MiMeDB: Showing metabocard for N2,N2-dimethylguanosine 5'-monophosphate (MMDBc0057184)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-11-09 19:27:27 UTC

Update Date

2022-11-09 19:27:27 UTC

Metabolite ID

MMDBc0057184

Metabolite Identification

Common Name

N2,N2-dimethylguanosine 5'-monophosphate

Description

N(2),N(2)-dimethylguanosine 5'-monophosphate, also known as N(2),N(2)-dimethyl-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. N(2),N(2)-dimethylguanosine 5'-monophosphate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05041407182D          

 30 32  0  0  1  0            999 V2000
    3.4990   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -2.3479    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
   -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
    2.7845   -1.5229    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
  5  3  1  1  0  0  0
  7  5  1  0  0  0  0
  8  7  1  0  0  0  0
  9  6  2  0  0  0  0
 10  6  1  0  0  0  0
 11  8  1  0  0  0  0
 13  4  2  0  0  0  0
 13  6  1  0  0  0  0
 14  9  1  0  0  0  0
 14 12  2  0  0  0  0
 15 10  2  0  0  0  0
 15 12  1  0  0  0  0
 16  1  1  0  0  0  0
 16  2  1  0  0  0  0
 16 12  1  0  0  0  0
 17  4  1  0  0  0  0
 17  9  1  0  0  0  0
 11 17  1  1  0  0  0
  7 18  1  6  0  0  0
  8 19  1  6  0  0  0
 20 10  1  0  0  0  0
 24  3  1  0  0  0  0
 25  5  1  0  0  0  0
 25 11  1  0  0  0  0
 26 21  1  0  0  0  0
 26 22  1  0  0  0  0
 26 23  2  0  0  0  0
 26 24  1  0  0  0  0
  5 27  1  6  0  0  0
  7 28  1  1  0  0  0
  8 29  1  1  0  0  0
 11 30  1  6  0  0  0
M  END


  Mrv0541 05041407182D          

 30 32  0  0  1  0            999 V2000
    3.4990   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -2.3479    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
   -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
    2.7845   -1.5229    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
  5  3  1  1  0  0  0
  7  5  1  0  0  0  0
  8  7  1  0  0  0  0
  9  6  2  0  0  0  0
 10  6  1  0  0  0  0
 11  8  1  0  0  0  0
 13  4  2  0  0  0  0
 13  6  1  0  0  0  0
 14  9  1  0  0  0  0
 14 12  2  0  0  0  0
 15 10  2  0  0  0  0
 15 12  1  0  0  0  0
 16  1  1  0  0  0  0
 16  2  1  0  0  0  0
 16 12  1  0  0  0  0
 17  4  1  0  0  0  0
 17  9  1  0  0  0  0
 11 17  1  1  0  0  0
  7 18  1  6  0  0  0
  8 19  1  6  0  0  0
 20 10  1  0  0  0  0
 24  3  1  0  0  0  0
 25  5  1  0  0  0  0
 25 11  1  0  0  0  0
 26 21  1  0  0  0  0
 26 22  1  0  0  0  0
 26 23  2  0  0  0  0
 26 24  1  0  0  0  0
  5 27  1  6  0  0  0
  7 28  1  1  0  0  0
  8 29  1  1  0  0  0
 11 30  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0057184

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@]1(COP(O)(O)=O)O[C@@]([H])(N2C=NC3=C2N=C(N=C3O)N(C)C)[C@]([H])(O)[C@]1([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C12H18N5O8P/c1-16(2)12-14-9-6(10(20)15-12)13-4-17(9)11-8(19)7(18)5(25-11)3-24-26(21,22)23/h4-5,7-8,11,18-19H,3H2,1-2H3,(H,14,15,20)(H2,21,22,23)/t5-,7-,8-,11-/m1/s1

> <INCHI_KEY>
IWJFVRMOIKWYNZ-IOSLPCCCSA-N

> <FORMULA>
C12H18N5O8P

> <MOLECULAR_WEIGHT>
391.2738

> <EXACT_MASS>
391.089299089

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
35.16021173647684

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.44

> <JCHEM_LOGP>
-1.3150396795831023

> <ALOGPS_LOGS>
-2.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.250522715143434

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.3851063489577946

> <JCHEM_PKA_STRONGEST_BASIC>
0.714967056075929

> <JCHEM_POLAR_SURFACE_AREA>
183.51999999999998

> <JCHEM_REFRACTIVITY>
85.7236

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.50e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4R,5R)-5-[2-(dimethylamino)-6-hydroxypurin-9-yl]-3,4-dihydroxyoxolan-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  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+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  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+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  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   26  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+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
HETATM   30  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1   16                                                            
CONECT    2   16                                                            
CONECT    3    5   24                                                       
CONECT    4   13   17                                                       
CONECT    5    3    7   25   27                                             
CONECT    6    9   10   13                                                  
CONECT    7    5    8   18   28                                             
CONECT    8    7   11   19   29                                             
CONECT    9    6   14   17                                                  
CONECT   10    6   15   20                                                  
CONECT   11    8   17   25   30                                             
CONECT   12   14   15   16                                                  
CONECT   13    4    6                                                       
CONECT   14    9   12                                                       
CONECT   15   10   12                                                       
CONECT   16    1    2   12                                                  
CONECT   17    4    9   11                                                  
CONECT   18    7                                                            
CONECT   19    8                                                            
CONECT   20   10                                                            
CONECT   21   26                                                            
CONECT   22   26                                                            
CONECT   23   26                                                            
CONECT   24    3   26                                                       
CONECT   25    5   11                                                       
CONECT   26   21   22   23   24                                             
CONECT   27    5                                                            
CONECT   28    7                                                            
CONECT   29    8                                                            
CONECT   30   11                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

Synonyms

Value	Source
N(2),N(2)-Dimethyl-GMP	ChEBI
N(2),N(2)-Dimethylguanosine 5'-phosphate	ChEBI
N(2),N(2)-Dimethylguanosine 5'-phosphoric acid	Generator
N(2),N(2)-Dimethylguanosine 5'-monophosphoric acid	Generator

Molecular Formula

C₁₂H₁₈N₅O₈P

Average Mass

391.2738

Monoisotopic Mass

391.089299089

IUPAC Name

{[(2R,3S,4R,5R)-5-[2-(dimethylamino)-6-hydroxy-9H-purin-9-yl]-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid

Traditional Name

[(2R,3S,4R,5R)-5-[2-(dimethylamino)-6-hydroxypurin-9-yl]-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

[H][C@]1(COP(O)(O)=O)O[C@@]([H])(N2C=NC3=C2N=C(N=C3O)N(C)C)[C@]([H])(O)[C@]1([H])O

InChI Identifier

InChI=1S/C12H18N5O8P/c1-16(2)12-14-9-6(10(20)15-12)13-4-17(9)11-8(19)7(18)5(25-11)3-24-26(21,22)23/h4-5,7-8,11,18-19H,3H2,1-2H3,(H,14,15,20)(H2,21,22,23)/t5-,7-,8-,11-/m1/s1

InChI Key

IWJFVRMOIKWYNZ-IOSLPCCCSA-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
Dialkylarylamine
Aminopyrimidine
Monoalkyl phosphate
Pyrimidone
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Pyrimidine
Azole
Tetrahydrofuran
Vinylogous amide
Heteroaromatic compound
Imidazole
Secondary alcohol
1,2-diol
Organoheterocyclic compound
Azacycle
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Alcohol
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

purine ribonucleoside 5'-monophosphate (CHEBI:43967 )

Functional Ontology

Not Available

Physical Properties

State

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	3.5 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-1.3	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	1.39	ChemAxon
pKa (Strongest Basic)	0.71	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	183.52 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	85.72 m³·mol⁻¹	ChemAxon
Polarizability	35.16 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

10691837

PDB ID

M2G

ChEBI ID

43967

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 N2,N2-dimethylguanosine 5'-monophosphate (MMDBc0057184)

MOL for #<Metabolite:0x00007f3ddf424db0>

3D MOL for #<Metabolite:0x00007f3ddf424db0>

3D SDF for #<Metabolite:0x00007f3ddf424db0>

3D-SDF for #<Metabolite:0x00007f3ddf424db0>

PDB for #<Metabolite:0x00007f3ddf424db0>

3D PDB for #<Metabolite:0x00007f3ddf424db0>

SMILES for #<Metabolite:0x00007f3ddf424db0>

INCHI for #<Metabolite:0x00007f3ddf424db0>

Structure for #<Metabolite:0x00007f3ddf424db0>

3D Structure for #<Metabolite:0x00007f3ddf424db0>