NP-MRD: Showing NP-Card for (2s,3r,4s,5s,6r)-2-{[(5e)-2-{7,11-dihydroxy-3a,3b,6,6-tetramethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl}-7-hydroxy-6-methylhept-5-en-2-yl]oxy}-6-({[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol (NP0239091)

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Record Information

Version

2.0

Created at

2022-09-06 22:36:00 UTC

Updated at

2022-09-06 22:36:00 UTC

NP-MRD ID

NP0239091

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5s,6r)-2-{[(5e)-2-{7,11-dihydroxy-3a,3b,6,6-tetramethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl}-7-hydroxy-6-methylhept-5-en-2-yl]oxy}-6-({[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol

Description

(2S,3R,4S,5S,6R)-2-{[(5E)-2-{5,16-dihydroxy-6,6,10,11-tetramethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-14-yl}-7-hydroxy-6-methylhept-5-en-2-yl]oxy}-6-({[(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton. (2s,3r,4s,5s,6r)-2-{[(5e)-2-{7,11-dihydroxy-3a,3b,6,6-tetramethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl}-7-hydroxy-6-methylhept-5-en-2-yl]oxy}-6-({[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol is found in Gynostemma pentaphyllum. Based on a literature review very few articles have been published on (2S,3R,4S,5S,6R)-2-{[(5E)-2-{5,16-dihydroxy-6,6,10,11-tetramethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-14-yl}-7-hydroxy-6-methylhept-5-en-2-yl]oxy}-6-({[(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072200362D          

 53 58  0  0  1  0            999 V2000
    0.8448    0.9763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3512    0.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0403   -0.4392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2230   -0.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0879   -1.3162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4185   -1.9676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0698   -1.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2328   -2.4739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9970   -2.1630    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1099   -1.3458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8740   -1.0349    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9869   -0.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7511    0.0933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8639    0.9105    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6281    1.2214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7410    2.0386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0896    2.5450    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2025    3.3622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3254    2.2341    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -2.4125   -2.3585    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0638   -2.8648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6483   -2.6694    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.3784   -3.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0297   -3.3680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2274   -4.1690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7494   -2.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1858   -3.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7176   -2.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5297   -2.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8100   -3.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6221   -3.4634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2782   -3.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9917   -4.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9942   -4.7234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4661   -3.8037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9343   -4.4344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1221   -4.2891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8418   -3.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5309   -4.2774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1684    0.4378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6748   -0.2135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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
  6  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 14 13  1  1  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  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 14 21  1  0  0  0  0
 21 22  1  1  0  0  0
 11 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
  9 27  1  0  0  0  0
 27 28  1  6  0  0  0
  6 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
 32 34  1  0  0  0  0
 29 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  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
 42 44  1  0  0  0  0
 44 45  1  0  0  0  0
 44 46  1  0  0  0  0
 44 47  1  0  0  0  0
 39 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
 38 50  1  0  0  0  0
 32 50  1  0  0  0  0
 50 51  1  0  0  0  0
  2 52  1  0  0  0  0
 52 53  1  0  0  0  0
M  END

     RDKit          3D

121126  0  0  0  0  0  0  0  0999 V2000
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    4.0658    1.3512   -0.5139 C   0  0  2  0  0  0  0  0  0  0  0  0
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    6.6019    2.0182    0.8433 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5391    1.4860   -0.0182 O   0  0  0  0  0  0  0  0  0  0  0  0
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 51116  1  0
 51117  1  0
 51118  1  0
M  END


  Mrv1652309072200362D          

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    2.2274   -4.1690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6748   -0.2135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
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 17 18  1  1  0  0  0
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 19 20  1  6  0  0  0
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 21 22  1  1  0  0  0
 11 23  1  0  0  0  0
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 27 28  1  6  0  0  0
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 29 30  1  0  0  0  0
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 44 46  1  0  0  0  0
 44 47  1  0  0  0  0
 39 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
 38 50  1  0  0  0  0
 32 50  1  0  0  0  0
 50 51  1  0  0  0  0
  2 52  1  0  0  0  0
 52 53  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0239091

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(CO)=C/CCC(C)(O[C@@H]1O[C@H](CO[C@H]2OC[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O)C1CCC2(C)C1C(O)CC1C3CCC(O)C(C)(C)C3CCC21C

> <INCHI_IDENTIFIER>
InChI=1S/C40H68O13/c1-20(17-41)8-7-13-40(6,53-36-34(49)32(47)31(46)27(52-36)19-51-35-33(48)30(45)26(43)18-50-35)23-12-15-39(5)29(23)25(42)16-24-21-9-10-28(44)37(2,3)22(21)11-14-38(24,39)4/h8,21-36,41-49H,7,9-19H2,1-6H3/b20-8+/t21?,22?,23?,24?,25?,26-,27-,28?,29?,30+,31-,32+,33-,34-,35-,36+,38?,39?,40?/m1/s1

> <INCHI_KEY>
OYAIGUDDJQAZSC-AHSKFEOESA-N

> <FORMULA>
C40H68O13

> <MOLECULAR_WEIGHT>
756.971

> <EXACT_MASS>
756.46599225

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
121

> <JCHEM_AVERAGE_POLARIZABILITY>
84.07613316438554

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-2-{[(5E)-2-{5,16-dihydroxy-6,6,10,11-tetramethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}-7-hydroxy-6-methylhept-5-en-2-yl]oxy}-6-({[(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol

> <JCHEM_LOGP>
1.0397831789999996

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.460671131138728

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.92742353896847

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8322514305872496

> <JCHEM_POLAR_SURFACE_AREA>
218.98999999999998

> <JCHEM_REFRACTIVITY>
193.39960000000013

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-2-{[(5E)-2-{5,16-dihydroxy-6,6,10,11-tetramethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}-7-hydroxy-6-methylhept-5-en-2-yl]oxy}-6-({[(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       1.577   1.822   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.522   0.607   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.942  -0.820   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.416  -1.030   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.164  -2.457   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.781  -3.673   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.997  -2.728   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.435  -4.618   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.861  -4.038   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.072  -2.512   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.498  -1.932   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.709  -0.406   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -5.135   0.174   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -5.346   1.700   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -6.772   2.280   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -6.983   3.805   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.767   4.751   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.978   6.276   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -4.341   4.170   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -3.125   5.116   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -4.130   2.645   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.704   2.064   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -4.714  -2.877   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -6.140  -2.297   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -4.503  -4.403   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -5.719  -5.348   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -3.077  -4.983   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -2.866  -6.508   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.726  -4.889   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.298  -6.368   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.573  -7.232   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.789  -6.287   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.158  -7.782   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.266  -4.839   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.258  -3.661   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       3.735  -2.213   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       5.774  -3.932   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.297  -5.381   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       7.813  -5.652   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       8.806  -4.474   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      10.322  -4.746   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      10.845  -6.194   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      12.361  -6.465   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       9.853  -7.371   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      11.184  -8.144   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       9.322  -8.817   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       8.337  -7.100   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       7.344  -8.277   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       5.828  -8.006   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       5.305  -6.558   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       4.724  -7.984   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       4.048   0.817   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0       4.993  -0.399   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   52                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   29                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   27                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   23                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   14   22                                                  
CONECT   22   21                                                            
CONECT   23   11   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25    9   28                                                  
CONECT   28   27                                                            
CONECT   29    6   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34   50                                             
CONECT   33   32                                                            
CONECT   34   32   29   35                                                  
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   39   50                                                  
CONECT   39   38   40   47                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45   46   47                                             
CONECT   45   44                                                            
CONECT   46   44                                                            
CONECT   47   44   39   48                                                  
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   38   32   51                                             
CONECT   51   50                                                            
CONECT   52    2   53                                                       
CONECT   53   52                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  116    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₀H₆₈O₁₃

Average Mass

756.9710 Da

Monoisotopic Mass

756.46599 Da

IUPAC Name

(2S,3R,4S,5S,6R)-2-{[(5E)-2-{5,16-dihydroxy-6,6,10,11-tetramethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}-7-hydroxy-6-methylhept-5-en-2-yl]oxy}-6-({[(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol

Traditional Name

CAS Registry Number

Not Available

SMILES

C\C(CO)=C/CCC(C)(O[C@@H]1O[C@H](CO[C@H]2OC[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O)C1CCC2(C)C1C(O)CC1C3CCC(O)C(C)(C)C3CCC21C

InChI Identifier

InChI=1S/C40H68O13/c1-20(17-41)8-7-13-40(6,53-36-34(49)32(47)31(46)27(52-36)19-51-35-33(48)30(45)26(43)18-50-35)23-12-15-39(5)29(23)25(42)16-24-21-9-10-28(44)37(2,3)22(21)11-14-38(24,39)4/h8,21-36,41-49H,7,9-19H2,1-6H3/b20-8+/t21?,22?,23?,24?,25?,26-,27-,28?,29?,30+,31-,32+,33-,34-,35-,36+,38?,39?,40?/m1/s1

InChI Key

OYAIGUDDJQAZSC-AHSKFEOESA-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
Gynostemma pentaphyllum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroidal glycosides

Alternative Parents

Substituents

Diterpene glycoside
Steroidal glycoside
26-hydroxysteroid
Diterpenoid
Hydroxysteroid
12-hydroxysteroid
3-hydroxysteroid
Terpene glycoside
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
Alkyl glycoside
O-glycosyl compound
Glycosyl compound
Disaccharide
Fatty alcohol
Fatty acyl
Oxane
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
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	1.04	ChemAxon
pKa (Strongest Acidic)	11.93	ChemAxon
pKa (Strongest Basic)	-0.83	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	218.99 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	193.4 m³·mol⁻¹	ChemAxon
Polarizability	84.08 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	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

10142361

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11968535

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4s,5s,6r)-2-{[(5e)-2-{7,11-dihydroxy-3a,3b,6,6-tetramethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl}-7-hydroxy-6-methylhept-5-en-2-yl]oxy}-6-({[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol (NP0239091)

MOL for NP0239091 ((2s,3r,4s,5s,6r)-2-{[(5e)-2-{7,11-dihydroxy-3a,3b,6,6-tetramethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl}-7-hydroxy-6-methylhept-5-en-2-yl]oxy}-6-({[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol)

3D MOL for NP0239091 ((2s,3r,4s,5s,6r)-2-{[(5e)-2-{7,11-dihydroxy-3a,3b,6,6-tetramethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl}-7-hydroxy-6-methylhept-5-en-2-yl]oxy}-6-({[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol)

3D SDF for NP0239091 ((2s,3r,4s,5s,6r)-2-{[(5e)-2-{7,11-dihydroxy-3a,3b,6,6-tetramethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl}-7-hydroxy-6-methylhept-5-en-2-yl]oxy}-6-({[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol)

3D-SDF for NP0239091 ((2s,3r,4s,5s,6r)-2-{[(5e)-2-{7,11-dihydroxy-3a,3b,6,6-tetramethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl}-7-hydroxy-6-methylhept-5-en-2-yl]oxy}-6-({[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol)

PDB for NP0239091 ((2s,3r,4s,5s,6r)-2-{[(5e)-2-{7,11-dihydroxy-3a,3b,6,6-tetramethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl}-7-hydroxy-6-methylhept-5-en-2-yl]oxy}-6-({[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol)

3D PDB for NP0239091 ((2s,3r,4s,5s,6r)-2-{[(5e)-2-{7,11-dihydroxy-3a,3b,6,6-tetramethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl}-7-hydroxy-6-methylhept-5-en-2-yl]oxy}-6-({[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol)

SMILES for NP0239091 ((2s,3r,4s,5s,6r)-2-{[(5e)-2-{7,11-dihydroxy-3a,3b,6,6-tetramethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl}-7-hydroxy-6-methylhept-5-en-2-yl]oxy}-6-({[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol)

INCHI for NP0239091 ((2s,3r,4s,5s,6r)-2-{[(5e)-2-{7,11-dihydroxy-3a,3b,6,6-tetramethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl}-7-hydroxy-6-methylhept-5-en-2-yl]oxy}-6-({[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol)

Structure for NP0239091 ((2s,3r,4s,5s,6r)-2-{[(5e)-2-{7,11-dihydroxy-3a,3b,6,6-tetramethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl}-7-hydroxy-6-methylhept-5-en-2-yl]oxy}-6-({[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol)

3D Structure for NP0239091 ((2s,3r,4s,5s,6r)-2-{[(5e)-2-{7,11-dihydroxy-3a,3b,6,6-tetramethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl}-7-hydroxy-6-methylhept-5-en-2-yl]oxy}-6-({[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol)