Record Information
Version1.0
Creation date2015-10-09 22:27:36 UTC
Update date2017-01-19 02:36:10 UTC
FoodComEx IDPC000036
FoodDB RecordFDB012266
Chemical Information
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
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
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
Chemical Taxonomy
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
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logP-0.09HANSCH,C ET AL. (1995)
Experimental Water Solubility1.03 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting PointMp 360-365 (anhyd.)° dec.DFC
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 500 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci D124
AKSci J20020
AKSci J70183
AKSci J90580
AKSci HMDB0000034
Glentham GE7863
MetaSci HMDB0000034
Toronto Research Chemicals A280480