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Identification
NameAdenine
Accession NumberDB00173  (EXPT00520, NUTR00012)
Typesmall molecule
Groupsapproved, nutraceutical
Description

A purine base and a fundamental unit of adenine nucleotides. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
6-AminopurineNot AvailableNot Available
ANot AvailableNot Available
AdeNot AvailableNot Available
AdeninNot AvailableNot Available
ADENINENot AvailableNot Available
Vitamin B4Not AvailableNot Available
SaltsNot Available
Brand names
NameCompany
Leuco-4Not Available
Brand mixturesNot Available
Categories
CAS number73-24-5
WeightAverage: 135.1267
Monoisotopic: 135.054495185
Chemical FormulaC5H5N5
InChI KeyGFFGJBXGBJISGV-UHFFFAOYSA-N
InChI
InChI=1S/C5H5N5/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H3,6,7,8,9,10)
IUPAC Name
7H-purin-6-amine
SMILES
NC1=C2NC=NC2=NC=N1
Mass Specshow(7.29 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassImidazopyrimidines
SubclassPurines and Purine Derivatives
Direct parentPurines and Purine Derivatives
Alternative parentsAminopyrimidines and Derivatives; Primary Aromatic Amines; Imidazoles; Polyamines
Substituentsaminopyrimidine; primary aromatic amine; pyrimidine; azole; imidazole; polyamine; amine; primary amine; organonitrogen compound
Classification descriptionThis compound belongs to the purines and purine derivatives. These are aromatic heterocyclic compounds containing a purine moiety, which is formed a pyrimidine-ring ring fused to an imidazole ring.
Pharmacology
IndicationFor nutritional supplementation, also for treating dietary shortage or imbalance
PharmacodynamicsAdenine (sometimes known as vitamin B4) combines with the sugar ribose to form adenosine, which in turn can be bonded with from one to three phosphoric acid units, yielding AMP, ADP and ATP . These adenine derivatives perform important functions in cellular metabolism. Adenine is one of four nitrogenous bases utilized in the synthesis of nucleic acids. A modified form of adenosine monophosphate (cyclic AMP) is an imporant secondary messenger in the propagation of many hormonal stimuli. Adenine is an integral part of the structure of many coenzymes. Adenosine (adenine with a ribose group) causes transient heart block in the AV node of the heart. In individuals suspected of suffering from a supraventricular tachycardia (SVT), adenosine is used to help identify the rhythm. Certain SVTs can be successfully terminated with adenosine.
Mechanism of actionAdenine forms adenosine, a nucleoside, when attached to ribose, and deoxyadenosine when attached to deoxyribose, and it forms adenosine triphosphate (ATP), a nucleotide, when three phosphate groups are added to adenosine. Adenosine triphosphate is used in cellular metabolism as one of the basic methods of transferring chemical energy between reactions. In older literature, adenine was sometimes called Vitamin B4Not Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9733
Blood Brain Barrier + 0.9395
Caco-2 permeable - 0.5225
P-glycoprotein substrate Non-substrate 0.6835
P-glycoprotein inhibitor I Non-inhibitor 0.98
P-glycoprotein inhibitor II Non-inhibitor 0.9805
Renal organic cation transporter Non-inhibitor 0.8573
CYP450 2C9 substrate Non-substrate 0.9144
CYP450 2D6 substrate Non-substrate 0.8966
CYP450 3A4 substrate Non-substrate 0.7957
CYP450 1A2 substrate Non-inhibitor 0.6459
CYP450 2C9 substrate Non-inhibitor 0.9567
CYP450 2D6 substrate Non-inhibitor 0.988
CYP450 2C19 substrate Non-inhibitor 0.9441
CYP450 3A4 substrate Non-inhibitor 0.9246
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9024
Ames test AMES toxic 0.6746
Carcinogenicity Non-carcinogens 0.9197
Biodegradation Not ready biodegradable 0.9857
Rat acute toxicity 2.4381 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9646
hERG inhibition (predictor II) Non-inhibitor 0.906
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point360 dec °CPhysProp
water solubility1030 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-0.09HANSCH,C ET AL. (1995)
logS-2.12ADME Research, USCD
pKa4.15 (at 25 °C)KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
water solubility1.15e+01 g/lALOGPS
logP-0.38ALOGPS
logP-0.57ChemAxon
logS-1.1ALOGPS
pKa (strongest acidic)10.29ChemAxon
pKa (strongest basic)5.32ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count2ChemAxon
polar surface area80.48ChemAxon
rotatable bond count0ChemAxon
refractivity38.22ChemAxon
polarizability12.29ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
References
Synthesis Reference

Eiichi Yonemitsu, Tomiya Isshiki, Yasuhiko Kijima, “Process for preparing adenine.” U.S. Patent US4059582, issued March, 1964.

