Guanine

Identification

Generic Name
Guanine
DrugBank Accession Number
DB02377
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 151.1261
Monoisotopic: 151.049409807
Chemical Formula
C5H5N5O
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UPurine nucleoside phosphorylaseNot AvailableHumans
UPurine nucleoside phosphorylase 2Not AvailableEscherichia coli (strain K12)
UXanthine phosphoribosyltransferaseNot AvailableEscherichia coli (strain K12)
UGTP cyclohydrolase 1
inhibitor
Humans
UPurine nucleoside phosphorylaseNot AvailableThermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
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

Adverse Effects
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Toxicity

Not Available

Pathways
PathwayCategory
Adenylosuccinate Lyase DeficiencyDisease
Xanthine Dehydrogenase Deficiency (Xanthinuria)Disease
Xanthinuria Type IDisease
Mitochondrial DNA Depletion SyndromeDisease
Myoadenylate Deaminase DeficiencyDisease
Purine MetabolismMetabolic
Purine Nucleoside Phosphorylase DeficiencyDisease
Lesch-Nyhan Syndrome (LNS)Disease
Gout or Kelley-Seegmiller SyndromeDisease
Mercaptopurine Action PathwayDrug action
Adenine Phosphoribosyltransferase Deficiency (APRT)Disease
Adenosine Deaminase DeficiencyDisease
AICA-RibosiduriaDisease
Molybdenum Cofactor DeficiencyDisease
Azathioprine Action PathwayDrug action
Thioguanine Action PathwayDrug action
Xanthinuria Type IIDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe therapeutic efficacy of 1,2-Benzodiazepine can be decreased when used in combination with Guanine.
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Guanine.
AcetazolamideAcetazolamide may increase the excretion rate of Guanine which could result in a lower serum level and potentially a reduction in efficacy.
AdalimumabThe serum concentration of Guanine can be decreased when it is combined with Adalimumab.
AdenosineThe therapeutic efficacy of Adenosine can be decreased when used in combination with Guanine.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as purines and purine derivatives. These are aromatic heterocyclic compounds containing a purine moiety, which is formed a pyrimidine-ring ring fused to an imidazole ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Imidazopyrimidines
Sub Class
Purines and purine derivatives
Direct Parent
Purines and purine derivatives
Alternative Parents
Hydroxypyrimidines / Imidazoles / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Hydrocarbon derivatives
Substituents
Aromatic heteropolycyclic compound / Azacycle / Azole / Heteroaromatic compound / Hydrocarbon derivative / Hydroxypyrimidine / Imidazole / Organic nitrogen compound / Organic oxygen compound / Organonitrogen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
oxopurine, 2-aminopurines, purine nucleobase (CHEBI:16235) / purines (C00242) / a purine base, a purine (GUANINE)
Affected organisms
Not Available

Chemical Identifiers

UNII
5Z93L87A1R
CAS number
73-40-5
InChI Key
UYTPUPDQBNUYGX-UHFFFAOYSA-N
InChI
InChI=1S/C5H5N5O/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)
IUPAC Name
2-amino-6,7-dihydro-3H-purin-6-one
SMILES
NC1=NC(=O)C2=C(N1)N=CN2

References

Synthesis Reference

Takeo Suzuki, Toshihide Nakanishi, "(2'-Amino-2'-deoxypentofuranosyl) guanine and process for producing same." U.S. Patent US3987030, issued April, 1966.

