NP-MRD: Showing NP-Card for 5-hydroxy-2-(4-hydroxyphenyl)-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-7-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}chromen-4-one (NP0330894)

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Record Information

Version

2.0

Created at

2022-09-12 16:41:08 UTC

Updated at

2022-09-12 16:41:09 UTC

NP-MRD ID

NP0330894

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-hydroxy-2-(4-hydroxyphenyl)-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-7-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}chromen-4-one

Description

5-hydroxy-2-(4-hydroxyphenyl)-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-7-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}chromen-4-one is found in Indigofera hebepetala. Based on a literature review very few articles have been published on Kaempferol 3-rhamnoside-7-alpha-l-arabionopyranoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309122218412D          

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M  END

     RDKit          3D

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  Mrv1652309122218412D          

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  4  5  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 14  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 19  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  1  1  0  0  0
 18 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 16 32  1  0  0  0  0
 32 33  1  0  0  0  0
  6 33  1  0  0  0  0
 33 34  2  0  0  0  0
  4 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
 37 38  1  1  0  0  0
 37 39  1  0  0  0  0
  2 39  1  0  0  0  0
 39 40  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0330894

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](OC2=C(OC3=CC(O[C@@H]4OC[C@H](O)[C@H](O)[C@H]4O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H28O14/c1-9-17(30)20(33)22(35)26(37-9)40-24-19(32)16-13(28)6-12(38-25-21(34)18(31)14(29)8-36-25)7-15(16)39-23(24)10-2-4-11(27)5-3-10/h2-7,9,14,17-18,20-22,25-31,33-35H,8H2,1H3/t9-,14-,17-,18-,20+,21+,22+,25-,26-/m0/s1

> <INCHI_KEY>
WIALSWOBTZTJMW-CLFUFSEMSA-N

> <FORMULA>
C26H28O14

> <MOLECULAR_WEIGHT>
564.496

> <EXACT_MASS>
564.147905582

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
53.62536808680494

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-0.4320931589999991

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.556783880029561

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.083364780633833

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5265985037685867

> <JCHEM_POLAR_SURFACE_AREA>
225.05999999999997

> <JCHEM_REFRACTIVITY>
131.93280000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+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   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.669  -0.000   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   39                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   35                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   33                                                  
CONECT    7    6    8   15                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    8                                                       
CONECT   15    7   16                                                       
CONECT   16   15   17   32                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   29                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   27                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   20   28                                                  
CONECT   28   27                                                            
CONECT   29   18   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   16   33                                                  
CONECT   33   32    6   34                                                  
CONECT   34   33                                                            
CONECT   35    4   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37    2   40                                                  
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

View in JSmol

Synonyms

Value	Source
Kaempferol 3-rhamnoside-7-a-L-arabionopyranoside	Generator
Kaempferol 3-rhamnoside-7-α-L-arabionopyranoside	Generator

Chemical Formula

C₂₆H₂₈O₁₄

Average Mass

564.4960 Da

Monoisotopic Mass

564.14791 Da

IUPAC Name

5-hydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-7-{[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-4H-chromen-4-one

Traditional Name

5-hydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-7-{[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}chromen-4-one

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](OC2=C(OC3=CC(O[C@@H]4OC[C@H](O)[C@H](O)[C@H]4O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C26H28O14/c1-9-17(30)20(33)22(35)26(37-9)40-24-19(32)16-13(28)6-12(38-25-21(34)18(31)14(29)8-36-25)7-15(16)39-23(24)10-2-4-11(27)5-3-10/h2-7,9,14,17-18,20-22,25-31,33-35H,8H2,1H3/t9-,14-,17-,18-,20+,21+,22+,25-,26-/m0/s1

InChI Key

WIALSWOBTZTJMW-CLFUFSEMSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Indigofera hebepetala	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	-0.43	ChemAxon
pKa (Strongest Acidic)	7.08	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	225.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	131.93 m³·mol⁻¹	ChemAxon
Polarizability	53.63 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00005186

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

54431865

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-hydroxy-2-(4-hydroxyphenyl)-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-7-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}chromen-4-one (NP0330894)

MOL for NP0330894 (5-hydroxy-2-(4-hydroxyphenyl)-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-7-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}chromen-4-one)

3D MOL for NP0330894 (5-hydroxy-2-(4-hydroxyphenyl)-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-7-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}chromen-4-one)

3D SDF for NP0330894 (5-hydroxy-2-(4-hydroxyphenyl)-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-7-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}chromen-4-one)

3D-SDF for NP0330894 (5-hydroxy-2-(4-hydroxyphenyl)-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-7-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}chromen-4-one)

PDB for NP0330894 (5-hydroxy-2-(4-hydroxyphenyl)-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-7-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}chromen-4-one)

3D PDB for NP0330894 (5-hydroxy-2-(4-hydroxyphenyl)-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-7-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}chromen-4-one)

SMILES for NP0330894 (5-hydroxy-2-(4-hydroxyphenyl)-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-7-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}chromen-4-one)

INCHI for NP0330894 (5-hydroxy-2-(4-hydroxyphenyl)-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-7-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}chromen-4-one)

Structure for NP0330894 (5-hydroxy-2-(4-hydroxyphenyl)-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-7-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}chromen-4-one)

3D Structure for NP0330894 (5-hydroxy-2-(4-hydroxyphenyl)-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-7-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}chromen-4-one)