Metabolite Card

Formula: C10H14N5O8P (363.058)
SMILES: NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]2O)C(=O)N1

Synonyms [en]

GMP; guanosine monophosphate; guanylic acid; Guanosine 5'-phosphate; guanosine-5'-monophosphate; Guanosine 5'-monophosphate

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

GMP. 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000011798). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

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 ribonucleoside monophosphate. Guanosine monophosphate is commercially produced by microbial fermentation. Guanosine monophosphate, also known as guanylic acid or 5'-GMP, belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached. A guanine nucleotide containing one phosphate group esterified to the sugar moiety and found widely in nature. Guanosine monophosphate exists in all living species, ranging from bacteria to humans. Within humans, guanosine monophosphate participates in a number of enzymatic reactions. In particular, guanosine triphosphate and guanosine monophosphate can be biosynthesized from diguanosine tetraphosphate through its interaction with the enzyme bis(5'-nucleosyl)-tetraphosphatase [asymmetrical]. In addition, guanosine monophosphate can be biosynthesized from guanosine diphosphate; which is mediated by the enzyme ectonucleoside triphosphate diphosphohydrolase 5. In humans, guanosine monophosphate is involved in the metabolic disorder called the lesch-nyhan syndrome (lns) pathway. Outside of the human body, guanosine monophosphate has been detected, but not quantified in several different foods, such as common cabbages, tea, winter squash, spearmints, and sugar apples.

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 128952-18-1
  • CAS Registry Number: 1333479
  • CAS Registry Number: 29593-02-0
  • CAS Registry Number: 5550-12-9
  • CAS Registry Number: 85-32-5
  • PubChem: 135398631
  • PubChem: 6804
  • ChEBI: ChEBI:17345
  • HMDB: HMDB0001397
  • KEGG: C00144
  • BioCyc: GMP
  • NCBI MeSH: Guanosine Monophosphate
  • Wikipedia: Guanosine_monophosphate
  • DrugBank: DB01972
  • RefMet: RM0033601
  • MoNA: BAF_UVA_POS000908
  • MoNA: BAF_UVA_POS000909
  • MoNA: BAF_UVA_POS000910
  • MoNA: BML81325
  • MoNA: BML81326
  • MoNA: CCMSLIB00000578007
  • MoNA: CCMSLIB00000578252
  • MoNA: CCMSLIB00005464489
  • MoNA: CCMSLIB00005464596
  • MoNA: CCMSLIB00005720448
  • MoNA: EMBL_MCF_2_0_HRMS_Library000030
  • MoNA: EMBL_MCF_2_0_HRMS_Library000260
  • MoNA: FiehnHILIC001240
  • MoNA: FiehnLib000652
  • MoNA: HMDB0001397_c_ms_2237
  • MoNA: HMDB0001397_ms_ms_1553
  • MoNA: HMDB0001397_ms_ms_1554
  • MoNA: HMDB0001397_ms_ms_1555
  • MoNA: MoNA024043
  • MoNA: MoNA034153
  • MoNA: MoNA034154
  • MoNA: MoNA034159
  • MoNA: MoNA036112
  • MoNA: MoNA036116
  • MoNA: MoNA036117
  • MoNA: MoNA037911
  • MoNA: MoNA038585
  • MoNA: PR100144
  • MoNA: PR100145
  • MoNA: PR100319
  • MoNA: PR100567
  • MoNA: PR100754
  • MoNA: PS024601
  • MoNA: PS024602
  • MoNA: PS024603
  • MoNA: PS024604
  • MoNA: PS024605
  • MoNA: PS024606
  • MoNA: PS024607
  • MoNA: PS024608
  • MoNA: PS024610
  • MoNA: PS024611
  • MoNA: PS024612
  • MoNA: PS071401
  • MoNA: PS071402
  • MoNA: PS071403
  • MoNA: PS071404
  • MoNA: PS071405
  • MoNA: PS071406
  • MoNA: PS071407
  • MoNA: PS071408
  • MoNA: PS071409
  • MoNA: PS071410
  • MoNA: PS071411
  • MoNA: PS071412
  • MoNA: PT107140
  • MoNA: PT207140
  • Metlin: METLIN_98
  • Coconut NaturalProduct: CNP0107450.1
  • Coconut NaturalProduct: CNP0483992.1
  • Coconut NaturalProduct: CNP0554285.1
  • Coconut NaturalProduct: CNP0554285.7

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R00328 3.6.1.5 GDP phosphohydrolase
KEGG:R00332 2.7.4.8 ATP:GMP phosphotransferase
KEGG:R00426 3.6.1.9 GTP diphosphohydrolase (diphosphate-forming);
KEGG:R00881 3.6.1.21 GDP-mannose mannophosphohydrolase
KEGG:R01134 1.7.1.7 inosine-5'-phosphate:NADP+ oxidoreductase (aminating);
KEGG:R01227 3.1.3.5 guanosine 5'-monophosphate phosphohydrolase
KEGG:R01228 2.7.1.73 ATP:guanosine 5'-phosphotransferase
KEGG:R01229 2.4.2.8 GMP:diphosphate 5-phospho-alpha-D-ribosyltransferase
KEGG:R01230 6.3.5.2 xanthosine-5'-phosphate:ammonia ligase (AMP-forming)
KEGG:R01231 6.3.5.2 xanthosine-5'-phosphate:L-glutamine amido-ligase (AMP-forming)
KEGG:R01232 3.6.1.17 P1,P4-bis(5'-guanosyl)-tetraphosphate guanylylhydrolase
KEGG:R01233 3.6.1.- GDPglucose sugarphosphohydrolase
KEGG:R01234 3.1.4.17 guanosine 3',5'-cyclic phosphate 5'-nucleotidohydrolase
KEGG:R03924 2.7.8.9 GDPmannose:phosphomannan mannosephosphotransferase
KEGG:R05223 2.7.8.26 C00194 + C00144<=>C06510 + C05775
KEGG:R09398 2.7.8.28 (2S)-lactyl-2-diphospho-5'-guanosine:7,8-didemethyl-8-hydroxy-5-deazariboflavin 2-phospho-L-lactate transferase
KEGG:R10537 6.5.1.5 RNA-3'-phosphate:RNA ligase (cyclizing, GMP-forming)
KEGG:R10823 6.5.1.7 (deoxyribonucleotide)n:5'-phospho-(deoxyribonucleotide)m ligase (GTP)
KEGG:R11174 2.7.8.26 adenosylcobinamide-GDP:alpha-ribazole adenosylcobinamide-phosphotransferase
KEGG:R12648 2.7.8.28 enolpyruvoyl-2-diphospho-5'-guanosine:7,8-didemethyl-8-hydroxy-5-deazariboflavin 2-phosphoenolpyruvate transferase
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Organism Source

Taxonomy Source

  1. Escherichia coli [ncbi taxid: 562]
  2. FOOD SAKE [ncbi taxid: ]

Pathway Synthetic

pathway id name
PathBank:SMP0000927 Purine Nucleotides De Novo Biosynthesis
PathBank:SMP0002047 Purine Nucleotides De Novo Biosynthesis 2
PathBank:SMP0002086 Guanine and Guanosine Salvage
PathBank:SMP0120666 4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase Deficiency
PathBank:SMP0120670 Adenylosuccinate Lyase Deficiency
PathBank:SMP0120714 Homocarnosinosis
PathBank:SMP0120850 Succinic Semialdehyde Dehydrogenase Deficiency
PathBank:SMP0120448 Adenosine Deaminase Deficiency
PathBank:SMP0120452 AICA-Ribosiduria
PathBank:SMP0120496 Hyperinsulinism-Hyperammonemia Syndrome
PathBank:SMP0120508 Lesch-Nyhan Syndrome (LNS)
PathBank:SMP0120532 Molybdenum Cofactor Deficiency
PathBank:SMP0120536 Purine Nucleoside Phosphorylase Deficiency
PathBank:SMP0120577 Xanthinuria Type I
PathBank:SMP0120601 Mitochondrial DNA Depletion Syndrome
PathBank:SMP0000339 Hyperinsulinism-Hyperammonemia Syndrome
PathBank:SMP0000167 Adenylosuccinate Lyase Deficiency
PathBank:SMP0000220 Xanthine Dehydrogenase Deficiency (Xanthinuria)
PathBank:SMP0000512 Xanthinuria Type I
PathBank:SMP0000536 Mitochondrial DNA Depletion Syndrome-3
View All Pathways