NP-MRD: Showing NP-Card for Trigoneoside Xa (NP0048522)

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Record Information

Version

2.0

Created at

2022-03-17 20:57:47 UTC

Updated at

2022-03-17 20:57:47 UTC

NP-MRD ID

NP0048522

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Trigoneoside Xa

Description

Xi-Linalool 3-[rhamnosyl-(1->6)-glucoside] belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. Xi-Linalool 3-[rhamnosyl-(1->6)-glucoside] is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, xi-Linalool 3-[rhamnosyl-(1->6)-glucoside] has been detected, but not quantified in, a few different foods, such as alcoholic beverages, common grapes, and fruits. Trigoneoside Xa is found in Trigonella foenum and Trigonella foenum-graecum L. . This could make XI-linalool 3-[rhamnosyl-(1->6)-glucoside] a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241211372D          

 64 71  0  0  0  0            999 V2000
   -4.2296   -0.5306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0901   -1.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 58 60  1  0  0  0  0
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M  END


  Mrv0541 02241211372D          

 64 71  0  0  0  0            999 V2000
   -4.2296   -0.5306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2296   -1.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5159   -1.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8037   -1.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5159   -0.1196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0901   -1.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3777   -1.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 60 61  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048522

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC1(O)OC2CC3C4CCC5CC(OC6OC(CO)C(O)C(O)C6OC6OC(C)C(O)C(O)C6O)C(O)CC5(C)C4CCC3(C)C2C1C)COC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C45H76O19/c1-18(17-58-40-37(55)35(53)32(50)28(15-46)61-40)8-11-45(57)19(2)30-27(64-45)13-24-22-7-6-21-12-26(25(48)14-44(21,5)23(22)9-10-43(24,30)4)60-42-39(36(54)33(51)29(16-47)62-42)63-41-38(56)34(52)31(49)20(3)59-41/h18-42,46-57H,6-17H2,1-5H3

> <INCHI_KEY>
WROHFEWGWYQNPP-UHFFFAOYSA-N

> <FORMULA>
C45H76O19

> <MOLECULAR_WEIGHT>
921.0735

> <EXACT_MASS>
920.49808025

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
97.29641908212221

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2-{[6,15-dihydroxy-7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan-16-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl)oxy]-6-methyloxane-3,4,5-triol

> <ALOGPS_LOGP>
-0.74

> <JCHEM_LOGP>
-1.1693192143333324

> <ALOGPS_LOGS>
-3.03

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.044152972131553

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.557688898592087

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6483772987566265

> <JCHEM_POLAR_SURFACE_AREA>
307.37

> <JCHEM_REFRACTIVITY>
219.98370000000008

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.67e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2-{[6,15-dihydroxy-7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan-16-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl)oxy]-6-methyloxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -7.895  -0.990   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.895  -2.531   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.563  -3.301   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.234  -2.531   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.234  -0.990   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.563  -0.223   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.902  -3.301   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.572  -2.531   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.572  -0.990   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.902  -0.223   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.245  -0.223   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.245   1.309   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.572   2.074   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.902   1.309   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.211  -0.696   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.106   0.544   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.211   1.779   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.554   1.014   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.554   2.536   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.106   3.006   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.888   3.306   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.223   2.536   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.558   3.306   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.893   2.536   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.227   3.306   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.558   4.846   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.631   4.471   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.554   4.076   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.245   2.849   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.234   0.550   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -9.227  -0.221   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -9.230  -3.301   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -9.230  -4.841   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0     -10.562  -5.611   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0     -10.562  -7.151   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -9.230  -7.923   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -7.898  -7.151   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -7.898  -5.611   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0     -11.897  -7.921   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0     -11.897  -9.461   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -9.230  -9.464   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      -6.563  -4.841   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -5.228  -5.611   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -5.228  -7.151   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -3.896  -7.921   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -2.567  -7.151   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -2.567  -5.611   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      -3.896  -4.843   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      -1.232  -4.841   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      -1.232  -7.921   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      -3.896  -9.461   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      -5.228  -8.691   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      -7.898  -8.691   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0       9.227   4.846   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      10.562   5.613   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      10.562   7.153   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       9.227   7.924   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       7.893   7.153   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0       7.893   5.613   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0       6.558   7.924   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0       5.223   7.153   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0       9.227   9.464   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0      11.897   7.924   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0      11.894   4.843   0.000  0.00  0.00           O+0
CONECT    1    2    6   31                                                  
CONECT    2    1    3   32                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   30                                             
CONECT    6    1    5                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    5    9   14                                                  
CONECT   11    9   12   15                                                  
CONECT   12   11   13   17   29                                             
CONECT   13   12   14                                                       
CONECT   14   10   13                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   12   16   20                                                  
CONECT   18   16   19                                                       
CONECT   19   18   20   21   28                                             
CONECT   20   17   19   27                                                  
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24   54                                                       
CONECT   26   23                                                            
CONECT   27   20                                                            
CONECT   28   19                                                            
CONECT   29   12                                                            
CONECT   30    5                                                            
CONECT   31    1                                                            
CONECT   32    2   33                                                       
CONECT   33   32   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   39                                                  
CONECT   36   35   37   41                                                  
CONECT   37   36   38   53                                                  
CONECT   38   33   37   42                                                  
CONECT   39   35   40                                                       
CONECT   40   39                                                            
CONECT   41   36                                                            
CONECT   42   38   43                                                       
CONECT   43   42   44   48                                                  
CONECT   44   43   45   52                                                  
CONECT   45   44   46   51                                                  
CONECT   46   45   47   50                                                  
CONECT   47   46   48   49                                                  
CONECT   48   43   47                                                       
CONECT   49   47                                                            
CONECT   50   46                                                            
CONECT   51   45                                                            
CONECT   52   44                                                            
CONECT   53   37                                                            
CONECT   54   25   55   59                                                  
CONECT   55   54   56   64                                                  
CONECT   56   55   57   63                                                  
CONECT   57   56   58   62                                                  
CONECT   58   57   59   60                                                  
CONECT   59   54   58                                                       
CONECT   60   58   61                                                       
CONECT   61   60                                                            
CONECT   62   57                                                            
CONECT   63   56                                                            
CONECT   64   55                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  142    0
END

View in JSmol

Synonyms

Value	Source
(-)-Trigoneoside XB	HMDB

Chemical Formula

C₄₅H₇₆O₁₉

Average Mass

921.0735 Da

Monoisotopic Mass

920.49808 Da

IUPAC Name

2-[(2-{[6,15-dihydroxy-7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan-16-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl)oxy]-6-methyloxane-3,4,5-triol

Traditional Name

CAS Registry Number

290347-51-2

SMILES

CC(CCC1(O)OC2CC3C4CCC5CC(OC6OC(CO)C(O)C(O)C6OC6OC(C)C(O)C(O)C6O)C(O)CC5(C)C4CCC3(C)C2C1C)COC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C45H76O19/c1-18(17-58-40-37(55)35(53)32(50)28(15-46)61-40)8-11-45(57)19(2)30-27(64-45)13-24-22-7-6-21-12-26(25(48)14-44(21,5)23(22)9-10-43(24,30)4)60-42-39(36(54)33(51)29(16-47)62-42)63-41-38(56)34(52)31(49)20(3)59-41/h18-42,46-57H,6-17H2,1-5H3

InChI Key

WROHFEWGWYQNPP-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Trigonella foenum	Plant	KNApSAcK
Trigonella foenum-graecum	FooDB	KNAPSACK
Trigonella foenum-graecum L.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Disaccharide
Glycosyl compound
O-glycosyl compound
Monoterpenoid
Monocyclic monoterpenoid
Oxane
Secondary alcohol
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
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	-0.74	ALOGPS
logP	-1.2	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	11.56	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	307.37 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	219.98 m³·mol⁻¹	ChemAxon
Polarizability	97.3 Å³	ChemAxon
Number of Rings	8	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

HMDB0030422

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002286

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

15624187

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Trigoneoside Xa (NP0048522)

MOL for NP0048522 (Trigoneoside Xa)

3D MOL for NP0048522 (Trigoneoside Xa)

3D SDF for NP0048522 (Trigoneoside Xa)

3D-SDF for NP0048522 (Trigoneoside Xa)

PDB for NP0048522 (Trigoneoside Xa)

3D PDB for NP0048522 (Trigoneoside Xa)

SMILES for NP0048522 (Trigoneoside Xa)

INCHI for NP0048522 (Trigoneoside Xa)

Structure for NP0048522 (Trigoneoside Xa)

3D Structure for NP0048522 (Trigoneoside Xa)