MiMeDB: Showing metabocard for 2'-O-Methylguanosine 5'-monophosphate (MMDBc0057187)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-11-09 19:28:41 UTC

Update Date

2025-10-07 16:09:55 UTC

Metabolite ID

MMDBc0057187

Metabolite Identification

Common Name

2'-O-Methylguanosine 5'-monophosphate

Description

2'-O-Methylguanosine 5'-monophosphate is a ribonucleoside metabolite belonging to the class of modified nucleotides. Its chemical structure features a guanosine base attached to a ribose sugar that has a methyl group at the 2' position, resulting in increased stability and potential roles in RNA processing and function. This modification is often found in various RNA species, including tRNA and rRNA, where it plays a critical role in maintaining structural integrity and enhancing the fidelity of protein synthesis. The presence of 2'-O-methylguanosine 5'-monophosphate in RNA can influence interactions with ribosomal proteins and other RNA-binding factors, thereby affecting translation efficiency and accuracy. Additionally, antibodies have been developed that specifically recognize this ribose methylated nucleotide, highlighting its significance in biochemical assays and research (PMID:6269628 ). The ability to target 2'-O-methylguanosine 5'-monophosphate with specific antibodies underscores its importance in understanding the molecular mechanisms of RNA modifications and their implications in cellular processes (PMID:6269628 ).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05041408592D          

 29 31  0  0  1  0            999 V2000
    1.3240   -2.1030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8505   -3.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1831   -3.2299    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -3.4849    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0865   -2.8174    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -2.1500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -4.2695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9391   -4.3492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7565   -3.1968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7867   -4.5317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9115   -2.8174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6042   -3.3793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1831   -2.4049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2716   -3.8642    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7831   -3.9515    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7471   -4.2326    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4610   -3.5525    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4164   -2.0209    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  1  0  0  0
  6  4  1  0  0  0  0
  7  6  1  0  0  0  0
  8  5  2  0  0  0  0
  9  5  1  0  0  0  0
 10  7  1  0  0  0  0
 12 11  2  0  0  0  0
 13  3  2  0  0  0  0
 13  5  1  0  0  0  0
 14  8  1  0  0  0  0
 14 11  1  0  0  0  0
 15  9  2  0  0  0  0
 15 11  1  0  0  0  0
 16  3  1  0  0  0  0
 16  8  1  0  0  0  0
 10 16  1  1  0  0  0
  6 17  1  6  0  0  0
 18  9  1  0  0  0  0
 22  1  1  0  0  0  0
  7 22  1  6  0  0  0
 23  2  1  0  0  0  0
 24  4  1  0  0  0  0
 24 10  1  0  0  0  0
 25 19  1  0  0  0  0
 25 20  1  0  0  0  0
 25 21  2  0  0  0  0
 25 23  1  0  0  0  0
  4 26  1  6  0  0  0
  6 27  1  1  0  0  0
  7 28  1  1  0  0  0
 10 29  1  6  0  0  0
M  END


  Mrv0541 05041408592D          

 29 31  0  0  1  0            999 V2000
    1.3240   -2.1030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8505   -3.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1831   -3.2299    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -3.4849    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0865   -2.8174    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -2.1500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -4.2695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9391   -4.3492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7565   -3.1968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7867   -4.5317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9115   -2.8174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6042   -3.3793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1831   -2.4049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2716   -3.8642    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7831   -3.9515    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7471   -4.2326    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4610   -3.5525    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4164   -2.0209    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  1  0  0  0
  6  4  1  0  0  0  0
  7  6  1  0  0  0  0
  8  5  2  0  0  0  0
  9  5  1  0  0  0  0
 10  7  1  0  0  0  0
 12 11  2  0  0  0  0
 13  3  2  0  0  0  0
 13  5  1  0  0  0  0
 14  8  1  0  0  0  0
 14 11  1  0  0  0  0
 15  9  2  0  0  0  0
 15 11  1  0  0  0  0
 16  3  1  0  0  0  0
 16  8  1  0  0  0  0
 10 16  1  1  0  0  0
  6 17  1  6  0  0  0
 18  9  1  0  0  0  0
 22  1  1  0  0  0  0
  7 22  1  6  0  0  0
 23  2  1  0  0  0  0
 24  4  1  0  0  0  0
 24 10  1  0  0  0  0
 25 19  1  0  0  0  0
 25 20  1  0  0  0  0
 25 21  2  0  0  0  0
 25 23  1  0  0  0  0
  4 26  1  6  0  0  0
  6 27  1  1  0  0  0
  7 28  1  1  0  0  0
 10 29  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0057187

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@]1(COP(O)(O)=O)O[C@@]([H])(N2C=NC3=C2NC(=N)N=C3O)[C@]([H])(OC)[C@]1([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C11H16N5O8P/c1-22-7-6(17)4(2-23-25(19,20)21)24-10(7)16-3-13-5-8(16)14-11(12)15-9(5)18/h3-4,6-7,10,17H,2H2,1H3,(H2,19,20,21)(H3,12,14,15,18)/t4-,6-,7-,10-/m1/s1

> <INCHI_KEY>
YPMKZCOIEXUDSS-KQYNXXCUSA-N

> <FORMULA>
C11H16N5O8P

> <MOLECULAR_WEIGHT>
377.2472

> <EXACT_MASS>
377.073649025

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
32.66156268313823

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3R,4R,5R)-3-hydroxy-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)-4-methoxyoxolan-2-yl]methoxy}phosphonic acid

> <ALOGPS_LOGP>
-1.50

> <JCHEM_LOGP>
-1.899069605130592

> <ALOGPS_LOGS>
-2.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.938256426033114

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.2633347515061857

> <JCHEM_PKA_STRONGEST_BASIC>
4.920419014684693

> <JCHEM_POLAR_SURFACE_AREA>
191.73999999999998

> <JCHEM_REFRACTIVITY>
90.8263

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.15e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3R,4R,5R)-3-hydroxy-5-(6-hydroxy-2-imino-3H-purin-9-yl)-4-methoxyoxolan-2-yl]methoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   25  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   26  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1   22                                                            
CONECT    2    4   23                                                       
CONECT    3   13   16                                                       
CONECT    4    2    6   24   26                                             
CONECT    5    8    9   13                                                  
CONECT    6    4    7   17   27                                             
CONECT    7    6   10   22   28                                             
CONECT    8    5   14   16                                                  
CONECT    9    5   15   18                                                  
CONECT   10    7   16   24   29                                             
CONECT   11   12   14   15                                                  
CONECT   12   11                                                            
CONECT   13    3    5                                                       
CONECT   14    8   11                                                       
CONECT   15    9   11                                                       
CONECT   16    3    8   10                                                  
CONECT   17    6                                                            
CONECT   18    9                                                            
CONECT   19   25                                                            
CONECT   20   25                                                            
CONECT   21   25                                                            
CONECT   22    1    7                                                       
CONECT   23    2   25                                                       
CONECT   24    4   10                                                       
CONECT   25   19   20   21   23                                             
CONECT   26    4                                                            
CONECT   27    6                                                            
CONECT   28    7                                                            
CONECT   29   10                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

Synonyms

Value	Source
2-O-mGMP	ChEBI
2'-O-Methylguanosine 5'-monophosphoric acid	Generator

Molecular Formula

C₁₁H₁₆N₅O₈P

Average Mass

377.2472

Monoisotopic Mass

377.073649025

IUPAC Name

{[(2R,3R,4R,5R)-3-hydroxy-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)-4-methoxyoxolan-2-yl]methoxy}phosphonic acid

Traditional Name

[(2R,3R,4R,5R)-3-hydroxy-5-(6-hydroxy-2-imino-3H-purin-9-yl)-4-methoxyoxolan-2-yl]methoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

[H][C@]1(COP(O)(O)=O)O[C@@]([H])(N2C=NC3=C2NC(=N)N=C3O)[C@]([H])(OC)[C@]1([H])O

InChI Identifier

InChI=1S/C11H16N5O8P/c1-22-7-6(17)4(2-23-25(19,20)21)24-10(7)16-3-13-5-8(16)14-11(12)15-9(5)18/h3-4,6-7,10,17H,2H2,1H3,(H2,19,20,21)(H3,12,14,15,18)/t4-,6-,7-,10-/m1/s1

InChI Key

YPMKZCOIEXUDSS-KQYNXXCUSA-N

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine ribonucleotides

Direct Parent

Purine ribonucleoside monophosphates

Alternative Parents

Substituents

Purine ribonucleoside monophosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
6-oxopurine
Hypoxanthine
Monosaccharide phosphate
Pentose monosaccharide
Imidazopyrimidine
Purine
Monoalkyl phosphate
Aminopyrimidine
Pyrimidone
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Alkyl phosphate
Phosphoric acid ester
Pyrimidine
Imidazole
Azole
Vinylogous amide
Heteroaromatic compound
Tetrahydrofuran
Secondary alcohol
Azacycle
Organoheterocyclic compound
Dialkyl ether
Oxacycle
Ether
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organic nitrogen compound
Amine
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic oxide
Primary amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

guanosine 5'-phosphate (CHEBI:44638 )

Functional Ontology

Not Available

Physical Properties

State

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	2.15 g/L	ALOGPS
logP	-1.5	ALOGPS
logP	-1.9	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	1.26	ChemAxon
pKa (Strongest Basic)	4.92	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	191.74 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	90.83 m³·mol⁻¹	ChemAxon
Polarizability	32.66 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

168161

PDB ID

OMG

ChEBI ID

44638

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for 2'-O-Methylguanosine 5'-monophosphate (MMDBc0057187)

MOL for #<Metabolite:0x00007f8de4096630>

3D MOL for #<Metabolite:0x00007f8de4096630>

3D SDF for #<Metabolite:0x00007f8de4096630>

3D-SDF for #<Metabolite:0x00007f8de4096630>

PDB for #<Metabolite:0x00007f8de4096630>

3D PDB for #<Metabolite:0x00007f8de4096630>

SMILES for #<Metabolite:0x00007f8de4096630>

INCHI for #<Metabolite:0x00007f8de4096630>

Structure for #<Metabolite:0x00007f8de4096630>

3D Structure for #<Metabolite:0x00007f8de4096630>