NP-MRD: Showing NP-Card for (-)-Suavioside E (NP0075134)

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Record Information

Version

2.0

Created at

2022-04-28 20:26:22 UTC

Updated at

2022-04-28 20:26:22 UTC

NP-MRD ID

NP0075134

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Suavioside E

Description

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1S,4S,5R,9S,10S,13R,14S)-14-hydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecane-5-carboxylate belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. (-)-Suavioside E is found in Cussonia vantsilana Baker. Based on a literature review very few articles have been published on (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1S,4S,5R,9S,10S,13R,14S)-14-hydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecane-5-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282222262D          

 35 39  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304282222262D          

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  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  1  0  0  0
  8 11  1  1  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  6  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
  8 16  1  0  0  0  0
 15 17  1  1  0  0  0
 17 18  1  0  0  0  0
 15 19  1  6  0  0  0
  5 20  1  1  0  0  0
  3 21  1  6  0  0  0
  3 22  1  1  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 25 24  1  6  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
 29 30  1  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  1  0  0  0
 29 32  1  6  0  0  0
 28 33  1  1  0  0  0
 27 34  1  6  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0075134

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C26H42O9/c1-23-7-3-8-24(2,22(32)35-21-20(31)19(30)18(29)15(11-27)34-21)16(23)6-9-25-10-14(4-5-17(23)25)26(33,12-25)13-28/h14-21,27-31,33H,3-13H2,1-2H3/t14-,15-,16+,17-,18-,19+,20-,21+,23-,24-,25+,26-/m1/s1

> <INCHI_KEY>
XKXZHTWOHXJEOL-DFTQOQLFSA-N

> <FORMULA>
C26H42O9

> <MOLECULAR_WEIGHT>
498.613

> <EXACT_MASS>
498.282882932

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
53.112320757966394

> <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,5R,9S,10S,13R,14S)-14-hydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylate

> <ALOGPS_LOGP>
0.14

> <JCHEM_LOGP>
0.5252912903333335

> <ALOGPS_LOGS>
-2.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.086815169664177

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.182289346891764

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981093680169468

> <JCHEM_POLAR_SURFACE_AREA>
156.91

> <JCHEM_REFRACTIVITY>
123.24309999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.72e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1S,4S,5R,9S,10S,13R,14S)-14-hydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[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  C   UNK     0      -1.675   1.439   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.512   0.307   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.126   1.956   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -4.299   0.958   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -2.869   0.466   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.203   3.340   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.718  -1.013   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.339  -1.449   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.888  -1.964   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.511  -2.448   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.232  -3.963   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.404  -4.962   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.124  -6.476   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.673  -6.991   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.501  -5.992   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.781  -4.478   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.609  -3.479   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       3.050  -6.508   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       5.394  -8.506   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       8.296  -7.475   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       8.017  -8.990   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   21   22                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   20                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   14                                                  
CONECT    8    7    9   11   16                                             
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13    7                                                       
CONECT   15   12   16   17   19                                             
CONECT   16   15    8                                                       
CONECT   17   15   18                                                       
CONECT   18   17                                                            
CONECT   19   15                                                            
CONECT   20    5                                                            
CONECT   21    3                                                            
CONECT   22    3   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   34                                                  
CONECT   28   27   29   33                                                  
CONECT   29   28   30   32                                                  
CONECT   30   29   25   31                                                  
CONECT   31   30                                                            
CONECT   32   29                                                            
CONECT   33   28                                                            
CONECT   34   27   35                                                       
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl (1S,4S,5R,9S,10S,13R,14S)-14-hydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0,.0,]hexadecane-5-carboxylic acid	Generator

Chemical Formula

C₂₆H₄₂O₉

Average Mass

498.6130 Da

Monoisotopic Mass

498.28288 Da

IUPAC Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C26H42O9/c1-23-7-3-8-24(2,22(32)35-21-20(31)19(30)18(29)15(11-27)34-21)16(23)6-9-25-10-14(4-5-17(23)25)26(33,12-25)13-28/h14-21,27-31,33H,3-13H2,1-2H3/t14-,15-,16+,17-,18-,19+,20-,21+,23-,24-,25+,26-/m1/s1

InChI Key

XKXZHTWOHXJEOL-DFTQOQLFSA-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 vantsilana Baker	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Diterpene glycosides

Alternative Parents

Substituents

Diterpene glycoside
Kaurane diterpenoid
Diterpenoid
Hexose monosaccharide
Oxane
Monosaccharide
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
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	0.14	ALOGPS
logP	0.53	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	12.18	ChemAxon
pKa (Strongest Basic)	-3	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	5	ChemAxon
Refractivity	123.24 m³·mol⁻¹	ChemAxon
Polarizability	53.11 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

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

163013682

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Suavioside E (NP0075134)

MOL for NP0075134 ((-)-Suavioside E)

3D MOL for NP0075134 ((-)-Suavioside E)

3D SDF for NP0075134 ((-)-Suavioside E)

3D-SDF for NP0075134 ((-)-Suavioside E)

PDB for NP0075134 ((-)-Suavioside E)

3D PDB for NP0075134 ((-)-Suavioside E)

SMILES for NP0075134 ((-)-Suavioside E)

INCHI for NP0075134 ((-)-Suavioside E)

Structure for NP0075134 ((-)-Suavioside E)

3D Structure for NP0075134 ((-)-Suavioside E)