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Details

Stereochemistry ACHIRAL
Molecular Formula C4H5N3O
Molecular Weight 111.1022
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYTOSINE

SMILES

c1cnc([nH]c1=N)O

InChI

InChIKey=OPTASPLRGRRNAP-UHFFFAOYSA-N
InChI=1S/C4H5N3O/c5-3-1-2-6-4(8)7-3/h1-2H,(H3,5,6,7,8)

HIDE SMILES / InChI

Molecular Formula C4H5N3O
Molecular Weight 111.1022
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Cytosine is a pyrimidine nucleobase, one of the five main bases of nucleic acids. In DNA and RNA cytosine is paired with guanine. Only small amounts of cytosine administered with food are incorporated in DNA. The majority of cytosine is synthesized de-novo starting from carbamoyl phosphate.

CNS Activity

Curator's Comment:: Cytosine administered with food does not pass through blood-brain barrier. Cytosine is synthesized in the brain de-novo.

Approval Year

PubMed

PubMed

TitleDatePubMed
Toxic epidermal necrolysis and graft vs. host disease: a clinical spectrum but a diagnostic dilemma.
1999 Jul
A simple model based on mutation and selection explains trends in codon and amino-acid usage and GC composition within and across genomes.
2001
Suicide gene therapy for pediatric tumors.
2001
UAG readthrough in mammalian cells: effect of upstream and downstream stop codon contexts reveal different signals.
2001
Ionization mechanism of oligonucleotides in matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.
2001
Low-energy (5-40 eV) electron-stimulated desorption of anions from physisorbed DNA bases.
2001 Apr
15-mer DNA duplexes containing an abasic site are thermodynamically more stable with adjacent purines than with pyrimidines.
2001 Apr 3
Isolation and frontier molecular orbital investigation of bioactive quinone-methide triterpenoids from the bark of Salacia petenensis.
2001 Feb
Size constraints for targeting post-transcriptional gene silencing and for RNA-directed methylation in Nicotiana benthamiana using a potato virus X vector.
2001 Feb
Host responses and persistence of vector genome following intrabronchial administration of an E1(-)E3(-) adenovirus gene transfer vector to normal individuals.
2001 Feb
Probing structure and function with alternative nucleic acids bearing 2',5'-linked, zwitterionic, and isocytosine-isoguanine components.
2001 Feb
Site-specific methylation of the promoter alters deoxyribonucleic acid-protein interactions and prevents follicle-stimulating hormone receptor gene transcription.
2001 Feb
Troxacitabine, a novel dioxolane nucleoside analog, has activity in patients with advanced leukemia.
2001 Feb 1
Alkylating agent and chromatin structure determine sequence context-dependent formation of alkylpurines.
2001 Feb 16
Microsoft Word macro for analysis of cytosine methylation by the bisulfite deamination reaction.
2001 Jan
Spreadsheet-based program for the analysis of DNA methylation.
2001 Jan
Usefulness of repeated direct intratumoral gene transfer using hemagglutinating virus of Japan-liposome method for cytosine deaminase suicide gene therapy.
2001 Jan 1
Regions of low single-nucleotide polymorphism incidence in human and orangutan xq: deserts and recent coalescences.
2001 Jan 1
The RihA, RihB, and RihC ribonucleoside hydrolases of Escherichia coli. Substrate specificity, gene expression, and regulation.
2001 Jan 12
Virological, clinical, and ophthalmologic features of cytomegalovirus retinitis after hematopoietic stem cell transplantation.
2001 Jan 15
Molecular dynamics simulation reveals conformational switching of water-mediated uracil-cytosine base-pairs in an RNA duplex.
2001 Jan 26
In-situ FTIR study on adsorption and oxidation of native and thermally denatured calf thymus DNA at glassy carbon electrodes.
2001 Jan 31
X-ray absorption near edge structures of DNA or its components around the oxygen K-shell edge.
2001 Mar
Tetraplex formation by the progressive myoclonus epilepsy type-1 repeat: implications for instability in the repeat expansion diseases.
2001 Mar 2
Solution structure of an A-tract DNA bend.
2001 Mar 9
Molecular topology of polycyclic aromatic carcinogens determines DNA adduct conformation: a link to tumorigenic activity.
2001 Mar 9
Actinomycin D binds strongly to d(TGTCATTG), a single-stranded DNA devoid of GpC sites.
2001 May 1
Treatment of adenovirus infections in patients undergoing allogeneic hematopoietic stem cell transplantation.
2001 May 1
Catechol estrogens induce oxidative DNA damage and estradiol enhances cell proliferation.
2001 May 1
Patents

