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Record Information
Version1.0
Creation Date2016-09-30 22:18:45 UTC
Update Date2020-05-21 16:28:53 UTC
MCDB ID BMDB0000034
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
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-03di-3490000000-7efe9518c90307a437072014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-03di-2690000000-6dc072eb8483a2c38e182014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00di-9350000000-220125189c286547e86c2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-03di-4690000000-2d327a6944df534118862014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0006-3920000000-f488e8aa64272a07b3d92014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-000i-0329000000-0b012fa483ce8764d2af2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-03di-3490000000-7efe9518c90307a437072017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-03di-2690000000-6dc072eb8483a2c38e182017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9350000000-220125189c286547e86c2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-03di-4690000000-2d327a6944df534118862017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0006-3920000000-f488e8aa64272a07b3d92017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000i-0329000000-0b012fa483ce8764d2af2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-03di-2690000000-534edabc8ab24e32f3f52017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a5i-9700000000-e85c2b0bb19cf3401e5a2016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-0900000000-b24b09629456779d96e62012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0900000000-80808f34c7497219d3492012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-0a5c-6900000000-f6c0abd6d3fca61bd7f72012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0900000000-b24b09629456779d96e62017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-80808f34c7497219d3492017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a5c-6900000000-f6c0abd6d3fca61bd7f72017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-001i-0900000000-cbe0a995dab473351f432017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-001i-0900000000-bfc42d662f222a7c16c72017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a59-4900000000-099ee82fc2f658e1cd042021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-c100f5ac716c497996be2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-001i-0900000000-379c5c6ea7b1135677c62021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-014i-9000000000-346f2325bf2e66e7a3392021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-001i-0900000000-87f60041335919c4a0de2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-014l-9000000000-a71034da1c65738b37bd2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0a5c-6900000000-f6c0abd6d3fca61bd7f72021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-090d369100e8edeb51452021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-001i-0900000000-a56b3bd296195086b5d02021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-a76f7f2350e82c6763712021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-053r-0900000000-4213d2fff3cdad674b8e2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a59-0900000000-d0f2f3ccc46d430b6c3c2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0900000000-bf20f302482d1cc4a27d2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a59-3900000000-f4155217d6bcdbbcc17f2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-066u-9400000000-ada6d909e20e2184a05b2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0900000000-95d4894082ada0b247732012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-5900000000-66b1c086d7a666b2d02b2012-07-24View Spectrum
MSMass Spectrum (Electron Ionization)splash10-000i-6900000000-39944576233751576a912014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50.18 MHz, DMSO-d6, experimental)Not Available2014-09-23View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
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 Available2012-12-04View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
Detected but not QuantifiedNot Applicable details
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0000034
DrugBank IDDB00173
Phenol Explorer Compound IDNot Available
FoodDB 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)Download (PDF)
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 ]