Identification

Name
Adenine
Accession Number
DB00173  (NUTR00012, EXPT00520)
Type
Small Molecule
Groups
Approved, Nutraceutical
Description

A purine base and a fundamental unit of adenine nucleotides.

Structure
Thumb
Synonyms
  • 6-Aminopurine
  • Adenin
  • Vitamin B4
Product Ingredients
IngredientUNIICASInChI Key
Adenine hydrochloride364H11M7OD2922-28-3UQVDQSWZQXDUJB-UHFFFAOYSA-N
Adenine sulfate741GJF3K9M321-30-2LQXHSCOPYJCOMD-UHFFFAOYSA-N
International/Other Brands
Leuco-4
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Additive Solution Formula 3 As-3Adenine (0.030 g) + Citric acid monohydrate (0.042 g) + Glucose (1.10 g) + Sodium Chloride (0.410 g) + Trisodium citrate dihydrate (0.588 g) + Sodium phosphate, monobasic, monohydrate (0.276 g)SolutionUnknownTerumo Bct, Inc.2013-05-31Not applicableCanada
Additive Solution Sodium Adenine Glucose Mannitol (sagm)Adenine (0.169 g) + Glucose (9 g) + Mannitol (5.25 g) + Sodium Chloride (8.77 g)SolutionUnknownMaco Pharma2016-08-22Not applicableCanada
Anticoagulant Cit Phos Dex Adenine Sol USPAdenine (17.3 mg) + Citric Acid (189 mg) + Glucose (2 g) + Sodium Citrate (1.66 g) + Sodium phosphate (140 mg)SolutionIntravenousBaxter Laboratories1996-10-17Not applicableCanada
As 3Adenine (.03 g/100mL) + Citric acid monohydrate (.042 g/100mL) + Glucose (1.1 g/100mL) + Sodium Chloride (.41 g/100mL) + Sodium Citrate (.588 g/100mL) + Sodium phosphate, monobasic, monohydrate (.276 g/100mL)Injection, solutionIntravenousTerumo Bct2002-05-29Not applicableUs
Cpd Adenine Cpda 1Adenine (28 mg) + Citric Acid (330 mg) + Glucose (3.17 g) + Sodium Citrate (2.63 g) + Sodium phosphate (220 mg)LiquidIntravenousFenwal Labs, Division of Baxter Corporation1981-12-311997-08-11Canada
Cpda-1Adenine (17.3 mg/63mL) + Citric acid monohydrate (206 mg/63mL) + Dextrose monohydrate (2.01 g/63mL) + Trisodium citrate dihydrate (1.66 g/63mL) + Sodium phosphate, monobasic, monohydrate (140 mg/63mL)SolutionIntravenousFenwal, Inc.2010-08-19Not applicableUs
Cpda-1Adenine (19.3 mg/70mL) + Citric Acid (209 mg/70mL) + Dextrose monohydrate (2.23 g/70mL) + Trisodium citrate dihydrate (1.84 g/70mL) + Sodium phosphate, monobasic, monohydrate (155 mg/70mL)SolutionIntravenousFenwal, Inc.2007-03-01Not applicableUs
Cpda-1Adenine (17.3 mg/63mL) + Citric Acid (188 mg/63mL) + Dextrose monohydrate (2 g/63mL) + Trisodium citrate dihydrate (1.66 g/63mL) + Sodium phosphate, monobasic, monohydrate (140 mg/63mL)SolutionIntravenousFenwal, Inc.2007-03-01Not applicableUs
Cpda-1Adenine (13.5 mg/49mL) + Citric Acid (147 mg/49mL) + Dextrose monohydrate (1.56 g/49mL) + Trisodium citrate dihydrate (1.29 g/49mL) + Sodium phosphate, monobasic, monohydrate (109 mg/49mL)SolutionIntravenousFenwal, Inc.2010-05-25Not applicableUs
Cpda-1Adenine (19.3 mg/70mL) + Citric Acid (209 mg/70mL) + Dextrose monohydrate (2.23 g/70mL) + Trisodium citrate dihydrate (1.84 g/70mL) + Sodium phosphate, monobasic, monohydrate (155 mg/70mL)SolutionIntravenousFenwal, Inc.2008-12-15Not applicableUs
Categories
UNII
JAC85A2161
CAS number
73-24-5
Weight
Average: 135.1267
Monoisotopic: 135.054495185
Chemical Formula
C5H5N5
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
SMILES
NC1=C2NC=NC2=NC=N1

