NP-MRD: Showing NP-Card for 1-{2,7-dihydroxy-2-oxo-tetrahydro-4h-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl}-4-hydroxypyrimidin-2-one (NP0243903)

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Record Information

Version

2.0

Created at

2022-09-07 04:33:45 UTC

Updated at

2022-09-07 04:33:45 UTC

NP-MRD ID

NP0243903

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-{2,7-dihydroxy-2-oxo-tetrahydro-4h-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl}-4-hydroxypyrimidin-2-one

Description

1-{2,7-Dihydroxy-2-oxo-hexahydro-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl}-4-hydroxy-1,2-dihydropyrimidin-2-one belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. 1-{2,7-dihydroxy-2-oxo-tetrahydro-4h-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl}-4-hydroxypyrimidin-2-one is found in Pisum sativum. 1-{2,7-Dihydroxy-2-oxo-hexahydro-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl}-4-hydroxy-1,2-dihydropyrimidin-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 33  0  0  0  0  0  0  0  0999 V2000
   -5.6755    0.5737    0.2006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4633    0.2480   -0.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0501   -1.0591    0.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7354   -1.3562   -0.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8598   -0.3873   -0.5373 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4881   -0.6441   -0.8122 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1783    0.4841   -1.1960 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1238    0.8095   -0.2678 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3100    1.5616   -0.8328 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1639    1.8587    0.2081 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6511    0.5030    1.0761 P   0  0  1  0  0  5  0  0  0  0  0  0
    4.5567   -0.3812    0.2328 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4307    0.9720    2.4858 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2540   -0.4084    1.4063 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5953   -0.5668    0.2172 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2554   -1.2614    0.3508 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4716   -2.6261    0.1802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3077    0.8754   -0.5751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5240    1.8460   -0.8531 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5822    1.2059   -0.3297 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7896   -1.8128    0.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4231   -2.4128   -0.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4519   -1.4158   -1.6363 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7653    1.3827    0.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8023    1.0148   -1.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9421    2.5238   -1.2449 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3578    1.2369    2.2385 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2034   -1.0694   -0.5445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2153   -1.0199    1.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4362   -2.8685    0.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9318    2.1940   -0.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14 11  1  0
 11 13  1  1
 11 12  2  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  2 20  1  0
 20 18  1  0
 18 19  2  0
  6 16  1  0
 18  5  1  0
  8 15  1  0
 17 30  1  0
 16 29  1  1
 15 28  1  6
 13 27  1  0
  9 25  1  0
  9 26  1  0
  8 24  1  1
  6 23  1  6
  4 22  1  0
  3 21  1  0
 20 31  1  0
M  END


  Mrv1533004261512412D          

 20 22  0  0  0  0            999 V2000
    0.8838    0.7541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.6345    0.4898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1648   -0.4287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    0.0165    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    0.7310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  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
 18 19  1  0  0  0  0
 13 19  1  0  0  0  0
 19 20  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0243903

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1C2OP(O)(=O)OCC2OC1N1C=CC(=O)NC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H11N2O8P/c12-5-1-2-11(9(14)10-5)8-6(13)7-4(18-8)3-17-20(15,16)19-7/h1-2,4,6-8,13H,3H2,(H,15,16)(H,10,12,14)

> <INCHI_KEY>
NXIHNBWNDCFCGL-UHFFFAOYSA-N

> <FORMULA>
C9H11N2O8P

> <MOLECULAR_WEIGHT>
306.167

> <EXACT_MASS>
306.02530232

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
24.59386570381966

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-{2,7-dihydroxy-2-oxo-hexahydro-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl}-1,2,3,4-tetrahydropyrimidine-2,4-dione

> <ALOGPS_LOGP>
-1.36

> <JCHEM_LOGP>
-1.6422703816666666

> <ALOGPS_LOGS>
-1.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.700943690610597

