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Showing NP-Card for Naringenin 5-rhamnoside (NP0336835)

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Record Information
Version2.0
Created at2024-09-11 08:02:55 UTC
Updated at2024-09-11 08:02:56 UTC
NP-MRD IDNP0336835
Secondary Accession NumbersNone
Natural Product Identification
Common NameNaringenin 5-rhamnoside
DescriptionNaringenin 5-rhamnoside belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Based on a literature review very few articles have been published on Naringenin 5-rhamnoside.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0336835 (Naringenin 5-rhamnoside)


  Mrv2104 05262310352D          

 30 33  0  0  0  0            999 V2000
   -1.0710    1.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7860    0.7287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7860   -0.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0710   -0.5087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574   -0.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574    0.7287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3576    1.1411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0724    0.7287    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0724   -0.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3576   -0.5087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3576   -1.3337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4996    1.1411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0710   -1.3337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7860   -1.7461    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7860   -2.5711    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0710   -2.9835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4996   -1.3337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2145   -1.7461    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9295   -1.3337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2145   -2.5711    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4996   -2.9835    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4996   -3.8085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5009    2.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7860    1.9661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7860    1.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5009    0.7287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2159    1.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2159    1.9661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9295    2.3785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9289   -2.9837    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
  2 12  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4 13  1  0  0  0  0
  5  6  2  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 25  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 14 15  1  0  0  0  0
 14 17  1  0  0  0  0
 15 16  1  6  0  0  0
 15 21  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 23 24  2  0  0  0  0
 23 28  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 20 30  1  1  0  0  0
 14 13  1  1  0  0  0
M  END
Download

3D MOL for NP0336835 (Naringenin 5-rhamnoside)

Download
3D SDF for NP0336835 (Naringenin 5-rhamnoside)

  Mrv2104 05262310352D          

 30 33  0  0  0  0            999 V2000
   -1.0710    1.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7860    0.7287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7860   -0.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0710   -0.5087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574   -0.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574    0.7287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3576    1.1411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0724    0.7287    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0724   -0.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3576   -0.5087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3576   -1.3337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4996    1.1411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0710   -1.3337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7860   -1.7461    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7860   -2.5711    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0710   -2.9835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4996   -1.3337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2145   -1.7461    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9295   -1.3337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2145   -2.5711    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4996   -2.9835    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4996   -3.8085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5009    2.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7860    1.9661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7860    1.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5009    0.7287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2159    1.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2159    1.9661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9295    2.3785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9289   -2.9837    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
  2 12  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4 13  1  0  0  0  0
  5  6  2  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 25  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 14 15  1  0  0  0  0
 14 17  1  0  0  0  0
 15 16  1  6  0  0  0
 15 21  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 23 24  2  0  0  0  0
 23 28  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 20 30  1  1  0  0  0
 14 13  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0336835

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](OC2=CC(O)=CC3=C2C(=O)C[C@H](O3)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1/C21H22O9/c1-9-18(25)19(26)20(27)21(28-9)30-16-7-12(23)6-15-17(16)13(24)8-14(29-15)10-2-4-11(22)5-3-10/h2-7,9,14,18-23,25-27H,8H2,1H3/t9-,14-,18-,19+,20+,21-/s2

> <INCHI_KEY>
OVWZFLKQVPSRDZ-RCNRMAMNNA-N

> <FORMULA>
C21H22O9

> <MOLECULAR_WEIGHT>
418.398

> <EXACT_MASS>
418.126382288

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
40.59684320783799

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-7-hydroxy-2-(4-hydroxyphenyl)-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one

> <JCHEM_LOGP>
0.9639499236666664

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.480285137722339

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.802501163652385

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6122003633066284

> <JCHEM_POLAR_SURFACE_AREA>
145.91000000000003

> <JCHEM_REFRACTIVITY>
101.8905

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-7-hydroxy-2-(4-hydroxyphenyl)-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0336835 (Naringenin 5-rhamnoside)
Download
PDB for NP0336835 (Naringenin 5-rhamnoside)
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      -1.999   2.130   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.334   1.360   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.334  -0.180   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.999  -0.950   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.667  -0.180   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.667   1.360   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.668   2.130   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.002   1.360   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.002  -0.180   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.668  -0.950   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.668  -2.490   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -4.666   2.130   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.999  -2.490   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.334  -3.259   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.334  -4.799   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.999  -5.569   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -4.666  -2.490   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -6.000  -3.259   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -7.335  -2.490   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.000  -4.799   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.666  -5.569   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.666  -7.109   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.668   4.440   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.334   3.670   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.334   2.130   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.668   1.360   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.003   2.130   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.003   3.670   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       7.335   4.440   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -7.334  -5.570   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6   10                                                  
CONECT    6    1    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   25                                                  
CONECT    9    8   10                                                       
CONECT   10    5    9   11                                                  
CONECT   11   10                                                            
CONECT   12    2                                                            
CONECT   13    4   14                                                       
CONECT   14   15   17   13                                                  
CONECT   15   14   16   21                                                  
CONECT   16   15                                                            
CONECT   17   14   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   30                                                  
CONECT   21   15   20   22                                                  
CONECT   22   21                                                            
CONECT   23   24   28                                                       
CONECT   24   23   25                                                       
CONECT   25    8   24   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   23   27   29                                                  
CONECT   29   28                                                            
CONECT   30   20                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

Download
3D PDB for NP0336835 (Naringenin 5-rhamnoside)
Download
SMILES for NP0336835 (Naringenin 5-rhamnoside)
C[C@@H]1O[C@@H](OC2=CC(O)=CC3=C2C(=O)C[C@H](O3)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O
Download
INCHI for NP0336835 (Naringenin 5-rhamnoside)
InChI=1/C21H22O9/c1-9-18(25)19(26)20(27)21(28-9)30-16-7-12(23)6-15-17(16)13(24)8-14(29-15)10-2-4-11(22)5-3-10/h2-7,9,14,18-23,25-27H,8H2,1H3/t9-,14-,18-,19+,20+,21-/s2
Download
View in JSmol
SynonymsNot Available
Chemical FormulaC21H22O9
Average Mass418.3980 Da
Monoisotopic Mass418.12638 Da
IUPAC Name(2S)-7-hydroxy-2-(4-hydroxyphenyl)-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Name(2S)-7-hydroxy-2-(4-hydroxyphenyl)-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one
CAS Registry NumberNot Available
SMILES
C[C@@H]1O[C@@H](OC2=CC(O)=CC3=C2C(=O)C[C@H](O3)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O
InChI Identifier
InChI=1/C21H22O9/c1-9-18(25)19(26)20(27)21(28-9)30-16-7-12(23)6-15-17(16)13(24)8-14(29-15)10-2-4-11(22)5-3-10/h2-7,9,14,18-23,25-27H,8H2,1H3/t9-,14-,18-,19+,20+,21-/s2
InChI KeyOVWZFLKQVPSRDZ-RCNRMAMNNA-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 flavonoid o-glycosides. These are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassFlavonoids  
Sub ClassFlavonoid glycosides  
Direct ParentFlavonoid O-glycosides  
Alternative Parents
Substituents
  • Flavonoid o-glycoside
    • 

  • Flavonoid-5-o-glycoside
    • 

  • Hydroxyflavonoid
    • 

  • 4'-hydroxyflavonoid
    • 

  • 7-hydroxyflavonoid
    • 

  • Flavanone
    • 

  • Flavan
    • 

  • Phenolic glycoside
    • 

  • Hexose monosaccharide
    • 

  • Glycosyl compound
    • 

  • O-glycosyl compound
    • 

  • Chromone
    • 

  • Benzopyran
    • 

  • Chromane
    • 

  • 1-benzopyran
    • 

  • Aryl alkyl ketone
    • 

  • Aryl ketone
    • 

  • Phenol
    • 

  • Alkyl aryl ether
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Monocyclic benzene moiety
    • 

  • Benzenoid
    • 

  • Oxane
    • 

  • Monosaccharide
    • 

  • Secondary alcohol
    • 

  • Ketone
    • 

  • Polyol
    • 

  • Ether
    • 

  • Organoheterocyclic compound
    • 

  • Oxacycle
    • 

  • Acetal
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
logP0.96ChemAxon
pKa (Strongest Acidic)7.8ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area145.91 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity101.89 m³·mol⁻¹ChemAxon
Polarizability40.6 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
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References
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