Pharmacology

Indication

For nutritional supplementation, also for treating dietary shortage or imbalance

Structured Indications
Not Available
Pharmacodynamics

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 . These adenine derivatives perform important functions in cellular metabolism. Adenine is one of four nitrogenous bases utilized in the synthesis of nucleic acids. 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. Adenosine (adenine with a ribose group) causes transient heart block in the AV node of the heart. In individuals suspected of suffering from a supraventricular tachycardia (SVT), adenosine is used to help identify the rhythm. Certain SVTs can be successfully terminated with adenosine.

Mechanism of action

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. Adenosine triphosphate is used in cellular metabolism as one of the basic methods of transferring chemical energy between reactions. In older literature, adenine was sometimes called Vitamin B4Not Available

TargetActionsOrganism
UAdenine phosphoribosyltransferaseNot AvailableHuman
UDNANot AvailableHuman
US-methyl-5'-thioadenosine phosphorylaseNot AvailableHuman
UNicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferaseNot AvailableSalmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
UAcetyl-CoA carboxylase 2Not AvailableHuman
ULow molecular weight phosphotyrosine protein phosphataseNot AvailableHuman
U5'-methylthioadenosine/S-adenosylhomocysteine nucleosidaseNot AvailableEscherichia coli (strain K12)
UPeroxisomal trans-2-enoyl-CoA reductaseNot AvailableHuman
UA/G-specific adenine glycosylaseNot AvailableEscherichia coli (strain K12)
UNucleoside deoxyribosyltransferase-INot AvailableLactobacillus helveticus
USRSF protein kinase 2Not AvailableHuman
UHolliday junction ATP-dependent DNA helicase RuvBNot AvailableThermus thermophilus (strain HB8 / ATCC 27634 / DSM 579)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Lesch-Nyhan Syndrome (LNS)Disease
Myoadenylate deaminase deficiencyDisease
Gout or Kelley-Seegmiller SyndromeDisease
Azathioprine Action PathwayDrug action
Xanthinuria type IIDisease
Purine MetabolismMetabolic
Adenosine Deaminase DeficiencyDisease
Xanthine Dehydrogenase Deficiency (Xanthinuria)Disease
AICA-RibosiduriaDisease
Mercaptopurine Action PathwayDrug action
Thioguanine Action PathwayDrug action
Xanthinuria type IDisease
Adenylosuccinate Lyase DeficiencyDisease
Molybdenum Cofactor DeficiencyDisease
Purine Nucleoside Phosphorylase DeficiencyDisease
Adenine phosphoribosyltransferase deficiency (APRT)Disease
Mitochondrial DNA depletion syndromeDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
IrinotecanThe serum concentration of SN-38 an active metabolite of Irinotecan can be increased when used in combination with Adenine.Approved, Investigational
Food Interactions
Not Available

References

Synthesis Reference

Eiichi Yonemitsu, Tomiya Isshiki, Yasuhiko Kijima, "Process for preparing adenine." U.S. Patent US4059582, issued March, 1964.

US4059582
General References
Not Available
External Links
Human Metabolome Database
HMDB00034
KEGG Drug
D00034
KEGG Compound
C00147
PubChem Compound
190
PubChem Substance
46507319
ChemSpider
185
BindingDB
181146
ChEBI
16708
ChEMBL
CHEMBL226345
Therapeutic Targets Database
DAP000982
PharmGKB
PA448048
HET
ADE
Wikipedia
Adenine
PDB Entries
1aha / 1bjq / 1cb0 / 1d2a / 1giu / 1hqc / 1ifs / 1j1r / 1jh8 / 1jys
show 112 more
MSDS
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Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Not Yet RecruitingTreatmentOsteoarthritis of the Hands1
1CompletedOtherAsthma Bronchial1
1CompletedTreatmentDyslipidemias1
1CompletedTreatmentFabry's Disease1
1CompletedTreatmentGastroparesis1
1CompletedTreatmentHealthy Volunteers1
1CompletedTreatmentMalaria caused by plasmodium vivax1
1CompletedTreatmentRelapsing Remitting Multiple Sclerosis (RRMS)1
1Unknown StatusNot AvailableHealthy Volunteers1
1, 2CompletedPreventionOvarian Hyperstimulation Syndrome1
2Active Not RecruitingTreatmentCancer, Breast1
2Active Not RecruitingTreatmentHodgkins Disease (HD)1
2CompletedTreatmentCancer, Breast1
2CompletedTreatmentEpilepsies1
2CompletedTreatmentOpioid Abuse1
2Unknown StatusPreventionParalytic Ileus1
3Active Not RecruitingTreatmentCancer, Breast1
3CompletedPreventionHip Replacement, Total1
3CompletedTreatmentCancer, Breast1
3CompletedTreatmentMultiple Myeloma (MM)1
3CompletedTreatmentPain1
3RecruitingTreatmentNeoplasms, Breast1
4Active Not RecruitingTreatmentPlasmodium Infections1
4CompletedTreatmentBlock Level / Gastrointestinal Surgery / Target Controlled Infusion (TCI) / Thoracic Epidural Anesthesia1
4Not Yet RecruitingNot AvailableSickle Cell Disorders1
4Not Yet RecruitingBasic ScienceHeart Defects,Congenital1
4TerminatedPreventionPerineal Wound Infection1
4Unknown StatusTreatmentDisorder of Vitamin D / Kidney Failure,Chronic1
4Unknown StatusTreatmentIrritable Bowel Syndrome (IBS)1
Not AvailableCompletedNot AvailablePulmonary Disease, Chronic Obstructive1
Not AvailableCompletedSupportive CareAnaesthesia therapy / Body Temperature Changes1
Not AvailableCompletedTreatmentBronchiectasis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Injection, solutionIntravenous
LiquidIntravenous
SolutionExtracorporeal
SolutionIntravenous
SolutionUnknown
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)360 dec °CPhysProp
water solubility1030 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-0.09HANSCH,C ET AL. (1995)
logS-2.12ADME Research, USCD
pKa4.15 (at 25 °C)KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
Water Solubility11.5 mg/mLALOGPS
logP-0.38ALOGPS
logP-0.57ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)10.29ChemAxon
pKa (Strongest Basic)5.32ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.48 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity38.22 m3·mol-1ChemAxon
Polarizability12.29 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9733
Blood Brain Barrier+0.9395
Caco-2 permeable-0.5225
P-glycoprotein substrateNon-substrate0.6835
P-glycoprotein inhibitor INon-inhibitor0.98
P-glycoprotein inhibitor IINon-inhibitor0.9805
Renal organic cation transporterNon-inhibitor0.8573
CYP450 2C9 substrateNon-substrate0.9144
CYP450 2D6 substrateNon-substrate0.8966
CYP450 3A4 substrateNon-substrate0.7957
CYP450 1A2 substrateNon-inhibitor0.6459
CYP450 2C9 inhibitorNon-inhibitor0.9567
CYP450 2D6 inhibitorNon-inhibitor0.988
CYP450 2C19 inhibitorNon-inhibitor0.9441
CYP450 3A4 inhibitorNon-inhibitor0.9246
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9024
Ames testAMES toxic0.6746
CarcinogenicityNon-carcinogens0.9197
BiodegradationNot ready biodegradable0.9857
Rat acute toxicity2.4381 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9646
hERG inhibition (predictor II)Non-inhibitor0.906
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
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Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-03di-3490000000-7efe9518c90307a43707
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-03di-2690000000-6dc072eb8483a2c38e18
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-00di-9350000000-220125189c286547e86c