US4059582
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00034
KEGG CompoundC00147
PubChem Compound190
PubChem Substance46507319
ChemSpider185
BindingDB33218
ChEBI16708
ChEMBLCHEMBL226345
Therapeutic Targets DatabaseDAP000982
PharmGKBPA448048
HETADE
WikipediaAdenine
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSshow(72.5 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Adenine phosphoribosyltransferase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Adenine phosphoribosyltransferase P07741 Details

References:

  1. Barrett C, Alley J, Pulido JC, Spurling H, Li P, Parsons T, Mallender WD, Bembenek ME: Configuration of a scintillation proximity assay for the activity assessment of recombinant human adenine phosphoribosyltransferase. Assay Drug Dev Technol. 2006 Dec;4(6):661-9. Pubmed
  2. Di Pietro V, Perruzza I, Amorini AM, Balducci A, Ceccarelli L, Lazzarino G, Barsotti P, Giardina B, Tavazzi B: Clinical, biochemical and molecular diagnosis of a compound homozygote for the 254 bp deletion-8 bp insertion of the APRT gene suffering from severe renal failure. Clin Biochem. 2007 Jan;40(1-2):73-80. Epub 2006 Oct 19. Pubmed
  3. Katahira R, Ashihara H: Profiles of purine biosynthesis, salvage and degradation in disks of potato (Solanum tuberosum L.) tubers. Planta. 2006 Dec;225(1):115-26. Epub 2006 Jul 15. Pubmed
  4. Katahira R, Ashihara H: Role of adenosine salvage in wound-induced adenylate biosynthesis in potato tuber slices. Plant Physiol Biochem. 2006 Oct;44(10):551-5. Epub 2006 Oct 9. Pubmed
  5. Boitz JM, Ullman B: Leishmania donovani singly deficient in HGPRT, APRT or XPRT are viable in vitro and within mammalian macrophages. Mol Biochem Parasitol. 2006 Jul;148(1):24-30. Epub 2006 Mar 15. Pubmed
  6. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

2. 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: unknown

Components

Name UniProt ID Details
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Singh V, Lee JE, Nunez S, Howell PL, Schramm VL: Transition state structure of 5’-methylthioadenosine/S-adenosylhomocysteine nucleosidase from Escherichia coli and its similarity to transition state analogues. Biochemistry. 2005 Sep 6;44(35):11647-59. Pubmed
  4. Walker RD, Duerre JA: S-adenosylhomocysteine metabolism in various species. Can J Biochem. 1975 Mar;53(3):312-9. Pubmed
  5. Singh V, Schramm VL: Transition-state analysis of S. pneumoniae 5’-methylthioadenosine nucleosidase. J Am Chem Soc. 2007 Mar 14;129(10):2783-95. Epub 2007 Feb 14. Pubmed

3. Acetyl-CoA carboxylase 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Acetyl-CoA carboxylase 2 O00763 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Rasmussen JT, Rosendal J, Knudsen J: Interaction of acyl-CoA binding protein (ACBP) on processes for which acyl-CoA is a substrate, product or inhibitor. Biochem J. 1993 Jun 15;292 ( Pt 3):907-13. Pubmed
  4. Witters LA, Mendel DB, Colliton JW: Modulation of acetyl-CoA carboxylase by inhibitors of IMP dehydrogenase: implications for insulin regulation. Arch Biochem Biophys. 1987 Jan;252(1):130-5. Pubmed
  5. Itani SI, Saha AK, Kurowski TG, Coffin HR, Tornheim K, Ruderman NB: Glucose autoregulates its uptake in skeletal muscle: involvement of AMP-activated protein kinase. Diabetes. 2003 Jul;52(7):1635-40. Pubmed
  6. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

4. Low molecular weight phosphotyrosine protein phosphatase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Low molecular weight phosphotyrosine protein phosphatase P24666 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Wang S, Stauffacher CV, Van Etten RL: Structural and mechanistic basis for the activation of a low-molecular weight protein tyrosine phosphatase by adenine. Biochemistry. 2000 Feb 15;39(6):1234-42. Pubmed
  4. Magherini F, Gamberi T, Paoli P, Marchetta M, Biagini M, Raugei G, Camici G, Ramponi G, Modesti A: The in vivo tyrosine phosphorylation level of yeast immunophilin Fpr3 is influenced by the LMW-PTP Ltp1. Biochem Biophys Res Commun. 2004 Aug 20;321(2):424-31. Pubmed
  5. Ostanin K, Pokalsky C, Wang S, Van Etten RL: Cloning and characterization of a Saccharomyces cerevisiae gene encoding the low molecular weight protein-tyrosine phosphatase. J Biol Chem. 1995 Aug 4;270(31):18491-9. Pubmed
  6. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

5. Peroxisomal trans-2-enoyl-CoA reductase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Peroxisomal trans-2-enoyl-CoA reductase Q9BY49 Details

6. A/G-specific adenine glycosylase

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: unknown

Components

Name UniProt ID Details
A/G-specific adenine glycosylase P17802 Details

7. Nucleoside deoxyribosyltransferase-I

Kind: protein

Organism: Lactobacillus helveticus

Pharmacological action: unknown

Components

Name UniProt ID Details
Nucleoside deoxyribosyltransferase-I Q8RLY5 Details

8. SRSF protein kinase 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
SRSF protein kinase 2 P78362 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

9. Holliday junction ATP-dependent DNA helicase RuvB

Kind: protein

Organism: Thermus thermophilus (strain HB8 / ATCC 27634 / DSM 579)

Pharmacological action: unknown

Components

Name UniProt ID Details
Holliday junction ATP-dependent DNA helicase RuvB Q5SL87 Details

10. DNA

Kind: nucleotide

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Simon R, Heithoff DM, Mahan MJ, Samuel CE: Tissue Selective Proinflammatory Gene Induction in Mice Infected with Wild-Type Compared to DNA Adenine Methylase- or Flagella-deficient Salmonella. Infect Immun. 2007 Sep 24;. Pubmed
  4. Ichida H, Maeda K, Ichise H, Matsuyama T, Abe T, Yoneyama K, Koba T: In silico restriction landmark genome scanning analysis of Xanthomonas oryzae pathovar oryzae MAFF 311018. Biochem Biophys Res Commun. 2007 Nov 23;363(3):852-6. Epub 2007 Sep 24. Pubmed
  5. Mamdouh W, Dong M, Kelly RE, Kantorovich LN, Besenbacher F: Coexistence of Homochiral and Heterochiral Adenine Domains at the Liquid/Solid Interface. J Phys Chem B. 2007 Oct 5;. Pubmed

11. S-methyl-5'-thioadenosine phosphorylase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
S-methyl-5'-thioadenosine phosphorylase Q13126 Details

References:

  1. Chow WA, Bedell V, Gaytan P, Borden E, Goldblum J, Hicks D, Slovak ML: Methylthioadenosine phosphorylase gene deletions are frequently detected by fluorescence in situ hybridization in conventional chondrosarcomas. Cancer Genet Cytogenet. 2006 Apr 15;166(2):95-100. Pubmed
  2. Chattopadhyay S, Zhao R, Tsai E, Schramm VL, Goldman ID: The effect of a novel transition state inhibitor of methylthioadenosine phosphorylase on pemetrexed activity. Mol Cancer Ther. 2006 Oct;5(10):2549-55. Pubmed
  3. Singh V, Schramm VL: Transition-state structure of human 5’-methylthioadenosine phosphorylase. J Am Chem Soc. 2006 Nov 15;128(45):14691-6. Pubmed

12. Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase

Kind: protein

Organism: Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)

Pharmacological action: unknown

Components

Name UniProt ID Details
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Maggio-Hall LA, Escalante-Semerena JC: Alpha-5,6-dimethylbenzimidazole adenine dinucleotide (alpha-DAD), a putative new intermediate of coenzyme B12 biosynthesis in Salmonella typhimurium. Microbiology. 2003 Apr;149(Pt 4):983-90. Pubmed
  4. Cheong CG, Escalante-Semerena JC, Rayment I: Structural investigation of the biosynthesis of alternative lower ligands for cobamides by nicotinate mononucleotide: 5,6-dimethylbenzimidazole phosphoribosyltransferase from Salmonella enterica. J Biol Chem. 2001 Oct 5;276(40):37612-20. Epub 2001 Jul 5. Pubmed
  5. Trzebiatowski JR, Escalante-Semerena JC: Purification and characterization of CobT, the nicotinate-mononucleotide:5,6-dimethylbenzimidazole phosphoribosyltransferase enzyme from Salmonella typhimurium LT2. J Biol Chem. 1997 Jul 11;272(28):17662-7. Pubmed

Enzymes

1. UDP-glucuronosyltransferase 1-1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
UDP-glucuronosyltransferase 1-1 P22309 Details

References:

  1. Nishimura Y, Maeda S, Ikushiro S, Mackenzie PI, Ishii Y, Yamada H: Inhibitory effects of adenine nucleotides and related substances on UDP-glucuronosyltransferase: structure-effect relationships and evidence for an allosteric mechanism. Biochim Biophys Acta. 2007 Nov;1770(11):1557-66. Epub 2007 Aug 8. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:08