NP-MRD: Showing NP-Card for (4s,5s)-4,5-dihydroxy-2-oxo-6-sulfohexanoic acid (NP0224271)

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Record Information

Version

2.0

Created at

2022-09-06 02:35:30 UTC

Updated at

2022-09-06 02:35:30 UTC

NP-MRD ID

NP0224271

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4s,5s)-4,5-dihydroxy-2-oxo-6-sulfohexanoic acid

Description

2-Dehydro-3,6-dideoxy-6-sulfo-D-gluconic acid belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain. 2-Dehydro-3,6-dideoxy-6-sulfo-D-gluconic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on 2-dehydro-3,6-dideoxy-6-sulfo-D-gluconic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062204352D          

 15 14  0  0  1  0            999 V2000
   -0.1914    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3809    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    1.1270    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243    1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974    1.8414    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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  2  0  0  0  0
 12 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0224271

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H](CC(=O)C(O)=O)[C@H](O)CS(O)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O8S/c7-3(1-4(8)6(10)11)5(9)2-15(12,13)14/h3,5,7,9H,1-2H2,(H,10,11)(H,12,13,14)/t3-,5+/m0/s1

> <INCHI_KEY>
COLOZALSGXIPJV-WVZVXSGGSA-N

> <FORMULA>
C6H10O8S

> <MOLECULAR_WEIGHT>
242.2

> <EXACT_MASS>
242.009638456

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
19.70461356455793

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S,5S)-4,5-dihydroxy-2-oxo-6-sulfohexanoic acid

> <JCHEM_LOGP>
-3.427573991128452

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.4580942820820946

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.3859663689637873

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2548252743419726

> <JCHEM_POLAR_SURFACE_AREA>
149.2

> <JCHEM_REFRACTIVITY>
44.710300000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4S,5S)-4,5-dihydroxy-2-oxo-6-sulfohexanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  O   UNK     0      -0.357   1.334   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.976   3.644   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.310  -0.206   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.977  -0.206   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.311   2.104   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.311   3.644   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.645   1.334   0.000  0.00  0.00           C+0
HETATM   12  S   UNK     0       8.978   2.104   0.000  0.00  0.00           S+0
HETATM   13  O   UNK     0      10.312   2.874   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       9.748   0.770   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       8.208   3.437   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

View in JSmol

Synonyms

Value	Source
2-Dehydro-3,6-dideoxy-6-sulfO-D-gluconate	Generator
2-Dehydro-3,6-dideoxy-6-sulphO-D-gluconate	Generator
2-Dehydro-3,6-dideoxy-6-sulphO-D-gluconic acid	Generator

Chemical Formula

C₆H₁₀O₈S

Average Mass

242.2000 Da

Monoisotopic Mass

242.00964 Da

IUPAC Name

(4S,5S)-4,5-dihydroxy-2-oxo-6-sulfohexanoic acid

Traditional Name

(4S,5S)-4,5-dihydroxy-2-oxo-6-sulfohexanoic acid

CAS Registry Number

Not Available

SMILES

O[C@@H](CC(=O)C(O)=O)[C@H](O)CS(O)(=O)=O

InChI Identifier

InChI=1S/C6H10O8S/c7-3(1-4(8)6(10)11)5(9)2-15(12,13)14/h3,5,7,9H,1-2H2,(H,10,11)(H,12,13,14)/t3-,5+/m0/s1

InChI Key

COLOZALSGXIPJV-WVZVXSGGSA-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 medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Medium-chain keto acids and derivatives

Direct Parent

Medium-chain keto acids and derivatives

Alternative Parents

Substituents

Medium-chain keto acid
Hydroxy fatty acid
Thia fatty acid
Alpha-keto acid
Fatty acyl
Beta-hydroxy ketone
Alpha-hydroxy ketone
Alkanesulfonic acid
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Organosulfonic acid
Sulfonyl
1,2-diol
Secondary alcohol
Ketone
Carboxylic acid
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organooxygen compound
Carbonyl group
Organosulfur compound
Hydrocarbon derivative
Organic oxide
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	-3.4	ChemAxon
pKa (Strongest Acidic)	-1.4	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	149.2 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	44.71 m³·mol⁻¹	ChemAxon
Polarizability	19.7 Å³	ChemAxon
Number of Rings	0	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

58164021

KEGG Compound ID

Not Available

BioCyc ID

CPD-18483

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

92136147

PDB ID

Not Available

ChEBI ID

90095

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4s,5s)-4,5-dihydroxy-2-oxo-6-sulfohexanoic acid (NP0224271)

MOL for NP0224271 ((4s,5s)-4,5-dihydroxy-2-oxo-6-sulfohexanoic acid)

3D MOL for NP0224271 ((4s,5s)-4,5-dihydroxy-2-oxo-6-sulfohexanoic acid)

3D SDF for NP0224271 ((4s,5s)-4,5-dihydroxy-2-oxo-6-sulfohexanoic acid)

3D-SDF for NP0224271 ((4s,5s)-4,5-dihydroxy-2-oxo-6-sulfohexanoic acid)

PDB for NP0224271 ((4s,5s)-4,5-dihydroxy-2-oxo-6-sulfohexanoic acid)

3D PDB for NP0224271 ((4s,5s)-4,5-dihydroxy-2-oxo-6-sulfohexanoic acid)

SMILES for NP0224271 ((4s,5s)-4,5-dihydroxy-2-oxo-6-sulfohexanoic acid)

INCHI for NP0224271 ((4s,5s)-4,5-dihydroxy-2-oxo-6-sulfohexanoic acid)

Structure for NP0224271 ((4s,5s)-4,5-dihydroxy-2-oxo-6-sulfohexanoic acid)

3D Structure for NP0224271 ((4s,5s)-4,5-dihydroxy-2-oxo-6-sulfohexanoic acid)