NP-MRD: Showing NP-Card for {6-[3-(hexadecanoyloxy)-2-hydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl}methanesulfonic acid (NP0261725)

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Record Information

Version

2.0

Created at

2022-09-08 04:14:56 UTC

Updated at

2022-09-08 04:14:56 UTC

NP-MRD ID

NP0261725

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{6-[3-(hexadecanoyloxy)-2-hydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl}methanesulfonic acid

Description

{6-[3-(Hexadecanoyloxy)-2-hydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl}methanesulfonic acid belongs to the class of organic compounds known as sulfoquinovosyl 1-monoacylglycerols. These are sulfoquinovosylmonoacylglycerols where the glycerol moiety is 1-O acylated. {6-[3-(hexadecanoyloxy)-2-hydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl}methanesulfonic acid is found in Ulva pertusa. Based on a literature review very few articles have been published on {6-[3-(hexadecanoyloxy)-2-hydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl}methanesulfonic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082206142D          

 37 37  0  0  0  0            999 V2000
    5.7158  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.2881  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.5749  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.1473  -12.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   21.4341  -12.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   22.8631  -10.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6881  -11.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0381  -11.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1486  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   20.0052  -14.0250    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
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  6  7  1  0  0  0  0
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  9 10  1  0  0  0  0
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 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
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 20 21  1  0  0  0  0
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 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
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 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 24 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END

     RDKit          3D

 85 85  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652309082206142D          

 37 37  0  0  0  0            999 V2000
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   22.8631  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8631  -11.5500    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.8631  -10.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6881  -11.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0381  -11.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1486  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8631  -14.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4341  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4341  -14.8500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7197  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0052  -14.0250    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  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  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
 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  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  2  0  0  0  0
 28 31  1  0  0  0  0
 26 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 24 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0261725

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCC(=O)OCC(O)COC1OC(CS(O)(=O)=O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H48O11S/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-21(27)34-16-19(26)17-35-25-24(30)23(29)22(28)20(36-25)18-37(31,32)33/h19-20,22-26,28-30H,2-18H2,1H3,(H,31,32,33)

> <INCHI_KEY>
PVPLOFLVMFDWJG-UHFFFAOYSA-N

> <FORMULA>
C25H48O11S

> <MOLECULAR_WEIGHT>
556.71

> <EXACT_MASS>
556.29173354

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
62.42600875758241

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{6-[3-(hexadecanoyloxy)-2-hydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl}methanesulfonic acid

> <JCHEM_LOGP>
3.0215969513333336

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.204843798050817

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.1892066322427537

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3893706439416444

> <JCHEM_POLAR_SURFACE_AREA>
180.04999999999998

> <JCHEM_REFRACTIVITY>
134.91479999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
{6-[3-(hexadecanoyloxy)-2-hydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl}methanesulfonic acid

> <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  C   UNK     0      10.669 -23.100   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.003 -23.870   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.337 -23.100   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.670 -23.870   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.004 -23.100   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.338 -23.870   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.672 -23.100   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      20.005 -23.870   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.339 -23.100   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.673 -23.870   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      24.006 -23.100   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      25.340 -23.870   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      26.674 -23.100   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      28.007 -23.870   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      29.341 -23.100   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      30.675 -23.870   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      30.675 -25.410   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      32.008 -23.100   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      33.342 -23.870   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      34.676 -23.100   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      34.676 -21.560   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      36.009 -23.870   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      37.343 -23.100   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      38.677 -23.870   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      40.010 -23.100   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      41.344 -23.870   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      42.678 -23.100   0.000  0.00  0.00           C+0
HETATM   28  S   UNK     0      42.678 -21.560   0.000  0.00  0.00           S+0
HETATM   29  O   UNK     0      42.678 -20.020   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      44.218 -21.560   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      41.138 -21.560   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      41.344 -25.410   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      42.678 -26.180   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      40.010 -26.180   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      40.010 -27.720   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      38.677 -25.410   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      37.343 -26.180   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   36                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28                                                            
CONECT   32   26   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   24   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   74    0
END

View in JSmol

Synonyms

Value	Source
{6-[3-(hexadecanoyloxy)-2-hydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl}methanesulfonate	Generator
{6-[3-(hexadecanoyloxy)-2-hydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl}methanesulphonate	Generator
{6-[3-(hexadecanoyloxy)-2-hydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl}methanesulphonic acid	Generator

Chemical Formula

C₂₅H₄₈O₁₁S

Average Mass

556.7100 Da

Monoisotopic Mass

556.29173 Da

IUPAC Name

{6-[3-(hexadecanoyloxy)-2-hydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl}methanesulfonic acid

Traditional Name

{6-[3-(hexadecanoyloxy)-2-hydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl}methanesulfonic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCC(=O)OCC(O)COC1OC(CS(O)(=O)=O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C25H48O11S/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-21(27)34-16-19(26)17-35-25-24(30)23(29)22(28)20(36-25)18-37(31,32)33/h19-20,22-26,28-30H,2-18H2,1H3,(H,31,32,33)

InChI Key

PVPLOFLVMFDWJG-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
Ulva pertusa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sulfoquinovosyl 1-monoacylglycerols. These are sulfoquinovosylmonoacylglycerols where the glycerol moiety is 1-O acylated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerolipids

Sub Class

Glycosylglycerols

Direct Parent

Sulfoquinovosyl 1-monoacylglycerols

Alternative Parents

Substituents

Sulfoquinovosyl 1-monoacylglycerol
Glycosyl compound
O-glycosyl compound
Fatty acid ester
Monosaccharide
Fatty acyl
Oxane
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Organosulfonic acid
Sulfonyl
Alkanesulfonic acid
Secondary alcohol
Carboxylic acid ester
Polyol
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Acetal
Carboxylic acid derivative
Organosulfur compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
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	3.02	ChemAxon
pKa (Strongest Acidic)	-1.2	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	180.05 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	134.91 m³·mol⁻¹	ChemAxon
Polarizability	62.43 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

11655714

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

18756075

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for {6-[3-(hexadecanoyloxy)-2-hydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl}methanesulfonic acid (NP0261725)

MOL for NP0261725 ({6-[3-(hexadecanoyloxy)-2-hydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl}methanesulfonic acid)

3D MOL for NP0261725 ({6-[3-(hexadecanoyloxy)-2-hydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl}methanesulfonic acid)

3D SDF for NP0261725 ({6-[3-(hexadecanoyloxy)-2-hydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl}methanesulfonic acid)

3D-SDF for NP0261725 ({6-[3-(hexadecanoyloxy)-2-hydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl}methanesulfonic acid)

PDB for NP0261725 ({6-[3-(hexadecanoyloxy)-2-hydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl}methanesulfonic acid)

3D PDB for NP0261725 ({6-[3-(hexadecanoyloxy)-2-hydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl}methanesulfonic acid)

SMILES for NP0261725 ({6-[3-(hexadecanoyloxy)-2-hydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl}methanesulfonic acid)

INCHI for NP0261725 ({6-[3-(hexadecanoyloxy)-2-hydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl}methanesulfonic acid)

Structure for NP0261725 ({6-[3-(hexadecanoyloxy)-2-hydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl}methanesulfonic acid)

3D Structure for NP0261725 ({6-[3-(hexadecanoyloxy)-2-hydroxypropoxy]-3,4,5-trihydroxyoxan-2-yl}methanesulfonic acid)