NP-MRD: Showing NP-Card for Keratan (NP0086717)

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Record Information

Version

2.0

Created at

2022-05-11 16:29:02 UTC

Updated at

2022-05-11 16:29:03 UTC

NP-MRD ID

NP0086717

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Keratan

Description

Keratan, also known as kerato sulfate or sulfate, keratan, belongs to the class of organic compounds known as oligosaccharide sulfates. These are carbohydrates containing between 3 and 9 sugar units, one of which bear one or more sulfate groups. At least two types are known. Keratan is an extremely weak basic (essentially neutral) compound (based on its pKa). Keratan is a sulfated mucopolysaccharide initially isolated from bovine cornea. Keratan was first documented in 1985 (PMID: 2935158). A sulfated mucopolysaccharide initially isolated from bovine cornea (PMID: 15082343) (PMID: 2521451) (PMID: 2562661) (PMID: 2957502).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231218572D          

 66 69  0  0  1  0            999 V2000
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  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
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  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
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  6 66  1  6  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv0541 02231218572D          

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M  END
> <DATABASE_ID>
NP0086717

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)N[C@@H]1[C@@H](O)C[C@@H](COS(O)(=O)=O)O[C@H]1O[C@H]1[C@@H](O)[C@@H](COS(O)(=O)=O)O[C@@H](O[C@H]2[C@H](O)[C@@H](NC(C)=O)[C@H](O[C@@H]3[C@@H](O)[C@H](O)O[C@H](COS(O)(=O)=O)[C@@H]3O)O[C@@H]2COS(O)(=O)=O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H48N2O32S4/c1-8(31)29-15-11(33)3-10(4-52-63(40,41)42)56-26(15)62-24-18(35)13(6-54-65(46,47)48)58-28(21(24)38)60-22-14(7-55-66(49,50)51)59-27(16(19(22)36)30-9(2)32)61-23-17(34)12(5-53-64(43,44)45)57-25(39)20(23)37/h10-28,33-39H,3-7H2,1-2H3,(H,29,31)(H,30,32)(H,40,41,42)(H,43,44,45)(H,46,47,48)(H,49,50,51)/t10-,11-,12+,13+,14+,15+,16+,17-,18-,19+,20+,21+,22+,23-,24-,25+,26-,27-,28-/m0/s1

> <INCHI_KEY>
KXCLCNHUUKTANI-RBIYJLQWSA-N

> <FORMULA>
C28H48N2O32S4

> <MOLECULAR_WEIGHT>
1052.935

> <EXACT_MASS>
1052.10730021

> <JCHEM_ACCEPTOR_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
92.21723409467134

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
13

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2S,4S,5R,6S)-5-acetamido-6-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6S)-5-acetamido-4-hydroxy-2-[(sulfooxy)methyl]-6-{[(2R,3R,4S,5S,6R)-2,3,5-trihydroxy-6-[(sulfooxy)methyl]oxan-4-yl]oxy}oxan-3-yl]oxy}-3,5-dihydroxy-6-[(sulfooxy)methyl]oxan-4-yl]oxy}-4-hydroxyoxan-2-yl]methoxy}sulfonic acid

