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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:02:14 UTC

Update Date

2022-03-07 02:53:40 UTC

HMDB ID

HMDB0033322

Secondary Accession Numbers

HMDB33322

Metabolite Identification

Common Name

Isosilybin

Description

Isosilybin 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. Isosilybin 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 isosilybin a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Isosilybin.

Structure

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

  Mrv0541 02241218052D          

 35 39  0  0  0  0            999 V2000
   -2.5005    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5005    1.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2156    1.2376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9292    1.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9292    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6441   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9291   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2154   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5003   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5003   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2154   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9291   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6441   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3592   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6442    1.2376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6442    0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9292    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2156    0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5005    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3592    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0719    1.6501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7855    1.2376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7855    0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0719    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0719   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3570   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3567   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7867   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5003    1.2376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5003    0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7867    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.4126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3567    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3570    0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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 18  2  0  0  0  0
  4  5  1  0  0  0  0
  4 15  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 29  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 20  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 23  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 35  2  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 34  2  0  0  0  0
 28 29  1  0  0  0  0
 29 32  1  0  0  0  0
 30 31  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
 34 35  1  0  0  0  0
M  END

HMDB0253692
     RDKit          3D
Isosilybin A
 57 61  0  0  0  0  0  0  0  0999 V2000
    7.8922    0.0017    0.9705 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5172    0.7686   -0.1295 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2781    0.8968   -0.6873 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1402    0.2616   -0.2368 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9218    0.4342   -0.8451 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6561   -0.2196   -0.4167 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6797    0.8019   -0.4128 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3878    0.4796   -0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7472    1.0142   -0.6042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0019    0.6425   -0.1749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1182   -0.2825    0.8418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4546   -0.7117    1.3354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2923    0.3878    1.5161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2922    0.8001    0.6491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6629    2.1135    0.4723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6793    2.4101   -0.4222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0957    3.7294   -0.6399 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3290    1.4355   -1.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9375    0.0955   -0.9467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5691   -0.8937   -1.6522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9346   -0.2191   -0.0660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4768   -1.5731    0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3462   -2.4779    0.1620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0406   -1.8000    0.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9191   -3.0523    1.0598 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9565   -0.8180    1.4096 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2942   -0.4600    0.9955 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4670   -0.9405    1.5035 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7377   -0.8988    0.8995 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2035   -2.3363    0.7395 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2978   -2.9956    1.9532 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8547    1.2709   -1.9362 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9434    1.9299   -2.4326 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1509    1.7327   -1.7965 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2509    2.4116   -2.3149 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8609   -0.5401    0.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1353   -0.7949    1.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0122    0.5953    1.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2114   -0.3786    0.6074 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3743   -0.9937   -1.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6338    1.7363   -1.3978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9098    1.0431   -0.5988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2996   -1.1719    2.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1708    2.8789    1.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6295    4.2294   -1.3622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1302    1.6355   -1.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3869   -1.8355   -1.6283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5032   -1.8729   -0.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6774   -3.6567    0.8007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0514   -1.5421    2.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4345   -0.3729    1.5933 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3988   -2.8559    0.1569 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1194   -2.4496    0.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0904   -3.9547    1.8050 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9062    1.4423   -2.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8496    2.5881   -3.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1800    2.3316   -1.9175 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
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 11 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
  5 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 34  3  1  0
 29  6  1  0
 27  8  1  0
 24 12  1  0
 21 14  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  4 39  1  0
  6 40  1  0
  9 41  1  0
 10 42  1  0
 12 43  1  0
 15 44  1  0
 17 45  1  0
 18 46  1  0
 20 47  1  0
 24 48  1  0
 25 49  1  0
 26 50  1  0
 29 51  1  0
 30 52  1  0
 30 53  1  0
 31 54  1  0
 32 55  1  0
 33 56  1  0
 35 57  1  0
M  END

  Mrv0541 02241218052D          

 35 39  0  0  0  0            999 V2000
   -2.5005    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5005    1.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2156    1.2376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9292    1.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9292    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6441   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9291   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2154   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5003   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5003   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2154   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9291   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6441   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3592   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6442    1.2376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6442    0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9292    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2156    0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5005    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3592    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0719    1.6501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7855    1.2376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7855    0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0719    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0719   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3570   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3567   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7867   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5003    1.2376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5003    0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7867    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.4126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3567    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3570    0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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 18  2  0  0  0  0
  4  5  1  0  0  0  0
  4 15  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 29  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 20  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 23  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 35  2  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 34  2  0  0  0  0
 28 29  1  0  0  0  0
 29 32  1  0  0  0  0
 30 31  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
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033322

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(=CC=C1O)C1OC2=C(OC1CO)C=C(C=C2)C1OC2=C(C(O)=CC(O)=C2)C(=O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H22O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-18-7-12(3-5-16(18)34-24)25-23(31)22(30)21-15(29)8-13(27)9-19(21)35-25/h2-9,20,23-29,31H,10H2,1H3

