NP-MRD: Showing NP-Card for (3s,3ar,5's,6as,7r,8r,10r,10ar)-5'-(furan-3-yl)-8-methyl-2'-oxo-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydrospiro[naphtho[1,8a-c]furan-7,3'-oxolan]-10-yl acetate (NP0204322)

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Record Information

Version

2.0

Created at

2022-09-04 23:58:16 UTC

Updated at

2022-09-04 23:58:16 UTC

NP-MRD ID

NP0204322

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,3ar,5's,6as,7r,8r,10r,10ar)-5'-(furan-3-yl)-8-methyl-2'-oxo-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydrospiro[naphtho[1,8a-c]furan-7,3'-oxolan]-10-yl acetate

Description

(3S,5'S,6aS,7R,8R,10R,10aR,10bR)-5'-(furan-3-yl)-8-methyl-2'-oxo-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydrospiro[naphtho[4,4a-c]furan-7,3'-oxolane]-10-yl acetate belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. (3s,3ar,5's,6as,7r,8r,10r,10ar)-5'-(furan-3-yl)-8-methyl-2'-oxo-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydrospiro[naphtho[1,8a-c]furan-7,3'-oxolan]-10-yl acetate is found in Teucrium lamiifolium. Based on a literature review very few articles have been published on (3S,5'S,6aS,7R,8R,10R,10aR,10bR)-5'-(furan-3-yl)-8-methyl-2'-oxo-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydrospiro[naphtho[4,4a-c]furan-7,3'-oxolane]-10-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052201582D          

 40 45  0  0  1  0            999 V2000
    2.1142    2.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5145    2.1245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7240    2.3606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7052    1.3218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6123    1.0823    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0954    1.6522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8859    1.4160    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4857    1.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0767    0.6134    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7323    1.1141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4112    0.6452    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1895    0.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4256    1.7093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2504    1.7290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5240    0.9507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8683    0.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1750   -0.1453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3503   -0.1649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1141   -0.9554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4769    0.0469    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    3.0679   -1.3223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2774   -1.0861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0867   -0.2835    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3626    0.1118    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6171   -0.2416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0617    0.2273    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8071   -0.1262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4860    0.3427    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -2.2981   -0.8331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4193    1.1650    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0982    1.6338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6739    1.5184    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6073    2.3407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0049    1.0496    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7504    1.4030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5148    0.9227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3330    1.0285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6864    0.2830    0.0000 C   0  0  2  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
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 16  2  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  2  0  0  0  0
  9 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 23  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 27 26  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 29 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
 27 36  1  0  0  0  0
 36 37  1  1  0  0  0
 25 38  1  0  0  0  0
 38 39  1  0  0  0  0
 40 39  1  1  0  0  0
 20 40  1  0  0  0  0
  5 40  1  0  0  0  0
 24 40  1  0  0  0  0
M  END

     RDKit          3D

 78 83  0  0  0  0  0  0  0  0999 V2000
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    5.0915   -0.5853   -0.4320 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9596    0.3331    0.3007 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6518    0.7800    1.5742 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7716    2.2659    1.4544 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1919    2.7397    1.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3005    2.1330    2.0324 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3541    3.0165    1.8507 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.4580   -1.1625    1.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.1447    2.0895    0.8729 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8323    1.2336   -1.2430 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.8470   -0.4773   -0.7118 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309052201582D          

 40 45  0  0  1  0            999 V2000
    2.1142    2.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5145    2.1245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7240    2.3606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7052    1.3218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6123    1.0823    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0954    1.6522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8859    1.4160    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4857    1.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0767    0.6134    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7323    1.1141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4112    0.6452    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1895    0.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.5240    0.9507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1750   -0.1453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1141   -0.9554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4769    0.0469    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6677   -0.7558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0679   -1.3223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2774   -1.0861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0867   -0.2835    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3626    0.1118    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6171   -0.2416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0617    0.2273    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8071   -0.1262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4860    0.3427    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2314   -0.0108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2981   -0.8331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4193    1.1650    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0982    1.6338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6739    1.5184    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6073    2.3407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0049    1.0496    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7504    1.4030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5148    0.9227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3330    1.0285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6864    0.2830    0.0000 C   0  0  2  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
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 16  2  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  2  0  0  0  0
  9 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 23  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 27 26  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 29 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
 27 36  1  0  0  0  0
 36 37  1  1  0  0  0
 25 38  1  0  0  0  0
 38 39  1  0  0  0  0
 40 39  1  1  0  0  0
 20 40  1  0  0  0  0
  5 40  1  0  0  0  0
 24 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0204322

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@@H](OC(C)=O)[C@@]23CO[C@@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H]2CCC[C@@H]3[C@@]11C[C@H](OC1=O)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H38O12/c1-13-8-20(37-14(2)30)28-12-36-24(40-25-23(33)22(32)21(31)18(10-29)38-25)16(28)4-3-5-19(28)27(13)9-17(39-26(27)34)15-6-7-35-11-15/h6-7,11,13,16-25,29,31-33H,3-5,8-10,12H2,1-2H3/t13-,16+,17+,18-,19-,20-,21-,22+,23-,24+,25+,27-,28+/m1/s1

> <INCHI_KEY>
NOGJIXRQGTUADR-PMKMREHWSA-N

> <FORMULA>
C28H38O12

> <MOLECULAR_WEIGHT>
566.6

> <EXACT_MASS>
566.236326664

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
57.68562088467951

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,5'S,6aS,7R,8R,10R,10aR,10bR)-5'-(furan-3-yl)-8-methyl-2'-oxo-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydrospiro[naphtho[1,8a-c]furan-7,3'-oxolane]-10-yl acetate

> <JCHEM_LOGP>
0.39966417066666515

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.198731911428158

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.20704972648104

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8509816753776707

> <JCHEM_POLAR_SURFACE_AREA>
174.35

> <JCHEM_REFRACTIVITY>
132.53160000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3S,5'S,6aS,7R,8R,10R,10aR,10bR)-5'-(furan-3-yl)-8-methyl-2'-oxo-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydrospiro[naphtho[1,8a-c]furan-7,3'-oxolane]-10-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       3.947   5.023   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.827   3.966   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.351   4.406   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.183   2.467   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.876   2.020   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.778   3.084   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.254   2.643   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.373   3.701   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.610   1.145   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.834   2.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.101   1.204   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.554   1.715   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.994   3.191   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.534   3.227   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      14.045   1.775   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      12.821   0.840   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.660  -0.271   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.120  -0.308   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.680  -1.783   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.490   0.087   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.846  -1.411   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.727  -2.468   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.251  -2.027   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.895  -0.529   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.543   0.209   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.152  -0.451   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.115   0.424   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.507  -0.236   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -2.774   0.640   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.165  -0.020   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -4.290  -1.555   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -2.649   2.175   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -3.917   3.050   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -1.258   2.834   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -1.134   4.369   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       0.009   1.959   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       1.401   2.619   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       2.828   1.722   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       4.355   1.920   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       5.015   0.528   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   40                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   18   20                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12                                                       
CONECT   17   11   18                                                       
CONECT   18   17    9   19                                                  
CONECT   19   18                                                            
CONECT   20    9   21   40                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   40                                                  
CONECT   25   24   26   38                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   36                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   29   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   27   37                                                  
CONECT   37   36                                                            
CONECT   38   25   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   20    5   24                                             
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Value	Source
(3S,5's,6AS,7R,8R,10R,10ar,10BR)-5'-(furan-3-yl)-8-methyl-2'-oxo-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydrospiro[naphtho[4,4a-c]furan-7,3'-oxolane]-10-yl acetic acid	Generator

Chemical Formula

C₂₈H₃₈O₁₂

Average Mass

566.6000 Da

Monoisotopic Mass

566.23633 Da

IUPAC Name

(3S,5'S,6aS,7R,8R,10R,10aR,10bR)-5'-(furan-3-yl)-8-methyl-2'-oxo-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydrospiro[naphtho[1,8a-c]furan-7,3'-oxolane]-10-yl acetate

Traditional Name

(3S,5'S,6aS,7R,8R,10R,10aR,10bR)-5'-(furan-3-yl)-8-methyl-2'-oxo-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydrospiro[naphtho[1,8a-c]furan-7,3'-oxolane]-10-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@@H](OC(C)=O)[C@@]23CO[C@@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H]2CCC[C@@H]3[C@@]11C[C@H](OC1=O)C1=COC=C1

InChI Identifier

InChI=1S/C28H38O12/c1-13-8-20(37-14(2)30)28-12-36-24(40-25-23(33)22(32)21(31)18(10-29)38-25)16(28)4-3-5-19(28)27(13)9-17(39-26(27)34)15-6-7-35-11-15/h6-7,11,13,16-25,29,31-33H,3-5,8-10,12H2,1-2H3/t13-,16+,17+,18-,19-,20-,21-,22+,23-,24+,25+,27-,28+/m1/s1

InChI Key

NOGJIXRQGTUADR-PMKMREHWSA-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
Teucrium lamiifolium	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
Diterpene lactone
Diterpenoid
Clerodane diterpenoid
Naphthofuran
Glycosyl compound
O-glycosyl compound
Dicarboxylic acid or derivatives
Gamma butyrolactone
Monosaccharide
Oxane
Tetrahydrofuran
Heteroaromatic compound
Furan
Secondary alcohol
Carboxylic acid ester
Lactone
Polyol
Carboxylic acid derivative
Acetal
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Carbonyl group
Primary alcohol
Organic oxide
Hydrocarbon derivative
Alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	0.4	ChemAxon
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	174.35 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	132.53 m³·mol⁻¹	ChemAxon
Polarizability	57.69 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	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

162868265

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s,3ar,5's,6as,7r,8r,10r,10ar)-5'-(furan-3-yl)-8-methyl-2'-oxo-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydrospiro[naphtho[1,8a-c]furan-7,3'-oxolan]-10-yl acetate (NP0204322)

MOL for NP0204322 ((3s,3ar,5's,6as,7r,8r,10r,10ar)-5'-(furan-3-yl)-8-methyl-2'-oxo-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydrospiro[naphtho[1,8a-c]furan-7,3'-oxolan]-10-yl acetate)

3D MOL for NP0204322 ((3s,3ar,5's,6as,7r,8r,10r,10ar)-5'-(furan-3-yl)-8-methyl-2'-oxo-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydrospiro[naphtho[1,8a-c]furan-7,3'-oxolan]-10-yl acetate)

3D SDF for NP0204322 ((3s,3ar,5's,6as,7r,8r,10r,10ar)-5'-(furan-3-yl)-8-methyl-2'-oxo-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydrospiro[naphtho[1,8a-c]furan-7,3'-oxolan]-10-yl acetate)

3D-SDF for NP0204322 ((3s,3ar,5's,6as,7r,8r,10r,10ar)-5'-(furan-3-yl)-8-methyl-2'-oxo-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydrospiro[naphtho[1,8a-c]furan-7,3'-oxolan]-10-yl acetate)

PDB for NP0204322 ((3s,3ar,5's,6as,7r,8r,10r,10ar)-5'-(furan-3-yl)-8-methyl-2'-oxo-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydrospiro[naphtho[1,8a-c]furan-7,3'-oxolan]-10-yl acetate)

3D PDB for NP0204322 ((3s,3ar,5's,6as,7r,8r,10r,10ar)-5'-(furan-3-yl)-8-methyl-2'-oxo-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydrospiro[naphtho[1,8a-c]furan-7,3'-oxolan]-10-yl acetate)

SMILES for NP0204322 ((3s,3ar,5's,6as,7r,8r,10r,10ar)-5'-(furan-3-yl)-8-methyl-2'-oxo-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydrospiro[naphtho[1,8a-c]furan-7,3'-oxolan]-10-yl acetate)

INCHI for NP0204322 ((3s,3ar,5's,6as,7r,8r,10r,10ar)-5'-(furan-3-yl)-8-methyl-2'-oxo-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydrospiro[naphtho[1,8a-c]furan-7,3'-oxolan]-10-yl acetate)

Structure for NP0204322 ((3s,3ar,5's,6as,7r,8r,10r,10ar)-5'-(furan-3-yl)-8-methyl-2'-oxo-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydrospiro[naphtho[1,8a-c]furan-7,3'-oxolan]-10-yl acetate)

3D Structure for NP0204322 ((3s,3ar,5's,6as,7r,8r,10r,10ar)-5'-(furan-3-yl)-8-methyl-2'-oxo-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydrospiro[naphtho[1,8a-c]furan-7,3'-oxolan]-10-yl acetate)