Adenine (ECMDB00034) (M2MDB000010)
Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 09:55:42 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-09-13 12:56:05 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | Adenine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | 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; 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. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C5H5N5 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 135.1267 Monoisotopic: 135.054495185 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | GFFGJBXGBJISGV-UHFFFAOYSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C5H5N5/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H3,6,7,8,9,10) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 73-24-5 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | 7H-purin-6-amine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | vitamin B4 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | NC1=C2NC=NC2=NC=N1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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 |
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Molecular Framework | Aromatic heteropolycyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
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Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | 360 °C | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | Adenosine + Water > Adenine + Ribose S-Adenosylhomocysteine + Water <> Adenine + S-Ribosyl-L-homocysteine 5'-Methylthioadenosine + Water > 5-Methylthioribose + Adenine 5'-Deoxyadenosine + Water > 5'-Deoxyribose + Adenine Adenine + Phosphoribosyl pyrophosphate <> Adenosine monophosphate + Pyrophosphate Adenosine triphosphate + Dephospho-CoA > 2'-(5-Triphosphoribosyl)-3'-dephospho-CoA + Adenine Adenosine monophosphate + Water <> Adenine + D-Ribose-5-phosphate Adenine + Hydrogen ion + Water > Hypoxanthine + Ammonium Adenosine + Phosphate <> Adenine + Ribose-1-phosphate Deoxyadenosine + Phosphate <> Deoxyribose 1-phosphate + Adenine Adenosine monophosphate + Pyrophosphate <> Adenine + Phosphoribosyl pyrophosphate Adenine + Water <> Hypoxanthine + Ammonia Adenosine + Water <> Adenine + Ribose 5'-Methylthioadenosine + Water <> Adenine + 5-Methylthioribose Adenosine + Phosphate <> Adenine + alpha-D-Ribose 1-phosphate Methylphosphonate + Adenosine triphosphate > α-D-ribose-1-methylphosphonate-5-triphosphate + Adenine Hydrogen ion + Dephospho-CoA + Adenosine triphosphate > 2'-(5-Triphosphoribosyl)-3'-dephospho-CoA + Adenine Water + Adenine > Ammonia + Hypoxanthine Adenosine + Water > D-ribose + Adenine S-Ribosyl-L-homocysteine + Adenine < S-Adenosylhomocysteine + Water Pyrophosphate + Adenosine monophosphate < Phosphoribosyl pyrophosphate + Adenine Water + Adenosine monophosphate > D-Ribose-5-phosphate + Adenine Deoxyadenosine + Phosphate <> Adenine + deoxyribose-1-phosphate N1-Methyladenine + Oxygen + Oxoglutaric acid > Hydrogen ion + Adenine + Carbon dioxide + Formaldehyde + Succinic acid 1-Ethyladenine + Oxygen + Oxoglutaric acid > Adenine + Carbon dioxide + Acetaldehyde + Succinic acid Adenosine monophosphate + Pyrophosphate > Adenine + Phosphoribosyl pyrophosphate More...S-Adenosylhomocysteine + Water > S-Ribosyl-L-homocysteine + Adenine 5'-Methylthioadenosine + Water > S-methyl-5-thio-D-ribose + Adenine S-adenosyl-L-methionine + 7-Aminomethyl-7-deazaguanosine > L-Methionine + Adenine + epoxyqueuosine Adenosine triphosphate + Dephospho-CoA <> 2'-(5-Triphosphoribosyl)-3'-dephospho-CoA + Adenine Adenosine