Adenin

Adenine

HCID 190CAS 73-24-5

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

adenine73-24-56-Aminopurine1H-Purin-6-amine7H-Purin-6-amineAdeninimineAdeninLeuco-46-Amino-1H-purine6-Amino-7H-purine6-Amino-9H-purine6-Amino-3H-purine
Weitere Namen anzeigen
9H-Purin-6-amineAdeVitamin B4ANEPurin-6-amine
1,6-Dihydro-6-iminopurine3,6-Dihydro-6-iminopurineDTXSID6022557NSC-14666CHEBI:16708JAC85A2161DTXCID502557NSC14666

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

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials Properties15N nuclear magnetic resonance spectrum
LogP-0.09
Solubility · 2 Einträge

1.03 mg/mL

>20.3 [ug/mL] (The mean of the results at pH 7.4)

Melting Point360 °C
Physical DescriptionSolid

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

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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 · 3 Einträge

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%)

Toxikologische Informationen

Toxicity Summary · 1 Eintrag

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).

Sicherheitsdaten

F
8-10-23
wgk
3
tsca
TSCA listed
ridadr
UN 2811 6.1/PG 3
hs_code
29335990
RTECS-Nr.
AU6125000

Chemie und Industrie

Pharmakologische Informationen

Pharmacodynamics · 1 Eintrag

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 · 1 Eintrag

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)

Verwendung und Herstellung

UsesFor nutritional supplementation, also for treating dietary shortage or imbalance
General Manufacturing Information9H-Purin-6-amine: ACTIVE
Anwendungen · 3 Einträge

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.

Anbieter50 Anbieter

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
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INTATRADE GmbH+49 3493/605464 · [email protected]
Ergänzende Hinweise · 1 Eintrag

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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