NP-MRD: Showing NP-Card for (-)-Cussoracoside E (NP0072820)

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Record Information

Version

2.0

Created at

2022-04-28 18:06:20 UTC

Updated at

2022-04-28 18:06:21 UTC

NP-MRD ID

NP0072820

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Cussoracoside E

Description

Cussoracoside E belongs to the class of organic compounds known as steviol glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically linked to a steviol (a diterpenoid based on a 13-Hydroxykaur-16-en-18-oic acid) moiety. (-)-Cussoracoside E is found in Cussonia racemosa. Based on a literature review very few articles have been published on Cussoracoside E.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282220062D          

 35 39  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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 21 23  1  0  0  0  0
 24 23  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  1  0  0  0
 28 31  1  6  0  0  0
 27 32  1  1  0  0  0
 26 33  1  6  0  0  0
 33 34  1  0  0  0  0
  2 35  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0072820

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]12CC[C@@H](O)[C@](C)([C@H]1CC[C@@]13C[C@@H]([C@H](O)C[C@@H]21)C(=C)C3)C(=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H40O9/c1-12-9-26-7-4-16-24(2,17(26)8-14(28)13(12)10-26)6-5-18(29)25(16,3)23(33)35-22-21(32)20(31)19(30)15(11-27)34-22/h13-22,27-32H,1,4-11H2,2-3H3/t13-,14-,15-,16+,17+,18-,19-,20+,21-,22+,24-,25+,26-/m1/s1

> <INCHI_KEY>
ZEQWNCCUXZWGMJ-OBENPHAASA-N

> <FORMULA>
C26H40O9

> <MOLECULAR_WEIGHT>
496.597

> <EXACT_MASS>
496.267232868

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
52.1174229058948

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1S,4S,5S,6R,9S,10R,12R,13R)-6,12-dihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylate

> <ALOGPS_LOGP>
-0.09

> <JCHEM_LOGP>
0.00018680700000134332

> <ALOGPS_LOGS>
-2.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.173706761002041

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.193747703694468

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8944706883137906

> <JCHEM_POLAR_SURFACE_AREA>
156.91

> <JCHEM_REFRACTIVITY>
122.90279999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.75e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1S,4S,5S,6R,9S,10R,12R,13R)-6,12-dihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylate

> <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       6.193   2.670   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.658   1.202   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.618   0.065   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.115   0.397   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.650   1.866   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.690   3.002   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.118   2.243   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.999   1.022   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.569  -0.447   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.080  -0.758   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.112   2.016   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.964   2.885   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.081   4.116   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.659   3.819   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.433   5.567   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.675   1.439   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.193   1.177   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.512   0.307   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.203   3.340   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.718  -1.013   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.339  -1.449   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.888  -1.964   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       6.511  -2.448   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.232  -3.963   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.404  -4.962   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.124  -6.476   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.673  -6.991   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.501  -5.992   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.781  -4.478   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.609  -3.479   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       3.050  -6.508   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       5.394  -8.506   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       8.296  -7.475   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       8.017  -8.990   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       8.162   0.870   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   35                                                  
CONECT    3    2    4   20   21                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   19                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   14                                                  
CONECT    8    7    9   11   18                                             
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13    7                                                       
CONECT   15   13                                                            
CONECT   16   12   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    8                                                       
CONECT   19    5                                                            
CONECT   20    3                                                            
CONECT   21    3   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   33                                                  
CONECT   27   26   28   32                                                  
CONECT   28   27   29   31                                                  
CONECT   29   28   24   30                                                  
CONECT   30   29                                                            
CONECT   31   28                                                            
CONECT   32   27                                                            
CONECT   33   26   34                                                       
CONECT   34   33                                                            
CONECT   35    2                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₄₀O₉

Average Mass

496.5970 Da

Monoisotopic Mass

496.26723 Da

IUPAC Name

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1S,4S,5S,6R,9S,10R,12R,13R)-6,12-dihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylate

Traditional Name

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1S,4S,5S,6R,9S,10R,12R,13R)-6,12-dihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylate

CAS Registry Number

Not Available

SMILES

C[C@@]12CC[C@@H](O)[C@](C)([C@H]1CC[C@@]13C[C@@H]([C@H](O)C[C@@H]21)C(=C)C3)C(=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C26H40O9/c1-12-9-26-7-4-16-24(2,17(26)8-14(28)13(12)10-26)6-5-18(29)25(16,3)23(33)35-22-21(32)20(31)19(30)15(11-27)34-22/h13-22,27-32H,1,4-11H2,2-3H3/t13-,14-,15-,16+,17+,18-,19-,20+,21-,22+,24-,25+,26-/m1/s1

InChI Key

ZEQWNCCUXZWGMJ-OBENPHAASA-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
Cussonia racemosa	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steviol glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically linked to a steviol (a diterpenoid based on a 13-Hydroxykaur-16-en-18-oic acid) moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Steviol glycosides

Alternative Parents

Substituents

Steviol glycoside
Diterpenoid
Kaurane diterpenoid
Steroid
Hexose monosaccharide
Beta-hydroxy acid
Hydroxy acid
Monosaccharide
Oxane
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Polyol
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Primary alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	-0.09	ALOGPS
logP	0.00019	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	12.19	ChemAxon
pKa (Strongest Basic)	-0.89	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	122.9 m³·mol⁻¹	ChemAxon
Polarizability	52.12 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	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

C00032870

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

11827149

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (-)-Cussoracoside E (NP0072820)

MOL for NP0072820 ((-)-Cussoracoside E)

3D MOL for NP0072820 ((-)-Cussoracoside E)

3D SDF for NP0072820 ((-)-Cussoracoside E)

3D-SDF for NP0072820 ((-)-Cussoracoside E)

PDB for NP0072820 ((-)-Cussoracoside E)

3D PDB for NP0072820 ((-)-Cussoracoside E)

SMILES for NP0072820 ((-)-Cussoracoside E)

INCHI for NP0072820 ((-)-Cussoracoside E)

Structure for NP0072820 ((-)-Cussoracoside E)

3D Structure for NP0072820 ((-)-Cussoracoside E)