Identification

Name
Guanine
Accession Number
DB02377  (EXPT01672)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
5Z93L87A1R
CAS number
73-40-5
Weight
Average: 151.1261
Monoisotopic: 151.049409807
Chemical Formula
C5H5N5O
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

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UPurine nucleoside phosphorylaseNot AvailableHuman
UPurine nucleoside phosphorylase 2Not AvailableEscherichia coli (strain K12)
UXanthine phosphoribosyltransferaseNot AvailableEscherichia coli (strain K12)
UGTP cyclohydrolase 1
inhibitor
Human
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
Toxicity
Not Available
Affected organisms
Not Available
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
Not Available
Food Interactions
Not Available

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
External Links
Human Metabolome Database
HMDB00132
KEGG Compound
C00242
ChemSpider
744
BindingDB
50200094
ChEBI
16235
ChEMBL
CHEMBL219568
Therapeutic Targets Database
DNC000709
HET
GUN
RxList
RxList Drug Page
Wikipedia
Guanine
ATC Codes
Not Available
AHFS Codes
Not Available
PDB Entries
FDA label
Not Available
MSDS
Not Available

Clinical Trials

Clinical Trials
Not Available

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)8.95ChemAxon
pKa (Strongest Basic)2.22ChemAxon
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-MSNot Available
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-e74c005384d71f4787e5
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-de4a4c4479ea93d742b5
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a5i-9800000000-da506476184e5c2313a4
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-03d17084c3cb072c0237
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-2900000000-c372e3ba919cba4f561f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kf-9200000000-8ac435f998deda6437e1
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
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 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
Purine / Hydroxypyrimidine / Pyrimidine / Heteroaromatic compound / Imidazole / Azole / Azacycle / Organic nitrogen compound / Organic oxygen compound / Organopnictogen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
oxopurine, 2-aminopurines, purine nucleobase (CHEBI:16235) / purines (C00242) / a purine base, a purine (GUANINE)

Targets

Kind
Protein
Organism
Human
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. [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]
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. [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]
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. [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]
Kind
Protein
Organism
Human
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. [PubMed:11752352]
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 on June 13, 2005 07:24 / Updated on October 02, 2017 05:10