Record Information
Version1.0
Creation Date2016-09-30 22:18:45 UTC
Update Date2020-05-21 16:28:53 UTC
BMDB IDBMDB0000034
Secondary Accession Numbers
  • BMDB00034
Metabolite Identification
Common NameAdenine
DescriptionAdenine 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
Thumb
Synonyms
ValueSource
6-AminopurineChEBI
AChEBI
AdeChEBI
AdeninChEBI
LeuconKegg
1,6-Dihydro-6-iminopurineHMDB
1H-Purin-6-amineHMDB
1H-Purine-6-amineHMDB
3,6-Dihydro-6-iminopurineHMDB
6-Amino-1H-purineHMDB
6-Amino-3H-purineHMDB
6-Amino-7H-purineHMDB
6-Amino-9H-purineHMDB
6-Amino-purineHMDB
9H-Purin-6-amineHMDB
9H-Purin-6-yl-aminHMDB
9H-Purin-6-ylamineHMDB
9H-Purine-6-amineHMDB
AdeninimineHMDB
Vitamin b4HMDB
Vitamin b 4HMDB
4, Vitamin bHMDB
b 4, VitaminHMDB
Chemical FormulaC5H5N5
Average Molecular Weight135.1267
Monoisotopic Molecular Weight135.054495185
IUPAC Name7H-purin-6-amine
Traditional Namevitamin B4
CAS Registry Number73-24-5
SMILES
NC1=C2NC=NC2=NC=N1
InChI Identifier
InChI=1S/C5H5N5/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H3,6,7,8,9,10)
InChI KeyGFFGJBXGBJISGV-UHFFFAOYSA-N
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct Parent6-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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Lysosome
  • Nucleus
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point360 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.03 mg/mLNot Available
LogP-0.09HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP-0.38ALOGPS
logP-0.57ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)10.29ChemAxon
pKa (Strongest Basic)3.64ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.48 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity38.22 m³·mol⁻¹ChemAxon
Polarizability12.29 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-03di-3490000000-7efe9518c90307a43707View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-03di-2690000000-6dc072eb8483a2c38e18View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00di-9350000000-220125189c286547e86cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-03di-4690000000-2d327a6944df53411886View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0006-3920000000-f488e8aa64272a07b3d9View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-000i-0329000000-0b012fa483ce8764d2afView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-03di-3490000000-7efe9518c90307a43707View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-03di-2690000000-6dc072eb8483a2c38e18View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9350000000-220125189c286547e86cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-03di-4690000000-2d327a6944df53411886View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0006-3920000000-f488e8aa64272a07b3d9View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000i-0329000000-0b012fa483ce8764d2afView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-03di-2690000000-534edabc8ab24e32f3f5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a5i-9700000000-e85c2b0bb19cf3401e5aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-0900000000-b24b09629456779d96e6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0900000000-80808f34c7497219d349View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-0a5c-6900000000-f6c0abd6d3fca61bd7f7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0900000000-b24b09629456779d96e6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-80808f34c7497219d349View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a5c-6900000000-f6c0abd6d3fca61bd7f7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-001i-0900000000-cbe0a995dab473351f43View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-001i-0900000000-bfc42d662f222a7c16c7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a59-4900000000-099ee82fc2f658e1cd04View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-c100f5ac716c497996beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-001i-0900000000-379c5c6ea7b1135677c6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-014i-9000000000-346f2325bf2e66e7a339View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-001i-0900000000-87f60041335919c4a0deView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-014l-9000000000-a71034da1c65738b37bdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0a5c-6900000000-f6c0abd6d3fca61bd7f7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-090d369100e8edeb5145View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-001i-0900000000-a56b3bd296195086b5d0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-a76f7f2350e82c676371View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-053r-0900000000-4213d2fff3cdad674b8eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a59-0900000000-d0f2f3ccc46d430b6c3cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0900000000-bf20f302482d1cc4a27dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a59-3900000000-f4155217d6bcdbbcc17fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-066u-9400000000-ada6d909e20e2184a05bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0900000000-95d4894082ada0b24773View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-5900000000-66b1c086d7a666b2d02bView in MoNA
MSMass Spectrum (Electron Ionization)splash10-000i-6900000000-39944576233751576a91View in MoNA
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 50.18 MHz, DMSO-d6, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Lysosome
  • Nucleus
Biospecimen Locations
  • All Tissues
  • Liver
  • Milk
  • Muscle
  • Placenta
  • Prostate Tissue
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
MuscleDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • S. F. Graham, T. ...
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000034
DrugBank IDDB00173
Phenol Explorer Compound IDNot Available
FooDB IDFDB012266
KNApSAcK IDC00001490
Chemspider ID185
KEGG Compound IDC00147
BioCyc IDADENINE
BiGG ID34039
Wikipedia LinkAdenine
METLIN ID85
PubChem Compound190
PDB IDNot Available
ChEBI ID16708
References
Synthesis ReferenceBaddiley, 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)Not Available
General References
  1. Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22. [PubMed:23182357 ]
  2. Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30. [PubMed:25087032 ]

Enzymes

General function:
Nucleotide transport and metabolism
Specific function:
Catalyzes a salvage reaction resulting in the formation of AMP, that is energically less costly than de novo synthesis.
Gene Name:
APRT
Uniprot ID:
Q56JW4
Molecular weight:
19537.0
Reactions
Adenosine monophosphate + Pyrophosphate → Adenine + Phosphoribosyl pyrophosphatedetails
General function:
Amino acid transport and metabolism
Specific function:
Not Available
Gene Name:
DDO
Uniprot ID:
P31228
Molecular weight:
37660.0
General function:
Nucleotide transport and metabolism
Specific function:
The purine nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the beta-(deoxy)ribonucleoside molecules, with the formation of the corresponding free purine bases and pentose-1-phosphate.
Gene Name:
PNP
Uniprot ID:
P55859
Molecular weight:
32037.0
Reactions
Adenosine + Hydrogen phosphate → Adenine + Ribose 1-phosphatedetails
Deoxyadenosine + Hydrogen phosphate → Adenine + Deoxyribose 1-phosphatedetails
General function:
Involved in purinergic nucleotide receptor activity, G-
Specific function:
Receptor for extracellular adenine nucleotides such as ADP (PubMed:7626079). In platelets, binding to ADP leads to mobilization of intracellular calcium ions via activation of phospholipase C, a change in platelet shape, and ultimately platelet aggregation (By similarity).
Gene Name:
P2RY1
Uniprot ID:
P48042
Molecular weight:
42288.0
General function:
Involved in binding
Specific function:
Not Available
Gene Name:
SLC25A4
Uniprot ID:
Q3ZC05
Molecular weight:
32898.0