ADENINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C5H5N5
Molecular Weight	135.1267
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=NC=NC2=C1N=CN2

InChI

InChIKey=GFFGJBXGBJISGV-UHFFFAOYSA-N

InChI=1S/C5H5N5/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H3,6,7,8,9,10)

HIDE SMILES / InChI

Molecular Formula	C5H5N5
Molecular Weight	135.1267
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.drugbank.ca/drugs/DB00173
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/25797921 | https://www.ncbi.nlm.nih.gov/pubmed/9046330 | https://www.ncbi.nlm.nih.gov/pubmed/2165159 | https://www.ncbi.nlm.nih.gov/pubmed/27776394 | https://www.ncbi.nlm.nih.gov/pubmed/26243842

Adenine is a nucleobase (a purine derivative). Its derivatives have a variety of roles in biochemistry including cellular respiration, in the form of both the energy-rich adenosine triphosphate (ATP) and the cofactors nicotinamide adenine dinucleotide (NAD) and flavin adenine dinucleotide (FAD). It also has functions in protein synthesis and as a chemical component of DNA and RNA. The shape of adenine is complementary to either thymine in DNA or uracil in RNA

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Phosphatidylinositol 4-kinase, PI4K 6 Target ID: CHEMBL2096619 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2165159	Inhibitor 8297	85.8 µM [Ki]
Cyclin-dependent kinase 1 27 Target ID: CHEMBL308 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9046330	Inhibitor 8297	200.0 µM [IC50]
Xanthine dehydrogenase 32 Target ID: CHEMBL1929 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17379526	Inhibitor 8297	10.89 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
preparation of red blood cells 5 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=fdd00e7b-039a-48a8-b654-941f85f5c00f	Diagnostic	Approved 8429	LEUKOTRAP WB SYSTEM Approved Use Indicated for collection of blood and preparation of red blood cells and plasma with pre-storage leukocyte reduction. Platelet concentrates are not intended to be made with this product.
Leukopenia associated with an overdose of antipsychotics 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27776394	Secondary	Not Provided 504	Unknown Approved Use Unknown
Neutropenia associated with an overdose of antipsychotics 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27776394	Secondary	Not Provided 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Influence of a probiotic yoghurt on the status of vitamins B(1), B(2) and B(6) in the healthy adult human.	2001	11244182
Capillary affinity gel electrophoresis.	2001	11242958
UAG readthrough in mammalian cells: effect of upstream and downstream stop codon contexts reveal different signals.	2001	11242562
Metabolic fate of extracellular NAD in human skin fibroblasts.	2001	11135366
Cloning of dimethylglycine dehydrogenase and a new human inborn error of metabolism, dimethylglycine dehydrogenase deficiency.	2001 Apr	11231903
Quantum-chemical analysis of C-H...O and C-H...N interactions in RNA base pairs--H-bond versus anti-H-bond pattern.	2001 Feb	11245250
Mechanisms and modulation of intestinal epithelial repair.	2001 Feb	11233665
NO Inhibits NaCl absorption by rat thick ascending limb through activation of cGMP-stimulated phosphodiesterase.	2001 Feb	11230320
Inhibition of human squalene monooxygenase by tellurium compounds: evidence of interaction with vicinal sulfhydryls.	2001 Feb	11181753
Structure of the electron transfer complex between ferredoxin and ferredoxin-NADP(+) reductase.	2001 Feb	11175898
A Taq attack displaces bases.	2001 Feb	11175890
Crystallization and preliminary X-ray analysis of a DNA dodecamer containing 2'-deoxy-5-formyluridine; what is the role of magnesium cation in crystallization of Dickerson-type DNA dodecamers?	2001 Feb	11173500
De novo mutation in the mitochondrial tRNALeu(UUR) gene (A3243G) with rapid segregation resulting in MELAS in the offspring.	2001 Feb	11168879
Origin of the cytoplasmic pH changes during anaerobic stress in higher plant cells. Carbon-13 and phosphorous-31 nuclear magnetic resonance studies.	2001 Feb	11161048
PTH and PTH-related peptide enhance steroid secretion from human adrenocortical cells.	2001 Feb	11158922
RIZ, the retinoblastoma protein interacting zinc finger gene, is mutated in genetically unstable cancers of the pancreas, stomach, and colorectum.	2001 Feb	11135439
Apoptosis induction by the photosensitizer verteporfin: identification of mitochondrial adenine nucleotide translocator as a critical target.	2001 Feb 15	11245415
"Chemical preconditioning" by 3-nitropropionate reduces ischemia-reperfusion injury in cardiac-arrested rat lungs.	2001 Feb 15	11233893
In situ kinetic characterization of methylthioadenosine transport by the adenosine transporter (P2) of the African Trypanosoma brucei brucei and Trypanosoma brucei rhodesiense.	2001 Feb 15	11226379
Crystal structure of human cyclin-dependent kinase 2 in complex with the adenine-derived inhibitor H717.	2001 Feb 15	11170642
Seven new mutations in the nicotinamide adenine dinucleotide reduced-cytochrome b(5) reductase gene leading to methemoglobinemia type I.	2001 Feb 15	11159544
Cytomegalovirus infection increases the expression and activity of ecto-ATPase (CD39) and ecto-5'nucleotidase (CD73) on endothelial cells.	2001 Feb 23	11226411
Anatomy of a preferred target site for the bacterial insertion sequence IS903.	2001 Feb 23	11178901
Thermodynamics of ion-induced RNA folding in the hammerhead ribozyme: an isothermal titration calorimetric study.	2001 Feb 6	11170470
Phosphorescence and optically detected magnetic resonance of HIV-1 nucleocapsid protein complexes with stem-loop sequences of the genomic Psi-recognition element.	2001 Feb 6	11170468
Anti-gene effect in live cells of AG motif triplex-forming oligonucleotides containing an increasing number of phosphorothioate linkages.	2001 Feb 6	11170438
Reduced hydrolysis of amelogenin may result in X-linked amelogenesis imperfecta.	2001 Jan	11223334
Duck hepatitis B virus polymerase gene mutants associated with resistance to lamivudine have a decreased replication capacity in vitro and in vivo.	2001 Jan	11211887
Quantum chemistry predicted correlations between geometric isomerism (conformation) of -OH and =NH substituents and typical group frequencies of nucleic acid bases: cytosine.	2001 Jan	11209867
Extracellular ATP formation on vascular endothelial cells is mediated by ecto-nucleotide kinase activities via phosphotransfer reactions.	2001 Jan	11149913
Evolutionary optimization of metabolic pathways. Theoretical reconstruction of the stoichiometry of ATP and NADH producing systems.	2001 Jan	11146883
Developmental potential and transgene expression of porcine nuclear transfer embryos using somatic cells.	2001 Jan	11144215
A functional genomics strategy that uses metabolome data to reveal the phenotype of silent mutations.	2001 Jan	11135551
A novel response of cancer cells to radiation involves autophagy and formation of acidic vesicles.	2001 Jan 15	11212227
Activation of the insulin receptor's kinase domain changes the rate-determining step of substrate phosphorylation.	2001 Jan 16	11148045
2-Alkynyl-8-aryl-9-methyladenines as novel adenosine receptor antagonists: their synthesis and structure-activity relationships toward hepatic glucose production induced via agonism of the A(2B) receptor.	2001 Jan 18	11170626
Codon bias at the 3'-side of the initiation codon is correlated with translation initiation efficiency in Escherichia coli.	2001 Jan 24	11223267
Probing structure and dynamics of DNA with 2-aminopurine: effects of local environment on fluorescence.	2001 Jan 30	11170416
Regulation of protein degradation and protease expression by mannose in maize root tips. Pi sequestration by mannose may hinder the study of its signaling properties.	2001 Mar	11244127
2,8-Dihydroxyadenine urolithiasis in a patient with considerable residual adenine phosphoribosyltransferase activity in cell extracts but with mutations in both copies of APRT.	2001 Mar	11243733
Escherichia coli FtsH (HflB) degrades a membrane-associated TolAI-II-beta-lactamase fusion protein under highly denaturing conditions.	2001 Mar	11237695
Polymorphism of the WAF1 gene is related to susceptibility to cervical cancer in Japanese women.	2001 Mar	11179504
Adenosine signaling in outer medullary descending vasa recta.	2001 Mar	11171666
cAMP-independent phosphorylation activation of CFTR by G proteins in native human sweat duct.	2001 Mar	11171580
Efficiency comparisons of rank and permutation tests based on summary statistics computed from repeated measures data.	2001 Mar 15	11241572
Role of adenosine kinase in Saccharomyces cerevisiae: identification of the ADO1 gene and study of the mutant phenotypes.	2001 Mar 15	11223943
A(1) or A(3) adenosine receptors induce late preconditioning against infarction in conscious rabbits by different mechanisms.	2001 Mar 16	11249876
Specific labeling of the bovine heart mitochondrial phosphate carrier with fluorescein 5-isothiocyanate: roles of Lys185 and putative adenine nucleotide recognition site in phosphate transport.	2001 Mar 30	11133984
Expression and mutagenesis of the NqrC subunit of the NQR respiratory Na(+) pump from Vibrio cholerae with covalently attached FMN.	2001 Mar 9	11248234
Solution structure of an A-tract DNA bend.	2001 Mar 9	11237619

