NP-MRD: Showing NP-Card for chamuvarinin (NP0190810)

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Record Information

Version

2.0

Created at

2022-09-04 07:33:09 UTC

Updated at

2022-09-04 07:33:09 UTC

NP-MRD ID

NP0190810

Secondary Accession Numbers

None

Natural Product Identification

Common Name

chamuvarinin

Description

Chamuvarinin belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. chamuvarinin is found in Uvaria chamae. chamuvarinin was first documented in 2013 (PMID: 23630031). Based on a literature review a small amount of articles have been published on chamuvarinin (PMID: 31598093) (PMID: 30295489) (PMID: 28185724) (PMID: 25145275).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042209332D          

 43 46  0  0  1  0            999 V2000
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  7 43  1  0  0  0  0
M  END

     RDKit          3D

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 18 75  1  0
 19 76  1  6
 20 77  1  6
 21 78  1  0
 22 79  1  0
 22 80  1  0
 23 81  1  0
 23 82  1  0
 24 83  1  0
 24 84  1  0
 25 85  1  0
 25 86  1  0
 26 87  1  0
 26 88  1  0
 27 89  1  0
 27 90  1  0
 28 91  1  0
 28 92  1  0
 29 93  1  0
 29 94  1  0
 30 95  1  0
 30 96  1  0
 31 97  1  0
 31 98  1  0
 32 99  1  0
 32100  1  0
 33101  1  0
 33102  1  0
 35103  1  0
 36104  1  6
 37105  1  0
 37106  1  0
 37107  1  0
M  END


  Mrv1652309042209332D          

 43 46  0  0  1  0            999 V2000
    8.0155   -8.2065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8440   -7.3996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0594   -7.1446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8878   -6.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1032   -6.0827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9317   -5.2757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1471   -5.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5340   -5.5728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7494   -5.3179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5778   -4.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1909   -3.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0194   -3.1519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2657   -2.8164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3520   -1.9959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1589   -1.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4945   -1.0707    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0820   -0.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6340    0.2569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3877   -0.0787    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1022    0.3338    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1022    1.1588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8166   -0.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5311    0.3338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2456   -0.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9601    0.3338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6745   -0.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3890    0.3338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1035   -0.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8179    0.3338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5324   -0.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2469    0.3338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9613   -0.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6758    0.3338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3903   -0.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1440    0.2569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6960   -0.3562    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.5165   -0.2700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2835   -1.0707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4765   -0.8992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8634   -1.4512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3015   -0.8992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5714   -2.5388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9755   -4.2138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  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
  7  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  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  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  0  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
 29 30  1  0  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  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  6  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 34 39  1  0  0  0  0
 39 40  2  0  0  0  0
 19 41  1  0  0  0  0
 16 41  1  0  0  0  0
 15 42  1  0  0  0  0
 12 42  1  0  0  0  0
 11 43  1  0  0  0  0
  7 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0190810

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCC1CCCC(O1)C1CCC(O1)[C@H]1CC[C@@H](O1)[C@H](O)CCCCCCCCCCCCC1=C[C@H](C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C37H64O6/c1-3-4-5-15-19-30-20-17-22-33(41-30)34-25-26-36(43-34)35-24-23-32(42-35)31(38)21-16-13-11-9-7-6-8-10-12-14-18-29-27-28(2)40-37(29)39/h27-28,30-36,38H,3-26H2,1-2H3/t28-,30?,31+,32+,33?,34?,35+,36?/m0/s1

> <INCHI_KEY>
IWOYCFRIFNMRSY-PWPZFVDCSA-N

> <FORMULA>
C37H64O6

> <MOLECULAR_WEIGHT>
604.913

> <EXACT_MASS>
604.470289781

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
107

> <JCHEM_AVERAGE_POLARIZABILITY>
76.32503206866822

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S)-3-[(13R)-13-[(2R,5R)-5'-(6-hexyloxan-2-yl)-[2,2'-bioxolane]-5-yl]-13-hydroxytridecyl]-5-methyl-2,5-dihydrofuran-2-one

> <JCHEM_LOGP>
9.843895505666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.274396947056978

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.396556335524586

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1486650941839613

> <JCHEM_POLAR_SURFACE_AREA>
74.22000000000001

> <JCHEM_REFRACTIVITY>
172.8865

> <JCHEM_ROTATABLE_BOND_COUNT>
21

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(5S)-3-[(13R)-13-[(2R,5R)-5'-(6-hexyloxan-2-yl)-[2,2'-bioxolane]-5-yl]-13-hydroxytridecyl]-5-methyl-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      14.962 -15.319   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.642 -13.813   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.177 -13.337   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.857 -11.830   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.393 -11.354   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.072  -9.848   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.608  -9.372   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.463 -10.403   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.999  -9.927   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.679  -8.420   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.823  -7.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.503  -5.884   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.096  -5.257   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.257  -3.726   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.763  -3.405   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.390  -1.999   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.620  -0.665   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.650   0.480   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.057  -0.147   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.391   0.623   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      11.391   2.163   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      12.724  -0.147   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.058   0.623   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.392  -0.147   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.725   0.623   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      18.059  -0.147   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      19.393   0.623   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      20.726  -0.147   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      22.060   0.623   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      23.394  -0.147   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      24.728   0.623   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      26.061  -0.147   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      27.395   0.623   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      28.729  -0.147   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      30.135   0.480   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      31.166  -0.665   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      32.697  -0.504   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      30.396  -1.999   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      28.890  -1.678   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      27.745  -2.709   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       9.896  -1.678   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       8.533  -4.739   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       9.288  -7.866   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   43                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   43                                                  
CONECT   12   11   13   42                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   42                                                  
CONECT   16   15   17   41                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   41                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   39                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   34   40                                                  
CONECT   40   39                                                            
CONECT   41   19   16                                                       
CONECT   42   15   12                                                       
CONECT   43   11    7                                                       
MASTER        0    0    0    0    0    0    0    0   43    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₇H₆₄O₆

Average Mass

604.9130 Da

Monoisotopic Mass

604.47029 Da

IUPAC Name

(5S)-3-[(13R)-13-[(2R,5R)-5'-(6-hexyloxan-2-yl)-[2,2'-bioxolane]-5-yl]-13-hydroxytridecyl]-5-methyl-2,5-dihydrofuran-2-one

Traditional Name

(5S)-3-[(13R)-13-[(2R,5R)-5'-(6-hexyloxan-2-yl)-[2,2'-bioxolane]-5-yl]-13-hydroxytridecyl]-5-methyl-5H-furan-2-one

CAS Registry Number

Not Available

SMILES

CCCCCCC1CCCC(O1)C1CCC(O1)[C@H]1CC[C@@H](O1)[C@H](O)CCCCCCCCCCCCC1=C[C@H](C)OC1=O

InChI Identifier

InChI=1S/C37H64O6/c1-3-4-5-15-19-30-20-17-22-33(41-30)34-25-26-36(43-34)35-24-23-32(42-35)31(38)21-16-13-11-9-7-6-8-10-12-14-18-29-27-28(2)40-37(29)39/h27-28,30-36,38H,3-26H2,1-2H3/t28-,30?,31+,32+,33?,34?,35+,36?/m0/s1

InChI Key

IWOYCFRIFNMRSY-PWPZFVDCSA-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
Uvaria chamae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Annonaceous acetogenins

Alternative Parents

Substituents

Annonaceae acetogenin skeleton
Long chain fatty alcohol
2-furanone
Oxane
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Oxolane
Carboxylic acid ester
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organooxygen compound
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	9.84	ChemAxon
pKa (Strongest Acidic)	13.4	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.22 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	172.89 m³·mol⁻¹	ChemAxon
Polarizability	76.33 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

9517397

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Chamuvarinin

METLIN ID

Not Available

PubChem Compound

11342455

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zacharova MK, Tulloch LB, Gould ER, Fraser AL, King EF, Menzies SK, Smith TK, Florence GJ: Structure-Based Design, Synthesis and Biological Evaluation of Bis-Tetrahydropyran Furan Acetogenin Mimics Targeting the Trypanosomatid F1 Component of ATP Synthase. European J Org Chem. 2019 Sep 1;2019(31-32):5434-5440. doi: 10.1002/ejoc.201900541. Epub 2019 May 29. [PubMed:31598093 ]
Samala M, Lu TN, Mandava S, Hwang J, Bogonda G, Kim D, Park H, Kim D, Lee J: Stereoselective Protection-Free Asymmetric Total Synthesis of (+)-Chamuvarinin, a Potent Anticancer and Antitrypanosomal Agent: Substrate-Controlled Construction of the Adjacently Linked Oxatricyclic Core by Internal Alkylation. Org Lett. 2018 Oct 19;20(20):6398-6402. doi: 10.1021/acs.orglett.8b02706. Epub 2018 Oct 8. [PubMed:30295489 ]
Gould ER, King EFB, Menzies SK, Fraser AL, Tulloch LB, Zacharova MK, Smith TK, Florence GJ: Simplifying nature: Towards the design of broad spectrum kinetoplastid inhibitors, inspired by acetogenins. Bioorg Med Chem. 2017 Nov 15;25(22):6126-6136. doi: 10.1016/j.bmc.2017.01.021. Epub 2017 Jan 28. [PubMed:28185724 ]
Florence GJ, Fraser AL, Gould ER, King EF, Menzies SK, Morris JC, Tulloch LB, Smith TK: Non-natural acetogenin analogues as potent Trypanosoma brucei inhibitors. ChemMedChem. 2014 Nov;9(11):2548-56. doi: 10.1002/cmdc.201402272. Epub 2014 Aug 21. [PubMed:25145275 ]
Florence GJ, Morris JC, Murray RG, Vanga RR, Osler JD, Smith TK: Total synthesis, stereochemical assignment, and biological activity of chamuvarinin and structural analogues. Chemistry. 2013 Jun 17;19(25):8309-20. doi: 10.1002/chem.201204527. Epub 2013 Apr 29. [PubMed:23630031 ]
LOTUS database [Link]

Showing NP-Card for chamuvarinin (NP0190810)

MOL for NP0190810 (chamuvarinin)

3D MOL for NP0190810 (chamuvarinin)

3D SDF for NP0190810 (chamuvarinin)

3D-SDF for NP0190810 (chamuvarinin)

PDB for NP0190810 (chamuvarinin)

3D PDB for NP0190810 (chamuvarinin)

SMILES for NP0190810 (chamuvarinin)

INCHI for NP0190810 (chamuvarinin)

Structure for NP0190810 (chamuvarinin)

3D Structure for NP0190810 (chamuvarinin)