Cannabis Compound Database: Showing Compound Card for Guanine (CDB004807)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (9) Show 15 proteins XML

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Record Information

Version

1.0

Created at

2020-04-17 18:38:47 UTC

Updated at

2020-12-07 19:10:59 UTC

CannabisDB ID

CDB004807

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Guanine

Description

Guanine, 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 is a moderately basic compound (based on its pKa). Guanine exists in all living species, ranging from bacteria to humans. Within humans, guanine participates in a number of enzymatic reactions. In particular, guanine and phosphoribosyl pyrophosphate can be biosynthesized from guanosine monophosphate through its interaction with the enzyme adenine phosphoribosyltransferase. In addition, guanine and ribose 1-phosphate can be biosynthesized from guanosine; which is catalyzed by the enzyme purine nucleoside phosphorylase. In humans, guanine is involved in the metabolic disorder called the gout or kelley-seegmiller syndrome pathway. Outside of the human body, Guanine is found, on average, in the highest concentration within beers and milk (cow). Guanine has also been detected, but not quantified in, several different foods, such as kombus, black radish, chinese cabbages, dills, and devilfish. This could make guanine a potential biomarker for the consumption of these foods. Guanine, with regard to humans, has been found to be associated with several diseases such as lewy body disease, frontotemporal dementia, colorectal cancer, and alzheimer's disease; guanine has also been linked to the inborn metabolic disorder lesch-nyhan syndrome. A 2-aminopurine carrying a 6-oxo substituent. Guanine is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Amino-6-hydroxypurine	ChEBI
2-Amino-6-oxopurine	ChEBI
G	ChEBI
Gua	ChEBI
2-Amino-1,7-dihydro-6H-purin-6-one	HMDB
2-Amino-1,9-dihydro-6H-purin-6-one	HMDB
2-Amino-1,9-dihydro-purin-6-one	HMDB
2-Amino-3,7-dihydro-6H-purin-6-one	HMDB
2-Amino-6-hydroxy-1H-purine	HMDB
2-Amino-6-purinol	HMDB
2-Amino-hypoxanthine	HMDB
2-Aminohypoxanthine	HMDB
6-Hydroxy-2-aminopurine	HMDB
C.I. natural white 1	HMDB
CI natural white 1	HMDB
Dew pearl	HMDB
Guanin	HMDB
Guanine enol	HMDB
GUN	HMDB
Mearlmaid	HMDB
Mearlmaid aa	HMDB
Natural pearl essence	HMDB
Natural white 1	HMDB
Naturon	HMDB
Pathocidin	HMDB
Pearl essence	HMDB
Stella polaris	HMDB

Chemical Formula

C₅H₅N₅O

Average Molecular Weight

151.13

Monoisotopic Molecular Weight

151.0494

IUPAC Name

2-amino-6,7-dihydro-3H-purin-6-one

Traditional Name

2-aminohypoxanthine

CAS Registry Number

73-40-5

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 Key

UYTPUPDQBNUYGX-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

Purines 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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

oxopurine (CHEBI:16235 )
2-aminopurines (CHEBI:16235 )
purine nucleobase (CHEBI:16235 )
purines (C00242 )
a purine base (GUANINE )
a purine (GUANINE )

Ontology

Physiological effect

Health effect:

Health condition:

Lesch-nyhan syndrome

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	360 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	2.08 mg/mL at 37 °C	Not Available
logP	-0.91	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	-0.92	ALOGPS
logP	-0.59	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	8.95	ChemAxon
pKa (Strongest Basic)	2.22	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.16 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	38.9 m³·mol⁻¹	ChemAxon
Polarizability	13.34 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0udi-8900000000-699c510cfaf838ab1922	2015-03-01	View Spectrum
GC-MS	Guanine, non-derivatized, GC-MS Spectrum	splash10-0udi-1938000000-e15e09f2007f35659bb9	Spectrum
GC-MS	Guanine, 3 TMS, GC-MS Spectrum	splash10-0udi-3739000000-66a080b08ba9b9f82e20	Spectrum
GC-MS	Guanine, non-derivatized, GC-MS Spectrum	splash10-0udi-5900000000-0a63148e3a8dc8d026df	Spectrum
GC-MS	Guanine, non-derivatized, GC-MS Spectrum	splash10-0udi-1938000000-e15e09f2007f35659bb9	Spectrum
GC-MS	Guanine, non-derivatized, GC-MS Spectrum	splash10-0udi-3739000000-66a080b08ba9b9f82e20	Spectrum
GC-MS	Guanine, non-derivatized, GC-MS Spectrum	splash10-0udi-2928000000-073bf70794fe99ce737f	Spectrum
GC-MS	Guanine, non-derivatized, GC-MS Spectrum	splash10-000t-2790000000-77e6b5b71c9ff6ad2b23	Spectrum
Predicted GC-MS	Guanine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0ff0-5900000000-f103c75addeafe7ac6f0	Spectrum
Predicted GC-MS	Guanine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0udi-0901000000-2864e73c83444d566e9a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0a4i-2900000000-4229d3d01623054b4ceb	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-d5ae84fefadd84f988b4	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-7d48b2e8db6967e98407	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0uxr-0900000000-67a7784963ec75cecaa0	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-9000000000-4569516f23d8a712b434	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-d928cac1226f19b8edc3	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0udi-0900000000-34059351f2cbd94a8acc	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0udj-0903100000-deb9c022884d7c98782e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0900000000-45d9db80ce4657ef1773	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-1900000000-86b7ee5755cbb8236f5b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0udi-0900000000-ba534850b64f39d81fa0	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0udi-0900000000-422f992621ab9626d1b2	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0f89-0900000000-64e388178db73f06cb20	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0udi-0900000000-f0a95c55947ca990359c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-001i-0900000000-45d9db80ce4657ef1773	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0udi-0900000000-ba534850b64f39d81fa0	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0f89-0900000000-64e388178db73f06cb20	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-0udi-0900000000-c2e1c1e8841cc741dac1	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-e74c005384d71f4787e5	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0900000000-de4a4c4479ea93d742b5	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a5i-9800000000-da506476184e5c2313a4	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-03d17084c3cb072c0237	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-2900000000-c372e3ba919cba4f561f	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9200000000-8ac435f998deda6437e1	2015-05-27	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 400 MHz, H₂O, experimental)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Purine Metabolism
Adenosine Deaminase Deficiency		Not Available
Adenylosuccinate Lyase Deficiency		Not Available
Gout or Kelley-Seegmiller Syndrome		Not Available
Lesch-Nyhan Syndrome (LNS)		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Adenine phosphoribosyltransferase	APRT	16q24	P07741	details
Hypoxanthine-guanine phosphoribosyltransferase	HPRT1	Xq26.1	P00492	details
Guanine deaminase	GDA	9q21.13	Q9Y2T3	details
Queuine tRNA-ribosyltransferase	QTRT1	19p13.3	Q9BXR0	details
GTP cyclohydrolase 1	GCH1	14q22.1-q22.2	P30793	details
Guanine nucleotide-binding protein G(s) subunit alpha isoforms short	GNAS	20q13.3	P63092	details
Guanine nucleotide-binding protein G(q) subunit alpha	GNAQ	9q21	P50148	details
Purine nucleoside phosphorylase	PNP	14q13.1	P00491	details
Queuine tRNA-ribosyltransferase subunit QTRTD1	QTRTD1	3q13.31	Q9H974	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Guanine deaminase	GDA	9q21.13	Q9Y2T3	details
Queuine tRNA-ribosyltransferase	QTRT1	19p13.3	Q9BXR0	details
Queuine tRNA-ribosyltransferase subunit QTRTD1	QTRTD1	3q13.31	Q9H974	details

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Guanine nucleotide-binding protein G(s) subunit alpha isoforms short	GNAS	20q13.3	P63092	details
Guanine nucleotide-binding protein G(q) subunit alpha	GNAQ	9q21	P50148	details
Guanine nucleotide-binding protein G(i) subunit alpha-1	GNAI1	7q21	P63096	details

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000132

DrugBank ID

DB02377

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

16235

References

General References

Not Available

Only showing the first 10 proteins. There are 15 proteins in total.

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Enzymes

Enzyme Details

1. Adenine phosphoribosyltransferase

General function:: Involved in adenine phosphoribosyltransferase activity
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
Molecular weight:: 19607.535

Enzyme Details

2. Hypoxanthine-guanine phosphoribosyltransferase

General function:: Involved in hypoxanthine phosphoribosyltransferase activity
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.
Gene Name:: HPRT1
Uniprot ID:: P00492
Molecular weight:: 24579.155

Enzyme Details

3. Guanine deaminase

General function:: Involved in hydrolase activity
Specific function:: Catalyzes the hydrolytic deamination of guanine, producing xanthine and ammonia (By similarity).
Gene Name:: GDA
Uniprot ID:: Q9Y2T3
Molecular weight:: 52836.65

Enzyme Details

4. Queuine tRNA-ribosyltransferase

General function:: Involved in queuine tRNA-ribosyltransferase activity
Specific function:: Interacts with QTRTD1 to form an active queuine tRNA-ribosyltransferase. This enzyme exchanges queuine for the guanine at the wobble position of tRNAs with GU(N) anticodons (tRNA-Asp, -Asn, -His and -Tyr), thereby forming the hypermodified nucleoside queuosine (Q) (7-(((4,5-cis-dihydroxy-2-cyclopenten-1-yl)amino)methyl)-7-deazaguanosine) (By similarity).
Gene Name:: QTRT1
Uniprot ID:: Q9BXR0
Molecular weight:: 44047.3

Enzyme Details

5. GTP cyclohydrolase 1

General function:: Involved in GTP cyclohydrolase I activity
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
Molecular weight:: 27902.855

Enzyme Details

6. Guanine nucleotide-binding protein G(s) subunit alpha isoforms short

General function:: Involved in signal transducer activity
Specific function:: Guanine nucleotide-binding proteins (G proteins) are involved as modulators or transducers in various transmembrane signaling systems. The G(s) protein is involved in hormonal regulation of adenylate cyclase:it activates the cyclase in response to beta-adrenergic stimuli
Gene Name:: GNAS
Uniprot ID:: P63092
Molecular weight:: 45664.2

Enzyme Details

7. Guanine nucleotide-binding protein G(q) subunit alpha

General function:: Involved in signal transducer activity
Specific function:: Guanine nucleotide-binding proteins (G proteins) are involved as modulators or transducers in various transmembrane signaling systems
Gene Name:: GNAQ
Uniprot ID:: P50148
Molecular weight:: 42141.7

Enzyme Details

8. Purine nucleoside phosphorylase

General function:: Involved in 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
Molecular weight:: 32117.69

Enzyme Details

9. Queuine tRNA-ribosyltransferase subunit QTRTD1

General function:: Involved in queuine tRNA-ribosyltransferase activity
Specific function:: Interacts with QTRT1 to form an active queuine tRNA-ribosyltransferase. This enzyme exchanges queuine for the guanine at the wobble position of tRNAs with GU(N) anticodons (tRNA-Asp, -Asn, -His and -Tyr), thereby forming the hypermodified nucleoside queuosine (Q) (7-(((4,5-cis-dihydroxy-2-cyclopenten-1-yl)amino)methyl)-7-deazaguanosine) (By similarity).
Gene Name:: QTRTD1
Uniprot ID:: Q9H974
Molecular weight:: 48203.07

Only showing the first 10 proteins. There are 15 proteins in total.

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Showing Compound Card for Guanine (CDB004807)

Structure for CDB004807 (Guanine)

Enzymes