You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Bovine Metabolome Database.
Record Information
Version1.0
Creation Date2016-09-30 22:19:59 UTC
Update Date2020-06-04 20:46:51 UTC
BMDB IDBMDB0000132
Secondary Accession Numbers
  • BMDB00132
Metabolite Identification
Common NameGuanine
DescriptionGuanine, also known as G or mearlmaid aa, 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. Guanine exists as a solid, possibly soluble (in water), and a moderately basic compound (based on its pKa) molecule. Guanine exists in all living species, ranging from bacteria to humans. Guanine has been found to be associated with several diseases known as colorectal cancer, alzheimer's disease, lewy body disease, and frontotemporal dementia; also guanine has been linked to the inborn metabolic disorders including lesch-nyhan syndrome.
Structure
Thumb
Synonyms
ValueSource
2-Amino-6-hydroxypurineChEBI
2-Amino-6-oxopurineChEBI
GChEBI
GuaChEBI
2-Amino-1,7-dihydro-6H-purin-6-oneHMDB
2-Amino-1,9-dihydro-6H-purin-6-oneHMDB
2-Amino-1,9-dihydro-purin-6-oneHMDB
2-Amino-3,7-dihydro-6H-purin-6-oneHMDB
2-Amino-6-hydroxy-1H-purineHMDB
2-Amino-6-purinolHMDB
2-Amino-hypoxanthineHMDB
2-AminohypoxanthineHMDB
6-Hydroxy-2-aminopurineHMDB
C.I. natural white 1HMDB
CI natural white 1HMDB
Dew pearlHMDB
GuaninHMDB
Guanine enolHMDB
GUNHMDB
MearlmaidHMDB
Mearlmaid aaHMDB
Natural pearl essenceHMDB
Natural white 1HMDB
NaturonHMDB
PathocidinHMDB
Pearl essenceHMDB
Stella polarisHMDB
Chemical FormulaC5H5N5O
Average Molecular Weight151.1261
Monoisotopic Molecular Weight151.049409807
IUPAC Name2-amino-6,7-dihydro-3H-purin-6-one
Traditional Name2-aminohypoxanthine
CAS Registry Number73-40-5
SMILES
NC1=NC(=O)C2=C(N1)N=CN2
InChI Identifier
InChI=1S/C5H5N5O/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)
InChI KeyUYTPUPDQBNUYGX-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentPurines and purine derivatives
Alternative Parents
Substituents
  • Purine
  • Hydroxypyrimidine
  • Pyrimidine
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Myelin sheath
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point360 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.08 mg/mL at 37 °CNot Available
LogP-0.91HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
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 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity38.9 m³·mol⁻¹ChemAxon
Polarizability13.34 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Myelin sheath
Biospecimen Locations
  • Epidermis
  • Fibroblasts
  • Intestine
  • Mammary Gland
  • Milk
  • Neuron
  • Placenta
  • Prostate Tissue
  • Skeletal Muscle
  • Spleen
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified6.5 uMNot SpecifiedNot Specified
Normal
details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Skeletal MuscleExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
SpleenExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
TestisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000132
DrugBank IDDB02377
Phenol Explorer Compound IDNot Available
FooDB IDFDB004222
KNApSAcK IDC00001501
Chemspider ID744
KEGG Compound IDC00242
BioCyc IDGUANINE
BiGG ID34363
Wikipedia LinkGuanine
METLIN ID315
PubChem Compound764
PDB IDNot Available
ChEBI ID16235
References
Synthesis ReferenceXiao, Xuhua; Ma, Weiyong. One-pot synthesis of guanine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 10pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Tiemeyer W, Stohrer M, Giesecke D: Metabolites of nucleic acids in bovine milk. J Dairy Sci. 1984 Apr;67(4):723-8. doi: 10.3168/jds.S0022-0302(84)81361-2. [PubMed:6539345 ]

Enzymes

General function:
Nucleotide transport and metabolism
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:
Q56JW4
Molecular weight:
19537.0
Reactions
Guanosine monophosphate + Pyrophosphate → Guanine + Phosphoribosyl pyrophosphatedetails
General function:
Nucleotide transport and metabolism
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 (By similarity).
