FComEx: Adenine (PC000036)

Record Information

Version

1.0

Creation date

2015-10-09 22:27:36 UTC

Update date

2017-01-19 02:36:10 UTC

FoodComEx ID

PC000036

FoodDB Record

FDB012266

Chemical Information

Name

Adenine

Description

Widespread 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 Number

73-24-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1,6-Dihydro-6-iminopurine	biospider
1h-purin-6-amine	biospider
1H-Purin-6-amine (9CI)	biospider
1H-Purin-6-amine, 9CI	db_source
1H-Purine-6-amine	biospider
1H-Purine, 6-amino	biospider
1H-Purine, 6-amino-	biospider
2-aminopurine	biospider
2'-DEOXY-ADENOSINE-3'-5'-DIPHOSPHATE	biospider
3, 6-Dihydro-6-iminopurine	biospider
3,6-Dihydro-6-iminopurine	biospider
4, Vitamin B	biospider
6-Amino-1H-purine	biospider
6-Amino-3H-purine	biospider
6-Amino-7H-purine	biospider
6-Amino-9H-purine	biospider
6-amino-Purine	biospider
6-Aminopurine	db_source
7H-Purin-6-amine	biospider
9H-Purin-6-amine	biospider
9H-Purin-6-yl-amin	biospider
9H-purin-6-ylamine	biospider
9H-Purine-6-amine	biospider
9H-Purine, 1, 6-dihydro-6-imino-	biospider
9H-Purine, 1,6-dihydro-6-imino-	biospider
A, ade, adeninimine	biospider
ABG	biospider
ADE	biospider
Adenin	biospider
Adenine (8CI)	biospider
Adenine (jan/usp)	biospider
Adenine (van )	biospider
Adenine (van)	biospider
Adenine [jan]	biospider
Adenine-8-14C	biospider
Adenine-ring	biospider
Adeninimine	biospider
ANE	biospider
ANP	biospider
B 4, Vitamin	biospider
Leuco-4	biospider
Leucon	biospider
Leucon (TN)	biospider
Pedatisectine b	biospider
Purine, 6-amino-	biospider
Vitamin B 4	biospider
Vitamin B4	db_source

Chemical Formula

C20H20N20

IUPAC name

tetrakis(3H-purin-6-amine)

InChI Identifier

InChI=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 Key

ZSIFYVSPMACPJY-UHFFFAOYSA-N

Isomeric SMILES

NC1=C2N=CN=C2N=CN1.NC1=NC=NC2=C1NC=N2.NC1=NC=NC2=C1N=CN2.NC1=C2N=CN=C2NC=N1

Average Molecular Weight

540.5068

Monoisotopic Molecular Weight

540.21798074

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

6-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 Framework

Not Available

External Descriptors

Not Available

Physico-Chemical Properties - Experimental

Property	Value	Reference
Experimental logP	-0.09	HANSCH,C ET AL. (1995)
Experimental Water Solubility	1.03 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting Point	Mp 360-365 (anhyd.)° dec.	DFC

Foods of Origin