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Showing Compound Adenine (FDB012266)

Record Information
Version1.0
Creation date2010-04-08 22:10:05 UTC
Update date2019-11-26 03:06:30 UTC
Primary IDFDB012266
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAdenine
DescriptionWidespread throughout animal and plant tissue, purine components of DNA, RNA, and coenzymes. Vitamin Adenine (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.; Adenine forms adenosine, a nucleoside, when attached to ribose, and deoxyadenosine when attached to deoxyribose. 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 chemical reactions.; Adenine is a nucleobase (a purine derivative) with 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), and protein synthesis, as a chemical component of DNA and RNA. The shape of adenine is complementary to either thymine in DNA or uracil in RNA.; Adenine is a purine base. Adenine is found in both DNA and RNA. Adenine is a fundamental component of adenine nucleotides. Adenine forms adenosine, a nucleoside, when attached to ribose, and deoxyadenosine when attached to deoxyribose; Adenine is one of the two purine nucleobases (the other being guanine) used in forming nucleotides of the nucleic acids. In DNA, adenine binds to thymine via two hydrogen bonds to assist in stabilizing the nucleic acid structures. In RNA, which is used in the cytoplasm for protein synthesis, adenine binds to uracil.; In older literature, adenine was sometimes called Vitamin B4. It is no longer considered a true vitamin or part of the Vitamin B complex. However, two B vitamins, niacin and riboflavin, bind with adenine to form the essential cofactors nicotinamide adenine dinucleotide (NAD) and flavin adenine dinucleotide (FAD), respectively. Hermann Emil Fischer was one of the early scientists to study Adenine.; 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 chemical reactions.; Purine inborn errors of metabolism (IEM) are serious hereditary disorders, which should be suspected in any case of neonatal fitting, failure to thrive, recurrent infections, neurological deficit, renal disease, self-mutilation and other manifestations. Investigation usually starts with uric acid (UA) determination in urine and plasma. (OMIM 300322, 229600, 603027, 232400, 232600, 232800, 201450, 220150, 232200, 162000, 164050, 278300). (PMID: 17052198, 17520339).
CAS Number73-24-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
1,6-Dihydro-6-iminopurinebiospider
1h-purin-6-aminebiospider
1H-Purin-6-amine (9CI)biospider
1H-Purin-6-amine, 9CIdb_source
1H-Purine-6-aminebiospider
1H-Purine, 6-aminobiospider
1H-Purine, 6-amino-biospider
2-aminopurinebiospider
2'-DEOXY-ADENOSINE-3'-5'-DIPHOSPHATEbiospider
3, 6-Dihydro-6-iminopurinebiospider
3,6-Dihydro-6-iminopurinebiospider
4, Vitamin Bbiospider
6-Amino-1H-purinebiospider
6-Amino-3H-purinebiospider
6-Amino-7H-purinebiospider
6-Amino-9H-purinebiospider
6-amino-Purinebiospider
6-Aminopurinedb_source
7H-Purin-6-aminebiospider
9H-Purin-6-aminebiospider
9H-Purin-6-yl-aminbiospider
9H-purin-6-ylaminebiospider
9H-Purine-6-aminebiospider
9H-Purine, 1, 6-dihydro-6-imino-biospider
9H-Purine, 1,6-dihydro-6-imino-biospider
A, ade, adeniniminebiospider
ABGbiospider
ADEbiospider
Adeninbiospider
Adenine (8CI)biospider
Adenine (jan/usp)biospider
Adenine (van )biospider
Adenine (van)biospider
Adenine [jan]biospider
Adenine-8-14Cbiospider
Adenine-ringbiospider
Adeniniminebiospider
ANEbiospider
ANPbiospider
B 4, Vitaminbiospider
Leuco-4biospider
Leuconbiospider
Leucon (TN)biospider
Pedatisectine bbiospider
Purine, 6-amino-biospider
Vitamin B 4biospider
Vitamin B4db_source
Predicted Properties
PropertyValueSource
Water Solubility2.42 g/LALOGPS
logP-1.4ALOGPS
logP-0.53ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)5.59ChemAxon
pKa (Strongest Basic)3.22ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.48 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity36.6 m³·mol⁻¹ChemAxon
Polarizability12.39 ųChemAxon
Number of Rings8ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H20N20
IUPAC nametetrakis(3H-purin-6-amine)
InChI IdentifierInChI=1S/4C5H5N5/c4*6-4-3-5(9-1-7-3)10-2-8-4/h4*1-2H,(H3,6,7,8,9,10)
InChI KeyZSIFYVSPMACPJY-UHFFFAOYSA-N
Isomeric SMILESNC1=C2N=CN=C2N=CN1.NC1=NC=NC2=C1NC=N2.NC1=NC=NC2=C1N=CN2.NC1=C2N=CN=C2NC=N1
Average Molecular Weight540.5068
Monoisotopic Molecular Weight540.21798074
Classification
Description Belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct Parent6-aminopurines
Alternative Parents
