MiMeDB: Showing metabocard for N1-Methylguanosine 5'-monophosphate (MMDBc0057185)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-11-09 19:27:44 UTC

Update Date

2022-11-09 19:27:44 UTC

Metabolite ID

MMDBc0057185

Metabolite Identification

Common Name

N1-Methylguanosine 5'-monophosphate

Description

N(1)-methylguanosine 5'-monophosphate, also known as 1-methyl 5'-guanylic acid, belongs to the class of organic compounds known as pyrrolopyridines. Pyrrolopyridines are compounds containing a pyrrolopyridine moiety, which consists of a pyrrole ring fused to a pyridine. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Pyridine is a 6-membered ring consisting of five carbon atoms and one nitrogen center. N(1)-methylguanosine 5'-monophosphate is a moderately basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05031420092D          

 29 31  0  0  1  0            999 V2000
    2.7845    0.1271    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
    0.9115   -2.8174    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
   -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  1  1  0  0  0  0
 15  9  1  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
  7 18  1  6  0  0  0
 19  9  2  0  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 20  1  0  0  0  0
 25 21  1  0  0  0  0
 25 22  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 05031420092D          

 29 31  0  0  1  0            999 V2000
    2.7845    0.1271    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
    0.9115   -2.8174    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
   -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  1  1  0  0  0  0
 15  9  1  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
  7 18  1  6  0  0  0
 19  9  2  0  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 20  1  0  0  0  0
 25 21  1  0  0  0  0
 25 22  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>
MMDBc0057185

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@]1(COP(O)(O)=O)O[C@@]([H])(N2C=NC3=C2NC(=N)N(C)C3=O)[C@]([H])(O)[C@]1([H])O

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

> <INCHI_KEY>
RQNAZTAAOUHEIL-KQYNXXCUSA-N

> <FORMULA>
C11H16N5O8P

> <MOLECULAR_WEIGHT>
377.2472

> <EXACT_MASS>
377.073649025

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
32.86940766084818

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-imino-1-methyl-6-oxo-2,3,6,9-tetrahydro-1H-purin-9-yl)oxolan-2-yl]methoxy}phosphonic acid

> <ALOGPS_LOGP>
-1.90

> <JCHEM_LOGP>
-3.0079835749878936

> <ALOGPS_LOGS>
-2.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.250635583024064

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.2539873816425775

> <JCHEM_PKA_STRONGEST_BASIC>
2.6761649175632876

> <JCHEM_POLAR_SURFACE_AREA>
190.45999999999995

> <JCHEM_REFRACTIVITY>
90.45009999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.93e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-imino-1-methyl-6-oxo-3H-purin-9-yl)oxolan-2-yl]methoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-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   15                                                            
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   18   28                                             
CONECT    8    5   14   16                                                  
CONECT    9    5   15   19                                                  
CONECT   10    7   16   24   29                                             
CONECT   11   12   14   15                                                  
CONECT   12   11                                                            
CONECT   13    3    5                                                       
CONECT   14    8   11                                                       
CONECT   15    1    9   11                                                  
CONECT   16    3    8   10                                                  
CONECT   17    6                                                            
CONECT   18    7                                                            
CONECT   19    9                                                            
CONECT   20   25                                                            
CONECT   21   25                                                            
CONECT   22   25                                                            
CONECT   23    2   25                                                       
CONECT   24    4   10                                                       
CONECT   25   20   21   22   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
1-Methyl 5'-guanylic acid	ChEBI
1-Methyl 5'-guanylate	Generator
N(1)-Methylguanosine 5'-monophosphoric acid	Generator
1-Methylguanosine 5'-(dihydrogen phosphoric acid)	Generator

Molecular Formula

C₁₁H₁₆N₅O₈P

Average Mass

377.2472

Monoisotopic Mass

377.073649025

IUPAC Name

{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-imino-1-methyl-6-oxo-2,3,6,9-tetrahydro-1H-purin-9-yl)oxolan-2-yl]methoxy}phosphonic acid

Traditional Name

[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-imino-1-methyl-6-oxo-3H-purin-9-yl)oxolan-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(C)C3=O)[C@]([H])(O)[C@]1([H])O

InChI Identifier

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

InChI Key

RQNAZTAAOUHEIL-KQYNXXCUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolopyridines. Pyrrolopyridines are compounds containing a pyrrolopyridine moiety, which consists of a pyrrole ring fused to a pyridine. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Pyridine is a 6-membered ring consisting of five carbon atoms and one nitrogen center.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolopyridines

Sub Class

Not Available

Direct Parent

Pyrrolopyridines

Alternative Parents

Substituents

Pyrrolopyridine
3-pyridine carboxaldehyde
Aryl-aldehyde
Pyridine
Heteroaromatic compound
Pyrrole
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aldehyde
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	2.93 g/L	ALOGPS
logP	-1.9	ALOGPS
logP	-3	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	1.25	ChemAxon
pKa (Strongest Basic)	2.68	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	190.46 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	90.45 m³·mol⁻¹	ChemAxon
Polarizability	32.87 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	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

Metabolic Reactions

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

Source Type	Activity	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

18596452

PDB ID

Not Available

ChEBI ID

74268

Food Biomarker Ontology

Not Available

References

Synthesis Reference

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 N1-Methylguanosine 5'-monophosphate (MMDBc0057185)

MOL for #<Metabolite:0x00007f3e0cd73150>

3D MOL for #<Metabolite:0x00007f3e0cd73150>

3D SDF for #<Metabolite:0x00007f3e0cd73150>

3D-SDF for #<Metabolite:0x00007f3e0cd73150>

PDB for #<Metabolite:0x00007f3e0cd73150>

3D PDB for #<Metabolite:0x00007f3e0cd73150>

SMILES for #<Metabolite:0x00007f3e0cd73150>

INCHI for #<Metabolite:0x00007f3e0cd73150>

Structure for #<Metabolite:0x00007f3e0cd73150>

3D Structure for #<Metabolite:0x00007f3e0cd73150>