Showing Compound Card for Adenine (CDB004787)

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Record Information
Version1.0
Created at2020-04-17 18:36:44 UTC
Updated at2020-12-07 19:10:56 UTC
CannabisDB IDCDB004787
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameAdenine
DescriptionAdenine, 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 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. Adenine is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. Adenine is a strong basic compound (based on its pKa). Adenosine triphosphate is used in cellular metabolism as one of the basic methods of transferring chemical energy between reactions. Adenine exists in all living species, ranging from bacteria to humans. In individuals suspected of suffering from a supraventricular tachycardia (SVT), adenosine is used to help identify the rhythm. In humans, adenine is involved in riboflavin metabolism. Adenine is a potentially toxic compound. 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 . 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. Adenine is one of four nitrogenous bases utilized in the synthesis of nucleic acids. Certain SVTs can be successfully terminated with adenosine. Adenosine (adenine with a ribose group) causes transient heart block in the AV node of the heart. These adenine derivatives perform important functions in cellular metabolism. 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. Adenine is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
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 Weight135.13
Monoisotopic Molecular Weight135.0545
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Industrial application:

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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-000i-6900000000-39944576233751576a912014-09-20View Spectrum
GC-MSAdenine, 2 TMS, GC-MS Spectrumsplash10-03di-3490000000-7efe9518c90307a43707Spectrum
GC-MSAdenine, non-derivatized, GC-MS Spectrumsplash10-03di-2690000000-6dc072eb8483a2c38e18Spectrum
GC-MSAdenine, 2 TMS, GC-MS Spectrumsplash10-00di-9350000000-220125189c286547e86cSpectrum
GC-MSAdenine, 2 TMS, GC-MS Spectrumsplash10-03di-4690000000-2d327a6944df53411886Spectrum
GC-MSAdenine, 1 TMS, GC-MS Spectrumsplash10-0006-3920000000-f488e8aa64272a07b3d9Spectrum
GC-MSAdenine, 3 TMS, GC-MS Spectrumsplash10-000i-0329000000-0b012fa483ce8764d2afSpectrum
GC-MSAdenine, non-derivatized, GC-MS Spectrumsplash10-03di-3490000000-7efe9518c90307a43707Spectrum
GC-MSAdenine, non-derivatized, GC-MS Spectrumsplash10-03di-2690000000-6dc072eb8483a2c38e18Spectrum
GC-MSAdenine, non-derivatized, GC-MS Spectrumsplash10-00di-9350000000-220125189c286547e86cSpectrum
GC-MSAdenine, non-derivatized, GC-MS Spectrumsplash10-03di-4690000000-2d327a6944df53411886Spectrum
GC-MSAdenine, non-derivatized, GC-MS Spectrumsplash10-0006-3920000000-f488e8aa64272a07b3d9Spectrum
GC-MSAdenine, non-derivatized, GC-MS Spectrumsplash10-000i-0329000000-0b012fa483ce8764d2afSpectrum
GC-MSAdenine, non-derivatized, GC-MS Spectrumsplash10-03di-2690000000-534edabc8ab24e32f3f5Spectrum
Predicted GC-MSAdenine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a5i-9700000000-e85c2b0bb19cf3401e5aSpectrum
Predicted GC-MSAdenine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-0900000000-b24b09629456779d96e62012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0900000000-80808f34c7497219d3492012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-0a5c-6900000000-f6c0abd6d3fca61bd7f72012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0900000000-b24b09629456779d96e62017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-80808f34c7497219d3492017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a5c-6900000000-f6c0abd6d3fca61bd7f72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-001i-0900000000-cbe0a995dab473351f432017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-001i-0900000000-bfc42d662f222a7c16c72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a59-4900000000-099ee82fc2f658e1cd042021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-c100f5ac716c497996be2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-001i-0900000000-379c5c6ea7b1135677c62021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-014i-9000000000-346f2325bf2e66e7a3392021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-001i-0900000000-87f60041335919c4a0de2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-014l-9000000000-a71034da1c65738b37bd2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0a5c-6900000000-f6c0abd6d3fca61bd7f72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-090d369100e8edeb51452021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-001i-0900000000-a56b3bd296195086b5d02021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-a76f7f2350e82c6763712021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-053r-0900000000-4213d2fff3cdad674b8e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a59-0900000000-d0f2f3ccc46d430b6c3c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0900000000-bf20f302482d1cc4a27d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a59-3900000000-f4155217d6bcdbbcc17f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-066u-9400000000-ada6d909e20e2184a05b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0900000000-95d4894082ada0b247732012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-5900000000-66b1c086d7a666b2d02b2012-07-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 50.18 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)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)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Xanthine dehydrogenase/oxidaseXDH2p23.1P47989 details
S-methyl-5'-thioadenosine phosphorylaseMTAP9p21Q13126 details
Adenine phosphoribosyltransferaseAPRT16q24P07741 details
Hypoxanthine-guanine phosphoribosyltransferaseHPRT1Xq26.1P00492 details
Peroxisomal trans-2-enoyl-CoA reductasePECR2q35Q9BY49 details
Equilibrative nucleoside transporter 2SLC29A211q13Q14542 details
Equilibrative nucleoside transporter 3SLC29A310q22.1Q9BZD2 details
Purine nucleoside phosphorylasePNP14q13.1P00491 details
Transporters
Protein NameGene NameLocusUniprot IDDetails
Equilibrative nucleoside transporter 2SLC29A211q13Q14542 details
Equilibrative nucleoside transporter 3SLC29A310q22.1Q9BZD2 details
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Xanthine dehydrogenase/oxidaseXDH2p23.1P47989 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
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
General ReferencesNot Available

Only showing the first 10 proteins. There are 11 proteins in total.

