NP-MRD: Showing NP-Card for methyl (1r,2s,7r,8s,9s)-8-[(2r)-2-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]-2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0²,⁷]dodec-3-ene-3-carboxylate (NP0220277)

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Record Information

Version

2.0

Created at

2022-09-05 21:32:34 UTC

Updated at

2022-09-05 21:32:35 UTC

NP-MRD ID

NP0220277

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1r,2s,7r,8s,9s)-8-[(2r)-2-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]-2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0²,⁷]dodec-3-ene-3-carboxylate

Description

Methyl (1R,2S,7R,8S,9S)-8-[(2R)-2-[(2R)-2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl]-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0²,⁷]Dodec-3-ene-3-carboxylate belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. methyl (1r,2s,7r,8s,9s)-8-[(2r)-2-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]-2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0²,⁷]dodec-3-ene-3-carboxylate is found in Tinospora crispa. Based on a literature review very few articles have been published on methyl (1R,2S,7R,8S,9S)-8-[(2R)-2-[(2R)-2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl]-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0²,⁷]Dodec-3-ene-3-carboxylate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052223322D          

 40 44  0  0  1  0            999 V2000
   -1.1091    3.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1992    2.5407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5341    2.0526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2211    2.3846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6243    1.2326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3796    0.9006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4697    0.0806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8046   -0.4076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0494   -0.0756    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5356   -0.6574    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1618   -1.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8101   -1.4354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2737   -2.0621    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5483   -2.8401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3593   -2.9913    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8957   -2.3645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7068   -2.5157    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2432   -1.8890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9686   -1.1110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9813   -3.2937    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7924   -3.4449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4449   -3.9205    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7195   -4.6984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6339   -3.7693    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0974   -4.3961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5373   -1.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8917   -1.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7098   -1.2728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2770   -0.6737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8610   -2.0838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1364   -2.4782    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0295   -3.2963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3551   -0.5628    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2652    0.3883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7382    1.1852    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5176    0.9149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7922    0.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6122    0.0467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0408    0.7444    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0694    1.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  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  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  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  6  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 15 24  1  0  0  0  0
 24 25  1  1  0  0  0
 13 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 26 31  1  0  0  0  0
 31 32  1  6  0  0  0
 10 33  1  0  0  0  0
 33 34  1  1  0  0  0
 35 34  1  1  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 33 37  1  0  0  0  0
 37 38  2  0  0  0  0
 35 39  1  0  0  0  0
  5 39  1  0  0  0  0
  9 39  1  0  0  0  0
 39 40  1  6  0  0  0
M  END


  Mrv1652309052223322D          

 40 44  0  0  1  0            999 V2000
   -1.1091    3.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1992    2.5407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5341    2.0526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2211    2.3846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6243    1.2326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3796    0.9006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4697    0.0806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8046   -0.4076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0494   -0.0756    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5356   -0.6574    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1618   -1.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8101   -1.4354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2737   -2.0621    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5483   -2.8401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3593   -2.9913    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8957   -2.3645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7068   -2.5157    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2432   -1.8890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9686   -1.1110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9813   -3.2937    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7924   -3.4449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4449   -3.9205    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7195   -4.6984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6339   -3.7693    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0974   -4.3961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5373   -1.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8917   -1.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7098   -1.2728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2770   -0.6737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8610   -2.0838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1364   -2.4782    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0295   -3.2963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3551   -0.5628    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2652    0.3883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7382    1.1852    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5176    0.9149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7922    0.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6122    0.0467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0408    0.7444    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0694    1.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  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  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  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  6  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 15 24  1  0  0  0  0
 24 25  1  1  0  0  0
 13 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 26 31  1  0  0  0  0
 31 32  1  6  0  0  0
 10 33  1  0  0  0  0
 33 34  1  1  0  0  0
 35 34  1  1  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 33 37  1  0  0  0  0
 37 38  2  0  0  0  0
 35 39  1  0  0  0  0
  5 39  1  0  0  0  0
  9 39  1  0  0  0  0
 39 40  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0220277

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CCC[C@@H]2[C@](C)(C[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C3=CC(=O)O[C@H]3O)[C@@H]3C[C@@H](OC3=O)[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C27H36O13/c1-26(13-8-17(39-24(13)35)27(2)12(23(34)36-3)5-4-6-16(26)27)9-14(11-7-18(29)40-22(11)33)37-25-21(32)20(31)19(30)15(10-28)38-25/h5,7,13-17,19-22,25,28,30-33H,4,6,8-10H2,1-3H3/t13-,14-,15-,16-,17-,19-,20+,21-,22-,25-,26-,27-/m1/s1

> <INCHI_KEY>
OXXLAQAXFVVCAB-UNPYXNEZSA-N

> <FORMULA>
C27H36O13

> <MOLECULAR_WEIGHT>
568.572

> <EXACT_MASS>
568.215591219

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
54.62699033206175

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1R,2S,7R,8S,9S)-8-[(2R)-2-[(2R)-2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl]-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0^{2,7}]dodec-3-ene-3-carboxylate

> <JCHEM_LOGP>
-0.38688057600000203

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.607567348564867

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.491692281048369

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810836844735826

> <JCHEM_POLAR_SURFACE_AREA>
198.51

> <JCHEM_REFRACTIVITY>
132.43579999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,2S,7R,8S,9S)-8-[(2R)-2-[(2R)-2-hydroxy-5-oxo-2H-furan-3-yl]-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0^{2,7}]dodec-3-ene-3-carboxylate

> <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      -2.070   6.273   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.239   4.743   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.997   3.832   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.413   4.451   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.165   2.301   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.575   1.681   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.744   0.150   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.502  -0.761   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.092  -0.141   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.000  -1.227   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.302  -2.050   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.512  -2.679   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.511  -3.849   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.023  -5.302   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.537  -5.584   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.539  -4.414   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.053  -4.696   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.054  -3.526   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.541  -2.074   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.565  -6.148   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.079  -6.430   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.564  -7.318   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.076  -8.770   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.050  -7.036   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.048  -8.206   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.003  -3.567   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.665  -2.176   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.192  -2.376   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -4.250  -1.258   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -3.474  -3.890   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -2.121  -4.626   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.922  -6.153   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.530  -1.051   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.362   0.725   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.378   2.212   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       2.833   1.708   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       3.345   0.256   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       4.876   0.087   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       0.076   1.390   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       0.130   2.929   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   39                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   39                                                  
CONECT   10    9   11   12   33                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   26                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   24                                                  
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   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   15   25                                                  
CONECT   25   24                                                            
CONECT   26   13   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   26   32                                                  
CONECT   32   31                                                            
CONECT   33   10   34   37                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   39                                                  
CONECT   36   35   37                                                       
CONECT   37   36   33   38                                                  
CONECT   38   37                                                            
CONECT   39   35    5    9   40                                             
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1R,2S,7R,8S,9S)-8-[(2R)-2-[(2R)-2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl]-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0,]dodec-3-ene-3-carboxylic acid	Generator

Chemical Formula

C₂₇H₃₆O₁₃

Average Mass

568.5720 Da

Monoisotopic Mass

568.21559 Da

IUPAC Name

methyl (1R,2S,7R,8S,9S)-8-[(2R)-2-[(2R)-2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl]-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0^{2,7}]dodec-3-ene-3-carboxylate

Traditional Name

methyl (1R,2S,7R,8S,9S)-8-[(2R)-2-[(2R)-2-hydroxy-5-oxo-2H-furan-3-yl]-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0^{2,7}]dodec-3-ene-3-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CCC[C@@H]2[C@](C)(C[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C3=CC(=O)O[C@H]3O)[C@@H]3C[C@@H](OC3=O)[C@]12C

InChI Identifier

InChI=1S/C27H36O13/c1-26(13-8-17(39-24(13)35)27(2)12(23(34)36-3)5-4-6-16(26)27)9-14(11-7-18(29)40-22(11)33)37-25-21(32)20(31)19(30)15(10-28)38-25/h5,7,13-17,19-22,25,28,30-33H,4,6,8-10H2,1-3H3/t13-,14-,15-,16-,17-,19-,20+,21-,22-,25-,26-,27-/m1/s1

InChI Key

OXXLAQAXFVVCAB-UNPYXNEZSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Tinospora crispa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Tricarboxylic acid or derivatives
Caprolactone
Oxepane
2-furanone
Oxane
Monosaccharide
Gamma butyrolactone
Enoate ester
Methyl ester
Alpha,beta-unsaturated carboxylic ester
Tetrahydrofuran
Dihydrofuran
Secondary alcohol
Carboxylic acid ester
Lactone
Hemiacetal
Acetal
Polyol
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Carbonyl group
Alcohol
Organooxygen compound
Organic oxygen compound
Organic oxide
Primary alcohol
Hydrocarbon derivative
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	-0.39	ChemAxon
pKa (Strongest Acidic)	5.49	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	198.51 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	132.44 m³·mol⁻¹	ChemAxon
Polarizability	54.63 Å³	ChemAxon
Number of Rings	5	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

162973761

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1r,2s,7r,8s,9s)-8-[(2r)-2-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]-2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0²,⁷]dodec-3-ene-3-carboxylate (NP0220277)

MOL for NP0220277 (methyl (1r,2s,7r,8s,9s)-8-[(2r)-2-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]-2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0²,⁷]dodec-3-ene-3-carboxylate)

3D MOL for NP0220277 (methyl (1r,2s,7r,8s,9s)-8-[(2r)-2-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]-2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0²,⁷]dodec-3-ene-3-carboxylate)

3D SDF for NP0220277 (methyl (1r,2s,7r,8s,9s)-8-[(2r)-2-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]-2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0²,⁷]dodec-3-ene-3-carboxylate)

3D-SDF for NP0220277 (methyl (1r,2s,7r,8s,9s)-8-[(2r)-2-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]-2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0²,⁷]dodec-3-ene-3-carboxylate)

PDB for NP0220277 (methyl (1r,2s,7r,8s,9s)-8-[(2r)-2-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]-2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0²,⁷]dodec-3-ene-3-carboxylate)

3D PDB for NP0220277 (methyl (1r,2s,7r,8s,9s)-8-[(2r)-2-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]-2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0²,⁷]dodec-3-ene-3-carboxylate)

SMILES for NP0220277 (methyl (1r,2s,7r,8s,9s)-8-[(2r)-2-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]-2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0²,⁷]dodec-3-ene-3-carboxylate)

INCHI for NP0220277 (methyl (1r,2s,7r,8s,9s)-8-[(2r)-2-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]-2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0²,⁷]dodec-3-ene-3-carboxylate)

Structure for NP0220277 (methyl (1r,2s,7r,8s,9s)-8-[(2r)-2-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]-2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0²,⁷]dodec-3-ene-3-carboxylate)

3D Structure for NP0220277 (methyl (1r,2s,7r,8s,9s)-8-[(2r)-2-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]-2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl]-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0²,⁷]dodec-3-ene-3-carboxylate)