NP-MRD: Showing NP-Card for [3-hydroxy-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxyphosphonic acid (NP0225448)

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Record Information

Version

2.0

Created at

2022-09-06 04:10:22 UTC

Updated at

2022-09-06 04:10:22 UTC

NP-MRD ID

NP0225448

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[3-hydroxy-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxyphosphonic acid

Description

{[3-Hydroxy-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl]methoxy}phosphonic acid belongs to the class of organic compounds known as purine 2'-deoxyribonucleoside monophosphates. These are purine nucleotides with monophosphate group linked to the ribose moiety lacking a hydroxyl group at position 2. {[3-Hydroxy-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl]methoxy}phosphonic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004171503332D          

 23 25  0  0  0  0            999 V2000
    2.7845    0.6979    0.0000 N   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
    1.3556    0.6979    0.0000 N   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
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0865   -0.5966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -1.2640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -2.0486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1831   -1.0091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8505   -1.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6042   -1.1584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2716   -1.6433    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9391   -2.1283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7565   -0.9759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7867   -2.3108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1831   -0.1841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 13 20  1  0  0  0  0
  9 20  1  0  0  0  0
  5 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  2 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0225448

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=NC2=C(N=CN2C2CC(O)C(COP(O)(O)=O)O2)C(=O)N1

> <INCHI_IDENTIFIER>
InChI=1S/C10H14N5O7P/c11-10-13-8-7(9(17)14-10)12-3-15(8)6-1-4(16)5(22-6)2-21-23(18,19)20/h3-6,16H,1-2H2,(H2,18,19,20)(H3,11,13,14,17)

> <INCHI_KEY>
LTFMZDNNPPEQNG-UHFFFAOYSA-N

> <FORMULA>
C10H14N5O7P

> <MOLECULAR_WEIGHT>
347.224

> <EXACT_MASS>
347.063084809

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
30.29547151821862

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid

> <ALOGPS_LOGP>
-1.87

> <JCHEM_LOGP>
-2.227015605347786

> <ALOGPS_LOGS>
-2.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.257726959302706

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.3002153571496406

> <JCHEM_PKA_STRONGEST_BASIC>
0.39462957678006727

> <JCHEM_POLAR_SURFACE_AREA>
181.51999999999998

> <JCHEM_REFRACTIVITY>
73.98329999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.70e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  N   UNK     0       5.198   1.303   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       2.530   1.303   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -0.268   4.089   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -0.268   1.597   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -0.744   0.132   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.161  -1.114   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.744  -2.359   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.268  -3.824   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.208  -1.884   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.454  -2.789   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.861  -2.162   0.000  0.00  0.00           O+0
HETATM   16  P   UNK     0      -6.107  -3.068   0.000  0.00  0.00           P+0
HETATM   17  O   UNK     0      -7.353  -3.973   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -7.012  -1.822   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -5.202  -4.313   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.208  -0.344   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.530   5.923   0.000  0.00  0.00           O+0
HETATM   23  N   UNK     0       3.864   3.613   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6   21                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    4    9                                                  
CONECT    9    8   10   20                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16                                                            
CONECT   20   13    9                                                       
CONECT   21    5   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21    2                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
{[3-hydroxy-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl]methoxy}phosphonate	Generator

Chemical Formula

C₁₀H₁₄N₅O₇P

Average Mass

347.2240 Da

Monoisotopic Mass

347.06308 Da

IUPAC Name

{[5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid

Traditional Name

[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

NC1=NC2=C(N=CN2C2CC(O)C(COP(O)(O)=O)O2)C(=O)N1

InChI Identifier

InChI=1S/C10H14N5O7P/c11-10-13-8-7(9(17)14-10)12-3-15(8)6-1-4(16)5(22-6)2-21-23(18,19)20/h3-6,16H,1-2H2,(H2,18,19,20)(H3,11,13,14,17)

InChI Key

LTFMZDNNPPEQNG-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine 2'-deoxyribonucleoside monophosphates. These are purine nucleotides with monophosphate group linked to the ribose moiety lacking a hydroxyl group at position 2.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine deoxyribonucleotides

Direct Parent

Purine 2'-deoxyribonucleoside monophosphates

Alternative Parents

Substituents

Purine 2'-deoxyribonucleoside monophosphate
6-oxopurine
Hypoxanthine
Imidazopyrimidine
Purine
Aminopyrimidine
Monoalkyl phosphate
Pyrimidone
N-substituted imidazole
Organic phosphoric acid derivative
Phosphoric acid ester
Pyrimidine
Alkyl phosphate
Heteroaromatic compound
Azole
Imidazole
Vinylogous amide
Tetrahydrofuran
Secondary alcohol
Organoheterocyclic compound
Azacycle
Oxacycle
Primary amine
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Amine
Organic oxygen compound
Hydrocarbon derivative
Organopnictogen compound
Alcohol
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	-1.9	ALOGPS
logP	-2.2	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	1.3	ChemAxon
pKa (Strongest Basic)	0.39	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	181.52 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	73.98 m³·mol⁻¹	ChemAxon
Polarizability	30.3 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

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

135402021

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [3-hydroxy-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxyphosphonic acid (NP0225448)

MOL for NP0225448 ([3-hydroxy-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxyphosphonic acid)

3D MOL for NP0225448 ([3-hydroxy-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxyphosphonic acid)

3D SDF for NP0225448 ([3-hydroxy-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxyphosphonic acid)

3D-SDF for NP0225448 ([3-hydroxy-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxyphosphonic acid)

PDB for NP0225448 ([3-hydroxy-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxyphosphonic acid)

3D PDB for NP0225448 ([3-hydroxy-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxyphosphonic acid)

SMILES for NP0225448 ([3-hydroxy-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxyphosphonic acid)

INCHI for NP0225448 ([3-hydroxy-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxyphosphonic acid)

Structure for NP0225448 ([3-hydroxy-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxyphosphonic acid)

3D Structure for NP0225448 ([3-hydroxy-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxyphosphonic acid)