NP-MRD: Showing NP-Card for (1r,8s,9r,16r)-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0²,⁷.0¹⁴,¹⁷]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,9,12-tetrol (NP0329322)

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Record Information

Version

2.0

Created at

2022-09-12 13:36:28 UTC

Updated at

2022-09-12 13:36:28 UTC

NP-MRD ID

NP0329322

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,8s,9r,16r)-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0²,⁷.0¹⁴,¹⁷]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,9,12-tetrol

Description

Hemsleyanol A belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. (1r,8s,9r,16r)-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0²,⁷.0¹⁴,¹⁷]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,9,12-tetrol is found in Shorea hemsleyana. Based on a literature review very few articles have been published on Hemsleyanol A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122215362D          

 35 40  0  0  1  0            999 V2000
    2.7333   -3.7688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3643   -3.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5408   -2.9814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1719   -2.2435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6265   -1.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2575   -0.8171    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7623   -0.1645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5541   -0.3960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7496   -1.1975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1505    0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9550    0.9756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5514    1.5456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1632    1.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5668    0.6370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8183    0.9838    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0804    0.6149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4986    1.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2970    0.9952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5166    0.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3151   -0.0075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9377   -0.3878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0913   -0.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4326   -0.8294    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0857   -1.5779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1184    1.9349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6954    1.7996    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2832    2.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0757    3.1770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6635    3.7560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4588    3.5364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0465    4.1153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6662    2.7379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0784    2.1590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4500   -1.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8189   -2.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 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
 16 22  1  0  0  0  0
 22 23  1  0  0  0  0
  6 23  1  0  0  0  0
 23 24  1  1  0  0  0
 17 25  1  0  0  0  0
 25 26  1  0  0  0  0
 15 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  2  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
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 27 33  1  0  0  0  0
  5 34  1  0  0  0  0
 34 35  2  0  0  0  0
  2 35  1  0  0  0  0
M  END

     RDKit          3D

 57 62  0  0  0  0  0  0  0  0999 V2000
    5.8712    1.2976    2.3428 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8837    0.9755    1.4007 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6618    0.4560    1.8161 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6901    0.1411    0.8637 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9203    0.3356   -0.4743 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8903    0.0269   -1.4840 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1185   -1.1226   -1.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8957   -2.2710   -1.2781 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1293   -2.2743   -1.8454 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3878   -3.5360   -0.9344 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1689   -3.6436   -0.3645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3661   -4.8721   -0.0116 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5806   -2.4990   -0.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1237   -1.2437   -0.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0942   -0.2213   -0.0858 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5087    1.1148    0.2125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0860    1.6131    1.3435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6428    2.8773    1.7562 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3181    3.5710    1.0587 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7355    4.8158    1.4892 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8647    3.0195   -0.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4558    1.7892   -0.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1147    1.3019   -1.7153 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1366    1.0291   -2.6692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0124    0.7235    1.8450 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0049   -0.4827    1.0509 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4597   -0.5690    0.6336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0497    0.5668    0.1249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3675    0.6072   -0.2776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0803   -0.5638   -0.1445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4198   -0.6101   -0.5279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5299   -1.7216    0.3591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2134   -1.7011    0.7432 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1343    0.8489   -0.8508 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1175    1.1717    0.0574 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5251    0.5559    2.5801 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4965    0.3091    2.8748 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7743   -0.2605    1.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4072   -0.2384   -2.4513 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7498   -1.6243   -2.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9888   -4.4178   -1.1339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1704   -5.2125    0.9219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5362   -2.5910    0.3204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7922    0.0032   -0.9717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0923    3.2830    2.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290    5.3445    1.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6349    3.5622   -0.6430 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8372    2.0409   -2.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0724    0.0764   -2.6424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7230   -1.2585    1.7632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4542    1.4924    0.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8219    1.5227   -0.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5991   -0.8727   -1.4932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1462   -2.6347    0.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7748   -2.6068    1.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3184    1.0025   -1.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0664    1.5738   -0.2499 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 23  1  0
 23  6  1  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 35  1  0
 35 34  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 26  1  0
 26 25  1  0
 25 17  1  0
 17 16  2  0
 16 22  1  0
 22 21  2  0
 21 19  1  0
 19 20  1  0
 19 18  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 30 32  1  0
 32 33  2  0
 22 23  1  0
 33 27  1  0
 34  5  1  0
 14  7  1  0
 16 15  1  0
 18 17  1  0
 24 49  1  0
 23 48  1  6
  6 39  1  6
  4 38  1  0
  3 37  1  0
  1 36  1  0
 35 57  1  0
 34 56  1  0
  9 40  1  0
 10 41  1  0
 12 42  1  0
 13 43  1  0
 15 44  1  6
 26 50  1  1
 21 47  1  0
 20 46  1  0
 18 45  1  0
 28 51  1  0
 29 52  1  0
 31 53  1  0
 32 54  1  0
 33 55  1  0
M  END


  Mrv1652309122215362D          

 35 40  0  0  1  0            999 V2000
    2.7333   -3.7688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3643   -3.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5408   -2.9814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1719   -2.2435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6265   -1.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2575   -0.8171    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7623   -0.1645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5541   -0.3960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7496   -1.1975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1505    0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9550    0.9756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5514    1.5456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1632    1.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5668    0.6370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8183    0.9838    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0804    0.6149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4986    1.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2970    0.9952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5166    0.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3151   -0.0075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9377   -0.3878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0913   -0.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4326   -0.8294    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0857   -1.5779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1184    1.9349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6954    1.7996    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2832    2.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0757    3.1770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6635    3.7560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4588    3.5364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0465    4.1153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6662    2.7379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0784    2.1590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4500   -1.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8189   -2.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 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
 16 22  1  0  0  0  0
 22 23  1  0  0  0  0
  6 23  1  0  0  0  0
 23 24  1  1  0  0  0
 17 25  1  0  0  0  0
 25 26  1  0  0  0  0
 15 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  2  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
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 27 33  1  0  0  0  0
  5 34  1  0  0  0  0
 34 35  2  0  0  0  0
  2 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0329322

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1[C@@H](C2=CC=C(O)C=C2)C2=C(O)C=C(O)C=C2[C@H]2[C@@H](OC3=C2C1=CC(O)=C3)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H22O7/c29-15-5-1-13(2-6-15)23-24-19(9-17(31)11-21(24)33)26-25-20(27(23)34)10-18(32)12-22(25)35-28(26)14-3-7-16(30)8-4-14/h1-12,23,26-34H/t23-,26+,27-,28-/m0/s1

> <INCHI_KEY>
LHUHHURKGTUZHU-OSPRVTPDSA-N

> <FORMULA>
C28H22O7

> <MOLECULAR_WEIGHT>
470.477

> <EXACT_MASS>
470.136553048

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
49.27136185744613

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,8S,9R,16R)-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0^{2,7}.0^{14,17}]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,9,12-tetrol

> <JCHEM_LOGP>
4.451736042666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.309899585907157

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.861995105052412

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2946465992189786

> <JCHEM_POLAR_SURFACE_AREA>
130.61

> <JCHEM_REFRACTIVITY>
128.947

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,8S,9R,16R)-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0^{2,7}.0^{14,17}]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,9,12-tetrol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  O   UNK     0       5.102  -7.035   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.413  -5.658   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.876  -5.565   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.188  -4.188   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.036  -2.903   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.347  -1.525   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.290  -0.307   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.768  -0.739   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.133  -2.235   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.881   0.325   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.516   1.821   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.629   2.885   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.038   2.253   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.925   1.189   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.527   1.837   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.150   1.148   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.931   2.245   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.421   1.858   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.831   0.373   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.322  -0.014   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.750  -0.724   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.170  -0.358   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.808  -1.548   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.160  -2.945   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -0.221   3.612   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.298   3.359   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.395   4.440   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.008   5.930   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.105   7.011   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.590   6.601   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.687   7.682   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.977   5.111   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.880   4.030   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.573  -2.995   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.262  -4.372   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   35                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   34                                                  
CONECT    6    5    7   23                                                  
CONECT    7    6    8   14                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    7   15                                                  
CONECT   15   14   16   26                                                  
CONECT   16   15   17   22                                                  
CONECT   17   16   18   25                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   16   23                                                  
CONECT   23   22    6   24                                                  
CONECT   24   23                                                            
CONECT   25   17   26                                                       
CONECT   26   25   15   27                                                  
CONECT   27   26   28   33                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   27                                                       
CONECT   34    5   35                                                       
CONECT   35   34    2                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₂₂O₇

Average Mass

470.4770 Da

Monoisotopic Mass

470.13655 Da

IUPAC Name

(1R,8S,9R,16R)-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0^{2,7}.0^{14,17}]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,9,12-tetrol

Traditional Name

(1R,8S,9R,16R)-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0^{2,7}.0^{14,17}]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,9,12-tetrol

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@@H](C2=CC=C(O)C=C2)C2=C(O)C=C(O)C=C2[C@H]2[C@@H](OC3=C2C1=CC(O)=C3)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C28H22O7/c29-15-5-1-13(2-6-15)23-24-19(9-17(31)11-21(24)33)26-25-20(27(23)34)10-18(32)12-22(25)35-28(26)14-3-7-16(30)8-4-14/h1-12,23,26-34H/t23-,26+,27-,28-/m0/s1

InChI Key

LHUHHURKGTUZHU-OSPRVTPDSA-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
Shorea hemsleyana	LOTUS Database	35616633

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
Dibenzocycloheptene
Coumaran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Secondary alcohol
Polyol
Organoheterocyclic compound
Ether
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Alcohol
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	4.45	ChemAxon
pKa (Strongest Acidic)	8.86	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	130.61 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	128.95 m³·mol⁻¹	ChemAxon
Polarizability	49.27 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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

C00033018

Chemspider ID

8989518

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10814213

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,8s,9r,16r)-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0²,⁷.0¹⁴,¹⁷]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,9,12-tetrol (NP0329322)

MOL for NP0329322 ((1r,8s,9r,16r)-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0²,⁷.0¹⁴,¹⁷]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,9,12-tetrol)

3D MOL for NP0329322 ((1r,8s,9r,16r)-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0²,⁷.0¹⁴,¹⁷]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,9,12-tetrol)

3D SDF for NP0329322 ((1r,8s,9r,16r)-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0²,⁷.0¹⁴,¹⁷]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,9,12-tetrol)

3D-SDF for NP0329322 ((1r,8s,9r,16r)-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0²,⁷.0¹⁴,¹⁷]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,9,12-tetrol)

PDB for NP0329322 ((1r,8s,9r,16r)-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0²,⁷.0¹⁴,¹⁷]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,9,12-tetrol)

3D PDB for NP0329322 ((1r,8s,9r,16r)-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0²,⁷.0¹⁴,¹⁷]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,9,12-tetrol)

SMILES for NP0329322 ((1r,8s,9r,16r)-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0²,⁷.0¹⁴,¹⁷]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,9,12-tetrol)

INCHI for NP0329322 ((1r,8s,9r,16r)-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0²,⁷.0¹⁴,¹⁷]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,9,12-tetrol)

Structure for NP0329322 ((1r,8s,9r,16r)-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0²,⁷.0¹⁴,¹⁷]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,9,12-tetrol)

3D Structure for NP0329322 ((1r,8s,9r,16r)-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0²,⁷.0¹⁴,¹⁷]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,9,12-tetrol)