NP-MRD: Showing NP-Card for Cofaryloside (NP0048149)

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Record Information

Version

2.0

Created at

2022-03-17 20:51:53 UTC

Updated at

2022-03-17 20:51:53 UTC

NP-MRD ID

NP0048149

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cofaryloside

Description

Cofaryloside belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. Cofaryloside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, cofaryloside has been detected, but not quantified in, coffee and coffee products. This could make cofaryloside a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061308142D          

 36 40  0  0  0  0            999 V2000
    3.7830    2.9327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5305    1.7392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3553    0.7609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1624    0.0148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7316    2.6344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6225    1.5414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5458    0.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9122    2.4784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9943    0.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4240    0.9109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3661    2.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7383    2.0343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5355    0.9240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5599    0.6390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6438    2.6444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2706    2.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6279    3.4693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9056    3.8679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1992    3.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2152    2.6169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7865    2.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0801    2.1631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0034    1.2236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5716    1.6964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1409    1.3964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1837    1.0614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0725    2.6720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2827    1.2737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3343    3.8955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8897    4.6928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4769    3.8403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7706    3.4141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3993    2.0199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7448    0.3923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9375    2.2182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5088    2.1906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  3  1  0  0  0  0
  7  3  1  0  0  0  0
  8  5  1  0  0  0  0
  9  4  1  0  0  0  0
 14  4  1  0  0  0  0
 14 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16  5  1  0  0  0  0
 17 15  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 22  1  1  0  0  0  0
 22  6  1  0  0  0  0
 22 16  1  0  0  0  0
 22 21  1  0  0  0  0
 23  2  1  0  0  0  0
 23  7  1  0  0  0  0
 23 16  1  0  0  0  0
 24  8  1  0  0  0  0
 24 10  1  0  0  0  0
 24 12  1  0  0  0  0
 25 12  1  0  0  0  0
 25 13  1  0  0  0  0
 25 14  1  0  0  0  0
 26  9  1  0  0  0  0
 26 23  1  0  0  0  0
 26 24  1  0  0  0  0
 27 11  1  0  0  0  0
 28 13  1  0  0  0  0
 29 17  1  0  0  0  0
 30 18  1  0  0  0  0
 31 19  1  0  0  0  0
 32 21  2  0  0  0  0
 33 25  1  0  0  0  0
 34 26  1  0  0  0  0
 35 15  1  0  0  0  0
 35 20  1  0  0  0  0
 36 20  1  0  0  0  0
 36 21  1  0  0  0  0
M  END


  Mrv0541 05061308142D          

 36 40  0  0  0  0            999 V2000
    3.7830    2.9327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5305    1.7392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3553    0.7609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1624    0.0148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7316    2.6344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6225    1.5414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5458    0.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9122    2.4784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9943    0.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4240    0.9109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3661    2.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7383    2.0343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5355    0.9240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5599    0.6390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6438    2.6444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2706    2.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6279    3.4693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9056    3.8679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1992    3.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2152    2.6169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7865    2.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0801    2.1631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0034    1.2236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5716    1.6964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1409    1.3964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1837    1.0614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0725    2.6720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2827    1.2737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3343    3.8955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8897    4.6928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4769    3.8403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7706    3.4141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3993    2.0199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7448    0.3923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9375    2.2182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5088    2.1906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  3  1  0  0  0  0
  7  3  1  0  0  0  0
  8  5  1  0  0  0  0
  9  4  1  0  0  0  0
 14  4  1  0  0  0  0
 14 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16  5  1  0  0  0  0
 17 15  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 22  1  1  0  0  0  0
 22  6  1  0  0  0  0
 22 16  1  0  0  0  0
 22 21  1  0  0  0  0
 23  2  1  0  0  0  0
 23  7  1  0  0  0  0
 23 16  1  0  0  0  0
 24  8  1  0  0  0  0
 24 10  1  0  0  0  0
 24 12  1  0  0  0  0
 25 12  1  0  0  0  0
 25 13  1  0  0  0  0
 25 14  1  0  0  0  0
 26  9  1  0  0  0  0
 26 23  1  0  0  0  0
 26 24  1  0  0  0  0
 27 11  1  0  0  0  0
 28 13  1  0  0  0  0
 29 17  1  0  0  0  0
 30 18  1  0  0  0  0
 31 19  1  0  0  0  0
 32 21  2  0  0  0  0
 33 25  1  0  0  0  0
 34 26  1  0  0  0  0
 35 15  1  0  0  0  0
 35 20  1  0  0  0  0
 36 20  1  0  0  0  0
 36 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048149

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(CCCC2(C)C1CCC13CC(CCC21O)C(O)(CO)C3)C(=O)OC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H42O10/c1-22(21(32)36-20-19(31)18(30)17(29)15(11-27)35-20)6-3-7-23(2)16(22)5-8-24-10-14(4-9-26(23,24)34)25(33,12-24)13-28/h14-20,27-31,33-34H,3-13H2,1-2H3

> <INCHI_KEY>
VEZJUFUSLIUNOY-UHFFFAOYSA-N

> <FORMULA>
C26H42O10

> <MOLECULAR_WEIGHT>
514.6057

> <EXACT_MASS>
514.277797564

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
54.64686598390921

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 10,14-dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate

> <ALOGPS_LOGP>
-0.36

> <JCHEM_LOGP>
-0.47810101466666804

> <ALOGPS_LOGS>
-2.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.045003123497768

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.175992599850977

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981093680169468

> <JCHEM_POLAR_SURFACE_AREA>
177.13999999999996

> <JCHEM_REFRACTIVITY>
124.61719999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.15e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 10,14-dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       7.062   5.474   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.724   3.247   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.130   1.420   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.170   0.028   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.099   4.918   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.629   2.877   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.619   1.124   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.569   4.626   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.723   0.398   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.658   1.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.617   4.192   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.378   3.797   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.000   1.725   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.045   1.193   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.268   4.936   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.105   3.741   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.239   6.476   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.890   7.220   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.572   6.425   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.602   4.885   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.935   4.833   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.616   4.038   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.606   2.284   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.934   3.167   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.263   2.607   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.076   1.981   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      16.935   4.988   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -2.394   2.378   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      15.557   7.272   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      12.861   8.760   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      10.224   7.169   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       8.905   6.373   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -0.745   3.770   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       5.124   0.732   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      12.950   4.141   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      10.283   4.089   0.000  0.00  0.00           O+0
CONECT    1   22                                                            
CONECT    2   23                                                            
CONECT    3    6    7                                                       
CONECT    4    9   14                                                       
CONECT    5    8   16                                                       
CONECT    6    3   22                                                       
CONECT    7    3   23                                                       
CONECT    8    5   24                                                       
CONECT    9    4   26                                                       
CONECT   10   14   24                                                       
CONECT   11   15   27                                                       
CONECT   12   24   25                                                       
CONECT   13   25   28                                                       
CONECT   14    4   10   25                                                  
CONECT   15   11   17   35                                                  
CONECT   16    5   22   23                                                  
CONECT   17   15   18   29                                                  
CONECT   18   17   19   30                                                  
CONECT   19   18   20   31                                                  
CONECT   20   19   35   36                                                  
CONECT   21   22   32   36                                                  
CONECT   22    1    6   16   21                                             
CONECT   23    2    7   16   26                                             
CONECT   24    8   10   12   26                                             
CONECT   25   12   13   14   33                                             
CONECT   26    9   23   24   34                                             
CONECT   27   11                                                            
CONECT   28   13                                                            
CONECT   29   17                                                            
CONECT   30   18                                                            
CONECT   31   19                                                            
CONECT   32   21                                                            
CONECT   33   25                                                            
CONECT   34   26                                                            
CONECT   35   15   20                                                       
CONECT   36   20   21                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
Lithocholic acid, methyl ester	HMDB
Methyl 3alpha-hydroxy-5beta-cholan-24-Oate	HMDB
Methyl lithocholate	HMDB
3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl 10,14-dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid	Generator

Chemical Formula

C₂₆H₄₂O₁₀

Average Mass

514.6057 Da

Monoisotopic Mass

514.27780 Da

IUPAC Name

3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 10,14-dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate

Traditional Name

3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 10,14-dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate

CAS Registry Number

63558-43-0

SMILES

CC1(CCCC2(C)C1CCC13CC(CCC21O)C(O)(CO)C3)C(=O)OC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C26H42O10/c1-22(21(32)36-20-19(31)18(30)17(29)15(11-27)35-20)6-3-7-23(2)16(22)5-8-24-10-14(4-9-26(23,24)34)25(33,12-24)13-28/h14-20,27-31,33-34H,3-13H2,1-2H3

InChI Key

VEZJUFUSLIUNOY-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Coffea arabica L.	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephora	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Diterpene glycosides

Alternative Parents

Substituents

Diterpene glycoside
Diterpenoid
Kaurane diterpenoid
Hexose monosaccharide
Monosaccharide
Oxane
Cyclic alcohol
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Polyol
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Acetal
Carboxylic acid derivative
Primary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	-0.36	ALOGPS
logP	-0.48	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	12.18	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	177.14 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	124.62 m³·mol⁻¹	ChemAxon
Polarizability	54.65 Å³	ChemAxon
Number of Rings	5	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

HMDB0035096

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013725

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

131751664

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Cofaryloside (NP0048149)

MOL for NP0048149 (Cofaryloside)

3D MOL for NP0048149 (Cofaryloside)

3D SDF for NP0048149 (Cofaryloside)

3D-SDF for NP0048149 (Cofaryloside)

PDB for NP0048149 (Cofaryloside)

3D PDB for NP0048149 (Cofaryloside)

SMILES for NP0048149 (Cofaryloside)

INCHI for NP0048149 (Cofaryloside)

Structure for NP0048149 (Cofaryloside)

3D Structure for NP0048149 (Cofaryloside)