NP-MRD: Showing NP-Card for Taccalonolide B (NP0140899)

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Record Information

Version

2.0

Created at

2022-06-29 21:57:32 UTC

Updated at

2022-06-29 21:57:32 UTC

NP-MRD ID

NP0140899

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Taccalonolide B

Description

Taccalonolide b belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring. Thus, taccalonolide b is considered to be a sterol. Taccalonolide B is found in Tacca chantrieri and Tacca plantaginea. Taccalonolide B was first documented in 2011 (PMID: 22040100). Based on a literature review very few articles have been published on Taccalonolide b (PMID: 23855953).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292223572D          

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M  END

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M  END


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    6.0905    2.0961    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2692    2.0181    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0895    1.2129    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7998    0.7932    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8777   -0.0281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3024    0.9659    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6949    1.5241    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8745    2.3293    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6617    2.5763    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8413    3.3815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9236    4.1017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2846    3.3824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4135    4.7449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2670    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4467    3.6927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8392    4.2509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2338    3.9397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9077    1.2771    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7281    0.4719    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9409    0.2249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3334    0.7830    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5131    1.5882    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3002    1.8353    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4799    2.6405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8724    3.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0520    4.0038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0852    2.9516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7259    1.3412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3356   -0.0863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1559   -0.8915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1227    0.1607    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7302   -0.3975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0874    2.0823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5320    2.8001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7162    0.5723    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5033    0.8193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1658    0.3277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5116    1.6443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1033    0.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8711   -0.2380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8183    0.5343    0.0000 C   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  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  7  6  1  1  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  6  0  0  0
 12  9  1  6  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 14 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  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  6  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 28 34  1  6  0  0  0
 27 34  1  6  0  0  0
 25 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 12 37  1  0  0  0  0
 37 38  1  1  0  0  0
 24 39  1  1  0  0  0
  8 40  1  1  0  0  0
  5 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 42 44  1  0  0  0  0
  4 44  1  0  0  0  0
 41 45  1  6  0  0  0
 41 46  1  1  0  0  0
  5 47  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0140899

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C=C2OC(=O)[C@@](C)(O)[C@]2(C)[C@@H]2[C@H](O)[C@H]3[C@@H]4[C@@H](O)C(=O)[C@H]5C[C@@H]6O[C@@H]6[C@H](OC(C)=O)[C@]5(C)[C@H]4[C@H](OC(C)=O)[C@H](OC(C)=O)[C@]3(C)[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C34H44O13/c1-11-9-17-33(7,34(8,42)30(41)47-17)22-19(11)32(6)20(25(22)40)18-21(27(43-12(2)35)29(32)45-14(4)37)31(5)15(23(38)24(18)39)10-16-26(46-16)28(31)44-13(3)36/h9,11,15-16,18-22,24-29,39-40,42H,10H2,1-8H3/t11-,15-,16+,18+,19+,20-,21-,22+,24-,25-,26+,27+,28+,29+,31+,32-,33+,34-/m1/s1

