guanosine (CHEBI:16750)

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ChEBI Name	guanosine

ChEBI ID	CHEBI:16750

Definition	A purine nucleoside in which guanine is attached to ribofuranose via a β-N⁹-glycosidic bond.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:42840, CHEBI:42847, CHEBI:42853, CHEBI:471737, CHEBI:5564, CHEBI:14375, CHEBI:24444

Supplier Information	ChemicalBook:CB9375521, ChemicalBook:CB7162318, eMolecules:496860, ZINC000001081581

Download	Molfile XML SDF

Wikipedia	License
Deoxyadenosine (symbol dA or dAdo) is a deoxyribonucleoside. It is a derivative of the nucleoside adenosine, differing from the latter by the replacement of a hydroxyl group (-OH) by hydrogen (-H) at the 2′ position of its ribose sugar moiety. Deoxyadenosine is the DNA nucleoside A, which pairs with deoxythymidine (T) in double-stranded DNA. In absence of adenosine deaminase (ADA) it accumulates in T lymphocytes and kills these cells resulting in a genetic disorder known as adenosine deaminase severe combined immunodeficiency disease (ADA-SCID).
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Formula

C10H13N5O5

Net Charge

Average Mass

283.24092

Monoisotopic Mass

283.09167

InChI

InChI=1S/C10H13N5O5/c11-10-13-7-4(8(19)14-10)12-2-15(7)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5-,6-,9-/m1/s1

InChIKey

NYHBQMYGNKIUIF-UUOKFMHZSA-N

SMILES

Nc1nc2n(cnc2c(=O)[nH]1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Saccharomyces cerevisiae (NCBI:txid4932)	Source: yeast.sf.net See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed
Homo sapiens (NCBI:txid9606)	See: DOI

Roles Classification
Biological Role(s):	fundamental metabolite Any metabolite produced by all living cells.

ChEBI Ontology
Outgoing	guanosine (CHEBI:16750) has functional parent guanine (CHEBI:16235) guanosine (CHEBI:16750) has role fundamental metabolite (CHEBI:78675) guanosine (CHEBI:16750) is a guanosines (CHEBI:24458) guanosine (CHEBI:16750) is a purines D-ribonucleoside (CHEBI:142355)

Incoming	2'-deoxyguanosine (CHEBI:17172) has functional parent guanosine (CHEBI:16750) 4-demethyl-7-(3-amino-3-carboxypropyl)wyosine 5'-monophosphate (CHEBI:73557) has functional parent guanosine (CHEBI:16750) 4-demethylwyosine (CHEBI:64313) has functional parent guanosine (CHEBI:16750) 7-(2-hydroxy-3-amino-3-carboxypropyl)wyosine 5'-monophosphate (CHEBI:73625) has functional parent guanosine (CHEBI:16750) 7-(3-amino-3-carboxypropyl)wyosine 5'-monophosphate (CHEBI:73553) has functional parent guanosine (CHEBI:16750) 7-[(3S)-(3-amino-3-methoxycarbonyl)propyl]wyosine 5'-phosphate (CHEBI:74446) has functional parent guanosine (CHEBI:16750) cytidylyl-(3'→5')-guanosine (CHEBI:167896) has functional parent guanosine (CHEBI:16750) N²-(ADP-D-ribosyl)-guanosine(2−) (CHEBI:142714) has functional parent guanosine (CHEBI:16750) wybutosine (CHEBI:46574) has functional parent guanosine (CHEBI:16750) wybutoxosine (CHEBI:64330) has functional parent guanosine (CHEBI:16750) guanosine residue (CHEBI:64654) is substituent group from guanosine (CHEBI:16750)

IUPAC Name

guanosine

Synonyms	Sources
2(3H)-imino-9-β-D-ribofuranosyl-9H-purin-6(1H)-one	NIST Chemistry WebBook
2-amino-1,9-dihydro-9-β-D-ribofuranosyl-6H-purin-6-one	HMDB
2-amino-9-β-D-ribofuranosyl-1,9-dihydro-6H-purin-6-one	IUPAC
9-β-D-ribofuranosyl-guanine	HMDB
G	ChEBI
Guanine riboside	NIST Chemistry WebBook
Guanine-9-β-D-ribofuranoside	NIST Chemistry WebBook
Guanosin	ChEBI
Guanosine	KEGG COMPOUND
guanosine	UniProt
Guo	CBN

Last Modified

06 April 2021