Substituents
  • 6-aminopurine
  • Aminopyrimidine
  • Imidolactam
  • Pyrimidine
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkNot Available
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 44.44%; H 3.73%; N 51.83%DFC
Melting PointMp 360-365 (anhyd.)° dec.DFC
Boiling PointNot Available
Experimental Water Solubility1.03 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP-0.09HANSCH,C ET AL. (1995)
Experimental pKapKa2 9.83 (25°)DFC
Isoelectric pointNot Available
Charge0
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID185
ChEMBL IDCHEMBL226345
KEGG Compound IDC00147
Pubchem Compound ID190
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB00173
HMDB IDHMDB00034
CRC / DFC (Dictionary of Food Compounds) IDHFN72-P:HFN72-P
EAFUS IDNot Available
Dr. Duke IDADENINE
BIGG ID34039
KNApSAcK IDC00001490
HET IDADE
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDAdenine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Anti-anemic52217 An agent that treats or prevents anemia by increasing red blood cell production or enhancing iron utilization, commonly used to manage iron-deficiency anemia, vitamin deficiency anemia, and other blood disorders, promoting healthy oxygen delivery to tissues and organs.DUKE
Anti granulocytopenicAn agent that stimulates granulocyte production, reducing the risk of infection. It is used to treat conditions like neutropenia, increasing white blood cell count and preventing infections in patients undergoing chemotherapy or with bone marrow disorders.DUKE
Anti-viral22587 An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19.DUKE
Central nervous system stimulant35470 An agent that increases alertness and activity by enhancing neurotransmitter release, used therapeutically to manage attention deficit hyperactivity disorder (ADHD), narcolepsy, and fatigue, and to improve cognitive function and mood.DUKE
Diuretic35498 An agent that increases urine production, helping remove excess fluids and salts from the body. It plays a key biological role in regulating fluid balance and blood pressure. Therapeutically, diuretics are used to treat conditions such as hypertension, edema, and heart failure, helping reduce swelling and lower blood pressure.DUKE
HyperuricemicAn agent that increases uric acid levels in the blood, playing a role in gout development. Therapeutically, it has limited applications, but is used in research to study gout and uric acid metabolism. Medically, it is used to induce gout-like conditions in clinical trials, aiding in the development of treatments for gout and other uric acid-related disorders.DUKE
Insectifuge24852 A substance that repels insects, playing a biological role in plant defense. Therapeutically, it has applications in preventing insect-borne diseases. Key medical uses include topical repellents for malaria, dengue fever, and other vector-borne illnesses, reducing the risk of transmission.DUKE
LithogenicAn agent that promotes the formation of calculi (kidney stones), playing a role in certain biological processes. Therapeutically, it has limited applications, but is used in research to study kidney stone formation. Medically, understanding lithogenic factors is crucial in preventing and managing kidney stone disease, allowing for targeted interventions to reduce stone formation and recurrence.DUKE
Myocardiotonic38070 An agent that strengthens heart muscle contractions, enhancing cardiac function. It plays a biological role in increasing cardiac output and reducing symptoms of heart failure. Therapeutically, myocardiotonics are used to manage conditions like cardiomyopathy, heart failure, and coronary artery disease, improving overall cardiac performance.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
Vasodilator35620 An agent that widens blood vessels, reducing blood pressure and increasing blood flow. It plays a biological role in regulating cardiovascular function. Therapeutically, vasodilators are used to treat conditions such as hypertension, angina, and heart failure, improving oxygen delivery and reducing cardiac workload.DUKE
Enzymes
NameGene NameUniProt ID
Purine nucleoside phosphorylasePNPP00491
S-methyl-5'-thioadenosine phosphorylaseMTAPQ13126
Equilibrative nucleoside transporter 2SLC29A2Q14542
Adenine phosphoribosyltransferaseAPRTP07741
Peroxisomal trans-2-enoyl-CoA reductasePECRQ9BY49
Equilibrative nucleoside transporter 3SLC29A3Q9BZD2
Pathways
NameSMPDB LinkKEGG Link
Purine MetabolismSMP00050 map00230
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.