Showing Compound 8-Hydroxy-deoxyguanosine (FDB023145)

Record Information

Version

1.0

Creation date

2011-09-21 00:25:19 UTC

Update date

2015-07-21 06:57:32 UTC

Primary ID

FDB023145

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

8-Hydroxy-deoxyguanosine

Description

8-Hydroxy-deoxyguanosine, also known as 8-ohdg or 8-oxo-2'-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. 8-Hydroxy-deoxyguanosine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 8-hydroxy-deoxyguanosine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 8-Hydroxy-deoxyguanosine.

CAS Number

88847-89-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Search:

Synonym	Source
2'-Deoxy-7,8-dihydro-8-oxoguanosine	MeSH, HMDB
2'-Deoxy-8-hydroxyguanosine	MeSH, HMDB
2'-Deoxy-8-oxo-7,8-dihydroguanosine	MeSH, HMDB
2'-Deoxy-8-oxoguanosine	MeSH, HMDB
7,8-Dihydro-2'-deoxy-8-oxoguanosine	ChEBI
7,8-dihydro-2'-Deoxy-8-oxoguanosine	ChEBI
7,8-dihydro-8-oxo-2'-Deoxyguanosine	HMDB, MeSH
7,8-Dihydro-8-oxo-2'-deoxyguanosine	hmdb
7,8-dihydro-8-Oxodeoxyguanosine	HMDB
7,8-Dihydro-8-oxodeoxyguanosine	hmdb

Showing 1 to 10 of 42 entries

Predicted Properties

Property	Value	Source
Water Solubility	14.8 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-1.4	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	10.09	ChemAxon
pKa (Strongest Basic)	1.59	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	155.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	64.56 m³·mol⁻¹	ChemAxon
Polarizability	25.82 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H13N5O5

IUPAC name

2-amino-8-hydroxy-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one

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

Isomeric SMILES

NC1=NC2=C(N=C(O)N2[C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)N1

Average Molecular Weight

283.2407

Monoisotopic Molecular Weight

283.091668551

Classification

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
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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

guanosines (CHEBI:40304 )

Ontology

Dermal

Enteral:

Ingestion

Source:

Endogenous

Biological location:

Tissue and substructures:

All tissues

Subcellular:

Biofluid and excreta:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	8-Hydroxy-deoxyguanosine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9270000000-cbf066db8be0f3462b6d	Spectrum
Predicted GC-MS	8-Hydroxy-deoxyguanosine, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9503400000-ff14681f666eee936938	Spectrum
Predicted GC-MS	8-Hydroxy-deoxyguanosine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-Ion Trap , Positive	splash10-0a4i-1649170600-b830f720eac21d5be0a6	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-014i-0900000000-bda7c71c752f3e3c4c51	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-279a84bf501a3d5c6555	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0900000000-8b53d5aeced1f8b887ae	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uxr-0900000000-1db539ae30cc3fae45ef	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0290000000-77880ee90b3d77e9f3f4	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kf-0920000000-8ab5275c7f1f98f7c143	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dm-4900000000-4c65e34bf57ca440e280	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-1df07afca955f854b771	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014r-0950000000-7088092794cc25cf636c	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fxy-2900000000-16fdd2a07e854814fc6a	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00lr-0490000000-6a3ea27ba97cf9405385	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0900000000-d28ab0ab8ba89b944e85	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05ox-2910000000-d457b32e33bd1c0ab8f9	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

66049

ChEMBL ID

CHEMBL1230628

KEGG Compound ID

Not Available

Pubchem Compound ID

73318

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB03333

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

8HG

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Anatidae	Expected but not quantified	Not Available	HMDB
Beefalo	Expected but not quantified	Not Available	HMDB
Bison	Expected but not quantified	Not Available	HMDB
Buffalo	Expected but not quantified	Not Available	HMDB
Cattle (Beef, Veal)	Expected but not quantified	Not Available	HMDB
Chicken	Expected but not quantified	Not Available	HMDB
Columbidae (Dove, Pigeon)	Expected but not quantified	Not Available	HMDB
Deer	Expected but not quantified	Not Available	HMDB
Domestic goat	Expected but not quantified	Not Available	HMDB
Domestic pig	Expected but not quantified	Not Available	HMDB