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-03di-4690000000-2d327a6944df53411886
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-0006-3920000000-f488e8aa64272a07b3d9
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-000i-0329000000-0b012fa483ce8764d2af
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-03di-3490000000-7efe9518c90307a43707
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-03di-2690000000-6dc072eb8483a2c38e18
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-9350000000-220125189c286547e86c
GC-MS Spectrum - GC-MSGC-MSsplash10-03di-4690000000-2d327a6944df53411886
GC-MS Spectrum - GC-MSGC-MSsplash10-0006-3920000000-f488e8aa64272a07b3d9
GC-MS Spectrum - GC-MSGC-MSsplash10-000i-0329000000-0b012fa483ce8764d2af
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-03di-2690000000-534edabc8ab24e32f3f5
Mass Spectrum (Electron Ionization)MSsplash10-000i-6900000000-39944576233751576a91
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-000i-0900000000-95d4894082ada0b24773
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-014i-5900000000-66b1c086d7a666b2d02b
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-014i-9200000000-4202a1aec437f3fd1275
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-0900000000-c1766360e5f779d277ab
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-0900000000-68585e8dac03a15d5210
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-014i-0900000000-3db475b164c0f884b93d
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-014i-2900000000-7e2deed118def434e8db
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0a4i-0900000000-b24b09629456779d96e6
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-000i-0900000000-b2cc6b5ce2fe2affe47d
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, PositiveLC-MS/MSsplash10-000i-0900000000-f45a65a00be3c0c36350
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-001i-0900000000-80808f34c7497219d349
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, NegativeLC-MS/MSsplash10-0a5c-6900000000-f6c0abd6d3fca61bd7f7
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0900000000-f2335984e7dd7e129a8c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0900000000-ee084d257bf2325fb370
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-067i-9700000000-5a42850e3f5331952458
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0900000000-05fa9674ab4d9e5e174e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0900000000-dc404aa4196bbf0ae9cd
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-05o0-8900000000-b56d110371cd80ac76e0
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0900000000-b24b09629456779d96e6
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-001i-0900000000-80808f34c7497219d349
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0a5c-6900000000-f6c0abd6d3fca61bd7f7
MS/MS Spectrum - , negativeLC-MS/MSsplash10-001i-0900000000-cbe0a995dab473351f43
MS/MS Spectrum - , negativeLC-MS/MSsplash10-001i-0900000000-bfc42d662f222a7c16c7
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-3db475b164c0f884b93d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-2900000000-7e2deed118def434e8db
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0900000000-b2cc6b5ce2fe2affe47d
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0900000000-f45a65a00be3c0c36350
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-4e2e55783de4dffa779c
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-014i-2900000000-5d3c3f7eae0530449640
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-014i-2900000000-8f32c78a7ad999ed5b59
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-014i-1900000000-df22c4a5f012f7d3914d
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-014i-3900000000-417e15f416b540425ecc
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-12e93313926a2101dcf1
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-aea585c8fc7f724a3bc6
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-85c2a0ba04fda0bdc7c4
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-6be09c23029257292e1a
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-00kr-0900000000-571da212b666397543d8
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-014r-1900000000-e1eec402696987d15991
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-014i-3900000000-bf0285e7aab4ab522ed0
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-014l-9800000000-ed049e063ce3e87a0fee
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-014l-9300000000-977749d6f2a9be053e41
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-e3a7c00866297f9ae2f6
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-001i-9000000000-693fd974145cfcef734e
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-2ae60bff51be3b0f74e8
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-76add7d53e7aad5d2c3a
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-d6c4dab73fc569f2baa9
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-cc7f5485743f65658bb1
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-00kr-0900000000-26d3cd0998cde624afb0
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-014i-1900000000-95cae12913f0507dd9c7
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-014i-2900000000-e6272f676a9d06da1397
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-014l-8900000000-43e469fd6d4fc9d5d3ae
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-014l-9400000000-4ad9fd29953be2a398b9
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-0900000000-f0c3d42f28ff4440c36c
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-0900000000-e2c5e6873a4e7c0af421
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound 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
Aminopyrimidines and derivatives / Imidolactams / Imidazoles / Heteroaromatic compounds / Azacyclic compounds / Primary amines / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
6-aminopurine / Aminopyrimidine / Imidolactam / Pyrimidine / Heteroaromatic compound / Imidazole / Azole / Azacycle / Organic nitrogen compound / Organopnictogen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
6-aminopurines, purine nucleobase (CHEBI:16708) / purines (C00147) / a ring (ADENINE-RING)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Amp binding
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
Uniprot Name
Adenine phosphoribosyltransferase
Molecular Weight
19607.535 Da
References
  1. Barrett C, Alley J, Pulido JC, Spurling H, Li P, Parsons T, Mallender WD, Bembenek ME: Configuration of a scintillation proximity assay for the activity assessment of recombinant human adenine phosphoribosyltransferase. Assay Drug Dev Technol. 2006 Dec;4(6):661-9. [PubMed:17199504]
  2. Di Pietro V, Perruzza I, Amorini AM, Balducci A, Ceccarelli L, Lazzarino G, Barsotti P, Giardina B, Tavazzi B: Clinical, biochemical and molecular diagnosis of a compound homozygote for the 254 bp deletion-8 bp insertion of the APRT gene suffering from severe renal failure. Clin Biochem. 2007 Jan;40(1-2):73-80. Epub 2006 Oct 19. [PubMed:17126311]
  3. Katahira R, Ashihara H: Profiles of purine biosynthesis, salvage and degradation in disks of potato (Solanum tuberosum L.) tubers. Planta. 2006 Dec;225(1):115-26. Epub 2006 Jul 15. [PubMed:16845529]
  4. Katahira R, Ashihara H: Role of adenosine salvage in wound-induced adenylate biosynthesis in potato tuber slices. Plant Physiol Biochem. 2006 Oct;44(10):551-5. Epub 2006 Oct 9. [PubMed:17064924]
  5. Boitz JM, Ullman B: Leishmania donovani singly deficient in HGPRT, APRT or XPRT are viable in vitro and within mammalian macrophages. Mol Biochem Parasitol. 2006 Jul;148(1):24-30. Epub 2006 Mar 15. [PubMed:16597468]
  6. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
2. DNA
Kind
Nucleotide
Organism
Human
Pharmacological action
Unknown
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Simon R, Heithoff DM, Mahan MJ, Samuel CE: Comparison of tissue-selective proinflammatory gene induction in mice infected with wild-type, DNA adenine methylase-deficient, and flagellin-deficient Salmonella enterica. Infect Immun. 2007 Dec;75(12):5627-39. Epub 2007 Sep 24. [PubMed:17893133]
