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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:02:25 UTC

Update Date

2022-03-07 02:53:40 UTC

HMDB ID

HMDB0033325

Secondary Accession Numbers

HMDB33325

Metabolite Identification

Common Name

Silandrin

Description

Silandrin belongs to the class of organic compounds known as flavonolignans. These are non-conventional lignans that derived from flavonoids. They are characterized by a p-dioxin ring substituted at one carbon atom by a C3C6 (phenylpropan) group and fused to the B-ring of the 2-phenylchromene moiety. Silandrin has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, green vegetables, and robusta coffees (Coffea canephora). This could make silandrin a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Silandrin.

Structure

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


  Mrv0541 02241214242D          

 34 38  0  0  0  0            999 V2000
    1.0019   -3.5661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0814   -2.4443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0814   -3.2457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7224   -3.6464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7224   -4.4479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0814   -4.8486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3610    4.8486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3610    4.0472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3602    3.6464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3602    2.8449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3610    2.4443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3610    1.6427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3602    1.2419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3602    0.4405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0814    0.0398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0814   -0.8413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2807   -4.8486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3602   -4.4479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3602   -3.6464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3610   -3.2457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3610   -2.4443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3602   -2.0435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3602   -1.2419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3610   -0.8413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3610    0.0398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0019    0.4405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0019    1.2419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7231    1.6427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3646    1.2419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4443   -4.8486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0019    2.8449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0019    3.6464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7231    4.0472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4443    3.6464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  2  0  0  0  0
  2  3  1  0  0  0  0
  2 22  1  0  0  0  0
  3  4  1  0  0  0  0
  3 19  2  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5 30  1  0  0  0  0
  6 18  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 32  2  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 31  2  0  0  0  0
 12 13  1  0  0  0  0
 12 27  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 25  2  0  0  0  0
 15 16  2  0  0  0  0
 16 23  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END

HMDB0033325
     RDKit          3D
Silandrin
 56 60  0  0  0  0  0  0  0  0999 V2000
   -7.0684    3.1138    0.3478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5706    1.7925    0.1803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6775    0.7369    0.0567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3136    0.9350    0.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4261   -0.1254   -0.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9896    0.1358    0.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2561   -0.5680   -0.9825 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8851   -0.3465   -1.0142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0965   -0.6470   -2.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2714   -0.4195   -2.1108 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8818    0.1272   -1.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3491    0.3752   -1.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0547   -0.3702   -2.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5014   -0.0406   -2.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2248    0.1936   -3.0242 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1049    0.0099   -0.7037 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4824    0.0768   -0.5532 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2341    0.0923   -1.7236 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0535    0.1246    0.7031 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2288    0.1047    1.8145 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7985    0.1529    3.0970 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8505    0.0379    1.6737 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2776   -0.0103    0.3995 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9034   -0.0774    0.2264 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0991    0.4336    0.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2822    0.2072    0.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0273    0.5334    1.2314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3214   -0.0857    1.3249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0421   -1.5724    1.5617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3101   -1.7506    2.7391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9464   -1.3847   -0.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3288   -1.5655   -0.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2158   -0.5214   -0.1032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5808   -0.7580   -0.1432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5890    3.5026   -0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3498    3.1700    1.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9222    3.8005    0.5732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9566    1.9556    0.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8115    1.2247   -0.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6038   -1.0813   -2.9584 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7911   -0.6959   -3.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5226    1.4703   -1.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7296   -0.0873   -3.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9593   -1.4492   -1.8994 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2428    0.1413   -1.6125 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1262    0.1758    0.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0497   -0.7134    3.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1881    0.0214    2.5352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5819    0.8666    0.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8879    0.3402    2.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9981   -2.1231    1.7286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4342   -1.9839    0.7401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4133   -2.6993    2.9919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2795   -2.2084   -0.2901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6934   -2.5818   -0.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2298    0.0144   -0.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 11 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
  5 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 33  3  1  0
 28  6  1  0
 26  8  1  0
 24 12  1  0
 23 16  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  4 38  1  0
  6 39  1  0
  9 40  1  0
 10 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 18 45  1  0
 19 46  1  0
 21 47  1  0
 22 48  1  0
 25 49  1  0
 28 50  1  0
 29 51  1  0
 29 52  1  0
 30 53  1  0
 31 54  1  0
 32 55  1  0
 34 56  1  0
M  END


  Mrv0541 02241214242D          

 34 38  0  0  0  0            999 V2000
    1.0019   -3.5661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0814   -2.4443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0814   -3.2457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7224   -3.6464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7224   -4.4479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0814   -4.8486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3610    4.8486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3610    4.0472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3602    3.6464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3602    2.8449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3610    2.4443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3610    1.6427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3602    1.2419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3602    0.4405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0814    0.0398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0814   -0.8413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2807   -4.8486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3602   -4.4479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3602   -3.6464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3610   -3.2457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3610   -2.4443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3602   -2.0435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3602   -1.2419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3610   -0.8413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3610    0.0398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0019    0.4405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0019    1.2419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7231    1.6427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3646    1.2419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4443   -4.8486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0019    2.8449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0019    3.6464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7231    4.0472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4443    3.6464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  2  0  0  0  0
  2  3  1  0  0  0  0
  2 22  1  0  0  0  0
  3  4  1  0  0  0  0
  3 19  2  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5 30  1  0  0  0  0
  6 18  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 32  2  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 31  2  0  0  0  0
 12 13  1  0  0  0  0
 12 27  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 25  2  0  0  0  0
 15 16  2  0  0  0  0
 16 23  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033325

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=CC(=C1)C1OC2=C(OC1CO)C=C(C=C2)C1CC(=O)C2=C(O1)C=C(O)C=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C25H22O9/c1-31-20-7-13(2-4-15(20)28)25-23(11-26)33-21-6-12(3-5-18(21)34-25)19-10-17(30)24-16(29)8-14(27)9-22(24)32-19/h2-9,19,23,25-29H,10-11H2,1H3

> <INCHI_KEY>
CRPGUMMYQABYES-UHFFFAOYSA-N

> <FORMULA>
C25H22O9

> <MOLECULAR_WEIGHT>
466.4368

> <EXACT_MASS>
466.126382302

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
47.80305015009715

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-2-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
3.08

> <JCHEM_LOGP>
3.3444745553333335

> <ALOGPS_LOGS>
-4.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.84075095207411

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.9173728122747935

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9904141823858925

> <JCHEM_POLAR_SURFACE_AREA>
134.91000000000003

> <JCHEM_REFRACTIVITY>
118.95569999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.68e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dihydroxy-2-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033325
     RDKit          3D
Silandrin
 56 60  0  0  0  0  0  0  0  0999 V2000
   -7.0684    3.1138    0.3478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5706    1.7925    0.1803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6775    0.7369    0.0567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3136    0.9350    0.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4261   -0.1254   -0.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9896    0.1358    0.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2561   -0.5680   -0.9825 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8851   -0.3465   -1.0142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0965   -0.6470   -2.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2714   -0.4195   -2.1108 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8818    0.1272   -1.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3491    0.3752   -1.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0547   -0.3702   -2.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5014   -0.0406   -2.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2248    0.1936   -3.0242 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1049    0.0099   -0.7037 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4824    0.0768   -0.5532 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2341    0.0923   -1.7236 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0535    0.1246    0.7031 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2288    0.1047    1.8145 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7985    0.1529    3.0970 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8505    0.0379    1.6737 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2776   -0.0103    0.3995 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9034   -0.0774    0.2264 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0991    0.4336    0.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2822    0.2072    0.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0273    0.5334    1.2314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3214   -0.0857    1.3249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0421   -1.5724    1.5617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3101   -1.7506    2.7391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9464   -1.3847   -0.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3288   -1.5655   -0.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2158   -0.5214   -0.1032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5808   -0.7580   -0.1432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5890    3.5026   -0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3498    3.1700    1.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9222    3.8005    0.5732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9566    1.9556    0.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8115    1.2247   -0.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6038   -1.0813   -2.9584 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7911   -0.6959   -3.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5226    1.4703   -1.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7296   -0.0873   -3.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9593   -1.4492   -1.8994 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2428    0.1413   -1.6125 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1262    0.1758    0.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0497   -0.7134    3.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1881    0.0214    2.5352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5819    0.8666    0.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8879    0.3402    2.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9981   -2.1231    1.7286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4342   -1.9839    0.7401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4133   -2.6993    2.9919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2795   -2.2084   -0.2901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6934   -2.5818   -0.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2298    0.0144   -0.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 11 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
  5 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 33  3  1  0
 28  6  1  0
 26  8  1  0
 24 12  1  0
 23 16  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  4 38  1  0
  6 39  1  0
  9 40  1  0
 10 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 18 45  1  0
 19 46  1  0
 21 47  1  0
 22 48  1  0
 25 49  1  0
 28 50  1  0
 29 51  1  0
 29 52  1  0
 30 53  1  0
 31 54  1  0
 32 55  1  0
 34 56  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  O   UNK     0       1.870  -6.657   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      -2.019  -4.563   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.019  -6.059   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.215  -6.807   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.215  -8.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.019  -9.051   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.674   9.051   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.674   7.555   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.672   6.807   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.672   5.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.674   4.563   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.674   3.066   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.672   2.318   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.672   0.822   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.019   0.074   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.019  -1.570   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.524  -9.051   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.672  -8.303   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.672  -6.807   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.674  -6.059   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.674  -4.563   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.672  -3.815   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.672  -2.318   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.674  -1.570   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.674   0.074   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.870   0.822   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.870   2.318   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.216   3.066   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.414   2.318   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -4.563  -9.051   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.870   5.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.870   6.807   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.216   7.555   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       4.563   6.807   0.000  0.00  0.00           C+0
CONECT    1   20                                                            
CONECT    2    3   22                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   30                                                  
CONECT    6    5   18                                                       
CONECT    7    8                                                            
CONECT    8    7    9   32                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   31                                                  
CONECT   12   11   13   27                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   25                                                  
CONECT   15   14   16                                                       
CONECT   16   15   23                                                       
CONECT   17   18                                                            
CONECT   18    6   17   19                                                  
CONECT   19    3   18   20                                                  
CONECT   20    1   19   21                                                  
CONECT   21   20   22                                                       
CONECT   22    2   21   23                                                  
CONECT   23   16   22   24                                                  
CONECT   24   23   25                                                       
CONECT   25   14   24   26                                                  
CONECT   26   25   27                                                       
CONECT   27   12   26   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30    5                                                            
CONECT   31   11   32                                                       
CONECT   32    8   31   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

COMPND    HMDB0033325
HETATM    1  C1  UNL     1      -7.068   3.114   0.348  1.00  0.00           C  
HETATM    2  O1  UNL     1      -7.571   1.793   0.180  1.00  0.00           O  
HETATM    3  C2  UNL     1      -6.677   0.737   0.057  1.00  0.00           C  
HETATM    4  C3  UNL     1      -5.314   0.935   0.092  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.426  -0.125  -0.032  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.990   0.136   0.009  1.00  0.00           C  
HETATM    7  O2  UNL     1      -2.256  -0.568  -0.982  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.885  -0.347  -1.014  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.097  -0.647  -2.095  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.271  -0.420  -2.111  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.882   0.127  -1.012  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.349   0.375  -1.018  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.055  -0.370  -2.102  1.00  0.00           C  
HETATM   14  C12 UNL     1       5.501  -0.041  -2.029  1.00  0.00           C  
HETATM   15  O3  UNL     1       6.225   0.194  -3.024  1.00  0.00           O  
HETATM   16  C13 UNL     1       6.105   0.010  -0.704  1.00  0.00           C  
HETATM   17  C14 UNL     1       7.482   0.077  -0.553  1.00  0.00           C  
HETATM   18  O4  UNL     1       8.234   0.092  -1.724  1.00  0.00           O  
HETATM   19  C15 UNL     1       8.054   0.125   0.703  1.00  0.00           C  
HETATM   20  C16 UNL     1       7.229   0.105   1.815  1.00  0.00           C  
HETATM   21  O5  UNL     1       7.798   0.153   3.097  1.00  0.00           O  
HETATM   22  C17 UNL     1       5.851   0.038   1.674  1.00  0.00           C  
HETATM   23  C18 UNL     1       5.278  -0.010   0.399  1.00  0.00           C  
HETATM   24  O6  UNL     1       3.903  -0.077   0.226  1.00  0.00           O  
HETATM   25  C19 UNL     1       1.099   0.434   0.081  1.00  0.00           C  
HETATM   26  C20 UNL     1      -0.282   0.207   0.105  1.00  0.00           C  
HETATM   27  O7  UNL     1      -1.027   0.533   1.231  1.00  0.00           O  
HETATM   28  C21 UNL     1      -2.321  -0.086   1.325  1.00  0.00           C  
HETATM   29  C22 UNL     1      -2.042  -1.572   1.562  1.00  0.00           C  
HETATM   30  O8  UNL     1      -1.310  -1.751   2.739  1.00  0.00           O  
HETATM   31  C23 UNL     1      -4.946  -1.385  -0.192  1.00  0.00           C  
HETATM   32  C24 UNL     1      -6.329  -1.566  -0.225  1.00  0.00           C  
HETATM   33  C25 UNL     1      -7.216  -0.521  -0.103  1.00  0.00           C  
HETATM   34  O9  UNL     1      -8.581  -0.758  -0.143  1.00  0.00           O  
HETATM   35  H1  UNL     1      -6.589   3.503  -0.560  1.00  0.00           H  
HETATM   36  H2  UNL     1      -6.350   3.170   1.203  1.00  0.00           H  
HETATM   37  H3  UNL     1      -7.922   3.801   0.573  1.00  0.00           H  
HETATM   38  H4  UNL     1      -4.957   1.956   0.221  1.00  0.00           H  
HETATM   39  H5  UNL     1      -2.812   1.225  -0.245  1.00  0.00           H  
HETATM   40  H6  UNL     1      -0.604  -1.081  -2.958  1.00  0.00           H  
HETATM   41  H7  UNL     1       1.791  -0.696  -3.017  1.00  0.00           H  
HETATM   42  H8  UNL     1       3.523   1.470  -1.049  1.00  0.00           H  
HETATM   43  H9  UNL     1       3.730  -0.087  -3.123  1.00  0.00           H  
HETATM   44  H10 UNL     1       3.959  -1.449  -1.899  1.00  0.00           H  
HETATM   45  H11 UNL     1       9.243   0.141  -1.613  1.00  0.00           H  
HETATM   46  H12 UNL     1       9.126   0.176   0.766  1.00  0.00           H  
HETATM   47  H13 UNL     1       8.050  -0.713   3.584  1.00  0.00           H  
HETATM   48  H14 UNL     1       5.188   0.021   2.535  1.00  0.00           H  
HETATM   49  H15 UNL     1       1.582   0.867   0.951  1.00  0.00           H  
HETATM   50  H16 UNL     1      -2.888   0.340   2.163  1.00  0.00           H  
HETATM   51  H17 UNL     1      -2.998  -2.123   1.729  1.00  0.00           H  
HETATM   52  H18 UNL     1      -1.434  -1.984   0.740  1.00  0.00           H  
HETATM   53  H19 UNL     1      -1.413  -2.699   2.992  1.00  0.00           H  
HETATM   54  H20 UNL     1      -4.279  -2.208  -0.290  1.00  0.00           H  
HETATM   55  H21 UNL     1      -6.693  -2.582  -0.354  1.00  0.00           H  
HETATM   56  H22 UNL     1      -9.230   0.014  -0.053  1.00  0.00           H  
CONECT    1    2   35   36   37
CONECT    2    3
CONECT    3    4    4   33
CONECT    4    5   38
CONECT    5    6   31   31
CONECT    6    7   28   39
CONECT    7    8
CONECT    8    9    9   26
CONECT    9   10   40
CONECT   10   11   11   41
CONECT   11   12   25
CONECT   12   13   24   42
CONECT   13   14   43   44
CONECT   14   15   15   16
CONECT   16   17   17   23
CONECT   17   18   19
CONECT   18   45
CONECT   19   20   20   46
CONECT   20   21   22
CONECT   21   47
CONECT   22   23   23   48
CONECT   23   24
CONECT   25   26   26   49
CONECT   26   27
CONECT   27   28
CONECT   28   29   50
CONECT   29   30   51   52
CONECT   30   53
CONECT   31   32   54
CONECT   32   33   33   55
CONECT   33   34
CONECT   34   56
END

HMDB0033325
     RDKit          3D
Silandrin
 56 60  0  0  0  0  0  0  0  0999 V2000
   -7.0684    3.1138    0.3478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5706    1.7925    0.1803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6775    0.7369    0.0567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3136    0.9350    0.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4261   -0.1254   -0.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9896    0.1358    0.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2561   -0.5680   -0.9825 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8851   -0.3465   -1.0142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0965   -0.6470   -2.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2714   -0.4195   -2.1108 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8818    0.1272   -1.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3491    0.3752   -1.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0547   -0.3702   -2.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5014   -0.0406   -2.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2248    0.1936   -3.0242 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1049    0.0099   -0.7037 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4824    0.0768   -0.5532 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2341    0.0923   -1.7236 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0535    0.1246    0.7031 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2288    0.1047    1.8145 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7985    0.1529    3.0970 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8505    0.0379    1.6737 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2776   -0.0103    0.3995 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9034   -0.0774    0.2264 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0991    0.4336    0.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2822    0.2072    0.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0273    0.5334    1.2314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3214   -0.0857    1.3249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0421   -1.5724    1.5617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3101   -1.7506    2.7391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9464   -1.3847   -0.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3288   -1.5655   -0.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2158   -0.5214   -0.1032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5808   -0.7580   -0.1432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5890    3.5026   -0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3498    3.1700    1.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9222    3.8005    0.5732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9566    1.9556    0.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8115    1.2247   -0.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6038   -1.0813   -2.9584 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7911   -0.6959   -3.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5226    1.4703   -1.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7296   -0.0873   -3.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9593   -1.4492   -1.8994 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2428    0.1413   -1.6125 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1262    0.1758    0.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0497   -0.7134    3.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1881    0.0214    2.5352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5819    0.8666    0.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8879    0.3402    2.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9981   -2.1231    1.7286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4342   -1.9839    0.7401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4133   -2.6993    2.9919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2795   -2.2084   -0.2901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6934   -2.5818   -0.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2298    0.0144   -0.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 11 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
  5 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 33  3  1  0
 28  6  1  0
 26  8  1  0
 24 12  1  0
 23 16  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  4 38  1  0
  6 39  1  0
  9 40  1  0
 10 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 18 45  1  0
 19 46  1  0
 21 47  1  0
 22 48  1  0
 25 49  1  0
 28 50  1  0
 29 51  1  0
 29 52  1  0
 30 53  1  0
 31 54  1  0
 32 55  1  0
 34 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₅H₂₂O₉

Average Molecular Weight

466.4368

Monoisotopic Molecular Weight

466.126382302

IUPAC Name

5,7-dihydroxy-2-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

5,7-dihydroxy-2-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

70815-32-6

SMILES

COC1=C(O)C=CC(=C1)C1OC2=C(OC1CO)C=C(C=C2)C1CC(=O)C2=C(O1)C=C(O)C=C2O

InChI Identifier

InChI=1S/C25H22O9/c1-31-20-7-13(2-4-15(20)28)25-23(11-26)33-21-6-12(3-5-18(21)34-25)19-10-17(30)24-16(29)8-14(27)9-22(24)32-19/h2-9,19,23,25-29H,10-11H2,1H3

InChI Key

CRPGUMMYQABYES-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonolignans. These are non-conventional lignans that derived from flavonoids. They are characterized by a p-dioxin ring substituted at one carbon atom by a C3C6 (phenylpropan) group and fused to the B-ring of the 2-phenylchromene moiety.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Flavonolignans

Sub Class

Not Available

Direct Parent

Flavonolignans

Alternative Parents

Substituents

Flavonolignan
Hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavanone
Flavan
2-phenylbenzo-1,4-dioxane
Phenylbenzodioxane
Chromone
Methoxyphenol
Benzo-1,4-dioxane
Benzodioxane
Chromane
1-benzopyran
Benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Para-dioxin
Vinylogous acid
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Alcohol
Primary alcohol
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0033325)
Cell membrane (HMDB: HMDB0033325)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033325)

Source

Exogenous

Exogenous (HMDB: HMDB0033325)

Food

Food (HMDB: HMDB0033325)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Endogenous

Plant

Plant (HMDB: HMDB0033325)
Coffea (HMDB: HMDB0033325)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033325)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	234 - 236 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	34.17 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.017 g/L	ALOGPS
logP	3.08	ALOGPS
logP	3.34	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	7.92	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	134.91 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	118.96 m³·mol⁻¹	ChemAxon
Polarizability	47.8 Å³	ChemAxon
Number of Rings	5	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]+	207.132	31661259
DarkChem	[M-H]-	206.067	31661259
DeepCCS	[M+H]+	202.863	30932474
DeepCCS	[M-H]-	200.468	30932474
DeepCCS	[M-2H]-	233.351	30932474
DeepCCS	[M+Na]+	208.776	30932474
AllCCS	[M+H]+	211.0	32859911
AllCCS	[M+H-H2O]+	208.7	32859911
AllCCS	[M+NH4]+	213.0	32859911
AllCCS	[M+Na]+	213.6	32859911
AllCCS	[M-H]-	206.9	32859911
AllCCS	[M+Na-2H]-	207.1	32859911
AllCCS	[M+HCOO]-	207.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.94 minutes	32390414
Predicted by Siyang on May 30, 2022	12.9094 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.2 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2570.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	204.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	177.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	160.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	166.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	654.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	541.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	120.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1068.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	515.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1500.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	398.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	413.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	311.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	197.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	66.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Silandrin	COC1=C(O)C=CC(=C1)C1OC2=C(OC1CO)C=C(C=C2)C1CC(=O)C2=C(O1)C=C(O)C=C2O	5555.2	Standard polar	33892256
Silandrin	COC1=C(O)C=CC(=C1)C1OC2=C(OC1CO)C=C(C=C2)C1CC(=O)C2=C(O1)C=C(O)C=C2O	4134.4	Standard non polar	33892256
Silandrin	COC1=C(O)C=CC(=C1)C1OC2=C(OC1CO)C=C(C=C2)C1CC(=O)C2=C(O1)C=C(O)C=C2O	4476.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Silandrin,1TMS,isomer #1	COC1=CC(C2OC3=CC=C(C4CC(=O)C5=C(O)C=C(O)C=C5O4)C=C3OC2CO)=CC=C1O[Si](C)(C)C	4442.5	Semi standard non polar	33892256
Silandrin,1TMS,isomer #2	COC1=CC(C2OC3=CC=C(C4CC(=O)C5=C(O)C=C(O)C=C5O4)C=C3OC2CO[Si](C)(C)C)=CC=C1O	4447.7	Semi standard non polar	33892256
Silandrin,1TMS,isomer #3	COC1=CC(C2OC3=CC=C(C4CC(=O)C5=C(O)C=C(O[Si](C)(C)C)C=C5O4)C=C3OC2CO)=CC=C1O	4473.2	Semi standard non polar	33892256
Silandrin,1TMS,isomer #4	COC1=CC(C2OC3=CC=C(C4CC(=O)C5=C(C=C(O)C=C5O[Si](C)(C)C)O4)C=C3OC2CO)=CC=C1O	4464.8	Semi standard non polar	33892256
Silandrin,2TMS,isomer #1	COC1=CC(C2OC3=CC=C(C4CC(=O)C5=C(C=C(O)C=C5O[Si](C)(C)C)O4)C=C3OC2CO)=CC=C1O[Si](C)(C)C	4374.4	Semi standard non polar	33892256
Silandrin,2TMS,isomer #2	COC1=CC(C2OC3=CC=C(C4CC(=O)C5=C(O)C=C(O[Si](C)(C)C)C=C5O4)C=C3OC2CO)=CC=C1O[Si](C)(C)C	4391.3	Semi standard non polar	33892256
Silandrin,2TMS,isomer #3	COC1=CC(C2OC3=CC=C(C4CC(=O)C5=C(O)C=C(O)C=C5O4)C=C3OC2CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C	4321.9	Semi standard non polar	33892256
Silandrin,2TMS,isomer #4	COC1=CC(C2OC3=CC=C(C4CC(=O)C5=C(C=C(O)C=C5O[Si](C)(C)C)O4)C=C3OC2CO[Si](C)(C)C)=CC=C1O	4334.1	Semi standard non polar	33892256
Silandrin,2TMS,isomer #5	COC1=CC(C2OC3=CC=C(C4CC(=O)C5=C(O)C=C(O[Si](C)(C)C)C=C5O4)C=C3OC2CO[Si](C)(C)C)=CC=C1O	4344.6	Semi standard non polar	33892256
Silandrin,2TMS,isomer #6	COC1=CC(C2OC3=CC=C(C4CC(=O)C5=C(C=C(O[Si](C)(C)C)C=C5O[Si](C)(C)C)O4)C=C3OC2CO)=CC=C1O	4375.4	Semi standard non polar	33892256
Silandrin,3TMS,isomer #1	COC1=CC(C2OC3=CC=C(C4CC(=O)C5=C(C=C(O[Si](C)(C)C)C=C5O[Si](C)(C)C)O4)C=C3OC2CO)=CC=C1O[Si](C)(C)C	4311.0	Semi standard non polar	33892256
Silandrin,3TMS,isomer #2	COC1=CC(C2OC3=CC=C(C4CC(=O)C5=C(C=C(O)C=C5O[Si](C)(C)C)O4)C=C3OC2CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C	4215.7	Semi standard non polar	33892256
Silandrin,3TMS,isomer #3	COC1=CC(C2OC3=CC=C(C4CC(=O)C5=C(O)C=C(O[Si](C)(C)C)C=C5O4)C=C3OC2CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C	4215.5	Semi standard non polar	33892256
Silandrin,3TMS,isomer #4	COC1=CC(C2OC3=CC=C(C4CC(=O)C5=C(C=C(O[Si](C)(C)C)C=C5O[Si](C)(C)C)O4)C=C3OC2CO[Si](C)(C)C)=CC=C1O	4209.0	Semi standard non polar	33892256
Silandrin,4TMS,isomer #1	COC1=CC(C2OC3=CC=C(C4CC(=O)C5=C(C=C(O[Si](C)(C)C)C=C5O[Si](C)(C)C)O4)C=C3OC2CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C	4143.4	Semi standard non polar	33892256
Silandrin,1TBDMS,isomer #1	COC1=CC(C2OC3=CC=C(C4CC(=O)C5=C(O)C=C(O)C=C5O4)C=C3OC2CO)=CC=C1O[Si](C)(C)C(C)(C)C	4721.1	Semi standard non polar	33892256
Silandrin,1TBDMS,isomer #2	COC1=CC(C2OC3=CC=C(C4CC(=O)C5=C(O)C=C(O)C=C5O4)C=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O	4693.9	Semi standard non polar	33892256
Silandrin,1TBDMS,isomer #3	COC1=CC(C2OC3=CC=C(C4CC(=O)C5=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C5O4)C=C3OC2CO)=CC=C1O	4728.3	Semi standard non polar	33892256
Silandrin,1TBDMS,isomer #4	COC1=CC(C2OC3=CC=C(C4CC(=O)C5=C(C=C(O)C=C5O[Si](C)(C)C(C)(C)C)O4)C=C3OC2CO)=CC=C1O	4739.9	Semi standard non polar	33892256
Silandrin,2TBDMS,isomer #1	COC1=CC(C2OC3=CC=C(C4CC(=O)C5=C(C=C(O)C=C5O[Si](C)(C)C(C)(C)C)O4)C=C3OC2CO)=CC=C1O[Si](C)(C)C(C)(C)C	4916.6	Semi standard non polar	33892256
Silandrin,2TBDMS,isomer #2	COC1=CC(C2OC3=CC=C(C4CC(=O)C5=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C5O4)C=C3OC2CO)=CC=C1O[Si](C)(C)C(C)(C)C	4893.8	Semi standard non polar	33892256
Silandrin,2TBDMS,isomer #3	COC1=CC(C2OC3=CC=C(C4CC(=O)C5=C(O)C=C(O)C=C5O4)C=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	4845.9	Semi standard non polar	33892256
Silandrin,2TBDMS,isomer #4	COC1=CC(C2OC3=CC=C(C4CC(=O)C5=C(C=C(O)C=C5O[Si](C)(C)C(C)(C)C)O4)C=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O	4842.0	Semi standard non polar	33892256
Silandrin,2TBDMS,isomer #5	COC1=CC(C2OC3=CC=C(C4CC(=O)C5=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C5O4)C=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O	4832.0	Semi standard non polar	33892256
Silandrin,2TBDMS,isomer #6	COC1=CC(C2OC3=CC=C(C4CC(=O)C5=C(C=C(O[Si](C)(C)C(C)(C)C)C=C5O[Si](C)(C)C(C)(C)C)O4)C=C3OC2CO)=CC=C1O	4878.7	Semi standard non polar	33892256
Silandrin,3TBDMS,isomer #1	COC1=CC(C2OC3=CC=C(C4CC(=O)C5=C(C=C(O[Si](C)(C)C(C)(C)C)C=C5O[Si](C)(C)C(C)(C)C)O4)C=C3OC2CO)=CC=C1O[Si](C)(C)C(C)(C)C	4992.2	Semi standard non polar	33892256
Silandrin,3TBDMS,isomer #2	COC1=CC(C2OC3=CC=C(C4CC(=O)C5=C(C=C(O)C=C5O[Si](C)(C)C(C)(C)C)O4)C=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	4912.4	Semi standard non polar	33892256
Silandrin,3TBDMS,isomer #3	COC1=CC(C2OC3=CC=C(C4CC(=O)C5=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C5O4)C=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	4927.5	Semi standard non polar	33892256
Silandrin,3TBDMS,isomer #4	COC1=CC(C2OC3=CC=C(C4CC(=O)C5=C(C=C(O[Si](C)(C)C(C)(C)C)C=C5O[Si](C)(C)C(C)(C)C)O4)C=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O	4887.7	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 - Silandrin GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-0510900000-f225907ba53e29a1815b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Silandrin GC-MS (3 TMS) - 70eV, Positive	splash10-014i-0100009000-41df6882fbc167173b66	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Silandrin 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 - Silandrin 10V, Positive-QTOF	splash10-014i-0331900000-771b05fa4260ac75a4d3	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Silandrin 20V, Positive-QTOF	splash10-0ukj-0730900000-718ffcbeac1db1b523df	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Silandrin 40V, Positive-QTOF	splash10-0udi-0910000000-aa64aa96bc9576ee3950	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Silandrin 10V, Negative-QTOF	splash10-014i-0000900000-b0eadb59e1fa44dcef9a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Silandrin 20V, Negative-QTOF	splash10-014j-0320900000-112e93a58365d7b94f93	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Silandrin 40V, Negative-QTOF	splash10-0gbc-3970200000-caf631eb7f383a4d9915	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Silandrin 10V, Positive-QTOF	splash10-014i-0000900000-af171f020e0ab7e8b3a1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Silandrin 20V, Positive-QTOF	splash10-0uxs-0900400000-8ae36505e4fc33de9de0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Silandrin 40V, Positive-QTOF	splash10-0udi-0902000000-a766d15b5b6d889d5d80	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Silandrin 10V, Negative-QTOF	splash10-014i-0000900000-c82bf1faf99b96e0d078	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Silandrin 20V, Negative-QTOF	splash10-0gb9-0900800000-34ffbc03e2aaf5bcfd01	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Silandrin 40V, Negative-QTOF	splash10-03di-0409000000-fddf021b0ae1d503ce68	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

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

4481258

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1834821

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 Silandrin (HMDB0033325)

MOL for HMDB0033325 (Silandrin)

3D MOL for HMDB0033325 (Silandrin)

3D SDF for HMDB0033325 (Silandrin)

3D-SDF for HMDB0033325 (Silandrin)

PDB for HMDB0033325 (Silandrin)

3D PDB for HMDB0033325 (Silandrin)

SMILES for HMDB0033325 (Silandrin)

INCHI for HMDB0033325 (Silandrin)

Structure for HMDB0033325 (Silandrin)

3D Structure for HMDB0033325 (Silandrin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra