Adenine (YMDB00887)

Identification

YMDB ID

YMDB00887

Name

Adenine

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Adenine, also known as 6-aminopurine or Ade, 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. Adenine is a strong basic compound (based on its pKa). Adenine exists in all living species, ranging from bacteria to humans. Adenine is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

1,6-Dihydro-6-iminopurine
1H-Purin-6-amine
1H-Purine-6-amine
3,6-Dihydro-6-iminopurine
6-Amino-1H-purine
6-Amino-3H-purine
6-Amino-7H-purine
6-Amino-9H-purine
6-amino-Purine
6-Aminopurine
9H-Purin-6-amine
9H-Purin-6-yl-amin
9H-purin-6-ylamine
9H-Purine-6-amine
Ade
Adenine
Adeninimine
Vitamin B4
A
Adenin
Leucon
Vitamin b 4
4, Vitamin b
b 4, Vitamin

CAS number

73-24-5

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)

IUPAC Name

7H-purin-6-amine

Traditional IUPAC Name

vitamin B4

Chemical Formula

C₅H₅N₅

SMILES

[H]N([H])C1=NC([H])=NC2=C1N([H])C([H])=N2

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

6-aminopurine
Aminopyrimidine
Imidolactam
Pyrimidine
Heteroaromatic compound
Imidazole
Azole
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

6-aminopurines (CHEBI:16708 )
purine nucleobase (CHEBI:16708 )
purines (C00147 )
a ring (ADENINE-RING )

Physical Properties

State

Solid

Charge

Melting point

360 °C

Experimental Properties

Property	Value	Reference
Water Solubility	1.03 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp
LogP	-0.09 [HANSCH,C ET AL. (1995)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	11.5 g/L	ALOGPS
logP	-0.38	ALOGPS
logP	-0.57	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	10.29	ChemAxon
pKa (Strongest Basic)	3.64	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	80.48 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	38.22 m³·mol⁻¹	ChemAxon
Polarizability	12.29 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

extracellular
mitochondrion
cytoplasm

Organoleptic Properties

Flavour/Odour	Source
Odorless	FDB012266

SMPDB Pathways

Methionine metabolism and salvage	PW002384
Pantothenate and CoA biosynthesis	PW002463

KEGG Pathways

Pantothenate and CoA biosynthesis	ec00770
Purine metabolism	ec00230

SMPDB Reactions

phosphate + 5'-S-methyl-5'-thioadenosine → 5-Methylthioribose 1-phosphate + Adenine

Adenosine triphosphate + hydron + Dephospho-CoA → Adenine + 2'-(5-Triphosphoribosyl)-3'-dephospho-CoA

KEGG Reactions

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-03di-3490000000-7efe9518c90307a43707	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-03di-2690000000-6dc072eb8483a2c38e18	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00di-9350000000-220125189c286547e86c	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-03di-4690000000-2d327a6944df53411886	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-0006-3920000000-f488e8aa64272a07b3d9	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-000i-0329000000-0b012fa483ce8764d2af	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-03di-3490000000-7efe9518c90307a43707	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-03di-2690000000-6dc072eb8483a2c38e18	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9350000000-220125189c286547e86c	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-03di-4690000000-2d327a6944df53411886	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0006-3920000000-f488e8aa64272a07b3d9	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-000i-0329000000-0b012fa483ce8764d2af	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-03di-2690000000-534edabc8ab24e32f3f5	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a5i-9700000000-e85c2b0bb19cf3401e5a	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4i-0900000000-b24b09629456779d96e6	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-001i-0900000000-80808f34c7497219d349	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative	splash10-0a5c-6900000000-f6c0abd6d3fca61bd7f7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0a4i-0900000000-b24b09629456779d96e6	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-001i-0900000000-80808f34c7497219d349	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0a5c-6900000000-f6c0abd6d3fca61bd7f7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-001i-0900000000-cbe0a995dab473351f43	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-001i-0900000000-bfc42d662f222a7c16c7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a59-4900000000-099ee82fc2f658e1cd04	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-c100f5ac716c497996be	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-001i-0900000000-379c5c6ea7b1135677c6	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9000000000-346f2325bf2e66e7a339	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-001i-0900000000-87f60041335919c4a0de	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-014l-9000000000-a71034da1c65738b37bd	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0a5c-6900000000-f6c0abd6d3fca61bd7f7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-090d369100e8edeb5145	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-001i-0900000000-a56b3bd296195086b5d0	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-a76f7f2350e82c676371	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-053r-0900000000-4213d2fff3cdad674b8e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a59-0900000000-d0f2f3ccc46d430b6c3c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-0900000000-bf20f302482d1cc4a27d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a59-3900000000-f4155217d6bcdbbcc17f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-066u-9400000000-ada6d909e20e2184a05b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-0900000000-95d4894082ada0b24773	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-014i-5900000000-66b1c086d7a666b2d02b	JSpectraViewer \| MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-000i-6900000000-39944576233751576a91	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
ROUSH, A. H., SAEED, M. (1960). "Adenine metabolism in Saccharomyces cerevisiae adenase from bakers' yeast." Biochem Biophys Res Commun 2:43-47.14439573
Aranda, A., Jimenez-Marti, E., Orozco, H., Matallana, E., Del Olmo, M. (2006). "Sulfur and adenine metabolisms are linked, and both modulate sulfite resistance in wine yeast." J Agric Food Chem 54:5839-5846.16881685
Subhi, A. L., Diegelman, P., Porter, C. W., Tang, B., Lu, Z. J., Markham, G. D., Kruger, W. D. (2003). "Methylthioadenosine phosphorylase regulates ornithine decarboxylase by production of downstream metabolites." J Biol Chem 278:49868-49873.14506228
Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666

