FComEx: Cytidine (PC000408)

Record Information

Version

1.0

Creation date

2015-10-09 22:30:30 UTC

Update date

2017-01-19 02:36:22 UTC

FoodComEx ID

PC000408

FoodDB Record

FDB021809

Chemical Information

Name

Cytidine

Description

Cytidine is a nucleoside that is composed of the base cytosine linked to the five-carbon sugar D-ribose. Cytidine is a pyrimidine that besides being incorporated into nucleic acids, can serve as substrate for the salvage pathway of pyrimidine nucleotide synthesis; as precursor of the cytidine triphosphate (CTP) needed in the phosphatidylcholine (PC) and phosphatidylethanolamine (PE) biosynthetic pathway. These variations probably reflect the species differences in cytidine deaminase, the enzyme that converts cytidine to uridine in the body. The transports of cytidine into the brain's extracellular fluid, and then into neurons and glia, are essential prerequisites for cytidine to be utilized in brain. An efficient mechanism mediating the brain uptake of circulating cytidine has not yet been demonstrated. The biosynthesis of PC, the most abundant phosphatide in the brain, via the Kennedy pathway requires phosphocholine and cytidine triphosphate (CTP), a cytidine nucleotide, which is involved in the rate-limiting step. The enzyme that converts CTP to endogenous CDP-choline (CTP: phosphocholine cytidylyltransferase) is unsaturated at physiological brain CTP levels. APOBEC is a family of enzymes has been discovered with the ability to deaminate cytidines on RNA or DNA. The human apolipoprotein B mRNA-editing enzyme, catalytic polypeptide-like 3G (APOBEC3G, or hA3G) protein, provides cells with an intracellular antiretroviral activity that is associated with the hypermutation of viral DNA through cytidine deamination. Indeed, hA3G belongs to a family of vertebrate proteins that contain one or two copies of a signature sequence motif unique to cytidine deaminases (CTDAs). (PMID: 16769123, 15780864, 16720547) [HMDB]. Cytidine is found in many foods, some of which are sweet potato, rocket salad (sspecies), mexican groundcherry, and cinnamon.

CAS Number

65-46-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1-(b-D-Ribofuranosyl)-2-oxo-4-amino-1,2-dihydro-1,3-diazine	HMDB
1-(b-delta-Ribofuranosyl)-2-oxo-4-amino-1,2-dihydro-1,3-diazine	HMDB
1-b-D-Ribofuranosylcytosine	Generator
1-b-D-Ribosyl-cytosine	HMDB
1-beta-D-Ribofuranosyl-cytosine	HMDB
1-beta-D-Ribofuranosylcytosine	ChEBI
1-beta-delta-Ribofuranosyl-cytosine	HMDB
1-beta-delta-Ribofuranosylcytosine	HMDB
1-beta-delta-Ribosyl-cytosine	HMDB
1-β-D-ribofuranosylcytosine	Generator
1b-D-Ribofuranosylcytosine	Generator
1beta-D-Ribofuranosylcytosine	ChEBI
1beta-delta-Ribofuranosylcytosine	HMDB
1beta-Ribofuranosylcytosine	HMDB
1β-D-ribofuranosylcytosine	Generator
4-amino-1-b-D-RIBOFURANOSYL-2(1H)-pyrimidinone	Generator
4-amino-1-b-D-Ribofuranosylpyrimidin-2(1H)-one	Generator
4-amino-1-BETA-D-RIBOFURANOSYL-2(1H)-pyrimidinone	ChEBI
4-amino-1-beta-D-Ribofuranosylpyrimidin-2(1H)-one	ChEBI
4-amino-1-beta-delta-Ribofuranosyl-2(1H)-pyrimidinone	HMDB
4-amino-1-β-D-ribofuranosyl-2(1H)-pyrimidinone	Generator
4-amino-1-β-D-ribofuranosylpyrimidin-2(1H)-one	Generator
4-amino-1b-D-Ribofuranosyl-2(1H)-pyrimidinone	Generator
4-amino-1beta-D-Ribofuranosyl-2(1H)-pyrimidinone	ChEBI
4-amino-1β-D-ribofuranosyl-2(1H)-pyrimidinone	Generator
Cyd	ChEBI
Cytidin	ChEBI
Cytosine riboside	ChEBI
Cytosine-1b-D-ribofuranoside	Generator
Cytosine-1b-delta-ribofuranoside	HMDB
Cytosine-1beta-D-ribofuranoside	ChEBI
Cytosine-1beta-delta-ribofuranoside	HMDB
Cytosine-1β-D-ribofuranoside	Generator
Zytidin	ChEBI

Chemical Formula

C9H13N3O5

IUPAC name

4-amino-1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one

InChI Identifier

InChI=1S/C9H13N3O5/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16)

InChI Key

UHDGCWIWMRVCDJ-UHFFFAOYSA-N

Isomeric SMILES

OCC1OC(C(O)C1O)N1C=CC(=N)N=C1O

Average Molecular Weight

243.2166

Monoisotopic Molecular Weight

243.085520541

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidine nucleosides. Pyrimidine nucleosides are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleosides

Sub Class

Not Available

Direct Parent

Pyrimidine nucleosides

Alternative Parents