Showing Compound Guanine (FDB004222)

Record Information

Version

1.0

Creation date

2010-04-08 22:06:08 UTC

Update date

2019-11-27 17:10:31 UTC

Primary ID

FDB004222

Secondary Accession Numbers

FDB006726

Chemical Information

FooDB Name

Guanine

Description

Occurs widely in animals and plants. Component of nucleic acids (CCD) Guanine (G) is one of the four main nucleobases found in the nucleic acids DNA and RNA, the others being adenine, cytosine, and thymine (uracil in RNA). In DNA, guanine is paired with cytosine. With the formula C5H5N5O, guanine is a derivative of purine, consisting of a fused pyrimidine-imidazole ring system with conjugated double bonds. Being unsaturated, the bicyclic molecule is planar. The guanine nucleoside is called guanosine.

CAS Number

73-40-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	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
2-Amino-1,7-dihydro-6H-Purin-6-one	biospider
2-amino-6-Oxopurine	ChEBI
2-Amino-9H-purin-6-ol	biospider
2-Amino-Hypoxanthine	biospider
2(1H)-pyrimidinone, 4-amino-	biospider
6H-Purin-6-one, 2-amino-1,7-dihydro- (9CI)	biospider
6H-Purin-6-one, 2-amino-1,9-dihydro-	biospider
6H-purin-6-one, 2-amino-3,7-dihydro-	biospider
Hypoxanthine, 2-amino-	biospider

Predicted Properties

Property	Value	Source
Water Solubility	2.31 g/L	ALOGPS
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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C5H5N5O

IUPAC name

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

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

Isomeric SMILES

NC1=NC(=O)C2=C(N1)N=CN2

Average Molecular Weight

151.1261

Monoisotopic Molecular Weight

151.049409807

Classification

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

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Cryst.	CCD
Mass Composition	C 39.74%; H 3.33%; N 46.34%; O 10.59%	CCD
Melting Point	Mp 300°	CCD
Boiling Point	Not Available
Experimental Water Solubility	2.08 mg/mL at 37 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	-0.91	HANSCH,C ET AL. (1995)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0udi-1938000000-e15e09f2007f35659bb9	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0udi-3739000000-66a080b08ba9b9f82e20	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0udi-5900000000-0a63148e3a8dc8d026df	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-1938000000-e15e09f2007f35659bb9	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0udi-3739000000-66a080b08ba9b9f82e20	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-2928000000-073bf70794fe99ce737f	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000t-2790000000-77e6b5b71c9ff6ad2b23	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ff0-5900000000-f103c75addeafe7ac6f0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0udi-0901000000-2864e73c83444d566e9a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0a4i-2900000000-4229d3d01623054b4ceb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-d5ae84fefadd84f988b4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-7d48b2e8db6967e98407	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0uxr-0900000000-67a7784963ec75cecaa0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-9000000000-4569516f23d8a712b434	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-d928cac1226f19b8edc3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0udi-0900000000-34059351f2cbd94a8acc	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0udj-0903100000-deb9c022884d7c98782e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0900000000-45d9db80ce4657ef1773	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-1900000000-86b7ee5755cbb8236f5b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0udi-0900000000-ba534850b64f39d81fa0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0udi-0900000000-422f992621ab9626d1b2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0f89-0900000000-64e388178db73f06cb20	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0udi-0900000000-f0a95c55947ca990359c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-001i-0900000000-45d9db80ce4657ef1773	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0udi-0900000000-ba534850b64f39d81fa0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0f89-0900000000-64e388178db73f06cb20	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-0udi-0900000000-c2e1c1e8841cc741dac1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-e74c005384d71f4787e5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0900000000-de4a4c4479ea93d742b5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a5i-9800000000-da506476184e5c2313a4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-03d17084c3cb072c0237	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-2900000000-c372e3ba919cba4f561f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9200000000-8ac435f998deda6437e1	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-0udi-8900000000-699c510cfaf838ab1922	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	View in JSpectraViewer

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

16235

Phenol-Explorer ID

Not Available

DrugBank ID

DB02377

HMDB ID

HMDB00132

CRC / DFC (Dictionary of Food Compounds) ID

HHS79-J:HHS79-J

EAFUS ID

Not Available

Dr. Duke ID

GUANINE

BIGG ID

34363

KNApSAcK ID

Not Available

HET ID

GUN

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Guanine

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
essential			DUKE

Enzymes

Name	Gene Name	UniProt ID
Purine nucleoside phosphorylase	PNP	P00491
Adenine phosphoribosyltransferase	APRT	P07741
Guanine nucleotide-binding protein G(s) subunit alpha isoforms short	GNAS	P63092
Guanine nucleotide-binding protein G(q) subunit alpha	GNAQ	P50148
Queuine tRNA-ribosyltransferase subunit QTRTD1	QTRTD1	Q9H974

Pathways

Name	SMPDB Link	KEGG Link
Purine Metabolism	SMP00050	map00230

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Showing Compound Guanine (FDB004222)

Structure for FDB004222 (Guanine)