NP-MRD: Showing NP-Card for (+)-Cheiranthoside V (NP0077555)

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Record Information

Version

2.0

Created at

2022-04-28 22:41:13 UTC

Updated at

2022-04-28 22:41:13 UTC

NP-MRD ID

NP0077555

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Cheiranthoside V

Description

(2R,3R,4S,6R)-3-{[(2S,3R,4R,5R,6S)-3,4-dihydroxy-6-methyl-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-{[(1S,2S,5S,7S,10R,11S,14R,15R)-2-formyl-7,11-dihydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-5-yl]oxy}-2-methyloxan-4-yl acetate 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. (+)-Cheiranthoside V is found in Erysimum cheiranthoides and Erysimum chelranthoides. Based on a literature review very few articles have been published on (2R,3R,4S,6R)-3-{[(2S,3R,4R,5R,6S)-3,4-dihydroxy-6-methyl-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-{[(1S,2S,5S,7S,10R,11S,14R,15R)-2-formyl-7,11-dihydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-5-yl]oxy}-2-methyloxan-4-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292200412D          

 62 69  0  0  1  0            999 V2000
    2.6190   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.1221    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8705    0.7528    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6826    0.6076    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9629   -0.1684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4311   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -0.1416    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0168    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939   -0.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1184   -0.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3987   -1.5420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1912   -1.7713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7474   -2.0484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0646   -1.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3228   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4850    1.4085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463    1.0432    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5266    0.2673    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9948   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.5577    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4342    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9098    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1901    1.4789    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0022    1.6241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2825    2.4000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7507    3.0307    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9385    2.8855    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6582    2.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4067    3.5162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6870    4.2921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4991    4.4373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0310    3.8066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8431    3.9518    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1234    4.7278    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9355    4.8730    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4673    4.2423    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1870    3.4663    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3749    3.3211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7188    2.8356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2794    4.3875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8113    3.7568    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5310    2.9809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0628    2.3501    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.8749    2.4954    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.1552    3.2713    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.6234    3.9020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.9037    4.6779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9673    3.4165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4067    1.8647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7825    1.5742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3143    0.9435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2158    5.6489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5916    5.3585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0946    2.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8069   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2751   -1.1393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9660    1.8191    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  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  7 10  1  6  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
  5 16  1  6  0  0  0
  4 17  1  6  0  0  0
  3 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  2 21  1  0  0  0  0
 21 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
 20 25  1  0  0  0  0
 24 26  1  6  0  0  0
 27 26  1  6  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
 27 32  1  0  0  0  0
 31 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 30 37  1  1  0  0  0
 38 37  1  6  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 38 43  1  0  0  0  0
 42 44  1  1  0  0  0
 41 45  1  6  0  0  0
 46 45  1  1  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 46 51  1  0  0  0  0
 51 52  1  1  0  0  0
 50 53  1  6  0  0  0
 49 54  1  1  0  0  0
 48 55  1  6  0  0  0
 55 56  1  0  0  0  0
 40 57  1  6  0  0  0
 39 58  1  1  0  0  0
 29 59  1  6  0  0  0
 21 60  1  6  0  0  0
 60 61  2  0  0  0  0
 20 62  1  6  0  0  0
M  END

     RDKit          3D

126133  0  0  0  0  0  0  0  0999 V2000
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   -4.0597   -1.7896   -2.0561 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9666   -1.5639   -0.4353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4339   -0.3419   -1.1731 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7792    0.0696   -0.6425 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8461   -0.0909   -1.5103 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4501    1.2319   -1.8555 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9492    1.0556   -1.9770 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4810    0.7772   -0.6022 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1679    1.9368    0.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.0703   -1.0579   -1.5995 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304292200412D          

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M  END
> <DATABASE_ID>
NP0077555

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C43H64O19/c1-19-36(61-38-35(52)33(50)37(20(2)57-38)62-39-34(51)32(49)31(48)28(16-44)60-39)27(58-21(3)46)14-30(56-19)59-23-5-10-41(18-45)25-6-9-40(4)24(22-13-29(47)55-17-22)8-12-43(40,54)26(25)7-11-42(41,53)15-23/h13,18-20,23-28,30-39,44,48-54H,5-12,14-17H2,1-4H3/t19-,20+,23+,24-,25+,26-,27+,28-,30+,31-,32+,33-,34-,35-,36-,37+,38+,39-,40-,41+,42+,43+/m1/s1

> <INCHI_KEY>
BXXHNQDTEFIKSJ-ULBQNUCPSA-N

> <FORMULA>
C43H64O19

> <MOLECULAR_WEIGHT>
884.966

> <EXACT_MASS>
884.404179841

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
126

> <JCHEM_AVERAGE_POLARIZABILITY>
90.82355810112597

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.05

> <JCHEM_LOGP>
-1.0085863676666673

> <ALOGPS_LOGS>
-3.02

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.939165267003785

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.1826285803834065

> <JCHEM_PKA_STRONGEST_BASIC>
0.26896009723720404

> <JCHEM_POLAR_SURFACE_AREA>
286.89

> <JCHEM_REFRACTIVITY>
207.71020000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.50e-01 g/l

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

> <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       4.889  -1.221   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.366   0.228   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.358   1.405   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.874   1.134   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.398  -0.314   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.405  -1.492   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.937  -0.264   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.365   1.215   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.090   2.079   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.882  -1.480   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.421  -1.430   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.944  -2.878   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      13.424  -3.306   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      10.728  -3.824   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.454  -2.959   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.069  -1.700   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.505   2.629   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.835   2.854   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.319   3.125   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.326   1.947   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.850   0.499   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.857  -0.678   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.341  -0.407   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.182   1.041   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.810   2.218   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.698   1.312   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.221   2.761   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -3.737   3.032   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -4.261   4.480   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -3.268   5.657   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.752   5.386   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.229   3.938   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -0.759   6.564   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -1.282   8.012   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -2.798   8.283   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -0.290   9.189   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -3.791   7.106   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -5.307   7.377   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -5.830   8.825   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -7.346   9.096   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -8.339   7.919   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -7.816   6.471   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -6.300   6.199   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      -8.809   5.293   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      -9.855   8.190   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0     -10.848   7.013   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0     -10.324   5.564   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0     -11.317   4.387   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0     -12.833   4.658   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0     -13.356   6.106   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0     -12.364   7.284   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0     -12.887   8.732   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0     -14.872   6.377   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0     -13.826   3.481   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0     -10.794   2.939   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0     -11.787   1.761   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      -7.869  10.545   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0      -4.838  10.002   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0      -5.777   4.751   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       3.373  -0.949   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0       2.380  -2.127   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0       1.803   3.396   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   21                                                  
CONECT    3    2    4   18                                                  
CONECT    4    3    5    9   17                                             
CONECT    5    4    6    7   16                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    7   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   10                                                       
CONECT   16    5                                                            
CONECT   17    4                                                            
CONECT   18    3   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   25   62                                             
CONECT   21   20    2   22   60                                             
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24   20                                                       
CONECT   26   24   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   59                                                  
CONECT   30   29   31   37                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31   27                                                       
CONECT   33   31   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   30   38                                                       
CONECT   38   37   39   43                                                  
CONECT   39   38   40   58                                                  
CONECT   40   39   41   57                                                  
CONECT   41   40   42   45                                                  
CONECT   42   41   43   44                                                  
CONECT   43   42   38                                                       
CONECT   44   42                                                            
CONECT   45   41   46                                                       
CONECT   46   45   47   51                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49   55                                                  
CONECT   49   48   50   54                                                  
CONECT   50   49   51   53                                                  
CONECT   51   50   46   52                                                  
CONECT   52   51                                                            
CONECT   53   50                                                            
CONECT   54   49                                                            
CONECT   55   48   56                                                       
CONECT   56   55                                                            
CONECT   57   40                                                            
CONECT   58   39                                                            
CONECT   59   29                                                            
CONECT   60   21   61                                                       
CONECT   61   60                                                            
CONECT   62   20                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  138    0
END

View in JSmol

Synonyms

Value	Source
(2R,3R,4S,6R)-3-{[(2S,3R,4R,5R,6S)-3,4-dihydroxy-6-methyl-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-{[(1S,2S,5S,7S,10R,11S,14R,15R)-2-formyl-7,11-dihydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0,.0,]heptadecan-5-yl]oxy}-2-methyloxan-4-yl acetic acid	Generator

Chemical Formula

C₄₃H₆₄O₁₉

Average Mass

884.9660 Da

Monoisotopic Mass

884.40418 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C43H64O19/c1-19-36(61-38-35(52)33(50)37(20(2)57-38)62-39-34(51)32(49)31(48)28(16-44)60-39)27(58-21(3)46)14-30(56-19)59-23-5-10-41(18-45)25-6-9-40(4)24(22-13-29(47)55-17-22)8-12-43(40,54)26(25)7-11-42(41,53)15-23/h13,18-20,23-28,30-39,44,48-54H,5-12,14-17H2,1-4H3/t19-,20+,23+,24-,25+,26-,27+,28-,30+,31-,32+,33-,34-,35-,36-,37+,38+,39-,40-,41+,42+,43+/m1/s1

InChI Key

BXXHNQDTEFIKSJ-ULBQNUCPSA-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
Erysimum cheiranthoides	LOTUS Database	35616633
Erysimum chelranthoides	Plant	KNApSAcK

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
Oligosaccharide
19-oxosteroid
Oxosteroid
Hydroxysteroid
5-hydroxysteroid
14-hydroxysteroid
O-glycosyl compound
Glycosyl compound
Oxane
Dicarboxylic acid or derivatives
2-furanone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Dihydrofuran
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Aldehyde
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	-1	ALOGPS
logP	-1	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	7.18	ChemAxon
pKa (Strongest Basic)	0.27	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	286.89 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	207.71 m³·mol⁻¹	ChemAxon
Polarizability	90.82 Å³	ChemAxon
Number of Rings	8	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

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

162920926

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (+)-Cheiranthoside V (NP0077555)

MOL for NP0077555 ((+)-Cheiranthoside V)

3D MOL for NP0077555 ((+)-Cheiranthoside V)

3D SDF for NP0077555 ((+)-Cheiranthoside V)

3D-SDF for NP0077555 ((+)-Cheiranthoside V)

PDB for NP0077555 ((+)-Cheiranthoside V)

3D PDB for NP0077555 ((+)-Cheiranthoside V)

SMILES for NP0077555 ((+)-Cheiranthoside V)

INCHI for NP0077555 ((+)-Cheiranthoside V)

Structure for NP0077555 ((+)-Cheiranthoside V)

3D Structure for NP0077555 ((+)-Cheiranthoside V)