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.

External Links:

Resource	Link
CHEBI ID	16708
HMDB ID	HMDB00034
Pubchem Compound ID	190
Kegg ID	C00147
ChemSpider ID	185
FOODB ID	FDB012266
Wikipedia	Adenine
BioCyc ID	ADENINE

Enzymes

Protein Details

1. Purine nucleoside phosphorylase

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:: PNP1
Uniprot ID:: Q05788
Molecular weight:: 33754.60156

Reactions

Purine nucleoside + phosphate → purine + alpha-D-ribose 1-phosphate.

Protein Details

2. Vitamin B6 transporter TPN1

General function:: Involved in nucleobase transmembrane transporter activity
Specific function:: Thiamine-regulated, high affinity import carrier of pyridoxine, pyridoxal and pyridoxamine
Gene Name:: TPN1
Uniprot ID:: P53099
Molecular weight:: 64545.80078

Protein Details

3. Adenosine deaminase

General function:: Involved in deaminase activity
Specific function:: Adenosine + H(2)O = inosine + NH(3)
Gene Name:: AAH1
Uniprot ID:: P53909
Molecular weight:: 39634.69922

Reactions

Adenosine + H(2)O → inosine + NH(3).

Protein Details

4. Adenine phosphoribosyltransferase 1

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:: APT1
Uniprot ID:: P49435
Molecular weight:: 20586.59961

Reactions

AMP + diphosphate → adenine + 5-phospho-alpha-D-ribose 1-diphosphate.

Protein Details

5. Adenine phosphoribosyltransferase 2

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. May lack catalytic activity
Gene Name:: APT2
Uniprot ID:: P36973
Molecular weight:: 19999.80078

Reactions

AMP + diphosphate → adenine + 5-phospho-alpha-D-ribose 1-diphosphate.

Protein Details

6. Multicopy enhancer of UAS2

General function:: Involved in catalytic activity
Specific function:: Seems to be implicated in the regulation of the expression of the ADH2 gene
Gene Name:: MEU1
Uniprot ID:: Q07938
Molecular weight:: 37856.30078

Reactions

S-methyl-5'-thioadenosine + phosphate → adenine + S-methyl-5-thio-alpha-D-ribose 1-phosphate

Protein Details

7. Uridine nucleosidase

General function:: Involved in hydrolase activity, hydrolyzing N-glycosyl compounds
Specific function:: Also acts on cytidine
Gene Name:: URH1
Uniprot ID:: Q04179
Molecular weight:: 37960.0

Reactions

Uridine + H(2)O → D-ribose + uracil.

Transporters

Protein Details

1. Purine-cytosine permease FCY21

General function:: Involved in nucleobase transmembrane transporter activity
Specific function:: Probable purine-cytosine permease
Gene Name:: FCY21
Uniprot ID:: P40039
Molecular weight:: 58049.60156

Protein Details

2. Purine-cytosine permease FCY2

General function:: Involved in nucleobase transmembrane transporter activity
Specific function:: This permease has a broad specificity towards purines, and also transport cytosine and 5-methylcytosine but neither uracil nor thymine
Gene Name:: FCY2
Uniprot ID:: P17064
Molecular weight:: 58200.69922

Protein Details

3. Purine-cytosine permease FCY22

General function:: Involved in nucleobase transmembrane transporter activity
Specific function:: Probable purine-cytosine permease
Gene Name:: FCY22
Uniprot ID:: Q12119
Molecular weight:: 57326.69922

Structure for #<Compound:0xb3b8dd4c>

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Transporters