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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:37:46 UTC

Update Date

2022-03-07 02:52:36 UTC

HMDB ID

HMDB0030583

Secondary Accession Numbers

HMDB30583

Metabolite Identification

Common Name

Silibinin

Description

3,5,7-trihydroxy-2-[3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-3,4-dihydro-2H-1-benzopyran-4-one, also known as silibinin, 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. Based on a literature review very few articles have been published on 3,5,7-trihydroxy-2-[3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-3,4-dihydro-2H-1-benzopyran-4-one.

Structure

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


  Mrv0541 05061305222D          

 35 39  0  0  0  0            999 V2000
    9.2881   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0  0  0  0
  5  3  2  0  0  0  0
 11  2  1  0  0  0  0
 11  6  2  0  0  0  0
 12  3  1  0  0  0  0
 12  7  2  0  0  0  0
 13  8  2  0  0  0  0
 13  9  1  0  0  0  0
 14  4  1  0  0  0  0
 15  8  1  0  0  0  0
 16  5  1  0  0  0  0
 17  6  1  0  0  0  0
 17 14  2  0  0  0  0
 18  7  1  0  0  0  0
 18 16  2  0  0  0  0
 19  9  2  0  0  0  0
 20 10  1  0  0  0  0
 21 15  2  0  0  0  0
 21 19  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 11  1  0  0  0  0
 24 20  1  0  0  0  0
 25 12  1  0  0  0  0
 25 23  1  0  0  0  0
 26 10  1  0  0  0  0
 27 13  1  0  0  0  0
 28 14  1  0  0  0  0
 29 15  1  0  0  0  0
 30 22  2  0  0  0  0
 31 23  1  0  0  0  0
 32  1  1  0  0  0  0
 32 17  1  0  0  0  0
 33 16  1  0  0  0  0
 33 20  1  0  0  0  0
 34 18  1  0  0  0  0
 34 24  1  0  0  0  0
 35 19  1  0  0  0  0
 35 25  1  0  0  0  0
M  END

HMDB0242621
     RDKit          3D
Silymarin
 57 61  0  0  0  0  0  0  0  0999 V2000
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    6.5531   -0.4670   -1.2583 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9735   -0.5554    0.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0292   -0.3023    1.4200 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6036    0.0463    1.6086 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7999   -0.5448    0.5980 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.7895   -1.1401   -1.1440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4690   -0.1939   -1.9366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8593   -0.0334   -1.9429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4431    1.0430   -2.5790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8085    1.2093   -2.5915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4092    2.3014   -3.2366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6333    0.3085   -1.9707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0534   -0.7934   -1.3180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8993   -1.6744   -0.7063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6894   -0.9389   -1.3187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0448   -2.0680   -0.6553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6541   -3.1480   -0.5525 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6566   -1.8331   -0.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6676   -1.2133    1.1041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1112    0.8116    0.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1971    1.5773    0.9608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0880    1.0950    1.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0191    1.8218    1.7764 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3846    1.5425    1.5335 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2584    2.2761    2.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6041    2.0104    2.2933 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1409   -1.0506    2.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7506   -0.9752    1.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1002   -1.3102    0.8877 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8490   -0.6486   -2.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4694    1.0018   -2.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3997   -0.0811   -3.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0071    0.1074   -0.6394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.3510    2.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2246   -1.8683   -1.7713 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.7228   -2.4938   -0.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2285   -2.8630    0.0224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5228   -0.7763    1.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1515    1.1495    0.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5197    2.5072    1.4191 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6551    1.8960    0.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0628    3.3588    2.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1163    2.1184    3.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3380   -0.7880    3.4681 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7556   -1.3834    3.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4842   -1.2323   -0.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  4  5  1  0
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 23 24  1  0
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 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
 23 11  1  0
 20 13  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
 11 42  1  0
 14 43  1  0
 16 44  1  0
 17 45  1  0
 19 46  1  0
 23 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 05061305222D          

 35 39  0  0  0  0            999 V2000
    9.2881   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.8592   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0  0  0  0
  5  3  2  0  0  0  0
 11  2  1  0  0  0  0
 11  6  2  0  0  0  0
 12  3  1  0  0  0  0
 12  7  2  0  0  0  0
 13  8  2  0  0  0  0
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 14  4  1  0  0  0  0
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 16  5  1  0  0  0  0
 17  6  1  0  0  0  0
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 18  7  1  0  0  0  0
 18 16  2  0  0  0  0
 19  9  2  0  0  0  0
 20 10  1  0  0  0  0
 21 15  2  0  0  0  0
 21 19  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 11  1  0  0  0  0
 24 20  1  0  0  0  0
 25 12  1  0  0  0  0
 25 23  1  0  0  0  0
 26 10  1  0  0  0  0
 27 13  1  0  0  0  0
 28 14  1  0  0  0  0
 29 15  1  0  0  0  0
 30 22  2  0  0  0  0
 31 23  1  0  0  0  0
 32  1  1  0  0  0  0
 32 17  1  0  0  0  0
 33 16  1  0  0  0  0
 33 20  1  0  0  0  0
 34 18  1  0  0  0  0
 34 24  1  0  0  0  0
 35 19  1  0  0  0  0
 35 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030583

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=CC(=C1)C1OC2=C(OC1CO)C=CC(=C2)C1OC2=CC(O)=CC(O)=C2C(=O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H22O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-16-5-3-12(7-18(16)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>
SEBFKMXJBCUCAI-UHFFFAOYSA-N

> <FORMULA>
C25H22O10

> <MOLECULAR_WEIGHT>
482.4362

> <EXACT_MASS>
482.121296924

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
48.13226246969474

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,5,7-trihydroxy-2-[3-(4-hydroxy-3-methoxyphenyl)-2-(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>
9.81680052239353

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.811772790046035

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9904140611148753

> <JCHEM_POLAR_SURFACE_AREA>
155.14

> <JCHEM_REFRACTIVITY>
120.29389999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.26e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
silymarin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0242621
     RDKit          3D
Silymarin
 57 61  0  0  0  0  0  0  0  0999 V2000
    5.7784   -0.0420   -2.3482 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5531   -0.4670   -1.2583 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9735   -0.5554    0.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6466   -0.2297    0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0292   -0.3023    1.4200 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6036    0.0463    1.6086 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7999   -0.5448    0.5980 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4934   -0.0862    0.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4550   -0.8144   -0.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7543   -0.3678   -0.3700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7895   -1.1401   -1.1440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4690   -0.1939   -1.9366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8593   -0.0334   -1.9429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4431    1.0430   -2.5790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8085    1.2093   -2.5915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4092    2.3014   -3.2366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6333    0.3085   -1.9707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0534   -0.7934   -1.3180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8993   -1.6744   -0.7063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6894   -0.9389   -1.3187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0448   -2.0680   -0.6553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6541   -3.1480   -0.5525 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6566   -1.8331   -0.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6676   -1.2133    1.1041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1112    0.8116    0.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1971    1.5773    0.9608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0880    1.0950    1.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0191    1.8218    1.7764 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3846    1.5425    1.5335 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2584    2.2761    2.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6041    2.0104    2.2933 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8145   -0.7257    2.4859 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1409   -1.0506    2.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7506   -0.9752    1.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1002   -1.3102    0.8877 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8490   -0.6486   -2.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4694    1.0018   -2.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3997   -0.0811   -3.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0071    0.1074   -0.6394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.3510    2.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1696   -1.7585   -0.7222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2246   -1.8683   -1.7713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8022    1.7669   -3.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8376    2.9829   -3.7026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7036    0.4403   -1.9815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7228   -2.4938   -0.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2285   -2.8630    0.0224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5228   -0.7763    1.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1515    1.1495    0.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5197    2.5072    1.4191 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6551    1.8960    0.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0480    1.9101    3.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0628    3.3588    2.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1163    2.1184    3.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3380   -0.7880    3.4681 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7556   -1.3834    3.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4842   -1.2323   -0.0452 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  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 10 25  2  0
 25 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
 23 11  1  0
 20 13  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
 11 42  1  0
 14 43  1  0
 16 44  1  0
 17 45  1  0
 19 46  1  0
 23 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                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      17.338  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.671  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.671  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      12.003   3.850   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      16.004  -3.080   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      16.004   0.000   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1   32                                                            
CONECT    2    4   11                                                       
CONECT    3    5   12                                                       
CONECT    4    2   14                                                       
CONECT    5    3   16                                                       
CONECT    6   11   17                                                       
CONECT    7   12   18                                                       
CONECT    8   13   15                                                       
CONECT    9   13   19                                                       
CONECT   10   20   26                                                       
CONECT   11    2    6   24                                                  
CONECT   12    3    7   25                                                  
CONECT   13    8    9   27                                                  
CONECT   14    4   17   28                                                  
CONECT   15    8   21   29                                                  
CONECT   16    5   18   33                                                  
CONECT   17    6   14   32                                                  
CONECT   18    7   16   34                                                  
CONECT   19    9   21   35                                                  
CONECT   20   10   24   33                                                  
CONECT   21   15   19   22                                                  
CONECT   22   21   23   30                                                  
CONECT   23   22   25   31                                                  
CONECT   24   11   20   34                                                  
CONECT   25   12   23   35                                                  
CONECT   26   10                                                            
CONECT   27   13                                                            
CONECT   28   14                                                            
CONECT   29   15                                                            
CONECT   30   22                                                            
CONECT   31   23                                                            
CONECT   32    1   17                                                       
CONECT   33   16   20                                                       
CONECT   34   18   24                                                       
CONECT   35   19   25                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

COMPND    HMDB0030583
HETATM    1  C1  UNL     1      -5.776   0.393  -2.961  1.00  0.00           C  
HETATM    2  O1  UNL     1      -6.140  -0.604  -2.013  1.00  0.00           O  
HETATM    3  C2  UNL     1      -5.538  -0.705  -0.775  1.00  0.00           C  
HETATM    4  C3  UNL     1      -4.542   0.159  -0.376  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.946   0.045   0.873  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.872   1.037   1.198  1.00  0.00           C  
HETATM    7  O2  UNL     1      -1.983   1.157   0.144  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.633   1.001   0.238  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.187   0.699  -0.834  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.550   0.549  -0.704  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.421   0.225  -1.862  1.00  0.00           C  
HETATM   12  O3  UNL     1       3.554   1.056  -1.811  1.00  0.00           O  
HETATM   13  C10 UNL     1       4.787   0.700  -1.307  1.00  0.00           C  
HETATM   14  C11 UNL     1       5.687   1.575  -0.742  1.00  0.00           C  
HETATM   15  C12 UNL     1       6.912   1.114  -0.261  1.00  0.00           C  
HETATM   16  O4  UNL     1       7.818   2.026   0.313  1.00  0.00           O  
HETATM   17  C13 UNL     1       7.259  -0.208  -0.332  1.00  0.00           C  
HETATM   18  C14 UNL     1       6.355  -1.120  -0.905  1.00  0.00           C  
HETATM   19  O5  UNL     1       6.693  -2.446  -0.979  1.00  0.00           O  
HETATM   20  C15 UNL     1       5.168  -0.631  -1.364  1.00  0.00           C  
HETATM   21  C16 UNL     1       4.173  -1.525  -1.979  1.00  0.00           C  
HETATM   22  O6  UNL     1       4.536  -2.526  -2.635  1.00  0.00           O  
HETATM   23  C17 UNL     1       2.730  -1.245  -1.826  1.00  0.00           C  
HETATM   24  O7  UNL     1       2.063  -1.897  -2.881  1.00  0.00           O  
HETATM   25  C18 UNL     1       2.085   0.713   0.557  1.00  0.00           C  
HETATM   26  C19 UNL     1       1.282   1.017   1.654  1.00  0.00           C  
HETATM   27  C20 UNL     1      -0.071   1.161   1.502  1.00  0.00           C  
HETATM   28  O8  UNL     1      -0.960   1.465   2.542  1.00  0.00           O  
HETATM   29  C21 UNL     1      -2.236   0.803   2.506  1.00  0.00           C  
HETATM   30  C22 UNL     1      -3.006   1.412   3.664  1.00  0.00           C  
HETATM   31  O9  UNL     1      -2.292   1.139   4.828  1.00  0.00           O  
HETATM   32  C23 UNL     1      -4.374  -0.948   1.699  1.00  0.00           C  
HETATM   33  C24 UNL     1      -5.386  -1.826   1.294  1.00  0.00           C  
HETATM   34  C25 UNL     1      -5.977  -1.713   0.056  1.00  0.00           C  
HETATM   35  O10 UNL     1      -6.995  -2.595  -0.352  1.00  0.00           O  
HETATM   36  H1  UNL     1      -5.933   1.415  -2.560  1.00  0.00           H  
HETATM   37  H2  UNL     1      -6.281   0.255  -3.916  1.00  0.00           H  
HETATM   38  H3  UNL     1      -4.683   0.265  -3.141  1.00  0.00           H  
HETATM   39  H4  UNL     1      -4.212   0.954  -1.058  1.00  0.00           H  
HETATM   40  H5  UNL     1      -3.384   2.061   1.288  1.00  0.00           H  
HETATM   41  H6  UNL     1      -0.260   0.576  -1.814  1.00  0.00           H  
HETATM   42  H7  UNL     1       1.895   0.499  -2.825  1.00  0.00           H  
HETATM   43  H8  UNL     1       5.435   2.619  -0.675  1.00  0.00           H  
HETATM   44  H9  UNL     1       8.703   1.687   0.659  1.00  0.00           H  
HETATM   45  H10 UNL     1       8.192  -0.602   0.026  1.00  0.00           H  
HETATM   46  H11 UNL     1       6.126  -3.156  -1.339  1.00  0.00           H  
HETATM   47  H12 UNL     1       2.432  -1.651  -0.848  1.00  0.00           H  
HETATM   48  H13 UNL     1       2.476  -2.795  -3.008  1.00  0.00           H  
HETATM   49  H14 UNL     1       3.137   0.603   0.691  1.00  0.00           H  
HETATM   50  H15 UNL     1       1.707   1.146   2.650  1.00  0.00           H  
HETATM   51  H16 UNL     1      -2.062  -0.267   2.779  1.00  0.00           H  
HETATM   52  H17 UNL     1      -4.021   1.049   3.780  1.00  0.00           H  
HETATM   53  H18 UNL     1      -2.971   2.531   3.530  1.00  0.00           H  
HETATM   54  H19 UNL     1      -1.876   0.225   4.743  1.00  0.00           H  
HETATM   55  H20 UNL     1      -3.915  -1.050   2.678  1.00  0.00           H  
HETATM   56  H21 UNL     1      -5.706  -2.607   1.972  1.00  0.00           H  
HETATM   57  H22 UNL     1      -7.333  -3.330   0.219  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   25   25
CONECT   11   12   23   42
CONECT   12   13
CONECT   13   14   14   20
CONECT   14   15   43
CONECT   15   16   17   17
CONECT   16   44
CONECT   17   18   45
CONECT   18   19   20   20
CONECT   19   46
CONECT   20   21
CONECT   21   22   22   23
CONECT   23   24   47
CONECT   24   48
CONECT   25   26   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

HMDB0242621
     RDKit          3D
Silymarin
 57 61  0  0  0  0  0  0  0  0999 V2000
    5.7784   -0.0420   -2.3482 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5531   -0.4670   -1.2583 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9735   -0.5554    0.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6466   -0.2297    0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0292   -0.3023    1.4200 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6036    0.0463    1.6086 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7999   -0.5448    0.5980 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4934   -0.0862    0.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4550   -0.8144   -0.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7543   -0.3678   -0.3700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7895   -1.1401   -1.1440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4690   -0.1939   -1.9366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8593   -0.0334   -1.9429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4431    1.0430   -2.5790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8085    1.2093   -2.5915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4092    2.3014   -3.2366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6333    0.3085   -1.9707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0534   -0.7934   -1.3180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8993   -1.6744   -0.7063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6894   -0.9389   -1.3187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0448   -2.0680   -0.6553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6541   -3.1480   -0.5525 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6566   -1.8331   -0.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6676   -1.2133    1.1041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1112    0.8116    0.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1971    1.5773    0.9608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0880    1.0950    1.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0191    1.8218    1.7764 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3846    1.5425    1.5335 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2584    2.2761    2.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6041    2.0104    2.2933 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8145   -0.7257    2.4859 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1409   -1.0506    2.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7506   -0.9752    1.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1002   -1.3102    0.8877 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8490   -0.6486   -2.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4694    1.0018   -2.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3997   -0.0811   -3.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0071    0.1074   -0.6394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.3510    2.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1696   -1.7585   -0.7222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2246   -1.8683   -1.7713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8022    1.7669   -3.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8376    2.9829   -3.7026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7036    0.4403   -1.9815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7228   -2.4938   -0.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2285   -2.8630    0.0224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5228   -0.7763    1.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1515    1.1495    0.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5197    2.5072    1.4191 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6551    1.8960    0.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0480    1.9101    3.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0628    3.3588    2.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1163    2.1184    3.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3380   -0.7880    3.4681 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7556   -1.3834    3.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4842   -1.2323   -0.0452 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  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 10 25  2  0
 25 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
 23 11  1  0
 20 13  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
 11 42  1  0
 14 43  1  0
 16 44  1  0
 17 45  1  0
 19 46  1  0
 23 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

View in JSmol View Stereo Labels

Synonyms

Value	Source
Silibinin	Kegg
Silybin	Kegg
Flavobin	HMDB
Flavobin spofa	HMDB
Karsil	HMDB, MeSH
Legalon	HMDB, MeSH
Silibin	HMDB
Silibinin, inn	HMDB
Silibinina	HMDB
Silibinine	HMDB
Silibininum	HMDB
Silimarin	HMDB, MeSH
Silliver	HMDB
Silybin (7ci)	HMDB
Silybine	HMDB
Silybum substance e6	HMDB
Silymarin I	HMDB
Silymarine I	HMDB
Carsil	MeSH, HMDB
2,3 Dehydrosilybin	MeSH, HMDB
2,3-Dehydrosilybin	MeSH, HMDB
Alepa forte	MeSH, HMDB
Alepa-forte	MeSH, HMDB
Ardeyhepan	MeSH, HMDB
Cefasilymarin	MeSH, HMDB
Hepa merz sil	MeSH, HMDB
Hepa loges	MeSH, HMDB
Hepa-merz sil	MeSH, HMDB
HepaBesch	MeSH, HMDB
Hepar pasc	MeSH, HMDB
Hepar-pasc	MeSH, HMDB
Heparsyx	MeSH, HMDB
Heplant	MeSH, HMDB
Lagosa	MeSH, HMDB
Silibinin a	MeSH, HMDB
Silibinin b	MeSH, HMDB
Silymarin	MeSH, HMDB
Durasilymarin	MeSH, HMDB
Hepa-loges	MeSH, HMDB
Legalon forte	MeSH, HMDB
Silybin a	MeSH, HMDB
Silybin b	MeSH, HMDB
Silybinin	MeSH, HMDB

Chemical Formula

C₂₅H₂₂O₁₀

Average Molecular Weight

482.4362

Monoisotopic Molecular Weight

482.121296924

IUPAC Name

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

Traditional Name

silymarin

CAS Registry Number

22888-70-6

SMILES

COC1=C(O)C=CC(=C1)C1OC2=C(OC1CO)C=CC(=C2)C1OC2=CC(O)=CC(O)=C2C(=O)C1O

InChI Identifier

InChI=1S/C25H22O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-16-5-3-12(7-18(16)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

SEBFKMXJBCUCAI-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

Dihyroflavonols (C07610 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	167 °C	Not Available
Boiling Point	793.03 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	77.36 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	4.232 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.093 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	48.13 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]+	210.47	31661259
DarkChem	[M-H]-	210.929	31661259
DeepCCS	[M+H]+	203.026	30932474
DeepCCS	[M-H]-	200.63	30932474
DeepCCS	[M-2H]-	233.514	30932474
DeepCCS	[M+Na]+	208.939	30932474
AllCCS	[M+H]+	213.1	32859911
AllCCS	[M+H-H2O]+	211.0	32859911
AllCCS	[M+NH4]+	215.1	32859911
AllCCS	[M+Na]+	215.6	32859911
AllCCS	[M-H]-	209.5	32859911
AllCCS	[M+Na-2H]-	210.0	32859911
AllCCS	[M+HCOO]-	210.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Silibinin	COC1=C(O)C=CC(=C1)C1OC2=C(OC1CO)C=CC(=C2)C1OC2=CC(O)=CC(O)=C2C(=O)C1O	5630.7	Standard polar	33892256
Silibinin	COC1=C(O)C=CC(=C1)C1OC2=C(OC1CO)C=CC(=C2)C1OC2=CC(O)=CC(O)=C2C(=O)C1O	4139.0	Standard non polar	33892256
Silibinin	COC1=C(O)C=CC(=C1)C1OC2=C(OC1CO)C=CC(=C2)C1OC2=CC(O)=CC(O)=C2C(=O)C1O	4561.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Silibinin,1TMS,isomer #1	COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O)=C5C(=O)C4O)=CC=C3OC2CO)=CC=C1O[Si](C)(C)C	4593.3	Semi standard non polar	33892256
Silibinin,1TMS,isomer #2	COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O)=C5C(=O)C4O)=CC=C3OC2CO[Si](C)(C)C)=CC=C1O	4592.2	Semi standard non polar	33892256
Silibinin,1TMS,isomer #3	COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C)=CC(O)=C5C(=O)C4O)=CC=C3OC2CO)=CC=C1O	4605.6	Semi standard non polar	33892256
Silibinin,1TMS,isomer #4	COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O[Si](C)(C)C)=C5C(=O)C4O)=CC=C3OC2CO)=CC=C1O	4624.0	Semi standard non polar	33892256
Silibinin,1TMS,isomer #5	COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O)=C5C(=O)C4O[Si](C)(C)C)=CC=C3OC2CO)=CC=C1O	4531.0	Semi standard non polar	33892256
Silibinin,2TMS,isomer #1	COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C)=CC(O)=C5C(=O)C4O)=CC=C3OC2CO)=CC=C1O[Si](C)(C)C	4449.5	Semi standard non polar	33892256
Silibinin,2TMS,isomer #10	COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O[Si](C)(C)C)=C5C(=O)C4O[Si](C)(C)C)=CC=C3OC2CO)=CC=C1O	4413.2	Semi standard non polar	33892256
Silibinin,2TMS,isomer #2	COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O[Si](C)(C)C)=C5C(=O)C4O)=CC=C3OC2CO)=CC=C1O[Si](C)(C)C	4476.0	Semi standard non polar	33892256
Silibinin,2TMS,isomer #3	COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O)=C5C(=O)C4O[Si](C)(C)C)=CC=C3OC2CO)=CC=C1O[Si](C)(C)C	4382.6	Semi standard non polar	33892256
Silibinin,2TMS,isomer #4	COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O)=C5C(=O)C4O)=CC=C3OC2CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C	4400.1	Semi standard non polar	33892256
Silibinin,2TMS,isomer #5	COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C)=CC(O)=C5C(=O)C4O)=CC=C3OC2CO[Si](C)(C)C)=CC=C1O	4403.1	Semi standard non polar	33892256
Silibinin,2TMS,isomer #6	COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O[Si](C)(C)C)=C5C(=O)C4O)=CC=C3OC2CO[Si](C)(C)C)=CC=C1O	4417.7	Semi standard non polar	33892256
Silibinin,2TMS,isomer #7	COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O)=C5C(=O)C4O[Si](C)(C)C)=CC=C3OC2CO[Si](C)(C)C)=CC=C1O	4332.3	Semi standard non polar	33892256
Silibinin,2TMS,isomer #8	COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C5C(=O)C4O)=CC=C3OC2CO)=CC=C1O	4477.6	Semi standard non polar	33892256
Silibinin,2TMS,isomer #9	COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C)=CC(O)=C5C(=O)C4O[Si](C)(C)C)=CC=C3OC2CO)=CC=C1O	4352.9	Semi standard non polar	33892256
Silibinin,3TMS,isomer #1	COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C5C(=O)C4O)=CC=C3OC2CO)=CC=C1O[Si](C)(C)C	4363.0	Semi standard non polar	33892256
Silibinin,3TMS,isomer #10	COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C5C(=O)C4O[Si](C)(C)C)=CC=C3OC2CO)=CC=C1O	4258.6	Semi standard non polar	33892256
Silibinin,3TMS,isomer #2	COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C)=CC(O)=C5C(=O)C4O[Si](C)(C)C)=CC=C3OC2CO)=CC=C1O[Si](C)(C)C	4228.8	Semi standard non polar	33892256
Silibinin,3TMS,isomer #3	COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C)=CC(O)=C5C(=O)C4O)=CC=C3OC2CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C	4244.5	Semi standard non polar	33892256
Silibinin,3TMS,isomer #4	COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O[Si](C)(C)C)=C5C(=O)C4O[Si](C)(C)C)=CC=C3OC2CO)=CC=C1O[Si](C)(C)C	4293.6	Semi standard non polar	33892256
Silibinin,3TMS,isomer #5	COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O[Si](C)(C)C)=C5C(=O)C4O)=CC=C3OC2CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C	4262.6	Semi standard non polar	33892256
Silibinin,3TMS,isomer #6	COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O)=C5C(=O)C4O[Si](C)(C)C)=CC=C3OC2CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C	4189.3	Semi standard non polar	33892256
Silibinin,3TMS,isomer #7	COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C5C(=O)C4O)=CC=C3OC2CO[Si](C)(C)C)=CC=C1O	4262.7	Semi standard non polar	33892256
Silibinin,3TMS,isomer #8	COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C)=CC(O)=C5C(=O)C4O[Si](C)(C)C)=CC=C3OC2CO[Si](C)(C)C)=CC=C1O	4140.9	Semi standard non polar	33892256
Silibinin,3TMS,isomer #9	COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O[Si](C)(C)C)=C5C(=O)C4O[Si](C)(C)C)=CC=C3OC2CO[Si](C)(C)C)=CC=C1O	4197.2	Semi standard non polar	33892256
Silibinin,4TMS,isomer #1	COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C5C(=O)C4O[Si](C)(C)C)=CC=C3OC2CO)=CC=C1O[Si](C)(C)C	4188.3	Semi standard non polar	33892256
Silibinin,4TMS,isomer #2	COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C5C(=O)C4O)=CC=C3OC2CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C	4170.8	Semi standard non polar	33892256
Silibinin,4TMS,isomer #3	COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C)=CC(O)=C5C(=O)C4O[Si](C)(C)C)=CC=C3OC2CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C	4058.7	Semi standard non polar	33892256
Silibinin,4TMS,isomer #4	COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O[Si](C)(C)C)=C5C(=O)C4O[Si](C)(C)C)=CC=C3OC2CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C	4114.7	Semi standard non polar	33892256
Silibinin,4TMS,isomer #5	COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C5C(=O)C4O[Si](C)(C)C)=CC=C3OC2CO[Si](C)(C)C)=CC=C1O	4084.0	Semi standard non polar	33892256
Silibinin,5TMS,isomer #1	COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C5C(=O)C4O[Si](C)(C)C)=CC=C3OC2CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C	4037.5	Semi standard non polar	33892256
Silibinin,1TBDMS,isomer #1	COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O)=C5C(=O)C4O)=CC=C3OC2CO)=CC=C1O[Si](C)(C)C(C)(C)C	4863.8	Semi standard non polar	33892256
Silibinin,1TBDMS,isomer #2	COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O)=C5C(=O)C4O)=CC=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O	4856.4	Semi standard non polar	33892256
Silibinin,1TBDMS,isomer #3	COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C5C(=O)C4O)=CC=C3OC2CO)=CC=C1O	4846.1	Semi standard non polar	33892256
Silibinin,1TBDMS,isomer #4	COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C5C(=O)C4O)=CC=C3OC2CO)=CC=C1O	4894.1	Semi standard non polar	33892256
Silibinin,1TBDMS,isomer #5	COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O)=C5C(=O)C4O[Si](C)(C)C(C)(C)C)=CC=C3OC2CO)=CC=C1O	4847.1	Semi standard non polar	33892256
Silibinin,2TBDMS,isomer #1	COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C5C(=O)C4O)=CC=C3OC2CO)=CC=C1O[Si](C)(C)C(C)(C)C	4976.0	Semi standard non polar	33892256
Silibinin,2TBDMS,isomer #10	COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C5C(=O)C4O[Si](C)(C)C(C)(C)C)=CC=C3OC2CO)=CC=C1O	4970.5	Semi standard non polar	33892256
Silibinin,2TBDMS,isomer #2	COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C5C(=O)C4O)=CC=C3OC2CO)=CC=C1O[Si](C)(C)C(C)(C)C	5039.1	Semi standard non polar	33892256
Silibinin,2TBDMS,isomer #3	COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O)=C5C(=O)C4O[Si](C)(C)C(C)(C)C)=CC=C3OC2CO)=CC=C1O[Si](C)(C)C(C)(C)C	4953.1	Semi standard non polar	33892256
Silibinin,2TBDMS,isomer #4	COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O)=C5C(=O)C4O)=CC=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	4958.1	Semi standard non polar	33892256
Silibinin,2TBDMS,isomer #5	COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C5C(=O)C4O)=CC=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O	4920.6	Semi standard non polar	33892256
Silibinin,2TBDMS,isomer #6	COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C5C(=O)C4O)=CC=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O	4965.5	Semi standard non polar	33892256
Silibinin,2TBDMS,isomer #7	COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O)=C5C(=O)C4O[Si](C)(C)C(C)(C)C)=CC=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O	4868.9	Semi standard non polar	33892256
Silibinin,2TBDMS,isomer #8	COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C5C(=O)C4O)=CC=C3OC2CO)=CC=C1O	4993.2	Semi standard non polar	33892256
Silibinin,2TBDMS,isomer #9	COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C5C(=O)C4O[Si](C)(C)C(C)(C)C)=CC=C3OC2CO)=CC=C1O	4891.4	Semi standard non polar	33892256
Silibinin,3TBDMS,isomer #1	COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C5C(=O)C4O)=CC=C3OC2CO)=CC=C1O[Si](C)(C)C(C)(C)C	5103.6	Semi standard non polar	33892256
Silibinin,3TBDMS,isomer #10	COC1=CC(C2OC3=CC(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)=CC=C3OC2CO)=CC=C1O	4984.8	Semi standard non polar	33892256
Silibinin,3TBDMS,isomer #2	COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C5C(=O)C4O[Si](C)(C)C(C)(C)C)=CC=C3OC2CO)=CC=C1O[Si](C)(C)C(C)(C)C	4978.8	Semi standard non polar	33892256
Silibinin,3TBDMS,isomer #3	COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C5C(=O)C4O)=CC=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	4997.4	Semi standard non polar	33892256
Silibinin,3TBDMS,isomer #4	COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C5C(=O)C4O[Si](C)(C)C(C)(C)C)=CC=C3OC2CO)=CC=C1O[Si](C)(C)C(C)(C)C	5029.9	Semi standard non polar	33892256
Silibinin,3TBDMS,isomer #5	COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C5C(=O)C4O)=CC=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	5028.7	Semi standard non polar	33892256
Silibinin,3TBDMS,isomer #6	COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O)=C5C(=O)C4O[Si](C)(C)C(C)(C)C)=CC=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	4898.5	Semi standard non polar	33892256
Silibinin,3TBDMS,isomer #7	COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C5C(=O)C4O)=CC=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O	4989.8	Semi standard non polar	33892256
Silibinin,3TBDMS,isomer #8	COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C5C(=O)C4O[Si](C)(C)C(C)(C)C)=CC=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O	4862.0	Semi standard non polar	33892256
Silibinin,3TBDMS,isomer #9	COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C5C(=O)C4O[Si](C)(C)C(C)(C)C)=CC=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O	4900.4	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 - Silibinin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-0455900000-36b82ae0b0aeac8e7ee0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Silibinin GC-MS (3 TMS) - 70eV, Positive	splash10-001i-0003009000-cbd9993c968c8b9331a9	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Silibinin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Silibinin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Silibinin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Silibinin 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Silibinin DI-ESI-qTof , Positive-QTOF	splash10-0a4i-0002090000-91ea766cf462829a9260	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Silibinin DI-ESI-qTof , Negative-QTOF	splash10-00lr-0102900400-ed276357d0ccebb3d370	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Silibinin LC-ESI-qTof , Positive-QTOF	splash10-0f6t-2942100000-4792bc912cef07546d46	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Silibinin LC-ESI-TOF , negative-QTOF	splash10-001i-0002900000-811667e96533dac778b9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Silibinin LC-ESI-TOF , negative-QTOF	splash10-001i-0000900000-b2d2752da4d986f4e3af	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Silibinin LC-ESI-TOF , negative-QTOF	splash10-001i-0000900000-6fdb5df34264f81cc4ad	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Silibinin LC-ESI-TOF , negative-QTOF	splash10-001i-0003900000-1b715e5192005890816e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Silibinin , positive-QTOF	splash10-0f6t-2942100000-4792bc912cef07546d46	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Silibinin 20V, Negative-QTOF	splash10-001i-0001900000-c78b9a76622fdee660db	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Silibinin 30V, Negative-QTOF	splash10-0udi-0754900000-293e8e3155acd4776870	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Silibinin 10V, Negative-QTOF	splash10-001i-0000900000-5462b344502c8958cbfe	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Silibinin 50V, Positive-QTOF	splash10-0gvk-0930000000-415706d7a9007d78d585	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Silibinin 10V, Positive-QTOF	splash10-001i-0100900000-991a30cf6721b9ec6ae2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Silibinin 50V, Negative-QTOF	splash10-0udi-0930000000-f8d2ffdcbd89edcdce23	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Silibinin 40V, Negative-QTOF	splash10-0ufr-0941000000-0efa09253cf03f29f287	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Silibinin 20V, Positive-QTOF	splash10-0i11-0922800000-53a9b5c1156fc7538573	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Silibinin 40V, Positive-QTOF	splash10-0f6t-0941000000-36232650400070cbb158	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Silibinin 30V, Positive-QTOF	splash10-0uea-0941300000-e59ac841aaab0eaba4ba	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Silibinin 10V, Positive-QTOF	splash10-001i-0230900000-ff1d4c98753e257ea235	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Silibinin 20V, Positive-QTOF	splash10-0f79-0731900000-f0807aa0220a07f57ab8	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Silibinin 40V, Positive-QTOF	splash10-0uk9-0920000000-8b3e0a0d017c0e0cba9a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Silibinin 10V, Negative-QTOF	splash10-001i-0101900000-dfaaf0e3e335ff1fdde5	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Silibinin 20V, Negative-QTOF	splash10-0i30-0622900000-6b3d60833f796db5d985	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Silibinin 40V, Negative-QTOF	splash10-0fui-1930000000-26f4134e3a2660dff186	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Silibinin 10V, Negative-QTOF	splash10-001i-0000900000-0b2b3bcd8db2872500de	2021-09-22	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1108841

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Zi X, Zhang J, Agarwal R, Pollak M: Silibinin up-regulates insulin-like growth factor-binding protein 3 expression and inhibits proliferation of androgen-independent prostate cancer cells. Cancer Res. 2000 Oct 15;60(20):5617-20. [PubMed:11059749 ]
Singh RP, Dhanalakshmi S, Agarwal C, Agarwal R: Silibinin strongly inhibits growth and survival of human endothelial cells via cell cycle arrest and downregulation of survivin, Akt and NF-kappaB: implications for angioprevention and antiangiogenic therapy. Oncogene. 2005 Feb 10;24(7):1188-202. [PubMed:15558015 ]
Singh RP, Deep G, Blouin MJ, Pollak MN, Agarwal R: Silibinin suppresses in vivo growth of human prostate carcinoma PC-3 tumor xenograft. Carcinogenesis. 2007 Dec;28(12):2567-74. Epub 2007 Oct 4. [PubMed:17916909 ]
Yoo HG, Jung SN, Hwang YS, Park JS, Kim MH, Jeong M, Ahn SJ, Ahn BW, Shin BA, Park RK, Jung YD: Involvement of NF-kappaB and caspases in silibinin-induced apoptosis of endothelial cells. Int J Mol Med. 2004 Jan;13(1):81-6. [PubMed:14654975 ]
Zeng J, Sun Y, Wu K, Li L, Zhang G, Yang Z, Wang Z, Zhang D, Xue Y, Chen Y, Zhu G, Wang X, He D: Chemopreventive and chemotherapeutic effects of intravesical silibinin against bladder cancer by acting on mitochondria. Mol Cancer Ther. 2011 Jan;10(1):104-16. doi: 10.1158/1535-7163.MCT-10-0577. [PubMed:21220495 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Silibinin (HMDB0030583)

MOL for HMDB0030583 (Silibinin)

3D MOL for HMDB0030583 (Silibinin)

3D SDF for HMDB0030583 (Silibinin)

3D-SDF for HMDB0030583 (Silibinin)

PDB for HMDB0030583 (Silibinin)

3D PDB for HMDB0030583 (Silibinin)

SMILES for HMDB0030583 (Silibinin)

INCHI for HMDB0030583 (Silibinin)

Structure for HMDB0030583 (Silibinin)

3D Structure for HMDB0030583 (Silibinin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra