NP-MRD: Showing NP-Card for Cimiracemoside C (NP0140911)

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Record Information

Version

2.0

Created at

2022-06-29 21:58:07 UTC

Updated at

2022-06-29 21:58:07 UTC

NP-MRD ID

NP0140911

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cimiracemoside C

Description

Cimiracemoside C, also known as cimigenol 3AAP, belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus. Cimiracemoside C is found in Actaea cimicifuga, Actaea dahurica and Actaea racemosa. Cimiracemoside C was first documented in 2006 (PMID: 16637680). Based on a literature review a small amount of articles have been published on Cimiracemoside C (PMID: 28985643) (PMID: 25022210).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292223582D          

 44 51  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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 23 76  1  0
M  END


  Mrv1652306292223582D          

 44 51  0  0  1  0            999 V2000
    3.5040   -1.8774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8245   -1.1172    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6688   -0.9831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9722   -0.1764    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0823    0.6793    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2898    1.0490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6479    0.4189    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3228   -0.4074    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4904   -0.3740    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9195   -0.9696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1183   -0.7730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8880    0.0192    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3171   -0.5763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0868    0.2159    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4841   -0.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2854   -0.1831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5157    0.6091    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9448    1.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1436    1.0081    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4273    1.6036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2286    1.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4589    0.6148    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2590    0.4218    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9446    0.8942    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9409    1.7192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1086    1.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5201    1.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7762    2.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3169    0.8058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5472    1.5980    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3485    1.7946    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5788    2.5868    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0079    3.1824    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2067    2.9857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9763    2.1935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2382    3.9746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3800    2.7834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9194    1.1990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7989   -1.1392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2771    0.0917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8050    1.0771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5278    1.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2029    0.3544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4072    1.7999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  2  8  1  0  0  0  0
  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
 12 13  1  6  0  0  0
 14 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 22 21  1  1  0  0  0
 12 22  1  0  0  0  0
 22 23  1  0  0  0  0
  9 23  1  0  0  0  0
 23 24  1  0  0  0  0
  7 24  1  0  0  0  0
 24 25  1  1  0  0  0
 23 26  1  1  0  0  0
 18 27  1  0  0  0  0
 18 28  1  0  0  0  0
 17 29  1  6  0  0  0
 30 29  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  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
 30 35  1  0  0  0  0
 33 36  1  1  0  0  0
 32 37  1  1  0  0  0
 31 38  1  6  0  0  0
  9 39  1  6  0  0  0
  7 40  1  6  0  0  0
  4 40  1  6  0  0  0
  5 41  1  6  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 41 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0140911

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@H]2O[C@@]3(O[C@@H]2C(C)(C)O)[C@H](O)[C@@]2(C)[C@@H]4CC[C@@H]5[C@]6(C[C@@]46CC[C@]2(C)[C@@H]13)CC[C@H](O[C@@H]1OC[C@H](O)[C@H](O)[C@H]1O)C5(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C35H56O9/c1-17-14-19-26(30(4,5)40)44-35(43-19)25(17)31(6)12-13-34-16-33(34)11-10-22(42-27-24(38)23(37)18(36)15-41-27)29(2,3)20(33)8-9-21(34)32(31,7)28(35)39/h17-28,36-40H,8-16H2,1-7H3/t17-,18+,19-,20+,21+,22+,23+,24-,25-,26+,27+,28-,31-,32-,33-,34+,35+/m1/s1

> <INCHI_KEY>
BTPYUWOBZFGKAI-BKJHYQRZSA-N

> <FORMULA>
C35H56O9

> <MOLECULAR_WEIGHT>
620.824

> <EXACT_MASS>
620.392433383

$$$$

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       6.541  -3.504   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.139  -2.085   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.715  -1.835   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.282  -0.329   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.487   1.268   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.008   1.958   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.809   0.782   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.203  -0.760   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.649  -0.698   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.583  -1.810   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.087  -1.443   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.658   0.036   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.592  -1.076   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.162   0.403   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.904  -0.709   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.399  -0.342   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.829   1.137   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.764   2.249   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.268   1.882   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.798   2.993   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.293   2.626   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.723   1.148   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.217   0.787   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.497   1.669   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.490   3.209   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.936   2.302   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.837   3.353   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.449   3.756   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -4.325   1.504   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -4.755   2.983   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -6.250   3.350   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -6.680   4.829   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -5.615   5.940   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -4.119   5.573   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -3.689   4.095   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -6.045   7.419   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -8.176   5.196   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -7.316   2.238   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       5.225  -2.126   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       7.984   0.171   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      10.836   2.011   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      12.185   2.753   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      11.579   0.662   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      10.093   3.360   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   40                                                  
CONECT    5    4    6   41                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   24   40                                             
CONECT    8    7    2    9                                                  
CONECT    9    8   10   23   39                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   22                                             
CONECT   13   12   14                                                       
CONECT   14   13   12   15   19                                             
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   29                                                  
CONECT   18   17   19   27   28                                             
CONECT   19   18   14   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   12   23                                                  
CONECT   23   22    9   24   26                                             
CONECT   24   23    7   25                                                  
CONECT   25   24                                                            
CONECT   26   23                                                            
CONECT   27   18                                                            
CONECT   28   18                                                            
CONECT   29   17   30                                                       
CONECT   30   29   31   35                                                  
CONECT   31   30   32   38                                                  
CONECT   32   31   33   37                                                  
CONECT   33   32   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34   30                                                       
CONECT   36   33                                                            
CONECT   37   32                                                            
CONECT   38   31                                                            
CONECT   39    9                                                            
CONECT   40    7    4                                                       
CONECT   41    5   42   43   44                                             
CONECT   42   41                                                            
CONECT   43   41                                                            
CONECT   44   41                                                            
MASTER        0    0    0    0    0    0    0    0   44    0  102    0
END

View in JSmol

Synonyms

Value	Source
Cimigenol 3aap	MeSH
Cimigenol 3-O-alpha-L-arabinopyranoside	MeSH

Chemical Formula

C₃₅H₅₆O₉

Average Mass

620.8240 Da

Monoisotopic Mass

620.39243 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@H]2O[C@@]3(O[C@@H]2C(C)(C)O)[C@H](O)[C@@]2(C)[C@@H]4CC[C@@H]5[C@]6(C[C@@]46CC[C@]2(C)[C@@H]13)CC[C@H](O[C@@H]1OC[C@H](O)[C@H](O)[C@H]1O)C5(C)C

InChI Identifier

InChI=1S/C35H56O9/c1-17-14-19-26(30(4,5)40)44-35(43-19)25(17)31(6)12-13-34-16-33(34)11-10-22(42-27-24(38)23(37)18(36)15-41-27)29(2,3)20(33)8-9-21(34)32(31,7)28(35)39/h17-28,36-40H,8-16H2,1-7H3/t17-,18+,19-,20+,21+,22+,23+,24-,25-,26+,27+,28-,31-,32-,33-,34+,35+/m1/s1

InChI Key

BTPYUWOBZFGKAI-BKJHYQRZSA-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
Actaea cimicifuga	LOTUS Database	35616633
Actaea dahurica	LOTUS Database	35616633
Actaea racemosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Cucurbitacin glycosides

Alternative Parents

Substituents

Cucurbitacin glycoside skeleton
Cycloartanol-skeleton
9b,19-cyclo-lanostane-skeleton
Cycloartane-skeleton
Triterpenoid
15-hydroxysteroid
Hydroxysteroid
Glycosyl compound
O-glycosyl compound
Oxepane
Ketal
Oxane
Monosaccharide
Cyclic alcohol
Tertiary alcohol
Meta-dioxolane
Secondary alcohol
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Organooxygen compound
Alcohol
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

28424402

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15541911

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tankeu S, Vermaak I, Chen W, Sandasi M, Kamatou G, Viljoen A: Hyperspectral Imaging and Support Vector Machine: A Powerful Combination to Differentiate Black Cohosh (Actaea racemosa) from Other Cohosh Species. Planta Med. 2018 Apr;84(6-07):407-419. doi: 10.1055/s-0043-119887. Epub 2017 Oct 6. [PubMed:28985643 ]
Moser C, Vickers SP, Brammer R, Cheetham SC, Drewe J: Antidiabetic effects of the Cimicifuga racemosa extract Ze 450 in vitro and in vivo in ob/ob mice. Phytomedicine. 2014 Sep 25;21(11):1382-9. doi: 10.1016/j.phymed.2014.06.002. Epub 2014 Jul 8. [PubMed:25022210 ]
Jiang B, Kronenberg F, Nuntanakorn P, Qiu MH, Kennelly EJ: Evaluation of the botanical authenticity and phytochemical profile of black cohosh products by high-performance liquid chromatography with selected ion monitoring liquid chromatography-mass spectrometry. J Agric Food Chem. 2006 May 3;54(9):3242-53. doi: 10.1021/jf0606149. [PubMed:16637680 ]

Showing NP-Card for Cimiracemoside C (NP0140911)

MOL for NP0140911 (Cimiracemoside C)

3D MOL for NP0140911 (Cimiracemoside C)

3D SDF for NP0140911 (Cimiracemoside C)

3D-SDF for NP0140911 (Cimiracemoside C)

PDB for NP0140911 (Cimiracemoside C)

3D PDB for NP0140911 (Cimiracemoside C)

SMILES for NP0140911 (Cimiracemoside C)

INCHI for NP0140911 (Cimiracemoside C)

Structure for NP0140911 (Cimiracemoside C)

3D Structure for NP0140911 (Cimiracemoside C)