Patents

Sample Use Guides

In Vivo Use Guide

the daily dose of adenine is 10-60 mg/day

Route of Administration: Oral

In Vitro Use Guide

NIH/3T3 cells were plated at a density of 2 × 106 cells and left untreated overnight, cultural media was exchanged and experimental plates were exposed to adenine (200 -1200 mkM) for 24 hr. Cells were counted at various concentration of adenine or AICAR with a hemocytometer after diluting the sample 1:1 with 0.4% trypan blue solution (Sigma-Aldrich, St. Louis, MO, USA). Alternatively, the cell cytotoxicity of the cells was monitored with XTT assay. 50 μL of XTT reagent was added and the plates were then incubated for 4 hr at 37 °C in the dark. The absorbance at 490 nm with a reference wavelength set at 690 nm using VersaMax ELISA microplate reader

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:02:23 GMT 2023` Edited by `admin` on `Fri Dec 15 15:02:23 GMT 2023`
Record UNII	JAC85A2161
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

ADENINE

Official Name

English

NSC-14666

Code

English

ADENINE [MART.]

Common Name

English

7H-PURIN-6-AMINE

Systematic Name

English

ADENINE [USP MONOGRAPH]

Common Name

English

ADENINE [JAN]

Common Name

English

1H-PURIN-6-AMINE

Systematic Name

English

ADENOSINE IMPURITY A [EP IMPURITY]

Common Name

English

1,6-Dihydro-6-iminopurine

Systematic Name

English

ADENINE [VANDF]

Common Name

English

ADENINE [MI]

Common Name

English

ADENINE [USP IMPURITY]

Common Name

English

Adenine [WHO-DD]

Common Name

English

ADENINE [INCI]

Common Name

English

ADENINE [USP-RS]

Common Name

English

ADENINE [EP MONOGRAPH]

Common Name

English

Classification Tree Code System Code

LOINC

75133-9

Created by admin on Fri Dec 15 15:02:24 GMT 2023 , Edited by admin on Fri Dec 15 15:02:24 GMT 2023

LOINC

75131-3

Created by admin on Fri Dec 15 15:02:24 GMT 2023 , Edited by admin on Fri Dec 15 15:02:24 GMT 2023

LOINC

1719-4

Created by admin on Fri Dec 15 15:02:24 GMT 2023 , Edited by admin on Fri Dec 15 15:02:24 GMT 2023

LOINC

59203-0

Created by admin on Fri Dec 15 15:02:24 GMT 2023 , Edited by admin on Fri Dec 15 15:02:24 GMT 2023