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Enzymes

Enzyme Details
1. Xanthine dehydrogenase/oxidase
General function:
Involved in oxidoreductase activity
Specific function:
Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
Gene Name:
XDH
Uniprot ID:
P47989
Molecular weight:
146422.99
Enzyme Details
2. S-methyl-5'-thioadenosine phosphorylase
General function:
Involved in transferase activity, transferring pentosyl groups
Specific function:
Catalyzes the reversible phosphorylation of S-methyl-5'-thioadenosine (MTA) to adenine and 5-methylthioribose-1-phosphate. Involved in the breakdown of MTA, a major by-product of polyamine biosynthesis. Responsible for the first step in the methionine salvage pathway after MTA has been generated from S-adenosylmethionine. Has broad substrate specificity with 6-aminopurine nucleosides as preferred substrates.
Gene Name:
MTAP
Uniprot ID:
Q13126
Molecular weight:
31235.76
Enzyme Details
3. Adenine phosphoribosyltransferase
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:
APRT
Uniprot ID:
P07741
Molecular weight:
19607.535
Enzyme Details
4. Hypoxanthine-guanine phosphoribosyltransferase
General function:
Involved in hypoxanthine phosphoribosyltransferase activity
Specific function:
Converts guanine to guanosine monophosphate, and hypoxanthine to inosine monophosphate. Transfers the 5-phosphoribosyl group from 5-phosphoribosylpyrophosphate onto the purine. Plays a central role in the generation of purine nucleotides through the purine salvage pathway.
Gene Name:
HPRT1
Uniprot ID:
P00492
Molecular weight:
24579.155
Enzyme Details
5. Peroxisomal trans-2-enoyl-CoA reductase
General function:
Involved in regulation of apoptosis
Specific function:
Participates in chain elongation of fatty acids. Has no 2,4-dienoyl-CoA reductase activity.
Gene Name:
PECR
Uniprot ID:
Q9BY49
Molecular weight:
32544.11
Enzyme Details
6. Equilibrative nucleoside transporter 2
General function:
Involved in nucleoside transmembrane transporter activity
Specific function:
Mediates equilibrative transport of purine, pyrimidine nucleosides and the purine base hypoxanthine. Less sensitive than SLC29A1 to inhibition by nitrobenzylthioinosine (NBMPR), dipyridamole, dilazep and draflazine
Gene Name:
SLC29A2
Uniprot ID:
Q14542
Molecular weight:
50112.3
Enzyme Details
7. Equilibrative nucleoside transporter 3
General function:
Involved in nucleoside transmembrane transporter activity
Specific function:
Mediates both influx and efflux of nucleosides across the membrane (equilibrative transporter). Mediates transport of adenine, adenosine and uridine, as well as several nucleoside analog drugs, such as anticancer and antiviral agents, including cladribine, cordycepin, tubercidin and AZT. Does not transport hypoxanthine
Gene Name:
SLC29A3
Uniprot ID:
Q9BZD2
Molecular weight:
51799.9
Enzyme Details
8. Purine nucleoside phosphorylase
General function:
Involved in purine-nucleoside phosphorylase activity
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:
P00491
Molecular weight:
32117.69

Transporters

Enzyme Details
1. Equilibrative nucleoside transporter 2
General function:
Involved in nucleoside transmembrane transporter activity
Specific function:
Mediates equilibrative transport of purine, pyrimidine nucleosides and the purine base hypoxanthine. Less sensitive than SLC29A1 to inhibition by nitrobenzylthioinosine (NBMPR), dipyridamole, dilazep and draflazine
Gene Name:
SLC29A2
Uniprot ID:
Q14542
Molecular weight:
50112.3
Enzyme Details
2. Equilibrative nucleoside transporter 3
General function:
Involved in nucleoside transmembrane transporter activity
Specific function:
Mediates both influx and efflux of nucleosides across the membrane (equilibrative transporter). Mediates transport of adenine, adenosine and uridine, as well as several nucleoside analog drugs, such as anticancer and antiviral agents, including cladribine, cordycepin, tubercidin and AZT. Does not transport hypoxanthine
Gene Name:
SLC29A3
Uniprot ID:
Q9BZD2
Molecular weight:
51799.9

Only showing the first 10 proteins. There are 11 proteins in total.

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