Record Information
Version1.0
Creation date2010-04-08 22:10:05 UTC
Update date2018-05-28 23:35:31 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
Synonyms
SynonymSource
6-AminopurineChEBI
AChEBI
AdeChEBI
AdeninChEBI
1,6-dihydro-6-IminopurineHMDB
1H-Purin-6-amineHMDB
1H-Purine-6-amineHMDB
3,6-dihydro-6-IminopurineHMDB
6-amino-1H-PurineHMDB
6-amino-3H-PurineHMDB
6-amino-7H-PurineHMDB
6-amino-9H-PurineHMDB
6-amino-PurineHMDB
9H-Purin-6-amineHMDB
9H-Purin-6-yl-aminHMDB
9H-Purin-6-ylamineHMDB
9H-Purine-6-amineHMDB
AdeninimineHMDB
Vitamin b4HMDB
Vitamin b 4MeSH
4, Vitamin bMeSH
b 4, VitaminMeSH
1,6-Dihydro-6-iminopurinebiospider
1h-purin-6-aminebiospider
1H-Purin-6-amine (9CI)biospider
1H-Purin-6-amine, 9CIdb_source
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
7H-Purin-6-aminebiospider
9H-purin-6-ylaminebiospider
9H-Purine, 1, 6-dihydro-6-imino-biospider
9H-Purine, 1,6-dihydro-6-imino-biospider
A, ade, adeniniminebiospider
ABGbiospider
ADEbiospider
Adenine (8CI)biospider
Adenine (jan/usp)biospider
Adenine (van )biospider
Adenine (van)biospider
Adenine [jan]biospider
Adenine-8-14Cbiospider
Adenine-ringbiospider
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
logP-0.57ChemAxon
pKa (Strongest Acidic)6.21ChemAxon
pKa (Strongest Basic)1.36ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.48 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity38.22 m³·mol⁻¹ChemAxon
Polarizability12.29 ųChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H20N20
IUPAC name1H-purin-6-amine; 3H-purin-6-amine; 7H-purin-6-amine; 9H-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
DescriptionThis compound 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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
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
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-03di-3490000000-7efe9518c90307a43707View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-03di-2690000000-6dc072eb8483a2c38e18View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00di-9350000000-220125189c286547e86cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-03di-4690000000-2d327a6944df53411886View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0006-3920000000-f488e8aa64272a07b3d9View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-000i-0329000000-0b012fa483ce8764d2afView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-03di-3490000000-7efe9518c90307a43707View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-03di-2690000000-6dc072eb8483a2c38e18View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9350000000-220125189c286547e86cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-03di-4690000000-2d327a6944df53411886View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0006-3920000000-f488e8aa64272a07b3d9View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000i-0329000000-0b012fa483ce8764d2afView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-03di-2690000000-534edabc8ab24e32f3f5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a5i-9700000000-e85c2b0bb19cf3401e5aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0900000000-95d4894082ada0b24773View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-5900000000-66b1c086d7a666b2d02bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9200000000-4202a1aec437f3fd1275View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-c1766360e5f779d277abView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-68585e8dac03a15d5210View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0900000000-3db475b164c0f884b93dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-2900000000-7e2deed118def434e8dbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-0900000000-b24b09629456779d96e6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000i-0900000000-b2cc6b5ce2fe2affe47dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-000i-0900000000-f45a65a00be3c0c36350View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0900000000-80808f34c7497219d349View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-0a5c-6900000000-f6c0abd6d3fca61bd7f7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0900000000-b24b09629456779d96e6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-80808f34c7497219d349View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a5c-6900000000-f6c0abd6d3fca61bd7f7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-001i-0900000000-cbe0a995dab473351f43View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-001i-0900000000-bfc42d662f222a7c16c7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0900000000-3db475b164c0f884b93dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-2900000000-7e2deed118def434e8dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-f2335984e7dd7e129a8cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-ee084d257bf2325fb370View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-067i-9700000000-5a42850e3f5331952458View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-05fa9674ab4d9e5e174eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-dc404aa4196bbf0ae9cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05o0-8900000000-b56d110371cd80ac76e0View in MoNA
MSMass Spectrum (Electron Ionization)splash10-000i-6900000000-39944576233751576a91View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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
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 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti granulocytopenicDUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
central nervous system stimulant35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
hyperuricemicDUKE
insectifuge24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
lithogenicDUKE
myocardiotonic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
vasodilator35620 A drug used to cause dilation of the blood vessels.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.