NP-MRD: Showing NP-Card for 2,3-Dehydrosilychristin (NP0085550)

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Record Information

Version

2.0

Created at

2022-04-29 06:02:29 UTC

Updated at

2022-04-29 06:02:29 UTC

NP-MRD ID

NP0085550

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,3-Dehydrosilychristin

Description

2,3-Dihydrosilychristin belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. Thus, 2,3-dihydrosilychristin is considered to be a flavonoid. 2,3-Dehydrosilychristin is found in Silybum marianum anatolicum . 2,3-Dehydrosilychristin was first documented in 2019 (PMID: 30871862). Based on a literature review very few articles have been published on 2,3-dihydrosilychristin.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652304292208022D          

 36 40  0  0  1  0            999 V2000
    1.4289   -2.4750    0.0000 O   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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   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
    0.0000    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
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0420    1.3770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7065    2.1307    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2572    2.8226    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1190    2.8452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9440    2.8452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3565    3.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1815    3.5596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5940    4.2741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9440    4.2741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3565    4.9886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1190    4.2741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7065    3.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8860    2.0445    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3340    2.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4730    2.4860    0.0000 O   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    0.8250    0.0000 C   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
    2.1434   -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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    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
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  1  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 14 22  1  0  0  0  0
 12 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 10 26  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  2  0  0  0  0
  6 27  1  0  0  0  0
  5 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 29 36  1  0  0  0  0
  2 36  1  0  0  0  0
M  END

     RDKit          3D

 55 59  0  0  0  0  0  0  0  0999 V2000
    7.5280   -2.1325   -1.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5637   -1.0495   -0.2711 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4782   -0.2640    0.0724 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2147   -0.4744   -0.4308 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2019    0.3431   -0.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8323    0.1286   -0.5782 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2632    1.3913   -0.9585 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8679    1.2409   -0.8652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1900    1.9176   -1.4472 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0621    2.9700   -2.3099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4850    1.5355   -1.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7889    0.4824   -0.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1883    0.1573   -0.0694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0873    0.8854   -0.7097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3807    0.7353   -0.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2342    1.5692   -1.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5922    1.4033   -1.2559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4386    2.2503   -1.9945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0758    0.4216   -0.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2189   -0.4258    0.2931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7744   -1.3833    1.0800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8525   -0.2719    0.2070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9629   -1.0570    0.8950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3203   -1.9699    1.6508 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5808   -0.8474    0.7628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7068   -1.6609    1.4754 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7395   -0.1631    0.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5627    0.2111   -0.0222 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8595   -0.3402    0.4657 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8314   -1.8522    0.5099 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9625   -2.3504    1.4469 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4245    1.3675    0.8391 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6760    1.5972    1.3547 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7048    0.7679    0.9609 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9697    0.9794    1.4653 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2851   -2.9194   -0.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5454   -2.6476   -1.1177 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7360   -1.8535   -2.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0336   -1.2827   -1.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8447   -0.5988   -1.3978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7238    3.4519   -2.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3336    2.0612   -1.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8335    2.3454   -1.9919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7766    3.1248   -1.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1431    0.2839   -0.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3842   -2.0430    1.6464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9748   -2.3924    2.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8665   -0.9904    0.9362 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0550    0.1000    1.4596 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6201   -2.2079   -0.5201 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8555   -2.1923    0.7602 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4757   -3.1749    1.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6047    2.0155    1.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8601    2.4176    2.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7340    0.3901    1.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 12 13  1  0
 13 25  2  0
 25 26  1  0
 25 23  1  0
 23 24  2  0
 23 22  1  0
 22 20  2  0
 20 21  1  0
 20 19  1  0
 19 17  2  0
 17 18  1  0
 17 16  1  0
 16 15  2  0
 15 14  1  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  3 34  2  0
 34 35  1  0
 34 33  1  0
 33 32  2  0
 29  6  1  0
 14 13  1  0
 32  5  1  0
 28  8  1  0
 15 22  1  0
  6 40  1  6
 10 41  1  0
 11 42  1  0
 27 48  1  0
 29 49  1  1
 30 50  1  0
 30 51  1  0
 31 52  1  0
 26 47  1  0
 21 46  1  0
 19 45  1  0
 18 44  1  0
 16 43  1  0
  4 39  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
 35 55  1  0
 33 54  1  0
 32 53  1  0
M  END

  Mrv1652304292208022D          

 36 40  0  0  1  0            999 V2000
    1.4289   -2.4750    0.0000 O   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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   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
    0.0000    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
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0420    1.3770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7065    2.1307    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2572    2.8226    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1190    2.8452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9440    2.8452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3565    3.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1815    3.5596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5940    4.2741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9440    4.2741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3565    4.9886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1190    4.2741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7065    3.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8860    2.0445    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3340    2.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4730    2.4860    0.0000 O   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    0.8250    0.0000 C   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
    2.1434   -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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    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
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  1  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 14 22  1  0  0  0  0
 12 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 10 26  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  2  0  0  0  0
  6 27  1  0  0  0  0
  5 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 29 36  1  0  0  0  0
  2 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0085550

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(OC2=C(O)C=C(C=C2[C@H]1CO)C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1)C1=CC(OC)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H20O10/c1-33-18-6-10(2-3-15(18)28)23-14(9-26)13-4-11(5-17(30)25(13)35-23)24-22(32)21(31)20-16(29)7-12(27)8-19(20)34-24/h2-8,14,23,26-30,32H,9H2,1H3/t14-,23+/m1/s1

> <INCHI_KEY>
SFNRHEPTJDJBPD-FATZIPQQSA-N

> <FORMULA>
C25H20O10

> <MOLECULAR_WEIGHT>
480.425

> <EXACT_MASS>
480.105646844

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
47.49733744166426

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,5,7-trihydroxy-2-[(2R,3S)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]-4H-chromen-4-one

> <ALOGPS_LOGP>
2.57

> <JCHEM_LOGP>
2.634936563

> <ALOGPS_LOGS>
-4.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.929113876511503

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.382098968652539

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7217972222031097

> <JCHEM_POLAR_SURFACE_AREA>
166.14000000000001

> <JCHEM_REFRACTIVITY>
123.6825

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.15e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,5,7-trihydroxy-2-[(2R,3S)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.812   2.570   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.185   3.977   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0      -2.347   5.269   0.000  0.00  0.00           H+0
HETATM   14  C   UNK     0      -3.955   5.311   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.495   5.311   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.265   6.645   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -7.805   6.645   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -8.575   7.978   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.495   7.978   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -6.265   9.312   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -3.955   7.978   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.185   6.645   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.654   3.816   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.623   4.961   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.883   4.641   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   36                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   28                                                  
CONECT    6    5    7   27                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   26                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14   23                                             
CONECT   13   12                                                            
CONECT   14   12   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   14                                                       
CONECT   23   12   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   10   23   27                                                  
CONECT   27   26    6                                                       
CONECT   28    5   29                                                       
CONECT   29   28   30   36                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   29    2                                                  
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₀O₁₀

Average Mass

480.4250 Da

Monoisotopic Mass

480.10565 Da

IUPAC Name

3,5,7-trihydroxy-2-[(2R,3S)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]-4H-chromen-4-one

Traditional Name

3,5,7-trihydroxy-2-[(2R,3S)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]chromen-4-one

CAS Registry Number

Not Available

SMILES

[H][C@]1(OC2=C(O)C=C(C=C2[C@H]1CO)C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1)C1=CC(OC)=C(O)C=C1

InChI Identifier

InChI=1S/C25H20O10/c1-33-18-6-10(2-3-15(18)28)23-14(9-26)13-4-11(5-17(30)25(13)35-23)24-22(32)21(31)20-16(29)7-12(27)8-19(20)34-24/h2-8,14,23,26-30,32H,9H2,1H3/t14-,23+/m1/s1

InChI Key

SFNRHEPTJDJBPD-FATZIPQQSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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 anatolicum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
Flavonolignan
Furanoflavone
Furanoflavonoid or dihydroflavonoid
3-hydroxyflavone
Neolignan skeleton
3'-hydroxyflavonoid
Hydroxyflavonoid
3-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
7-hydroxyflavonoid
Chromone
1-benzopyran
Benzopyran
Methoxyphenol
Coumaran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Phenol
Pyranone
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Pyran
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Heteroaromatic compound
Polyol
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Primary alcohol
Alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	2.57	ALOGPS
logP	2.63	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	6.38	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	166.14 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	123.68 m³·mol⁻¹	ChemAxon
Polarizability	47.5 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

C00055444

Chemspider ID

57530612

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

121232948

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kim JY, Kim JY, Jenis J, Li ZP, Ban YJ, Baiseitova A, Park KH: Tyrosinase inhibitory study of flavonolignans from the seeds of Silybum marianum (Milk thistle). Bioorg Med Chem. 2019 Jun 15;27(12):2499-2507. doi: 10.1016/j.bmc.2019.03.013. Epub 2019 Mar 7. [PubMed:30871862 ]

Showing NP-Card for 2,3-Dehydrosilychristin (NP0085550)

MOL for NP0085550 (2,3-Dehydrosilychristin)

3D MOL for NP0085550 (2,3-Dehydrosilychristin)

3D SDF for NP0085550 (2,3-Dehydrosilychristin)

3D-SDF for NP0085550 (2,3-Dehydrosilychristin)

PDB for NP0085550 (2,3-Dehydrosilychristin)

3D PDB for NP0085550 (2,3-Dehydrosilychristin)

SMILES for NP0085550 (2,3-Dehydrosilychristin)

INCHI for NP0085550 (2,3-Dehydrosilychristin)

Structure for NP0085550 (2,3-Dehydrosilychristin)

3D Structure for NP0085550 (2,3-Dehydrosilychristin)