Grundinformationen
- Standard-SMILES
Nc1ncnc2nc[nH]c12- InChIKey
GFFGJBXGBJISGV-UHFFFAOYSA-N- Summenformel
- C5H5N5
- Durchschnittliche Molmasse
- 135,13 g/mol
- Monoisotopische Masse
- 135,05449516
Überblick
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.
Namen und Bezeichner
- Bevorzugter Name
- Adenine
- IUPAC
- 7H-purin-6-amine
- Lokaler Name
- Adenin
- Englischer Name
- Adenine
- Summenformel
- C5H5N5
- Molmasse
- 135.13
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- 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
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -0,1
- Polarare Oberfläche (TPSA)
- 80,5 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 10
- Formalladung
- 0
- Komplexität
- 127
Experimentelle und physikochemische Eigenschaften
Solubility
1.03 mg/mL
>20.3 [ug/mL] (The mean of the results at pH 7.4)
Ionization Efficiency
Positive
2.88
2.7
Agilent XCT
Electrospray ionization
formic acid (5.3nM)
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]
Physikochemische Eigenschaften
- Schmelzpunkt
- 360 °C · >360 °C (lit.)
- Siedepunkt
- 238.81 °C · 238.81°C (rough estimate)
- Dichte
- 1.3795 · 1.3795 (rough estimate)
- Brechungsindex
- 1.7 · 1.7000 (estimate)
- Flammpunkt
- 220 °C · 220°C
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- 0.5 M · 0.5 M HCl: soluble20mg/mL, Grade III, colorless to faint yellow or tan
- pka
- 4.12 · 4.12(at 25℃)
- Aggregatzustand
- Liquid or Solid
- Farbe
- Clear colorless to light yellow
- Geruch (Odor)
- Odorless
- Biologische Quelle
- synthetic
- Wasserlöslichkeit
- 0.5 g/L · 0.5 g/L (20 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)
- Stabilität
- Stable. Moisture-sensitive. Incompatible with strong oxidizing agents.
- Kosmetik-Inhaltsstoffe Funktionen
- 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 Datenbank
- 73 · 73-24-5(CAS DataBase Reference)
- NIST chemische Informationen
- Adenine(73-24-5)
- EPA chemische Informationen
- Adenine (73-24-5)
Sicherheit und Regulatorisches
GHS-Klassifizierung
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.
Gefahrenhinweise
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
Toxikologische Informationen
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
Sicherheitsdaten
- F
- 8-10-23
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- UN 2811 6.1/PG 3
- hs_code
- 29335990
- RTECS-Nr.
- AU6125000
- risk_code
- 22-20/21/22
- Toxizität
- LD50 orally in rats: 745 mg/kg (Philips)
- hazard_code
- Xn,Xi
- safety_code
- 26-36
- hazard_class
- 6.1
- packing_group
- III
- Speicherklasse
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- Acute Tox. 3 Oral
Chemie und Industrie
Pharmakologische Informationen
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.
Verwendung und Herstellung
Anwendungen
Beschreibungadenine 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.
VerwendenAdenine 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.
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Ergänzende Hinweise
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.
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