NP-MRD: Showing NP-Card for Salicin (NP0001377)

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Record Information

Version

2.0

Created at

2006-08-12 23:28:36 UTC

Updated at

2024-09-03 04:18:32 UTC

NP-MRD ID

NP0001377

Natural Product DOI

https://doi.org/10.57994/1424

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Salicin

Description

Salicin, also known as salicoside or delta-salicin, is an aryl beta-D-glucoside that is salicyl alcohol in which the phenolic hydrogen has been replaced by a beta-D-glucosyl residue. It has a role as a prodrug, an antipyretic, a non-narcotic analgesic, a non-steroidal anti-inflammatory drug, an EC 1.14.99.1 (Prostaglandin-endoperoxide synthase) inhibitor and a metabolite. It is an aryl beta-D-glucoside, an aromatic primary alcohol and a member of benzyl alcohols. It derives from a salicyl alcohol. Salicin belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Salicin exists in all living organisms, ranging from bacteria to humans. Salicin is a bitter tasting compound.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0003546
     RDKit          3D
Salicin
 38 39  0  0  0  0  0  0  0  0999 V2000
    4.1282    2.2867   -0.7564 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2311    1.2585   -1.1260 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1300    0.2825    0.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2592   -0.3349    0.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0675   -1.2045    1.5579 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8632   -1.4397    2.1536 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7493   -0.7496    1.5975 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8676    0.0761    0.5709 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8909    0.7614   -0.0551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4207    0.5469   -0.3831 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3423    1.1947    0.3243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6631    0.9453   -0.0672 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5271    1.6287    0.9849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1454    1.0994    2.2241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9878   -0.5248   -0.1562 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2904   -0.7010   -0.4929 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0332   -1.0921   -1.2185 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3840   -2.4073   -1.4539 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6525   -0.9636   -0.6147 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3503   -1.3690   -1.4920 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5011    3.0947   -0.5776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2747    1.6285   -1.4084 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7348    0.7412   -2.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2451   -0.2592    0.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9732   -1.7374    1.9156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8213   -2.0382    3.0188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8174   -0.9391    2.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4062    0.8826   -1.5199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8917    1.3993   -1.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5814    1.3593    0.7419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3288    2.7025    0.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1491    1.8762    2.8443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6740   -1.0668    0.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4139   -0.8524   -1.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1615   -0.4643   -2.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1740   -2.7219   -2.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6422   -1.4413    0.3576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0358   -1.4575   -2.3835 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  8  3  1  0
 19 10  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
 10 28  1  6
 12 29  1  6
 13 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  1
 16 34  1  0
 17 35  1  6
 18 36  1  0
 19 37  1  1
 20 38  1  0
M  END


  Mrv1652305271900282D          

 20 21  0  0  1  0            999 V2000
   12.1223   -7.4846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4078   -7.8971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8367   -7.8971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4078   -8.7221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5513   -9.1346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2644   -9.9596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8367   -8.7221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1223   -9.1346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9789  -10.3721    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.9789  -11.1971    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.6933  -11.6096    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.4078  -11.1971    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4078  -10.3721    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.2657   -8.7221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2644   -9.1346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2644  -11.6096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6933  -12.4346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1223  -11.6096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1223   -9.9596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6933   -9.9596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  2  0  0  0  0
  1  2  1  0  0  0  0
  2  4  2  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5 14  1  0  0  0  0
  5  7  1  0  0  0  0
  9  6  1  1  0  0  0
  6 15  1  0  0  0  0
  7  8  2  0  0  0  0
  8 19  1  0  0  0  0
  9 10  1  0  0  0  0
  9 20  1  0  0  0  0
 10 11  1  0  0  0  0
 10 16  1  6  0  0  0
 11 12  1  0  0  0  0
 11 17  1  1  0  0  0
 12 13  1  0  0  0  0
 12 18  1  6  0  0  0
 13 19  1  1  0  0  0
 13 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001377