US3987030
General References
Not Available
Human Metabolome Database
HMDB0000132
KEGG Compound
C00242
PubChem Compound
764
PubChem Substance
46507057
ChemSpider
744
BindingDB
50200094
RxNav
1372539
ChEBI
16235
ChEMBL
CHEMBL219568
ZINC
ZINC000000895129
Therapeutic Targets Database
DNC000709
PDBe Ligand
GUN
RxList
RxList Drug Page
Wikipedia
Guanine
PDB Entries
1a95 / 1d6a / 1it7 / 1sql / 1ulb / 1v2h / 1vmk / 1wet / 1xe7 / 1xt4
show 53 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentHealthy Adult Subjects1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)360 dec °CPhysProp
water solubility2080 mg/L (at 37 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-0.91HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility2.31 mg/mLALOGPS
logP-0.92ALOGPS
logP-0.59Chemaxon
logS-1.8ALOGPS
pKa (Strongest Acidic)9.13Chemaxon
pKa (Strongest Basic)3.42Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area96.16 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity38.9 m3·mol-1Chemaxon
Polarizability13.34 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9948
Blood Brain Barrier+0.9672
Caco-2 permeable-0.643
P-glycoprotein substrateNon-substrate0.6965
P-glycoprotein inhibitor INon-inhibitor0.9429
P-glycoprotein inhibitor IINon-inhibitor0.9564
Renal organic cation transporterNon-inhibitor0.8827
CYP450 2C9 substrateNon-substrate0.8436
CYP450 2D6 substrateNon-substrate0.8044
CYP450 3A4 substrateNon-substrate0.6861
CYP450 1A2 substrateNon-inhibitor0.7982
CYP450 2C9 inhibitorNon-inhibitor0.9503
CYP450 2D6 inhibitorNon-inhibitor0.9109
CYP450 2C19 inhibitorNon-inhibitor0.8364
CYP450 3A4 inhibitorNon-inhibitor0.8664
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9747
Ames testNon AMES toxic0.591
CarcinogenicityNon-carcinogens0.9624
BiodegradationNot ready biodegradable0.9618
Rat acute toxicity2.3231 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.961
hERG inhibition (predictor II)Non-inhibitor0.9226
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0udi-1938000000-e15e09f2007f35659bb9
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-0udi-3739000000-66a080b08ba9b9f82e20
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0ff0-5900000000-f103c75addeafe7ac6f0
GC-MS Spectrum - EI-BGC-MSsplash10-0udi-5900000000-0a63148e3a8dc8d026df
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0udi-1938000000-e15e09f2007f35659bb9
GC-MS Spectrum - GC-MSGC-MSsplash10-0udi-3739000000-66a080b08ba9b9f82e20
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0udi-2928000000-073bf70794fe99ce737f
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-000t-2790000000-77e6b5b71c9ff6ad2b23
Mass Spectrum (Electron Ionization)MSsplash10-0udi-8900000000-699c510cfaf838ab1922
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0udi-0901000000-2864e73c83444d566e9a
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0a4i-2900000000-4229d3d01623054b4ceb
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-0900000000-d5ae84fefadd84f988b4
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-001i-0900000000-7d48b2e8db6967e98407
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0uxr-0900000000-67a7784963ec75cecaa0
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-00di-9000000000-4569516f23d8a712b434
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-001i-0900000000-d928cac1226f19b8edc3
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0udi-0900000000-34059351f2cbd94a8acc
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0udj-0903100000-deb9c022884d7c98782e
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-001i-0900000000-45d9db80ce4657ef1773
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-004i-1900000000-86b7ee5755cbb8236f5b
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0udi-0900000000-ba534850b64f39d81fa0
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-0udi-0900000000-422f992621ab9626d1b2
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-0f89-0900000000-64e388178db73f06cb20
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0udi-0900000000-f0a95c55947ca990359c
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-001i-0900000000-45d9db80ce4657ef1773
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0udi-0900000000-ba534850b64f39d81fa0
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0f89-0900000000-64e388178db73f06cb20
MS/MS Spectrum - , negativeLC-MS/MSsplash10-0udi-0900000000-c2e1c1e8841cc741dac1
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0900000000-0840e50df6a1013fdd24
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-2900000000-4229d3d01623054b4ceb
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-d5ae84fefadd84f988b4
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-d77cafe24ec50283bbf8
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0900000000-34059351f2cbd94a8acc
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0900000000-422f992621ab9626d1b2
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0f89-0900000000-074d4bf3ce668d5a6900
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-714e5dfba49cbafda02e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-e156b5aa1f200117b282
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-0e19d835426224afce47
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-4900000000-b79c4409d9058f952fdf
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0pb9-9700000000-04f95d0920d3d7d7bb2a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014l-9100000000-c2e8e2967e6fea843b7d
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-127.8850631
predicted
DarkChem Lite v0.1.0
[M-H]-128.0296631
predicted
DarkChem Lite v0.1.0
[M-H]-128.0685631
predicted
DarkChem Lite v0.1.0
[M-H]-127.7062
predicted
DeepCCS 1.0 (2019)
[M+H]+127.6530631
predicted
DarkChem Lite v0.1.0
[M+H]+127.5889631
predicted
DarkChem Lite v0.1.0
[M+H]+127.4798631
predicted
DarkChem Lite v0.1.0
[M+H]+130.98537
predicted
DeepCCS 1.0 (2019)
[M+Na]+128.4593631
predicted
DarkChem Lite v0.1.0
[M+Na]+128.1461631
predicted
DarkChem Lite v0.1.0
[M+Na]+128.0385631
predicted
DarkChem Lite v0.1.0
[M+Na]+140.0542
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
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 ...
Gene Name
PNP
Uniprot ID
P00491
Uniprot Name
Purine nucleoside phosphorylase
Molecular Weight
32117.69 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. [Article]
  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. [Article]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
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 ...
Gene Name
xapA
Uniprot ID
P45563
Uniprot Name
Purine nucleoside phosphorylase 2
Molecular Weight
29834.38 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. [Article]
  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. [Article]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Xanthine phosphoribosyltransferase activity
Specific Function
Acts on guanine, xanthine and to a lesser extent hypoxanthine.
Gene Name
gpt
Uniprot ID
P0A9M5
Uniprot Name
Xanthine phosphoribosyltransferase
Molecular Weight
16970.455 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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Positively regulates nitric oxide synthesis in umbilical vein endothelial cells (HUVECs). May be involved in dopamine synthesis. May modify pain sensitivity and persistence. Isoform GCH-1 is the fu...
Gene Name
GCH1
Uniprot ID
P30793
Uniprot Name
GTP cyclohydrolase 1
Molecular Weight
27902.855 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Kind
Protein
Organism
Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
Pharmacological action
Unknown
General Function
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 ...
Gene Name
Not Available
Uniprot ID
Q9X1T2
Uniprot Name
Purine nucleoside phosphorylase
Molecular Weight
29172.84 Da

Drug created at June 13, 2005 13:24 / Updated at July 02, 2020 13:15