> <ALOGPS_LOGP>
-2.46

> <JCHEM_LOGP>
-15.294261471109724

> <ALOGPS_LOGS>
-1.63

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
-2.1675817070219834

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.5937952165495286

> <JCHEM_PKA_STRONGEST_BASIC>
-3.954530640567982

> <JCHEM_POLAR_SURFACE_AREA>
518.82

> <JCHEM_REFRACTIVITY>
194.2360000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.49e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2S,4S,5R,6S)-5-acetamido-6-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6S)-5-acetamido-4-hydroxy-2-[(sulfooxy)methyl]-6-{[(2R,3R,4S,5S,6R)-2,3,5-trihydroxy-6-[(sulfooxy)methyl]oxan-4-yl]oxy}oxan-3-yl]oxy}-3,5-dihydroxy-6-[(sulfooxy)methyl]oxan-4-yl]oxy}-4-hydroxyoxan-2-yl]methoxysulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       0.150 -10.403   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.184  -9.633   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.517 -10.403   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      -1.184  -8.093   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       0.150  -7.323   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.484  -8.093   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.817  -7.323   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.817  -5.783   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.484  -5.013   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.150  -5.783   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.184  -5.013   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.184  -3.473   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.150  -2.703   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.150  -1.163   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.184  -0.393   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.517  -1.163   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.517  -2.703   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -3.851  -3.473   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -3.851  -0.393   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -3.851   1.147   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.517   1.917   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.517   3.457   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -3.851   4.227   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.185   3.457   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.185   1.917   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -6.518   1.147   0.000  0.00  0.00           O+0
HETATM   27  N   UNK     0      -6.518   4.227   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0      -6.518   5.767   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -5.185   6.537   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -7.852   6.537   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -3.851   5.767   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -2.517   6.537   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.184   5.767   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.150   6.537   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       0.150   8.077   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -1.184   8.847   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.517   8.077   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -3.851   8.847   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -1.184  10.387   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       1.484   5.767   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       1.484   4.227   0.000  0.00  0.00           O+0
HETATM   42  S   UNK     0       2.817   3.457   0.000  0.00  0.00           S+0
HETATM   43  O   UNK     0       3.587   4.790   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       1.484   2.687   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       4.151   2.687   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      -1.184   4.227   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -1.184   1.147   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       0.150   1.917   0.000  0.00  0.00           O+0
HETATM   49  S   UNK     0       1.484   1.147   0.000  0.00  0.00           S+0
HETATM   50  O   UNK     0       2.254   2.480   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0       0.714  -0.187   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0       2.817   0.377   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0       1.484  -0.393   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0       2.817  -1.163   0.000  0.00  0.00           O+0
HETATM   55  S   UNK     0       4.151  -0.393   0.000  0.00  0.00           S+0
HETATM   56  O   UNK     0       3.381   0.940   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0       4.921  -1.727   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0       5.485   0.377   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0       1.484  -3.473   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0       4.151  -5.013   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0       5.485  -5.783   0.000  0.00  0.00           O+0
HETATM   62  S   UNK     0       6.818  -5.013   0.000  0.00  0.00           S+0
HETATM   63  O   UNK     0       6.048  -3.680   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0       7.588  -6.347   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0       8.152  -4.243   0.000  0.00  0.00           O+0
HETATM   66  O   UNK     0       1.484  -9.633   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7   66                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   60                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14   59                                                  
CONECT   14   13   15   53                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   12   18                                                  
CONECT   18   17                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22   47                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   31                                                  
CONECT   24   23   25   27                                                  
CONECT   25   24   20   26                                                  
CONECT   26   25                                                            
CONECT   27   24   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   23   32                                                       
CONECT   32   31   33   37                                                  
CONECT   33   32   34   46                                                  
CONECT   34   33   35   40                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   39                                                  
CONECT   37   36   32   38                                                  
CONECT   38   37                                                            
CONECT   39   36                                                            
CONECT   40   34   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43   44   45                                             
CONECT   43   42                                                            
CONECT   44   42                                                            
CONECT   45   42                                                            
CONECT   46   33                                                            
CONECT   47   21   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50   51   52                                             
CONECT   50   49                                                            
CONECT   51   49                                                            
CONECT   52   49                                                            
CONECT   53   14   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56   57   58                                             
CONECT   56   55                                                            
CONECT   57   55                                                            
CONECT   58   55                                                            
CONECT   59   13                                                            
CONECT   60    8   61                                                       
CONECT   61   60   62                                                       
CONECT   62   61   63   64   65                                             
CONECT   63   62                                                            
CONECT   64   62                                                            
CONECT   65   62                                                            
CONECT   66    6                                                            
MASTER        0    0    0    0    0    0    0    0   66    0  138    0
END