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=C(CO)C=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C13H18O7/c14-5-7-3-1-2-4-8(7)19-13-12(18)11(17)10(16)9(6-15)20-13/h1-4,9-18H,5-6H2/t9-,10-,11+,12-,13-/m1/s1

> <INCHI_KEY>
NGFMICBWJRZIBI-UJPOAAIJSA-N

> <FORMULA>
C13H18O7

> <MOLECULAR_WEIGHT>
286.2778

> <EXACT_MASS>
286.10525293

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
27.889424057181387

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[2-(hydroxymethyl)phenoxy]oxane-3,4,5-triol

> <ALOGPS_LOGP>
-1.15

> <JCHEM_LOGP>
-1.3657373663333332

> <ALOGPS_LOGS>
-1.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.183713426774577

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.198710719721928

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9360965919196627

> <JCHEM_POLAR_SURFACE_AREA>
119.61000000000001

> <JCHEM_REFRACTIVITY>
66.9992

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.49e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
salicin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0003546
     RDKit          3D
Salicin
 38 39  0  0  0  0  0  0  0  0999 V2000
    4.1282    2.2867   -0.7564 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2311    1.2585   -1.1260 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1300    0.2825    0.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2592   -0.3349    0.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0675   -1.2045    1.5579 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8632   -1.4397    2.1536 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7493   -0.7496    1.5975 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8676    0.0761    0.5709 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8909    0.7614   -0.0551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4207    0.5469   -0.3831 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3423    1.1947    0.3243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6631    0.9453   -0.0672 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5271    1.6287    0.9849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1454    1.0994    2.2241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9878   -0.5248   -0.1562 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2904   -0.7010   -0.4929 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0332   -1.0921   -1.2185 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3840   -2.4073   -1.4539 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6525   -0.9636   -0.6147 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3503   -1.3690   -1.4920 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5011    3.0947   -0.5776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2747    1.6285   -1.4084 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7348    0.7412   -2.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2451   -0.2592    0.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9732   -1.7374    1.9156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8213   -2.0382    3.0188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8174   -0.9391    2.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4062    0.8826   -1.5199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8917    1.3993   -1.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5814    1.3593    0.7419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3288    2.7025    0.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1491    1.8762    2.8443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6740   -1.0668    0.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4139   -0.8524   -1.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1615   -0.4643   -2.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1740   -2.7219   -2.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6422   -1.4413    0.3576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0358   -1.4575   -2.3835 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  8  3  1  0
 19 10  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
 10 28  1  6
 12 29  1  6
 13 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  1
 16 34  1  0
 17 35  1  6
 18 36  1  0
 19 37  1  1
 20 38  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      22.628 -13.971   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.295 -14.741   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      23.962 -14.741   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.295 -16.281   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      25.296 -17.051   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.294 -18.591   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      23.962 -16.281   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      22.628 -17.051   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.627 -19.361   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.627 -20.901   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.961 -21.671   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.295 -20.901   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.295 -19.361   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      26.629 -16.281   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      17.294 -17.051   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      17.294 -21.671   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      19.961 -23.211   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      22.628 -21.671   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      22.628 -18.591   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      19.961 -18.591   0.000  0.00  0.00           O+0
