CHEBI:16750 - guanosine

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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:CB0406220, ChemicalBook:CB1323708, eMolecules:533977, eMolecules:27677487, eMolecules:474936, Selleckchem:adenine, ZINC000000000882
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Cannabidiol (CBD) is a phytocannabinoid, one of 113 identified cannabinoids in Cannabis, along with tetrahydrocannabinol (THC), and accounts for up to 40% of the plant's extract. Medically, it is an anticonvulsant used to treat multiple forms of epilepsy. It was discovered in 1940 and, as of 2024 clinical research on CBD included studies related to the treatment of anxiety, addiction, psychosis, movement disorders, and pain, but there is insufficient high-quality evidence that CBD is effective for these conditions. CBD is sold as an herbal dietary supplement and promoted with yet unproven claims of particular therapeutic effects. Cannabidiol can be taken internally in multiple ways, including by inhaling cannabis smoke or vapor, swallowing it by mouth, and through use of an aerosol spray into the cheek. It may be supplied as CBD oil containing only CBD as the active ingredient (excluding THC or terpenes), CBD-dominant hemp extract oil, capsules, dried cannabis, or prescription liquid solution. CBD does not have the same psychoactivity as THC, and can modulate the psychoactive effects of THC on the body if both are present. Conversion of CBD to THC can occur when CBD is heated to temperatures between 250–300 °C, potentially leading to its partial transformation into THC. In the United States, the cannabidiol drug Epidiolex was approved by the Food and Drug Administration (FDA) in 2018 for the treatment of two seizure disorders. While the 2018 United States Farm Bill removed hemp and hemp extracts (including CBD) from the Controlled Substances Act, the marketing and sale of CBD formulations for medical use or as an ingredient in dietary supplements or manufactured foods remains illegal under FDA regulation, as of 2024.
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Formula C10H13N5O5
Net Charge 0
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.
View more via ChEBI Ontology
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
Manual Xrefs Databases
C00019679 KNApSAcK
C00387 KEGG COMPOUND
DB02857 DrugBank
ECMDB00133 ECMDB
GMP PDBeChem
Guanosine Wikipedia
GUANOSINE MetaCyc
HMDB0000133 HMDB
YMDB00509 YMDB
View more database links
Registry Numbers Types Sources
118-00-3 CAS Registry Number ChemIDplus
118-00-3 CAS Registry Number NIST Chemistry WebBook
55323 Gmelin Registry Number Gmelin
625911 Reaxys Registry Number Reaxys
Citations Types Sources
11434576 PubMed citation Europe PMC
15471343 PubMed citation Europe PMC
15920424 PubMed citation Europe PMC
17060520 PubMed citation ChEMBL
17202332 PubMed citation Europe PMC
18191898 PubMed citation Europe PMC
18549801 PubMed citation Europe PMC
21435378 PubMed citation Europe PMC
21500353 PubMed citation Europe PMC
21515778 PubMed citation Europe PMC
21671255 PubMed citation Europe PMC
21774919 PubMed citation Europe PMC
2559771 PubMed citation Europe PMC
Last Modified
06 April 2021