Basic information
- Standard SMILES
Nc1ncnc2nc[nH]c12- InChIKey
GFFGJBXGBJISGV-UHFFFAOYSA-N- Molecular formula
- C5H5N5
- Average molar mass
- 135.13 g/mol
- Monoisotopic mass
- 135.05449516
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
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]
122.4 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
119 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine]
123.66 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
125.1 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
127.9 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]
Physicochemical properties
- Melting point
- 360 °C · >360 °C (lit.)
- Boiling point
- 238.81 °C · 238.81°C (rough estimate)
- Density
- 1.3795 · 1.3795 (rough estimate)
- refractive index
- 1.7 · 1.7000 (estimate)
- Flash point
- 220 °C · 220°C
- storage temp.
- 2 · 2-8°C
- solubility
- 0.5 M · 0.5 M HCl: soluble20mg/mL, Grade III, colorless to faint yellow or tan
- pka
- 4.12 · 4.12(at 25℃)
- form
- Liquid or Solid
- color
- Clear colorless to light yellow
- Odor
- Odorless
- PH Range
- 7 · 7
- biological source
- synthetic
- Water Solubility
- 0.5 g/L · 0.5 g/L (20 ºC)
- Sublimation
- 220 · 220 ºC
- Merck
- 14 · 14,152
- BRN
- 5777 · 5777
- Henry's Law Constant
- 1.3 · 1.3×109 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
- Stability
- Stable. Moisture-sensitive. Incompatible with strong oxidizing agents.
- Cosmetics Ingredients Functions
- SKIN CONDITIONING
- InChI
- 1S/C5H5N5/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H3,6,7,8,9,10)
- InChIKey
- GFFGJBXGBJISGV-UHFFFAOYSA-N
- SMILES
- Nc1ncnc2[nH]cnc12
- LogP
- -0.09 · -0.090
- CAS DataBase Reference
- 73 · 73-24-5(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- NCI Dictionary of Cancer Terms
- ADE; adenine
- FDA UNII
- 85 A2161 · JAC85A2161
- NIST Chemistry Reference
- Adenine(73-24-5)
- EPA Substance Registry System
- Adenine (73-24-5)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 75 · NA.75
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 301 · H301
- Precautionary statements
- 301 · P301+P310+P330
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- Hazard Codes
- Xn,Xi
- Risk Statements
- 22 · 22-20/21/22
- Safety Statements
- 26 · 26-36
- RIDADR
- 2811 · UN 2811 6.1/PG 3
- WGK Germany
- 3 · 3
- RTECS
- 6125000 · AU6125000
- F
- 8 · 8-10-23
- TSCA
- TSCA listed
- HazardClass
- 6.1 · 6.1
- PackingGroup
- III
- HS Code
- 29335990 · 29335990
- Storage Class
- 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- 3 Oral · Acute Tox. 3 Oral
- Toxicity
- 50 orally · LD50 orally in rats: 745 mg/kg (Philips)
- REACH Registrations
- Active
- Limited Quantities
- 5 kg · 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Safety & regulation
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
Status: Active Update: 17-12-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/25078
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
- F
- 8-10-23
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- AU6125000
- ridadr
- UN 2811 6.1/PG 3
- hs_code
- 29335990
- Toxicity
- LD50 orally in rats: 745 mg/kg (Philips)
- risk_code
- 22-20/21/22
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- Xn,Xi
- safety_code
- 26-36
- hazard_class
- 6.1
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- packing_group
- III
- Hazard statements
- H301
- Limited Quantities
- 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 3 Oral
- Precautionary statements
- P301+P310+P330
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
Descriptionadenine 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.
HistoryAdenine is one of the two purines found in DNA and RNA. The other is guanine. Adenine and guanine are called bases in reference to DNA and RNA. A nucleic acid base attached to ribose forms a ribonucleoside. Adenine combined with ribose produces the nucleoside adenosine.
UsesAdenine is used as an active component of boron-deficient media to grow yeast in order to assess whether yeast growth is stimulated by boron. It is useful as a local antiseptic and vitamin B4. Further, it is used in the microbial determination of niacin. It is also employed as a food supplement for adult rats to investigate the effects of dietary adenine overload. In addition to this, it is used in the production of nucleotides of the nucleic acids.
General DescriptionAdenine is a purine nucleobase. It is part of DNA, and RNA. Adenine is also a component of cofactors (NAD, FAD) and signaling molecules (cAMP). It is a nitrogenous base found in DNA and RNA. It is also a constituent of certain coenzymes and when combined with the sugar ribose it forms the nucleoside adenosine found in AMP, ADP, and ATP. Adenine has a purine ring structure. It is one of the major component bases ofnucleotides and the nucleic acidsDNA and RNA.
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Additional notes
DefinitionChEBI: 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 human metabolite, a Daphnia magna metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a purine nucleobase and a member of 6-aminopurines. It derives from a hydride of a 9H-purine.
Related reactions
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