NP-MRD: Showing NP-Card for 12-(2,3-dihydroxy-3-methylbutyl)-5,8,9-trihydroxy-7-(4-hydroxy-3-methylbut-2-en-1-yl)-2,2-dimethyl-1,11-dioxatetracen-6-one (NP0201799)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 20:54:15 UTC

Updated at

2022-09-04 20:54:15 UTC

NP-MRD ID

NP0201799

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12-(2,3-dihydroxy-3-methylbutyl)-5,8,9-trihydroxy-7-(4-hydroxy-3-methylbut-2-en-1-yl)-2,2-dimethyl-1,11-dioxatetracen-6-one

Description

12-(2,3-Dihydroxy-3-methylbutyl)-5,8,9-trihydroxy-7-(4-hydroxy-3-methylbut-2-en-1-yl)-2,2-dimethyl-2,6-dihydro-1,11-dioxatetracen-6-one belongs to the class of organic compounds known as 8-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 8-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone group. 12-(2,3-dihydroxy-3-methylbutyl)-5,8,9-trihydroxy-7-(4-hydroxy-3-methylbut-2-en-1-yl)-2,2-dimethyl-1,11-dioxatetracen-6-one is found in Garcinia xipshuanbannaensis. 12-(2,3-Dihydroxy-3-methylbutyl)-5,8,9-trihydroxy-7-(4-hydroxy-3-methylbut-2-en-1-yl)-2,2-dimethyl-2,6-dihydro-1,11-dioxatetracen-6-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161513272D          

 37 40  0  0  0  0            999 V2000
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   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   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    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
    7.1447   -1.6500    0.0000 O   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
    6.4302    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6052   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2552   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1413   -2.1123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6716   -3.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 O   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  4  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  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  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 14 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 22 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 13 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
  5 35  1  0  0  0  0
 11 35  2  0  0  0  0
  2 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END

     RDKit          3D

 69 72  0  0  0  0  0  0  0  0999 V2000
    7.4791   -0.9955   -0.9211 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2679   -1.9020   -0.5521 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1931   -1.7483   -1.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9937   -1.5821   -1.9288 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3362   -0.2815   -1.7965 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9321    0.8163   -2.4442 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1524    0.7476   -3.0798 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2752    2.0209   -2.4481 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8565    3.1325   -3.0941 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0540    2.1468   -1.8272 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4480    1.0812   -1.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2761    1.2169   -0.5934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3410    0.2349    0.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5750    0.4242    0.6334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2116    1.7497    0.5157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2906    1.7712   -0.5505 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2570    0.8394   -0.1964 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9305    3.1399   -0.5339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9938    4.2123   -0.9884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1662    3.1862   -1.4077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3850    3.3695    0.7842 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2276   -0.6052    1.2955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6512   -1.8518    1.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4064   -2.0527    0.7636 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1200   -3.2840    0.8587 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2317   -1.0188    0.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4646   -1.1687   -0.5100 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9904   -2.2967   -0.4441 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1162   -0.1472   -1.1734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3449   -2.9238    2.0633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5125   -2.7679    2.6346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1826   -1.4339    2.5840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5078   -1.7155    1.8357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5239   -1.0581    3.9969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4554   -0.4550    1.9065 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6013   -2.8292    0.5469 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9702   -2.0869    1.6934 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0094   -0.0135   -1.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1681   -0.9336   -0.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0027   -1.4331   -1.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6276   -2.7412   -0.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3830   -1.6049   -3.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3007   -2.4357   -1.9277 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6620   -0.1130   -3.0840 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7596    3.0274   -3.5521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5254    3.1004   -1.8335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4781    2.5379    0.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6652    2.0433    1.4651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8793    1.5794   -1.5584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9389    1.3136    0.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9689    3.8581   -1.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3762    4.7444   -1.8938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9628    5.0019   -0.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3118    4.2072   -1.8375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0372    2.4789   -2.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0778    2.9947   -0.8089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4061    4.3630    0.9482 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8670   -3.8116    0.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8462   -3.9064    2.1077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0186   -3.6076    3.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2006   -0.8768    1.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8707   -2.6730    2.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1825   -1.9326    0.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5987   -1.3492    4.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9623   -1.6812    4.7422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3671    0.0132    4.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5340   -3.4131    0.2903 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7853   -3.4867    0.8572 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7285   -1.1350    1.6105 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 36  1  0
 36 37  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 29  2  0
 29 27  1  0
 27 28  2  0
 27 26  1  0
 26 24  2  0
 24 25  1  0
 24 23  1  0
 23 22  2  0
 22 35  1  0
 35 32  1  0
 32 33  1  0
 32 34  1  0
 32 31  1  0
 31 30  2  0
 22 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 14 13  2  0
 13 12  1  0
 29  5  1  0
 13 26  1  0
 12 11  1  0
 30 23  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
 36 67  1  0
 36 68  1  0
 37 69  1  0
  3 41  1  0
  4 42  1  0
  4 43  1  0
  7 44  1  0
  9 45  1  0
 10 46  1  0
 25 58  1  0
 33 61  1  0
 33 62  1  0
 33 63  1  0
 34 64  1  0
 34 65  1  0
 34 66  1  0
 31 60  1  0
 30 59  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  6
 17 50  1  0
 19 51  1  0
 19 52  1  0
 19 53  1  0
 20 54  1  0
 20 55  1  0
 20 56  1  0
 21 57  1  0
M  END


