NP-MRD: Showing NP-Card for [(5r)-5-[(1r)-1,2-dihydroxyethyl]-4-hydroxy-2-oxo-5h-furan-3-yl]oxidanesulfonic acid (NP0184812)

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Record Information

Version

2.0

Created at

2022-09-04 00:02:17 UTC

Updated at

2022-09-04 00:02:17 UTC

NP-MRD ID

NP0184812

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(5r)-5-[(1r)-1,2-dihydroxyethyl]-4-hydroxy-2-oxo-5h-furan-3-yl]oxidanesulfonic acid

Description

Ascorbic acid-2-sulfate, also known as ascorbate-2-sulphate, belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. Ascorbic acid-2-sulfate is a metabolite of vitamin c. In living organisms ascorbate acts as an antioxidant by protecting the body against oxidative stress. It is also a cofactor in at least eight enzymatic reactions including several collagen synthesis reactions that, when dysfunctional, cause the most severe symptoms of scurvy. Ascorbic acid-2-sulfate is an extremely weak basic (essentially neutral) compound (based on its pKa). [(5r)-5-[(1r)-1,2-dihydroxyethyl]-4-hydroxy-2-oxo-5h-furan-3-yl]oxidanesulfonic acid is found in Artemia franciscana. Vitamin C or L-ascorbic acid or L-ascorbate is an essential nutrient for humans and certain other animal species.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 06151311252D          

 16 16  0  0  1  0            999 V2000
    1.2822    3.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0059   -1.5764    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.3415   -2.3300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7478   -1.9119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7596   -1.2408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    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  6  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  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  2  0  0  0  0
 11 14  2  0  0  0  0
  9 15  2  0  0  0  0
  5 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0184812

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@@H](O)[C@H]1OC(=O)C(OS(O)(=O)=O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C6H8O9S/c7-1-2(8)4-3(9)5(6(10)14-4)15-16(11,12)13/h2,4,7-9H,1H2,(H,11,12,13)/t2-,4-/m1/s1

> <INCHI_KEY>
XDBMXUKHMOFBPJ-VVJJHMBFSA-N

> <FORMULA>
C6H8O9S

> <MOLECULAR_WEIGHT>
256.187

> <EXACT_MASS>
255.988902544

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
20.09465454821644

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(5R)-5-[(1R)-1,2-dihydroxyethyl]-4-hydroxy-2-oxo-2,5-dihydrofuran-3-yl]oxidanesulfonic acid

> <ALOGPS_LOGP>
-2.03

> <JCHEM_LOGP>
-4.366406283379962

> <ALOGPS_LOGS>
-0.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.266827395043564

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.1937726803376956

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9797296470038077

> <JCHEM_POLAR_SURFACE_AREA>
150.58999999999997

> <JCHEM_REFRACTIVITY>
47.023900000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.35e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(5R)-5-[(1R)-1,2-dihydroxyethyl]-4-hydroxy-2-oxo-5H-furan-3-yl]oxidanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-JUN-13         0                                  
HETATM    1  O   UNK     0       2.393   5.930   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.393   4.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.274   4.390   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.306   1.175   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.735  -1.536   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.615  -1.536   0.000  0.00  0.00           O+0
HETATM   11  S   UNK     0       0.011  -2.943   0.000  0.00  0.00           S+0
HETATM   12  O   UNK     0       0.637  -4.349   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.396  -3.569   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.418  -2.316   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11                                                            
CONECT   15    9    5   16                                                  
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
Ascorbate-2-sulfate	Generator
Ascorbate-2-sulphate	Generator
Ascorbic acid-2-sulfuric acid	Generator
Ascorbic acid-2-sulphuric acid	Generator

Chemical Formula

C₆H₈O₉S

Average Mass

256.1870 Da

Monoisotopic Mass

255.98890 Da

IUPAC Name

[(5R)-5-[(1R)-1,2-dihydroxyethyl]-4-hydroxy-2-oxo-2,5-dihydrofuran-3-yl]oxidanesulfonic acid

Traditional Name

[(5R)-5-[(1R)-1,2-dihydroxyethyl]-4-hydroxy-2-oxo-5H-furan-3-yl]oxidanesulfonic acid

CAS Registry Number

Not Available

SMILES

OC[C@@H](O)[C@H]1OC(=O)C(OS(O)(=O)=O)=C1O

InChI Identifier

InChI=1S/C6H8O9S/c7-1-2(8)4-3(9)5(6(10)14-4)15-16(11,12)13/h2,4,7-9H,1H2,(H,11,12,13)/t2-,4-/m1/s1

InChI Key

XDBMXUKHMOFBPJ-VVJJHMBFSA-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
Artemia franciscana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dihydrofurans

Sub Class

Furanones

Direct Parent

Butenolides

Alternative Parents

Substituents

2-furanone
Sulfuric acid ester
Sulfate-ester
Sulfuric acid monoester
Vinylogous acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Organic sulfuric acid or derivatives
1,2-diol
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Primary alcohol
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic 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	ALOGPS
logP	-4.4	ChemAxon
logS	-0.88	ALOGPS
pKa (Strongest Acidic)	-2.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	150.59 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	47.02 m³·mol⁻¹	ChemAxon
Polarizability	20.09 Å³	ChemAxon
Number of Rings	1	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

HMDB0060649

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

98048983

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(5r)-5-[(1r)-1,2-dihydroxyethyl]-4-hydroxy-2-oxo-5h-furan-3-yl]oxidanesulfonic acid (NP0184812)

MOL for NP0184812 ([(5r)-5-[(1r)-1,2-dihydroxyethyl]-4-hydroxy-2-oxo-5h-furan-3-yl]oxidanesulfonic acid)

3D MOL for NP0184812 ([(5r)-5-[(1r)-1,2-dihydroxyethyl]-4-hydroxy-2-oxo-5h-furan-3-yl]oxidanesulfonic acid)

3D SDF for NP0184812 ([(5r)-5-[(1r)-1,2-dihydroxyethyl]-4-hydroxy-2-oxo-5h-furan-3-yl]oxidanesulfonic acid)

3D-SDF for NP0184812 ([(5r)-5-[(1r)-1,2-dihydroxyethyl]-4-hydroxy-2-oxo-5h-furan-3-yl]oxidanesulfonic acid)

PDB for NP0184812 ([(5r)-5-[(1r)-1,2-dihydroxyethyl]-4-hydroxy-2-oxo-5h-furan-3-yl]oxidanesulfonic acid)

3D PDB for NP0184812 ([(5r)-5-[(1r)-1,2-dihydroxyethyl]-4-hydroxy-2-oxo-5h-furan-3-yl]oxidanesulfonic acid)

SMILES for NP0184812 ([(5r)-5-[(1r)-1,2-dihydroxyethyl]-4-hydroxy-2-oxo-5h-furan-3-yl]oxidanesulfonic acid)

INCHI for NP0184812 ([(5r)-5-[(1r)-1,2-dihydroxyethyl]-4-hydroxy-2-oxo-5h-furan-3-yl]oxidanesulfonic acid)

Structure for NP0184812 ([(5r)-5-[(1r)-1,2-dihydroxyethyl]-4-hydroxy-2-oxo-5h-furan-3-yl]oxidanesulfonic acid)

3D Structure for NP0184812 ([(5r)-5-[(1r)-1,2-dihydroxyethyl]-4-hydroxy-2-oxo-5h-furan-3-yl]oxidanesulfonic acid)