NCI_THESAURUS

C786

Created by admin on Fri Dec 15 15:02:24 GMT 2023 , Edited by admin on Fri Dec 15 15:02:24 GMT 2023

FDA ORPHAN DRUG

917122

Created by admin on Fri Dec 15 15:02:23 GMT 2023 , Edited by admin on Fri Dec 15 15:02:23 GMT 2023

Code System Code Type Description

ECHA (EC/EINECS)

200-796-1

Created by admin on Fri Dec 15 15:02:23 GMT 2023 , Edited by admin on Fri Dec 15 15:02:23 GMT 2023

PRIMARY

NSC

14666

Created by admin on Fri Dec 15 15:02:24 GMT 2023 , Edited by admin on Fri Dec 15 15:02:24 GMT 2023

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RXCUI

290

Created by admin on Fri Dec 15 15:02:24 GMT 2023 , Edited by admin on Fri Dec 15 15:02:24 GMT 2023

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RxNorm

EPA CompTox

DTXSID6022557

Created by admin on Fri Dec 15 15:02:23 GMT 2023 , Edited by admin on Fri Dec 15 15:02:23 GMT 2023

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CHEBI

16708

Created by admin on Fri Dec 15 15:02:23 GMT 2023 , Edited by admin on Fri Dec 15 15:02:23 GMT 2023

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MESH

D000225

Created by admin on Fri Dec 15 15:02:24 GMT 2023 , Edited by admin on Fri Dec 15 15:02:24 GMT 2023

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CAS

73-24-5

Created by admin on Fri Dec 15 15:02:23 GMT 2023 , Edited by admin on Fri Dec 15 15:02:23 GMT 2023

PRIMARY

EVMPD

SUB12455MIG

Created by admin on Fri Dec 15 15:02:23 GMT 2023 , Edited by admin on Fri Dec 15 15:02:23 GMT 2023

PRIMARY

ChEMBL

CHEMBL226345

Created by admin on Fri Dec 15 15:02:23 GMT 2023 , Edited by admin on Fri Dec 15 15:02:23 GMT 2023

PRIMARY

MERCK INDEX

m1410

Created by admin on Fri Dec 15 15:02:24 GMT 2023 , Edited by admin on Fri Dec 15 15:02:24 GMT 2023

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Merck Index

SMS_ID

100000078775

Created by admin on Fri Dec 15 15:02:24 GMT 2023 , Edited by admin on Fri Dec 15 15:02:24 GMT 2023

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FDA UNII

JAC85A2161

Created by admin on Fri Dec 15 15:02:23 GMT 2023 , Edited by admin on Fri Dec 15 15:02:23 GMT 2023

PRIMARY

WIKIPEDIA

ADENINE

Created by admin on Fri Dec 15 15:02:24 GMT 2023 , Edited by admin on Fri Dec 15 15:02:24 GMT 2023

PRIMARY

PUBCHEM

190

Created by admin on Fri Dec 15 15:02:24 GMT 2023 , Edited by admin on Fri Dec 15 15:02:24 GMT 2023

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NCI_THESAURUS

C206

Created by admin on Fri Dec 15 15:02:24 GMT 2023 , Edited by admin on Fri Dec 15 15:02:24 GMT 2023

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DAILYMED

JAC85A2161

Created by admin on Fri Dec 15 15:02:23 GMT 2023 , Edited by admin on Fri Dec 15 15:02:23 GMT 2023

PRIMARY

DRUG CENTRAL

89

Created by admin on Fri Dec 15 15:02:23 GMT 2023 , Edited by admin on Fri Dec 15 15:02:23 GMT 2023

PRIMARY

RS_ITEM_NUM

1012101

Created by admin on Fri Dec 15 15:02:24 GMT 2023 , Edited by admin on Fri Dec 15 15:02:24 GMT 2023

PRIMARY

DRUG BANK

DB00173

Created by admin on Fri Dec 15 15:02:23 GMT 2023 , Edited by admin on Fri Dec 15 15:02:23 GMT 2023

PRIMARY

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Details

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Approved Use

Approved Use

PubMed

Patents

Sample Use Guides