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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 06:06:08 UTC

Update Date

2021-09-23 06:06:08 UTC

HMDB ID

HMDB0302055

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Cichorioside I

Description

(3S,3aS,4R,4aS,9aS)-4-hydroxy-3,8-dimethyl-5-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2H,3H,3aH,4H,4aH,7H,9H,9aH-azuleno[6,5-b]furan-2,7-dione belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. Based on a literature review very few articles have been published on (3S,3aS,4R,4aS,9aS)-4-hydroxy-3,8-dimethyl-5-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2H,3H,3aH,4H,4aH,7H,9H,9aH-azuleno[6,5-b]furan-2,7-dione.

Structure

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

  Mrv0541 02241212182D          

 34 37  0  0  0  0            999 V2000
   -1.4143    2.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1576    2.2722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3411    1.4679    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8268    0.8229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0018    0.8229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4874    1.4679    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6710    2.2722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8658    2.6954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4871    2.1525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1628    1.3940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5473    0.1344    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2479    0.3539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2849    1.1780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9398    3.5170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4143    3.4552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2270    1.8804    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8930   -0.1605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8372   -0.6380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2153    0.0260    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1847    0.0796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7536    0.7535    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0802   -0.8212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0802   -1.6462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3657   -2.0587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6512   -1.6462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6512   -0.8212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3657   -0.4087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3657    0.4163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9368   -0.4087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7947   -2.0587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3657   -2.8837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9368   -2.0587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7946   -2.8837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5860    0.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  7  1  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  7  1  0  0  0  0
  8  2  1  0  0  0  0
  3  2  1  0  0  0  0
 10  3  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 11  1  0  0  0  0
  6  5  1  0  0  0  0
  6 13  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 14  2  0  0  0  0
  1 15  1  0  0  0  0
  6 16  1  1  0  0  0
 12 17  2  0  0  0  0
 11 18  1  1  0  0  0
  5 19  1  6  0  0  0
  4 20  1  6  0  0  0
  3 21  1  6  0  0  0
 22 23  1  0  0  0  0
 22 27  1  0  0  0  0
 23 24  1  0  0  0  0
 23 30  1  0  0  0  0
 25 24  1  0  0  0  0
 24 31  1  0  0  0  0
 25 26  1  0  0  0  0
 25 32  1  0  0  0  0
 26 27  1  0  0  0  0
 26 29  1  0  0  0  0
 27 28  1  0  0  0  0
 30 33  1  0  0  0  0
 10 34  1  0  0  0  0
 34 28  1  0  0  0  0
M  END