CONECT    1    3    2                                                       
CONECT    2    1    4                                                       
CONECT    3    1    7                                                       
CONECT    4    2    8                                                       
CONECT    5   14    7                                                       
CONECT    6    9   15                                                       
CONECT    7    3    5    8                                                  
CONECT    8    4    7   19                                                  
CONECT    9    6   10   20                                                  
CONECT   10    9   11   16                                                  
CONECT   11   10   12   17                                                  
CONECT   12   11   13   18                                                  
CONECT   13   12   19   20                                                  
CONECT   14    5                                                            
CONECT   15    6                                                            
CONECT   16   10                                                            
CONECT   17   11                                                            
CONECT   18   12                                                            
CONECT   19    8   13                                                       
CONECT   20    9   13                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0003546
HETATM    1  O1  UNL     1       4.128   2.287  -0.756  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.231   1.259  -1.126  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.130   0.283   0.019  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.259  -0.335   0.478  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.068  -1.204   1.558  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.863  -1.440   2.154  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.749  -0.750   1.597  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.868   0.076   0.571  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.891   0.761  -0.055  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.421   0.547  -0.383  1.00  0.00           C  
HETATM   11  O3  UNL     1      -1.342   1.195   0.324  1.00  0.00           O  
HETATM   12  C9  UNL     1      -2.663   0.945  -0.067  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.527   1.629   0.985  1.00  0.00           C  
HETATM   14  O4  UNL     1      -3.145   1.099   2.224  1.00  0.00           O  
HETATM   15  C11 UNL     1      -2.988  -0.525  -0.156  1.00  0.00           C  
HETATM   16  O5  UNL     1      -4.290  -0.701  -0.493  1.00  0.00           O  
HETATM   17  C12 UNL     1      -2.033  -1.092  -1.219  1.00  0.00           C  
HETATM   18  O6  UNL     1      -2.384  -2.407  -1.454  1.00  0.00           O  
HETATM   19  C13 UNL     1      -0.652  -0.964  -0.615  1.00  0.00           C  
HETATM   20  O7  UNL     1       0.350  -1.369  -1.492  1.00  0.00           O  
HETATM   21  H1  UNL     1       3.501   3.095  -0.578  1.00  0.00           H  
HETATM   22  H2  UNL     1       2.275   1.628  -1.408  1.00  0.00           H  
HETATM   23  H3  UNL     1       3.735   0.741  -2.000  1.00  0.00           H  
HETATM   24  H4  UNL     1       5.245  -0.259   0.031  1.00  0.00           H  
HETATM   25  H5  UNL     1       4.973  -1.737   1.916  1.00  0.00           H  
HETATM   26  H6  UNL     1       2.821  -2.038   3.019  1.00  0.00           H  
HETATM   27  H7  UNL     1       0.817  -0.939   2.155  1.00  0.00           H  
HETATM   28  H8  UNL     1      -0.406   0.883  -1.520  1.00  0.00           H  
HETATM   29  H9  UNL     1      -2.892   1.399  -1.056  1.00  0.00           H  
HETATM   30  H10 UNL     1      -4.581   1.359   0.742  1.00  0.00           H  
HETATM   31  H11 UNL     1      -3.329   2.702   0.944  1.00  0.00           H  
HETATM   32  H12 UNL     1      -3.149   1.876   2.844  1.00  0.00           H  
HETATM   33  H13 UNL     1      -2.674  -1.067   0.785  1.00  0.00           H  
HETATM   34  H14 UNL     1      -4.414  -0.852  -1.446  1.00  0.00           H  
HETATM   35  H15 UNL     1      -2.161  -0.464  -2.129  1.00  0.00           H  
HETATM   36  H16 UNL     1      -2.174  -2.722  -2.365  1.00  0.00           H  
HETATM   37  H17 UNL     1      -0.642  -1.441   0.358  1.00  0.00           H  
HETATM   38  H18 UNL     1      -0.036  -1.458  -2.383  1.00  0.00           H  
CONECT    1    2   21
CONECT    2    3   22   23
CONECT    3    4    4    8
CONECT    4    5   24
CONECT    5    6    6   25
CONECT    6    7   26
CONECT    7    8    8   27
CONECT    8    9
CONECT    9   10
CONECT   10   11   19   28
CONECT   11   12
CONECT   12   13   15   29
CONECT   13   14   30   31
CONECT   14   32
CONECT   15   16   17   33
CONECT   16   34
CONECT   17   18   19   35
CONECT   18   36
CONECT   19   20   37
CONECT   20   38
END

HMDB0003546
     RDKit          3D
Salicin
 38 39  0  0  0  0  0  0  0  0999 V2000
    4.1282    2.2867   -0.7564 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2311    1.2585   -1.1260 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1300    0.2825    0.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2592   -0.3349    0.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0675   -1.2045    1.5579 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8632   -1.4397    2.1536 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7493   -0.7496    1.5975 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8676    0.0761    0.5709 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8909    0.7614   -0.0551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4207    0.5469   -0.3831 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3423    1.1947    0.3243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6631    0.9453   -0.0672 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5271    1.6287    0.9849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1454    1.0994    2.2241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9878   -0.5248   -0.1562 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2904   -0.7010   -0.4929 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0332   -1.0921   -1.2185 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3840   -2.4073   -1.4539 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6525   -0.9636   -0.6147 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3503   -1.3690   -1.4920 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5011    3.0947   -0.5776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2747    1.6285   -1.4084 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7348    0.7412   -2.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2451   -0.2592    0.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9732   -1.7374    1.9156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8213   -2.0382    3.0188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8174   -0.9391    2.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4062    0.8826   -1.5199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8917    1.3993   -1.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5814    1.3593    0.7419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3288    2.7025    0.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1491    1.8762    2.8443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6740   -1.0668    0.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4139   -0.8524   -1.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1615   -0.4643   -2.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1740   -2.7219   -2.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6422   -1.4413    0.3576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0358   -1.4575   -2.3835 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  8  3  1  0
 19 10  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
 10 28  1  6
 12 29  1  6
 13 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  1
 16 34  1  0
 17 35  1  6
 18 36  1  0
 19 37  1  1
 20 38  1  0
M  END

View in JSmol

Synonyms

Value	Source
2(Hydroxymethyl)phenyl-beta-D-glucopyranoside	ChEBI
2-(Hydroxymethyl)phenyl-beta-D-glucopyranoside	ChEBI
2-(Hydroxymethyl)phenyl-O-beta-D-glucopyranoside	ChEBI
D-(-)-Salicin	ChEBI
O-(Hydroxymethyl)phenyl beta-D-glucopyranoside	ChEBI
Salicoside	ChEBI
Salicyl alcohol glucoside	ChEBI
Saligenin beta-D-glucopyranoside	ChEBI
2(Hydroxymethyl)phenyl-b-D-glucopyranoside	Generator
2(Hydroxymethyl)phenyl-β-D-glucopyranoside	Generator
2-(Hydroxymethyl)phenyl-b-D-glucopyranoside	Generator
2-(Hydroxymethyl)phenyl-β-D-glucopyranoside	Generator
2-(Hydroxymethyl)phenyl-O-b-D-glucopyranoside	Generator
2-(Hydroxymethyl)phenyl-O-β-D-glucopyranoside	Generator
O-(Hydroxymethyl)phenyl b-D-glucopyranoside	Generator
O-(Hydroxymethyl)phenyl β-D-glucopyranoside	Generator
Saligenin b-D-glucopyranoside	Generator
Saligenin β-D-glucopyranoside	Generator
2-(Hydroxymethyl)phenyl hexopyranoside	HMDB
D-Salicin	HMDB
delta-Salicin	HMDB
Salicine	HMDB
Saligenin beta-delta-glucopyranoside	HMDB
Saligenin-b-D-glucopyranoside	HMDB
Saligenin-beta-D-glucopyranoside	HMDB
Saligenin-beta-delta-glucopyranoside	HMDB

Chemical Formula

C₁₃H₁₈O₇

Average Mass

286.2778 Da

Monoisotopic Mass

286.10525 Da

IUPAC Name

(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[2-(hydroxymethyl)phenoxy]oxane-3,4,5-triol

Traditional Name

salicin

CAS Registry Number

138-52-3

SMILES

OC[C@H]1O[C@@H](OC2=C(CO)C=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C13H18O7/c14-5-7-3-1-2-4-8(7)19-13-12(18)11(17)10(16)9(6-15)20-13/h1-4,9-18H,5-6H2/t9-,10-,11+,12-,13-/m1/s1

InChI Key

NGFMICBWJRZIBI-UJPOAAIJSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.133705802, CD₃OD, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Aegle marmelos	LOTUS Database	35616633
Alangium chinense	KNApSAcK Database	22123792
Alangium platanifolium	LOTUS Database	35616633
Apis cerana	LOTUS Database	35616633
Filipendula ulmaria	LOTUS Database	35616633
Gardenia jasminoides	LOTUS Database	35616633
Imperata cylindrica	LOTUS Database	35616633
Itoa orientalis	LOTUS Database	35616633
Laguncularia racemosa	LOTUS Database	35616633
Populus adenopoda	KNApSAcK Database	22123792
Populus alba	KNApSAcK Database	22123792
Populus alba var.pyramdalis	KNApSAcK Database	22123792
Populus balsamifera	KNApSAcK Database	22123792
Populus beijingensis	KNApSAcK Database	22123792
Populus canadensis	KNApSAcK Database	22123792
Populus candicans	KNApSAcK Database	22123792
Populus cathayana	KNApSAcK Database	22123792
Populus davidiana	KNApSAcK Database	22123792
Populus deltoides	KNApSAcK Database	22123792
Populus euphratica	LOTUS Database	35616633
Populus hopeiensis	KNApSAcK Database	22123792
Populus koreana	KNApSAcK Database	22123792
Populus lasiocarpa	KNApSAcK Database	22123792
Populus nigra	LOTUS Database	35616633
Populus nigra var.thevestina	KNApSAcK Database	22123792
Populus pseudo-simonii	KNApSAcK Database	22123792
Populus sieboldii	KNApSAcK Database	22123792
Populus spp.	KNApSAcK Database	22123792
Populus tomentosa	KNApSAcK Database	22123792
Populus tremula	KNApSAcK Database	22123792
Populus tremuloides	KNApSAcK Database	22123792
Populus trichocarpa	KNApSAcK Database	22123792
Populus ussuriensis	KNApSAcK Database	22123792
Populus xiaohei	KNApSAcK Database	22123792
Salix acmophylla	Plant	KNApSAcK
Salix alba	KNApSAcK Database	22123792
Salix americana	KNApSAcK Database	22123792
Salix arbusculoides	KNApSAcK Database	22123792
Salix aurita	KNApSAcK Database	22123792
Salix babylonica	KNApSAcK Database	22123792
Salix callicarpaea	KNApSAcK Database	22123792
Salix calodendron	KNApSAcK Database	22123792
Salix caprea	KNApSAcK Database	22123792
Salix chaenomeloides	KNApSAcK Database	22123792
Salix cinerea	KNApSAcK Database	22123792
Salix cv. aquatica	KNApSAcK Database	22123792
Salix daphnoides	KNApSAcK Database	22123792
Salix decipiens	KNApSAcK Database	22123792
Salix elbursensis	KNApSAcK Database	22123792
Salix fragilis	KNApSAcK Database	22123792
Salix gracilistyla	LOTUS Database	35616633
Salix hastata	LOTUS Database	35616633
Salix herbacea	KNApSAcK Database	22123792
Salix incana	KNApSAcK Database	22123792
Salix lapponum	KNApSAcK Database	22123792
Salix lasiolepis	LOTUS Database	35616633
Salix martiana	KNApSAcK Database	22123792
Salix myrsinifolia	KNApSAcK Database	22123792
Salix nigricans	KNApSAcK Database	22123792
Salix pentandra	KNApSAcK Database	22123792
Salix pentandroides	KNApSAcK Database	22123792
Salix petiolaris	KNApSAcK Database	22123792
Salix phylicifolia	KNApSAcK Database	22123792
Salix purpurea	KNApSAcK Database	22123792
Salix repens	KNApSAcK Database	22123792
Salix schwerinii	KNApSAcK Database	22123792
Salix songorica	KNApSAcK Database	22123792
Salix spp.	KNApSAcK Database	22123792
Salix tetrasperma	LOTUS Database	35616633
Salix triandra	KNApSAcK Database	22123792
Salix viminalis	KNApSAcK Database	22123792
Salix x geminata	KNApSAcK Database	22123792
Salix x pendulina	LOTUS Database	35616633
Salix x rubra	KNApSAcK Database	22123792
Triticum aestivum	KNApSAcK Database	22123792
Viburnum prunifolium	KNApSAcK Database	22123792
Viburnum rhytidophyllum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
O-glycosyl compound
Phenoxy compound
Benzyl alcohol
Phenol ether
Monocyclic benzene moiety
Monosaccharide
Oxane
Benzenoid
Secondary alcohol
Polyol
Organoheterocyclic compound
Oxacycle
Acetal
Alcohol
Hydrocarbon derivative
Primary alcohol
Aromatic alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

benzyl alcohols (CHEBI:17814 )
aromatic primary alcohol (CHEBI:17814 )
aryl beta-D-glucoside (CHEBI:17814 )
Phenylpropanoids (C01451 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	207 °C	Not Available
Boiling Point	549.09 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	40 mg/mL at 25 °C	Not Available
LogP	-1.22	Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).

Predicted Properties

Property	Value	Source
Water Solubility	24.9 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-1.4	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	119.61 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	67 m³·mol⁻¹	ChemAxon
Polarizability	27.89 Å³	ChemAxon
Number of Rings	2	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

HMDB0003546

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Salicin

METLIN ID

6948

PubChem Compound

439503

PDB ID

Not Available

ChEBI ID

17814

Good Scents ID

rw1108911

References

General References

Sakurai M, Ohsako M, Nagano M, Nakamura C, Tsuzuki O, Ichikawa M, Matsumoto Y: [Effect of human serum albumin on transport of drugs through human erythrocyte membranes]. Yakugaku Zasshi. 1996 Aug;116(8):630-8. [PubMed:8831264 ]
Mahdi JG, Mahdi AJ, Mahdi AJ, Bowen ID: The historical analysis of aspirin discovery, its relation to the willow tree and antiproliferative and anticancer potential. Cell Prolif. 2006 Apr;39(2):147-55. [PubMed:16542349 ]
Sadatsune T, Moreno G: [Contribution to the study of the haemolytic streptococci isolated from dogs (author's transl)]. Arq Inst Biol (Sao Paulo). 1975;42:257-64. [PubMed:1236057 ]
Brenner DJ, Hickman-Brenner FW, Holmes B, Hawkey PM, Penner JL, Grimont PA, O'Hara CM: Replacement of NCTC 4175, the current type strain of Proteus vulgaris, with ATCC 29905. Request for an opinion. Int J Syst Bacteriol. 1995 Oct;45(4):870-1. [PubMed:7547312 ]
Akao T, Yoshino T, Kobashi K, Hattori M: Evaluation of salicin as an antipyretic prodrug that does not cause gastric injury. Planta Med. 2002 Aug;68(8):714-8. doi: 10.1055/s-2002-33792. [PubMed:12221594 ]

Showing NP-Card for Salicin (NP0001377)

MOL for NP0001377 (Salicin)

3D MOL for NP0001377 (Salicin)

3D SDF for NP0001377 (Salicin)

3D-SDF for NP0001377 (Salicin)

PDB for NP0001377 (Salicin)

3D PDB for NP0001377 (Salicin)

SMILES for NP0001377 (Salicin)

INCHI for NP0001377 (Salicin)

Structure for NP0001377 (Salicin)

3D Structure for NP0001377 (Salicin)