NP-MRD: Showing NP-Card for [(2r,3s,4s,5r,6r)-6-{[(1s,4ar,5s,7s,7as)-5-(acetyloxy)-7-methyl-1-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-7-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate (NP0181313)

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Record Information

Version

2.0

Created at

2022-09-03 19:48:45 UTC

Updated at

2022-09-03 19:48:45 UTC

NP-MRD ID

NP0181313

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,3s,4s,5r,6r)-6-{[(1s,4ar,5s,7s,7as)-5-(acetyloxy)-7-methyl-1-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-7-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate

Description

[(2R,3R,4S,5R,6S)-6-{[(1S,4aR,5S,7S,7aS)-5-(acetyloxy)-7-methyl-7-{[(2R,3R,4S,5S,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton. [(2r,3s,4s,5r,6r)-6-{[(1s,4ar,5s,7s,7as)-5-(acetyloxy)-7-methyl-1-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-7-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate is found in Rehmannia glutinosa. Based on a literature review very few articles have been published on [(2R,3R,4S,5R,6S)-6-{[(1S,4aR,5S,7S,7aS)-5-(acetyloxy)-7-methyl-7-{[(2R,3R,4S,5S,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032221482D          

 62 65  0  0  1  0            999 V2000
   -2.4336    2.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7192    1.9346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0047    2.3471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7192    1.1096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0047    0.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0047   -0.1279    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2902   -0.5404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2902   -1.3654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4243   -1.7779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4743   -2.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768    0.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752    0.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781    1.7103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.9246   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -3.5854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    6.2102   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.9246   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0668   -4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -5.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -6.0604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -5.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -5.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0047   -1.7779    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0047   -2.6029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2902   -3.0154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4243   -2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2902   -3.8404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7192   -1.3654    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4336   -1.7779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4336   -2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7192   -3.0154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1481   -3.0154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7192   -0.5404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4336   -0.1279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1481   -0.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1481   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8626   -0.1279    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
 10  9  1  1  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 24 23  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  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
 29 31  2  0  0  0  0
 26 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 32 37  1  0  0  0  0
 37 38  1  6  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
 37 42  1  0  0  0  0
 24 42  1  0  0  0  0
 42 43  1  1  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 44 46  2  0  0  0  0
 22 47  1  0  0  0  0
 47 18  1  6  0  0  0
 10 47  1  0  0  0  0
  8 48  1  0  0  0  0
 48 49  1  6  0  0  0
 49 50  1  0  0  0  0
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 48 53  1  0  0  0  0
 53 54  1  1  0  0  0
 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
 55 57  2  0  0  0  0
 53 58  1  0  0  0  0
  6 58  1  0  0  0  0
 58 59  1  1  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
 60 62  2  0  0  0  0
M  END

     RDKit          3D

114117  0  0  0  0  0  0  0  0999 V2000
   -6.3757    6.0729   -0.6737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0703    5.0060    0.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6076    5.0959    1.4595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2252    3.9412    0.0104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0144    2.9979    1.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.9870    1.0465    1.6903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5618   -0.2586    1.4561 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2875   -0.1907    0.9671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2942   -0.7323    1.7637 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1885   -0.0159    3.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5567   -2.2040    1.9353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2174   -2.7110    0.5554 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309032221482D          

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M  END
> <DATABASE_ID>
NP0181313

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@H]1O[C@@H](O[C@@H]2OC=C[C@H]3[C@H](C[C@](C)(O[C@H]4O[C@H](COC(C)=O)[C@H](OC(C)=O)[C@H](OC(C)=O)[C@H]4OC(C)=O)[C@@H]23)OC(C)=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C39H52O23/c1-16(40)50-14-27-30(53-19(4)43)32(55-21(6)45)34(57-23(8)47)37(59-27)61-36-29-25(11-12-49-36)26(52-18(3)42)13-39(29,10)62-38-35(58-24(9)48)33(56-22(7)46)31(54-20(5)44)28(60-38)15-51-17(2)41/h11-12,25-38H,13-15H2,1-10H3/t25-,26-,27+,28+,29+,30+,31-,32-,33-,34+,35+,36-,37-,38+,39-/m0/s1

> <INCHI_KEY>
PQOVWVGCRKNKBR-ZNUZHPMPSA-N

> <FORMULA>
C39H52O23

> <MOLECULAR_WEIGHT>
888.822

> <EXACT_MASS>
888.289937934

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
114

> <JCHEM_AVERAGE_POLARIZABILITY>
85.52883322501665

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6R)-6-{[(1S,4aR,5S,7S,7aS)-5-(acetyloxy)-7-methyl-1-{[(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-7-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate

> <JCHEM_LOGP>
-0.6570094870000018

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7826845707793235

> <JCHEM_POLAR_SURFACE_AREA>
282.84999999999997

> <JCHEM_REFRACTIVITY>
192.83760000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
24

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6R)-6-{[(1S,4aR,5S,7S,7aS)-5-(acetyloxy)-7-methyl-1-{[(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1H,4aH,5H,6H,7aH-cyclopenta[c]pyran-7-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.543   4.381   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.209   3.611   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.875   4.381   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -3.209   2.071   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.875   1.301   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.875  -0.239   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.542  -1.009   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.542  -2.549   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.792  -3.319   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.752  -3.956   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.650   1.408   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.143   1.728   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.887   0.583   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.333   3.192   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.258  -2.073   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.591  -4.383   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      10.259  -2.843   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      11.592  -2.073   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.592  -0.533   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      12.926  -2.843   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       8.925  -6.693   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      10.259  -7.463   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      11.592  -6.693   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.592  -5.153   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      12.926  -7.463   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       7.591  -7.463   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       7.591  -9.003   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       8.925  -9.773   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      10.259  -9.003   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       8.925 -11.313   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       6.258  -6.693   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       4.924  -7.463   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       4.924  -9.003   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       6.258  -9.773   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       3.590  -9.773   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -1.875  -3.319   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      -1.875  -4.859   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      -0.542  -5.629   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       0.792  -4.859   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      -0.542  -7.169   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      -3.209  -2.549   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      -4.543  -3.319   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      -4.543  -4.859   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      -3.209  -5.629   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      -5.876  -5.629   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0      -3.209  -1.009   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0      -4.543  -0.239   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0      -5.876  -1.009   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      -5.876  -2.549   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0      -7.210  -0.239   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   58                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   48                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12   47                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13   19   47                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   47                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   42                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   26   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   32   38   42                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39                                                            
CONECT   42   37   24   43                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44                                                            
CONECT   47   22   18   10                                                  
CONECT   48    8   49   53                                                  
CONECT   49   48   50                                                       
CONECT   50   49   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50                                                            
CONECT   53   48   54   58                                                  
CONECT   54   53   55                                                       
CONECT   55   54   56   57                                                  
CONECT   56   55                                                            
CONECT   57   55                                                            
CONECT   58   53    6   59                                                  
CONECT   59   58   60                                                       
CONECT   60   59   61   62                                                  
CONECT   61   60                                                            
CONECT   62   60                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  130    0
END

View in JSmol

Synonyms

Value	Source
[(2R,3R,4S,5R,6S)-6-{[(1S,4ar,5S,7S,7as)-5-(acetyloxy)-7-methyl-7-{[(2R,3R,4S,5S,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1H,4ah,5H,6H,7H,7ah-cyclopenta[c]pyran-1-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetic acid	Generator

Chemical Formula

C₃₉H₅₂O₂₃

Average Mass

888.8220 Da

Monoisotopic Mass

888.28994 Da

IUPAC Name

[(2R,3S,4S,5R,6R)-6-{[(1S,4aR,5S,7S,7aS)-5-(acetyloxy)-7-methyl-1-{[(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-7-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate

Traditional Name

[(2R,3S,4S,5R,6R)-6-{[(1S,4aR,5S,7S,7aS)-5-(acetyloxy)-7-methyl-1-{[(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1H,4aH,5H,6H,7aH-cyclopenta[c]pyran-7-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@H]1O[C@@H](O[C@@H]2OC=C[C@H]3[C@H](C[C@](C)(O[C@H]4O[C@H](COC(C)=O)[C@H](OC(C)=O)[C@H](OC(C)=O)[C@H]4OC(C)=O)[C@@H]23)OC(C)=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O

InChI Identifier

InChI=1S/C39H52O23/c1-16(40)50-14-27-30(53-19(4)43)32(55-21(6)45)34(57-23(8)47)37(59-27)61-36-29-25(11-12-49-36)26(52-18(3)42)13-39(29,10)62-38-35(58-24(9)48)33(56-22(7)46)31(54-20(5)44)28(60-38)15-51-17(2)41/h11-12,25-38H,13-15H2,1-10H3/t25-,26-,27+,28+,29+,30+,31-,32-,33-,34+,35+,36-,37-,38+,39-/m0/s1

InChI Key

PQOVWVGCRKNKBR-ZNUZHPMPSA-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
Rehmannia glutinosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Iridoid O-glycosides

Alternative Parents

Substituents

Iridoid o-glycoside
Glycosyl compound
Iridoid-skeleton
O-glycosyl compound
Bicyclic monoterpenoid
Monoterpenoid
Monosaccharide
Oxane
Carboxylic acid ester
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organooxygen compound
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	-0.66	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	282.85 Å²	ChemAxon
Rotatable Bond Count	24	ChemAxon
Refractivity	192.84 m³·mol⁻¹	ChemAxon
Polarizability	85.53 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

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

162878751

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(2r,3s,4s,5r,6r)-6-{[(1s,4ar,5s,7s,7as)-5-(acetyloxy)-7-methyl-1-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-7-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate (NP0181313)

MOL for NP0181313 ([(2r,3s,4s,5r,6r)-6-{[(1s,4ar,5s,7s,7as)-5-(acetyloxy)-7-methyl-1-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-7-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

3D MOL for NP0181313 ([(2r,3s,4s,5r,6r)-6-{[(1s,4ar,5s,7s,7as)-5-(acetyloxy)-7-methyl-1-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-7-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

3D SDF for NP0181313 ([(2r,3s,4s,5r,6r)-6-{[(1s,4ar,5s,7s,7as)-5-(acetyloxy)-7-methyl-1-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-7-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

3D-SDF for NP0181313 ([(2r,3s,4s,5r,6r)-6-{[(1s,4ar,5s,7s,7as)-5-(acetyloxy)-7-methyl-1-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-7-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

PDB for NP0181313 ([(2r,3s,4s,5r,6r)-6-{[(1s,4ar,5s,7s,7as)-5-(acetyloxy)-7-methyl-1-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-7-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

3D PDB for NP0181313 ([(2r,3s,4s,5r,6r)-6-{[(1s,4ar,5s,7s,7as)-5-(acetyloxy)-7-methyl-1-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-7-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

SMILES for NP0181313 ([(2r,3s,4s,5r,6r)-6-{[(1s,4ar,5s,7s,7as)-5-(acetyloxy)-7-methyl-1-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-7-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

INCHI for NP0181313 ([(2r,3s,4s,5r,6r)-6-{[(1s,4ar,5s,7s,7as)-5-(acetyloxy)-7-methyl-1-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-7-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

Structure for NP0181313 ([(2r,3s,4s,5r,6r)-6-{[(1s,4ar,5s,7s,7as)-5-(acetyloxy)-7-methyl-1-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-7-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

3D Structure for NP0181313 ([(2r,3s,4s,5r,6r)-6-{[(1s,4ar,5s,7s,7as)-5-(acetyloxy)-7-methyl-1-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-7-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)