HMDB0302055
     RDKit          3D
Cichorioside I
 59 62  0  0  0  0  0  0  0  0999 V2000
   -2.9675   -3.0478   -1.9706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9538   -1.6449   -1.5105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8360   -1.2197   -0.9468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6648   -2.0662   -0.7728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5207   -3.2492   -1.1757 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3050   -1.2446   -0.0301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1746   -0.0479    0.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4675    1.0725    0.9484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7305    0.8539    1.4095 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7166    0.6012    0.4955 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4862   -0.4641    0.8912 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355   -0.9609   -0.1908 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1807   -2.0141    0.4006 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9972   -1.4037    1.3496 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9954    0.1398   -0.8643 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5891    0.3305   -2.2005 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0161    1.4226   -0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0007    1.3891    0.9129 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6980    1.8039    0.4913 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8800    2.2046    1.8144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5310    0.0943   -0.4035 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4825    0.6493    0.5923 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0443    1.9747    0.8622 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8793    0.8282    0.0441 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6003   -0.4384   -0.2654 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1986   -0.8272   -1.6976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9610   -0.0405   -0.2017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1055    0.9888    0.7083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1849    1.4606    1.1120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7524    1.4343    1.1208 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4674    0.8808    2.4825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9632   -3.3063   -2.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2250   -3.2354   -2.7764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8103   -3.7463   -1.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2596   -1.6509    0.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1677    1.1956    1.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3893    2.0048    0.3354 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3805    0.5132   -0.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5544   -1.4255   -0.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5726   -2.8149    0.8438 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8058   -2.4502   -0.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9363   -1.4406    1.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0657   -0.2085   -0.9465 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3723    0.6165   -2.7627 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3351    2.2404   -0.7911 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5926    1.2935    1.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2076    2.5767   -0.1190 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8343    3.1895    1.9134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4004    0.8635   -1.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4200    0.1055    1.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1224    2.4351   -0.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8181    1.5280   -0.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3403   -1.2322    0.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9453    0.0794   -2.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0180   -1.4178   -2.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6834    2.5318    1.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5679    1.3257    2.9446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3249    1.1954    3.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4732   -0.2261    2.5062 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  7 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  1  0
 26  2  1  0
 21  3  1  0
 30 24  1  0
 19 10  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  6 35  1  0
  8 36  1  0
  8 37  1  0
 10 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 15 43  1  0
 16 44  1  0
 17 45  1  0
 18 46  1  0
 19 47  1  0
 20 48  1  0
 21 49  1  6
 22 50  1  1
 23 51  1  0
 24 52  1  6
 25 53  1  1
 26 54  1  0
 26 55  1  0
 30 56  1  1
 31 57  1  0
 31 58  1  0
 31 59  1  0
M  END

  Mrv0541 02241212182D          

 34 37  0  0  0  0            999 V2000
   -1.4143    2.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1576    2.2722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3411    1.4679    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8268    0.8229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0018    0.8229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4874    1.4679    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6710    2.2722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8658    2.6954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4871    2.1525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1628    1.3940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5473    0.1344    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2479    0.3539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2849    1.1780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9398    3.5170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4143    3.4552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2270    1.8804    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8930   -0.1605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8372   -0.6380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2153    0.0260    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1847    0.0796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7536    0.7535    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0802   -0.8212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0802   -1.6462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3657   -2.0587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6512   -1.6462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6512   -0.8212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3657   -0.4087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3657    0.4163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9368   -0.4087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7947   -2.0587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3657   -2.8837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9368   -2.0587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7946   -2.8837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5860    0.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  7  1  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  7  1  0  0  0  0
  8  2  1  0  0  0  0
  3  2  1  0  0  0  0
 10  3  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 11  1  0  0  0  0
  6  5  1  0  0  0  0
  6 13  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 14  2  0  0  0  0
  1 15  1  0  0  0  0
  6 16  1  1  0  0  0
 12 17  2  0  0  0  0
 11 18  1  1  0  0  0
  5 19  1  6  0  0  0
  4 20  1  6  0  0  0
  3 21  1  6  0  0  0
 22 23  1  0  0  0  0
 22 27  1  0  0  0  0
 23 24  1  0  0  0  0
 23 30  1  0  0  0  0
 25 24  1  0  0  0  0
 24 31  1  0  0  0  0
 25 26  1  0  0  0  0
 25 32  1  0  0  0  0
 26 27  1  0  0  0  0
 26 29  1  0  0  0  0
 27 28  1  0  0  0  0
 30 33  1  0  0  0  0
 10 34  1  0  0  0  0
 34 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302055

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12CC(C)=C3C(=O)C=C(COC4OC(CO)C(O)C(O)C4O)[C@]3([H])[C@@H](O)[C@]1([H])[C@H](C)C(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O10/c1-7-3-11-14(8(2)20(28)30-11)17(25)15-9(4-10(23)13(7)15)6-29-21-19(27)18(26)16(24)12(5-22)31-21/h4,8,11-12,14-19,21-22,24-27H,3,5-6H2,1-2H3/t8-,11-,12?,14+,15-,16?,17-,18?,19?,21?/m0/s1