triphosphate + Methylphosphonate <> alpha-D-Ribose 1-methylphosphonate 5-triphosphate + Adenine S-Adenosylhomocysteine + Water > Adenine + S-ribosyl-L-homocysteine + S-ribosyl-L-homocysteine 5'-S-methyl-5'-thioadenosine + Water > 5-Methylthioribose + Adenine 7-aminomethyl-7-deazaguanosine34 in tRNA + S-adenosyl-L-methionine > Hydrogen ion + L-Methionine + Adenine + epoxyqueuosine S-Adenosylhomocysteine + Water > Adenine Adenosine + Water > beta-D-ribofuranose + Adenine Methylphosphonate + Adenosine triphosphate > Adenine + alpha-D-Ribose 1-methylphosphonate 5-triphosphate Adenine + Ribose-1-phosphate > Phosphate + Adenosine Adenosine + Phosphate > Adenine + Ribose-1-phosphate Deoxyadenosine + Phosphate > Adenine + Deoxyribose 1-phosphate Adenine + Phosphoribosyl pyrophosphate > Pyrophosphate + Adenosine monophosphate Adenosine triphosphate + Methylphosphonate <> alpha-D-Ribose 1-methylphosphonate 5-triphosphate + Adenine Adenosine monophosphate + Water <> Adenine + D-Ribose-5-phosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: |
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KEGG Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
EcoCyc Pathways: |
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Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Find out more about how we convert literature concentrations. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Baddiley, J.; Lythgoe, B.; Todd, A. R. Synthesis of purine nucleosides. II. A new and convenient synthesis of adenine. Journal of the Chemical Society (1943), 386-7. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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External Links: |
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Enzymes
- General function:
- Involved in hypoxanthine phosphoribosyltransferase activity
- Specific function:
- This enzyme acts exclusively on hypoxanthine; it does not act on guanine
- Gene Name:
- hpt
- Uniprot ID:
- P0A9M2
- Molecular weight:
- 20115
Reactions
IMP + diphosphate = hypoxanthine + 5-phospho-alpha-D-ribose 1-diphosphate. |
- General function:
- Involved in purine-nucleoside phosphorylase activity
- Specific function:
- Cleavage of guanosine or inosine to respective bases and sugar-1-phosphate molecules
- Gene Name:
- deoD
- Uniprot ID:
- P0ABP8
- Molecular weight:
- 25950
Reactions
Purine nucleoside + phosphate = purine + alpha-D-ribose 1-phosphate. |
- General function:
- Involved in catalytic activity
- Specific function:
- Involved in regulation of AMP concentrations
- Gene Name:
- amn
- Uniprot ID:
- P0AE12
- Molecular weight:
- 53994
Reactions
AMP + H(2)O = D-ribose 5-phosphate + adenine. |
- General function:
- Involved in adenosylhomocysteine nucleosidase activity
- Specific function:
- Catalyzes the irreversible cleavage of the glycosidic bond in both 5'-methylthioadenosine (MTA) and S- adenosylhomocysteine (SAH/AdoHcy) to adenine and the corresponding thioribose, 5'-methylthioribose and S-ribosylhomocysteine, respectively. Can also use 5'-isobutylthioadenosine, 5'-n- butylthioadenosine, S-adenosyl-D-homocysteine, decarboxylated adenosylhomocysteine, deaminated adenosylhomocysteine and S-2-aza- adenosylhomocysteine as substrates
- Gene Name:
- mtnN
- Uniprot ID:
- P0AF12
- Molecular weight:
- 24354
Reactions
S-adenosyl-L-homocysteine + H(2)O = S-(5-deoxy-D-ribos-5-yl)-L-homocysteine + adenine. |
S-methyl-5'-thioadenosine + H(2)O = S-methyl-5-thio-D-ribose + adenine. |
- General function:
- Involved in riboflavin synthase activity
- Specific function:
- Riboflavin synthase is a bifunctional enzyme complex catalyzing the formation of riboflavin from 5-amino-6-(1'-D)- ribityl-amino-2,4(1H,3H)-pyrimidinedione and L-3,4-dihydrohy-2- butanone-4-phosphate via 6,7-dimethyl-8-lumazine. The alpha subunit catalyzes the dismutation of 6,7-dimethyl-8-lumazine to riboflavin and 5-amino-6-(1'-D)-ribityl-amino-2,4(1H,3H)- pyrimidinedione
- Gene Name:
- ribE
- Uniprot ID:
- P0AFU8
- Molecular weight:
- 23445
Reactions
2 6,7-dimethyl-8-(1-D-ribityl)lumazine = riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine. |
- General function:
- Involved in hydrolase activity, hydrolyzing N-glycosyl compounds
- Specific function:
- Hydrolyzes both purine and pyrimidine ribonucleosides with a broad-substrate specificity with decreasing activity in the order uridine, xanthosine, inosine, adenosine, cytidine, guanosine
- Gene Name:
- rihC
- Uniprot ID:
- P22564
- Molecular weight:
- 32560
- General function:
- Involved in adenine deaminase activity
- Specific function:
- Adenine + H(2)O = hypoxanthine + NH(3)
- Gene Name:
- ade
- Uniprot ID:
- P31441
- Molecular weight:
- 63739
Reactions
Adenine + H(2)O = hypoxanthine + NH(3). |
- General function:
- Involved in hydrolase activity, hydrolyzing N-glycosyl compounds
- Specific function:
- Hydrolyzes cytidine or uridine to ribose and cytosine or uracil, respectively. Has a clear preference for cytidine over uridine. Strictly specific for ribonucleosides. Has a low but significant activity for the purine nucleoside xanthosine
- Gene Name:
- rihB
- Uniprot ID:
- P33022
- Molecular weight:
- 33748
Reactions
A pyrimidine nucleoside + H(2)O = D-ribose + a pyrimidine base. |
- General function:
- Involved in adenine phosphoribosyltransferase activity
- Specific function:
- Catalyzes a salvage reaction resulting in the formation of AMP, that is energically less costly than de novo synthesis
- Gene Name:
- apt
- Uniprot ID:
- P69503
- Molecular weight:
- 19859
Reactions
AMP + diphosphate = adenine + 5-phospho-alpha-D-ribose 1-diphosphate. |
- General function:
- Involved in ATP binding
- Specific function:
- Catalyzes the formation of 2-(5''-triphosphoribosyl)-3'- dephosphocoenzyme-A, the precursor of the prosthetic group of the holo-acyl carrier protein (gamma chain) of citrate lyase, from ATP and dephospho-CoA
- Gene Name:
- citG
- Uniprot ID:
- P77231
- Molecular weight:
- 31644
Reactions
ATP + 3-dephospho-CoA = 2'-(5-triphosphoribosyl)-3'-dephospho-CoA + adenine. |
- General function:
- Not Available
- Specific function:
- Dioxygenase that repairs alkylated DNA and RNA containing 3-methylcytosine or 1-methyladenine by oxidative demethylation. Has highest activity towards 3-methylcytosine. Has lower activity towards alkylated DNA containing ethenoadenine, and no detectable activity towards 1-methylguanine or 3-methylthymine. Accepts double-stranded and single-stranded substrates. Requires molecular oxygen, alpha-ketoglutarate and iron. Provides extensive resistance to alkylating agents such as MMS and DMS (SN2 agents), but not to MMNG and MNU (SN1 agents). Dioxygenase that repairs alkylated DNA and RNA containing 3-methylcytosine or 1-methyladenine by oxidative demethylation. Has highest activity towards 3-methylcytosine. Has lower activity towards alkylated DNA containing ethenoadenine, and no detectable activity towards 1-methylguanine or 3-methylthymine. Accepts double-stranded and single-stranded substrates. Requires molecular oxygen, alpha-ketoglutarate and iron. Provides extensive resistance to alkylating agents such as MMS and DMS (SN2 agents), but not to MMNG and MNU (SN1 agents).
