CHEBI:17256 - 2'-deoxyadenosine

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ChEBI Name 2'-deoxyadenosine
ChEBI ID CHEBI:17256
Definition A purine 2'-deoxyribonucleoside having adenine as the nucleobase.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:39863, CHEBI:40535, CHEBI:19234, CHEBI:40560, CHEBI:40565, CHEBI:4405, CHEBI:14112
Supplier Information eMolecules:1935398, eMolecules:26753648, ZINC000008215926
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Prostaglandin E1 (PGE1) is a naturally occurring prostaglandin with various medical uses. Alprostadil and misoprostol are synthetic forms of prostaglandin E1 used as medications. Lubiprostone, a derivative of prostaglandin E1, is also used as a medication. Prostaglandin E1 is a vasodilator. It has various effects in the body that include opening blood vessels, relaxing smooth muscle, inhibiting clotting, and causing uterine contractions. In infants with certain congenital heart defects, alprostadil is delivered by slow injection into a vein to maintain a patent ductus arteriosus until surgery can be carried out. By injection into the penis or placement in the urethra, alprostadil is used to treat erectile dysfunction. Common side effects when given to babies include decreased breathing, fever, and low blood pressure. When injected into the penis for erectile dysfunction; side effects may include penile pain, bleeding at the site of injection, and prolonged erection (priapism). Prostaglandin E1 was isolated in 1957 and approved for medical use in the United States in 1981. Misoprostol has various obstetric uses. It is used to induce abortion, to completely empty the uterus after a miscarriage, to induce labor, and to prevent and treat postpartum hemorrhage. The medication is available through many routes. It can be swallowed, dissolved in the mouth, placed in the vagina, or placed in the rectum. Misoprostol can also be used to manage duodenal ulcers and peptic ulcer disease when other medications are not effective. It is on the World Health Organization's List of Essential Medicines for its obstetric uses. Lubiprostone is a PGE1 derivative used to treat chronic constipation. It is taken orally. Common side effects include diarrhea, vomiting, and abdominal pain.
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Formula C10H13N5O3
Net Charge 0
Average Mass 251.24212
Monoisotopic Mass 251.10184
InChI InChI=1S/C10H13N5O3/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(17)6(2-16)18-7/h3-7,16-17H,1-2H2,(H2,11,12,13)/t5-,6+,7+/m0/s1
InChIKey OLXZPDWKRNYJJZ-RRKCRQDMSA-N
SMILES Nc1ncnc2n(cnc12)[C@H]1C[C@H](O)[C@@H](CO)O1
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): Saccharomyces cerevisiae metabolite
Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ).
Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
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ChEBI Ontology
Outgoing 2'-deoxyadenosine (CHEBI:17256) has role Escherichia coli metabolite (CHEBI:76971)
2'-deoxyadenosine (CHEBI:17256) has role Saccharomyces cerevisiae metabolite (CHEBI:75772)
2'-deoxyadenosine (CHEBI:17256) has role human metabolite (CHEBI:77746)
2'-deoxyadenosine (CHEBI:17256) has role mouse metabolite (CHEBI:75771)
2'-deoxyadenosine (CHEBI:17256) is a purine 2'-deoxyribonucleoside (CHEBI:19254)
2'-deoxyadenosine (CHEBI:17256) is a purines 2'-deoxy-D-ribonucleoside (CHEBI:142361)
Incoming 8,5'-cyclo-2'-deoxyadenosine (CHEBI:131825) has functional parent 2'-deoxyadenosine (CHEBI:17256)
IUPAC Name
2'-deoxyadenosine
Synonyms Sources
(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol IUPAC
2'-Deoxyadenosine KEGG COMPOUND
2'-deoxyadenosine UniProt
5-(6-AMINO-PURIN-9-YL)-2-HYDROXYMETHYL-TETRAHYDRO-FURAN-3-OL PDBeChem
9-(2-Deoxy-β-D-erythro-pentofuranosyl)adenine NIST Chemistry WebBook
9-(2-deoxy-β-D-ribofuranosyl)-9H-purin-6-amine NIST Chemistry WebBook
adenine deoxyribonucleoside ChemIDplus
adenyldeoxyriboside ChemIDplus
dA ChEBI
Deoxyadenosine KEGG COMPOUND
Manual Xrefs Databases
3D1 PDBeChem
C00019281 KNApSAcK
C00559 KEGG COMPOUND
Deoxyadenosine Wikipedia
DEOXYADENOSINE MetaCyc
HMDB0000101 HMDB
View more database links
Registry Numbers Types Sources
283189 Gmelin Registry Number Gmelin
91015 Reaxys Registry Number Reaxys
958-09-8 CAS Registry Number KEGG COMPOUND
958-09-8 CAS Registry Number ChemIDplus
958-09-8 CAS Registry Number NIST Chemistry WebBook
Citations Types Sources
14253484 PubMed citation Europe PMC
18508186 PubMed citation Europe PMC
24144081 PubMed citation Europe PMC
8171392 PubMed citation Europe PMC
9869364 PubMed citation Europe PMC
Last Modified
21 April 2016