NP-MRD: Showing NP-Card for [5-(6-amino-2-chloropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl sulfamate (NP0260808)

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Record Information

Version

2.0

Created at

2022-09-08 03:04:26 UTC

Updated at

2022-09-08 03:04:26 UTC

NP-MRD ID

NP0260808

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[5-(6-amino-2-chloropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl sulfamate

Description

5'-Sulfamoyl-2-chloroadenosine, also known as dealanylascamycin, 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. Based on a literature review very few articles have been published on 5'-Sulfamoyl-2-chloroadenosine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
   -5.8607    1.3387    0.6008 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9582    0.3553    0.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3703   -0.8826   -0.2168 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5018   -1.8085   -0.6693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0760   -3.4225   -1.1067 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.2045   -1.4903   -0.7825 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7108   -0.2814   -0.4656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6212    0.6539   -0.0029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9336    1.7714    0.2511 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6304    1.5693   -0.0351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5009    0.3046   -0.4754 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2667   -0.3611   -0.9034 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7103    0.5297   -1.2466 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5011    0.7976   -0.1629 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8657    0.1507   -0.4318 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6693    0.4334    0.6891 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1921   -0.2549    0.4538 S   0  0  0  0  0  6  0  0  0  0  0  0
    6.2793    0.9947    0.0069 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6865   -0.8842    1.7245 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1062   -1.3216   -0.6007 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9242    0.0576    1.0303 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9104   -0.3547    1.9074 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2577   -1.0982    0.3129 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7651   -1.6625    1.0586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5960    1.9857    1.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8075    1.3719    0.1335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8271    2.2903    0.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4961   -1.0820   -1.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6068    1.8666    0.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7858   -0.9398   -0.4832 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3378    0.5575   -1.3382 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2972    1.0319   -1.0357 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0480    1.9081    0.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1158    0.6341    1.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5819   -0.2948    2.8265 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0093   -1.8271   -0.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7588   -2.6371    0.9025 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 17 20  2  0
 14 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 11  7  1  0
  7  6  2  0
  6  4  1  0
  4  5  1  0
  4  3  2  0
  3  2  1  0
  7  8  1  0
 23 12  1  0
  1 25  1  0
  1 26  1  0
 10 27  1  0
 12 28  1  6
 14 29  1  1
 15 30  1  0
 15 31  1  0
 18 32  1  0
 18 33  1  0
 21 34  1  1
 22 35  1  0
 23 36  1  6
 24 37  1  0
M  END


  Mrv1652309082205042D          

 24 26  0  0  0  0            999 V2000
    3.2789    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0098   -1.7070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249   -2.3744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -3.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2278   -3.7722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4827   -4.5568    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.7377   -5.3414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6981   -4.8117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2674   -4.3018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7403   -2.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0728   -2.6044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7403   -1.2945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0728   -0.8096    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  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  2  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 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  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 17 20  2  0  0  0  0
 14 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 12 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0260808

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=C2N=CN(C3OC(COS(N)(=O)=O)C(O)C3O)C2=NC(Cl)=N1

> <INCHI_IDENTIFIER>
InChI=1S/C10H13ClN6O6S/c11-10-15-7(12)4-8(16-10)17(2-14-4)9-6(19)5(18)3(23-9)1-22-24(13,20)21/h2-3,5-6,9,18-19H,1H2,(H2,12,15,16)(H2,13,20,21)

> <INCHI_KEY>
JHUGCRSKMUFKHR-UHFFFAOYSA-N

> <FORMULA>
C10H13ClN6O6S

> <MOLECULAR_WEIGHT>
380.76

> <EXACT_MASS>
380.030581

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
34.121147287390166

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[5-(6-amino-2-chloro-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl sulfamate

> <JCHEM_LOGP>
-1.7023037053333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.494356166006877

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.299796836742795

> <JCHEM_PKA_STRONGEST_BASIC>
1.3062452413311676

> <JCHEM_POLAR_SURFACE_AREA>
188.70000000000002

> <JCHEM_REFRACTIVITY>
80.2214

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[5-(6-amino-2-chloropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl sulfamate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  N   UNK     0       6.121   3.850   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       7.454   1.540   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    5 Cl   UNK     0       8.788  -0.770   0.000  0.00  0.00          Cl+0
HETATM    6  N   UNK     0       6.121  -0.770   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       3.322   2.016   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       3.322  -0.476   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       2.846  -1.941   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.752  -3.186   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.846  -4.432   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.322  -5.897   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.292  -7.041   0.000  0.00  0.00           O+0
HETATM   17  S   UNK     0       2.768  -8.506   0.000  0.00  0.00           S+0
HETATM   18  N   UNK     0       3.244  -9.971   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       1.303  -8.982   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.232  -8.030   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.382  -3.956   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.136  -4.862   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.382  -2.416   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.136  -1.511   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    2    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    7   12                                                  
CONECT   12   11   13   23                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17                                                            
CONECT   21   14   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   12   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
5'-Sulphamoyl-2-chloroadenosine	Generator
Dealanylascamycin	HMDB

Chemical Formula

C₁₀H₁₃ClN₆O₆S

Average Mass

380.7600 Da

Monoisotopic Mass

380.03058 Da

IUPAC Name

[5-(6-amino-2-chloro-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl sulfamate

Traditional Name

[5-(6-amino-2-chloropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl sulfamate

CAS Registry Number

Not Available

SMILES

NC1=C2N=CN(C3OC(COS(N)(=O)=O)C(O)C3O)C2=NC(Cl)=N1

InChI Identifier

InChI=1S/C10H13ClN6O6S/c11-10-15-7(12)4-8(16-10)17(2-14-4)9-6(19)5(18)3(23-9)1-22-24(13,20)21/h2-3,5-6,9,18-19H,1H2,(H2,12,15,16)(H2,13,20,21)

InChI Key

JHUGCRSKMUFKHR-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 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-aminopurine
Pentose monosaccharide
Imidazopyrimidine
Purine
Aminopyrimidine
2-halopyrimidine
Halopyrimidine
Aryl chloride
Aryl halide
Monosaccharide
N-substituted imidazole
Imidolactam
Pyrimidine
Oxolane
Azole
Organic sulfuric acid or derivatives
Heteroaromatic compound
Imidazole
Secondary alcohol
1,2-diol
Organoheterocyclic compound
Azacycle
Oxacycle
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Organochloride
Organic nitrogen compound
Organonitrogen compound
Primary amine
Organooxygen compound
Amine
Organic oxygen compound
Alcohol
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	-1.7	ChemAxon
pKa (Strongest Acidic)	11.3	ChemAxon
pKa (Strongest Basic)	1.31	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	188.7 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	80.22 m³·mol⁻¹	ChemAxon
Polarizability	34.12 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

HMDB0248477

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

15997272

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13994713

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [5-(6-amino-2-chloropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl sulfamate (NP0260808)

MOL for NP0260808 ([5-(6-amino-2-chloropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl sulfamate)

3D MOL for NP0260808 ([5-(6-amino-2-chloropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl sulfamate)

3D SDF for NP0260808 ([5-(6-amino-2-chloropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl sulfamate)

3D-SDF for NP0260808 ([5-(6-amino-2-chloropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl sulfamate)

PDB for NP0260808 ([5-(6-amino-2-chloropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl sulfamate)

3D PDB for NP0260808 ([5-(6-amino-2-chloropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl sulfamate)

SMILES for NP0260808 ([5-(6-amino-2-chloropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl sulfamate)

INCHI for NP0260808 ([5-(6-amino-2-chloropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl sulfamate)

Structure for NP0260808 ([5-(6-amino-2-chloropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl sulfamate)

3D Structure for NP0260808 ([5-(6-amino-2-chloropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl sulfamate)