NP-MRD: Showing NP-Card for (4ar,6s,7r,7as)-7-methyl-3-oxo-hexahydro-1h-cyclopenta[c]pyran-6-yl (4s,5r,6s)-4-[2-(acetyloxy)ethyl]-5-ethenyl-6-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate (NP0222133)

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Record Information

Version

2.0

Created at

2022-09-05 23:53:25 UTC

Updated at

2022-09-05 23:53:25 UTC

NP-MRD ID

NP0222133

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4ar,6s,7r,7as)-7-methyl-3-oxo-hexahydro-1h-cyclopenta[c]pyran-6-yl (4s,5r,6s)-4-[2-(acetyloxy)ethyl]-5-ethenyl-6-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate

Description

(4AR,6S,7R,7aS)-7-methyl-3-oxo-octahydrocyclopenta[c]pyran-6-yl (2S,3R,4S)-4-[2-(acetyloxy)ethyl]-3-ethenyl-2-{[(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. (4ar,6s,7r,7as)-7-methyl-3-oxo-hexahydro-1h-cyclopenta[c]pyran-6-yl (4s,5r,6s)-4-[2-(acetyloxy)ethyl]-5-ethenyl-6-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate is found in Abelia grandiflora. Based on a literature review very few articles have been published on (4aR,6S,7R,7aS)-7-methyl-3-oxo-octahydrocyclopenta[c]pyran-6-yl (2S,3R,4S)-4-[2-(acetyloxy)ethyl]-3-ethenyl-2-{[(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062201532D          

 52 55  0  0  1  0            999 V2000
   -3.8837    1.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0587    1.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462    0.7310    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0587    0.0165    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8837    0.0165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2962   -0.6979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8837   -1.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2962   -2.1269    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8837   -2.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0587   -2.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462   -2.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212   -2.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0587   -1.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1212   -2.1269    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5337   -2.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1212   -3.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2962   -3.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5337   -4.2703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5337   -1.4124    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3587   -1.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7712   -2.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5962   -2.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3587   -2.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1212   -0.6979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5337    0.0165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3587    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7712    0.7310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    0.7310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   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
    4.0668    0.1271    0.0000 O   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  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
    1.1387   -1.3654    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    0.7310    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4087    1.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    2.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462    2.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0587    2.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8837    2.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462    3.5889    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  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 19 24  1  0  0  0  0
  6 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
  4 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 35 34  1  1  0  0  0
 35 36  1  0  0  0  0
 37 36  1  6  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 43 42  1  6  0  0  0
 37 43  1  0  0  0  0
 43 44  1  0  0  0  0
 35 44  1  0  0  0  0
 44 45  1  1  0  0  0
 31 46  1  0  0  0  0
  3 46  1  0  0  0  0
 46 47  1  6  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 50 52  2  0  0  0  0
M  END


  Mrv1652309062201532D          

 52 55  0  0  1  0            999 V2000
   -3.8837    1.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0587    1.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462    0.7310    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0587    0.0165    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8837    0.0165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2962   -0.6979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8837   -1.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2962   -2.1269    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8837   -2.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0587   -2.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462   -2.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212   -2.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0587   -1.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1212   -2.1269    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5337   -2.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1212   -3.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2962   -3.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5337   -4.2703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5337   -1.4124    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3587   -1.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7712   -2.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5962   -2.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3587   -2.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1212   -0.6979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5337    0.0165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3587    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7712    0.7310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    0.7310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   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
    4.0668    0.1271    0.0000 O   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  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
    1.1387   -1.3654    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    0.7310    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4087    1.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    2.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462    2.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0587    2.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8837    2.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462    3.5889    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  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 19 24  1  0  0  0  0
  6 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
  4 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 35 34  1  1  0  0  0
 35 36  1  0  0  0  0
 37 36  1  6  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 43 42  1  6  0  0  0
 37 43  1  0  0  0  0
 43 44  1  0  0  0  0
 35 44  1  0  0  0  0
 44 45  1  1  0  0  0
 31 46  1  0  0  0  0
  3 46  1  0  0  0  0
 46 47  1  6  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 50 52  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0222133

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@H](C[C@@H]2CC(=O)OC[C@H]12)OC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]2OC(C)=O)[C@H](C=C)[C@@H]1CCOC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C35H46O17/c1-8-23-24(9-10-43-17(3)36)26(33(42)50-27-11-22-12-29(41)45-13-25(22)16(27)2)14-46-34(23)52-35-32(49-21(7)40)31(48-20(6)39)30(47-19(5)38)28(51-35)15-44-18(4)37/h8,14,16,22-25,27-28,30-32,34-35H,1,9-13,15H2,2-7H3/t16-,22-,23-,24+,25-,27+,28-,30-,31+,32-,34+,35+/m1/s1

> <INCHI_KEY>
BDGNDSGAEIXPIR-WOFSCAGESA-N

> <FORMULA>
C35H46O17

> <MOLECULAR_WEIGHT>
738.736

> <EXACT_MASS>
738.273500021

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
98

> <JCHEM_AVERAGE_POLARIZABILITY>
74.15768249306196

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4aR,6S,7R,7aS)-7-methyl-3-oxo-octahydrocyclopenta[c]pyran-6-yl (2S,3R,4S)-4-[2-(acetyloxy)ethyl]-3-ethenyl-2-{[(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate

> <JCHEM_LOGP>
1.2816412763333347

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.088662394593445

> <JCHEM_POLAR_SURFACE_AREA>
211.78999999999996

> <JCHEM_REFRACTIVITY>
170.0747

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -7.250   2.698   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.710   2.698   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.940   1.365   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.710   0.031   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -7.250   0.031   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -8.020  -1.303   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -7.250  -2.637   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -8.020  -3.970   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -7.250  -5.304   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -5.710  -5.304   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -4.940  -3.970   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.400  -3.970   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -5.710  -2.637   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -9.560  -3.970   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0     -10.330  -5.304   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -9.560  -6.638   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -8.020  -6.638   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0     -10.330  -7.971   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0     -10.330  -2.637   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0     -11.870  -2.637   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0     -12.640  -3.970   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -14.180  -3.970   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0     -11.870  -5.304   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -9.560  -1.303   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0     -10.330   0.031   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0     -11.870   0.031   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -12.640  -1.303   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0     -12.640   1.365   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -4.940  -1.303   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -3.400  -1.303   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.630   0.031   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.090   0.031   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -0.320   1.365   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -0.320  -1.303   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       7.591   0.237   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       6.258  -2.073   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -3.400   1.365   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -2.630   2.698   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -3.400   4.032   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      -4.940   4.032   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      -5.710   5.366   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      -7.250   5.366   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      -4.940   6.699   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   46                                                  
CONECT    4    3    5   29                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   24                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    8   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   14   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   19    6   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29    4   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   46                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36   44                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   43                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   37   44                                                  
CONECT   44   43   35   45                                                  
CONECT   45   44                                                            
CONECT   46   31    3   47                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  110    0
END

View in JSmol

Synonyms

Value	Source
(4AR,6S,7R,7as)-7-methyl-3-oxo-octahydrocyclopenta[c]pyran-6-yl (2S,3R,4S)-4-[2-(acetyloxy)ethyl]-3-ethenyl-2-{[(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylic acid	Generator

Chemical Formula

C₃₅H₄₆O₁₇

Average Mass

738.7360 Da

Monoisotopic Mass

738.27350 Da

IUPAC Name

(4aR,6S,7R,7aS)-7-methyl-3-oxo-octahydrocyclopenta[c]pyran-6-yl (2S,3R,4S)-4-[2-(acetyloxy)ethyl]-3-ethenyl-2-{[(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate

Traditional Name

(4aR,6S,7R,7aS)-7-methyl-3-oxo-hexahydro-1H-cyclopenta[c]pyran-6-yl (4S,5R,6S)-4-[2-(acetyloxy)ethyl]-5-ethenyl-6-{[(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-5,6-dihydro-4H-pyran-3-carboxylate

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@H](C[C@@H]2CC(=O)OC[C@H]12)OC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]2OC(C)=O)[C@H](C=C)[C@@H]1CCOC(C)=O

InChI Identifier

InChI=1S/C35H46O17/c1-8-23-24(9-10-43-17(3)36)26(33(42)50-27-11-22-12-29(41)45-13-25(22)16(27)2)14-46-34(23)52-35-32(49-21(7)40)31(48-20(6)39)30(47-19(5)38)28(51-35)15-44-18(4)37/h8,14,16,22-25,27-28,30-32,34-35H,1,9-13,15H2,2-7H3/t16-,22-,23-,24+,25-,27+,28-,30-,31+,32-,34+,35+/m1/s1

InChI Key

BDGNDSGAEIXPIR-WOFSCAGESA-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
Abelia grandiflora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Terpene lactone
Glycosyl compound
Iridoid-skeleton
Secoiridoid-skeleton
O-glycosyl compound
Bicyclic monoterpenoid
Monoterpenoid
Delta valerolactone
Sugar acid
Delta_valerolactone
Oxane
Monosaccharide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Vinylogous ester
Carboxylic acid ester
Lactone
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
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	1.28	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	211.79 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	170.07 m³·mol⁻¹	ChemAxon
Polarizability	74.16 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

162936170

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4ar,6s,7r,7as)-7-methyl-3-oxo-hexahydro-1h-cyclopenta[c]pyran-6-yl (4s,5r,6s)-4-[2-(acetyloxy)ethyl]-5-ethenyl-6-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate (NP0222133)

MOL for NP0222133 ((4ar,6s,7r,7as)-7-methyl-3-oxo-hexahydro-1h-cyclopenta[c]pyran-6-yl (4s,5r,6s)-4-[2-(acetyloxy)ethyl]-5-ethenyl-6-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

3D MOL for NP0222133 ((4ar,6s,7r,7as)-7-methyl-3-oxo-hexahydro-1h-cyclopenta[c]pyran-6-yl (4s,5r,6s)-4-[2-(acetyloxy)ethyl]-5-ethenyl-6-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

3D SDF for NP0222133 ((4ar,6s,7r,7as)-7-methyl-3-oxo-hexahydro-1h-cyclopenta[c]pyran-6-yl (4s,5r,6s)-4-[2-(acetyloxy)ethyl]-5-ethenyl-6-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

3D-SDF for NP0222133 ((4ar,6s,7r,7as)-7-methyl-3-oxo-hexahydro-1h-cyclopenta[c]pyran-6-yl (4s,5r,6s)-4-[2-(acetyloxy)ethyl]-5-ethenyl-6-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

PDB for NP0222133 ((4ar,6s,7r,7as)-7-methyl-3-oxo-hexahydro-1h-cyclopenta[c]pyran-6-yl (4s,5r,6s)-4-[2-(acetyloxy)ethyl]-5-ethenyl-6-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

3D PDB for NP0222133 ((4ar,6s,7r,7as)-7-methyl-3-oxo-hexahydro-1h-cyclopenta[c]pyran-6-yl (4s,5r,6s)-4-[2-(acetyloxy)ethyl]-5-ethenyl-6-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

SMILES for NP0222133 ((4ar,6s,7r,7as)-7-methyl-3-oxo-hexahydro-1h-cyclopenta[c]pyran-6-yl (4s,5r,6s)-4-[2-(acetyloxy)ethyl]-5-ethenyl-6-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

INCHI for NP0222133 ((4ar,6s,7r,7as)-7-methyl-3-oxo-hexahydro-1h-cyclopenta[c]pyran-6-yl (4s,5r,6s)-4-[2-(acetyloxy)ethyl]-5-ethenyl-6-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

Structure for NP0222133 ((4ar,6s,7r,7as)-7-methyl-3-oxo-hexahydro-1h-cyclopenta[c]pyran-6-yl (4s,5r,6s)-4-[2-(acetyloxy)ethyl]-5-ethenyl-6-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

3D Structure for NP0222133 ((4ar,6s,7r,7as)-7-methyl-3-oxo-hexahydro-1h-cyclopenta[c]pyran-6-yl (4s,5r,6s)-4-[2-(acetyloxy)ethyl]-5-ethenyl-6-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)