NP-MRD: Showing NP-Card for 2-(6-hydroxy-2-imino-3h-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol (NP0144912)

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Record Information

Version

2.0

Created at

2022-09-01 23:59:33 UTC

Updated at

2022-09-01 23:59:33 UTC

NP-MRD ID

NP0144912

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(6-hydroxy-2-imino-3h-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

Description

Guanosine belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. Guanosine is a moderately basic compound (based on its pKa). When guanine is attached by its N9 nitrogen to the C1 carbon of a deoxyribose ring it is known as deoxyguanosine. It is very soluble in acetic acid, slightly soluble in water, insoluble in ethanol, diethyl ether, benzene and chloroform. In humans, guanosine is involved in intracellular signalling through adenosine receptor A2B and adenosine. Outside of the human body, Guanosine is found, on average, in the highest concentration within milk (cow). Guanosine has also been detected, but not quantified in, several different foods, such as wild carrots, pepper (spice), asparagus, wild celeries, and peanuts. This could make guanosine a potential biomarker for the consumption of these foods. Guanosine was also used to make regadenoson. The antiviral drug acyclovir, often used in herpes treatment, and the anti-HIV drug abacavir, are structurally similar to guanosine. Guanosine can be found in pancreas, clover, coffee plant, and pollen of pines. These forms play important roles in various biochemical processes such as synthesis of nucleic acids and proteins, photosynthesis, muscle contraction, and intracellular signal transduction (cGMP). Guanosine is required for an RNA splicing reaction in mRNA, when a "self-splicing" intron removes itself from the mRNA message by cutting at both ends, re-ligating, and leaving just the exons on either side to be translated into protein. Guanosine is a purine nucleoside comprising guanine attached to a ribose (ribofuranose) ring via a β-N9-glycosidic bond. Guanosine is a white, crystalline powder with no odor and mild saline taste. 2-(6-hydroxy-2-imino-3h-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol is found in Eurycoma longifolia, Pachliopta aristolochiae, Peucedanum japonicum, Sauropus androgynus, Sinocrassula indica, Subergorgia suberosa, Ulva pertusa and Zea mays. Guanosine can be phosphorylated to become guanosine monophosphate (GMP), cyclic guanosine monophosphate (cGMP), guanosine diphosphate (GDP), and guanosine triphosphate (GTP).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305221920082D          

 20 22  0  0  0  0            999 V2000
   -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  0  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  0  0  0  0  0  0  0  0  0  0
    0.0865   -2.8174    0.0000 C   0  0  0  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  0  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
   -1.7643   -4.5353    0.0000 O   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
   -1.1831   -2.4049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  5  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  4  2  0  0  0  0
  8  4  1  0  0  0  0
  9  6  1  0  0  0  0
 11 10  2  0  0  0  0
 12  2  2  0  0  0  0
 12  4  1  0  0  0  0
 13  7  1  0  0  0  0
 13 10  1  0  0  0  0
 14  8  2  0  0  0  0
 14 10  1  0  0  0  0
 15  2  1  0  0  0  0
 15  7  1  0  0  0  0
 15  9  1  0  0  0  0
 16  1  1  0  0  0  0
 17  5  1  0  0  0  0
 18  6  1  0  0  0  0
 19  8  1  0  0  0  0
 20  3  1  0  0  0  0
 20  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0144912

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(C(O)C1O)N1C=NC2=C1NC(=N)N=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C10H13N5O5/c11-10-13-7-4(8(19)14-10)12-2-15(7)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)

> <INCHI_KEY>
NYHBQMYGNKIUIF-UHFFFAOYSA-N

> <FORMULA>
C10H13N5O5

> <MOLECULAR_WEIGHT>
283.2407

> <EXACT_MASS>
283.091668551

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
25.97151460621979

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

> <ALOGPS_LOGP>
-1.78

> <JCHEM_LOGP>
-2.009869935

> <ALOGPS_LOGS>
-1.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.362468028200354

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.978141634851242

> <JCHEM_PKA_STRONGEST_BASIC>
2.963918293515141

> <JCHEM_POLAR_SURFACE_AREA>
156.21

> <JCHEM_REFRACTIVITY>
75.2022

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.98e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(6-hydroxy-2-imino-3H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  C   UNK     0      -3.454  -6.934   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.208  -6.029   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.744  -6.505   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.161  -5.259   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.744  -4.013   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       5.198  -2.843   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      -0.268  -0.057   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       2.530  -2.843   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       3.864  -0.533   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0      -0.268  -2.549   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0      -3.293  -8.466   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -0.268  -7.970   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.701  -5.259   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.530   1.777   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.208  -4.489   0.000  0.00  0.00           O+0
CONECT    1    3   16                                                       
CONECT    2   12   15                                                       
CONECT    3    1    5   20                                                  
CONECT    4    7    8   12                                                  
CONECT    5    3    6   17                                                  
CONECT    6    5    9   18                                                  
CONECT    7    4   13   15                                                  
CONECT    8    4   14   19                                                  
CONECT    9    6   15   20                                                  
CONECT   10   11   13   14                                                  
CONECT   11   10                                                            
CONECT   12    2    4                                                       
CONECT   13    7   10                                                       
CONECT   14    8   10                                                       
CONECT   15    2    7    9                                                  
CONECT   16    1                                                            
CONECT   17    5                                                            
CONECT   18    6                                                            
CONECT   19    8                                                            
CONECT   20    3    9                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₁₃N₅O₅

Average Mass

283.2407 Da

Monoisotopic Mass

283.09167 Da

IUPAC Name

2-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

Traditional Name

2-(6-hydroxy-2-imino-3H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

CAS Registry Number

Not Available

SMILES

OCC1OC(C(O)C1O)N1C=NC2=C1NC(=N)N=C2O

InChI Identifier

InChI=1S/C10H13N5O5/c11-10-13-7-4(8(19)14-10)12-2-15(7)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)

InChI Key

NYHBQMYGNKIUIF-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, DMSO-d6, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Eurycoma longifolia	LOTUS Database	35616633
Pachliopta aristolochiae	LOTUS Database	35616633
Peucedanum japonicum	LOTUS Database	35616633
Sauropus androgynus	LOTUS Database	35616633
Sinocrassula indica	LOTUS Database	35616633
Subergorgia suberosa	LOTUS Database	35616633
Ulva pertusa	LOTUS Database	35616633
Zea mays	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleosides

Sub Class

Not Available

Direct Parent

Purine nucleosides

Alternative Parents

Substituents

Purine nucleoside
Glycosyl compound
N-glycosyl compound
6-oxopurine
Hypoxanthine
Pentose monosaccharide
Purinone
Imidazopyrimidine
Purine
Aminopyrimidine
Pyrimidone
Monosaccharide
N-substituted imidazole
Pyrimidine
Azole
Imidazole
Heteroaromatic compound
Vinylogous amide
Tetrahydrofuran
Secondary alcohol
Organoheterocyclic compound
Azacycle
Oxacycle
Organooxygen compound
Organonitrogen compound
Amine
Alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Primary alcohol
Primary amine
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a purine ribonucleoside (GUANOSINE )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-1.8	ALOGPS
logP	-2	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	5.98	ChemAxon
pKa (Strongest Basic)	2.96	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.21 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	75.2 m³·mol⁻¹	ChemAxon
Polarizability	25.97 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB003632

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Guanosine

METLIN ID

Not Available

PubChem Compound

765

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(6-hydroxy-2-imino-3h-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol (NP0144912)

MOL for NP0144912 (2-(6-hydroxy-2-imino-3h-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol)

3D MOL for NP0144912 (2-(6-hydroxy-2-imino-3h-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol)

3D SDF for NP0144912 (2-(6-hydroxy-2-imino-3h-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol)

3D-SDF for NP0144912 (2-(6-hydroxy-2-imino-3h-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol)

PDB for NP0144912 (2-(6-hydroxy-2-imino-3h-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol)

3D PDB for NP0144912 (2-(6-hydroxy-2-imino-3h-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol)

SMILES for NP0144912 (2-(6-hydroxy-2-imino-3h-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol)

INCHI for NP0144912 (2-(6-hydroxy-2-imino-3h-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol)

Structure for NP0144912 (2-(6-hydroxy-2-imino-3h-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol)

3D Structure for NP0144912 (2-(6-hydroxy-2-imino-3h-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol)