NP-MRD: Showing NP-Card for silidianin (NP0316677)

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Record Information

Version

2.0

Created at

2022-09-11 16:01:39 UTC

Updated at

2022-09-11 16:01:39 UTC

NP-MRD ID

NP0316677

Secondary Accession Numbers

None

Natural Product Identification

Common Name

silidianin

Description

Silydianin belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. Thus, silydianin is considered to be a flavonoid. silidianin is found in Silybum marianum. silidianin was first documented in 2022 (PMID: 36014565). Based on a literature review a small amount of articles have been published on Silydianin (PMID: 35975852) (PMID: 35929253) (PMID: 35631705) (PMID: 35510639).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112218012D          

 35 40  0  0  1  0            999 V2000
    1.3184   -7.6570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0798   -6.8672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6445   -6.2657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4059   -5.4760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9705   -4.8745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7319   -4.0847    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2586   -3.4748    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8863   -2.5106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1262   -2.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8746   -1.4816    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0683   -1.3067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1833   -0.5210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9896   -0.3461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2412    0.4396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0475    0.6145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6866    1.0504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1196    0.8755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6742    1.4862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3713    0.0898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1775   -0.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7321    0.5256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4292   -0.8708    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2354   -1.0457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -2.9174    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9405   -3.8643    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1579   -3.9633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1343   -3.1084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1902   -2.8467    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5927   -2.1266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1694   -2.8522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7116   -2.2304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7737   -5.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0123   -5.8524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4477   -6.4539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6863   -7.2437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  1  6  0  0  0
 24  9  1  6  0  0  0
 24 25  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
  7 30  1  1  0  0  0
 30 31  2  0  0  0  0
  5 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
  3 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END

     RDKit          3D

 57 62  0  0  0  0  0  0  0  0999 V2000
    2.9724   -2.2751    2.7512 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2513   -1.9073    2.2166 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3581   -0.9602    1.2170 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2212   -0.3307    0.6964 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3132    0.6155   -0.3006 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1661    1.3158   -0.8922 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2592    0.3910   -1.7117 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4850   -0.4934   -0.7674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3278    0.1584    0.0477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3490   -0.4063    0.9310 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5540    0.2816    0.7219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6939   -0.1966    0.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7497    0.6525   -0.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9004    0.1802   -0.6437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9816    1.0011   -0.8807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9828   -1.1481   -0.9943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9190   -2.0025   -0.7722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0029   -3.3364   -1.1248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7689   -1.5263   -0.1973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6087   -2.3617    0.0680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5684   -3.5091   -0.4213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4787   -1.8985    0.8956 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7172   -2.4073    2.1944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1579    1.6417    0.0432 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3123    2.0446    0.1129 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1611    3.4833   -0.4063 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1472    3.4743   -1.3246 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4533    2.2216   -1.3533 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8029    2.3352   -1.5836 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2380    1.3029   -2.2869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0237    1.3042   -3.4555 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5821    0.9010   -0.7493 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7212    0.2943   -0.2528 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6144   -0.6526    0.7468 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7365   -1.2912    1.2788 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0658   -3.0767    3.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3332   -2.6538    1.8993 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4825   -1.4082    3.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2635   -0.5842    1.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5716    2.0217   -1.6739 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7930   -0.1623   -2.4767 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6482   -1.5412   -0.8288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0359   -0.1507    1.9874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7194    1.7097    0.1957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9181    1.9964   -0.6170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8946   -1.5085   -1.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8513   -3.6910   -1.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5320   -2.3926    0.5839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9753   -1.6283    2.7428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6934    2.1622    0.8317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7102    2.0229    1.1325 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8879    4.1087    0.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1351    3.8008   -0.7795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9196    3.0254   -2.3050 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7655    1.6382   -1.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7161    0.5217   -0.6081 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6687   -1.1059    0.9751 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 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
  5  6  1  0
  6 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  6
 28 24  1  0
 24  9  1  0
  9  8  2  0
  8  7  1  0
  7 30  1  0
 30 31  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 34  3  1  0
  7  6  1  0
 22 10  1  0
 24 25  1  0
 19 12  1  0
 30 28  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  4 39  1  0
 32 55  1  0
 33 56  1  0
 35 57  1  0
  6 40  1  6
 25 51  1  1
 26 52  1  0
 26 53  1  0
 29 54  1  0
 24 50  1  1
  8 42  1  0
  7 41  1  6
 10 43  1  1
 13 44  1  0
 15 45  1  0
 16 46  1  0
 18 47  1  0
 22 48  1  6
 23 49  1  0
M  END


  Mrv1652309112218012D          

 35 40  0  0  1  0            999 V2000
    1.3184   -7.6570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0798   -6.8672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6445   -6.2657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4059   -5.4760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9705   -4.8745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7319   -4.0847    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2586   -3.4748    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8863   -2.5106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1262   -2.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8746   -1.4816    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0683   -1.3067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1833   -0.5210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9896   -0.3461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2412    0.4396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0475    0.6145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6866    1.0504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1196    0.8755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6742    1.4862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3713    0.0898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1775   -0.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7321    0.5256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4292   -0.8708    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2354   -1.0457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -2.9174    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9405   -3.8643    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1579   -3.9633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1343   -3.1084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1902   -2.8467    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5927   -2.1266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1694   -2.8522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7116   -2.2304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7737   -5.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0123   -5.8524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4477   -6.4539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6863   -7.2437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  1  6  0  0  0
 24  9  1  6  0  0  0
 24 25  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
  7 30  1  1  0  0  0
 30 31  2  0  0  0  0
  5 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
  3 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0316677

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)[C@@H]1[C@H]2CO[C@]3(O)[C@H]2C(=C[C@H]1C3=O)[C@H]1OC2=CC(O)=CC(O)=C2C(=O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H22O10/c1-33-16-4-9(2-3-14(16)27)18-11-7-12(20-13(18)8-34-25(20,32)24(11)31)23-22(30)21(29)19-15(28)5-10(26)6-17(19)35-23/h2-7,11,13,18,20,22-23,26-28,30,32H,8H2,1H3/t11-,13-,18+,20+,22+,23-,25-/m1/s1

> <INCHI_KEY>
CYGIJEJDYJOUAN-JSGXPVSSSA-N

> <FORMULA>
C25H22O10

> <MOLECULAR_WEIGHT>
482.441

> <EXACT_MASS>
482.121296908

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
46.514216069127386

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3R,6R,7R,10R)-3-hydroxy-10-(4-hydroxy-3-methoxyphenyl)-8-[(2R,3R)-3,5,7-trihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl]-4-oxatricyclo[4.3.1.0^{3,7}]dec-8-en-2-one

> <JCHEM_LOGP>
1.7773875736666664

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.214984017973148

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.753360360448206

> <JCHEM_PKA_STRONGEST_BASIC>
-4.02549963762407

> <JCHEM_POLAR_SURFACE_AREA>
162.98000000000002

> <JCHEM_REFRACTIVITY>
119.5055

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3R,6R,7R,10R)-3-hydroxy-10-(4-hydroxy-3-methoxyphenyl)-8-[(2R,3R)-3,5,7-trihydroxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]-4-oxatricyclo[4.3.1.0^{3,7}]dec-8-en-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       2.461 -14.293   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.016 -12.819   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.070 -11.696   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.624 -10.222   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.678  -9.099   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.233  -7.625   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.216  -6.486   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.521  -4.687   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.102  -4.232   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.632  -2.766   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.128  -2.439   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.342  -0.973   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.847  -0.646   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.317   0.821   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -3.822   1.147   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.282   1.961   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.223   1.634   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.259   2.774   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.693   0.168   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.198  -0.159   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.233   0.981   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.668  -1.626   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.173  -1.952   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.197  -5.446   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.756  -7.213   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.295  -7.398   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.251  -5.802   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.222  -5.314   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.973  -3.970   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.050  -5.324   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.062  -4.163   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.178  -9.450   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.623 -10.925   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.569 -12.047   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       5.014 -13.522   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   34                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   32                                                  
CONECT    6    5    7   25                                                  
CONECT    7    6    8   30                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   24                                                  
CONECT   10    9   11   22                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   12   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   10   23                                                  
CONECT   23   22                                                            
CONECT   24    9   25   28                                                  
CONECT   25   24    6   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   24   29   30                                             
CONECT   29   28                                                            
CONECT   30   28    7   31                                                  
CONECT   31   30                                                            
CONECT   32    5   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33    3   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

View in JSmol

Synonyms

Value	Source
Silidianin	MeSH

Chemical Formula

C₂₅H₂₂O₁₀

Average Mass

482.4410 Da

Monoisotopic Mass

482.12130 Da

IUPAC Name

(1R,3R,6R,7R,10R)-3-hydroxy-10-(4-hydroxy-3-methoxyphenyl)-8-[(2R,3R)-3,5,7-trihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl]-4-oxatricyclo[4.3.1.0^{3,7}]dec-8-en-2-one

Traditional Name

(1R,3R,6R,7R,10R)-3-hydroxy-10-(4-hydroxy-3-methoxyphenyl)-8-[(2R,3R)-3,5,7-trihydroxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]-4-oxatricyclo[4.3.1.0^{3,7}]dec-8-en-2-one

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)[C@@H]1[C@H]2CO[C@]3(O)[C@H]2C(=C[C@H]1C3=O)[C@H]1OC2=CC(O)=CC(O)=C2C(=O)[C@@H]1O

InChI Identifier

InChI=1S/C25H22O10/c1-33-16-4-9(2-3-14(16)27)18-11-7-12(20-13(18)8-34-25(20,32)24(11)31)23-22(30)21(29)19-15(28)5-10(26)6-17(19)35-23/h2-7,11,13,18,20,22-23,26-28,30,32H,8H2,1H3/t11-,13-,18+,20+,22+,23-,25-/m1/s1

InChI Key

CYGIJEJDYJOUAN-JSGXPVSSSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Silybum marianum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavanones

Alternative Parents

Substituents

Flavanone
Cyclohexylphenol
Chromone
Methoxyphenol
1-benzopyran
Benzopyran
Chromane
Phenol ether
Phenoxy compound
Anisole
Aryl ketone
Aryl alkyl ketone
Methoxybenzene
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Oxepane
Cyclohexenone
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Cyclic alcohol
Tetrahydrofuran
Hemiacetal
Secondary alcohol
Ketone
Ether
Organoheterocyclic compound
Oxacycle
Polyol
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.78	ChemAxon
pKa (Strongest Acidic)	7.75	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	162.98 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	119.51 m³·mol⁻¹	ChemAxon
Polarizability	46.51 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00008664

Chemspider ID

10154881

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11982272

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wadhwa K, Pahwa R, Kumar M, Kumar S, Sharma PC, Singh G, Verma R, Mittal V, Singh I, Kaushik D, Jeandet P: Mechanistic Insights into the Pharmacological Significance of Silymarin. Molecules. 2022 Aug 21;27(16). pii: molecules27165327. doi: 10.3390/molecules27165327. [PubMed:36014565 ]
Cetin A: Some flavolignans as potent SARS-CoV-2 inhibitors via molecular docking, molecular dynamic simulations and ADME Analysis. Curr Comput Aided Drug Des. 2022 Aug 16. pii: CAD-EPUB-125487. doi: 10.2174/1573409918666220816113516. [PubMed:35975852 ]
Tran THM, Puja AM, Kim H, Kim YJ: Nanoemulsions prepared from mountain ginseng-mediated gold nanoparticles and silydianin increase the anti-inflammatory effects by regulating NF-kappaB and MAPK signaling pathways. Biomater Adv. 2022 Jun;137:212814. doi: 10.1016/j.bioadv.2022.212814. Epub 2022 Apr 22. [PubMed:35929253 ]
Yaghoubian I, Antar M, Ghassemi S, Modarres-Sanavy SAM, Smith DL: The Effects of Hydro-Priming and Colonization with Piriformospora indica and Azotobacter chroococcum on Physio-Biochemical Traits, Flavonolignans and Fatty Acids Composition of Milk Thistle (Silybum marianum) under Saline Conditions. Plants (Basel). 2022 May 10;11(10). pii: plants11101281. doi: 10.3390/plants11101281. [PubMed:35631705 ]
Kren V, Valentova K: Silybin and its congeners: from traditional medicine to molecular effects. Nat Prod Rep. 2022 Jun 22;39(6):1264-1281. doi: 10.1039/d2np00013j. [PubMed:35510639 ]
LOTUS database [Link]

Showing NP-Card for silidianin (NP0316677)

MOL for NP0316677 (silidianin)

3D MOL for NP0316677 (silidianin)

3D SDF for NP0316677 (silidianin)

3D-SDF for NP0316677 (silidianin)

PDB for NP0316677 (silidianin)

3D PDB for NP0316677 (silidianin)

SMILES for NP0316677 (silidianin)

INCHI for NP0316677 (silidianin)

Structure for NP0316677 (silidianin)

3D Structure for NP0316677 (silidianin)