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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:05:24 UTC

Update Date

2022-03-07 02:56:37 UTC

HMDB ID

HMDB0040532

Secondary Accession Numbers

HMDB40532

Metabolite Identification

Common Name

Cynaroside A

Description

Cynaroside A belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Based on a literature review a small amount of articles have been published on Cynaroside A.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 05061311552D          

 31 34  0  0  0  0            999 V2000
    4.6417    1.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8305   -1.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534    1.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9527    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3866   -1.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7384    0.0582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265    0.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7416   -1.0690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8646   -0.2532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2196    0.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4516   -0.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8409   -0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3287   -0.8560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5541    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1546   -1.2820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4370   -0.7098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6326    0.0482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3425    1.0770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8066    0.4741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9461   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3466    0.9796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5607   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9737   -1.3704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  8  1  2  0  0  0  0
  8  3  1  0  0  0  0
  9  2  1  0  0  0  0
 10  5  1  0  0  0  0
 10  8  1  0  0  0  0
 11  4  1  0  0  0  0
 12  5  1  0  0  0  0
 12  9  1  0  0  0  0
 13  6  1  0  0  0  0
 14  9  1  0  0  0  0
 14 10  1  0  0  0  0
 15 13  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 11  1  0  0  0  0
 18 14  1  0  0  0  0
 19 17  1  0  0  0  0
 21  7  1  0  0  0  0
 21 11  1  0  0  0  0
 21 20  1  0  0  0  0
 22  6  1  0  0  0  0
 23  7  1  0  0  0  0
 24 15  1  0  0  0  0
 25 16  1  0  0  0  0
 26 17  1  0  0  0  0
 27 20  2  0  0  0  0
 28 21  1  0  0  0  0
 29 12  1  0  0  0  0
 29 19  1  0  0  0  0
 30 13  1  0  0  0  0
 30 19  1  0  0  0  0
 31 18  1  0  0  0  0
 31 20  1  0  0  0  0
M  END

HMDB0040532
     RDKit          3D
Cynaroside A
 63 66  0  0  0  0  0  0  0  0999 V2000
    1.9563    3.4657   -1.3206 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3767    2.2519   -1.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8399    2.0584   -1.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1634    0.5765   -1.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0874   -0.2265   -0.0750 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8769   -0.3038    0.6894 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4064   -1.6612    0.5237 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5577   -2.4288    0.4444 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8269   -3.5445    1.0125 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4346   -1.6537   -0.4685 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0223   -1.9381   -1.7654 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8943   -1.9723   -0.2570 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2771   -1.6833    1.0292 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7386    0.5824    0.5722 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3849    1.2443   -0.6962 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0062    1.7875   -0.4116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6551    0.5298    0.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7888    0.8086    0.8566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8844    0.2447    0.2209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5226   -0.7016    1.0271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5108   -1.2982    0.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1599   -2.4647    0.9624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7258   -1.9569    2.1342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6051   -0.2835   -0.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6653   -0.8882   -0.6826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9892    0.8202   -0.8760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6239    0.2350   -2.0824 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8299    1.3839   -0.1217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2931    1.8973    1.0811 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4217   -0.1439    0.9036 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1724   -0.1255    2.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6347    4.2868   -1.5873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9007    3.7521   -1.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3766    2.3748   -0.1959 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2590    2.5749   -2.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2153    0.5525   -1.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5462    0.1642   -2.1551 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9718    0.1071    0.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1558   -0.3178    1.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6815   -2.4580   -2.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0271   -3.0445   -0.4319 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4594   -1.3947   -1.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5268   -1.5408    1.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7708    1.4023    1.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546    0.4941   -1.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5005    2.1858   -1.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0156    2.5228    0.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9120   -0.0770   -0.7994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5995   -0.2934   -0.7226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1357   -1.6564   -0.7211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4325   -3.2559    1.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0095   -2.7944    0.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3680   -2.4070    2.9367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9290    0.1058    0.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0156   -0.3225   -1.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7246    1.6392   -1.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4137    0.3424   -2.6892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2521    2.1339   -0.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5151    1.8525    1.7172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5577   -1.1861    0.5524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1332    0.0110    2.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3137   -1.0866    2.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5239    0.7212    2.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
  6 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
 21 22  1  0
 22 23  1  0
 21 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 17 30  1  0
 30 31  1  0
 15  2  1  0
 28 19  1  0
 10  5  1  0
 30 14  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  6 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 19 49  1  0
 21 50  1  0
 22 51  1  0
 22 52  1  0
 23 53  1  0
 24 54  1  0
 25 55  1  0
 26 56  1  0
 27 57  1  0
 28 58  1  0
 29 59  1  0
 30 60  1  0
 31 61  1  0
 31 62  1  0
 31 63  1  0
M  END


  Mrv0541 05061311552D          

 31 34  0  0  0  0            999 V2000
    4.6417    1.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8305   -1.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534    1.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9527    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3866   -1.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7384    0.0582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265    0.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7416   -1.0690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8646   -0.2532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2196    0.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4516   -0.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8409   -0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3287   -0.8560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5541    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1546   -1.2820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4370   -0.7098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6326    0.0482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3425    1.0770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8066    0.4741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9461   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3466    0.9796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5607   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9737   -1.3704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  8  1  2  0  0  0  0
  8  3  1  0  0  0  0
  9  2  1  0  0  0  0
 10  5  1  0  0  0  0
 10  8  1  0  0  0  0
 11  4  1  0  0  0  0
 12  5  1  0  0  0  0
 12  9  1  0  0  0  0
 13  6  1  0  0  0  0
 14  9  1  0  0  0  0
 14 10  1  0  0  0  0
 15 13  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 11  1  0  0  0  0
 18 14  1  0  0  0  0
 19 17  1  0  0  0  0
 21  7  1  0  0  0  0
 21 11  1  0  0  0  0
 21 20  1  0  0  0  0
 22  6  1  0  0  0  0
 23  7  1  0  0  0  0
 24 15  1  0  0  0  0
 25 16  1  0  0  0  0
 26 17  1  0  0  0  0
 27 20  2  0  0  0  0
 28 21  1  0  0  0  0
 29 12  1  0  0  0  0
 29 19  1  0  0  0  0
 30 13  1  0  0  0  0
 30 19  1  0  0  0  0
 31 18  1  0  0  0  0
 31 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040532

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C(CC2C1C1OC(=O)C(O)(CO)C1CCC2=C)OC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O10/c1-8-3-4-11-18(31-20(27)21(11,28)7-23)14-9(2)12(5-10(8)14)29-19-17(26)16(25)15(24)13(6-22)30-19/h9-19,22-26,28H,1,3-7H2,2H3

> <INCHI_KEY>
MVSPYXAIGOWGGA-UHFFFAOYSA-N

> <FORMULA>
C21H32O10

> <MOLECULAR_WEIGHT>
444.4728

> <EXACT_MASS>
444.199547244

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
45.43465949424084

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-hydroxy-3-(hydroxymethyl)-9-methyl-6-methylidene-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydroazuleno[4,5-b]furan-2-one

> <ALOGPS_LOGP>
-1.39

> <JCHEM_LOGP>
-1.7849936713333334

> <ALOGPS_LOGS>
-1.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.261107784865406

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.304404305682302

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083542786669

> <JCHEM_POLAR_SURFACE_AREA>
166.13999999999996

> <JCHEM_REFRACTIVITY>
103.47219999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.20e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-3-(hydroxymethyl)-9-methyl-6-methylidene-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydro-3aH-azuleno[4,5-b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040532
     RDKit          3D
Cynaroside A
 63 66  0  0  0  0  0  0  0  0999 V2000
    1.9563    3.4657   -1.3206 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3767    2.2519   -1.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8399    2.0584   -1.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1634    0.5765   -1.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0874   -0.2265   -0.0750 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8769   -0.3038    0.6894 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4064   -1.6612    0.5237 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5577   -2.4288    0.4444 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8269   -3.5445    1.0125 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4346   -1.6537   -0.4685 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0223   -1.9381   -1.7654 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8943   -1.9723   -0.2570 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2771   -1.6833    1.0292 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7386    0.5824    0.5722 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3849    1.2443   -0.6962 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0062    1.7875   -0.4116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6551    0.5298    0.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7888    0.8086    0.8566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8844    0.2447    0.2209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5226   -0.7016    1.0271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5108   -1.2982    0.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1599   -2.4647    0.9624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7258   -1.9569    2.1342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6051   -0.2835   -0.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6653   -0.8882   -0.6826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9892    0.8202   -0.8760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6239    0.2350   -2.0824 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8299    1.3839   -0.1217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2931    1.8973    1.0811 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4217   -0.1439    0.9036 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1724   -0.1255    2.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6347    4.2868   -1.5873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9007    3.7521   -1.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3766    2.3748   -0.1959 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2590    2.5749   -2.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2153    0.5525   -1.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5462    0.1642   -2.1551 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9718    0.1071    0.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1558   -0.3178    1.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6815   -2.4580   -2.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0271   -3.0445   -0.4319 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4594   -1.3947   -1.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5268   -1.5408    1.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7708    1.4023    1.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546    0.4941   -1.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5005    2.1858   -1.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0156    2.5228    0.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9120   -0.0770   -0.7994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5995   -0.2934   -0.7226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1357   -1.6564   -0.7211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4325   -3.2559    1.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0095   -2.7944    0.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3680   -2.4070    2.9367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9290    0.1058    0.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0156   -0.3225   -1.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7246    1.6392   -1.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4137    0.3424   -2.6892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2521    2.1339   -0.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5151    1.8525    1.7172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5577   -1.1861    0.5524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1332    0.0110    2.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3137   -1.0866    2.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5239    0.7212    2.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
  6 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
 21 22  1  0
 22 23  1  0
 21 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 17 30  1  0
 30 31  1  0
 15  2  1  0
 28 19  1  0
 10  5  1  0
 30 14  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  6 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 19 49  1  0
 21 50  1  0
 22 51  1  0
 22 52  1  0
 23 53  1  0
 24 54  1  0
 25 55  1  0
 26 56  1  0
 27 57  1  0
 28 58  1  0
 29 59  1  0
 30 60  1  0
 31 61  1  0
 31 62  1  0
 31 63  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       8.665   3.341   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.150  -3.052   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.073   3.049   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.686   2.381   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.245   0.338   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.655  -2.956   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.378   0.109   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.461   2.381   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.691  -1.610   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.803   0.879   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.343   0.879   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.176  -1.200   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.451  -1.995   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.843  -0.325   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.681  -0.473   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.477   0.488   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.043  -0.075   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.303  -0.325   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.814  -1.598   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.970  -1.200   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.901   0.338   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      17.089  -2.393   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.816  -1.325   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      16.114   0.090   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      13.706   2.010   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      10.839   0.885   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       1.766  -2.160   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       2.514   1.829   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      10.380  -2.160   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      13.018  -2.558   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       4.455  -1.610   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3    4    8                                                       
CONECT    4    3   11                                                       
CONECT    5   10   12                                                       
CONECT    6   13   22                                                       
CONECT    7   21   23                                                       
CONECT    8    1    3   10                                                  
CONECT    9    2   12   14                                                  
CONECT   10    5    8   14                                                  
CONECT   11    4   18   21                                                  
CONECT   12    5    9   29                                                  
CONECT   13    6   15   30                                                  
CONECT   14    9   10   18                                                  
CONECT   15   13   16   24                                                  
CONECT   16   15   17   25                                                  
CONECT   17   16   19   26                                                  
CONECT   18   11   14   31                                                  
CONECT   19   17   29   30                                                  
CONECT   20   21   27   31                                                  
CONECT   21    7   11   20   28                                             
CONECT   22    6                                                            
CONECT   23    7                                                            
CONECT   24   15                                                            
CONECT   25   16                                                            
CONECT   26   17                                                            
CONECT   27   20                                                            
CONECT   28   21                                                            
CONECT   29   12   19                                                       
CONECT   30   13   19                                                       
CONECT   31   18   20                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

COMPND    HMDB0040532
HETATM    1  C1  UNL     1       1.956   3.466  -1.321  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.377   2.252  -1.036  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.840   2.058  -1.098  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.163   0.576  -1.324  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.087  -0.226  -0.075  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.877  -0.304   0.689  1.00  0.00           C  
HETATM    7  O1  UNL     1       2.406  -1.661   0.524  1.00  0.00           O  
HETATM    8  C7  UNL     1       3.558  -2.429   0.444  1.00  0.00           C  
HETATM    9  O2  UNL     1       3.827  -3.544   1.012  1.00  0.00           O  
HETATM   10  C8  UNL     1       4.435  -1.654  -0.469  1.00  0.00           C  
HETATM   11  O3  UNL     1       4.022  -1.938  -1.765  1.00  0.00           O  
HETATM   12  C9  UNL     1       5.894  -1.972  -0.257  1.00  0.00           C  
HETATM   13  O4  UNL     1       6.277  -1.683   1.029  1.00  0.00           O  
HETATM   14  C10 UNL     1       1.739   0.582   0.572  1.00  0.00           C  
HETATM   15  C11 UNL     1       1.385   1.244  -0.696  1.00  0.00           C  
HETATM   16  C12 UNL     1       0.006   1.788  -0.412  1.00  0.00           C  
HETATM   17  C13 UNL     1      -0.655   0.530   0.118  1.00  0.00           C  
HETATM   18  O5  UNL     1      -1.789   0.809   0.857  1.00  0.00           O  
HETATM   19  C14 UNL     1      -2.884   0.245   0.221  1.00  0.00           C  
HETATM   20  O6  UNL     1      -3.523  -0.702   1.027  1.00  0.00           O  
HETATM   21  C15 UNL     1      -4.511  -1.298   0.249  1.00  0.00           C  
HETATM   22  C16 UNL     1      -5.160  -2.465   0.962  1.00  0.00           C  
HETATM   23  O7  UNL     1      -5.726  -1.957   2.134  1.00  0.00           O  
HETATM   24  C17 UNL     1      -5.605  -0.284  -0.023  1.00  0.00           C  
HETATM   25  O8  UNL     1      -6.665  -0.888  -0.683  1.00  0.00           O  
HETATM   26  C18 UNL     1      -4.989   0.820  -0.876  1.00  0.00           C  
HETATM   27  O9  UNL     1      -4.624   0.235  -2.082  1.00  0.00           O  
HETATM   28  C19 UNL     1      -3.830   1.384  -0.122  1.00  0.00           C  
HETATM   29  O10 UNL     1      -4.293   1.897   1.081  1.00  0.00           O  
HETATM   30  C20 UNL     1       0.422  -0.144   0.904  1.00  0.00           C  
HETATM   31  C21 UNL     1       0.172  -0.125   2.395  1.00  0.00           C  
HETATM   32  H1  UNL     1       2.635   4.287  -1.587  1.00  0.00           H  
HETATM   33  H2  UNL     1       0.901   3.752  -1.314  1.00  0.00           H  
HETATM   34  H3  UNL     1       4.377   2.375  -0.196  1.00  0.00           H  
HETATM   35  H4  UNL     1       4.259   2.575  -2.010  1.00  0.00           H  
HETATM   36  H5  UNL     1       5.215   0.552  -1.680  1.00  0.00           H  
HETATM   37  H6  UNL     1       3.546   0.164  -2.155  1.00  0.00           H  
HETATM   38  H7  UNL     1       4.972   0.107   0.553  1.00  0.00           H  
HETATM   39  H8  UNL     1       3.156  -0.318   1.797  1.00  0.00           H  
HETATM   40  H9  UNL     1       4.681  -2.458  -2.278  1.00  0.00           H  
HETATM   41  H10 UNL     1       6.027  -3.044  -0.432  1.00  0.00           H  
HETATM   42  H11 UNL     1       6.459  -1.395  -1.024  1.00  0.00           H  
HETATM   43  H12 UNL     1       5.527  -1.541   1.653  1.00  0.00           H  
HETATM   44  H13 UNL     1       1.771   1.402   1.358  1.00  0.00           H  
HETATM   45  H14 UNL     1       1.255   0.494  -1.517  1.00  0.00           H  
HETATM   46  H15 UNL     1      -0.500   2.186  -1.304  1.00  0.00           H  
HETATM   47  H16 UNL     1      -0.016   2.523   0.409  1.00  0.00           H  
HETATM   48  H17 UNL     1      -0.912  -0.077  -0.799  1.00  0.00           H  
HETATM   49  H18 UNL     1      -2.600  -0.293  -0.723  1.00  0.00           H  
HETATM   50  H19 UNL     1      -4.136  -1.656  -0.721  1.00  0.00           H  
HETATM   51  H20 UNL     1      -4.433  -3.256   1.152  1.00  0.00           H  
HETATM   52  H21 UNL     1      -6.009  -2.794   0.323  1.00  0.00           H  
HETATM   53  H22 UNL     1      -5.368  -2.407   2.937  1.00  0.00           H  
HETATM   54  H23 UNL     1      -5.929   0.106   0.964  1.00  0.00           H  
HETATM   55  H24 UNL     1      -7.016  -0.323  -1.411  1.00  0.00           H  
HETATM   56  H25 UNL     1      -5.725   1.639  -1.045  1.00  0.00           H  
HETATM   57  H26 UNL     1      -5.414   0.342  -2.689  1.00  0.00           H  
HETATM   58  H27 UNL     1      -3.252   2.134  -0.690  1.00  0.00           H  
HETATM   59  H28 UNL     1      -3.515   1.853   1.717  1.00  0.00           H  
HETATM   60  H29 UNL     1       0.558  -1.186   0.552  1.00  0.00           H  
HETATM   61  H30 UNL     1       1.133   0.011   2.935  1.00  0.00           H  
HETATM   62  H31 UNL     1      -0.314  -1.087   2.659  1.00  0.00           H  
HETATM   63  H32 UNL     1      -0.524   0.721   2.587  1.00  0.00           H  
CONECT    1    2    2   32   33
CONECT    2    3   15
CONECT    3    4   34   35
CONECT    4    5   36   37
CONECT    5    6   10   38
CONECT    6    7   14   39
CONECT    7    8
CONECT    8    9    9   10
CONECT   10   11   12
CONECT   11   40
CONECT   12   13   41   42
CONECT   13   43
CONECT   14   15   30   44
CONECT   15   16   45
CONECT   16   17   46   47
CONECT   17   18   30   48
CONECT   18   19
CONECT   19   20   28   49
CONECT   20   21
CONECT   21   22   24   50
CONECT   22   23   51   52
CONECT   23   53
CONECT   24   25   26   54
CONECT   25   55
CONECT   26   27   28   56
CONECT   27   57
CONECT   28   29   58
CONECT   29   59
CONECT   30   31   60
CONECT   31   61   62   63
END

HMDB0040532
     RDKit          3D
Cynaroside A
 63 66  0  0  0  0  0  0  0  0999 V2000
    1.9563    3.4657   -1.3206 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3767    2.2519   -1.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8399    2.0584   -1.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1634    0.5765   -1.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0874   -0.2265   -0.0750 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8769   -0.3038    0.6894 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4064   -1.6612    0.5237 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5577   -2.4288    0.4444 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8269   -3.5445    1.0125 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4346   -1.6537   -0.4685 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0223   -1.9381   -1.7654 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8943   -1.9723   -0.2570 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2771   -1.6833    1.0292 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7386    0.5824    0.5722 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3849    1.2443   -0.6962 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0062    1.7875   -0.4116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6551    0.5298    0.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7888    0.8086    0.8566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8844    0.2447    0.2209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5226   -0.7016    1.0271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5108   -1.2982    0.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1599   -2.4647    0.9624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7258   -1.9569    2.1342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6051   -0.2835   -0.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6653   -0.8882   -0.6826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9892    0.8202   -0.8760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6239    0.2350   -2.0824 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8299    1.3839   -0.1217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2931    1.8973    1.0811 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4217   -0.1439    0.9036 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1724   -0.1255    2.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6347    4.2868   -1.5873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9007    3.7521   -1.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3766    2.3748   -0.1959 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2590    2.5749   -2.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2153    0.5525   -1.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5462    0.1642   -2.1551 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9718    0.1071    0.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1558   -0.3178    1.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6815   -2.4580   -2.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0271   -3.0445   -0.4319 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4594   -1.3947   -1.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5268   -1.5408    1.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7708    1.4023    1.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546    0.4941   -1.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5005    2.1858   -1.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0156    2.5228    0.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9120   -0.0770   -0.7994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5995   -0.2934   -0.7226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1357   -1.6564   -0.7211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4325   -3.2559    1.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0095   -2.7944    0.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3680   -2.4070    2.9367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9290    0.1058    0.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0156   -0.3225   -1.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7246    1.6392   -1.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4137    0.3424   -2.6892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2521    2.1339   -0.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5151    1.8525    1.7172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5577   -1.1861    0.5524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1332    0.0110    2.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3137   -1.0866    2.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5239    0.7212    2.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
  6 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
 21 22  1  0
 22 23  1  0
 21 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 17 30  1  0
 30 31  1  0
 15  2  1  0
 28 19  1  0
 10  5  1  0
 30 14  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  6 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 19 49  1  0
 21 50  1  0
 22 51  1  0
 22 52  1  0
 23 53  1  0
 24 54  1  0
 25 55  1  0
 26 56  1  0
 27 57  1  0
 28 58  1  0
 29 59  1  0
 30 60  1  0
 31 61  1  0
 31 62  1  0
 31 63  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₁H₃₂O₁₀

Average Molecular Weight

444.4728

Monoisotopic Molecular Weight

444.199547244

IUPAC Name

3-hydroxy-3-(hydroxymethyl)-9-methyl-6-methylidene-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydroazuleno[4,5-b]furan-2-one

Traditional Name

3-hydroxy-3-(hydroxymethyl)-9-methyl-6-methylidene-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydro-3aH-azuleno[4,5-b]furan-2-one

CAS Registry Number

117804-06-5

SMILES

CC1C(CC2C1C1OC(=O)C(O)(CO)C1CCC2=C)OC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C21H32O10/c1-8-3-4-11-18(31-20(27)21(11,28)7-23)14-9(2)12(5-10(8)14)29-19-17(26)16(25)15(24)13(6-22)30-19/h9-19,22-26,28H,1,3-7H2,2H3

InChI Key

MVSPYXAIGOWGGA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Terpene glycoside
Guaiane sesquiterpenoid
Sesquiterpenoid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Gamma butyrolactone
Monosaccharide
Oxane
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Lactone
Monocarboxylic acid or derivatives
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Primary alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0040532)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040532)

Source

Endogenous

Endogenous (HMDB: HMDB0040532)

Plant

Plant (HMDB: HMDB0040532)

Animal

Animal (HMDB: HMDB0040532)

Exogenous

Food

Food (HMDB: HMDB0040532)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0040532)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0040532)

Cellular process

Cell signaling (HMDB: HMDB0040532)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0040532)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0040532)

Nutrient

Nutrient (HMDB: HMDB0040532)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0040532)

Emulsifier (HMDB: HMDB0040532)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	2888 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	12 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-1.8	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	11.3	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	166.14 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	103.47 m³·mol⁻¹	ChemAxon
Polarizability	45.43 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	202.221	31661259
DarkChem	[M-H]-	193.953	31661259
DeepCCS	[M+H]+	196.089	30932474
DeepCCS	[M-H]-	193.731	30932474
DeepCCS	[M-2H]-	227.673	30932474
DeepCCS	[M+Na]+	202.901	30932474
AllCCS	[M+H]+	204.1	32859911
AllCCS	[M+H-H2O]+	202.1	32859911
AllCCS	[M+NH4]+	206.0	32859911
AllCCS	[M+Na]+	206.5	32859911
AllCCS	[M-H]-	200.1	32859911
AllCCS	[M+Na-2H]-	200.6	32859911
AllCCS	[M+HCOO]-	201.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cynaroside A	CC1C(CC2C1C1OC(=O)C(O)(CO)C1CCC2=C)OC1OC(CO)C(O)C(O)C1O	3277.0	Standard polar	33892256
Cynaroside A	CC1C(CC2C1C1OC(=O)C(O)(CO)C1CCC2=C)OC1OC(CO)C(O)C(O)C1O	3545.9	Standard non polar	33892256
Cynaroside A	CC1C(CC2C1C1OC(=O)C(O)(CO)C1CCC2=C)OC1OC(CO)C(O)C(O)C1O	3690.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cynaroside A,1TMS,isomer #1	C=C1CCC2C(OC(=O)C2(CO)O[Si](C)(C)C)C2C1CC(OC1OC(CO)C(O)C(O)C1O)C2C	3619.3	Semi standard non polar	33892256
Cynaroside A,1TMS,isomer #2	C=C1CCC2C(OC(=O)C2(O)CO[Si](C)(C)C)C2C1CC(OC1OC(CO)C(O)C(O)C1O)C2C	3547.3	Semi standard non polar	33892256
Cynaroside A,1TMS,isomer #3	C=C1CCC2C(OC(=O)C2(O)CO)C2C1CC(OC1OC(CO[Si](C)(C)C)C(O)C(O)C1O)C2C	3564.0	Semi standard non polar	33892256
Cynaroside A,1TMS,isomer #4	C=C1CCC2C(OC(=O)C2(O)CO)C2C1CC(OC1OC(CO)C(O[Si](C)(C)C)C(O)C1O)C2C	3557.6	Semi standard non polar	33892256
Cynaroside A,1TMS,isomer #5	C=C1CCC2C(OC(=O)C2(O)CO)C2C1CC(OC1OC(CO)C(O)C(O[Si](C)(C)C)C1O)C2C	3538.5	Semi standard non polar	33892256
Cynaroside A,1TMS,isomer #6	C=C1CCC2C(OC(=O)C2(O)CO)C2C1CC(OC1OC(CO)C(O)C(O)C1O[Si](C)(C)C)C2C	3541.4	Semi standard non polar	33892256
Cynaroside A,2TMS,isomer #1	C=C1CCC2C(OC(=O)C2(CO[Si](C)(C)C)O[Si](C)(C)C)C2C1CC(OC1OC(CO)C(O)C(O)C1O)C2C	3554.8	Semi standard non polar	33892256
Cynaroside A,2TMS,isomer #10	C=C1CCC2C(OC(=O)C2(O)CO)C2C1CC(OC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C1O)C2C	3506.3	Semi standard non polar	33892256
Cynaroside A,2TMS,isomer #11	C=C1CCC2C(OC(=O)C2(O)CO)C2C1CC(OC1OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C1O)C2C	3486.0	Semi standard non polar	33892256
Cynaroside A,2TMS,isomer #12	C=C1CCC2C(OC(=O)C2(O)CO)C2C1CC(OC1OC(CO[Si](C)(C)C)C(O)C(O)C1O[Si](C)(C)C)C2C	3492.1	Semi standard non polar	33892256
Cynaroside A,2TMS,isomer #13	C=C1CCC2C(OC(=O)C2(O)CO)C2C1CC(OC1OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O)C2C	3485.7	Semi standard non polar	33892256
Cynaroside A,2TMS,isomer #14	C=C1CCC2C(OC(=O)C2(O)CO)C2C1CC(OC1OC(CO)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C)C2C	3482.0	Semi standard non polar	33892256
Cynaroside A,2TMS,isomer #15	C=C1CCC2C(OC(=O)C2(O)CO)C2C1CC(OC1OC(CO)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C)C2C	3480.0	Semi standard non polar	33892256
Cynaroside A,2TMS,isomer #2	C=C1CCC2C(OC(=O)C2(CO)O[Si](C)(C)C)C2C1CC(OC1OC(CO[Si](C)(C)C)C(O)C(O)C1O)C2C	3563.3	Semi standard non polar	33892256
Cynaroside A,2TMS,isomer #3	C=C1CCC2C(OC(=O)C2(CO)O[Si](C)(C)C)C2C1CC(OC1OC(CO)C(O[Si](C)(C)C)C(O)C1O)C2C	3567.7	Semi standard non polar	33892256
Cynaroside A,2TMS,isomer #4	C=C1CCC2C(OC(=O)C2(CO)O[Si](C)(C)C)C2C1CC(OC1OC(CO)C(O)C(O[Si](C)(C)C)C1O)C2C	3542.6	Semi standard non polar	33892256
Cynaroside A,2TMS,isomer #5	C=C1CCC2C(OC(=O)C2(CO)O[Si](C)(C)C)C2C1CC(OC1OC(CO)C(O)C(O)C1O[Si](C)(C)C)C2C	3546.9	Semi standard non polar	33892256
Cynaroside A,2TMS,isomer #6	C=C1CCC2C(OC(=O)C2(O)CO[Si](C)(C)C)C2C1CC(OC1OC(CO[Si](C)(C)C)C(O)C(O)C1O)C2C	3485.2	Semi standard non polar	33892256
Cynaroside A,2TMS,isomer #7	C=C1CCC2C(OC(=O)C2(O)CO[Si](C)(C)C)C2C1CC(OC1OC(CO)C(O[Si](C)(C)C)C(O)C1O)C2C	3487.5	Semi standard non polar	33892256
Cynaroside A,2TMS,isomer #8	C=C1CCC2C(OC(=O)C2(O)CO[Si](C)(C)C)C2C1CC(OC1OC(CO)C(O)C(O[Si](C)(C)C)C1O)C2C	3463.2	Semi standard non polar	33892256
Cynaroside A,2TMS,isomer #9	C=C1CCC2C(OC(=O)C2(O)CO[Si](C)(C)C)C2C1CC(OC1OC(CO)C(O)C(O)C1O[Si](C)(C)C)C2C	3466.8	Semi standard non polar	33892256
Cynaroside A,3TMS,isomer #1	C=C1CCC2C(OC(=O)C2(CO[Si](C)(C)C)O[Si](C)(C)C)C2C1CC(OC1OC(CO[Si](C)(C)C)C(O)C(O)C1O)C2C	3463.5	Semi standard non polar	33892256
Cynaroside A,3TMS,isomer #10	C=C1CCC2C(OC(=O)C2(CO)O[Si](C)(C)C)C2C1CC(OC1OC(CO)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C)C2C	3471.4	Semi standard non polar	33892256
Cynaroside A,3TMS,isomer #11	C=C1CCC2C(OC(=O)C2(O)CO[Si](C)(C)C)C2C1CC(OC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C1O)C2C	3423.7	Semi standard non polar	33892256
Cynaroside A,3TMS,isomer #12	C=C1CCC2C(OC(=O)C2(O)CO[Si](C)(C)C)C2C1CC(OC1OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C1O)C2C	3404.2	Semi standard non polar	33892256
Cynaroside A,3TMS,isomer #13	C=C1CCC2C(OC(=O)C2(O)CO[Si](C)(C)C)C2C1CC(OC1OC(CO[Si](C)(C)C)C(O)C(O)C1O[Si](C)(C)C)C2C	3402.0	Semi standard non polar	33892256
Cynaroside A,3TMS,isomer #14	C=C1CCC2C(OC(=O)C2(O)CO[Si](C)(C)C)C2C1CC(OC1OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O)C2C	3401.0	Semi standard non polar	33892256
Cynaroside A,3TMS,isomer #15	C=C1CCC2C(OC(=O)C2(O)CO[Si](C)(C)C)C2C1CC(OC1OC(CO)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C)C2C	3406.5	Semi standard non polar	33892256
Cynaroside A,3TMS,isomer #16	C=C1CCC2C(OC(=O)C2(O)CO[Si](C)(C)C)C2C1CC(OC1OC(CO)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C)C2C	3396.2	Semi standard non polar	33892256
Cynaroside A,3TMS,isomer #17	C=C1CCC2C(OC(=O)C2(O)CO)C2C1CC(OC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O)C2C	3435.6	Semi standard non polar	33892256
Cynaroside A,3TMS,isomer #18	C=C1CCC2C(OC(=O)C2(O)CO)C2C1CC(OC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C)C2C	3431.0	Semi standard non polar	33892256
Cynaroside A,3TMS,isomer #19	C=C1CCC2C(OC(=O)C2(O)CO)C2C1CC(OC1OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C)C2C	3423.5	Semi standard non polar	33892256
Cynaroside A,3TMS,isomer #2	C=C1CCC2C(OC(=O)C2(CO[Si](C)(C)C)O[Si](C)(C)C)C2C1CC(OC1OC(CO)C(O[Si](C)(C)C)C(O)C1O)C2C	3477.9	Semi standard non polar	33892256
Cynaroside A,3TMS,isomer #20	C=C1CCC2C(OC(=O)C2(O)CO)C2C1CC(OC1OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C)C2C	3426.2	Semi standard non polar	33892256
Cynaroside A,3TMS,isomer #3	C=C1CCC2C(OC(=O)C2(CO[Si](C)(C)C)O[Si](C)(C)C)C2C1CC(OC1OC(CO)C(O)C(O[Si](C)(C)C)C1O)C2C	3449.7	Semi standard non polar	33892256
Cynaroside A,3TMS,isomer #4	C=C1CCC2C(OC(=O)C2(CO[Si](C)(C)C)O[Si](C)(C)C)C2C1CC(OC1OC(CO)C(O)C(O)C1O[Si](C)(C)C)C2C	3446.6	Semi standard non polar	33892256
Cynaroside A,3TMS,isomer #5	C=C1CCC2C(OC(=O)C2(CO)O[Si](C)(C)C)C2C1CC(OC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C1O)C2C	3494.1	Semi standard non polar	33892256
Cynaroside A,3TMS,isomer #6	C=C1CCC2C(OC(=O)C2(CO)O[Si](C)(C)C)C2C1CC(OC1OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C1O)C2C	3473.2	Semi standard non polar	33892256
Cynaroside A,3TMS,isomer #7	C=C1CCC2C(OC(=O)C2(CO)O[Si](C)(C)C)C2C1CC(OC1OC(CO[Si](C)(C)C)C(O)C(O)C1O[Si](C)(C)C)C2C	3470.4	Semi standard non polar	33892256
Cynaroside A,3TMS,isomer #8	C=C1CCC2C(OC(=O)C2(CO)O[Si](C)(C)C)C2C1CC(OC1OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O)C2C	3480.8	Semi standard non polar	33892256
Cynaroside A,3TMS,isomer #9	C=C1CCC2C(OC(=O)C2(CO)O[Si](C)(C)C)C2C1CC(OC1OC(CO)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C)C2C	3479.8	Semi standard non polar	33892256
Cynaroside A,4TMS,isomer #1	C=C1CCC2C(OC(=O)C2(CO[Si](C)(C)C)O[Si](C)(C)C)C2C1CC(OC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C1O)C2C	3386.8	Semi standard non polar	33892256
Cynaroside A,4TMS,isomer #10	C=C1CCC2C(OC(=O)C2(CO)O[Si](C)(C)C)C2C1CC(OC1OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C)C2C	3382.1	Semi standard non polar	33892256
Cynaroside A,4TMS,isomer #11	C=C1CCC2C(OC(=O)C2(O)CO[Si](C)(C)C)C2C1CC(OC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O)C2C	3325.2	Semi standard non polar	33892256
Cynaroside A,4TMS,isomer #12	C=C1CCC2C(OC(=O)C2(O)CO[Si](C)(C)C)C2C1CC(OC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C)C2C	3335.8	Semi standard non polar	33892256
Cynaroside A,4TMS,isomer #13	C=C1CCC2C(OC(=O)C2(O)CO[Si](C)(C)C)C2C1CC(OC1OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C)C2C	3326.1	Semi standard non polar	33892256
Cynaroside A,4TMS,isomer #14	C=C1CCC2C(OC(=O)C2(O)CO[Si](C)(C)C)C2C1CC(OC1OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C)C2C	3313.1	Semi standard non polar	33892256
Cynaroside A,4TMS,isomer #15	C=C1CCC2C(OC(=O)C2(O)CO)C2C1CC(OC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C)C2C	3361.6	Semi standard non polar	33892256
Cynaroside A,4TMS,isomer #2	C=C1CCC2C(OC(=O)C2(CO[Si](C)(C)C)O[Si](C)(C)C)C2C1CC(OC1OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C1O)C2C	3349.9	Semi standard non polar	33892256
Cynaroside A,4TMS,isomer #3	C=C1CCC2C(OC(=O)C2(CO[Si](C)(C)C)O[Si](C)(C)C)C2C1CC(OC1OC(CO[Si](C)(C)C)C(O)C(O)C1O[Si](C)(C)C)C2C	3364.5	Semi standard non polar	33892256
Cynaroside A,4TMS,isomer #4	C=C1CCC2C(OC(=O)C2(CO[Si](C)(C)C)O[Si](C)(C)C)C2C1CC(OC1OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O)C2C	3355.6	Semi standard non polar	33892256
Cynaroside A,4TMS,isomer #5	C=C1CCC2C(OC(=O)C2(CO[Si](C)(C)C)O[Si](C)(C)C)C2C1CC(OC1OC(CO)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C)C2C	3376.9	Semi standard non polar	33892256
Cynaroside A,4TMS,isomer #6	C=C1CCC2C(OC(=O)C2(CO[Si](C)(C)C)O[Si](C)(C)C)C2C1CC(OC1OC(CO)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C)C2C	3357.2	Semi standard non polar	33892256
Cynaroside A,4TMS,isomer #7	C=C1CCC2C(OC(=O)C2(CO)O[Si](C)(C)C)C2C1CC(OC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O)C2C	3386.5	Semi standard non polar	33892256
Cynaroside A,4TMS,isomer #8	C=C1CCC2C(OC(=O)C2(CO)O[Si](C)(C)C)C2C1CC(OC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C)C2C	3388.4	Semi standard non polar	33892256
Cynaroside A,4TMS,isomer #9	C=C1CCC2C(OC(=O)C2(CO)O[Si](C)(C)C)C2C1CC(OC1OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C)C2C	3375.2	Semi standard non polar	33892256
Cynaroside A,5TMS,isomer #1	C=C1CCC2C(OC(=O)C2(CO[Si](C)(C)C)O[Si](C)(C)C)C2C1CC(OC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O)C2C	3295.3	Semi standard non polar	33892256
Cynaroside A,5TMS,isomer #2	C=C1CCC2C(OC(=O)C2(CO[Si](C)(C)C)O[Si](C)(C)C)C2C1CC(OC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C)C2C	3304.2	Semi standard non polar	33892256
Cynaroside A,5TMS,isomer #3	C=C1CCC2C(OC(=O)C2(CO[Si](C)(C)C)O[Si](C)(C)C)C2C1CC(OC1OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C)C2C	3288.8	Semi standard non polar	33892256
Cynaroside A,5TMS,isomer #4	C=C1CCC2C(OC(=O)C2(CO[Si](C)(C)C)O[Si](C)(C)C)C2C1CC(OC1OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C)C2C	3258.3	Semi standard non polar	33892256
Cynaroside A,5TMS,isomer #5	C=C1CCC2C(OC(=O)C2(CO)O[Si](C)(C)C)C2C1CC(OC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C)C2C	3298.2	Semi standard non polar	33892256
Cynaroside A,5TMS,isomer #6	C=C1CCC2C(OC(=O)C2(O)CO[Si](C)(C)C)C2C1CC(OC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C)C2C	3243.4	Semi standard non polar	33892256
Cynaroside A,6TMS,isomer #1	C=C1CCC2C(OC(=O)C2(CO[Si](C)(C)C)O[Si](C)(C)C)C2C1CC(OC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C)C2C	3230.1	Semi standard non polar	33892256
Cynaroside A,1TBDMS,isomer #1	C=C1CCC2C(OC(=O)C2(CO)O[Si](C)(C)C(C)(C)C)C2C1CC(OC1OC(CO)C(O)C(O)C1O)C2C	3867.2	Semi standard non polar	33892256
Cynaroside A,1TBDMS,isomer #2	C=C1CCC2C(OC(=O)C2(O)CO[Si](C)(C)C(C)(C)C)C2C1CC(OC1OC(CO)C(O)C(O)C1O)C2C	3774.4	Semi standard non polar	33892256
Cynaroside A,1TBDMS,isomer #3	C=C1CCC2C(OC(=O)C2(O)CO)C2C1CC(OC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C1O)C2C	3785.2	Semi standard non polar	33892256
Cynaroside A,1TBDMS,isomer #4	C=C1CCC2C(OC(=O)C2(O)CO)C2C1CC(OC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C1O)C2C	3800.5	Semi standard non polar	33892256
Cynaroside A,1TBDMS,isomer #5	C=C1CCC2C(OC(=O)C2(O)CO)C2C1CC(OC1OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C1O)C2C	3792.9	Semi standard non polar	33892256
Cynaroside A,1TBDMS,isomer #6	C=C1CCC2C(OC(=O)C2(O)CO)C2C1CC(OC1OC(CO)C(O)C(O)C1O[Si](C)(C)C(C)(C)C)C2C	3779.5	Semi standard non polar	33892256
Cynaroside A,2TBDMS,isomer #1	C=C1CCC2C(OC(=O)C2(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C2C1CC(OC1OC(CO)C(O)C(O)C1O)C2C	3997.5	Semi standard non polar	33892256
Cynaroside A,2TBDMS,isomer #10	C=C1CCC2C(OC(=O)C2(O)CO)C2C1CC(OC1OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O)C2C	3937.7	Semi standard non polar	33892256
Cynaroside A,2TBDMS,isomer #11	C=C1CCC2C(OC(=O)C2(O)CO)C2C1CC(OC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C1O)C2C	3932.4	Semi standard non polar	33892256
Cynaroside A,2TBDMS,isomer #12	C=C1CCC2C(OC(=O)C2(O)CO)C2C1CC(OC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C1O[Si](C)(C)C(C)(C)C)C2C	3920.2	Semi standard non polar	33892256
Cynaroside A,2TBDMS,isomer #13	C=C1CCC2C(OC(=O)C2(O)CO)C2C1CC(OC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O)C2C	3926.5	Semi standard non polar	33892256
Cynaroside A,2TBDMS,isomer #14	C=C1CCC2C(OC(=O)C2(O)CO)C2C1CC(OC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C)C2C	3926.7	Semi standard non polar	33892256
Cynaroside A,2TBDMS,isomer #15	C=C1CCC2C(OC(=O)C2(O)CO)C2C1CC(OC1OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C)C2C	3921.5	Semi standard non polar	33892256
Cynaroside A,2TBDMS,isomer #2	C=C1CCC2C(OC(=O)C2(CO)O[Si](C)(C)C(C)(C)C)C2C1CC(OC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C1O)C2C	3998.7	Semi standard non polar	33892256
Cynaroside A,2TBDMS,isomer #3	C=C1CCC2C(OC(=O)C2(CO)O[Si](C)(C)C(C)(C)C)C2C1CC(OC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C1O)C2C	4028.1	Semi standard non polar	33892256
Cynaroside A,2TBDMS,isomer #4	C=C1CCC2C(OC(=O)C2(CO)O[Si](C)(C)C(C)(C)C)C2C1CC(OC1OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C1O)C2C	4005.3	Semi standard non polar	33892256
Cynaroside A,2TBDMS,isomer #5	C=C1CCC2C(OC(=O)C2(CO)O[Si](C)(C)C(C)(C)C)C2C1CC(OC1OC(CO)C(O)C(O)C1O[Si](C)(C)C(C)(C)C)C2C	3999.1	Semi standard non polar	33892256
Cynaroside A,2TBDMS,isomer #6	C=C1CCC2C(OC(=O)C2(O)CO[Si](C)(C)C(C)(C)C)C2C1CC(OC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C1O)C2C	3925.1	Semi standard non polar	33892256
Cynaroside A,2TBDMS,isomer #7	C=C1CCC2C(OC(=O)C2(O)CO[Si](C)(C)C(C)(C)C)C2C1CC(OC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C1O)C2C	3947.2	Semi standard non polar	33892256
Cynaroside A,2TBDMS,isomer #8	C=C1CCC2C(OC(=O)C2(O)CO[Si](C)(C)C(C)(C)C)C2C1CC(OC1OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C1O)C2C	3924.2	Semi standard non polar	33892256
Cynaroside A,2TBDMS,isomer #9	C=C1CCC2C(OC(=O)C2(O)CO[Si](C)(C)C(C)(C)C)C2C1CC(OC1OC(CO)C(O)C(O)C1O[Si](C)(C)C(C)(C)C)C2C	3914.7	Semi standard non polar	33892256
Cynaroside A,3TBDMS,isomer #1	C=C1CCC2C(OC(=O)C2(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C2C1CC(OC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C1O)C2C	4118.9	Semi standard non polar	33892256
Cynaroside A,3TBDMS,isomer #10	C=C1CCC2C(OC(=O)C2(CO)O[Si](C)(C)C(C)(C)C)C2C1CC(OC1OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C)C2C	4124.8	Semi standard non polar	33892256
Cynaroside A,3TBDMS,isomer #11	C=C1CCC2C(OC(=O)C2(O)CO[Si](C)(C)C(C)(C)C)C2C1CC(OC1OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O)C2C	4081.7	Semi standard non polar	33892256
Cynaroside A,3TBDMS,isomer #12	C=C1CCC2C(OC(=O)C2(O)CO[Si](C)(C)C(C)(C)C)C2C1CC(OC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C1O)C2C	4087.4	Semi standard non polar	33892256
Cynaroside A,3TBDMS,isomer #13	C=C1CCC2C(OC(=O)C2(O)CO[Si](C)(C)C(C)(C)C)C2C1CC(OC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C1O[Si](C)(C)C(C)(C)C)C2C	4059.8	Semi standard non polar	33892256
Cynaroside A,3TBDMS,isomer #14	C=C1CCC2C(OC(=O)C2(O)CO[Si](C)(C)C(C)(C)C)C2C1CC(OC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O)C2C	4066.8	Semi standard non polar	33892256
Cynaroside A,3TBDMS,isomer #15	C=C1CCC2C(OC(=O)C2(O)CO[Si](C)(C)C(C)(C)C)C2C1CC(OC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C)C2C	4066.8	Semi standard non polar	33892256
Cynaroside A,3TBDMS,isomer #16	C=C1CCC2C(OC(=O)C2(O)CO[Si](C)(C)C(C)(C)C)C2C1CC(OC1OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C)C2C	4068.9	Semi standard non polar	33892256
Cynaroside A,3TBDMS,isomer #17	C=C1CCC2C(OC(=O)C2(O)CO)C2C1CC(OC1OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O)C2C	4072.8	Semi standard non polar	33892256
Cynaroside A,3TBDMS,isomer #18	C=C1CCC2C(OC(=O)C2(O)CO)C2C1CC(OC1OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C)C2C	4063.6	Semi standard non polar	33892256
Cynaroside A,3TBDMS,isomer #19	C=C1CCC2C(OC(=O)C2(O)CO)C2C1CC(OC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C)C2C	4070.1	Semi standard non polar	33892256
Cynaroside A,3TBDMS,isomer #2	C=C1CCC2C(OC(=O)C2(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C2C1CC(OC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C1O)C2C	4144.2	Semi standard non polar	33892256
Cynaroside A,3TBDMS,isomer #20	C=C1CCC2C(OC(=O)C2(O)CO)C2C1CC(OC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C)C2C	4045.8	Semi standard non polar	33892256
Cynaroside A,3TBDMS,isomer #3	C=C1CCC2C(OC(=O)C2(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C2C1CC(OC1OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C1O)C2C	4128.6	Semi standard non polar	33892256
Cynaroside A,3TBDMS,isomer #4	C=C1CCC2C(OC(=O)C2(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C2C1CC(OC1OC(CO)C(O)C(O)C1O[Si](C)(C)C(C)(C)C)C2C	4110.0	Semi standard non polar	33892256
Cynaroside A,3TBDMS,isomer #5	C=C1CCC2C(OC(=O)C2(CO)O[Si](C)(C)C(C)(C)C)C2C1CC(OC1OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O)C2C	4138.8	Semi standard non polar	33892256
Cynaroside A,3TBDMS,isomer #6	C=C1CCC2C(OC(=O)C2(CO)O[Si](C)(C)C(C)(C)C)C2C1CC(OC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C1O)C2C	4135.5	Semi standard non polar	33892256
Cynaroside A,3TBDMS,isomer #7	C=C1CCC2C(OC(=O)C2(CO)O[Si](C)(C)C(C)(C)C)C2C1CC(OC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C1O[Si](C)(C)C(C)(C)C)C2C	4117.2	Semi standard non polar	33892256
Cynaroside A,3TBDMS,isomer #8	C=C1CCC2C(OC(=O)C2(CO)O[Si](C)(C)C(C)(C)C)C2C1CC(OC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O)C2C	4123.7	Semi standard non polar	33892256
Cynaroside A,3TBDMS,isomer #9	C=C1CCC2C(OC(=O)C2(CO)O[Si](C)(C)C(C)(C)C)C2C1CC(OC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C)C2C	4125.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cynaroside A GC-MS (Non-derivatized) - 70eV, Positive	splash10-0nor-4337900000-102ca12ebbefe61bdbaa	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cynaroside A GC-MS (3 TMS) - 70eV, Positive	splash10-0002-3215309000-4bb84292a1109d235592	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cynaroside A GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cynaroside A 10V, Positive-QTOF	splash10-00o1-0293600000-bc16785a954ad138da39	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cynaroside A 20V, Positive-QTOF	splash10-0159-0390000000-64a2512942409427e17d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cynaroside A 40V, Positive-QTOF	splash10-016s-1940000000-6bb78c24ff5486b6a2fa	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cynaroside A 10V, Negative-QTOF	splash10-01po-0172900000-65205b1f2b95eccf9aac	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cynaroside A 20V, Negative-QTOF	splash10-01q9-0190200000-578eb16160264beb03ad	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cynaroside A 40V, Negative-QTOF	splash10-000f-2960000000-af3d4a58e943de69e8f0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cynaroside A 10V, Positive-QTOF	splash10-001j-0090700000-a89502986f86aa73b162	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cynaroside A 20V, Positive-QTOF	splash10-0159-0190000000-fe9a0302f8e4d76e259e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cynaroside A 40V, Positive-QTOF	splash10-00yi-4982000000-8cc34ec09ba424ab4655	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cynaroside A 10V, Negative-QTOF	splash10-0006-0010900000-b08281872753a78e6dc7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cynaroside A 20V, Negative-QTOF	splash10-08fu-6083900000-4e831a413e5f587fab1b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cynaroside A 40V, Negative-QTOF	splash10-08fv-4090100000-75bb8e23e2bd59322d4f	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB020300

KNApSAcK ID

C00055547

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

14138147

PDB ID

Not Available

ChEBI ID

169162

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1884131

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Cynaroside A (HMDB0040532)

MOL for HMDB0040532 (Cynaroside A)

3D MOL for HMDB0040532 (Cynaroside A)

3D SDF for HMDB0040532 (Cynaroside A)

3D-SDF for HMDB0040532 (Cynaroside A)

PDB for HMDB0040532 (Cynaroside A)

3D PDB for HMDB0040532 (Cynaroside A)

SMILES for HMDB0040532 (Cynaroside A)

INCHI for HMDB0040532 (Cynaroside A)

Structure for HMDB0040532 (Cynaroside A)

3D Structure for HMDB0040532 (Cynaroside A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra