NP-MRD: Showing NP-Card for Canescein (NP0085404)

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Record Information

Version

2.0

Created at

2022-04-29 05:56:39 UTC

Updated at

2022-04-29 05:56:39 UTC

NP-MRD ID

NP0085404

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Canescein

Description

Canescein belongs to the class of organic compounds known as cardenolide glycosides and derivatives. Cardenolide glycosides and derivatives are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety. Canescein is found in Convallaria majalis and Crossopetalum gaumeri. Based on a literature review very few articles have been published on Canescein.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292207562D          

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M  END

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M  END


  Mrv1652304292207562D          

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    2.1794    0.4982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5392   -1.0201    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3416   -1.8210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1906   -1.5264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8734   -1.0634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6441   -0.2709    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4543   -0.4264    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1505    0.3804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9211    1.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6040    1.6359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2553    1.1295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9750    0.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6308    2.4604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1774   -2.2316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6168   -0.6798    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3365    0.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8683    0.7268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1486   -0.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9608   -0.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3971   -0.6299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  1  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 31 35  1  0  0  0  0
 33 36  2  0  0  0  0
 13 37  1  1  0  0  0
 13 38  1  0  0  0  0
 18 38  1  0  0  0  0
 38 39  1  1  0  0  0
 39 40  2  0  0  0  0
 38 41  1  0  0  0  0
 41 42  1  0  0  0  0
 11 42  1  0  0  0  0
  9 43  1  0  0  0  0
  2 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0085404

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@]2(O)[C@]3([H])CC[C@]4(O)C[C@H](CC[C@]4(C=O)[C@@]3([H])[C@H](O)C[C@]12C)O[C@@H]1O[C@H](C)[C@H](O)[C@@H](O)[C@H]1O)C1=CC(=O)OC1

> <INCHI_IDENTIFIER>
InChI=1S/C29H42O11/c1-14-22(33)23(34)24(35)25(39-14)40-16-3-6-27(13-30)21-18(4-7-28(27,36)10-16)29(37)8-5-17(15-9-20(32)38-12-15)26(29,2)11-19(21)31/h9,13-14,16-19,21-25,31,33-37H,3-8,10-12H2,1-2H3/t14-,16+,17-,18-,19-,21-,22+,23-,24-,25+,26-,27+,28+,29+/m1/s1

> <INCHI_KEY>
AZOXLPPOBHVORY-DKHHQGSCSA-N

> <FORMULA>
C29H42O11

> <MOLECULAR_WEIGHT>
566.644

> <EXACT_MASS>
566.272712172

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
58.5769040994139

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,5S,7S,10R,11S,14R,15R,17R)-7,11,17-trihydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)-5-{[(2R,3R,4R,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-2-carbaldehyde

> <ALOGPS_LOGP>
-0.71

> <JCHEM_LOGP>
-1.164353313333334

> <ALOGPS_LOGS>
-2.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.212662989550353

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.181446879195222

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8535571639079027

> <JCHEM_POLAR_SURFACE_AREA>
183.20999999999998

> <JCHEM_REFRACTIVITY>
138.37899999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.55e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5S,7S,10R,11S,14R,15R,17R)-7,11,17-trihydroxy-15-methyl-14-(5-oxo-2H-furan-3-yl)-5-{[(2R,3R,4R,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-2-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0     -10.717  -0.270   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.201   0.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.677   1.450   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -9.670   2.627   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -7.162   1.721   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -6.638   3.169   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -6.169   0.544   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -4.653   0.815   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -6.692  -0.905   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -5.699  -2.082   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -4.183  -1.811   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.191  -2.988   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.675  -2.717   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.682  -3.895   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.834  -3.624   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.357  -2.175   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0       1.881  -0.727   0.000  0.00  0.00           H+0
HETATM   18  C   UNK     0       0.365  -0.998   0.000  0.00  0.00           C+0
HETATM   19  H   UNK     0      -0.159  -2.446   0.000  0.00  0.00           H+0
HETATM   20  C   UNK     0       0.888   0.451   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.105   1.628   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.404   0.722   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.396  -0.456   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.068   0.930   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.873  -1.904   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.504  -3.399   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.089  -2.849   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.364  -1.985   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.936  -0.506   0.000  0.00  0.00           C+0
HETATM   30  H   UNK     0       6.448  -0.796   0.000  0.00  0.00           H+0
HETATM   31  C   UNK     0       5.881   0.710   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.453   2.189   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.727   3.054   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       7.943   2.108   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       7.420   0.660   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       6.777   4.593   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -2.198  -4.166   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -1.151  -1.269   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -0.628   0.179   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -1.621   1.357   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -2.144  -0.092   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -3.660  -0.363   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -8.208  -1.176   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   43                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   43                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   42                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   37   38                                             
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   25                                             
CONECT   17   16                                                            
CONECT   18   16   19   20   38                                             
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   25   29                                             
CONECT   24   23                                                            
CONECT   25   23   16   26   27                                             
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   23   30   31                                             
CONECT   30   29                                                            
CONECT   31   29   32   35                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34   31                                                       
CONECT   36   33                                                            
CONECT   37   13                                                            
CONECT   38   13   18   39   41                                             
CONECT   39   38   40                                                       
CONECT   40   39                                                            
CONECT   41   38   42                                                       
CONECT   42   41   11                                                       
CONECT   43    9    2                                                       
MASTER        0    0    0    0    0    0    0    0   43    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₂O₁₁

Average Mass

566.6440 Da

Monoisotopic Mass

566.27271 Da

IUPAC Name

(1S,2S,5S,7S,10R,11S,14R,15R,17R)-7,11,17-trihydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)-5-{[(2R,3R,4R,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-2-carbaldehyde

Traditional Name

(1S,2S,5S,7S,10R,11S,14R,15R,17R)-7,11,17-trihydroxy-15-methyl-14-(5-oxo-2H-furan-3-yl)-5-{[(2R,3R,4R,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-2-carbaldehyde

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@]2(O)[C@]3([H])CC[C@]4(O)C[C@H](CC[C@]4(C=O)[C@@]3([H])[C@H](O)C[C@]12C)O[C@@H]1O[C@H](C)[C@H](O)[C@@H](O)[C@H]1O)C1=CC(=O)OC1

InChI Identifier

InChI=1S/C29H42O11/c1-14-22(33)23(34)24(35)25(39-14)40-16-3-6-27(13-30)21-18(4-7-28(27,36)10-16)29(37)8-5-17(15-9-20(32)38-12-15)26(29,2)11-19(21)31/h9,13-14,16-19,21-25,31,33-37H,3-8,10-12H2,1-2H3/t14-,16+,17-,18-,19-,21-,22+,23-,24-,25+,26-,27+,28+,29+/m1/s1

InChI Key

AZOXLPPOBHVORY-DKHHQGSCSA-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
Convallaria majalis	Plant	KNApSAcK
Crossopetalum gaumeri	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cardenolide glycosides and derivatives. Cardenolide glycosides and derivatives are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Cardenolide glycosides and derivatives

Alternative Parents

Substituents

Cardanolide-glycoside
Steroidal glycoside
19-oxosteroid
14-hydroxysteroid
5-hydroxysteroid
Hydroxysteroid
11-hydroxysteroid
11-alpha-hydroxysteroid
Oxosteroid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
2-furanone
Monosaccharide
Oxane
Enoate ester
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Dihydrofuran
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Polyol
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Aldehyde
Organic oxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Alcohol
Organooxygen compound
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	-0.71	ALOGPS
logP	-1.2	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	7.18	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	183.21 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	138.38 m³·mol⁻¹	ChemAxon
Polarizability	58.58 Å³	ChemAxon
Number of Rings	6	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

C00055245

Chemspider ID

8778426

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10603058

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Canescein (NP0085404)

MOL for NP0085404 (Canescein)

3D MOL for NP0085404 (Canescein)

3D SDF for NP0085404 (Canescein)

3D-SDF for NP0085404 (Canescein)

PDB for NP0085404 (Canescein)

3D PDB for NP0085404 (Canescein)

SMILES for NP0085404 (Canescein)

INCHI for NP0085404 (Canescein)

Structure for NP0085404 (Canescein)

3D Structure for NP0085404 (Canescein)