Adenine
Basic information
- CAS
73-24-5- Standard SMILES
Nc1ncnc2nc[nH]c12- InChIKey
GFFGJBXGBJISGV-UHFFFAOYSA-N- Molecular formula
- C5H5N5
- Average molar mass
- 135.13 g/mol
- Monoisotopic mass
- 135.05449518
Overview
Adenine is the parent compound of the 6-aminopurines, composed of a purine having an amino group at C-6. It has a role as a mouse metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite, a human metabolite and a Daphnia magna metabolite. It is a member of 6-aminopurines and a purine nucleobase. It derives from a hydride of a 9H-purine.
Names & identifiers
- Preferred name
- Adenine
- IUPAC
- 7H-purin-6-amine
- English name
- Adenine
- Molecular formula
- C5H5N5
- Molecular weight
- 135.13
Names & synonyms
adenine73-24-56-Aminopurine1H-Purin-6-amine7H-Purin-6-amineAdeninimineAdeninLeuco-46-Amino-1H-purine6-Amino-7H-purine6-Amino-9H-purine6-Amino-3H-purine
Show more names
9H-Purin-6-amineAdeVitamin B4ANEPurin-6-amine
1,6-Dihydro-6-iminopurine3,6-Dihydro-6-iminopurineDTXSID6022557NSC-14666CHEBI:16708JAC85A2161DTXCID502557NSC14666
Database identifiers
- CAS
73-24-5- PubChem CID
- 190
- DTXSID
DTXSID6022557- ChEMBL
CHEMBL1797130、CHEMBL226345、CHEMBL539503- ChEBI
CHEBI:16708- UNII
- JAC85A2161
- EC Number
- 200-796-1
- Nikkaji
- J5.257D
Properties
Computed structural properties
- XLogP
- -0.1
- Topological polar surface area
- 80.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 0
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 127
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials Properties15N nuclear magnetic resonance spectrum
LogP
-0.09
-0.05
Solubility
1.03 mg/mL
>20.3 [ug/mL] (The mean of the results at pH 7.4)
Melting Point360 °C
Physical DescriptionSolid
Ionization Efficiency
Positive
2.88
2.7
Agilent XCT
Electrospray ionization
formic acid (5.3nM)
Dissociation Constants4.15 (at 25 °C)
Collision Cross Section
125.2 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID6022557]
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (96.8%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 349 reports by companies from 10 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Chemical: 1H-Purin-6-amine
REACH registered substance: Adenine (EC: 200-796-1)
Adenine: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - 1H-Purin-6-amine: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 3 (96.8%)
Toxicology
Toxicity Summary
Adenine 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
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Safety data
Chemistry & industry
Pharmacology
Pharmacodynamics
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.
Mechanism of Action
Adenine forms adenosine, a nucleoside, when attached to ribose, and deoxyadenosine when attached to deoxyribose, and it forms adenosine triphosphate (ATP), which drives many cellular metabolic processes by transferring chemical energy between reactions.
Tissue LocationsAll Tissues
Cellular LocationsCytoplasm
Metabolite PathwaysAdenine phosphoribosyltransferase deficiency (APRT)
Uses & manufacturing
UsesFor nutritional supplementation, also for treating dietary shortage or imbalance
General Manufacturing Information9H-Purin-6-amine: ACTIVE
Applications
adenine is one of the purine nitrogenous bases that composes DNA and RNA; composed of two carbon–nitrogen rings. Adenine bonds with thymine in DNA and with uracil in RNA (see base pairing rule); it is also a major component of other molecules such as adenosine triphosphate.
Related reactions
202 records
Compound notes
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