  Mrv1533004161513272D          

 37 40  0  0  0  0            999 V2000
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   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   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    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
    7.1447   -1.6500    0.0000 O   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
    6.4302    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6052   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2552   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1413   -2.1123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6716   -3.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 O   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  4  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  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  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 14 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 22 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 13 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
  5 35  1  0  0  0  0
 11 35  2  0  0  0  0
  2 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0201799

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CO)=CCC1=C(O)C(O)=CC2=C1C(=O)C1=C(O)C3=C(OC(C)(C)C=C3)C(CC(O)C(C)(C)O)=C1O2

> <INCHI_IDENTIFIER>
InChI=1S/C28H32O9/c1-13(12-29)6-7-14-20-18(11-17(30)22(14)32)36-26-16(10-19(31)28(4,5)35)25-15(8-9-27(2,3)37-25)23(33)21(26)24(20)34/h6,8-9,11,19,29-33,35H,7,10,12H2,1-5H3

> <INCHI_KEY>
WCAZWPKNYZBYGB-UHFFFAOYSA-N

> <FORMULA>
C28H32O9

> <MOLECULAR_WEIGHT>
512.555

> <EXACT_MASS>
512.20463261

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
54.557941669260494

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
12-(2,3-dihydroxy-3-methylbutyl)-5,8,9-trihydroxy-7-(4-hydroxy-3-methylbut-2-en-1-yl)-2,2-dimethyl-2,6-dihydro-1,11-dioxatetracen-6-one

> <ALOGPS_LOGP>
3.05

> <JCHEM_LOGP>
3.6354916886666646

> <ALOGPS_LOGS>
-4.39

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.620313858110473

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.450585234987334

> <JCHEM_PKA_STRONGEST_BASIC>
-2.725805083890249

> <JCHEM_POLAR_SURFACE_AREA>
156.91

> <JCHEM_REFRACTIVITY>
139.7603

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.08e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-(2,3-dihydroxy-3-methylbutyl)-5,8,9-trihydroxy-7-(4-hydroxy-3-methylbut-2-en-1-yl)-2,2-dimethyl-1,11-dioxatetracen-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.003   0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.463  -0.770   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      13.543  -0.770   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      13.337  -4.620   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.197  -3.943   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      16.187  -5.657   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      10.669  -9.240   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       9.336 -11.550   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   36                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   35                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   35                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   32                                                  
CONECT   14   13   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18                                                            
CONECT   22   14   23   29                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   22   30                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   13   33                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    5   11                                                  
CONECT   36    2   37                                                       
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₂O₉

Average Mass

512.5550 Da

Monoisotopic Mass

512.20463 Da

IUPAC Name

12-(2,3-dihydroxy-3-methylbutyl)-5,8,9-trihydroxy-7-(4-hydroxy-3-methylbut-2-en-1-yl)-2,2-dimethyl-2,6-dihydro-1,11-dioxatetracen-6-one

Traditional Name

12-(2,3-dihydroxy-3-methylbutyl)-5,8,9-trihydroxy-7-(4-hydroxy-3-methylbut-2-en-1-yl)-2,2-dimethyl-1,11-dioxatetracen-6-one

CAS Registry Number

Not Available

SMILES

CC(CO)=CCC1=C(O)C(O)=CC2=C1C(=O)C1=C(O)C3=C(OC(C)(C)C=C3)C(CC(O)C(C)(C)O)=C1O2

InChI Identifier

InChI=1S/C28H32O9/c1-13(12-29)6-7-14-20-18(11-17(30)22(14)32)36-26-16(10-19(31)28(4,5)35)25-15(8-9-27(2,3)37-25)23(33)21(26)24(20)34/h6,8-9,11,19,29-33,35H,7,10,12H2,1-5H3

InChI Key

WCAZWPKNYZBYGB-UHFFFAOYSA-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
Garcinia xipshuanbannaensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 8-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

8-prenylated xanthones

Alternative Parents

Substituents

4-prenylated xanthone
8-prenylated xanthone
Pyranoxanthone
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Pyran
Benzenoid
Tertiary alcohol
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Polyol
Ether
Oxacycle
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Primary alcohol
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	3.05	ALOGPS
logP	3.64	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	7.45	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	139.76 m³·mol⁻¹	ChemAxon
Polarizability	54.56 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

74423457

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 12-(2,3-dihydroxy-3-methylbutyl)-5,8,9-trihydroxy-7-(4-hydroxy-3-methylbut-2-en-1-yl)-2,2-dimethyl-1,11-dioxatetracen-6-one (NP0201799)

MOL for NP0201799 (12-(2,3-dihydroxy-3-methylbutyl)-5,8,9-trihydroxy-7-(4-hydroxy-3-methylbut-2-en-1-yl)-2,2-dimethyl-1,11-dioxatetracen-6-one)

3D MOL for NP0201799 (12-(2,3-dihydroxy-3-methylbutyl)-5,8,9-trihydroxy-7-(4-hydroxy-3-methylbut-2-en-1-yl)-2,2-dimethyl-1,11-dioxatetracen-6-one)

3D SDF for NP0201799 (12-(2,3-dihydroxy-3-methylbutyl)-5,8,9-trihydroxy-7-(4-hydroxy-3-methylbut-2-en-1-yl)-2,2-dimethyl-1,11-dioxatetracen-6-one)

3D-SDF for NP0201799 (12-(2,3-dihydroxy-3-methylbutyl)-5,8,9-trihydroxy-7-(4-hydroxy-3-methylbut-2-en-1-yl)-2,2-dimethyl-1,11-dioxatetracen-6-one)

PDB for NP0201799 (12-(2,3-dihydroxy-3-methylbutyl)-5,8,9-trihydroxy-7-(4-hydroxy-3-methylbut-2-en-1-yl)-2,2-dimethyl-1,11-dioxatetracen-6-one)

3D PDB for NP0201799 (12-(2,3-dihydroxy-3-methylbutyl)-5,8,9-trihydroxy-7-(4-hydroxy-3-methylbut-2-en-1-yl)-2,2-dimethyl-1,11-dioxatetracen-6-one)

SMILES for NP0201799 (12-(2,3-dihydroxy-3-methylbutyl)-5,8,9-trihydroxy-7-(4-hydroxy-3-methylbut-2-en-1-yl)-2,2-dimethyl-1,11-dioxatetracen-6-one)

INCHI for NP0201799 (12-(2,3-dihydroxy-3-methylbutyl)-5,8,9-trihydroxy-7-(4-hydroxy-3-methylbut-2-en-1-yl)-2,2-dimethyl-1,11-dioxatetracen-6-one)

Structure for NP0201799 (12-(2,3-dihydroxy-3-methylbutyl)-5,8,9-trihydroxy-7-(4-hydroxy-3-methylbut-2-en-1-yl)-2,2-dimethyl-1,11-dioxatetracen-6-one)

3D Structure for NP0201799 (12-(2,3-dihydroxy-3-methylbutyl)-5,8,9-trihydroxy-7-(4-hydroxy-3-methylbut-2-en-1-yl)-2,2-dimethyl-1,11-dioxatetracen-6-one)