2'-deoxyadenosine (CHEBI:17256)

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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	ChemicalBook:CB6141459, eMolecules:531173, eMolecules:29541183, Selleckchem:Alprostadil(Caverject), ZINC000003813088

Download	Molfile XML SDF

more structures >>

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31 33 0 0 0 0 999 V2000

-4.6460 1.7090 -1.0590 O 0 0 0 0 0 0 0 0 0 0 0 0

-4.2140 0.9940 0.1010 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.1800 -0.0580 -0.3040 C 0 0 1 0 0 0 0 0 0 0 0 0

-1.9360 0.5670 -0.6910 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.9090 -0.4300 -0.5590 C 0 0 1 0 0 0 0 0 0 0 0 0

0.3430 0.1980 -0.1310 N 0 0 0 0 0 0 0 0 0 0 0 0

1.6080 -0.3000 -0.3190 C 0 0 0 0 0 0 0 0 0 0 0 0

2.1110 -1.3920 -0.8850 N 0 0 0 0 0 0 0 0 0 0 0 0

3.4110 -1.5960 -0.9100 C 0 0 0 0 0 0 0 0 0 0 0 0

4.2730 -0.7440 -0.3850 N 0 0 0 0 0 0 0 0 0 0 0 0

3.8630 0.3760 0.2010 C 0 0 0 0 0 0 0 0 0 0 0 0

4.7730 1.2630 0.7480 N 0 0 0 0 0 0 0 0 0 0 0 0

2.4830 0.6350 0.2580 C 0 0 0 0 0 0 0 0 0 0 0 0

1.7220 1.6410 0.7530 N 0 0 0 0 0 0 0 0 0 0 0 0

0.4660 1.3850 0.5280 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.3800 -1.4390 0.5070 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.7850 -0.9330 0.9130 C 0 0 2 0 0 0 0 0 0 0 0 0

-3.6940 -2.0240 1.0740 O 0 0 0 0 0 0 0 0 0 0 0 0

-5.2950 2.3600 -0.7600 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.0690 0.5040 0.5660 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.7650 1.6900 0.8100 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.5640 -0.6790 -1.1140 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.7610 -0.9390 -1.5110 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.3570 2.0200 0.8210 H 0 0 0 0 0 0 0 0 0 0 0 0

3.7880 -2.4940 -1.3770 H 0 0 0 0 0 0 0 0 0 0 0 0

5.7230 1.0710 0.7060 H 0 0 0 0 0 0 0 0 0 0 0 0

4.4620 2.0790 1.1700 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.4430 -2.4410 0.0820 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.7080 -1.4290 1.3650 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.7350 -0.3330 1.8220 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.3420 -2.5780 1.7850 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 1 0 0 0 0

1 19 1 0 0 0 0

2 3 1 0 0 0 0

2 20 1 0 0 0 0

2 21 1 0 0 0 0

3 4 1 0 0 0 0

3 17 1 0 0 0 0

3 22 1 0 0 0 0

4 5 1 0 0 0 0

5 6 1 0 0 0 0

5 16 1 0 0 0 0

5 23 1 0 0 0 0

6 7 4 0 0 0 0

6 15 4 0 0 0 0

7 8 4 0 0 0 0

7 13 4 0 0 0 0

8 9 4 0 0 0 0

9 10 4 0 0 0 0

9 25 1 0 0 0 0

10 11 4 0 0 0 0

11 12 1 0 0 0 0

11 13 4 0 0 0 0

12 26 1 0 0 0 0

12 27 1 0 0 0 0

13 14 4 0 0 0 0

14 15 4 0 0 0 0

15 24 1 0 0 0 0

16 17 1 0 0 0 0

16 28 1 0 0 0 0

16 29 1 0 0 0 0

17 18 1 0 0 0 0

17 30 1 0 0 0 0

18 31 1 0 0 0 0

M END): 18 ms

reading 31 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

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31 atoms created

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Wikipedia	License
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.
Read full article at Wikipedia

Formula

C10H13N5O3

Net Charge

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).

View more via ChEBI Ontology

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

CHEBI:17256 - 2'-deoxyadenosine

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