NP-MRD: Showing NP-Card for (2s,3r,4s,5r)-2-{[(2s,3s,4ar,4bs,7r,8as)-7-{[(2r,3r,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-ethenyl-2,4b,8,8-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-3h-phenanthren-3-yl]oxy}oxane-3,4,5-triol (NP0191864)

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Record Information

Version

2.0

Created at

2022-09-04 08:57:10 UTC

Updated at

2022-09-04 08:57:10 UTC

NP-MRD ID

NP0191864

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5r)-2-{[(2s,3s,4ar,4bs,7r,8as)-7-{[(2r,3r,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-ethenyl-2,4b,8,8-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-3h-phenanthren-3-yl]oxy}oxane-3,4,5-triol

Description

Marginatoside A belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. (2s,3r,4s,5r)-2-{[(2s,3s,4ar,4bs,7r,8as)-7-{[(2r,3r,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-ethenyl-2,4b,8,8-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-3h-phenanthren-3-yl]oxy}oxane-3,4,5-triol is found in Microlepia marginata. Based on a literature review very few articles have been published on Marginatoside A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042210572D          

 40 44  0  0  1  0            999 V2000
    1.5442    0.5178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4009   -0.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4009   -1.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.1105    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6021    0.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5206    0.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9829   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3954   -1.5395    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2159   -1.6257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3874   -2.4327    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.1411   -2.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2273   -3.5887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6729   -2.8452    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    7.0598   -2.2931    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2529   -2.4647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5079   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0954   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.4454   -1.5395    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0329   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -2.2539    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.0296   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2671   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0296   -1.5395    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4421   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954   -1.5395    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2079   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  6  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 15 22  1  0  0  0  0
 22 23  1  1  0  0  0
 13 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  9 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28  6  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
  3 30  1  0  0  0  0
 30 31  1  6  0  0  0
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 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
 32 39  1  0  0  0  0
 39 40  1  1  0  0  0
M  END

     RDKit          3D

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    1.3245   -1.4524   -0.1339 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -6.9515    3.0188    1.4556 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -7.3640    1.5630    1.5890 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -7.1471    0.9523   -0.6825 O   0  0  0  0  0  0  0  0  0  0  0  0
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 30  3  1  0
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 21 66  1  0
 22 67  1  1
 23 68  1  0
M  END


  Mrv1652309042210572D          

 40 44  0  0  1  0            999 V2000
    1.5442    0.5178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4009   -0.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.4454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.1105    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    5.6021    0.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5206    0.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9829   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3954   -1.5395    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2159   -1.6257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3874   -2.4327    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.1411   -2.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2273   -3.5887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6729   -2.8452    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5867   -3.6657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0598   -2.2931    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2529   -2.4647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0954   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2704   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -1.5395    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0329   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -2.2539    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7954   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0296   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4421   -2.2539    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2671   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0296   -1.5395    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4421   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954   -1.5395    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2079   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  6  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 15 22  1  0  0  0  0
 22 23  1  1  0  0  0
 13 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  9 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28  6  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
  3 30  1  0  0  0  0
 30 31  1  6  0  0  0
 32 31  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
 32 39  1  0  0  0  0
 39 40  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0191864

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)[C@@H](CC[C@@]2(C)[C@@H]3C[C@H](O[C@@H]4OC[C@@H](O)[C@H](O)[C@H]4O)[C@@](C)(C=C)C=C3CC[C@H]12)O[C@@H]1O[C@@H](CO)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O10/c1-6-29(4)12-15-7-8-19-28(2,3)20(39-27-25(36)23(34)18(13-31)38-27)9-10-30(19,5)16(15)11-21(29)40-26-24(35)22(33)17(32)14-37-26/h6,12,16-27,31-36H,1,7-11,13-14H2,2-5H3/t16-,17-,18+,19-,20-,21+,22+,23+,24-,25-,26+,27+,29+,30+/m1/s1

> <INCHI_KEY>
VUECSBXQKFKTMK-AZQUCDCQSA-N

> <FORMULA>
C30H48O10

> <MOLECULAR_WEIGHT>
568.704

> <EXACT_MASS>
568.324747746

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
88

> <JCHEM_AVERAGE_POLARIZABILITY>
61.58894635477053

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5R)-2-{[(2S,3S,4aR,4bS,7R,8aS)-7-{[(2R,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-ethenyl-2,4b,8,8-tetramethyl-2,3,4,4a,4b,5,6,7,8,8a,9,10-dodecahydrophenanthren-3-yl]oxy}oxane-3,4,5-triol

> <JCHEM_LOGP>
1.1328684386666663

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.521113994341235

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.96026109615213

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9811434595471207

> <JCHEM_POLAR_SURFACE_AREA>
158.3

> <JCHEM_REFRACTIVITY>
144.55020000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5R)-2-{[(2S,3S,4aR,4bS,7R,8aS)-7-{[(2R,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-ethenyl-2,4b,8,8-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthren-3-yl]oxy}oxane-3,4,5-triol

> <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       2.882   0.966   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.615  -0.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.795  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.615  -2.530   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.565  -0.206   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.105  -0.206   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.875   1.127   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.415   1.127   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.185  -0.206   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.725  -0.206   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.457   1.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.172   0.320   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.495  -1.540   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      13.035  -1.540   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      13.805  -2.874   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      15.336  -3.035   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      15.656  -4.541   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.063  -5.167   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      17.224  -6.699   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      14.323  -5.311   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      14.162  -6.843   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      13.178  -4.281   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      11.672  -4.601   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      10.725  -2.874   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.185  -2.874   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.415  -1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.645  -2.874   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.875  -1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.105  -2.874   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.565  -2.874   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.795  -4.207   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.255  -4.207   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       1.485  -5.541   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -0.055  -5.541   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.825  -4.207   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -2.365  -4.207   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -0.055  -2.874   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -0.825  -1.540   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       1.485  -2.874   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       2.255  -1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   30                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   28                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   26                                                  
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10   14   24                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   15   23                                                  
CONECT   23   22                                                            
CONECT   24   13   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25    9   27   28                                             
CONECT   27   26                                                            
CONECT   28   26    6   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29    3   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   39                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   32   40                                                  
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₈O₁₀

Average Mass

568.7040 Da

Monoisotopic Mass

568.32475 Da

IUPAC Name

(2S,3R,4S,5R)-2-{[(2S,3S,4aR,4bS,7R,8aS)-7-{[(2R,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-ethenyl-2,4b,8,8-tetramethyl-2,3,4,4a,4b,5,6,7,8,8a,9,10-dodecahydrophenanthren-3-yl]oxy}oxane-3,4,5-triol

Traditional Name

(2S,3R,4S,5R)-2-{[(2S,3S,4aR,4bS,7R,8aS)-7-{[(2R,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-ethenyl-2,4b,8,8-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthren-3-yl]oxy}oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

CC1(C)[C@@H](CC[C@@]2(C)[C@@H]3C[C@H](O[C@@H]4OC[C@@H](O)[C@H](O)[C@H]4O)[C@@](C)(C=C)C=C3CC[C@H]12)O[C@@H]1O[C@@H](CO)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C30H48O10/c1-6-29(4)12-15-7-8-19-28(2,3)20(39-27-25(36)23(34)18(13-31)38-27)9-10-30(19,5)16(15)11-21(29)40-26-24(35)22(33)17(32)14-37-26/h6,12,16-27,31-36H,1,7-11,13-14H2,2-5H3/t16-,17-,18+,19-,20-,21+,22+,23+,24-,25-,26+,27+,29+,30+/m1/s1

InChI Key

VUECSBXQKFKTMK-AZQUCDCQSA-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
Microlepia marginata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Diterpene glycosides

Alternative Parents

Substituents

Diterpene glycoside
Diterpenoid
Pimarane diterpenoid
Phenanthrene
Hydrophenanthrene
O-glycosyl compound
Glycosyl compound
Oxane
Monosaccharide
Oxolane
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Organic oxygen compound
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
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	1.13	ChemAxon
pKa (Strongest Acidic)	11.96	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	158.3 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	144.55 m³·mol⁻¹	ChemAxon
Polarizability	61.59 Å³	ChemAxon
Number of Rings	5	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

C00051485

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

101647899

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,5r)-2-{[(2s,3s,4ar,4bs,7r,8as)-7-{[(2r,3r,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-ethenyl-2,4b,8,8-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-3h-phenanthren-3-yl]oxy}oxane-3,4,5-triol (NP0191864)

MOL for NP0191864 ((2s,3r,4s,5r)-2-{[(2s,3s,4ar,4bs,7r,8as)-7-{[(2r,3r,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-ethenyl-2,4b,8,8-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-3h-phenanthren-3-yl]oxy}oxane-3,4,5-triol)

3D MOL for NP0191864 ((2s,3r,4s,5r)-2-{[(2s,3s,4ar,4bs,7r,8as)-7-{[(2r,3r,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-ethenyl-2,4b,8,8-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-3h-phenanthren-3-yl]oxy}oxane-3,4,5-triol)

3D SDF for NP0191864 ((2s,3r,4s,5r)-2-{[(2s,3s,4ar,4bs,7r,8as)-7-{[(2r,3r,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-ethenyl-2,4b,8,8-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-3h-phenanthren-3-yl]oxy}oxane-3,4,5-triol)

3D-SDF for NP0191864 ((2s,3r,4s,5r)-2-{[(2s,3s,4ar,4bs,7r,8as)-7-{[(2r,3r,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-ethenyl-2,4b,8,8-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-3h-phenanthren-3-yl]oxy}oxane-3,4,5-triol)

PDB for NP0191864 ((2s,3r,4s,5r)-2-{[(2s,3s,4ar,4bs,7r,8as)-7-{[(2r,3r,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-ethenyl-2,4b,8,8-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-3h-phenanthren-3-yl]oxy}oxane-3,4,5-triol)

3D PDB for NP0191864 ((2s,3r,4s,5r)-2-{[(2s,3s,4ar,4bs,7r,8as)-7-{[(2r,3r,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-ethenyl-2,4b,8,8-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-3h-phenanthren-3-yl]oxy}oxane-3,4,5-triol)

SMILES for NP0191864 ((2s,3r,4s,5r)-2-{[(2s,3s,4ar,4bs,7r,8as)-7-{[(2r,3r,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-ethenyl-2,4b,8,8-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-3h-phenanthren-3-yl]oxy}oxane-3,4,5-triol)

INCHI for NP0191864 ((2s,3r,4s,5r)-2-{[(2s,3s,4ar,4bs,7r,8as)-7-{[(2r,3r,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-ethenyl-2,4b,8,8-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-3h-phenanthren-3-yl]oxy}oxane-3,4,5-triol)

Structure for NP0191864 ((2s,3r,4s,5r)-2-{[(2s,3s,4ar,4bs,7r,8as)-7-{[(2r,3r,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-ethenyl-2,4b,8,8-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-3h-phenanthren-3-yl]oxy}oxane-3,4,5-triol)

3D Structure for NP0191864 ((2s,3r,4s,5r)-2-{[(2s,3s,4ar,4bs,7r,8as)-7-{[(2r,3r,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-ethenyl-2,4b,8,8-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-3h-phenanthren-3-yl]oxy}oxane-3,4,5-triol)