> <INCHI_KEY>
POOPERNNBMZLBU-YFVSWLSASA-N

> <FORMULA>
C21H28O10

> <MOLECULAR_WEIGHT>
440.441

> <EXACT_MASS>
440.168247116

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
44.0622599157134

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,3aS,4R,4aS,9aS)-4-hydroxy-3,8-dimethyl-5-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2H,3H,3aH,4H,4aH,7H,9H,9aH-azuleno[6,5-b]furan-2,7-dione

> <ALOGPS_LOGP>
-0.96

> <JCHEM_LOGP>
-1.930231469666666

> <ALOGPS_LOGS>
-1.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.993813557067519

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.179554460446267

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810835523219152

> <JCHEM_POLAR_SURFACE_AREA>
162.98000000000002

> <JCHEM_REFRACTIVITY>
104.47499999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.11e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,3aS,4R,4aS,9aS)-4-hydroxy-3,8-dimethyl-5-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3H,3aH,4H,4aH,9H,9aH-azuleno[6,5-b]furan-2,7-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302055
     RDKit          3D
Cichorioside I
 59 62  0  0  0  0  0  0  0  0999 V2000
   -2.9675   -3.0478   -1.9706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9538   -1.6449   -1.5105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8360   -1.2197   -0.9468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6648   -2.0662   -0.7728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5207   -3.2492   -1.1757 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3050   -1.2446   -0.0301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1746   -0.0479    0.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4675    1.0725    0.9484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7305    0.8539    1.4095 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7166    0.6012    0.4955 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4862   -0.4641    0.8912 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355   -0.9609   -0.1908 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1807   -2.0141    0.4006 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9972   -1.4037    1.3496 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9954    0.1398   -0.8643 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5891    0.3305   -2.2005 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0161    1.4226   -0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0007    1.3891    0.9129 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6980    1.8039    0.4913 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8800    2.2046    1.8144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5310    0.0943   -0.4035 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4825    0.6493    0.5923 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0443    1.9747    0.8622 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8793    0.8282    0.0441 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6003   -0.4384   -0.2654 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1986   -0.8272   -1.6976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9610   -0.0405   -0.2017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1055    0.9888    0.7083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1849    1.4606    1.1120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7524    1.4343    1.1208 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4674    0.8808    2.4825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9632   -3.3063   -2.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2250   -3.2354   -2.7764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8103   -3.7463   -1.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2596   -1.6509    0.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1677    1.1956    1.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3893    2.0048    0.3354 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3805    0.5132   -0.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5544   -1.4255   -0.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5726   -2.8149    0.8438 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8058   -2.4502   -0.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9363   -1.4406    1.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0657   -0.2085   -0.9465 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3723    0.6165   -2.7627 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3351    2.2404   -0.7911 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5926    1.2935    1.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2076    2.5767   -0.1190 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8343    3.1895    1.9134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4004    0.8635   -1.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4200    0.1055    1.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1224    2.4351   -0.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8181    1.5280   -0.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3403   -1.2322    0.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9453    0.0794   -2.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0180   -1.4178   -2.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6834    2.5318    1.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5679    1.3257    2.9446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3249    1.1954    3.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4732   -0.2261    2.5062 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  7 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  1  0
 26  2  1  0
 21  3  1  0
 30 24  1  0
 19 10  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  6 35  1  0
  8 36  1  0
  8 37  1  0
 10 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 15 43  1  0
 16 44  1  0
 17 45  1  0
 18 46  1  0
 19 47  1  0
 20 48  1  0
 21 49  1  6
 22 50  1  1
 23 51  1  0
 24 52  1  6
 25 53  1  1
 26 54  1  0
 26 55  1  0
 30 56  1  1
 31 57  1  0
 31 58  1  0
 31 59  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.640   4.910   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.028   4.241   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.370   2.740   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.410   1.536   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.870   1.536   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.910   2.740   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.253   4.241   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.349   5.031   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.509   4.018   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.904   2.602   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.022   0.251   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.463   0.661   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.532   2.199   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -5.488   6.565   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.640   6.450   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0       0.424   3.510   0.000  0.00  0.00           H+0
HETATM   17  O   UNK     0       1.667  -0.300   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.563  -1.191   0.000  0.00  0.00           C+0
HETATM   19  H   UNK     0      -2.269   0.049   0.000  0.00  0.00           H+0
HETATM   20  O   UNK     0      -4.078   0.149   0.000  0.00  0.00           O+0
HETATM   21  H   UNK     0      -5.140   1.407   0.000  0.00  0.00           H+0
HETATM   22  O   UNK     0      -9.483  -1.533   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -9.483  -3.073   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -8.149  -3.843   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -6.816  -3.073   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -6.816  -1.533   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -8.149  -0.763   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -8.149   0.777   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -5.482  -0.763   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0     -10.817  -3.843   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -8.149  -5.383   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -5.482  -3.843   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0     -10.817  -5.383   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -6.694   1.280   0.000  0.00  0.00           C+0
CONECT    1    2    7   15                                                  
CONECT    2    1    8    3                                                  
CONECT    3    4    2   10   21                                             
CONECT    4    3    5   20                                                  
CONECT    5    4   11    6   19                                             
CONECT    6    7    5   13   16                                             
CONECT    7    1    6                                                       
CONECT    8    2    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    3    9   34                                                  
CONECT   11    5   12   18                                                  
CONECT   12   11   13   17                                                  
CONECT   13    6   12                                                       
CONECT   14    8                                                            
CONECT   15    1                                                            
CONECT   16    6                                                            
CONECT   17   12                                                            
CONECT   18   11                                                            
CONECT   19    5                                                            
CONECT   20    4                                                            
CONECT   21    3                                                            
CONECT   22   23   27                                                       
CONECT   23   22   24   30                                                  
CONECT   24   23   25   31                                                  
CONECT   25   24   26   32                                                  
CONECT   26   25   27   29                                                  
CONECT   27   22   26   28                                                  
CONECT   28   27   34                                                       
CONECT   29   26                                                            
CONECT   30   23   33                                                       
CONECT   31   24                                                            
CONECT   32   25                                                            
CONECT   33   30                                                            
CONECT   34   10   28                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

COMPND    HMDB0302055
HETATM    1  C1  UNL     1      -2.967  -3.048  -1.971  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.954  -1.645  -1.511  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.836  -1.220  -0.947  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.665  -2.066  -0.773  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.521  -3.249  -1.176  1.00  0.00           O  
HETATM    6  C5  UNL     1       0.305  -1.245  -0.030  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.175  -0.048   0.227  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.467   1.073   0.948  1.00  0.00           C  
HETATM    9  O2  UNL     1       1.730   0.854   1.410  1.00  0.00           O  
HETATM   10  C8  UNL     1       2.717   0.601   0.496  1.00  0.00           C  
HETATM   11  O3  UNL     1       3.486  -0.464   0.891  1.00  0.00           O  
HETATM   12  C9  UNL     1       4.236  -0.961  -0.191  1.00  0.00           C  
HETATM   13  C10 UNL     1       5.181  -2.014   0.401  1.00  0.00           C  
HETATM   14  O4  UNL     1       5.997  -1.404   1.350  1.00  0.00           O  
HETATM   15  C11 UNL     1       4.995   0.140  -0.864  1.00  0.00           C  
HETATM   16  O5  UNL     1       4.589   0.331  -2.201  1.00  0.00           O  
HETATM   17  C12 UNL     1       5.016   1.423  -0.095  1.00  0.00           C  
HETATM   18  O6  UNL     1       6.001   1.389   0.913  1.00  0.00           O  
HETATM   19  C13 UNL     1       3.698   1.804   0.491  1.00  0.00           C  
HETATM   20  O7  UNL     1       3.880   2.205   1.814  1.00  0.00           O  
HETATM   21  C14 UNL     1      -1.531   0.094  -0.404  1.00  0.00           C  
HETATM   22  C15 UNL     1      -2.483   0.649   0.592  1.00  0.00           C  
HETATM   23  O8  UNL     1      -2.044   1.975   0.862  1.00  0.00           O  
HETATM   24  C16 UNL     1      -3.879   0.828   0.044  1.00  0.00           C  
HETATM   25  C17 UNL     1      -4.600  -0.438  -0.265  1.00  0.00           C  
HETATM   26  C18 UNL     1      -4.199  -0.827  -1.698  1.00  0.00           C  
HETATM   27  O9  UNL     1      -5.961  -0.041  -0.202  1.00  0.00           O  
HETATM   28  C19 UNL     1      -6.105   0.989   0.708  1.00  0.00           C  
HETATM   29  O10 UNL     1      -7.185   1.461   1.112  1.00  0.00           O  
HETATM   30  C20 UNL     1      -4.752   1.434   1.121  1.00  0.00           C  
HETATM   31  C21 UNL     1      -4.467   0.881   2.483  1.00  0.00           C  
HETATM   32  H1  UNL     1      -3.963  -3.306  -2.380  1.00  0.00           H  
HETATM   33  H2  UNL     1      -2.225  -3.235  -2.776  1.00  0.00           H  
HETATM   34  H3  UNL     1      -2.810  -3.746  -1.106  1.00  0.00           H  
HETATM   35  H4  UNL     1       1.260  -1.651   0.235  1.00  0.00           H  
HETATM   36  H5  UNL     1      -0.168   1.196   1.889  1.00  0.00           H  
HETATM   37  H6  UNL     1       0.389   2.005   0.335  1.00  0.00           H  
HETATM   38  H7  UNL     1       2.381   0.513  -0.552  1.00  0.00           H  
HETATM   39  H8  UNL     1       3.554  -1.426  -0.926  1.00  0.00           H  
HETATM   40  H9  UNL     1       4.573  -2.815   0.844  1.00  0.00           H  
HETATM   41  H10 UNL     1       5.806  -2.450  -0.417  1.00  0.00           H  
HETATM   42  H11 UNL     1       6.936  -1.441   1.033  1.00  0.00           H  
HETATM   43  H12 UNL     1       6.066  -0.209  -0.946  1.00  0.00           H  
HETATM   44  H13 UNL     1       5.372   0.617  -2.763  1.00  0.00           H  
HETATM   45  H14 UNL     1       5.335   2.240  -0.791  1.00  0.00           H  
HETATM   46  H15 UNL     1       5.593   1.294   1.812  1.00  0.00           H  
HETATM   47  H16 UNL     1       3.208   2.577  -0.119  1.00  0.00           H  
HETATM   48  H17 UNL     1       3.834   3.190   1.913  1.00  0.00           H  
HETATM   49  H18 UNL     1      -1.400   0.863  -1.219  1.00  0.00           H  
HETATM   50  H19 UNL     1      -2.420   0.105   1.531  1.00  0.00           H  
HETATM   51  H20 UNL     1      -2.122   2.435  -0.021  1.00  0.00           H  
HETATM   52  H21 UNL     1      -3.818   1.528  -0.809  1.00  0.00           H  
HETATM   53  H22 UNL     1      -4.340  -1.232   0.434  1.00  0.00           H  
HETATM   54  H23 UNL     1      -3.945   0.079  -2.286  1.00  0.00           H  
HETATM   55  H24 UNL     1      -5.018  -1.418  -2.108  1.00  0.00           H  
HETATM   56  H25 UNL     1      -4.683   2.532   1.164  1.00  0.00           H  
HETATM   57  H26 UNL     1      -3.568   1.326   2.945  1.00  0.00           H  
HETATM   58  H27 UNL     1      -5.325   1.195   3.143  1.00  0.00           H  
HETATM   59  H28 UNL     1      -4.473  -0.226   2.506  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3    3   26
CONECT    3    4   21
CONECT    4    5    5    6
CONECT    6    7    7   35
CONECT    7    8   21
CONECT    8    9   36   37
CONECT    9   10
CONECT   10   11   19   38
CONECT   11   12
CONECT   12   13   15   39
CONECT   13   14   40   41
CONECT   14   42
CONECT   15   16   17   43
CONECT   16   44
CONECT   17   18   19   45
CONECT   18   46
CONECT   19   20   47
CONECT   20   48
CONECT   21   22   49
CONECT   22   23   24   50
CONECT   23   51
CONECT   24   25   30   52
CONECT   25   26   27   53
CONECT   26   54   55
CONECT   27   28
CONECT   28   29   29   30
CONECT   30   31   56
CONECT   31   57   58   59
END

HMDB0302055
     RDKit          3D
Cichorioside I
 59 62  0  0  0  0  0  0  0  0999 V2000
   -2.9675   -3.0478   -1.9706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9538   -1.6449   -1.5105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8360   -1.2197   -0.9468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6648   -2.0662   -0.7728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5207   -3.2492   -1.1757 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3050   -1.2446   -0.0301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1746   -0.0479    0.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4675    1.0725    0.9484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7305    0.8539    1.4095 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7166    0.6012    0.4955 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4862   -0.4641    0.8912 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355   -0.9609   -0.1908 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1807   -2.0141    0.4006 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9972   -1.4037    1.3496 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9954    0.1398   -0.8643 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5891    0.3305   -2.2005 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0161    1.4226   -0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0007    1.3891    0.9129 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6980    1.8039    0.4913 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8800    2.2046    1.8144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5310    0.0943   -0.4035 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4825    0.6493    0.5923 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0443    1.9747    0.8622 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8793    0.8282    0.0441 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6003   -0.4384   -0.2654 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1986   -0.8272   -1.6976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9610   -0.0405   -0.2017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1055    0.9888    0.7083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1849    1.4606    1.1120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7524    1.4343    1.1208 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4674    0.8808    2.4825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9632   -3.3063   -2.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2250   -3.2354   -2.7764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8103   -3.7463   -1.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2596   -1.6509    0.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1677    1.1956    1.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3893    2.0048    0.3354 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3805    0.5132   -0.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5544   -1.4255   -0.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5726   -2.8149    0.8438 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8058   -2.4502   -0.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9363   -1.4406    1.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0657   -0.2085   -0.9465 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3723    0.6165   -2.7627 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3351    2.2404   -0.7911 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5926    1.2935    1.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2076    2.5767   -0.1190 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8343    3.1895    1.9134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4004    0.8635   -1.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4200    0.1055    1.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1224    2.4351   -0.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8181    1.5280   -0.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3403   -1.2322    0.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9453    0.0794   -2.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0180   -1.4178   -2.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6834    2.5318    1.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5679    1.3257    2.9446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3249    1.1954    3.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4732   -0.2261    2.5062 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  7 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  1  0
 26  2  1  0
 21  3  1  0
 30 24  1  0
 19 10  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  6 35  1  0
  8 36  1  0
  8 37  1  0
 10 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 15 43  1  0
 16 44  1  0
 17 45  1  0
 18 46  1  0
 19 47  1  0
 20 48  1  0
 21 49  1  6
 22 50  1  1
 23 51  1  0
 24 52  1  6
 25 53  1  1
 26 54  1  0
 26 55  1  0
 30 56  1  1
 31 57  1  0
 31 58  1  0
 31 59  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₁H₂₈O₁₀

