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Showing NP-Card for Glucinol (NP0049353)

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Record Information
Version2.0
Created at2022-03-17 21:11:08 UTC
Updated at2022-03-17 21:11:08 UTC
NP-MRD IDNP0049353
Secondary Accession NumbersNone
Natural Product Identification
Common NameGlucinol
DescriptionGlucinol belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. Glucinol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Glucinol has been detected, but not quantified in, anises and potato. This could make glucinol a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0049353 (Glucinol)


  Mrv0541 02241209362D          

 23 24  0  0  1  0            999 V2000
   -0.5783    0.3168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2467    0.3168    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6592   -0.3977    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2467   -1.1122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4842   -0.3977    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8967   -1.1122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8967    0.3168    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7217    0.3168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4842    1.0313    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8967    1.7457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6592    1.0313    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2467    3.1747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1658    3.8891    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9908    3.8891    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4033    3.1747    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9908    2.4602    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1658    2.4602    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2467    1.7457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4033    1.7457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2283    3.1747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4033    4.6036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2467    4.6036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1658    5.3181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
  2 11  1  0  0  0  0
 11 18  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  1  0  0  0
 16 19  1  6  0  0  0
 15 20  1  1  0  0  0
 14 21  1  6  0  0  0
 13 22  1  1  0  0  0
 22 23  1  0  0  0  0
M  END
Download

3D MOL for NP0049353 (Glucinol)

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3D SDF for NP0049353 (Glucinol)

  Mrv0541 02241209362D          

 23 24  0  0  1  0            999 V2000
   -0.5783    0.3168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2467    0.3168    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6592   -0.3977    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2467   -1.1122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4842   -0.3977    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8967   -1.1122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8967    0.3168    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7217    0.3168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4842    1.0313    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8967    1.7457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6592    1.0313    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2467    3.1747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1658    3.8891    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9908    3.8891    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4033    3.1747    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9908    2.4602    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1658    2.4602    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2467    1.7457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4033    1.7457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2283    3.1747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4033    4.6036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2467    4.6036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1658    5.3181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
  2 11  1  0  0  0  0
 11 18  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  1  0  0  0
 16 19  1  6  0  0  0
 15 20  1  1  0  0  0
 14 21  1  6  0  0  0
 13 22  1  1  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049353

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1O[C@@H](O[C@H]2[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C12H22O11/c1-21-11-8(19)5(16)9(20)12(23-11)22-10-6(17)3(14)2(13)4(15)7(10)18/h2-20H,1H3/t2-,3-,4+,5-,6-,7-,8-,9+,10-,11-,12+/m0/s1

> <INCHI_KEY>
KZSXJTYOPKQNLT-BCKMTSFNSA-N

> <FORMULA>
C12H22O11

> <MOLECULAR_WEIGHT>
342.2965

> <EXACT_MASS>
342.116211546

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
31.03050870574086

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,3R,4S,5S,6R)-6-{[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]oxy}cyclohexane-1,2,3,4,5-pentol

> <ALOGPS_LOGP>
-2.12

> <JCHEM_LOGP>
-4.643607793666667

> <ALOGPS_LOGS>
0.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.347101876417586

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.846396087316178

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6457742773975452

> <JCHEM_POLAR_SURFACE_AREA>
189.52999999999997

> <JCHEM_REFRACTIVITY>
68.0069

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.70e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3R,4S,5S,6R)-6-{[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]oxy}cyclohexane-1,2,3,4,5-pentol

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0049353 (Glucinol)
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PDB for NP0049353 (Glucinol)
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  O   UNK     0      -1.079   0.591   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.461   0.591   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.231  -0.742   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.461  -2.076   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.771  -0.742   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.541  -2.076   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.541   0.591   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.081   0.591   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.771   1.925   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.541   3.259   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.231   1.925   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.461   5.926   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.309   7.260   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.849   7.260   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.619   5.926   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.849   4.592   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.309   4.592   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.461   3.259   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -2.619   3.259   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -4.159   5.926   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.619   8.593   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.461   8.593   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.309   9.927   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    2   18                                                  
CONECT   12   13   17                                                       
CONECT   13   12   14   22                                                  
CONECT   14   13   15   21                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   12   18                                                  
CONECT   18   11   17                                                       
CONECT   19   16                                                            
CONECT   20   15                                                            
CONECT   21   14                                                            
CONECT   22   13   23                                                       
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

Download
3D PDB for NP0049353 (Glucinol)
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SMILES for NP0049353 (Glucinol)
CO[C@H]1O[C@@H](O[C@H]2[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O
Download
INCHI for NP0049353 (Glucinol)
InChI=1S/C12H22O11/c1-21-11-8(19)5(16)9(20)12(23-11)22-10-6(17)3(14)2(13)4(15)7(10)18/h2-20H,1H3/t2-,3-,4+,5-,6-,7-,8-,9+,10-,11-,12+/m0/s1
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View in JSmol
Synonyms
ValueSource
1-O-b-D-Glucopyranosyl-myo-inositolHMDB
Chemical FormulaC12H22O11
Average Mass342.2965 Da
Monoisotopic Mass342.11621 Da
IUPAC Name(1S,2R,3R,4S,5S,6R)-6-{[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]oxy}cyclohexane-1,2,3,4,5-pentol
Traditional Name(1S,2R,3R,4S,5S,6R)-6-{[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]oxy}cyclohexane-1,2,3,4,5-pentol
CAS Registry Number4539-73-5
SMILES
CO[C@H]1O[C@@H](O[C@H]2[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C12H22O11/c1-21-11-8(19)5(16)9(20)12(23-11)22-10-6(17)3(14)2(13)4(15)7(10)18/h2-20H,1H3/t2-,3-,4+,5-,6-,7-,8-,9+,10-,11-,12+/m0/s1
InChI KeyKZSXJTYOPKQNLT-BCKMTSFNSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Pimpinella anisumFooDB
Solanum tuberosumFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbohydrates and carbohydrate conjugates  
Direct ParentO-glycosyl compounds  
Alternative Parents
Substituents
  • O-glycosyl compound
    • 

  • Cyclohexanol
    • 

  • Oxane
    • 

  • Monosaccharide
    • 

  • Cyclitol or derivatives
    • 

  • Cyclic alcohol
    • 

  • Secondary alcohol
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Polyol
    • 

  • Acetal
    • 

  • Hydrocarbon derivative
    • 

  • 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-2.1ALOGPS
logP-4.6ChemAxon
logS0.03ALOGPS
pKa (Strongest Acidic)11.85ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area189.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity68.01 m³·mol⁻¹ChemAxon
Polarizability31.03 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0039237  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB018774  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available