NP-MRD: Showing NP-Card for 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-2-oxopyrimidin-5-yl formate (NP0183292)

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Record Information

Version

2.0

Created at

2022-09-03 22:10:30 UTC

Updated at

2022-09-03 22:10:30 UTC

NP-MRD ID

NP0183292

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-2-oxopyrimidin-5-yl formate

Description

1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-2-oxo-1,2-dihydropyrimidin-5-yl formate belongs to the class of organic compounds known as pyrimidine nucleosides. Pyrimidine nucleosides are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety. 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-2-oxopyrimidin-5-yl formate is found in Serratia plymuthica. Based on a literature review very few articles have been published on 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-2-oxo-1,2-dihydropyrimidin-5-yl formate.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 33  0  0  0  0  0  0  0  0999 V2000
    3.5917    2.1033    0.3934 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7227    2.0293   -0.8568 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2525    0.8817   -1.4857 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6646   -0.1238   -0.7170 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2925   -0.1136   -0.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7469   -1.0915    0.2715 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6954   -1.0822    0.5309 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3115   -0.8000   -0.6728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4449   -0.0400   -0.3944 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8161    0.6917   -1.6557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9307    1.4911   -1.5282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0479    0.8492    0.7268 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1020    1.1530    1.5891 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0632   -0.0028    1.5016 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6198   -0.5521    2.6474 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4861   -2.0890    0.7907 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9046   -2.9655    1.4735 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8207   -2.1299    0.5720 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3827   -1.1629   -0.1666 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7537   -1.1708   -0.4137 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1717    2.7990   -1.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6833    0.6715   -0.8749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0432   -2.0778    0.8659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2624   -0.6951   -0.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9788    1.3537   -1.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0060   -0.0372   -2.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9111    2.1359   -2.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5861    1.8037    0.4295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9403    0.8442    2.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1847    0.6175    1.7805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5848   -1.5439    2.6576 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0549   -1.7466   -1.2109 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7 14  1  0
 14 15  1  0
 14 12  1  0
 12 13  1  0
  7  6  1  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  4 19  1  0
 19 20  1  0
 19 18  2  0
 18 16  1  0
 16 17  2  0
 12  9  1  0
 16  6  1  0
 11 27  1  0
 10 25  1  0
 10 26  1  0
  9 24  1  1
  7 23  1  1
 14 30  1  1
 15 31  1  0
 12 28  1  6
 13 29  1  0
  5 22  1  0
  2 21  1  0
 20 32  1  0
M  END


  Mrv1652309042200102D          

 20 21  0  0  1  0            999 V2000
    0.8212    6.0027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1067    5.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1067    4.7652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078    4.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078    3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    3.1152    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    2.2902    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6548    1.8053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9097    1.0206    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4248    0.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3957    0.4394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7347    1.0206    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2197    0.3532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9897    1.8053    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7743    2.0602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0367    3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512    3.1152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0367    4.3527    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    4.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    5.5902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  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
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  1  0  0  0
  6 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
  4 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0183292

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=C(OC=O)C(O)=NC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H12N2O8/c13-2-5-6(15)7(16)9(20-5)12-1-4(19-3-14)8(17)11-10(12)18/h1,3,5-7,9,13,15-16H,2H2,(H,11,17,18)/t5-,6-,7-,9-/m1/s1

> <INCHI_KEY>
WTDLMHSRPAQBIA-JXOAFFINSA-N

> <FORMULA>
C10H12N2O8

> <MOLECULAR_WEIGHT>
288.212

> <EXACT_MASS>
288.059365354

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
24.880167641995303

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-2-oxo-1,2-dihydropyrimidin-5-yl formate

> <JCHEM_LOGP>
-2.4324380973333337

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.553145020606774

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.347652259673411

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9802998421297255

> <JCHEM_POLAR_SURFACE_AREA>
149.11999999999998

> <JCHEM_REFRACTIVITY>
59.515699999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-2-oxopyrimidin-5-yl formate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  O   UNK     0       1.533  11.205   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.199  10.435   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.199   8.895   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.134   8.125   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.134   6.585   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -2.468   5.815   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -2.468   4.275   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.222   3.370   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.698   1.905   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.793   0.659   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.739   0.820   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.238   1.905   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.143   0.659   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.714   3.370   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -5.179   3.846   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -3.802   6.585   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -5.136   5.815   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0      -3.802   8.125   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      -2.468   8.895   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.468  10.435   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   19                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   16                                                  
CONECT    7    6    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    7   15                                                  
CONECT   15   14                                                            
CONECT   16    6   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18    4   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-2-oxo-1,2-dihydropyrimidin-5-yl formic acid	Generator

Chemical Formula

C₁₀H₁₂N₂O₈

Average Mass

288.2120 Da

Monoisotopic Mass

288.05937 Da

IUPAC Name

1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-2-oxo-1,2-dihydropyrimidin-5-yl formate

Traditional Name

1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-2-oxopyrimidin-5-yl formate

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=C(OC=O)C(O)=NC1=O

InChI Identifier

InChI=1S/C10H12N2O8/c13-2-5-6(15)7(16)9(20-5)12-1-4(19-3-14)8(17)11-10(12)18/h1,3,5-7,9,13,15-16H,2H2,(H,11,17,18)/t5-,6-,7-,9-/m1/s1

InChI Key

WTDLMHSRPAQBIA-JXOAFFINSA-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
Serratia plymuthica	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleosides

Sub Class

Not Available

Direct Parent

Pyrimidine nucleosides

Alternative Parents

Substituents

Pyrimidine nucleoside
N-glycosyl compound
Glycosyl compound
Pentose monosaccharide
Hydroxypyrimidine
Pyrimidone
Pyrimidine
Monosaccharide
Hydropyrimidine
Heteroaromatic compound
Tetrahydrofuran
Secondary alcohol
Carboxylic acid ester
Oxacycle
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	-2.4	ChemAxon
pKa (Strongest Acidic)	6.35	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	149.12 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	59.52 m³·mol⁻¹	ChemAxon
Polarizability	24.88 Å³	ChemAxon
Number of Rings	2	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

163185988

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-2-oxopyrimidin-5-yl formate (NP0183292)

MOL for NP0183292 (1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-2-oxopyrimidin-5-yl formate)

3D MOL for NP0183292 (1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-2-oxopyrimidin-5-yl formate)

3D SDF for NP0183292 (1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-2-oxopyrimidin-5-yl formate)

3D-SDF for NP0183292 (1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-2-oxopyrimidin-5-yl formate)

PDB for NP0183292 (1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-2-oxopyrimidin-5-yl formate)

3D PDB for NP0183292 (1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-2-oxopyrimidin-5-yl formate)

SMILES for NP0183292 (1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-2-oxopyrimidin-5-yl formate)

INCHI for NP0183292 (1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-2-oxopyrimidin-5-yl formate)

Structure for NP0183292 (1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-2-oxopyrimidin-5-yl formate)

3D Structure for NP0183292 (1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-2-oxopyrimidin-5-yl formate)