View in JSmol

Synonyms

Value	Source
Keratan 6'-sulfate	HMDB
Keratan 6'-sulphate	HMDB
Keratan sulfate	HMDB
Keratan sulphate	HMDB
Kerato 6'-sulfate	HMDB
Kerato 6'-sulphate	HMDB
Kerato sulfate	HMDB
Kerato sulphate	HMDB
N-[(2S,3R,4S,6S)-2-{[(2S,3R,4S,5S,6R)-3,5-dihydroxy-2-{[(2R,3S,4R,5R,6S)-4-hydroxy-5-[(1-hydroxyethylidene)amino]-2-[(sulfooxy)methyl]-6-{[(2R,3R,4S,5S,6R)-2,3,5-trihydroxy-6-[(sulfooxy)methyl]oxan-4-yl]oxy}oxan-3-yl]oxy}-6-[(sulfooxy)methyl]oxan-4-yl]oxy}-4-hydroxy-6-[(sulfooxy)methyl]oxan-3-yl]ethanimidate	HMDB
N-[(2S,3R,4S,6S)-2-{[(2S,3R,4S,5S,6R)-3,5-dihydroxy-2-{[(2R,3S,4R,5R,6S)-4-hydroxy-5-[(1-hydroxyethylidene)amino]-2-[(sulphooxy)methyl]-6-{[(2R,3R,4S,5S,6R)-2,3,5-trihydroxy-6-[(sulphooxy)methyl]oxan-4-yl]oxy}oxan-3-yl]oxy}-6-[(sulphooxy)methyl]oxan-4-yl]oxy}-4-hydroxy-6-[(sulphooxy)methyl]oxan-3-yl]ethanimidate	HMDB
N-[(2S,3R,4S,6S)-2-{[(2S,3R,4S,5S,6R)-3,5-dihydroxy-2-{[(2R,3S,4R,5R,6S)-4-hydroxy-5-[(1-hydroxyethylidene)amino]-2-[(sulphooxy)methyl]-6-{[(2R,3R,4S,5S,6R)-2,3,5-trihydroxy-6-[(sulphooxy)methyl]oxan-4-yl]oxy}oxan-3-yl]oxy}-6-[(sulphooxy)methyl]oxan-4-yl]oxy}-4-hydroxy-6-[(sulphooxy)methyl]oxan-3-yl]ethanimidic acid	HMDB
Keratosulfate	HMDB
Sulfate, keratan	HMDB

Chemical Formula

C₂₈H₄₈N₂O₃₂S₄

Average Mass

1052.9350 Da

Monoisotopic Mass

1052.10730 Da

IUPAC Name

{[(2S,4S,5R,6S)-5-acetamido-6-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6S)-5-acetamido-4-hydroxy-2-[(sulfooxy)methyl]-6-{[(2R,3R,4S,5S,6R)-2,3,5-trihydroxy-6-[(sulfooxy)methyl]oxan-4-yl]oxy}oxan-3-yl]oxy}-3,5-dihydroxy-6-[(sulfooxy)methyl]oxan-4-yl]oxy}-4-hydroxyoxan-2-yl]methoxy}sulfonic acid

Traditional Name

[(2S,4S,5R,6S)-5-acetamido-6-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6S)-5-acetamido-4-hydroxy-2-[(sulfooxy)methyl]-6-{[(2R,3R,4S,5S,6R)-2,3,5-trihydroxy-6-[(sulfooxy)methyl]oxan-4-yl]oxy}oxan-3-yl]oxy}-3,5-dihydroxy-6-[(sulfooxy)methyl]oxan-4-yl]oxy}-4-hydroxyoxan-2-yl]methoxysulfonic acid

CAS Registry Number

Not Available

SMILES

CC(=O)N[C@@H]1[C@@H](O)C[C@@H](COS(O)(=O)=O)O[C@H]1O[C@H]1[C@@H](O)[C@@H](COS(O)(=O)=O)O[C@@H](O[C@H]2[C@H](O)[C@@H](NC(C)=O)[C@H](O[C@@H]3[C@@H](O)[C@H](O)O[C@H](COS(O)(=O)=O)[C@@H]3O)O[C@@H]2COS(O)(=O)=O)[C@@H]1O