Gene Name:
HPRT1
Uniprot ID:
Q3SZ18
Molecular weight:
24498.0
Reactions
Guanosine monophosphate + Pyrophosphate → Guanine + Phosphoribosyl pyrophosphatedetails
General function:
Nucleotide transport and metabolism
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:
P55859
Molecular weight:
32037.0
Reactions
Guanosine + Hydrogen phosphate → Guanine + Ribose 1-phosphatedetails
Deoxyguanosine + Hydrogen phosphate → Guanine + Deoxyribose 1-phosphatedetails
General function:
Involved in acyl binding
Specific function:
Functions as signal transducer for the rod photoreceptor RHO (PubMed:21285355, PubMed:23303210, PubMed:28655769, PubMed:8259210). Required for normal RHO-mediated light perception by the retina (By similarity). Guanine nucleotide-binding proteins (G proteins) function as transducers downstream of G protein-coupled receptors (GPCRs), such as the photoreceptor RHO. The alpha chain contains the guanine nucleotide binding site and alternates between an active, GTP-bound state and an inactive, GDP-bound state (PubMed:21285355, PubMed:28655769, PubMed:8259210, PubMed:8208289, PubMed:7969474). Activated RHO promotes GDP release and GTP binding (PubMed:21285355, PubMed:28655769). Signaling is mediated via downstream effector proteins, such as cGMP-phosphodiesterase (PubMed:21285355).
Gene Name:
GNAT1
Uniprot ID:
P04695
Molecular weight:
39966.0
General function:
Involved in GTP binding
Specific function:
Guanine nucleotide-binding protein (G protein) alpha subunit playing a prominent role in bitter and sweet taste transduction as well as in umami (monosodium glutamate, monopotassium glutamate, and inosine monophosphate) taste transduction.
Gene Name:
GNAT3
Uniprot ID:
P0C7Q4
Molecular weight:
40332.0
General function:
Involved in signal transducer activity
Specific function:
Guanine nucleotide-binding proteins (G proteins) are involved as a modulator or transducer in various transmembrane signaling systems. The beta and gamma chains are required for the GTPase activity, for replacement of GDP by GTP, and for G protein-effector interaction.
Gene Name:
GNG11
Uniprot ID:
Q5E9F0
Molecular weight:
8594.0
General function:
Involved in GTP binding
Specific function:
Guanine nucleotide-binding proteins (G proteins) are involved as modulators or transducers in various transmembrane signaling systems. Transducin is an amplifier and one of the transducers of a visual impulse that performs the coupling between rhodopsin and cGMP-phosphodiesterase.
Gene Name:
GNAT2
Uniprot ID:
P04696
Molecular weight:
40144.0
General function:
Involved in GTP binding
Specific function:
GTPase that associates with pre-60S ribosomal subunits in the nucleolus and is required for their nuclear export and maturation.
Gene Name:
GNL2
Uniprot ID:
Q2YDL0
Molecular weight:
83469.0
General function:
Involved in GTP binding
Specific function:
Guanine nucleotide-binding proteins (G proteins) are involved as modulators or transducers in various transmembrane signaling systems. Acts as an activator of phospholipase C. Transduces FFAR4 signaling in response to long-chain fatty acids (LCFAs).
Gene Name:
GNA11
Uniprot ID:
P38409
Molecular weight:
42070.0
General function:
Involved in GTP binding
Specific function:
Not Available
Gene Name:
GNAI3
Uniprot ID:
Q3ZCA7
Molecular weight:
40536.0
General function:
Involved in GTPase activity
Specific function:
Guanine nucleotide-binding proteins (G proteins) are involved as a modulator or transducer in various transmembrane signaling systems. The beta and gamma chains are required for the GTPase activity, for replacement of GDP by GTP, and for G protein-effector interaction.
Gene Name:
GNB2
Uniprot ID:
P11017
Molecular weight:
37331.0
General function:
Involved in GTP binding
Specific function:
Guanine nucleotide-binding proteins (G proteins) are involved as modulators or transducers in various transmembrane signaling systems.
Gene Name:
GNA14
Uniprot ID:
P38408
Molecular weight:
41499.0
General function:
Involved in signal transducer activity
Specific function:
Guanine nucleotide-binding proteins (G proteins) are involved as a modulator or transducer in various transmembrane signaling systems. The beta and gamma chains are required for the GTPase activity, for replacement of GDP by GTP, and for G protein-effector interaction.
Gene Name:
GNG12
Uniprot ID:
Q28024
Molecular weight:
8057.0
General function:
Involved in GTP binding
Specific function:
Guanine nucleotide-binding proteins (G proteins) function as transducers in numerous signaling pathways controlled by G protein-coupled receptors (GPCRs). Signaling involves the activation of adenylyl cyclases, resulting in increased levels of the signaling molecule cAMP (PubMed:2022671, PubMed:9395396, PubMed:11087399, PubMed:15591060, PubMed:16766715, PubMed:19243146). GNAS functions downstream of several GPCRs, including beta-adrenergic receptors. Stimulates the Ras signaling pathway via RAPGEF2 (By similarity).
Gene Name:
GNAS
Uniprot ID:
P04896
Molecular weight:
45709.0
General function:
Involved in GTP binding
Specific function:
Guanine nucleotide-binding proteins (G proteins) function as transducers downstream of G protein-coupled receptors (GPCRs) in numerous signaling cascades. The alpha chain contains the guanine nucleotide binding site and alternates between an active, GTP-bound state and an inactive, GDP-bound state. Signaling by an activated GPCR promotes GDP release and GTP binding. The alpha subunit has a low GTPase activity that converts bound GTP to GDP, thereby terminating the signal. Both GDP release and GTP hydrolysis are modulated by numerous regulatory proteins (By similarity). Signaling is mediated via effector proteins, such as adenylate cyclase. Inhibits adenylate cyclase activity, leading to decreased intracellular cAMP levels (By similarity). The inactive GDP-bound form prevents the association of RGS14 with centrosomes and is required for the translocation of RGS14 from the cytoplasm to the plasma membrane. Required for normal cytokinesis during mitosis (By similarity). Required for cortical dynein-dynactin complex recruitment during metaphase (By similarity).
Gene Name:
GNAI1
Uniprot ID:
P63097
Molecular weight:
40361.0
General function:
Involved in GTP binding
Specific function:
Not Available
Gene Name:
Gnas
Uniprot ID:
Q6U8D6
Molecular weight:
23994.0
General function:
Involved in signal transducer activity
Specific function:
Guanine nucleotide-binding proteins (G proteins) are involved as a modulator or transducer in various transmembrane signaling systems. The beta and gamma chains are required for the GTPase activity, for replacement of GDP by GTP, and for G protein-effector interaction.
Gene Name:
GNG3
Uniprot ID:
P63214
Molecular weight:
8305.0
General function:
Involved in activation of phospholipase C activity by G
Specific function:
Not Available
Gene Name:
GNB1
Uniprot ID:
A7E3V7
Molecular weight:
37030.0
General function:
Involved in GTP binding
Specific function:
Stabilizes TERF1 telomeric association by preventing TERF1 recruitment by PML. Stabilizes TERF1 protein by preventing its ubiquitination and hence proteasomal degradation. Does so by interfering with TERF1-binding to FBXO4 E3 ubiquitin-protein ligase. Required for cell proliferation. By stabilizing TRF1 protein during mitosis, promotes metaphase-to-anaphase transition. Stabilizes MDM2 protein by preventing its ubiquitination, and hence proteasomal degradation. By acting on MDM2, may affect TP53 activity. Required for normal processing of ribosomal pre-rRNA. Binds GTP (By similarity).
Gene Name:
GNL3L
Uniprot ID:
Q3T0J9
Molecular weight:
64837.0
General function:
Involved in signal transducer activity
Specific function:
Guanine nucleotide-binding proteins (G proteins) are involved as a modulator or transducer in various transmembrane signaling systems. The beta and gamma chains are required for the GTPase activity, for replacement of GDP by GTP, and for G protein-effector interaction.
Gene Name:
GNGT1
Uniprot ID:
P02698
Molecular weight:
8544.0
General function:
Involved in GTP binding
Specific function:
Guanine nucleotide-binding proteins (G proteins) are involved as modulators or transducers in various transmembrane signaling systems. The G(o) protein function is not clear. Stimulated by RGS14 (By similarity).
Gene Name:
GNAO1
Uniprot ID:
P08239
Molecular weight:
40067.0
General function:
Involved in signal transducer activity
Specific function:
Guanine nucleotide-binding proteins (G proteins) are involved as a modulator or transducer in various transmembrane signaling systems. The beta and gamma chains are required for the GTPase activity, for replacement of GDP by GTP, and for G protein-effector interaction.
Gene Name:
GNGT2
Uniprot ID:
P50154
Molecular weight:
7728.0
General function:
Involved in signal transducer activity
Specific function:
Guanine nucleotide-binding proteins (G proteins) are involved as a modulator or transducer in various transmembrane signaling systems. The beta and gamma chains are required for the GTPase activity, for replacement of GDP by GTP, and for G protein-effector interaction.
Gene Name:
GNG5
Uniprot ID:
P63217
Molecular weight:
7318.0
General function:
Involved in signal transducer activity
Specific function:
Guanine nucleotide-binding proteins (G proteins) are involved as a modulator or transducer in various transmembrane signaling systems. The beta and gamma chains are required for the GTPase activity, for replacement of GDP by GTP, and for G protein-effector interaction.
Gene Name:
GNG2
Uniprot ID:
P63212
Molecular weight:
7850.0
General function:
Not Available
Specific function:
Subunit of both mTORC1 and mTORC2, which regulates cell growth and survival in response to nutrient and hormonal signals. mTORC1 is activated in response to growth factors or amino acids. Growth factor-stimulated mTORC1 activation involves a AKT1-mediated phosphorylation of TSC1-TSC2, which leads to the activation of the RHEB GTPase that potently activates the protein kinase activity of mTORC1. Amino acid-signaling to mTORC1 requires its relocalization to the lysosomes mediated by the Ragulator complex and the Rag GTPases. Activated mTORC1 up-regulates protein synthesis by phosphorylating key regulators of mRNA translation and ribosome synthesis. mTORC1 phosphorylates EIF4EBP1 and releases it from inhibiting the elongation initiation factor 4E (eiF4E). mTORC1 phosphorylates and activates S6K1 at 'Thr-389', which then promotes protein synthesis by phosphorylating PDCD4 and targeting it for degradation. Within mTORC1, LST8 interacts directly with MTOR and enhances its kinase activity. In nutrient-poor conditions, stabilizes the MTOR-RPTOR interaction and favors RPTOR-mediated inhibition of MTOR activity. mTORC2 is also activated by growth factors, but seems to be nutrient-insensitive. mTORC2 seems to function upstream of Rho GTPases to regulate the actin cytoskeleton, probably by activating one or more Rho-type guanine nucleotide exchange factors. mTORC2 promotes the serum-induced formation of stress-fibers or F-actin. mTORC2 plays a critical role in AKT1 'Ser-473' phosphorylation, which may facilitate the phosphorylation of the activation loop of AKT1 on 'Thr-308' by PDK1 which is a prerequisite for full activation. mTORC2 regulates the phosphorylation of SGK1 at 'Ser-422'. mTORC2 also modulates the phosphorylation of PRKCA on 'Ser-657' (By similarity).
Gene Name:
MLST8
Uniprot ID:
Q17QU5
Molecular weight:
35920.0
General function:
Involved in guanyl nucleotide binding
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q4JM29
Molecular weight:
11661.0
General function:
Involved in signal transducer activity
Specific function:
Guanine nucleotide-binding proteins (G proteins) are involved as a modulator or transducer in various transmembrane signaling systems. The beta and gamma chains are required for the GTPase activity, for replacement of GDP by GTP, and for G protein-effector interaction.
Gene Name:
GNB1
Uniprot ID:
P62871
Molecular weight:
37377.0
General function:
Involved in GTP binding
Specific function:
GTPase that associates with pre-60S ribosomal subunits in the nucleolus and is required for their nuclear export and maturation.
Gene Name:
GNL2
Uniprot ID:
Q1JP69
Molecular weight:
83483.0
General function:
Involved in signal transducer activity
Specific function:
Guanine nucleotide-binding proteins (G proteins) are involved as a modulator or transducer in various transmembrane signaling systems. The beta and gamma chains are required for the GTPase activity, for replacement of GDP by GTP, and for G protein-effector interaction. Plays a role in the regulation of adenylyl cyclase signaling in certain regions of the brain. Plays a role in the formation or stabilzation of a G protein heterotrimer (G(olf) subunit alpha-beta-gamma-7) that is required for adenylyl cyclase activity in the striatum (By similarity).
Gene Name:
GNG7
Uniprot ID:
P30671
Molecular weight:
7552.0
General function:
Not Available
Specific function:
Catalyzes the hydrolytic deamination of guanine, producing xanthine and ammonia.
Gene Name:
GDA
Uniprot ID:
F1MLX9
Molecular weight:
51059.0
Reactions
Guanine + Water → Xanthine + Ammoniadetails