Patents

Sample Use Guides

In Vivo Use Guide
As a component of DNA, cytosine is ingested with a normal diet. Normally, a major amount of cytosine is excreted, and a small amount is incorporated into DNA of the gastrointestinal tract.
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Sat Jun 26 06:28:23 UTC 2021
Edited
by admin
on Sat Jun 26 06:28:23 UTC 2021
Record UNII
8J337D1HZY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CYTOSINE
INCI   MI   USP-RS  
INCI  
Official Name English
NSC-27787
Code English
4-AMINOURACIL
Common Name English
LAMIVUDINE IMPURITY E [EP]
Common Name English
CYTOSINE [MI]
Common Name English
CYTOSINE [INCI]
Common Name English
LAMIVUDINE IMPURITY C [USP]
Common Name English
CYTOSINIMINE
Systematic Name English
CYTOSINE [USP-RS]
Common Name English
LAMIVUDINE IMPURITY C RS [USP]
Common Name English
4-AMINOPYRIMIDIN-2(1H)-ONE
Systematic Name English
Classification Tree Code System Code
EU-Orphan Drug EU/3/07/476
Created by admin on Sat Jun 26 06:28:23 UTC 2021 , Edited by admin on Sat Jun 26 06:28:23 UTC 2021
LOINC 79658-1
Created by admin on Sat Jun 26 06:28:23 UTC 2021 , Edited by admin on Sat Jun 26 06:28:23 UTC 2021
NCI_THESAURUS C789
Created by admin on Sat Jun 26 06:28:23 UTC 2021 , Edited by admin on Sat Jun 26 06:28:23 UTC 2021
LOINC 79655-7
Created by admin on Sat Jun 26 06:28:23 UTC 2021 , Edited by admin on Sat Jun 26 06:28:23 UTC 2021
LOINC 79683-9
Created by admin on Sat Jun 26 06:28:23 UTC 2021 , Edited by admin on Sat Jun 26 06:28:23 UTC 2021
Code System Code Type Description
RXCUI
1372540
Created by admin on Sat Jun 26 06:28:23 UTC 2021 , Edited by admin on Sat Jun 26 06:28:23 UTC 2021
PRIMARY RxNorm
EVMPD
SUB34834
Created by admin on Sat Jun 26 06:28:23 UTC 2021 , Edited by admin on Sat Jun 26 06:28:23 UTC 2021
PRIMARY
MESH
D003596
Created by admin on Sat Jun 26 06:28:23 UTC 2021 , Edited by admin on Sat Jun 26 06:28:23 UTC 2021
PRIMARY
CAS
71-30-7
Created by admin on Sat Jun 26 06:28:23 UTC 2021 , Edited by admin on Sat Jun 26 06:28:23 UTC 2021
PRIMARY
FDA UNII
8J337D1HZY
Created by admin on Sat Jun 26 06:28:23 UTC 2021 , Edited by admin on Sat Jun 26 06:28:23 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-749-5
Created by admin on Sat Jun 26 06:28:23 UTC 2021 , Edited by admin on Sat Jun 26 06:28:23 UTC 2021
PRIMARY
NCI_THESAURUS
C410
Created by admin on Sat Jun 26 06:28:23 UTC 2021 , Edited by admin on Sat Jun 26 06:28:23 UTC 2021
PRIMARY
MERCK INDEX
M4062
Created by admin on Sat Jun 26 06:28:23 UTC 2021 , Edited by admin on Sat Jun 26 06:28:23 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
CYTOSINE
Created by admin on Sat Jun 26 06:28:23 UTC 2021 , Edited by admin on Sat Jun 26 06:28:23 UTC 2021
PRIMARY
EPA CompTox
71-30-7
Created by admin on Sat Jun 26 06:28:23 UTC 2021 , Edited by admin on Sat Jun 26 06:28:23 UTC 2021
PRIMARY
PUBCHEM
597
Created by admin on Sat Jun 26 06:28:23 UTC 2021 , Edited by admin on Sat Jun 26 06:28:23 UTC 2021
PRIMARY
USP_CATALOG
1162148
Created by admin on Sat Jun 26 06:28:23 UTC 2021 , Edited by admin on Sat Jun 26 06:28:23 UTC 2021
PRIMARY USP-RS
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
PARENT -> IMPURITY
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY