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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:32:44 UTC

Update Date

2022-03-07 02:54:54 UTC

HMDB ID

HMDB0036408

Secondary Accession Numbers

HMDB36408

Metabolite Identification

Common Name

Franguloside

Description

Franguloside belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone. Franguloside has been detected, but not quantified in, green vegetables. This could make franguloside a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Franguloside.

Structure

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


  Mrv0541 05061309072D          

 30 33  0  0  0  0            999 V2000
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  7  3  2  0  0  0  0
  7  4  1  0  0  0  0
  8  2  1  0  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  3  1  0  0  0  0
 11  5  1  0  0  0  0
 12  4  2  0  0  0  0
 13  6  2  0  0  0  0
 14 10  2  0  0  0  0
 14 12  1  0  0  0  0
 15 11  2  0  0  0  0
 15 13  1  0  0  0  0
 16  8  1  0  0  0  0
 17 10  1  0  0  0  0
 17 11  1  0  0  0  0
 18 14  1  0  0  0  0
 18 15  1  0  0  0  0
 19 16  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 12  1  0  0  0  0
 23 13  1  0  0  0  0
 24 16  1  0  0  0  0
 25 17  2  0  0  0  0
 26 18  2  0  0  0  0
 27 19  1  0  0  0  0
 28 20  1  0  0  0  0
 29  8  1  0  0  0  0
 29 21  1  0  0  0  0
 30  9  1  0  0  0  0
 30 21  1  0  0  0  0
M  END

HMDB0036408
     RDKit          3D
Franguloside
 50 53  0  0  0  0  0  0  0  0999 V2000
    6.9183    2.3768    1.6103 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9953    1.3940    0.9631 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4769    0.3147    0.2766 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6142   -0.6167   -0.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1547   -1.6692   -1.0050 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2390   -0.3980   -0.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7958    0.6992    0.4806 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6550    1.6208    1.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3554    0.8896    0.5798 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8843    1.8893    1.2152 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3824   -0.0163   -0.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0204    0.2374    0.1224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9136   -0.6018   -0.4326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2476   -0.2932   -0.2557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3436   -1.0141   -0.7372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1080   -0.1585   -1.5168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1460    0.4358   -0.8651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4754    1.7221   -1.6386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8941    0.8296    0.5432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1898    2.0434    0.6623 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2343   -0.2299    1.3756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8671   -0.4924    2.5642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1329   -1.4805    0.4942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3109   -2.3818    1.1583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4544   -1.6818   -1.1200 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9246   -1.9665   -1.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2856   -3.0567   -1.9763 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8621   -1.1135   -0.7169 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2957   -1.3374   -0.8377 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7057   -2.3365   -1.4739 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8463    2.4810    1.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4094    3.3423    1.7832 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1634    1.9629    2.6171 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5402    0.1348    0.1780 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8491   -2.4331   -1.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2617    2.4590    1.6202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3097    1.1156    0.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1169   -1.9109   -1.3105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0966   -0.1711   -0.9003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4764    2.0871   -1.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3327    1.5441   -2.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7137    2.5062   -1.3531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8959    1.0378    1.0193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8140    2.8181    0.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1822    0.0910    1.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6134   -1.1246    2.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1072   -1.8881    0.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6272   -1.8492    1.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1524   -2.3623   -1.5691 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1210   -3.4484   -2.2148 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  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 13 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 29 30  2  0
  8  2  1  0
 28 11  1  0
 29  6  1  0
 23 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  5 35  1  0
  8 36  1  0
 12 37  1  0
 15 38  1  0
 17 39  1  0
 18 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
 21 45  1  0
 22 46  1  0
 23 47  1  0
 24 48  1  0
 25 49  1  0
 27 50  1  0
M  END


  Mrv0541 05061309072D          

 30 33  0  0  0  0            999 V2000
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  7  3  2  0  0  0  0
  7  4  1  0  0  0  0
  8  2  1  0  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  3  1  0  0  0  0
 11  5  1  0  0  0  0
 12  4  2  0  0  0  0
 13  6  2  0  0  0  0
 14 10  2  0  0  0  0
 14 12  1  0  0  0  0
 15 11  2  0  0  0  0
 15 13  1  0  0  0  0
 16  8  1  0  0  0  0
 17 10  1  0  0  0  0
 17 11  1  0  0  0  0
 18 14  1  0  0  0  0
 18 15  1  0  0  0  0
 19 16  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 12  1  0  0  0  0
 23 13  1  0  0  0  0
 24 16  1  0  0  0  0
 25 17  2  0  0  0  0
 26 18  2  0  0  0  0
 27 19  1  0  0  0  0
 28 20  1  0  0  0  0
 29  8  1  0  0  0  0
 29 21  1  0  0  0  0
 30  9  1  0  0  0  0
 30 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036408

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1OC(OC2=CC3=C(C(O)=C2)C(=O)C2=C(C=C(C)C=C2O)C3=O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O9/c1-7-3-10-14(12(22)4-7)18(26)15-11(17(10)25)5-9(6-13(15)23)30-21-20(28)19(27)16(24)8(2)29-21/h3-6,8,16,19-24,27-28H,1-2H3

> <INCHI_KEY>
DTTVUKLWJFJOHO-UHFFFAOYSA-N

> <FORMULA>
C21H20O9

> <MOLECULAR_WEIGHT>
416.3781

> <EXACT_MASS>
416.110732238

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
41.37933294299171

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,8-dihydroxy-3-methyl-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
1.33

> <JCHEM_LOGP>
2.6002733723333327

> <ALOGPS_LOGS>
-2.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.740107146039719

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.06105166717744

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6122003586638183

> <JCHEM_POLAR_SURFACE_AREA>
153.74999999999997

> <JCHEM_REFRACTIVITY>
102.73559999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.80e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,8-dihydroxy-3-methyl-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]anthracene-9,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036408
     RDKit          3D
Franguloside
 50 53  0  0  0  0  0  0  0  0999 V2000
    6.9183    2.3768    1.6103 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9953    1.3940    0.9631 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4769    0.3147    0.2766 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6142   -0.6167   -0.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1547   -1.6692   -1.0050 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2390   -0.3980   -0.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7958    0.6992    0.4806 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6550    1.6208    1.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3554    0.8896    0.5798 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8843    1.8893    1.2152 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3824   -0.0163   -0.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0204    0.2374    0.1224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9136   -0.6018   -0.4326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2476   -0.2932   -0.2557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3436   -1.0141   -0.7372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1080   -0.1585   -1.5168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1460    0.4358   -0.8651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4754    1.7221   -1.6386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8941    0.8296    0.5432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1898    2.0434    0.6623 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2343   -0.2299    1.3756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8671   -0.4924    2.5642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1329   -1.4805    0.4942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3109   -2.3818    1.1583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4544   -1.6818   -1.1200 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9246   -1.9665   -1.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2856   -3.0567   -1.9763 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8621   -1.1135   -0.7169 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2957   -1.3374   -0.8377 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7057   -2.3365   -1.4739 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8463    2.4810    1.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4094    3.3423    1.7832 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1634    1.9629    2.6171 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5402    0.1348    0.1780 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8491   -2.4331   -1.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2617    2.4590    1.6202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3097    1.1156    0.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1169   -1.9109   -1.3105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0966   -0.1711   -0.9003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4764    2.0871   -1.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3327    1.5441   -2.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7137    2.5062   -1.3531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8959    1.0378    1.0193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8140    2.8181    0.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1822    0.0910    1.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6134   -1.1246    2.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1072   -1.8881    0.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6272   -1.8492    1.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1524   -2.3623   -1.5691 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1210   -3.4484   -2.2148 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  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 13 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 29 30  2  0
  8  2  1  0
 28 11  1  0
 29  6  1  0
 23 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  5 35  1  0
  8 36  1  0
 12 37  1  0
 15 38  1  0
 17 39  1  0
 18 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
 21 45  1  0
 22 46  1  0
 23 47  1  0
 24 48  1  0
 25 49  1  0
 27 50  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      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3    7   10                                                       
CONECT    4    7   12                                                       
CONECT    5    9   11                                                       
CONECT    6    9   13                                                       
CONECT    7    1    3    4                                                  
CONECT    8    2   16   29                                                  
CONECT    9    5    6   30                                                  
CONECT   10    3   14   17                                                  
CONECT   11    5   15   17                                                  
CONECT   12    4   14   22                                                  
CONECT   13    6   15   23                                                  
CONECT   14   10   12   18                                                  
CONECT   15   11   13   18                                                  
CONECT   16    8   19   24                                                  
CONECT   17   10   11   25                                                  
CONECT   18   14   15   26                                                  
CONECT   19   16   20   27                                                  
CONECT   20   19   21   28                                                  
CONECT   21   20   29   30                                                  
CONECT   22   12                                                            
CONECT   23   13                                                            
CONECT   24   16                                                            
CONECT   25   17                                                            
CONECT   26   18                                                            
CONECT   27   19                                                            
CONECT   28   20                                                            
CONECT   29    8   21                                                       
CONECT   30    9   21                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

COMPND    HMDB0036408
HETATM    1  C1  UNL     1       6.918   2.377   1.610  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.995   1.394   0.963  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.477   0.315   0.277  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.614  -0.617  -0.337  1.00  0.00           C  
HETATM    5  O1  UNL     1       6.155  -1.669  -1.005  1.00  0.00           O  
HETATM    6  C5  UNL     1       4.239  -0.398  -0.218  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.796   0.699   0.481  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.655   1.621   1.087  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.355   0.890   0.580  1.00  0.00           C  
HETATM   10  O2  UNL     1       1.884   1.889   1.215  1.00  0.00           O  
HETATM   11  C9  UNL     1       1.382  -0.016  -0.019  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.020   0.237   0.122  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.914  -0.602  -0.433  1.00  0.00           C  
HETATM   14  O3  UNL     1      -2.248  -0.293  -0.256  1.00  0.00           O  
HETATM   15  C12 UNL     1      -3.344  -1.014  -0.737  1.00  0.00           C  
HETATM   16  O4  UNL     1      -4.108  -0.158  -1.517  1.00  0.00           O  
HETATM   17  C13 UNL     1      -5.146   0.436  -0.865  1.00  0.00           C  
HETATM   18  C14 UNL     1      -5.475   1.722  -1.639  1.00  0.00           C  
HETATM   19  C15 UNL     1      -4.894   0.830   0.543  1.00  0.00           C  
HETATM   20  O5  UNL     1      -4.190   2.043   0.662  1.00  0.00           O  
HETATM   21  C16 UNL     1      -4.234  -0.230   1.376  1.00  0.00           C  
HETATM   22  O6  UNL     1      -4.867  -0.492   2.564  1.00  0.00           O  
HETATM   23  C17 UNL     1      -4.133  -1.481   0.494  1.00  0.00           C  
HETATM   24  O7  UNL     1      -3.311  -2.382   1.158  1.00  0.00           O  
HETATM   25  C18 UNL     1      -0.454  -1.682  -1.120  1.00  0.00           C  
HETATM   26  C19 UNL     1       0.925  -1.967  -1.281  1.00  0.00           C  
HETATM   27  O8  UNL     1       1.286  -3.057  -1.976  1.00  0.00           O  
HETATM   28  C20 UNL     1       1.862  -1.114  -0.717  1.00  0.00           C  
HETATM   29  C21 UNL     1       3.296  -1.337  -0.838  1.00  0.00           C  
HETATM   30  O9  UNL     1       3.706  -2.337  -1.474  1.00  0.00           O  
HETATM   31  H1  UNL     1       7.846   2.481   1.012  1.00  0.00           H  
HETATM   32  H2  UNL     1       6.409   3.342   1.783  1.00  0.00           H  
HETATM   33  H3  UNL     1       7.163   1.963   2.617  1.00  0.00           H  
HETATM   34  H4  UNL     1       7.540   0.135   0.178  1.00  0.00           H  
HETATM   35  H5  UNL     1       5.849  -2.433  -1.501  1.00  0.00           H  
HETATM   36  H6  UNL     1       4.262   2.459   1.620  1.00  0.00           H  
HETATM   37  H7  UNL     1      -0.310   1.116   0.682  1.00  0.00           H  
HETATM   38  H8  UNL     1      -3.117  -1.911  -1.310  1.00  0.00           H  
HETATM   39  H9  UNL     1      -6.097  -0.171  -0.900  1.00  0.00           H  
HETATM   40  H10 UNL     1      -6.476   2.087  -1.371  1.00  0.00           H  
HETATM   41  H11 UNL     1      -5.333   1.544  -2.717  1.00  0.00           H  
HETATM   42  H12 UNL     1      -4.714   2.506  -1.353  1.00  0.00           H  
HETATM   43  H13 UNL     1      -5.896   1.038   1.019  1.00  0.00           H  
HETATM   44  H14 UNL     1      -4.814   2.818   0.750  1.00  0.00           H  
HETATM   45  H15 UNL     1      -3.182   0.091   1.554  1.00  0.00           H  
HETATM   46  H16 UNL     1      -5.613  -1.125   2.378  1.00  0.00           H  
HETATM   47  H17 UNL     1      -5.107  -1.888   0.234  1.00  0.00           H  
HETATM   48  H18 UNL     1      -2.627  -1.849   1.650  1.00  0.00           H  
HETATM   49  H19 UNL     1      -1.152  -2.362  -1.569  1.00  0.00           H  
HETATM   50  H20 UNL     1       2.121  -3.448  -2.215  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3    3    8
CONECT    3    4   34
CONECT    4    5    6    6
CONECT    5   35
CONECT    6    7   29
CONECT    7    8    8    9
CONECT    8   36
CONECT    9   10   10   11
CONECT   11   12   12   28
CONECT   12   13   37
CONECT   13   14   25   25
CONECT   14   15
CONECT   15   16   23   38
CONECT   16   17
CONECT   17   18   19   39
CONECT   18   40   41   42
CONECT   19   20   21   43
CONECT   20   44
CONECT   21   22   23   45
CONECT   22   46
CONECT   23   24   47
CONECT   24   48
CONECT   25   26   49
CONECT   26   27   28   28
CONECT   27   50
CONECT   28   29
CONECT   29   30   30
END

HMDB0036408
     RDKit          3D
Franguloside
 50 53  0  0  0  0  0  0  0  0999 V2000
    6.9183    2.3768    1.6103 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9953    1.3940    0.9631 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4769    0.3147    0.2766 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6142   -0.6167   -0.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1547   -1.6692   -1.0050 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2390   -0.3980   -0.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7958    0.6992    0.4806 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6550    1.6208    1.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3554    0.8896    0.5798 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8843    1.8893    1.2152 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3824   -0.0163   -0.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0204    0.2374    0.1224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9136   -0.6018   -0.4326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2476   -0.2932   -0.2557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3436   -1.0141   -0.7372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1080   -0.1585   -1.5168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1460    0.4358   -0.8651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4754    1.7221   -1.6386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8941    0.8296    0.5432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1898    2.0434    0.6623 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2343   -0.2299    1.3756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8671   -0.4924    2.5642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1329   -1.4805    0.4942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3109   -2.3818    1.1583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4544   -1.6818   -1.1200 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9246   -1.9665   -1.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2856   -3.0567   -1.9763 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8621   -1.1135   -0.7169 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2957   -1.3374   -0.8377 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7057   -2.3365   -1.4739 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8463    2.4810    1.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4094    3.3423    1.7832 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1634    1.9629    2.6171 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5402    0.1348    0.1780 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8491   -2.4331   -1.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2617    2.4590    1.6202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3097    1.1156    0.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1169   -1.9109   -1.3105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0966   -0.1711   -0.9003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4764    2.0871   -1.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3327    1.5441   -2.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7137    2.5062   -1.3531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8959    1.0378    1.0193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8140    2.8181    0.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1822    0.0910    1.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6134   -1.1246    2.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1072   -1.8881    0.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6272   -1.8492    1.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1524   -2.3623   -1.5691 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1210   -3.4484   -2.2148 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  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 13 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 29 30  2  0
  8  2  1  0
 28 11  1  0
 29  6  1  0
 23 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  5 35  1  0
  8 36  1  0
 12 37  1  0
 15 38  1  0
 17 39  1  0
 18 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
 21 45  1  0
 22 46  1  0
 23 47  1  0
 24 48  1  0
 25 49  1  0
 27 50  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Frangulin a	HMDB
Frangulin a (8ci)	HMDB

Chemical Formula

C₂₁H₂₀O₉

Average Molecular Weight

416.3781

Monoisotopic Molecular Weight

416.110732238

IUPAC Name

1,8-dihydroxy-3-methyl-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-9,10-dihydroanthracene-9,10-dione

Traditional Name

1,8-dihydroxy-3-methyl-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]anthracene-9,10-dione

CAS Registry Number

521-62-0

SMILES

CC1OC(OC2=CC3=C(C(O)=C2)C(=O)C2=C(C=C(C)C=C2O)C3=O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C21H20O9/c1-7-3-10-14(12(22)4-7)18(26)15-11(17(10)25)5-9(6-13(15)23)30-21-20(28)19(27)16(24)8(2)29-21/h3-6,8,16,19-24,27-28H,1-2H3

InChI Key

DTTVUKLWJFJOHO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

9,10-anthraquinone
Anthraquinone
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monosaccharide
Oxane
Vinylogous acid
Ketone
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0036408)
Cytoplasm (HMDB: HMDB0036408)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036408)

Source

Exogenous

Food

Food (HMDB: HMDB0036408)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Endogenous

Plant

Plant (HMDB: HMDB0036408)

Not Available

Nutrient (HMDB: HMDB0036408)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	228 °C	Not Available
Boiling Point	744.30 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	6.44 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	4.340 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.8 g/L	ALOGPS
logP	1.33	ALOGPS
logP	2.6	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	9.06	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	153.75 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	102.74 m³·mol⁻¹	ChemAxon
Polarizability	41.38 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	197.973	31661259
DarkChem	[M-H]-	193.953	31661259
DeepCCS	[M+H]+	195.775	30932474
DeepCCS	[M-H]-	193.38	30932474
DeepCCS	[M-2H]-	226.482	30932474
DeepCCS	[M+Na]+	201.69	30932474
AllCCS	[M+H]+	197.2	32859911
AllCCS	[M+H-H2O]+	194.7	32859911
AllCCS	[M+NH4]+	199.5	32859911
AllCCS	[M+Na]+	200.2	32859911
AllCCS	[M-H]-	195.3	32859911
AllCCS	[M+Na-2H]-	195.4	32859911
AllCCS	[M+HCOO]-	195.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Franguloside	CC1OC(OC2=CC3=C(C(O)=C2)C(=O)C2=C(C=C(C)C=C2O)C3=O)C(O)C(O)C1O	4736.6	Standard polar	33892256
Franguloside	CC1OC(OC2=CC3=C(C(O)=C2)C(=O)C2=C(C=C(C)C=C2O)C3=O)C(O)C(O)C1O	3491.0	Standard non polar	33892256
Franguloside	CC1OC(OC2=CC3=C(C(O)=C2)C(=O)C2=C(C=C(C)C=C2O)C3=O)C(O)C(O)C1O	3836.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Franguloside,1TMS,isomer #1	CC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C)C=C(OC4OC(C)C(O)C(O)C4O)C=C3C(=O)C2=C1	3666.3	Semi standard non polar	33892256
Franguloside,1TMS,isomer #2	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(O)C=C(OC4OC(C)C(O)C(O)C4O)C=C3C(=O)C2=C1	3667.8	Semi standard non polar	33892256
Franguloside,1TMS,isomer #3	CC1=CC(O)=C2C(=O)C3=C(O)C=C(OC4OC(C)C(O)C(O)C4O[Si](C)(C)C)C=C3C(=O)C2=C1	3575.8	Semi standard non polar	33892256
Franguloside,1TMS,isomer #4	CC1=CC(O)=C2C(=O)C3=C(O)C=C(OC4OC(C)C(O)C(O[Si](C)(C)C)C4O)C=C3C(=O)C2=C1	3628.1	Semi standard non polar	33892256
Franguloside,1TMS,isomer #5	CC1=CC(O)=C2C(=O)C3=C(O)C=C(OC4OC(C)C(O[Si](C)(C)C)C(O)C4O)C=C3C(=O)C2=C1	3638.0	Semi standard non polar	33892256
Franguloside,2TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(O[Si](C)(C)C)C=C(OC4OC(C)C(O)C(O)C4O)C=C3C(=O)C2=C1	3616.0	Semi standard non polar	33892256
Franguloside,2TMS,isomer #10	CC1=CC(O)=C2C(=O)C3=C(O)C=C(OC4OC(C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C4O)C=C3C(=O)C2=C1	3541.5	Semi standard non polar	33892256
Franguloside,2TMS,isomer #2	CC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C)C=C(OC4OC(C)C(O[Si](C)(C)C)C(O)C4O)C=C3C(=O)C2=C1	3558.8	Semi standard non polar	33892256
Franguloside,2TMS,isomer #3	CC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C)C=C(OC4OC(C)C(O)C(O[Si](C)(C)C)C4O)C=C3C(=O)C2=C1	3544.7	Semi standard non polar	33892256
Franguloside,2TMS,isomer #4	CC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C)C=C(OC4OC(C)C(O)C(O)C4O[Si](C)(C)C)C=C3C(=O)C2=C1	3506.8	Semi standard non polar	33892256
Franguloside,2TMS,isomer #5	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(O)C=C(OC4OC(C)C(O[Si](C)(C)C)C(O)C4O)C=C3C(=O)C2=C1	3564.7	Semi standard non polar	33892256
Franguloside,2TMS,isomer #6	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(O)C=C(OC4OC(C)C(O)C(O[Si](C)(C)C)C4O)C=C3C(=O)C2=C1	3544.9	Semi standard non polar	33892256
Franguloside,2TMS,isomer #7	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(O)C=C(OC4OC(C)C(O)C(O)C4O[Si](C)(C)C)C=C3C(=O)C2=C1	3508.2	Semi standard non polar	33892256
Franguloside,2TMS,isomer #8	CC1=CC(O)=C2C(=O)C3=C(O)C=C(OC4OC(C)C(O[Si](C)(C)C)C(O)C4O[Si](C)(C)C)C=C3C(=O)C2=C1	3529.0	Semi standard non polar	33892256
Franguloside,2TMS,isomer #9	CC1=CC(O)=C2C(=O)C3=C(O)C=C(OC4OC(C)C(O)C(O[Si](C)(C)C)C4O[Si](C)(C)C)C=C3C(=O)C2=C1	3529.6	Semi standard non polar	33892256
Franguloside,3TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(O[Si](C)(C)C)C=C(OC4OC(C)C(O[Si](C)(C)C)C(O)C4O)C=C3C(=O)C2=C1	3541.6	Semi standard non polar	33892256
Franguloside,3TMS,isomer #10	CC1=CC(O)=C2C(=O)C3=C(O)C=C(OC4OC(C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C4O[Si](C)(C)C)C=C3C(=O)C2=C1	3482.2	Semi standard non polar	33892256
Franguloside,3TMS,isomer #2	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(O[Si](C)(C)C)C=C(OC4OC(C)C(O)C(O[Si](C)(C)C)C4O)C=C3C(=O)C2=C1	3508.3	Semi standard non polar	33892256
Franguloside,3TMS,isomer #3	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(O[Si](C)(C)C)C=C(OC4OC(C)C(O)C(O)C4O[Si](C)(C)C)C=C3C(=O)C2=C1	3496.7	Semi standard non polar	33892256
Franguloside,3TMS,isomer #4	CC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C)C=C(OC4OC(C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C4O)C=C3C(=O)C2=C1	3486.1	Semi standard non polar	33892256
Franguloside,3TMS,isomer #5	CC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C)C=C(OC4OC(C)C(O[Si](C)(C)C)C(O)C4O[Si](C)(C)C)C=C3C(=O)C2=C1	3487.1	Semi standard non polar	33892256
Franguloside,3TMS,isomer #6	CC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C)C=C(OC4OC(C)C(O)C(O[Si](C)(C)C)C4O[Si](C)(C)C)C=C3C(=O)C2=C1	3470.4	Semi standard non polar	33892256
Franguloside,3TMS,isomer #7	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(O)C=C(OC4OC(C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C4O)C=C3C(=O)C2=C1	3494.4	Semi standard non polar	33892256
Franguloside,3TMS,isomer #8	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(O)C=C(OC4OC(C)C(O[Si](C)(C)C)C(O)C4O[Si](C)(C)C)C=C3C(=O)C2=C1	3489.6	Semi standard non polar	33892256
Franguloside,3TMS,isomer #9	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(O)C=C(OC4OC(C)C(O)C(O[Si](C)(C)C)C4O[Si](C)(C)C)C=C3C(=O)C2=C1	3477.6	Semi standard non polar	33892256
Franguloside,4TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(O[Si](C)(C)C)C=C(OC4OC(C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C4O)C=C3C(=O)C2=C1	3473.2	Semi standard non polar	33892256
Franguloside,4TMS,isomer #2	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(O[Si](C)(C)C)C=C(OC4OC(C)C(O[Si](C)(C)C)C(O)C4O[Si](C)(C)C)C=C3C(=O)C2=C1	3463.9	Semi standard non polar	33892256
Franguloside,4TMS,isomer #3	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(O[Si](C)(C)C)C=C(OC4OC(C)C(O)C(O[Si](C)(C)C)C4O[Si](C)(C)C)C=C3C(=O)C2=C1	3459.7	Semi standard non polar	33892256
Franguloside,4TMS,isomer #4	CC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C)C=C(OC4OC(C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C4O[Si](C)(C)C)C=C3C(=O)C2=C1	3445.8	Semi standard non polar	33892256
Franguloside,4TMS,isomer #5	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(O)C=C(OC4OC(C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C4O[Si](C)(C)C)C=C3C(=O)C2=C1	3458.0	Semi standard non polar	33892256
Franguloside,5TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(O[Si](C)(C)C)C=C(OC4OC(C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C4O[Si](C)(C)C)C=C3C(=O)C2=C1	3462.2	Semi standard non polar	33892256
Franguloside,1TBDMS,isomer #1	CC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(OC4OC(C)C(O)C(O)C4O)C=C3C(=O)C2=C1	3879.1	Semi standard non polar	33892256
Franguloside,1TBDMS,isomer #2	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C(O)C=C(OC4OC(C)C(O)C(O)C4O)C=C3C(=O)C2=C1	3876.6	Semi standard non polar	33892256
Franguloside,1TBDMS,isomer #3	CC1=CC(O)=C2C(=O)C3=C(O)C=C(OC4OC(C)C(O)C(O)C4O[Si](C)(C)C(C)(C)C)C=C3C(=O)C2=C1	3834.2	Semi standard non polar	33892256
