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Showing NP-Card for (S)-2-Hydroxy-2-phenylacetonitrile O-[b-D-apiosyl-(1->2)-b-D-glucoside] (NP0335079)

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Record Information
Version2.0
Created at2024-09-10 23:47:57 UTC
Updated at2024-09-10 23:47:57 UTC
NP-MRD IDNP0335079
Secondary Accession NumbersNone
Natural Product Identification
Common Name(S)-2-Hydroxy-2-phenylacetonitrile O-[b-D-apiosyl-(1->2)-b-D-glucoside]
Description(S)-2-Hydroxy-2-phenylacetonitrile O-[b-D-apiosyl-(1->2)-b-D-glucoside] belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group. Based on a literature review very few articles have been published on (S)-2-Hydroxy-2-phenylacetonitrile O-[b-D-apiosyl-(1->2)-b-D-glucoside].
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0335079 ((S)-2-Hydroxy-2-phenylacetonitrile O-[b-D-apiosyl-(1->2)-b-D-glucoside])


  Mrv2104 05262302202D          

 30 32  0  0  0  0            999 V2000
   -2.8700    0.7640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8700   -0.0611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1562   -0.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4440   -0.0611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4440    0.7640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1562    1.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7289    1.1765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0138    0.7640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7289    2.0016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7289    2.8267    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6999    1.1765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4164    0.7640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1301    1.1765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1301    2.0016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4164    2.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6999    2.0016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4178    3.2364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7040    3.6504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8439    2.4155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8451    0.7640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4164   -0.0611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4164   -0.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7508   -1.3744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0080   -2.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8317   -2.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0848   -1.3744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8700   -1.1200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3171   -2.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3171   -3.6504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6185   -2.9559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 11  1  0  0  0  0
  9 10  3  0  0  0  0
 11 12  1  0  0  0  0
 11 16  1  0  0  0  0
 12 13  1  0  0  0  0
 12 21  1  0  0  0  0
 13 14  1  0  0  0  0
 13 20  1  0  0  0  0
 14 15  1  0  0  0  0
 14 19  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 26  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 28  1  0  0  0  0
 25 30  1  0  0  0  0
 26 27  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
Download

3D MOL for NP0335079 ((S)-2-Hydroxy-2-phenylacetonitrile O-[b-D-apiosyl-(1->2)-b-D-glucoside])

Download
3D SDF for NP0335079 ((S)-2-Hydroxy-2-phenylacetonitrile O-[b-D-apiosyl-(1->2)-b-D-glucoside])

  Mrv2104 05262302202D          

 30 32  0  0  0  0            999 V2000
   -2.8700    0.7640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8700   -0.0611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1562   -0.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4440   -0.0611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4440    0.7640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1562    1.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7289    1.1765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0138    0.7640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7289    2.0016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7289    2.8267    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6999    1.1765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4164    0.7640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1301    1.1765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1301    2.0016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4164    2.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6999    2.0016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4178    3.2364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7040    3.6504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8439    2.4155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8451    0.7640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4164   -0.0611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4164   -0.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7508   -1.3744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0080   -2.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8317   -2.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0848   -1.3744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8700   -1.1200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3171   -2.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3171   -3.6504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6185   -2.9559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 11  1  0  0  0  0
  9 10  3  0  0  0  0
 11 12  1  0  0  0  0
 11 16  1  0  0  0  0
 12 13  1  0  0  0  0
 12 21  1  0  0  0  0
 13 14  1  0  0  0  0
 13 20  1  0  0  0  0
 14 15  1  0  0  0  0
 14 19  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 26  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 28  1  0  0  0  0
 25 30  1  0  0  0  0
 26 27  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0335079

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OC(C#N)C2=CC=CC=C2)C(OC2OCC(O)(CO)C2O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1/C19H25NO10/c20-6-11(10-4-2-1-3-5-10)28-17-15(14(24)13(23)12(7-21)29-17)30-18-16(25)19(26,8-22)9-27-18/h1-5,11-18,21-26H,7-9H2

> <INCHI_KEY>
UXSSAGLYQCOTML-UHFFFAOYNA-N

> <FORMULA>
C19H25NO10

> <MOLECULAR_WEIGHT>
427.406

> <EXACT_MASS>
427.147846009

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
41.33558566870228

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-2-phenylacetonitrile

> <JCHEM_LOGP>
-2.0935501943333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.64946129826792

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.807126922861041

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810844904201037

> <JCHEM_POLAR_SURFACE_AREA>
182.09

> <JCHEM_REFRACTIVITY>
96.7666

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-[(3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-2-phenylacetonitrile

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0335079 ((S)-2-Hydroxy-2-phenylacetonitrile O-[b-D-apiosyl-(1->2)-b-D-glucoside])
Download
PDB for NP0335079 ((S)-2-Hydroxy-2-phenylacetonitrile O-[b-D-apiosyl-(1->2)-b-D-glucoside])
HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      -5.357   1.426   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.357  -0.114   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.025  -0.884   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.695  -0.114   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.695   1.426   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.025   2.194   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.361   2.196   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.026   1.426   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.361   3.736   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -1.361   5.277   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       1.306   2.196   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.644   1.426   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.976   2.196   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.976   3.736   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.644   4.501   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.306   3.736   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.647   6.041   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.314   6.814   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.309   4.509   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.311   1.426   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.644  -0.114   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.644  -1.654   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.401  -2.566   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.882  -4.029   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.419  -4.029   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.892  -2.566   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.357  -2.091   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.325  -5.274   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.325  -6.814   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       3.021  -5.518   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    1    5                                                       
CONECT    7    5    8    9                                                  
CONECT    8    7   11                                                       
CONECT    9    7   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   16                                                  
CONECT   12   11   13   21                                                  
CONECT   13   12   14   20                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16   17                                                  
CONECT   16   11   15                                                       
CONECT   17   15   18                                                       
CONECT   18   17                                                            
CONECT   19   14                                                            
CONECT   20   13                                                            
CONECT   21   12   22                                                       
CONECT   22   21   23   26                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   28   30                                             
CONECT   26   22   25   27                                                  
CONECT   27   26                                                            
CONECT   28   25   29                                                       
CONECT   29   28                                                            
CONECT   30   25                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

Download
3D PDB for NP0335079 ((S)-2-Hydroxy-2-phenylacetonitrile O-[b-D-apiosyl-(1->2)-b-D-glucoside])
Download
SMILES for NP0335079 ((S)-2-Hydroxy-2-phenylacetonitrile O-[b-D-apiosyl-(1->2)-b-D-glucoside])
OCC1OC(OC(C#N)C2=CC=CC=C2)C(OC2OCC(O)(CO)C2O)C(O)C1O
Download
INCHI for NP0335079 ((S)-2-Hydroxy-2-phenylacetonitrile O-[b-D-apiosyl-(1->2)-b-D-glucoside])
InChI=1/C19H25NO10/c20-6-11(10-4-2-1-3-5-10)28-17-15(14(24)13(23)12(7-21)29-17)30-18-16(25)19(26,8-22)9-27-18/h1-5,11-18,21-26H,7-9H2
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View in JSmol
SynonymsNot Available
Chemical FormulaC19H25NO10
Average Mass427.4060 Da
Monoisotopic Mass427.14785 Da
IUPAC Name2-[(3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-2-phenylacetonitrile
Traditional Name2-[(3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-2-phenylacetonitrile
CAS Registry NumberNot Available
SMILES
OCC1OC(OC(C#N)C2=CC=CC=C2)C(OC2OCC(O)(CO)C2O)C(O)C1O
InChI Identifier
InChI=1/C19H25NO10/c20-6-11(10-4-2-1-3-5-10)28-17-15(14(24)13(23)12(7-21)29-17)30-18-16(25)19(26,8-22)9-27-18/h1-5,11-18,21-26H,7-9H2
InChI KeyUXSSAGLYQCOTML-UHFFFAOYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbohydrates and carbohydrate conjugates  
Direct ParentCyanogenic glycosides  
Alternative Parents
Substituents
  • Cyanogenic glycoside
    • 

  • Disaccharide
    • 

  • O-glycosyl compound
    • 

  • Monocyclic benzene moiety
    • 

  • Oxane
    • 

  • Benzenoid
    • 

  • Tetrahydrofuran
    • 

  • Tertiary alcohol
    • 

  • Secondary alcohol
    • 

  • Nitrile
    • 

  • Carbonitrile
    • 

  • Acetal
    • 

  • Organoheterocyclic compound
    • 

  • Oxacycle
    • 

  • Primary alcohol
    • 

  • Alcohol
    • 

  • Organonitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organopnictogen compound
    • 

  • Organic nitrogen compound
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic 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-2.1ChemAxon
pKa (Strongest Acidic)11.81ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area182.09 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity96.77 m³·mol⁻¹ChemAxon
Polarizability41.34 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
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