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8328289428807443

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8084242713870173

> <JCHEM_POLAR_SURFACE_AREA>
134.63

> <JCHEM_REFRACTIVITY>
59.659499999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.08e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-{2,7-dihydroxy-2-oxo-tetrahydro-4H-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl}-3H-pyrimidine-2,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  O   UNK     0       1.650   1.408   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.924   0.237   0.000  0.00  0.00           O+0
HETATM    5  P   UNK     0       6.258  -0.533   0.000  0.00  0.00           P+0
HETATM    6  O   UNK     0       6.784   0.914   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       7.774  -0.800   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       6.258  -2.073   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.126  -2.549   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -0.320  -1.303   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      -1.090  -2.637   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.630  -2.637   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.400  -1.303   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.940  -1.303   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0      -2.630   0.031   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      -1.090   0.031   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.320   1.365   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7    8                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    3   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11    2   13                                                  
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   13   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₉H₁₁N₂O₈P

Average Mass

306.1670 Da

Monoisotopic Mass

306.02530 Da

IUPAC Name

1-{2,7-dihydroxy-2-oxo-hexahydro-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl}-1,2,3,4-tetrahydropyrimidine-2,4-dione

Traditional Name

1-{2,7-dihydroxy-2-oxo-tetrahydro-4H-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl}-3H-pyrimidine-2,4-dione

CAS Registry Number

Not Available

SMILES

OC1C2OP(O)(=O)OCC2OC1N1C=CC(=O)NC1=O

InChI Identifier

InChI=1S/C9H11N2O8P/c12-5-1-2-11(9(14)10-5)8-6(13)7-4(18-8)3-17-20(15,16)19-7/h1-2,4,6-8,13H,3H2,(H,15,16)(H,10,12,14)

InChI Key

NXIHNBWNDCFCGL-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

Species Name	Source	Reference
Pisum sativum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Pentose phosphates

Alternative Parents

Substituents

Pentose phosphate
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
Pyrimidone
Hydropyrimidine
Organic phosphoric acid derivative
Pyrimidine
Heteroaromatic compound
Oxolane
Vinylogous amide
Lactam
Secondary alcohol
Urea
Organoheterocyclic compound
Azacycle
Oxacycle
Alcohol
Hydrocarbon derivative
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic nitrogen compound
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	-1.4	ALOGPS
logP	-1.6	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	1.83	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	134.63 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	59.66 m³·mol⁻¹	ChemAxon
Polarizability	24.59 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

4063570

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-{2,7-dihydroxy-2-oxo-tetrahydro-4h-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl}-4-hydroxypyrimidin-2-one (NP0243903)

MOL for NP0243903 (1-{2,7-dihydroxy-2-oxo-tetrahydro-4h-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl}-4-hydroxypyrimidin-2-one)

3D MOL for NP0243903 (1-{2,7-dihydroxy-2-oxo-tetrahydro-4h-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl}-4-hydroxypyrimidin-2-one)

3D SDF for NP0243903 (1-{2,7-dihydroxy-2-oxo-tetrahydro-4h-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl}-4-hydroxypyrimidin-2-one)

3D-SDF for NP0243903 (1-{2,7-dihydroxy-2-oxo-tetrahydro-4h-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl}-4-hydroxypyrimidin-2-one)

PDB for NP0243903 (1-{2,7-dihydroxy-2-oxo-tetrahydro-4h-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl}-4-hydroxypyrimidin-2-one)

3D PDB for NP0243903 (1-{2,7-dihydroxy-2-oxo-tetrahydro-4h-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl}-4-hydroxypyrimidin-2-one)

SMILES for NP0243903 (1-{2,7-dihydroxy-2-oxo-tetrahydro-4h-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl}-4-hydroxypyrimidin-2-one)

INCHI for NP0243903 (1-{2,7-dihydroxy-2-oxo-tetrahydro-4h-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl}-4-hydroxypyrimidin-2-one)

Structure for NP0243903 (1-{2,7-dihydroxy-2-oxo-tetrahydro-4h-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl}-4-hydroxypyrimidin-2-one)

3D Structure for NP0243903 (1-{2,7-dihydroxy-2-oxo-tetrahydro-4h-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl}-4-hydroxypyrimidin-2-one)