Franguloside,1TBDMS,isomer #4	CC1=CC(O)=C2C(=O)C3=C(O)C=C(OC4OC(C)C(O)C(O[Si](C)(C)C(C)(C)C)C4O)C=C3C(=O)C2=C1	3880.2	Semi standard non polar	33892256
Franguloside,1TBDMS,isomer #5	CC1=CC(O)=C2C(=O)C3=C(O)C=C(OC4OC(C)C(O[Si](C)(C)C(C)(C)C)C(O)C4O)C=C3C(=O)C2=C1	3890.3	Semi standard non polar	33892256
Franguloside,2TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(OC4OC(C)C(O)C(O)C4O)C=C3C(=O)C2=C1	4070.3	Semi standard non polar	33892256
Franguloside,2TBDMS,isomer #10	CC1=CC(O)=C2C(=O)C3=C(O)C=C(OC4OC(C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C4O)C=C3C(=O)C2=C1	4046.5	Semi standard non polar	33892256
Franguloside,2TBDMS,isomer #2	CC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(OC4OC(C)C(O[Si](C)(C)C(C)(C)C)C(O)C4O)C=C3C(=O)C2=C1	4028.5	Semi standard non polar	33892256
Franguloside,2TBDMS,isomer #3	CC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(OC4OC(C)C(O)C(O[Si](C)(C)C(C)(C)C)C4O)C=C3C(=O)C2=C1	4006.2	Semi standard non polar	33892256
Franguloside,2TBDMS,isomer #4	CC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(OC4OC(C)C(O)C(O)C4O[Si](C)(C)C(C)(C)C)C=C3C(=O)C2=C1	3976.9	Semi standard non polar	33892256
Franguloside,2TBDMS,isomer #5	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C(O)C=C(OC4OC(C)C(O[Si](C)(C)C(C)(C)C)C(O)C4O)C=C3C(=O)C2=C1	4042.7	Semi standard non polar	33892256
Franguloside,2TBDMS,isomer #6	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C(O)C=C(OC4OC(C)C(O)C(O[Si](C)(C)C(C)(C)C)C4O)C=C3C(=O)C2=C1	4011.2	Semi standard non polar	33892256
Franguloside,2TBDMS,isomer #7	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C(O)C=C(OC4OC(C)C(O)C(O)C4O[Si](C)(C)C(C)(C)C)C=C3C(=O)C2=C1	3983.3	Semi standard non polar	33892256
Franguloside,2TBDMS,isomer #8	CC1=CC(O)=C2C(=O)C3=C(O)C=C(OC4OC(C)C(O[Si](C)(C)C(C)(C)C)C(O)C4O[Si](C)(C)C(C)(C)C)C=C3C(=O)C2=C1	4035.2	Semi standard non polar	33892256
Franguloside,2TBDMS,isomer #9	CC1=CC(O)=C2C(=O)C3=C(O)C=C(OC4OC(C)C(O)C(O[Si](C)(C)C(C)(C)C)C4O[Si](C)(C)C(C)(C)C)C=C3C(=O)C2=C1	4025.3	Semi standard non polar	33892256
Franguloside,3TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(OC4OC(C)C(O[Si](C)(C)C(C)(C)C)C(O)C4O)C=C3C(=O)C2=C1	4190.4	Semi standard non polar	33892256
Franguloside,3TBDMS,isomer #10	CC1=CC(O)=C2C(=O)C3=C(O)C=C(OC4OC(C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C4O[Si](C)(C)C(C)(C)C)C=C3C(=O)C2=C1	4190.4	Semi standard non polar	33892256
Franguloside,3TBDMS,isomer #2	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(OC4OC(C)C(O)C(O[Si](C)(C)C(C)(C)C)C4O)C=C3C(=O)C2=C1	4149.7	Semi standard non polar	33892256
Franguloside,3TBDMS,isomer #3	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(OC4OC(C)C(O)C(O)C4O[Si](C)(C)C(C)(C)C)C=C3C(=O)C2=C1	4138.6	Semi standard non polar	33892256
Franguloside,3TBDMS,isomer #4	CC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(OC4OC(C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C4O)C=C3C(=O)C2=C1	4129.6	Semi standard non polar	33892256
Franguloside,3TBDMS,isomer #5	CC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(OC4OC(C)C(O[Si](C)(C)C(C)(C)C)C(O)C4O[Si](C)(C)C(C)(C)C)C=C3C(=O)C2=C1	4122.0	Semi standard non polar	33892256
Franguloside,3TBDMS,isomer #6	CC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(OC4OC(C)C(O)C(O[Si](C)(C)C(C)(C)C)C4O[Si](C)(C)C(C)(C)C)C=C3C(=O)C2=C1	4118.7	Semi standard non polar	33892256
Franguloside,3TBDMS,isomer #7	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C(O)C=C(OC4OC(C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C4O)C=C3C(=O)C2=C1	4135.2	Semi standard non polar	33892256
Franguloside,3TBDMS,isomer #8	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C(O)C=C(OC4OC(C)C(O[Si](C)(C)C(C)(C)C)C(O)C4O[Si](C)(C)C(C)(C)C)C=C3C(=O)C2=C1	4127.6	Semi standard non polar	33892256
Franguloside,3TBDMS,isomer #9	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C(O)C=C(OC4OC(C)C(O)C(O[Si](C)(C)C(C)(C)C)C4O[Si](C)(C)C(C)(C)C)C=C3C(=O)C2=C1	4125.6	Semi standard non polar	33892256
Franguloside,4TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(OC4OC(C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C4O)C=C3C(=O)C2=C1	4271.2	Semi standard non polar	33892256
Franguloside,4TBDMS,isomer #2	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(OC4OC(C)C(O[Si](C)(C)C(C)(C)C)C(O)C4O[Si](C)(C)C(C)(C)C)C=C3C(=O)C2=C1	4254.2	Semi standard non polar	33892256
Franguloside,4TBDMS,isomer #3	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(OC4OC(C)C(O)C(O[Si](C)(C)C(C)(C)C)C4O[Si](C)(C)C(C)(C)C)C=C3C(=O)C2=C1	4259.7	Semi standard non polar	33892256
Franguloside,4TBDMS,isomer #4	CC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(OC4OC(C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C4O[Si](C)(C)C(C)(C)C)C=C3C(=O)C2=C1	4253.5	Semi standard non polar	33892256
Franguloside,4TBDMS,isomer #5	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C(O)C=C(OC4OC(C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C4O[Si](C)(C)C(C)(C)C)C=C3C(=O)C2=C1	4271.2	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 - Franguloside GC-MS (Non-derivatized) - 70eV, Positive	splash10-0072-9215000000-ea6d63c3b6272319dd1b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Franguloside GC-MS (3 TMS) - 70eV, Positive	splash10-014i-6720119000-442c6dd845e504917c42	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Franguloside 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 - Franguloside 10V, Positive-QTOF	splash10-00xr-0194400000-9687641ab8c41c3d957e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Franguloside 20V, Positive-QTOF	splash10-00di-0290000000-fd57c335ab4cbae536dc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Franguloside 40V, Positive-QTOF	splash10-0ab9-3590000000-e6dcb25b0e5fa25b1e23	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Franguloside 10V, Negative-QTOF	splash10-014i-2074900000-20f90e590e352c8491d7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Franguloside 20V, Negative-QTOF	splash10-014i-1091000000-7245294f45a793dc731c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Franguloside 40V, Negative-QTOF	splash10-014i-3390000000-386ae4b5902acf035d14	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Franguloside 10V, Negative-QTOF	splash10-014i-0071900000-ba76de5f0193c8d75aaf	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Franguloside 20V, Negative-QTOF	splash10-014i-0090000000-7bc4cd46e333b6b9afc0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Franguloside 40V, Negative-QTOF	splash10-014i-0090000000-41f0feebf5796f088465	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Franguloside 10V, Positive-QTOF	splash10-00di-0090300000-1dcd6b3e25ac2665e295	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Franguloside 20V, Positive-QTOF	splash10-00di-0091000000-8f5c09b352d446268fb7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Franguloside 40V, Positive-QTOF	splash10-00di-8192000000-0add4015624aadcf4047	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

348160

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1700711

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Franguloside (HMDB0036408)

MOL for HMDB0036408 (Franguloside)

3D MOL for HMDB0036408 (Franguloside)

3D SDF for HMDB0036408 (Franguloside)

3D-SDF for HMDB0036408 (Franguloside)

PDB for HMDB0036408 (Franguloside)

3D PDB for HMDB0036408 (Franguloside)

SMILES for HMDB0036408 (Franguloside)

INCHI for HMDB0036408 (Franguloside)

Structure for HMDB0036408 (Franguloside)

3D Structure for HMDB0036408 (Franguloside)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra