NP-MRD: Showing NP-Card for (2s,3r,4s,5s,6r)-2-{[(2r,3r,4s,5s,6r)-4,5-dihydroxy-2-{[1-(1-hydroxy-5-methylhex-4-en-1-yl)-9a-(hydroxymethyl)-3a,3b-dimethyl-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0245029)

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Record Information

Version

2.0

Created at

2022-09-07 05:57:35 UTC

Updated at

2022-09-07 05:57:35 UTC

NP-MRD ID

NP0245029

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5s,6r)-2-{[(2r,3r,4s,5s,6r)-4,5-dihydroxy-2-{[1-(1-hydroxy-5-methylhex-4-en-1-yl)-9a-(hydroxymethyl)-3a,3b-dimethyl-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Description

(2S,3R,4S,5S,6R)-2-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-2-{[14-(1-hydroxy-5-methylhex-4-en-1-yl)-2-(hydroxymethyl)-10,11-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-5-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)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-{[(2r,3r,4s,5s,6r)-4,5-dihydroxy-2-{[1-(1-hydroxy-5-methylhex-4-en-1-yl)-9a-(hydroxymethyl)-3a,3b-dimethyl-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)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-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-2-{[14-(1-hydroxy-5-methylhex-4-en-1-yl)-2-(hydroxymethyl)-10,11-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-5-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072207572D          

 52 57  0  0  1  0            999 V2000
   -3.0459   -1.0035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2287   -0.8906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9178   -0.1264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7223   -1.5419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9051   -1.4291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3987   -2.0804    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
    0.7294   -1.2034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9249   -2.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6955   -3.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    2.2812   -1.9614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0934   -2.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3737   -2.8825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1858   -3.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9055   -2.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4373   -1.6211    0.0000 O   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
    7.1540   -2.8327    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8737   -2.0567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4055   -1.4260    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1252   -0.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6570   -0.0194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2176   -1.5712    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7494   -0.9405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4979   -2.3472    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.3100   -2.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9661   -2.9779    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2464   -3.7538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0585   -3.8990    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.5903   -3.2683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4024   -3.4135    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.9342   -2.7828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6540   -2.0069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6827   -4.1894    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.4948   -4.3347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1509   -4.8202    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.4312   -5.5961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3388   -4.6749    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.8070   -5.3057    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
    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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  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
  7  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
 12 14  1  0  0  0  0
  9 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
 19 20  1  0  0  0  0
 18 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
 25 24  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  1  0  0  0  0
 27 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
 25 34  1  0  0  0  0
 34 35  1  1  0  0  0
 36 35  1  6  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  6  0  0  0
 39 40  1  0  0  0  0
 38 41  1  0  0  0  0
 41 42  1  1  0  0  0
 41 43  1  0  0  0  0
 43 44  1  6  0  0  0
 43 45  1  0  0  0  0
 36 45  1  0  0  0  0
 45 46  1  1  0  0  0
 23 47  1  0  0  0  0
 47 48  1  0  0  0  0
 18 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
 17 51  1  0  0  0  0
 12 51  1  0  0  0  0
 51 52  1  0  0  0  0
M  END

     RDKit          3D

118123  0  0  0  0  0  0  0  0999 V2000
   11.1162   -0.1342    1.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7233   -0.2608    1.6744 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3936   -1.4494    2.5219 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8447    0.6632    1.3771 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4436    0.6900    1.8070 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4404    0.6765    0.6571 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6206   -0.5714   -0.1370 C   0  0  1  0  0  0  0  0  0  0  0  0
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    5.7638    0.3781   -2.3113 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3571    0.9664   -2.4409 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5061   -0.2289   -2.0689 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5810   -1.2205   -3.1901 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2659   -0.6852   -0.8283 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6168   -1.9716   -0.4422 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2574   -1.5037    0.1446 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3997   -0.8638   -0.9069 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0998   -0.4303   -0.2920 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0310   -0.9678   -1.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8546   -2.3751   -1.2130 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1519   -1.0874    1.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0392   -0.3392    1.9784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9099    0.7243    1.4367 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2316    0.2201    1.4364 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0923    0.9299    2.2304 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4408    0.1310    3.3612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0853    0.9511    4.2974 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3801    0.0540    5.4863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2072   -0.9821    5.0031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4072    1.4859    3.7932 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.9602    2.2839    4.7595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1342    2.2258    2.4786 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.3660    2.6324    1.9976 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.9189    0.7142   -0.5665 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -6.9485   -1.1174   -2.1522 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.8254   -1.5341   -1.1577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2582    0.3056   -2.5721 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6251    0.6632   -3.7363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0051    1.2400   -1.4361 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.1865    1.3138   -0.6685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5071    1.3369    0.1499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0189    1.0313   -0.0315 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6042    1.9725   -0.9762 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0359    1.5571   -1.2494 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.1824   -0.4555    0.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1864    1.3339   -3.4546 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4282   -0.7531   -4.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.1118    3.2006    4.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
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 39101  1  0
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 41103  1  6
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 43105  1  6
 44106  1  0
 45107  1  6
 46108  1  0
M  END


  Mrv1652309072207572D          

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  2  3  1  0  0  0  0
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  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
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
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  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
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 16 17  1  0  0  0  0
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 25 26  1  0  0  0  0
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 27 30  1  0  0  0  0
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 50 51  1  0  0  0  0
 17 51  1  0  0  0  0
 12 51  1  0  0  0  0
 51 52  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0245029

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCCC(O)C1CCC2(C)C1CCC1C2(C)CCC2CC(CCC12CO)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C39H66O13/c1-20(2)6-5-7-25(43)23-12-14-37(3)24(23)8-9-28-38(37,4)13-10-21-16-22(11-15-39(21,28)19-42)49-36-34(32(47)30(45)27(18-41)51-36)52-35-33(48)31(46)29(44)26(17-40)50-35/h6,21-36,40-48H,5,7-19H2,1-4H3/t21?,22?,23?,24?,25?,26-,27-,28?,29-,30-,31+,32+,33-,34-,35+,36-,37?,38?,39?/m1/s1

> <INCHI_KEY>
VNXIXXWLGRKKST-QLRGAEDESA-N

> <FORMULA>
C39H66O13

> <MOLECULAR_WEIGHT>
742.944

> <EXACT_MASS>
742.450342185

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
118

> <JCHEM_AVERAGE_POLARIZABILITY>
83.65493347948825

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-2-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-2-{[14-(1-hydroxy-5-methylhex-4-en-1-yl)-2-(hydroxymethyl)-10,11-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_LOGP>
0.9947098093333318

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.700613227970916

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.089851426942873

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7378118705149449

> <JCHEM_POLAR_SURFACE_AREA>
218.98999999999995

> <JCHEM_REFRACTIVITY>
188.73680000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-2-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-2-{[14-(1-hydroxy-5-methylhex-4-en-1-yl)-2-(hydroxymethyl)-10,11-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)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      -5.686  -1.873   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.160  -1.662   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.580  -0.236   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.215  -2.878   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.690  -2.668   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.744  -3.883   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.781  -3.673   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.362  -2.246   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.726  -4.889   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.298  -6.368   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.573  -7.232   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.789  -6.287   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.158  -7.782   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.266  -4.839   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.258  -3.661   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.774  -3.932   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.297  -5.381   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.813  -5.652   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.290  -4.203   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.283  -3.026   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.806  -4.474   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.322  -4.746   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.845  -6.194   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      12.361  -6.465   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      13.354  -5.288   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      12.831  -3.839   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      13.824  -2.662   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.300  -1.214   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      14.293  -0.036   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      15.340  -2.933   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      16.332  -1.756   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      15.863  -4.381   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      17.379  -4.652   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      14.870  -5.559   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      15.393  -7.007   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      16.909  -7.278   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      17.902  -6.101   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      19.418  -6.372   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      20.411  -5.195   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      19.887  -3.746   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      19.941  -7.820   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      21.457  -8.091   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      18.948  -8.998   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      19.472 -10.446   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      17.432  -8.727   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      16.440  -9.904   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0       9.853  -7.371   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       8.337  -7.100   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       7.344  -8.277   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       5.828  -8.006   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       5.305  -6.558   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       4.724  -7.984   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   51                                             
CONECT   13   12                                                            
CONECT   14   12    9   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   51                                                  
CONECT   18   17   19   21   48                                             
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   47                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   34                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   25   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   45                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   41                                                  
CONECT   39   38   40                                                       
CONECT   40   39                                                            
CONECT   41   38   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   36   46                                                  
CONECT   46   45                                                            
CONECT   47   23   48                                                       
CONECT   48   47   18   49                                                  
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   17   12   52                                             
CONECT   52   51                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  114    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₉H₆₆O₁₃

Average Mass

742.9440 Da

Monoisotopic Mass

742.45034 Da

IUPAC Name

(2S,3R,4S,5S,6R)-2-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-2-{[14-(1-hydroxy-5-methylhex-4-en-1-yl)-2-(hydroxymethyl)-10,11-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(C)=CCCC(O)C1CCC2(C)C1CCC1C2(C)CCC2CC(CCC12CO)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C39H66O13/c1-20(2)6-5-7-25(43)23-12-14-37(3)24(23)8-9-28-38(37,4)13-10-21-16-22(11-15-39(21,28)19-42)49-36-34(32(47)30(45)27(18-41)51-36)52-35-33(48)31(46)29(44)26(17-40)50-35/h6,21-36,40-48H,5,7-19H2,1-4H3/t21?,22?,23?,24?,25?,26-,27-,28?,29-,30-,31+,32+,33-,34-,35+,36-,37?,38?,39?/m1/s1

InChI Key

VNXIXXWLGRKKST-QLRGAEDESA-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
20-hydroxysteroid
Diterpenoid
19-hydroxysteroid
Hydroxysteroid
Terpene glycoside
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
Alkyl glycoside
O-glycosyl compound
Glycosyl compound
Disaccharide
Fatty alcohol
Oxane
Fatty acyl
Secondary alcohol
Organoheterocyclic compound
Polyol
Acetal
Oxacycle
Primary alcohol
Organic oxygen compound
Hydrocarbon derivative
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	0.99	ChemAxon
pKa (Strongest Acidic)	12.09	ChemAxon
pKa (Strongest Basic)	-0.74	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	11	ChemAxon
Refractivity	188.74 m³·mol⁻¹	ChemAxon
Polarizability	83.65 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

10142400

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11968574

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-{[(2r,3r,4s,5s,6r)-4,5-dihydroxy-2-{[1-(1-hydroxy-5-methylhex-4-en-1-yl)-9a-(hydroxymethyl)-3a,3b-dimethyl-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0245029)

MOL for NP0245029 ((2s,3r,4s,5s,6r)-2-{[(2r,3r,4s,5s,6r)-4,5-dihydroxy-2-{[1-(1-hydroxy-5-methylhex-4-en-1-yl)-9a-(hydroxymethyl)-3a,3b-dimethyl-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0245029 ((2s,3r,4s,5s,6r)-2-{[(2r,3r,4s,5s,6r)-4,5-dihydroxy-2-{[1-(1-hydroxy-5-methylhex-4-en-1-yl)-9a-(hydroxymethyl)-3a,3b-dimethyl-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0245029 ((2s,3r,4s,5s,6r)-2-{[(2r,3r,4s,5s,6r)-4,5-dihydroxy-2-{[1-(1-hydroxy-5-methylhex-4-en-1-yl)-9a-(hydroxymethyl)-3a,3b-dimethyl-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0245029 ((2s,3r,4s,5s,6r)-2-{[(2r,3r,4s,5s,6r)-4,5-dihydroxy-2-{[1-(1-hydroxy-5-methylhex-4-en-1-yl)-9a-(hydroxymethyl)-3a,3b-dimethyl-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0245029 ((2s,3r,4s,5s,6r)-2-{[(2r,3r,4s,5s,6r)-4,5-dihydroxy-2-{[1-(1-hydroxy-5-methylhex-4-en-1-yl)-9a-(hydroxymethyl)-3a,3b-dimethyl-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0245029 ((2s,3r,4s,5s,6r)-2-{[(2r,3r,4s,5s,6r)-4,5-dihydroxy-2-{[1-(1-hydroxy-5-methylhex-4-en-1-yl)-9a-(hydroxymethyl)-3a,3b-dimethyl-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0245029 ((2s,3r,4s,5s,6r)-2-{[(2r,3r,4s,5s,6r)-4,5-dihydroxy-2-{[1-(1-hydroxy-5-methylhex-4-en-1-yl)-9a-(hydroxymethyl)-3a,3b-dimethyl-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0245029 ((2s,3r,4s,5s,6r)-2-{[(2r,3r,4s,5s,6r)-4,5-dihydroxy-2-{[1-(1-hydroxy-5-methylhex-4-en-1-yl)-9a-(hydroxymethyl)-3a,3b-dimethyl-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0245029 ((2s,3r,4s,5s,6r)-2-{[(2r,3r,4s,5s,6r)-4,5-dihydroxy-2-{[1-(1-hydroxy-5-methylhex-4-en-1-yl)-9a-(hydroxymethyl)-3a,3b-dimethyl-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0245029 ((2s,3r,4s,5s,6r)-2-{[(2r,3r,4s,5s,6r)-4,5-dihydroxy-2-{[1-(1-hydroxy-5-methylhex-4-en-1-yl)-9a-(hydroxymethyl)-3a,3b-dimethyl-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)