guanosine 5'-monophosphate (CHEBI:17345)

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CHEBI:17345 - guanosine 5'-monophosphate

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ChEBI Name	guanosine 5'-monophosphate

ChEBI ID	CHEBI:17345

Definition	A purine ribonucleoside 5'-monophosphate having guanine as the nucleobase.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:40119, CHEBI:42979, CHEBI:42831, CHEBI:42615, CHEBI:42887, CHEBI:42892, CHEBI:42647, CHEBI:47450, CHEBI:5228, CHEBI:13341, CHEBI:14381, CHEBI:24449, CHEBI:24450, CHEBI:29058

Supplier Information	ChemicalBook:CB6271952, eMolecules:29480205, eMolecules:5747772, ZINC000002159505

Download	Molfile XML SDF

more structures >>

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-4.2884 3.4337 1.9514 P 0 0 2 0 0 0 0 0 0 0 0 0

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1.1818 0.3047 -0.1155 N 0 0 0 0 0 0 0 0 0 0 0 0

1.6778 1.0312 0.9272 C 0 0 0 0 0 0 0 0 0 0 0 0

2.9786 1.0034 0.9051 N 0 0 0 0 0 0 0 0 0 0 0 0

3.3931 0.2605 -0.1497 C 0 0 0 0 0 0 0 0 0 0 0 0

4.6614 -0.1075 -0.6573 C 0 0 0 0 0 0 0 0 0 0 0 0

5.6850 0.2670 -0.1120 O 0 0 0 0 0 0 0 0 0 0 0 0

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1.0802 1.5515 1.6622 H 0 0 0 0 0 0 0 0 0 0 0 0

5.5678 -1.1524 -2.1268 H 0 0 0 0 0 0 0 0 0 0 0 0

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reading 38 atoms

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38 atoms created

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Wikipedia	License
Guanosine monophosphate (GMP), also known as 5′-guanidylic acid or guanylic acid (conjugate base guanylate), is a nucleotide that is used as a monomer in RNA. It is an ester of phosphoric acid with the nucleoside guanosine. GMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase guanine; hence it is a ribonucleotide monophosphate. Guanosine monophosphate is commercially produced by microbial fermentation. As an acyl substituent, it takes the form of the prefix guanylyl-.
Read full article at Wikipedia

Formula

C10H14N5O8P

Net Charge

Average Mass

363.22082

Monoisotopic Mass

363.05800

InChI

InChI=1S/C10H14N5O8P/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(23-9)1-22-24(19,20)21/h2-3,5-6,9,16-17H,1H2,(H2,19,20,21)(H3,11,13,14,18)/t3-,5-,6-,9-/m1/s1

InChIKey

RQFCJASXJCIDSX-UUOKFMHZSA-N

SMILES

Nc1nc2n(cnc2c(=O)[nH]1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed

Roles Classification
Biological Role(s):	Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.

Application(s):	biomarker A substance used as an indicator of a biological state.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	guanosine 5'-monophosphate (CHEBI:17345) has role Escherichia coli metabolite (CHEBI:76971) guanosine 5'-monophosphate (CHEBI:17345) has role biomarker (CHEBI:59163) guanosine 5'-monophosphate (CHEBI:17345) has role metabolite (CHEBI:25212) guanosine 5'-monophosphate (CHEBI:17345) has role mouse metabolite (CHEBI:75771) guanosine 5'-monophosphate (CHEBI:17345) is a guanosine 5'-phosphate (CHEBI:37121) guanosine 5'-monophosphate (CHEBI:17345) is a purine ribonucleoside 5'-monophosphate (CHEBI:37021) guanosine 5'-monophosphate (CHEBI:17345) is conjugate acid of guanosine 5'-monophosphate(2−) (CHEBI:58115)

Incoming	β-hydroxywybutosine 5'-monophosphate (CHEBI:73622) has functional parent guanosine 5'-monophosphate (CHEBI:17345) (R)-lipoyl-GMP (CHEBI:86459) has functional parent guanosine 5'-monophosphate (CHEBI:17345) 2'-O-methylguanosine 5'-monophosphate (CHEBI:44638) has functional parent guanosine 5'-monophosphate (CHEBI:17345) 4-demethylwyosine 5'-monophosphate (CHEBI:74273) has functional parent guanosine 5'-monophosphate (CHEBI:17345) 7-methylguanosine 5'-phosphate(1+) (CHEBI:17825) has functional parent guanosine 5'-monophosphate (CHEBI:17345) 8-oxo-GMP (CHEBI:65135) has functional parent guanosine 5'-monophosphate (CHEBI:17345) N^ε-(5'-guanylyl)-N^α-acetyl-L-lysine methyl ester(1−) (CHEBI:64853) has functional parent guanosine 5'-monophosphate (CHEBI:17345) N^ε-GMP-N^α-acetyl-L-lysine methyl ester (CHEBI:64856) has functional parent guanosine 5'-monophosphate (CHEBI:17345) N¹-methylguanosine 5'-monophosphate (CHEBI:74268) has functional parent guanosine 5'-monophosphate (CHEBI:17345) N²,N²,N⁷-trimethylguanosine 5'-phosphate (CHEBI:74668) has functional parent guanosine 5'-monophosphate (CHEBI:17345) N²,N²-dimethylguanosine 5'-monophosphate (CHEBI:43967) has functional parent guanosine 5'-monophosphate (CHEBI:17345) N²-methylguanosine 5'-monophosphate (CHEBI:74722) has functional parent guanosine 5'-monophosphate (CHEBI:17345) N⁶-(5'-guanylyl)-L-lysine (CHEBI:21869) has functional parent guanosine 5'-monophosphate (CHEBI:17345) N⁷-methylguanosine 5'-phosphate (CHEBI:74720) has functional parent guanosine 5'-monophosphate (CHEBI:17345) coenzyme F₃₉₀-G (CHEBI:62786) has functional parent guanosine 5'-monophosphate (CHEBI:17345) ddhGMP (CHEBI:156338) has functional parent guanosine 5'-monophosphate (CHEBI:17345) wybutosine 5'-monophosphate (CHEBI:74300) has functional parent guanosine 5'-monophosphate (CHEBI:17345) guanosine 5'-monophosphate(2−) (CHEBI:58115) is conjugate base of guanosine 5'-monophosphate (CHEBI:17345) GMP 3'-end residue (CHEBI:53114) is substituent group from guanosine 5'-monophosphate (CHEBI:17345) GMP 5'-end residue (CHEBI:53100) is substituent group from guanosine 5'-monophosphate (CHEBI:17345) guanosine 5'-monophosphate residue (CHEBI:50324) is substituent group from guanosine 5'-monophosphate (CHEBI:17345)

IUPAC Names

5'-guanylic acid

[(2R,3S,4R,5R)-5-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl dihydrogen phosphate

Synonyms	Sources
5'-GMP	ChemIDplus
GMP	KEGG COMPOUND
Guanosine 5'-monophosphate	KEGG COMPOUND
Guanosine 5'-phosphate	KEGG COMPOUND
Guanosine monophosphate	KEGG COMPOUND
guanosine-5'-monophosphate	PDBeChem
Guanylic acid	KEGG COMPOUND
pG	ChEBI

Manual Xrefs	Databases
5GP	PDBeChem
C00019635	KNApSAcK
C00144	KEGG COMPOUND
DB01972	DrugBank
GMP	MetaCyc
Guanosine_monophosphate	Wikipedia
HMDB0001397	HMDB
View more database links

Registry Numbers	Types	Sources
59430	Reaxys Registry Number	Reaxys
85-32-5	CAS Registry Number	ChemIDplus

Citations

Bordbar A, Mo ML, Nakayasu ES, Schrimpe-Rutledge AC, Kim YM, Metz TO, Jones MB, Frank BC, Smith RD, Peterson SN, Hyduke DR, Adkins JN, Palsson BO (2012)
Model-driven multi-omic data analysis elucidates metabolic immunomodulators of macrophage activation.
Molecular systems biology 8, 558 [PubMed:22735334]
[show Abstract]

Yashima Y, Ohgane T (2001)
[Pharmacological profiles of mycophenolate mofetil (CellCept), a new immunosuppressive agent].
Nihon yakurigaku zasshi. Folia pharmacologica Japonica 117, 131-137 [PubMed:11233304]
[show Abstract]

Choi S, Mahalingaiah S, Delaney S, Neale NR, Masood S (1999)
Substitution and Reduction of Platinum(IV) Complexes by a Nucleotide, Guanosine 5'-Monophosphate.
Inorganic chemistry 38, 1800-1805 [PubMed:11670950]
[show Abstract]
A series of Pt(IV) anticancer complexes with different reduction potentials has been investigated for their reactivity toward 5'-guanosine monophosphate (5'-GMP). The Pt(IV) complexes studied were Pt(IV)(trans-d,l)(1,2-(NH(2))(2)C(6)H(10))Cl(4) (tetraplatin, Pt(IV)(dach)Cl(4); dach = diaminocyclohexane), cis,trans,cis-[Pt(IV)((CH(3))(2)CHNH(2))(2)(OH)(2)Cl(2)] (iproplatin, Pt(IV)(ipa)(2)(OH)(2)Cl(2); ipa = isopropylamine), cis,trans,cis-[Pt(IV)(en)(OH)(2)Cl(2)] (Pt(IV)(en)(OH)(2)Cl(2); en = ethylenediamine), Pt(IV)(en)Cl(4), and cis,trans,cis-[Pt(IV)(en)(OCOCH(3))(2)Cl(2)] (Pt(IV)(en)(OCOCH(3))(2)Cl(2)). The reactivity was monitored by the decreased (1)H NMR peak intensity at 8.2 ppm due to H8 of free 5'-GMP and the increased intensity of a new peak around 8.6 ppm due to H8 of 5'-GMP bound to Pt(II). The reactivity followed the order of cathodic reduction potentials of the Pt(IV) complexes: Pt(IV)(dach)Cl(4) (-90 mV) >> Pt(IV)(en)Cl(4) (-160 mV) > Pt(IV)(en)(OCOCH(3))(2)Cl(2) (-546 mV) > Pt(IV)(ipa)(2)(OH)(2)Cl(2) (-730 mV). The most reactive complex, Pt(IV)(dach)Cl(4), showed an additional weak peak at 9.2 ppm due to H8 of the 5'-GMP bound to the Pt(IV) complex, indicating the existence of a Pt(IV) intermediate. (1)H NMR, UV/visible absorption spectra, and high-performance liquid chromatograms suggest that the final product is Pt(II)(dach)(5'-GMP)(ox5'-GMP), where ox5'-GMP is oxidized 5'-GMP. A plausible mechanism is that there is an initial substitution of one Pt(IV)/ligand by a 5'-GMP molecule, followed by a two-electron reduction, and finally a second substitution by another 5'-GMP. In the presence of excess 5'-GMP (at least 20-fold), ox5'-GMP seems to be replaced by 5'-GMP to form Pt(II)(dach)(5'-GMP)(2). UV/visible absorption spectroscopy shows that the formation of the Pt(IV) intermediate by substitution is a very slow process followed by reduction. The reduction is characterized by a relatively fast exponential decay. The addition of a small amount of cis-[Pt(II)(NH(3))(2)Cl(2)] shortened the slow formation time of the intermediate, implicating the occurrence of a Pt(II)-assisted substitution reaction. These reactions may lead to a better understanding of the anticancer activity of Pt(IV) complexes.

Munns TW, Freeman SK (1989)
Antibody-nucleic acid complexes. Oligo(dG)n and -(dT)n specificities associated with anti-DNA antibodies from autoimmune MRL mice.
Biochemistry 28, 10048-10054 [PubMed:2559771]
[show Abstract]

Zouali M, Migliorini P, Stollar DB (1987)
Murine lupus anti-DNA antibodies cross-react with the hapten (4-hydroxy-5-iodo-3-nitrophenyl)acetyl, but immunization-induced anti-DNA antibodies do not.
European journal of immunology 17, 509-513 [PubMed:3569407]
[show Abstract]

Last Modified

05 December 2017

CHEBI:17345 - guanosine 5'-monophosphate

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