  4. Ichida H, Maeda K, Ichise H, Matsuyama T, Abe T, Yoneyama K, Koba T: In silico restriction landmark genome scanning analysis of Xanthomonas oryzae pathovar oryzae MAFF 311018. Biochem Biophys Res Commun. 2007 Nov 23;363(3):852-6. Epub 2007 Sep 24. [PubMed:17904519]
  5. Mamdouh W, Dong M, Kelly RE, Kantorovich LN, Besenbacher F: Coexistence of homochiral and heterochiral adenine domains at the liquid/solid interface. J Phys Chem B. 2007 Oct 25;111(42):12048-52. Epub 2007 Oct 5. [PubMed:17918893]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
S-methyl-5-thioadenosine phosphorylase activity
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 biosynth...
Gene Name
MTAP
Uniprot ID
Q13126
Uniprot Name
S-methyl-5'-thioadenosine phosphorylase
Molecular Weight
31235.76 Da
References
  1. Chow WA, Bedell V, Gaytan P, Borden E, Goldblum J, Hicks D, Slovak ML: Methylthioadenosine phosphorylase gene deletions are frequently detected by fluorescence in situ hybridization in conventional chondrosarcomas. Cancer Genet Cytogenet. 2006 Apr 15;166(2):95-100. [PubMed:16631464]
  2. Chattopadhyay S, Zhao R, Tsai E, Schramm VL, Goldman ID: The effect of a novel transition state inhibitor of methylthioadenosine phosphorylase on pemetrexed activity. Mol Cancer Ther. 2006 Oct;5(10):2549-55. [PubMed:17041099]
  3. Singh V, Schramm VL: Transition-state structure of human 5'-methylthioadenosine phosphorylase. J Am Chem Soc. 2006 Nov 15;128(45):14691-6. [PubMed:17090056]
Kind
Protein
Organism
Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
Pharmacological action
Unknown
General Function
Nicotinate-nucleotide-dimethylbenzimidazole phosphoribosyltransferase activity
Specific Function
Catalyzes the synthesis of alpha-ribazole-5'-phosphate from nicotinate mononucleotide (NAMN) and 5,6-dimethylbenzimidazole (DMB).
Gene Name
cobT
Uniprot ID
Q05603
Uniprot Name
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase
Molecular Weight
36612.305 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Maggio-Hall LA, Escalante-Semerena JC: Alpha-5,6-dimethylbenzimidazole adenine dinucleotide (alpha-DAD), a putative new intermediate of coenzyme B12 biosynthesis in Salmonella typhimurium. Microbiology. 2003 Apr;149(Pt 4):983-90. [PubMed:12686640]
  4. Cheong CG, Escalante-Semerena JC, Rayment I: Structural investigation of the biosynthesis of alternative lower ligands for cobamides by nicotinate mononucleotide: 5,6-dimethylbenzimidazole phosphoribosyltransferase from Salmonella enterica. J Biol Chem. 2001 Oct 5;276(40):37612-20. Epub 2001 Jul 5. [PubMed:11441022]
  5. Trzebiatowski JR, Escalante-Semerena JC: Purification and characterization of CobT, the nicotinate-mononucleotide:5,6-dimethylbenzimidazole phosphoribosyltransferase enzyme from Salmonella typhimurium LT2. J Biol Chem. 1997 Jul 11;272(28):17662-7. [PubMed:9211916]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Catalyzes the ATP-dependent carboxylation of acetyl-CoA to malonyl-CoA. Carries out three functions: biotin carboxyl carrier protein, biotin carboxylase and carboxyltransferase. Involved in inhibit...
Gene Name
ACACB
Uniprot ID
O00763
Uniprot Name
Acetyl-CoA carboxylase 2
Molecular Weight
276538.575 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Rasmussen JT, Rosendal J, Knudsen J: Interaction of acyl-CoA binding protein (ACBP) on processes for which acyl-CoA is a substrate, product or inhibitor. Biochem J. 1993 Jun 15;292 ( Pt 3):907-13. [PubMed:8318018]
  4. Witters LA, Mendel DB, Colliton JW: Modulation of acetyl-CoA carboxylase by inhibitors of IMP dehydrogenase: implications for insulin regulation. Arch Biochem Biophys. 1987 Jan;252(1):130-5. [PubMed:2880560]
  5. Itani SI, Saha AK, Kurowski TG, Coffin HR, Tornheim K, Ruderman NB: Glucose autoregulates its uptake in skeletal muscle: involvement of AMP-activated protein kinase. Diabetes. 2003 Jul;52(7):1635-40. [PubMed:12829626]
  6. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Non-membrane spanning protein tyrosine phosphatase activity
Specific Function
Acts on tyrosine phosphorylated proteins, low-MW aryl phosphates and natural and synthetic acyl phosphates. Isoform 3 does not possess phosphatase activity.
Gene Name
ACP1
Uniprot ID
P24666
Uniprot Name
Low molecular weight phosphotyrosine protein phosphatase
Molecular Weight
18042.315 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Wang S, Stauffacher CV, Van Etten RL: Structural and mechanistic basis for the activation of a low-molecular weight protein tyrosine phosphatase by adenine. Biochemistry. 2000 Feb 15;39(6):1234-42. [PubMed:10684601]
  4. Magherini F, Gamberi T, Paoli P, Marchetta M, Biagini M, Raugei G, Camici G, Ramponi G, Modesti A: The in vivo tyrosine phosphorylation level of yeast immunophilin Fpr3 is influenced by the LMW-PTP Ltp1. Biochem Biophys Res Commun. 2004 Aug 20;321(2):424-31. [PubMed:15358193]
  5. Ostanin K, Pokalsky C, Wang S, Van Etten RL: Cloning and characterization of a Saccharomyces cerevisiae gene encoding the low molecular weight protein-tyrosine phosphatase. J Biol Chem. 1995 Aug 4;270(31):18491-9. [PubMed:7629177]
  6. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Methylthioadenosine 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'-methylthiorib...
Gene Name
mtnN
Uniprot ID
P0AF12
Uniprot Name
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase
Molecular Weight
24353.725 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Singh V, Lee JE, Nunez S, Howell PL, Schramm VL: Transition state structure of 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase from Escherichia coli and its similarity to transition state analogues. Biochemistry. 2005 Sep 6;44(35):11647-59. [PubMed:16128565]
  4. Walker RD, Duerre JA: S-adenosylhomocysteine metabolism in various species. Can J Biochem. 1975 Mar;53(3):312-9. [PubMed:1125818]
  5. Singh V, Schramm VL: Transition-state analysis of S. pneumoniae 5'-methylthioadenosine nucleosidase. J Am Chem Soc. 2007 Mar 14;129(10):2783-95. Epub 2007 Feb 14. [PubMed:17298059]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Not Available
Specific Function
Not Available
Gene Name
PECR
Uniprot ID
Q9BY49
Uniprot Name
Peroxisomal trans-2-enoyl-CoA reductase
Molecular Weight
32544.11 Da
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Adenine glycosylase active on G-A mispairs. MutY also corrects error-prone DNA synthesis past GO lesions which are due to the oxidatively damaged form of guanine: 7,8-dihydro-8-oxoguanine (8-oxo-dG...
Gene Name
mutY
Uniprot ID
P17802
Uniprot Name
Adenine DNA glycosylase
Molecular Weight
39148.835 Da
Kind
Protein
Organism
Lactobacillus helveticus
Pharmacological action
Unknown
General Function
Nucleoside deoxyribosyltransferase activity
Specific Function
Not Available
Gene Name
ptd
Uniprot ID
Q8RLY5
Uniprot Name
Nucleoside 2-deoxyribosyltransferase
Molecular Weight
18713.08 Da
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Protein serine/threonine kinase activity
Specific Function
Serine/arginine-rich protein-specific kinase which specifically phosphorylates its substrates at serine residues located in regions rich in arginine/serine dipeptides, known as RS domains and is in...
Gene Name
SRPK2
Uniprot ID
P78362
Uniprot Name
SRSF protein kinase 2
Molecular Weight
77525.955 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Thermus thermophilus (strain HB8 / ATCC 27634 / DSM 579)
Pharmacological action
Unknown
General Function
Four-way junction helicase activity
Specific Function
The RuvA-RuvB complex in the presence of ATP renatures cruciform structure in supercoiled DNA with palindromic sequence, indicating that it may promote strand exchange reactions in homologous recom...
Gene Name
ruvB
Uniprot ID
Q5SL87
Uniprot Name
Holliday junction ATP-dependent DNA helicase RuvB
Molecular Weight
35973.305 Da

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name
UGT1A1
Uniprot ID
P22309
Uniprot Name
UDP-glucuronosyltransferase 1-1
Molecular Weight
59590.91 Da
References
  1. Nishimura Y, Maeda S, Ikushiro S, Mackenzie PI, Ishii Y, Yamada H: Inhibitory effects of adenine nucleotides and related substances on UDP-glucuronosyltransferase: structure-effect relationships and evidence for an allosteric mechanism. Biochim Biophys Acta. 2007 Nov;1770(11):1557-66. Epub 2007 Aug 8. [PubMed:17764847]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 17:33