> <INCHI_KEY>
FDQAOULAVFHKBX-UHFFFAOYSA-N

> <FORMULA>
C25H22O10

> <MOLECULAR_WEIGHT>
482.4362

> <EXACT_MASS>
482.121296924

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
48.507654400100435

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,5,7-trihydroxy-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>
2.35

> <JCHEM_LOGP>
2.6293160946666667

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.816800082471506

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.811772785042609

> <JCHEM_PKA_STRONGEST_BASIC>
-2.990414182412958

> <JCHEM_POLAR_SURFACE_AREA>
155.14000000000001

> <JCHEM_REFRACTIVITY>
120.29390000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.17e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,5,7-trihydroxy-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

$$$$

HMDB0253692
     RDKit          3D
Isosilybin A
 57 61  0  0  0  0  0  0  0  0999 V2000
    7.8922    0.0017    0.9705 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5172    0.7686   -0.1295 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2781    0.8968   -0.6873 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1402    0.2616   -0.2368 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9218    0.4342   -0.8451 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6561   -0.2196   -0.4167 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6797    0.8019   -0.4128 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3878    0.4796   -0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7472    1.0142   -0.6042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0019    0.6425   -0.1749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1182   -0.2825    0.8418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4546   -0.7117    1.3354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2923    0.3878    1.5161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2922    0.8001    0.6491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6629    2.1135    0.4723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6793    2.4101   -0.4222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0957    3.7294   -0.6399 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3290    1.4355   -1.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9375    0.0955   -0.9467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5691   -0.8937   -1.6522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9346   -0.2191   -0.0660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4768   -1.5731    0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3462   -2.4779    0.1620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0406   -1.8000    0.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9191   -3.0523    1.0598 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9565   -0.8180    1.4096 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2942   -0.4600    0.9955 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4670   -0.9405    1.5035 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7377   -0.8988    0.8995 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2035   -2.3363    0.7395 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2978   -2.9956    1.9532 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8547    1.2709   -1.9362 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9434    1.9299   -2.4326 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1509    1.7327   -1.7965 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2509    2.4116   -2.3149 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8609   -0.5401    0.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1353   -0.7949    1.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0122    0.5953    1.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2114   -0.3786    0.6074 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3743   -0.9937   -1.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6338    1.7363   -1.3978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9098    1.0431   -0.5988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2996   -1.1719    2.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1708    2.8789    1.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6295    4.2294   -1.3622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1302    1.6355   -1.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3869   -1.8355   -1.6283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5032   -1.8729   -0.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6774   -3.6567    0.8007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0514   -1.5421    2.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4345   -0.3729    1.5933 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3988   -2.8559    0.1569 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1194   -2.4496    0.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0904   -3.9547    1.8050 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9062    1.4423   -2.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8496    2.5881   -3.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1800    2.3316   -1.9175 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
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 11 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
  5 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 34  3  1  0
 29  6  1  0
 27  8  1  0
 24 12  1  0
 21 14  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  4 39  1  0
  6 40  1  0
  9 41  1  0
 10 42  1  0
 12 43  1  0
 15 44  1  0
 17 45  1  0
 18 46  1  0
 20 47  1  0
 24 48  1  0
 25 49  1  0
 26 50  1  0
 29 51  1  0
 30 52  1  0
 30 53  1  0
 31 54  1  0
 32 55  1  0
 33 56  1  0
 35 57  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      -4.668   4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.668   3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.002   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.335   3.080   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -7.335   4.620   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       8.669  -4.620   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       7.334  -3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.002  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.667  -3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.667  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.002  -1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.669  -1.540   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      10.004  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -8.669   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.669   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -7.335   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.002   0.770   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.668   0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0     -10.004   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.001   3.080   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -3.333   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.333   0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.001   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.001  -1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.666  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.666  -1.540   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.001  -2.310   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.335  -1.540   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.667   2.310   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.667   0.770   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.335   0.000   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.001   0.770   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       0.666   0.000   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.666   0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    2    4   18                                                  
CONECT    4    3    5   15                                                  
CONECT    5    4                                                            
CONECT    6    7                                                            
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   29                                                  
CONECT   11   10   12                                                       
CONECT   12    7   11   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15    4   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18    3   17   19                                                  
CONECT   19   18   23                                                       
CONECT   20   16                                                            
CONECT   21   22                                                            
CONECT   22    2   21   23                                                  
CONECT   23   19   22   24                                                  
CONECT   24   23   25   35                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   34                                                  
CONECT   28   27   29                                                       
CONECT   29   10   28   32                                                  
CONECT   30   31                                                            
CONECT   31   30   32                                                       
CONECT   32   29   31   33                                                  
CONECT   33   32   34                                                       
CONECT   34   27   33   35                                                  
CONECT   35   24   34                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

COMPND    HMDB0033322
HETATM    1  C1  UNL     1       7.060  -1.092   2.707  1.00  0.00           C  
HETATM    2  O1  UNL     1       7.447  -0.733   1.410  1.00  0.00           O  
HETATM    3  C2  UNL     1       6.592  -0.270   0.423  1.00  0.00           C  
HETATM    4  C3  UNL     1       5.254  -0.104   0.589  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.386   0.364  -0.406  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.960   0.501  -0.140  1.00  0.00           C  
HETATM    7  O2  UNL     1       2.120   0.106  -1.208  1.00  0.00           O  
HETATM    8  C6  UNL     1       0.744   0.159  -0.916  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.176  -0.496  -1.730  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.530  -0.438  -1.434  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.989   0.272  -0.324  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.438   0.278  -0.103  1.00  0.00           C  
HETATM   13  O3  UNL     1      -3.937  -1.029  -0.365  1.00  0.00           O  
HETATM   14  C11 UNL     1      -5.277  -1.357  -0.223  1.00  0.00           C  
HETATM   15  C12 UNL     1      -6.017  -2.105  -1.084  1.00  0.00           C  
HETATM   16  C13 UNL     1      -7.348  -2.373  -0.843  1.00  0.00           C  
HETATM   17  O4  UNL     1      -8.072  -3.158  -1.772  1.00  0.00           O  
HETATM   18  C14 UNL     1      -7.956  -1.883   0.283  1.00  0.00           C  
HETATM   19  C15 UNL     1      -7.197  -1.110   1.173  1.00  0.00           C  
HETATM   20  O5  UNL     1      -7.804  -0.614   2.302  1.00  0.00           O  
HETATM   21  C16 UNL     1      -5.879  -0.850   0.928  1.00  0.00           C  
HETATM   22  C17 UNL     1      -5.030  -0.066   1.802  1.00  0.00           C  
HETATM   23  O6  UNL     1      -5.267  -0.072   3.039  1.00  0.00           O  
HETATM   24  C18 UNL     1      -3.912   0.716   1.230  1.00  0.00           C  
HETATM   25  O7  UNL     1      -4.410   2.036   1.100  1.00  0.00           O  
HETATM   26  C19 UNL     1      -1.054   0.899   0.445  1.00  0.00           C  
HETATM   27  C20 UNL     1       0.306   0.867   0.186  1.00  0.00           C  
HETATM   28  O8  UNL     1       1.220   1.526   1.007  1.00  0.00           O  
HETATM   29  C21 UNL     1       2.479   1.816   0.367  1.00  0.00           C  
HETATM   30  C22 UNL     1       2.153   2.832  -0.700  1.00  0.00           C  
HETATM   31  O9  UNL     1       3.272   3.245  -1.420  1.00  0.00           O  
HETATM   32  C23 UNL     1       5.010   0.654  -1.608  1.00  0.00           C  
HETATM   33  C24 UNL     1       6.366   0.494  -1.802  1.00  0.00           C  
HETATM   34  C25 UNL     1       7.162   0.035  -0.799  1.00  0.00           C  
HETATM   35  O10 UNL     1       8.533  -0.123  -1.006  1.00  0.00           O  
HETATM   36  H1  UNL     1       7.676  -1.931   3.119  1.00  0.00           H  
HETATM   37  H2  UNL     1       6.014  -1.406   2.807  1.00  0.00           H  
HETATM   38  H3  UNL     1       7.236  -0.235   3.416  1.00  0.00           H  
HETATM   39  H4  UNL     1       4.815  -0.344   1.546  1.00  0.00           H  
HETATM   40  H5  UNL     1       2.728  -0.274   0.669  1.00  0.00           H  
HETATM   41  H6  UNL     1       0.158  -1.053  -2.595  1.00  0.00           H  
HETATM   42  H7  UNL     1      -2.237  -0.948  -2.068  1.00  0.00           H  
HETATM   43  H8  UNL     1      -3.898   0.947  -0.893  1.00  0.00           H  
HETATM   44  H9  UNL     1      -5.530  -2.494  -1.979  1.00  0.00           H  
HETATM   45  H10 UNL     1      -8.536  -2.636  -2.525  1.00  0.00           H  
HETATM   46  H11 UNL     1      -8.994  -2.064   0.516  1.00  0.00           H  
HETATM   47  H12 UNL     1      -7.421  -0.054   3.000  1.00  0.00           H  
HETATM   48  H13 UNL     1      -3.100   0.819   1.987  1.00  0.00           H  
HETATM   49  H14 UNL     1      -3.765   2.542   0.529  1.00  0.00           H  
HETATM   50  H15 UNL     1      -1.362   1.456   1.298  1.00  0.00           H  
HETATM   51  H16 UNL     1       3.154   2.254   1.143  1.00  0.00           H  
HETATM   52  H17 UNL     1       1.332   2.498  -1.363  1.00  0.00           H  
HETATM   53  H18 UNL     1       1.750   3.784  -0.242  1.00  0.00           H  
HETATM   54  H19 UNL     1       3.046   3.383  -2.374  1.00  0.00           H  
HETATM   55  H20 UNL     1       4.435   1.008  -2.424  1.00  0.00           H  
HETATM   56  H21 UNL     1       6.795   0.740  -2.771  1.00  0.00           H  
HETATM   57  H22 UNL     1       8.933   0.105  -1.906  1.00  0.00           H  
CONECT    1    2   36   37   38
CONECT    2    3
CONECT    3    4    4   34
CONECT    4    5   39
CONECT    5    6   32   32
CONECT    6    7   29   40
CONECT    7    8
CONECT    8    9    9   27
CONECT    9   10   41
CONECT   10   11   11   42
CONECT   11   12   26
CONECT   12   13   24   43
CONECT   13   14
CONECT   14   15   15   21
CONECT   15   16   44
CONECT   16   17   18   18
CONECT   17   45
CONECT   18   19   46
CONECT   19   20   21   21
CONECT   20   47
CONECT   21   22
CONECT   22   23   23   24
CONECT   24   25   48
CONECT   25   49
CONECT   26   27   27   50
CONECT   27   28
CONECT   28   29
CONECT   29   30   51
CONECT   30   31   52   53
CONECT   31   54
CONECT   32   33   55
CONECT   33   34   34   56
CONECT   34   35
CONECT   35   57
END

HMDB0253692
     RDKit          3D
Isosilybin A
 57 61  0  0  0  0  0  0  0  0999 V2000
    7.8922    0.0017    0.9705 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5172    0.7686   -0.1295 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2781    0.8968   -0.6873 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1402    0.2616   -0.2368 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9218    0.4342   -0.8451 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6561   -0.2196   -0.4167 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6797    0.8019   -0.4128 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3878    0.4796   -0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7472    1.0142   -0.6042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0019    0.6425   -0.1749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1182   -0.2825    0.8418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4546   -0.7117    1.3354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2923    0.3878    1.5161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2922    0.8001    0.6491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6629    2.1135    0.4723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6793    2.4101   -0.4222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0957    3.7294   -0.6399 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3290    1.4355   -1.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9375    0.0955   -0.9467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5691   -0.8937   -1.6522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9346   -0.2191   -0.0660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4768   -1.5731    0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3462   -2.4779    0.1620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0406   -1.8000    0.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9191   -3.0523    1.0598 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9565   -0.8180    1.4096 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2942   -0.4600    0.9955 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4670   -0.9405    1.5035 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7377   -0.8988    0.8995 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2035   -2.3363    0.7395 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2978   -2.9956    1.9532 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8547    1.2709   -1.9362 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9434    1.9299   -2.4326 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1509    1.7327   -1.7965 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2509    2.4116   -2.3149 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8609   -0.5401    0.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1353   -0.7949    1.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0122    0.5953    1.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2114   -0.3786    0.6074 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3743   -0.9937   -1.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6338    1.7363   -1.3978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9098    1.0431   -0.5988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2996   -1.1719    2.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1708    2.8789    1.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6295    4.2294   -1.3622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1302    1.6355   -1.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3869   -1.8355   -1.6283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5032   -1.8729   -0.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6774   -3.6567    0.8007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0514   -1.5421    2.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4345   -0.3729    1.5933 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3988   -2.8559    0.1569 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1194   -2.4496    0.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0904   -3.9547    1.8050 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9062    1.4423   -2.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8496    2.5881   -3.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1800    2.3316   -1.9175 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
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 11 26  1  0
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  5 32  2  0
 32 33  1  0
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 34  3  1  0
 29  6  1  0
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 24 12  1  0
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  1 36  1  0
  1 37  1  0
  1 38  1  0
  4 39  1  0
  6 40  1  0
  9 41  1  0
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 35 57  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Isosilybin	MeSH

Chemical Formula

C₂₅H₂₂O₁₀

Average Molecular Weight

482.4362

Monoisotopic Molecular Weight

482.121296924

IUPAC Name

3,5,7-trihydroxy-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

3,5,7-trihydroxy-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

72581-71-6

SMILES

COC1=CC(=CC=C1O)C1OC2=C(OC1CO)C=C(C=C2)C1OC2=C(C(O)=CC(O)=C2)C(=O)C1O

InChI Identifier

InChI=1S/C25H22O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-18-7-12(3-5-16(18)34-24)25-23(31)22(30)21-15(29)8-13(27)9-19(21)35-25/h2-9,20,23-29,31H,10H2,1H3

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	239 - 241 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	77.36 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	0.092 g/L	ALOGPS
logP	2.35	ALOGPS
logP	2.63	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	7.81	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	155.14 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	120.29 m³·mol⁻¹	ChemAxon
Polarizability	48.51 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	210.501	31661259
DarkChem	[M-H]-	210.602	31661259
DeepCCS	[M+H]+	201.986	30932474
DeepCCS	[M-H]-	199.59	30932474
DeepCCS	[M-2H]-	232.474	30932474
DeepCCS	[M+Na]+	207.898	30932474
AllCCS	[M+H]+	213.4	32859911
AllCCS	[M+H-H2O]+	211.3	32859911
AllCCS	[M+NH4]+	215.3	32859911
AllCCS	[M+Na]+	215.9	32859911
AllCCS	[M-H]-	209.2	32859911
AllCCS	[M+Na-2H]-	209.7	32859911
AllCCS	[M+HCOO]-	210.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isosilybin	COC1=CC(=CC=C1O)C1OC2=C(OC1CO)C=C(C=C2)C1OC2=C(C(O)=CC(O)=C2)C(=O)C1O	5622.4	Standard polar	33892256
Isosilybin	COC1=CC(=CC=C1O)C1OC2=C(OC1CO)C=C(C=C2)C1OC2=C(C(O)=CC(O)=C2)C(=O)C1O	4130.9	Standard non polar	33892256
Isosilybin	COC1=CC(=CC=C1O)C1OC2=C(OC1CO)C=C(C=C2)C1OC2=C(C(O)=CC(O)=C2)C(=O)C1O	4553.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isosilybin,1TMS,isomer #1	COC1=CC(C2OC3=CC=C(C4OC5=CC(O)=CC(O)=C5C(=O)C4O)C=C3OC2CO)=CC=C1O[Si](C)(C)C	4580.8	Semi standard non polar	33892256
Isosilybin,1TMS,isomer #2	COC1=CC(C2OC3=CC=C(C4OC5=CC(O)=CC(O)=C5C(=O)C4O)C=C3OC2CO[Si](C)(C)C)=CC=C1O	4583.9	Semi standard non polar	33892256
Isosilybin,1TMS,isomer #3	COC1=CC(C2OC3=CC=C(C4OC5=CC(O)=CC(O[Si](C)(C)C)=C5C(=O)C4O)C=C3OC2CO)=CC=C1O	4613.6	Semi standard non polar	33892256
Isosilybin,1TMS,isomer #4	COC1=CC(C2OC3=CC=C(C4OC5=CC(O[Si](C)(C)C)=CC(O)=C5C(=O)C4O)C=C3OC2CO)=CC=C1O	4596.0	Semi standard non polar	33892256
Isosilybin,1TMS,isomer #5	COC1=CC(C2OC3=CC=C(C4OC5=CC(O)=CC(O)=C5C(=O)C4O[Si](C)(C)C)C=C3OC2CO)=CC=C1O	4519.3	Semi standard non polar	33892256
Isosilybin,2TMS,isomer #1	COC1=CC(C2OC3=CC=C(C4OC5=CC(O[Si](C)(C)C)=CC(O)=C5C(=O)C4O)C=C3OC2CO)=CC=C1O[Si](C)(C)C	4437.0	Semi standard non polar	33892256
Isosilybin,2TMS,isomer #10	COC1=CC(C2OC3=CC=C(C4OC5=CC(O[Si](C)(C)C)=CC(O)=C5C(=O)C4O[Si](C)(C)C)C=C3OC2CO)=CC=C1O	4345.4	Semi standard non polar	33892256
Isosilybin,2TMS,isomer #2	COC1=CC(C2OC3=CC=C(C4OC5=CC(O)=CC(O[Si](C)(C)C)=C5C(=O)C4O)C=C3OC2CO)=CC=C1O[Si](C)(C)C	4466.1	Semi standard non polar	33892256
Isosilybin,2TMS,isomer #3	COC1=CC(C2OC3=CC=C(C4OC5=CC(O)=CC(O)=C5C(=O)C4O[Si](C)(C)C)C=C3OC2CO)=CC=C1O[Si](C)(C)C	4375.1	Semi standard non polar	33892256
Isosilybin,2TMS,isomer #4	COC1=CC(C2OC3=CC=C(C4OC5=CC(O)=CC(O)=C5C(=O)C4O)C=C3OC2CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C	4392.5	Semi standard non polar	33892256
Isosilybin,2TMS,isomer #5	COC1=CC(C2OC3=CC=C(C4OC5=CC(O[Si](C)(C)C)=CC(O)=C5C(=O)C4O)C=C3OC2CO[Si](C)(C)C)=CC=C1O	4395.9	Semi standard non polar	33892256
Isosilybin,2TMS,isomer #6	COC1=CC(C2OC3=CC=C(C4OC5=CC(O)=CC(O[Si](C)(C)C)=C5C(=O)C4O)C=C3OC2CO[Si](C)(C)C)=CC=C1O	4414.6	Semi standard non polar	33892256
Isosilybin,2TMS,isomer #7	COC1=CC(C2OC3=CC=C(C4OC5=CC(O)=CC(O)=C5C(=O)C4O[Si](C)(C)C)C=C3OC2CO[Si](C)(C)C)=CC=C1O	4328.2	Semi standard non polar	33892256
Isosilybin,2TMS,isomer #8	COC1=CC(C2OC3=CC=C(C4OC5=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C5C(=O)C4O)C=C3OC2CO)=CC=C1O	4466.7	Semi standard non polar	33892256
Isosilybin,2TMS,isomer #9	COC1=CC(C2OC3=CC=C(C4OC5=CC(O)=CC(O[Si](C)(C)C)=C5C(=O)C4O[Si](C)(C)C)C=C3OC2CO)=CC=C1O	4406.1	Semi standard non polar	33892256
Isosilybin,3TMS,isomer #1	COC1=CC(C2OC3=CC=C(C4OC5=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C5C(=O)C4O)C=C3OC2CO)=CC=C1O[Si](C)(C)C	4352.3	Semi standard non polar	33892256
Isosilybin,3TMS,isomer #10	COC1=CC(C2OC3=CC=C(C4OC5=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C5C(=O)C4O[Si](C)(C)C)C=C3OC2CO)=CC=C1O	4253.5	Semi standard non polar	33892256
Isosilybin,3TMS,isomer #2	COC1=CC(C2OC3=CC=C(C4OC5=CC(O[Si](C)(C)C)=CC(O)=C5C(=O)C4O[Si](C)(C)C)C=C3OC2CO)=CC=C1O[Si](C)(C)C	4221.6	Semi standard non polar	33892256
Isosilybin,3TMS,isomer #3	COC1=CC(C2OC3=CC=C(C4OC5=CC(O[Si](C)(C)C)=CC(O)=C5C(=O)C4O)C=C3OC2CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C	4237.6	Semi standard non polar	33892256
Isosilybin,3TMS,isomer #4	COC1=CC(C2OC3=CC=C(C4OC5=CC(O)=CC(O[Si](C)(C)C)=C5C(=O)C4O[Si](C)(C)C)C=C3OC2CO)=CC=C1O[Si](C)(C)C	4286.8	Semi standard non polar	33892256
Isosilybin,3TMS,isomer #5	COC1=CC(C2OC3=CC=C(C4OC5=CC(O)=CC(O[Si](C)(C)C)=C5C(=O)C4O)C=C3OC2CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C	4258.3	Semi standard non polar	33892256
Isosilybin,3TMS,isomer #6	COC1=CC(C2OC3=CC=C(C4OC5=CC(O)=CC(O)=C5C(=O)C4O[Si](C)(C)C)C=C3OC2CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C	4185.5	Semi standard non polar	33892256
Isosilybin,3TMS,isomer #7	COC1=CC(C2OC3=CC=C(C4OC5=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C5C(=O)C4O)C=C3OC2CO[Si](C)(C)C)=CC=C1O	4258.0	Semi standard non polar	33892256
Isosilybin,3TMS,isomer #8	COC1=CC(C2OC3=CC=C(C4OC5=CC(O[Si](C)(C)C)=CC(O)=C5C(=O)C4O[Si](C)(C)C)C=C3OC2CO[Si](C)(C)C)=CC=C1O	4137.3	Semi standard non polar	33892256
Isosilybin,3TMS,isomer #9	COC1=CC(C2OC3=CC=C(C4OC5=CC(O)=CC(O[Si](C)(C)C)=C5C(=O)C4O[Si](C)(C)C)C=C3OC2CO[Si](C)(C)C)=CC=C1O	4193.8	Semi standard non polar	33892256
Isosilybin,4TMS,isomer #1	COC1=CC(C2OC3=CC=C(C4OC5=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C5C(=O)C4O[Si](C)(C)C)C=C3OC2CO)=CC=C1O[Si](C)(C)C	4182.8	Semi standard non polar	33892256
Isosilybin,4TMS,isomer #2	COC1=CC(C2OC3=CC=C(C4OC5=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C5C(=O)C4O)C=C3OC2CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C	4165.5	Semi standard non polar	33892256
Isosilybin,4TMS,isomer #3	COC1=CC(C2OC3=CC=C(C4OC5=CC(O[Si](C)(C)C)=CC(O)=C5C(=O)C4O[Si](C)(C)C)C=C3OC2CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C	4054.8	Semi standard non polar	33892256
Isosilybin,4TMS,isomer #4	COC1=CC(C2OC3=CC=C(C4OC5=CC(O)=CC(O[Si](C)(C)C)=C5C(=O)C4O[Si](C)(C)C)C=C3OC2CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C	4109.0	Semi standard non polar	33892256
Isosilybin,4TMS,isomer #5	COC1=CC(C2OC3=CC=C(C4OC5=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C5C(=O)C4O[Si](C)(C)C)C=C3OC2CO[Si](C)(C)C)=CC=C1O	4080.2	Semi standard non polar	33892256
Isosilybin,5TMS,isomer #1	COC1=CC(C2OC3=CC=C(C4OC5=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C5C(=O)C4O[Si](C)(C)C)C=C3OC2CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C	4036.7	Semi standard non polar	33892256
Isosilybin,1TBDMS,isomer #1	COC1=CC(C2OC3=CC=C(C4OC5=CC(O)=CC(O)=C5C(=O)C4O)C=C3OC2CO)=CC=C1O[Si](C)(C)C(C)(C)C	4852.0	Semi standard non polar	33892256
Isosilybin,1TBDMS,isomer #2	COC1=CC(C2OC3=CC=C(C4OC5=CC(O)=CC(O)=C5C(=O)C4O)C=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O	4849.5	Semi standard non polar	33892256
Isosilybin,1TBDMS,isomer #3	COC1=CC(C2OC3=CC=C(C4OC5=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C5C(=O)C4O)C=C3OC2CO)=CC=C1O	4884.1	Semi standard non polar	33892256
Isosilybin,1TBDMS,isomer #4	COC1=CC(C2OC3=CC=C(C4OC5=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C5C(=O)C4O)C=C3OC2CO)=CC=C1O	4836.0	Semi standard non polar	33892256
Isosilybin,1TBDMS,isomer #5	COC1=CC(C2OC3=CC=C(C4OC5=CC(O)=CC(O)=C5C(=O)C4O[Si](C)(C)C(C)(C)C)C=C3OC2CO)=CC=C1O	4836.2	Semi standard non polar	33892256
Isosilybin,2TBDMS,isomer #1	COC1=CC(C2OC3=CC=C(C4OC5=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C5C(=O)C4O)C=C3OC2CO)=CC=C1O[Si](C)(C)C(C)(C)C	4969.0	Semi standard non polar	33892256
Isosilybin,2TBDMS,isomer #10	COC1=CC(C2OC3=CC=C(C4OC5=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C5C(=O)C4O[Si](C)(C)C(C)(C)C)C=C3OC2CO)=CC=C1O	4881.8	Semi standard non polar	33892256
Isosilybin,2TBDMS,isomer #2	COC1=CC(C2OC3=CC=C(C4OC5=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C5C(=O)C4O)C=C3OC2CO)=CC=C1O[Si](C)(C)C(C)(C)C	5032.7	Semi standard non polar	33892256
Isosilybin,2TBDMS,isomer #3	COC1=CC(C2OC3=CC=C(C4OC5=CC(O)=CC(O)=C5C(=O)C4O[Si](C)(C)C(C)(C)C)C=C3OC2CO)=CC=C1O[Si](C)(C)C(C)(C)C	4944.5	Semi standard non polar	33892256
Isosilybin,2TBDMS,isomer #4	COC1=CC(C2OC3=CC=C(C4OC5=CC(O)=CC(O)=C5C(=O)C4O)C=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	4953.5	Semi standard non polar	33892256
Isosilybin,2TBDMS,isomer #5	COC1=CC(C2OC3=CC=C(C4OC5=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C5C(=O)C4O)C=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O	4917.5	Semi standard non polar	33892256
Isosilybin,2TBDMS,isomer #6	COC1=CC(C2OC3=CC=C(C4OC5=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C5C(=O)C4O)C=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O	4962.7	Semi standard non polar	33892256
Isosilybin,2TBDMS,isomer #7	COC1=CC(C2OC3=CC=C(C4OC5=CC(O)=CC(O)=C5C(=O)C4O[Si](C)(C)C(C)(C)C)C=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O	4866.4	Semi standard non polar	33892256
Isosilybin,2TBDMS,isomer #8	COC1=CC(C2OC3=CC=C(C4OC5=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C5C(=O)C4O)C=C3OC2CO)=CC=C1O	4987.5	Semi standard non polar	33892256
Isosilybin,2TBDMS,isomer #9	COC1=CC(C2OC3=CC=C(C4OC5=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C5C(=O)C4O[Si](C)(C)C(C)(C)C)C=C3OC2CO)=CC=C1O	4962.7	Semi standard non polar	33892256
Isosilybin,3TBDMS,isomer #1	COC1=CC(C2OC3=CC=C(C4OC5=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C5C(=O)C4O)C=C3OC2CO)=CC=C1O[Si](C)(C)C(C)(C)C	5095.5	Semi standard non polar	33892256
Isosilybin,3TBDMS,isomer #10	COC1=CC(C2OC3=CC=C(C4OC5=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C5C(=O)C4O[Si](C)(C)C(C)(C)C)C=C3OC2CO)=CC=C1O	4978.8	Semi standard non polar	33892256
Isosilybin,3TBDMS,isomer #2	COC1=CC(C2OC3=CC=C(C4OC5=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C5C(=O)C4O[Si](C)(C)C(C)(C)C)C=C3OC2CO)=CC=C1O[Si](C)(C)C(C)(C)C	4973.4	Semi standard non polar	33892256
Isosilybin,3TBDMS,isomer #3	COC1=CC(C2OC3=CC=C(C4OC5=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C5C(=O)C4O)C=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	4994.2	Semi standard non polar	33892256
Isosilybin,3TBDMS,isomer #4	COC1=CC(C2OC3=CC=C(C4OC5=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C5C(=O)C4O[Si](C)(C)C(C)(C)C)C=C3OC2CO)=CC=C1O[Si](C)(C)C(C)(C)C	5024.0	Semi standard non polar	33892256
Isosilybin,3TBDMS,isomer #5	COC1=CC(C2OC3=CC=C(C4OC5=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C5C(=O)C4O)C=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	5025.7	Semi standard non polar	33892256
Isosilybin,3TBDMS,isomer #6	COC1=CC(C2OC3=CC=C(C4OC5=CC(O)=CC(O)=C5C(=O)C4O[Si](C)(C)C(C)(C)C)C=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	4898.0	Semi standard non polar	33892256
Isosilybin,3TBDMS,isomer #7	COC1=CC(C2OC3=CC=C(C4OC5=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C5C(=O)C4O)C=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O	4987.7	Semi standard non polar	33892256
Isosilybin,3TBDMS,isomer #8	COC1=CC(C2OC3=CC=C(C4OC5=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C5C(=O)C4O[Si](C)(C)C(C)(C)C)C=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O	4861.7	Semi standard non polar	33892256
Isosilybin,3TBDMS,isomer #9	COC1=CC(C2OC3=CC=C(C4OC5=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C5C(=O)C4O[Si](C)(C)C(C)(C)C)C=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O	4901.6	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 - Isosilybin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-0355900000-ee5b9ff766b73e5586de	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isosilybin GC-MS (3 TMS) - 70eV, Positive	splash10-001i-0003009000-cbd9993c968c8b9331a9	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isosilybin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isosilybin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isosilybin GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isosilybin GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isosilybin GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isosilybin GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isosilybin GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isosilybin GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isosilybin GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isosilybin GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isosilybin GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isosilybin GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isosilybin GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isosilybin GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isosilybin GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isosilybin GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isosilybin GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isosilybin GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isosilybin GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isosilybin GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isosilybin GC-MS (TMS_3_5) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isosilybin GC-MS (TMS_3_6) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isosilybin GC-MS (TMS_3_7) - 70eV, Positive	Not Available	2021-11-04	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 - Isosilybin 10V, Positive-QTOF	splash10-001i-0230900000-5cb1ac2ab3ac02603bed	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosilybin 20V, Positive-QTOF	splash10-0f79-0832900000-d026ecd80e28a5ca246e	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosilybin 40V, Positive-QTOF	splash10-0udr-0910000000-1ba1f2e1af44c627631e	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosilybin 10V, Negative-QTOF	splash10-001i-0101900000-a57d1c4a7214316bae84	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosilybin 20V, Negative-QTOF	splash10-0wpi-0622900000-95a11391a7297241cad0	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosilybin 40V, Negative-QTOF	splash10-0019-1930000000-2628eae0777ccdc0f2d3	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosilybin 10V, Negative-QTOF	splash10-001i-0000900000-0b2b3bcd8db2872500de	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosilybin 20V, Negative-QTOF	splash10-0f89-0900800000-965999825ffc8dfb3c78	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosilybin 40V, Negative-QTOF	splash10-004i-0409000000-7b2f0cf49ed015316b2d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosilybin 10V, Positive-QTOF	splash10-001i-0000900000-6e1f1cdf5a79875365f9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosilybin 20V, Positive-QTOF	splash10-0uea-0900400000-30fd2b5c32600950942e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosilybin 40V, Positive-QTOF	splash10-0udi-0902000000-9511c2921c599425355f	2021-09-25	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

3085830

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1486781

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Deep G, Oberlies NH, Kroll DJ, Agarwal R: Isosilybin B and isosilybin A inhibit growth, induce G1 arrest and cause apoptosis in human prostate cancer LNCaP and 22Rv1 cells. Carcinogenesis. 2007 Jul;28(7):1533-42. Epub 2007 Mar 26. [PubMed:17389612 ]
Deep G, Oberlies NH, Kroll DJ, Agarwal R: Isosilybin B causes androgen receptor degradation in human prostate carcinoma cells via PI3K-Akt-Mdm2-mediated pathway. Oncogene. 2008 Jun 26;27(28):3986-98. doi: 10.1038/onc.2008.45. Epub 2008 Mar 10. [PubMed:18332867 ]
Deep G, Gangar SC, Oberlies NH, Kroll DJ, Agarwal R: Isosilybin A induces apoptosis in human prostate cancer cells via targeting Akt, NF-kappaB, and androgen receptor signaling. Mol Carcinog. 2010 Oct;49(10):902-12. doi: 10.1002/mc.20670. [PubMed:20721970 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Isosilybin (HMDB0033322)

MOL for HMDB0033322 (Isosilybin)

3D MOL for HMDB0033322 (Isosilybin)

3D SDF for HMDB0033322 (Isosilybin)

3D-SDF for HMDB0033322 (Isosilybin)

PDB for HMDB0033322 (Isosilybin)

3D PDB for HMDB0033322 (Isosilybin)

SMILES for HMDB0033322 (Isosilybin)

INCHI for HMDB0033322 (Isosilybin)

Structure for HMDB0033322 (Isosilybin)

3D Structure for HMDB0033322 (Isosilybin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra