Identification
NameGuanine
Accession NumberDB02377  (EXPT01672)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External IDs Not Available
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNII5Z93L87A1R
CAS number73-40-5
WeightAverage: 151.1261
Monoisotopic: 151.049409807
Chemical FormulaC5H5N5O
InChI KeyUYTPUPDQBNUYGX-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
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Purine nucleoside phosphorylaseProteinunknownNot AvailableHumanP00491 details
Purine nucleoside phosphorylase 2ProteinunknownNot AvailableEscherichia coli (strain K12)P45563 details
Xanthine phosphoribosyltransferaseProteinunknownNot AvailableEscherichia coli (strain K12)P0A9M5 details
GTP cyclohydrolase 1Proteinunknown
inhibitor
HumanP30793 details
Purine nucleoside phosphorylaseProteinunknownNot AvailableThermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)Q9X1T2 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Lesch-Nyhan Syndrome (LNS)DiseaseSMP00364
Myoadenylate deaminase deficiencyDiseaseSMP00537
Gout or Kelley-Seegmiller SyndromeDiseaseSMP00365
Azathioprine Action PathwayDrug actionSMP00427
Xanthinuria type IIDiseaseSMP00513
Purine MetabolismMetabolicSMP00050
Adenosine Deaminase DeficiencyDiseaseSMP00144
Xanthine Dehydrogenase Deficiency (Xanthinuria)DiseaseSMP00220
Adenylosuccinate Lyase DeficiencyDiseaseSMP00167
Molybdenum Cofactor DeficiencyDiseaseSMP00203
Purine Nucleoside Phosphorylase DeficiencyDiseaseSMP00210
Adenine phosphoribosyltransferase deficiency (APRT)DiseaseSMP00535
Mitochondrial DNA depletion syndromeDiseaseSMP00536
AICA-RibosiduriaDiseaseSMP00168
Mercaptopurine Action PathwayDrug actionSMP00428
Thioguanine Action PathwayDrug actionSMP00430
Xanthinuria type IDiseaseSMP00512
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot 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 ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
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
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0udi-1938000000-e15e09f2007f35659bb9View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0udi-3739000000-66a080b08ba9b9f82e20View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
GC-MSGC-MS Spectrum - EI-Bsplash10-0udi-5900000000-0a63148e3a8dc8d026dfView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0udi-2928000000-073bf70794fe99ce737fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-000t-2790000000-77e6b5b71c9ff6ad2b23View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-000t-2790000000-77e6b5b71c9ff6ad2b23View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0901000000-2864e73c83444d566e9aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-2900000000-4229d3d01623054b4cebView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-d5ae84fefadd84f988b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-7d48b2e8db6967e98407View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0uxr-0900000000-67a7784963ec75cecaa0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-9000000000-4569516f23d8a712b434View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-d928cac1226f19b8edc3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0900000000-34059351f2cbd94a8accView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udj-0903100000-deb9c022884d7c98782eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0900000000-45d9db80ce4657ef1773View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-1900000000-86b7ee5755cbb8236f5bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0900000000-ba534850b64f39d81fa0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-0900000000-422f992621ab9626d1b2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0f89-0900000000-64e388178db73f06cb20View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0udi-0900000000-f0a95c55947ca990359cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0900000000-c2e1c1e8841cc741dac1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0900000000-0840e50df6a1013fdd24View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ , positivesplash10-001i-0900000000-d77cafe24ec50283bbf8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0f89-0900000000-074d4bf3ce668d5a6900View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-e74c005384d71f4787e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-de4a4c4479ea93d742b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5i-9800000000-da506476184e5c2313a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-03d17084c3cb072c0237View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2900000000-c372e3ba919cba4f561fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9200000000-8ac435f998deda6437e1View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0udi-8900000000-699c510cfaf838ab1922View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassImidazopyrimidines
Direct ParentPurines and purine derivatives
Alternative ParentsHydroxypyrimidines / Imidazoles / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Hydrocarbon derivatives
SubstituentsPurine / Hydroxypyrimidine / Pyrimidine / Heteroaromatic compound / Imidazole / Azole / Azacycle / Organic nitrogen compound / Organic oxygen compound / Organopnictogen compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptorsoxopurine, 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 bases and pentose-1-phosphate.
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 bases and pentose-1-phosphate. This protein can degrade all purine nucleosides including xanthosine, inosine and guanosine, but cannot cleave adenosine, deoxyadenosine or hypoxanthine arabinoside. Has...
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 functional enzyme, the potential function of the enzymatically inactive isoforms remains unknown.
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 bases and pentose-1-phosphate.
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 August 02, 2017 16:42