> <INCHI_KEY>
FFQOXBQSZPYHSA-MPOUNFKCSA-N

> <FORMULA>
C34H44O13

> <MOLECULAR_WEIGHT>
660.713

> <EXACT_MASS>
660.278191477

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      11.674   6.563   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.287   5.149   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.816   4.973   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.429   3.560   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.511   2.323   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.981   2.500   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.369   3.913   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.836   3.767   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.500   2.264   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.826   1.481   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.972  -0.052   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.031   1.803   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.897   2.845   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.232   4.348   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.702   4.809   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.037   6.312   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.324   7.657   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.131   6.314   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.238   8.857   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.098   5.390   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.434   6.893   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.300   7.935   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.903   7.354   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.428   2.384   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.092   0.881   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.623   0.420   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.489   1.462   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.824   2.965   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.294   3.426   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.629   4.929   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.495   5.971   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.830   7.474   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.026   5.510   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.355   2.504   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       6.226  -0.161   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       5.891  -1.664   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       7.696   0.300   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       8.830  -0.742   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       5.763   3.887   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      10.326   5.227   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      14.403   1.068   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      15.873   1.529   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      17.110   0.612   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      15.888   3.069   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      13.259   0.037   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      14.693  -0.444   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      12.727   0.997   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   44                                                  
CONECT    5    4    6   41   47                                             
CONECT    6    5    7   10                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9   15   40                                             
CONECT    9    8   10   12                                                  
CONECT   10    9    6   11                                                  
CONECT   11   10                                                            
CONECT   12    9   13   37                                                  
CONECT   13   12   14   24                                                  
CONECT   14   13   15   20                                                  
CONECT   15   14    8   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   14   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   13   25   29   39                                             
CONECT   25   24   26   35                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   34                                                  
CONECT   28   27   29   34                                                  
CONECT   29   28   24   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   28   27                                                       
CONECT   35   25   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   12   38                                                  
CONECT   38   37                                                            
CONECT   39   24                                                            
CONECT   40    8                                                            
CONECT   41    5   42   45   46                                             
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42    4                                                       
CONECT   45   41                                                            
CONECT   46   41                                                            
CONECT   47    5                                                            
MASTER        0    0    0    0    0    0    0    0   47    0  106    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₄H₄₄O₁₃

Average Mass

660.7130 Da

Monoisotopic Mass

660.27819 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@@H]1C=C2OC(=O)[C@@](C)(O)[C@]2(C)[C@@H]2[C@H](O)[C@H]3[C@@H]4[C@@H](O)C(=O)[C@H]5C[C@@H]6O[C@@H]6[C@H](OC(C)=O)[C@]5(C)[C@H]4[C@H](OC(C)=O)[C@H](OC(C)=O)[C@]3(C)[C@@H]12

InChI Identifier

InChI=1S/C34H44O13/c1-11-9-17-33(7,34(8,42)30(41)47-17)22-19(11)32(6)20(25(22)40)18-21(27(43-12(2)35)29(32)45-14(4)37)31(5)15(23(38)24(18)39)10-16-26(46-16)28(31)44-13(3)36/h9,11,15-16,18-22,24-29,39-40,42H,10H2,1-8H3/t11-,15-,16+,18+,19+,20-,21-,22+,24-,25-,26+,27+,28+,29+,31+,32-,33+,34-/m1/s1

InChI Key

FFQOXBQSZPYHSA-MPOUNFKCSA-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
Tacca chantrieri	LOTUS Database	35616633
Tacca plantaginea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Withanolides and derivatives

Alternative Parents

Substituents

Withanolide-skeleton
Steroid ester
15-hydroxysteroid
Hydroxysteroid
Oxosteroid
6-oxosteroid
7-hydroxysteroid
Tetracarboxylic acid or derivatives
Oxepane
Cyclic alcohol
Enol ester
Tertiary alcohol
Tetrahydrofuran
Secondary alcohol
Carboxylic acid ester
Ketone
Lactone
Carboxylic acid derivative
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Oxacycle
Polyol
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
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

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

26617558

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

56662029

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li J, Peng J, Risinger AL, Mooberry SL: Hydrolysis reactions of the taccalonolides reveal structure-activity relationships. J Nat Prod. 2013 Jul 26;76(7):1369-75. doi: 10.1021/np400435t. Epub 2013 Jul 15. [PubMed:23855953 ]
Li J, Risinger AL, Peng J, Chen Z, Hu L, Mooberry SL: Potent taccalonolides, AF and AJ, inform significant structure-activity relationships and tubulin as the binding site of these microtubule stabilizers. J Am Chem Soc. 2011 Nov 30;133(47):19064-7. doi: 10.1021/ja209045k. Epub 2011 Nov 8. [PubMed:22040100 ]

Showing NP-Card for Taccalonolide B (NP0140899)

MOL for NP0140899 (Taccalonolide B)

3D MOL for NP0140899 (Taccalonolide B)

3D SDF for NP0140899 (Taccalonolide B)

3D-SDF for NP0140899 (Taccalonolide B)

PDB for NP0140899 (Taccalonolide B)

3D PDB for NP0140899 (Taccalonolide B)

SMILES for NP0140899 (Taccalonolide B)

INCHI for NP0140899 (Taccalonolide B)

Structure for NP0140899 (Taccalonolide B)

3D Structure for NP0140899 (Taccalonolide B)