Average Molecular Weight

440.441

Monoisotopic Molecular Weight

440.168247116

IUPAC Name

(3S,3aS,4R,4aS,9aS)-4-hydroxy-3,8-dimethyl-5-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2H,3H,3aH,4H,4aH,7H,9H,9aH-azuleno[6,5-b]furan-2,7-dione

Traditional Name

(3S,3aS,4R,4aS,9aS)-4-hydroxy-3,8-dimethyl-5-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3H,3aH,4H,4aH,9H,9aH-azuleno[6,5-b]furan-2,7-dione

CAS Registry Number

Not Available

SMILES

[H][C@]12CC(C)=C3C(=O)C=C(COC4OC(CO)C(O)C(O)C4O)[C@]3([H])[C@@H](O)[C@]1([H])[C@H](C)C(=O)O2

InChI Identifier

InChI=1S/C21H28O10/c1-7-3-11-14(8(2)20(28)30-11)17(25)15-9(4-10(23)13(7)15)6-29-21-19(27)18(26)16(24)12(5-22)31-21/h4,8,11-12,14-19,21-22,24-27H,3,5-6H2,1-2H3/t8-,11-,12?,14+,15-,16?,17-,18?,19?,21?/m0/s1

InChI Key

POOPERNNBMZLBU-YFVSWLSASA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0302055)

Food

Vegetable

Leaf vegetable

Endive (FooDB: FOOD00048)

Process

Not Available

Role

Not Available

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-0.96	ALOGPS
logP	-1.9	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	12.18	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	162.98 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	104.48 m³·mol⁻¹	ChemAxon
Polarizability	44.06 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	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	201.66	32859911
AllCCS	[M+H-H2O]+	199.586	32859911
AllCCS	[M+Na]+	204.098	32859911
AllCCS	[M+NH4]+	203.557	32859911
AllCCS	[M-H]-	198.668	32859911
AllCCS	[M+Na-2H]-	199.104	32859911
AllCCS	[M+HCOO]-	199.731	32859911
DeepCCS	[M-2H]-	233.737	30932474
DeepCCS	[M+Na]+	209.249	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cichorioside I 10V, Positive-QTOF	splash10-01vo-0161900000-e3bf8faea4f71a9b467f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cichorioside I 20V, Positive-QTOF	splash10-03di-0591200000-7eac3948eba8468f0955	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cichorioside I 40V, Positive-QTOF	splash10-03dl-4982100000-1b7d54e556dcc57aeaf0	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cichorioside I 10V, Negative-QTOF	splash10-000i-1233900000-a91118325b91e148dfc3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cichorioside I 20V, Negative-QTOF	splash10-076r-4943500000-3be2edd28134666e67ee	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cichorioside I 40V, Negative-QTOF	splash10-0203-9470000000-d396724bd706dbabf906	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cichorioside I 10V, Positive-QTOF	splash10-0006-0010900000-a13ab6425e9509aa04fb	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cichorioside I 20V, Positive-QTOF	splash10-02kc-0469800000-5820d5a8c34a7c9c8a93	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cichorioside I 40V, Positive-QTOF	splash10-03dl-3296000000-ae0722955307d4f34d1d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cichorioside I 10V, Negative-QTOF	splash10-000i-0000900000-59322d265919df5c7bf4	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cichorioside I 20V, Negative-QTOF	splash10-05w0-9086700000-8f4626f0f9eb5df92677	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cichorioside I 40V, Negative-QTOF	splash10-0a4l-9161300000-fc015083edddbecfd520	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB001801

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Cichorioside I (HMDB0302055)

MOL for HMDB0302055 (Cichorioside I)

3D MOL for HMDB0302055 (Cichorioside I)

3D SDF for HMDB0302055 (Cichorioside I)

3D-SDF for HMDB0302055 (Cichorioside I)

PDB for HMDB0302055 (Cichorioside I)

3D PDB for HMDB0302055 (Cichorioside I)

SMILES for HMDB0302055 (Cichorioside I)

INCHI for HMDB0302055 (Cichorioside I)

Structure for HMDB0302055 (Cichorioside I)

3D Structure for HMDB0302055 (Cichorioside I)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra