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Showing NP-Card for Isopentyl gentiobioside (NP0049866)

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Record Information
Version2.0
Created at2022-03-17 21:19:23 UTC
Updated at2022-03-17 21:19:23 UTC
NP-MRD IDNP0049866
Secondary Accession NumbersNone
Natural Product Identification
Common NameIsopentyl gentiobioside
DescriptionIsopentyl gentiobioside 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. Isopentyl gentiobioside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Isopentyl gentiobioside has been detected, but not quantified in, garden tomato. This could make isopentyl gentiobioside a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0049866 (Isopentyl gentiobioside)


  Mrv0541 05061312432D          

 28 29  0  0  0  0            999 V2000
    3.5724    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  7  1  1  0  0  0  0
  7  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14 13  1  0  0  0  0
 15 12  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 18  5  1  0  0  0  0
 19 10  1  0  0  0  0
 20 11  1  0  0  0  0
 21 12  1  0  0  0  0
 22 13  1  0  0  0  0
 23 14  1  0  0  0  0
 24 15  1  0  0  0  0
 25  4  1  0  0  0  0
 25 16  1  0  0  0  0
 26  6  1  0  0  0  0
 26 17  1  0  0  0  0
 27  8  1  0  0  0  0
 27 17  1  0  0  0  0
 28  9  1  0  0  0  0
 28 16  1  0  0  0  0
M  END
Download

3D MOL for NP0049866 (Isopentyl gentiobioside)

Download
3D SDF for NP0049866 (Isopentyl gentiobioside)

  Mrv0541 05061312432D          

 28 29  0  0  0  0            999 V2000
    3.5724    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  7  1  1  0  0  0  0
  7  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14 13  1  0  0  0  0
 15 12  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 18  5  1  0  0  0  0
 19 10  1  0  0  0  0
 20 11  1  0  0  0  0
 21 12  1  0  0  0  0
 22 13  1  0  0  0  0
 23 14  1  0  0  0  0
 24 15  1  0  0  0  0
 25  4  1  0  0  0  0
 25 16  1  0  0  0  0
 26  6  1  0  0  0  0
 26 17  1  0  0  0  0
 27  8  1  0  0  0  0
 27 17  1  0  0  0  0
 28  9  1  0  0  0  0
 28 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049866

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CCOC1OC(COC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C17H32O11/c1-7(2)3-4-25-16-14(23)13(22)11(20)9(28-16)6-26-17-15(24)12(21)10(19)8(5-18)27-17/h7-24H,3-6H2,1-2H3

> <INCHI_KEY>
PPIXDGFHKZNFOD-UHFFFAOYSA-N

> <FORMULA>
C17H32O11

> <MOLECULAR_WEIGHT>
412.4294

> <EXACT_MASS>
412.194461866

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
41.896170001868725

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(3-methylbutoxy)-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-1.75

> <JCHEM_LOGP>
-2.449330249

> <ALOGPS_LOGS>
-0.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.43298349659634

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.910765605146338

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083422322401

> <JCHEM_POLAR_SURFACE_AREA>
178.52999999999997

> <JCHEM_REFRACTIVITY>
91.5101

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.25e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3-methylbutoxy)-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0049866 (Isopentyl gentiobioside)
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PDB for NP0049866 (Isopentyl gentiobioside)
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       6.668   5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.668  11.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001   5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.668  10.010   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -8.002   9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -8.002   7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.335   7.700   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -8.002  12.320   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -9.336  10.010   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -9.336   6.930   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.334   0.770   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -6.668   5.390   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       1.334   5.390   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -4.001   6.930   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -5.335   9.240   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -1.334   5.390   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    7                                                            
CONECT    3    4    7                                                       
CONECT    4    3   25                                                       
CONECT    5    8   18                                                       
CONECT    6    9   26                                                       
CONECT    7    1    2    3                                                  
CONECT    8    5   10   27                                                  
CONECT    9    6   11   28                                                  
CONECT   10    8   12   19                                                  
CONECT   11    9   13   20                                                  
CONECT   12   10   15   21                                                  
CONECT   13   11   14   22                                                  
CONECT   14   13   16   23                                                  
CONECT   15   12   17   24                                                  
CONECT   16   14   25   28                                                  
CONECT   17   15   26   27                                                  
CONECT   18    5                                                            
CONECT   19   10                                                            
CONECT   20   11                                                            
CONECT   21   12                                                            
CONECT   22   13                                                            
CONECT   23   14                                                            
CONECT   24   15                                                            
CONECT   25    4   16                                                       
CONECT   26    6   17                                                       
CONECT   27    8   17                                                       
CONECT   28    9   16                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

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3D PDB for NP0049866 (Isopentyl gentiobioside)
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SMILES for NP0049866 (Isopentyl gentiobioside)
CC(C)CCOC1OC(COC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O
Download
INCHI for NP0049866 (Isopentyl gentiobioside)
InChI=1S/C17H32O11/c1-7(2)3-4-25-16-14(23)13(22)11(20)9(28-16)6-26-17-15(24)12(21)10(19)8(5-18)27-17/h7-24H,3-6H2,1-2H3
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SynonymsNot Available
Chemical FormulaC17H32O11
Average Mass412.4294 Da
Monoisotopic Mass412.19446 Da
IUPAC Name2-(3-methylbutoxy)-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-3,4,5-triol
Traditional Name2-(3-methylbutoxy)-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-3,4,5-triol
CAS Registry Number178275-89-3
SMILES
CC(C)CCOC1OC(COC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O
InChI Identifier
InChI=1S/C17H32O11/c1-7(2)3-4-25-16-14(23)13(22)11(20)9(28-16)6-26-17-15(24)12(21)10(19)8(5-18)27-17/h7-24H,3-6H2,1-2H3
InChI KeyPPIXDGFHKZNFOD-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Solanum lycopersicumFooDB
    • 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 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.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty acyl glycosides  
Direct ParentFatty acyl glycosides of mono- and disaccharides  
Alternative Parents
Substituents
  • Fatty acyl glycoside of mono- or disaccharide
    • 

  • Alkyl glycoside
    • 

  • Disaccharide
    • 

  • Glycosyl compound
    • 

  • O-glycosyl compound
    • 

  • Oxane
    • 

  • Secondary alcohol
    • 

  • Acetal
    • 

  • Organoheterocyclic compound
    • 

  • Oxacycle
    • 

  • Polyol
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Alcohol
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.8ALOGPS
logP-2.4ChemAxon
logS-0.76ALOGPS
pKa (Strongest Acidic)11.91ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area178.53 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity91.51 m³·mol⁻¹ChemAxon
Polarizability41.9 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0041512  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021486  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131753153  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References