NP-MRD: Showing NP-Card for [(4r,7s,8s,11s)-2-oxo-8-{[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[5.3.1.0⁴,¹¹]undeca-1(10),5-dien-6-yl]methyl acetate (NP0160585)

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Record Information

Version

2.0

Created at

2022-09-02 18:33:59 UTC

Updated at

2022-09-02 18:33:59 UTC

NP-MRD ID

NP0160585

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(4r,7s,8s,11s)-2-oxo-8-{[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[5.3.1.0⁴,¹¹]undeca-1(10),5-dien-6-yl]methyl acetate

Description

[(4R,7S,8S,11S)-2-oxo-8-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[5.3.1.0⁴,¹¹]Undeca-1(10),5-dien-6-yl]methyl acetate belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. [(4r,7s,8s,11s)-2-oxo-8-{[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[5.3.1.0⁴,¹¹]undeca-1(10),5-dien-6-yl]methyl acetate is found in Cruciata taurica, Globularia trichosantha, Wollastonia biflora, Morinda citrifolia, Morinda coreia, Paederia foetida, Paederia scandens, Plantago ovata and Rubia tinctorum. Based on a literature review very few articles have been published on [(4R,7S,8S,11S)-2-oxo-8-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[5.3.1.0⁴,¹¹]Undeca-1(10),5-dien-6-yl]methyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022220342D          

 29 32  0  0  1  0            999 V2000
   -1.4668   -2.1192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6424   -2.1504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2572   -2.8799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2031   -1.4520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6213   -1.4832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0605   -0.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7420   -0.0239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3673    0.5143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5569    1.3172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3792    1.3849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8076    2.0900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6977    0.6239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4764    0.3514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6297   -0.4592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0044   -0.9973    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1577   -1.8079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9364   -2.0805    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5618   -1.5423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3405   -1.8148    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9658   -1.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8125   -0.4661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4938   -2.6255    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2725   -2.8980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8685   -3.1636    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0218   -3.9742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0898   -2.8911    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4645   -3.4292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2257   -0.7248    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0724    0.0858    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  6  0  0  0
 15 28  1  0  0  0  0
 28  6  1  6  0  0  0
 28 29  1  0  0  0  0
 29 12  1  6  0  0  0
  8 29  1  0  0  0  0
M  END

     RDKit          3D

 51 54  0  0  0  0  0  0  0  0999 V2000
    1.9799   -2.8336   -1.2777 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1924   -1.4096   -1.6173 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2873   -0.8670   -1.3794 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1914   -0.6171   -2.2129 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4392    0.7399   -2.5253 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7768    1.5564   -1.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9568    2.2198   -1.1217 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9120    2.8388    0.1086 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3432    4.0879    0.5429 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6801    4.1690    1.8234 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8962    4.9225    2.7983 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6340    3.1539    1.8093 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9257    2.3922    2.5852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0258    1.5078    2.0159 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4081    0.8448    0.7582 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7201    0.0961    0.4128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5910   -1.2605    0.5424 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0268   -1.9180   -0.5813 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3865   -2.0004   -0.7085 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7215   -1.5909   -2.1498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1200   -2.4146   -3.0698 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1679   -1.0801    0.1851 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5280   -1.4248    0.0249 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8552   -1.2642    1.6446 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0702   -0.1153    2.3755 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4285   -1.6757    1.7715 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8626   -1.0245    2.8603 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8371    1.8564   -0.2003 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4184    3.0826    0.3337 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0604   -3.2326   -1.7939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9490   -3.0351   -0.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8743   -3.3835   -1.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2373    0.7987   -3.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4697    1.1359   -2.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7265    2.1680   -1.9364 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2448    2.1015    0.9218 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0804    2.4530    3.6514 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2061    0.1575    1.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4443   -1.4971    0.8632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7794   -3.0480   -0.6195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8322   -1.5682   -2.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3840   -0.5326   -2.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5045   -1.9045   -3.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9897   -0.0333   -0.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6017   -2.3665    0.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4865   -2.0627    2.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6650   -0.1466    3.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3619   -2.7719    1.8417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0296   -1.4561    3.1852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1146    2.2185   -0.7792 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0819    4.0338   -0.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 15 28  1  0
 28 29  1  0
 28  6  1  0
 29  8  1  0
 29 12  1  0
 26 17  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  5 33  1  0
  5 34  1  0
  7 35  1  0
  8 36  1  1
 13 37  1  0
 15 38  1  1
 17 39  1  1
 19 40  1  6
 20 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  6
 23 45  1  0
 24 46  1  1
 25 47  1  0
 26 48  1  1
 27 49  1  0
 28 50  1  6
 29 51  1  6
M  END


  Mrv1652309022220342D          

 29 32  0  0  1  0            999 V2000
   -1.4668   -2.1192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6424   -2.1504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2572   -2.8799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2031   -1.4520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6213   -1.4832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0605   -0.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7420   -0.0239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3673    0.5143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5569    1.3172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3792    1.3849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8076    2.0900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6977    0.6239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4764    0.3514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6297   -0.4592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0044   -0.9973    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1577   -1.8079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9364   -2.0805    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5618   -1.5423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3405   -1.8148    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9658   -1.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8125   -0.4661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4938   -2.6255    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2725   -2.8980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8685   -3.1636    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0218   -3.9742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0898   -2.8911    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4645   -3.4292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2257   -0.7248    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0724    0.0858    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  6  0  0  0
 15 28  1  0  0  0  0
 28  6  1  6  0  0  0
 28 29  1  0  0  0  0
 29 12  1  6  0  0  0
  8 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0160585

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC1=C[C@H]2OC(=O)C3=CO[C@@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]4O)[C@H]1[C@H]23

> <INCHI_IDENTIFIER>
InChI=1S/C18H22O11/c1-6(20)25-4-7-2-9-12-8(16(24)27-9)5-26-17(11(7)12)29-18-15(23)14(22)13(21)10(3-19)28-18/h2,5,9-15,17-19,21-23H,3-4H2,1H3/t9-,10-,11-,12+,13-,14+,15+,17+,18+/m1/s1

> <INCHI_KEY>
IBIPGYWNOBGEMH-DRBIVMFGSA-N

> <FORMULA>
C18H22O11

> <MOLECULAR_WEIGHT>
414.363

> <EXACT_MASS>
414.116211528

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
39.08663220709277

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(4R,7S,8S,11S)-2-oxo-8-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[5.3.1.0^{4,11}]undeca-1(10),5-dien-6-yl]methyl acetate

> <ALOGPS_LOGP>
-1.04

> <JCHEM_LOGP>
-2.407886163333333

> <ALOGPS_LOGS>
-1.37

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.198718943138346

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.207015961483672

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810847615636256

> <JCHEM_POLAR_SURFACE_AREA>
161.21

> <JCHEM_REFRACTIVITY>
90.83530000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.75e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(4R,7S,8S,11S)-2-oxo-8-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[5.3.1.0^{4,11}]undeca-1(10),5-dien-6-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.738  -3.956   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.199  -4.014   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.480  -5.376   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -0.379  -2.710   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.160  -2.769   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.980  -1.465   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.385  -0.045   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.552   0.960   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.906   2.459   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.441   2.585   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.241   3.901   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.036   1.165   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.489   0.656   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.776  -0.857   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.608  -1.862   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.894  -3.375   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.348  -3.884   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.515  -2.879   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.969  -3.388   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.136  -2.383   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.850  -0.870   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      10.255  -4.901   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      11.709  -5.410   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.088  -5.905   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.374  -7.419   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.634  -5.397   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.467  -6.401   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.155  -1.353   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.868   0.160   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                                                       
CONECT    6    5    7   28                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   29                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   29                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   28                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   26                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   17   27                                                  
CONECT   27   26                                                            
CONECT   28   15    6   29                                                  
CONECT   29   28   12    8                                                  
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Value	Source
[(4R,7S,8S,11S)-2-oxo-8-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[5.3.1.0,]undeca-1(10),5-dien-6-yl]methyl acetic acid	Generator

Chemical Formula

C₁₈H₂₂O₁₁

Average Mass

414.3630 Da

Monoisotopic Mass

414.11621 Da

IUPAC Name

[(4R,7S,8S,11S)-2-oxo-8-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[5.3.1.0^{4,11}]undeca-1(10),5-dien-6-yl]methyl acetate

Traditional Name

[(4R,7S,8S,11S)-2-oxo-8-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[5.3.1.0^{4,11}]undeca-1(10),5-dien-6-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OCC1=C[C@H]2OC(=O)C3=CO[C@@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]4O)[C@H]1[C@H]23

InChI Identifier

InChI=1S/C18H22O11/c1-6(20)25-4-7-2-9-12-8(16(24)27-9)5-26-17(11(7)12)29-18-15(23)14(22)13(21)10(3-19)28-18/h2,5,9-15,17-19,21-23H,3-4H2,1H3/t9-,10-,11-,12+,13-,14+,15+,17+,18+/m1/s1

InChI Key

IBIPGYWNOBGEMH-DRBIVMFGSA-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
Cruciata taurica	LOTUS Database	35616633
Globularia trichosantha	LOTUS Database	35616633
Melanthera biflora	LOTUS Database	35616633
Morinda citrifolia	LOTUS Database	35616633
Morinda coreia	LOTUS Database	35616633
Paederia foetida	LOTUS Database	35616633
Paederia scandens	LOTUS Database	35616633
Plantago ovata	LOTUS Database	35616633
Rubia tinctorum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

Hexose monosaccharide
O-glycosyl compound
Furopyran
Pyran
Oxane
Monosaccharide
Gamma butyrolactone
Dicarboxylic acid or derivatives
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Furan
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Acetal
Organic oxide
Hydrocarbon derivative
Primary alcohol
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-1	ALOGPS
logP	-2.4	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	161.21 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	90.84 m³·mol⁻¹	ChemAxon
Polarizability	39.09 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

110803520

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162975250

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(4r,7s,8s,11s)-2-oxo-8-{[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[5.3.1.0⁴,¹¹]undeca-1(10),5-dien-6-yl]methyl acetate (NP0160585)

MOL for NP0160585 ([(4r,7s,8s,11s)-2-oxo-8-{[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[5.3.1.0⁴,¹¹]undeca-1(10),5-dien-6-yl]methyl acetate)

3D MOL for NP0160585 ([(4r,7s,8s,11s)-2-oxo-8-{[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[5.3.1.0⁴,¹¹]undeca-1(10),5-dien-6-yl]methyl acetate)

3D SDF for NP0160585 ([(4r,7s,8s,11s)-2-oxo-8-{[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[5.3.1.0⁴,¹¹]undeca-1(10),5-dien-6-yl]methyl acetate)

3D-SDF for NP0160585 ([(4r,7s,8s,11s)-2-oxo-8-{[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[5.3.1.0⁴,¹¹]undeca-1(10),5-dien-6-yl]methyl acetate)

PDB for NP0160585 ([(4r,7s,8s,11s)-2-oxo-8-{[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[5.3.1.0⁴,¹¹]undeca-1(10),5-dien-6-yl]methyl acetate)

3D PDB for NP0160585 ([(4r,7s,8s,11s)-2-oxo-8-{[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[5.3.1.0⁴,¹¹]undeca-1(10),5-dien-6-yl]methyl acetate)

SMILES for NP0160585 ([(4r,7s,8s,11s)-2-oxo-8-{[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[5.3.1.0⁴,¹¹]undeca-1(10),5-dien-6-yl]methyl acetate)

INCHI for NP0160585 ([(4r,7s,8s,11s)-2-oxo-8-{[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[5.3.1.0⁴,¹¹]undeca-1(10),5-dien-6-yl]methyl acetate)

Structure for NP0160585 ([(4r,7s,8s,11s)-2-oxo-8-{[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[5.3.1.0⁴,¹¹]undeca-1(10),5-dien-6-yl]methyl acetate)

3D Structure for NP0160585 ([(4r,7s,8s,11s)-2-oxo-8-{[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[5.3.1.0⁴,¹¹]undeca-1(10),5-dien-6-yl]methyl acetate)