrobia	2	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	241	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria	Synergistetes	5	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	2		Metabolic reconstruction
Bacteria	Fusobacteria	29	Human feces; Human	Metabolic reconstruction
Bacteria	Candidatus melainabacteria	2	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	6		Metabolic reconstruction
Bacteria	Tenericutes	5	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Activity	Data Source	Reference
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

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

External Links

HMDB ID

HMDB0000085

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012064

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

17172

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:0x00007fdb519fae00>

3D MOL for #<Metabolite:0x00007fdb519fae00>

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