NP-MRD: Showing NP-Card for Cachimoside (NP0054104)

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Record Information

Version

2.0

Created at

2022-04-28 00:33:56 UTC

Updated at

2022-04-28 00:33:56 UTC

NP-MRD ID

NP0054104

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cachimoside

Description

5,7-Dihydroxy-2-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-({[(2S,3R,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]-4H-chromen-4-one belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. Cachimoside is found in Gypsophila paniculata . Based on a literature review very few articles have been published on 5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-({[(2S,3R,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]-4H-chromen-4-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282202332D          

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M  END

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  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  1  0  0  0
 11 14  1  6  0  0  0
 10 15  1  1  0  0  0
  9 16  1  1  0  0  0
 16 17  1  0  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 23  1  0  0  0  0
 21 24  1  6  0  0  0
 20 25  1  6  0  0  0
 19 26  1  6  0  0  0
  5 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
  4 30  1  0  0  0  0
 30 31  2  0  0  0  0
 28 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 32 37  1  0  0  0  0
 35 38  1  0  0  0  0
  3 39  1  0  0  0  0
  1 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054104

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1CO[C@@H](OC[C@@H]2O[C@H]([C@H](O)[C@@H](O)[C@@H]2O)C2=C3OC(=CC(=O)C3=C(O)C=C2O)C2=CC=C(O)C=C2)[C@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H28O14/c27-10-3-1-9(2-4-10)15-6-13(30)17-11(28)5-12(29)18(24(17)39-15)25-22(35)21(34)20(33)16(40-25)8-38-26-23(36)19(32)14(31)7-37-26/h1-6,14,16,19-23,25-29,31-36H,7-8H2/t14-,16+,19-,20-,21+,22-,23-,25+,26+/m1/s1

> <INCHI_KEY>
DLIIIVWLAGTXTQ-HUQTVITBSA-N

> <FORMULA>
C26H28O14

> <MOLECULAR_WEIGHT>
564.496

> <EXACT_MASS>
564.147905582

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
54.65690980975286

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-({[(2S,3R,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]-4H-chromen-4-one

> <ALOGPS_LOGP>
-0.41

> <JCHEM_LOGP>
-1.1911324750000003

> <ALOGPS_LOGS>
-2.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.001042657026622

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.1727567217411075

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6450214812443376

> <JCHEM_POLAR_SURFACE_AREA>
236.05999999999995

> <JCHEM_REFRACTIVITY>
132.483

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.03e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-({[(2S,3R,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.668   8.470   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.001   8.470   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -8.002   9.240   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -8.002   6.160   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6   40                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   39                                                  
CONECT    4    3    5   30                                                  
CONECT    5    4    6   27                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10   12   14                                                  
CONECT   12   11    7   13                                                  
CONECT   13   12                                                            
CONECT   14   11                                                            
CONECT   15   10                                                            
CONECT   16    9   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20   26                                                  
CONECT   20   19   21   25                                                  
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
CONECT   24   21                                                            
CONECT   25   20                                                            
CONECT   26   19                                                            
CONECT   27    5   28                                                       
CONECT   28   27   29   32                                                  
CONECT   29   28   30                                                       
CONECT   30   29    4   31                                                  
CONECT   31   30                                                            
CONECT   32   28   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   38                                                  
CONECT   36   35   37                                                       
CONECT   37   36   32                                                       
CONECT   38   35                                                            
CONECT   39    3                                                            
CONECT   40    1                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₈O₁₄

Average Mass

564.4960 Da

Monoisotopic Mass

564.14791 Da

IUPAC Name

5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-({[(2S,3R,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]-4H-chromen-4-one

Traditional Name

5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-({[(2S,3R,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]chromen-4-one

CAS Registry Number

Not Available

SMILES

O[C@@H]1CO[C@@H](OC[C@@H]2O[C@H]([C@H](O)[C@@H](O)[C@@H]2O)C2=C3OC(=CC(=O)C3=C(O)C=C2O)C2=CC=C(O)C=C2)[C@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C26H28O14/c27-10-3-1-9(2-4-10)15-6-13(30)17-11(28)5-12(29)18(24(17)39-15)25-22(35)21(34)20(33)16(40-25)8-38-26-23(36)19(32)14(31)7-37-26/h1-6,14,16,19-23,25-29,31-36H,7-8H2/t14-,16+,19-,20-,21+,22-,23-,25+,26+/m1/s1

InChI Key

DLIIIVWLAGTXTQ-HUQTVITBSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Gypsophila paniculata	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid 8-C-glycosides

Alternative Parents

Substituents

Flavonoid-8-c-glycoside
Hydroxyflavonoid
Flavone
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
Phenolic glycoside
O-glycosyl compound
Glycosyl compound
Disaccharide
Chromone
C-glycosyl compound
1-benzopyran
Benzopyran
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Phenol
Benzenoid
Pyran
Oxane
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Dialkyl ether
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	-0.41	ALOGPS
logP	-1.2	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	6.17	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	236.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	132.48 m³·mol⁻¹	ChemAxon
Polarizability	54.66 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

Not Available

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

162982049

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Cachimoside (NP0054104)

MOL for NP0054104 (Cachimoside)

3D MOL for NP0054104 (Cachimoside)

3D SDF for NP0054104 (Cachimoside)

3D-SDF for NP0054104 (Cachimoside)

PDB for NP0054104 (Cachimoside)

3D PDB for NP0054104 (Cachimoside)

SMILES for NP0054104 (Cachimoside)

INCHI for NP0054104 (Cachimoside)

Structure for NP0054104 (Cachimoside)

3D Structure for NP0054104 (Cachimoside)