- Gene Name:
- alkB
- Uniprot ID:
- P05050
- Molecular weight:
- Not Available
Reactions
DNA-base-CH(3) + 2-oxoglutarate + O(2) = DNA-base + formaldehyde + succinate + CO(2). |
DNA-base-CH(3) + 2-oxoglutarate + O(2) = DNA-base + formaldehyde + succinate + CO(2). |
- General function:
- Translation, ribosomal structure and biogenesis
- Specific function:
- Transfers and isomerizes the ribose moiety from AdoMet to the 7-aminomethyl group of 7-deazaguanine (preQ1-tRNA) to give epoxyqueuosine (oQ-tRNA)
- Gene Name:
- queA
- Uniprot ID:
- P0A7F9
- Molecular weight:
- 39430
Reactions
S-adenosylmethionine + 7-aminomethyl-7-deazaguanosine = methionine + adenine + epoxyqueuosine. |
- General function:
- organic phosphonate catabolic process
- Specific function:
- Together with PhnG, PhnH and PhnI is required for the transfer of the ribose triphosphate moiety from ATP to methyl phosphonate.
- Gene Name:
- phnL
- Uniprot ID:
- P16679
- Molecular weight:
- 24705
Reactions
ATP + methylphosphonate = alpha-D-ribose 1-methylphosphonate 5-triphosphate + adenine |
- General function:
- organic phosphonate catabolic process
- Specific function:
- Together with PhnG, PhnH and PhnL is required for the transfer of the ribose triphosphate moiety from ATP to methyl phosphonate. PhnI alone has nucleosidase activity, catalyzing the hydrolysis of ATP or GTP forming alpha-D-ribose 5-triphosphate and adenine or guanine, respectively.
- Gene Name:
- phnI
- Uniprot ID:
- P16687
- Molecular weight:
- 38852
Reactions
ATP + methylphosphonate = alpha-D-ribose 1-methylphosphonate 5-triphosphate + adenine |
- General function:
- organic phosphonate catabolic process
- Specific function:
- Together with PhnG, PhnI and PhnL is required for the transfer of the ribose triphosphate moiety from ATP to methyl phosphonate.
- Gene Name:
- phnH
- Uniprot ID:
- P16686
- Molecular weight:
- 21027
Reactions
ATP + methylphosphonate = alpha-D-ribose 1-methylphosphonate 5-triphosphate + adenine |
- General function:
- organic phosphonate transport
- Specific function:
- Together with PhnH, PhnI and PhnL is required for the transfer of the ribose triphosphate moiety from ATP to methyl phosphonate.
- Gene Name:
- phnG
- Uniprot ID:
- P16685
- Molecular weight:
- 16539
Reactions
ATP + methylphosphonate = alpha-D-ribose 1-methylphosphonate 5-triphosphate + adenine |
Transporters
- General function:
- Involved in transporter activity
- Specific function:
- Specific, proton motive force-dependent high-affinity transporter for xanthine
- Gene Name:
- xanP
- Uniprot ID:
- P0AGM9
- Molecular weight:
- 48868
- General function:
- Involved in transporter activity
- Specific function:
- High-affinity uptake of adenine
- Gene Name:
- purP
- Uniprot ID:
- P31466
- Molecular weight:
- 46865
- General function:
- Involved in transporter activity
- Specific function:
- Non-specific porin
- Gene Name:
- ompN
- Uniprot ID:
- P77747
- Molecular weight:
- 41220
- General function:
- Involved in transporter activity
- Specific function:
- Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
- Gene Name:
- phoE
- Uniprot ID:
- P02932
- Molecular weight:
- 38922
- General function:
- Involved in transporter activity
- Specific function:
- OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
- Gene Name:
- ompF
- Uniprot ID:
- P02931
- Molecular weight:
- 39333
- General function:
- Involved in transporter activity
- Specific function:
- Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
- Gene Name:
- ompC
- Uniprot ID:
- P06996
- Molecular weight:
- 40368
- General function:
- organic phosphonate transport
- Specific function:
- Together with PhnH, PhnI and PhnL is required for the transfer of the ribose triphosphate moiety from ATP to methyl phosphonate.
- Gene Name:
- phnG
- Uniprot ID:
- P16685
- Molecular weight:
- 16539
Reactions
ATP + methylphosphonate = alpha-D-ribose 1-methylphosphonate 5-triphosphate + adenine |