InChI Identifier

InChI=1S/C28H48N2O32S4/c1-8(31)29-15-11(33)3-10(4-52-63(40,41)42)56-26(15)62-24-18(35)13(6-54-65(46,47)48)58-28(21(24)38)60-22-14(7-55-66(49,50)51)59-27(16(19(22)36)30-9(2)32)61-23-17(34)12(5-53-64(43,44)45)57-25(39)20(23)37/h10-28,33-39H,3-7H2,1-2H3,(H,29,31)(H,30,32)(H,40,41,42)(H,43,44,45)(H,46,47,48)(H,49,50,51)/t10-,11-,12+,13+,14+,15+,16+,17-,18-,19+,20+,21+,22+,23-,24-,25+,26-,27-,28-/m0/s1

InChI Key

KXCLCNHUUKTANI-RBIYJLQWSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oligosaccharide sulfates. These are carbohydrates containing between 3 and 9 sugar units, one of which bear one or more sulfate groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Oligosaccharide sulfates

Alternative Parents

Substituents

Oligosaccharide sulfate
N-acyl-alpha-hexosamine
Glycosyl compound
O-glycosyl compound
Oxane
Sulfuric acid monoester
Sulfuric acid ester
Alkyl sulfate
Sulfate-ester
Organic sulfuric acid or derivatives
Acetamide
Carboxamide group
Hemiacetal
Secondary alcohol
Secondary carboxylic acid amide
Oxacycle
Carboxylic acid derivative
Acetal
Polyol
Organoheterocyclic compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Alcohol
Organic nitrogen compound
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	-2.5	ALOGPS
logP	-15	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	-2.6	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	28	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	518.82 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	194.24 m³·mol⁻¹	ChemAxon
Polarizability	92.22 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0001165

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022459

KNApSAcK ID

Not Available

Chemspider ID

394000

KEGG Compound ID

C00573

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

446715

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Isnard N, Fodil-Bourahla I, Robert AM, Robert L: Pharmacology of skin aging. Stimulation of glycosaminoglycan biosynthesis by L-fucose and fucose-rich polysaccharides, effect of in vitro aging of fibroblasts. Biomed Pharmacother. 2004 Apr;58(3):202-4. [PubMed:15082343 ]
Block JA, Schnitzer TJ, Andersson GB, Lenz ME, Jeffery R, McNeill TW, Thonar EJ: The effect of chemonucleolysis on serum keratan sulfate levels in humans. Arthritis Rheum. 1989 Jan;32(1):100-4. doi: 10.1002/anr.1780320118. [PubMed:2521451 ]
Thonar EJ, Lenz ME, Klintworth GK, Caterson B, Pachman LM, Glickman P, Katz R, Huff J, Kuettner KE: Quantification of keratan sulfate in blood as a marker of cartilage catabolism. Arthritis Rheum. 1985 Dec;28(12):1367-76. doi: 10.1002/art.1780281209. [PubMed:2935158 ]
Sorrell JM, Caterson B: Detection of age-related changes in the distributions of keratan sulfates and chondroitin sulfates in developing chick limbs: an immunocytochemical study. Development. 1989 Aug;106(4):657-63. doi: 10.1242/dev.106.4.657. [PubMed:2562661 ]
Thonar EJ, Schnitzer TJ, Kuettner KE: Quantification of keratan sulfate in blood as a marker of cartilage catabolism. J Rheumatol. 1987 May;14 Spec No:23-4. [PubMed:2957502 ]

Showing NP-Card for Keratan (NP0086717)

MOL for NP0086717 (Keratan)

3D MOL for NP0086717 (Keratan)

3D SDF for NP0086717 (Keratan)

3D-SDF for NP0086717 (Keratan)

PDB for NP0086717 (Keratan)

3D PDB for NP0086717 (Keratan)

SMILES for NP0086717 (Keratan)

INCHI for NP0086717 (Keratan)

Structure for NP0086717 (Keratan)

3D Structure for NP0086717 (Keratan)