NP-MRD: Showing NP-Card for methyl 8-hydroxy-3-methoxy-6-methyl-9-oxo-5-{2-oxo-2-[2,3,5-trihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-yl]ethyl}-7-(2-oxopropyl)xanthene-1-carboxylate (NP0245138)

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Record Information

Version

1.0

Created at

2022-09-07 06:06:37 UTC

Updated at

2022-09-07 06:06:38 UTC

NP-MRD ID

NP0245138

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 8-hydroxy-3-methoxy-6-methyl-9-oxo-5-{2-oxo-2-[2,3,5-trihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-yl]ethyl}-7-(2-oxopropyl)xanthene-1-carboxylate

Description

Methyl 8-hydroxy-3-methoxy-6-methyl-9-oxo-5-{2-oxo-2-[2,3,5-trihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]Heptan-3-yl]ethyl}-7-(2-oxopropyl)-9H-xanthene-1-carboxylate belongs to the class of organic compounds known as 4-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 4-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. methyl 8-hydroxy-3-methoxy-6-methyl-9-oxo-5-{2-oxo-2-[2,3,5-trihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-yl]ethyl}-7-(2-oxopropyl)xanthene-1-carboxylate is found in Pestalotiopsis fici. Methyl 8-hydroxy-3-methoxy-6-methyl-9-oxo-5-{2-oxo-2-[2,3,5-trihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]Heptan-3-yl]ethyl}-7-(2-oxopropyl)-9H-xanthene-1-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251508492D          

 45 49  0  0  0  0            999 V2000
    1.4289   -4.9500    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   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -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 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    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
    2.1434   -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
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0993    0.6817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4744    0.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9441    1.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1316    1.1705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2262    2.0890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5084    2.8642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0387    2.2322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6707    2.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5274    3.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1594    4.1053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0161    4.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9347    3.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5690    1.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3815    1.7435    0.0000 O   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
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1447   -1.6500    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
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -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
    3.5724   -3.7125    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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
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 11 12  1  0  0  0  0
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 25 31  1  0  0  0  0
 18 31  1  0  0  0  0
 31 32  1  0  0  0  0
 14 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 35 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  2  0  0  0  0
 13 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 43 45  1  0  0  0  0
  5 45  1  0  0  0  0
 11 45  2  0  0  0  0
M  END

     RDKit          3D

 81 85  0  0  0  0  0  0  0  0999 V2000
   -8.6049   -2.3570   -0.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3960   -2.2152   -0.7292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4774   -1.2287   -0.2532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8534   -0.6199    0.7338 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2362   -1.0626   -0.9764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1809   -1.4855   -2.3220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0783   -1.3038   -3.1128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0843   -1.7482   -4.4477 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0164   -1.6082   -5.3305 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4903   -2.7667   -0.9315 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9552   -0.7083    0.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3657   -1.0662   -0.1773 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2490   -0.3673   -0.8492 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9980    0.9624   -1.4777 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6356   -0.9618   -0.9909 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5505   -1.4565    0.1100 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.6222    1.8325    2.2156 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4422    3.3967    4.6274 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8496    0.9455    3.5118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9377    0.6076    1.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0676   -0.0092    0.8370 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1655    1.1236   -1.6771 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8377   -1.8945    1.9888 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3151    3.2874    3.4935 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2903    1.8408    3.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6228    2.2481    4.9455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1411    1.3793    5.1223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5810    3.4429    4.9183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6834    4.4838    6.0353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7121    2.7225    6.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7352    0.6060    3.5684 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
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  8  9  1  0
  7 10  2  0
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 31 71  1  1
 32 72  1  0
M  END


  Mrv1533004251508492D          

 45 49  0  0  0  0            999 V2000
    1.4289   -4.9500    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   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -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 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    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
    2.1434   -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
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0993    0.6817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4744    0.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9441    1.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1316    1.1705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2262    2.0890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5084    2.8642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0387    2.2322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6707    2.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5274    3.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1594    4.1053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0161    4.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9347    3.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5690    1.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3815    1.7435    0.0000 O   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
    5.7158   -2.4750    0.0000 C   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 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
    7.8592   -2.8875    0.0000 C   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
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -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
    3.5724   -3.7125    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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 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  2  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
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 25 31  1  0  0  0  0
 18 31  1  0  0  0  0
 31 32  1  0  0  0  0
 14 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 35 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  2  0  0  0  0
 13 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 43 45  1  0  0  0  0
  5 45  1  0  0  0  0
 11 45  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0245138

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CC(OC)=CC2=C1C(=O)C1=C(O)C(CC(C)=O)=C(C)C(CC(=O)C3(O)CC(O)C4OC4(CC=C(C)C)C3O)=C1O2

> <INCHI_IDENTIFIER>
InChI=1S/C33H36O12/c1-14(2)7-8-33-29(45-33)21(35)13-32(41,31(33)40)23(36)12-19-16(4)18(9-15(3)34)26(37)25-27(38)24-20(30(39)43-6)10-17(42-5)11-22(24)44-28(19)25/h7,10-11,21,29,31,35,37,40-41H,8-9,12-13H2,1-6H3

> <INCHI_KEY>
FYULFHVQQBWSCF-UHFFFAOYSA-N

> <FORMULA>
C33H36O12

> <MOLECULAR_WEIGHT>
624.639

> <EXACT_MASS>
624.220676599

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
63.81061558103722

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 8-hydroxy-3-methoxy-6-methyl-9-oxo-5-{2-oxo-2-[2,3,5-trihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-yl]ethyl}-7-(2-oxopropyl)-9H-xanthene-1-carboxylate

> <ALOGPS_LOGP>
1.93

> <JCHEM_LOGP>
3.173190391666666

> <ALOGPS_LOGS>
-3.90

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.63561997395291

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.253322053150784

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2428811174882846

> <JCHEM_POLAR_SURFACE_AREA>
189.42

> <JCHEM_REFRACTIVITY>
160.45560000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.89e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 8-hydroxy-3-methoxy-6-methyl-9-oxo-5-{2-oxo-2-[2,3,5-trihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-yl]ethyl}-7-(2-oxopropyl)xanthene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.519   1.273   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.485   1.273   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.496   2.452   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.979   2.185   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.022   3.899   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.549   5.347   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.539   4.167   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.719   5.157   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.451   6.673   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.631   7.663   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.363   9.180   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.078   7.137   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.529   2.987   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      10.045   3.255   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   45                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12   45                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   42                                                  
CONECT   14   13   15   33                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20   31                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23   25                                                       
CONECT   25   24   23   26   31                                             
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   25   18   32                                                  
CONECT   32   31                                                            
CONECT   33   14   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   40                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   35   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   13   43                                                  
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43    5   11                                                  
MASTER        0    0    0    0    0    0    0    0   45    0   98    0
END

View in JSmol

Synonyms

Value	Source
Methyl 8-hydroxy-3-methoxy-6-methyl-9-oxo-5-{2-oxo-2-[2,3,5-trihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-yl]ethyl}-7-(2-oxopropyl)-9H-xanthene-1-carboxylic acid	Generator

Chemical Formula

C₃₃H₃₆O₁₂

Average Mass

624.6390 Da

Monoisotopic Mass

624.22068 Da

IUPAC Name

methyl 8-hydroxy-3-methoxy-6-methyl-9-oxo-5-{2-oxo-2-[2,3,5-trihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-yl]ethyl}-7-(2-oxopropyl)-9H-xanthene-1-carboxylate

Traditional Name

methyl 8-hydroxy-3-methoxy-6-methyl-9-oxo-5-{2-oxo-2-[2,3,5-trihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-yl]ethyl}-7-(2-oxopropyl)xanthene-1-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CC(OC)=CC2=C1C(=O)C1=C(O)C(CC(C)=O)=C(C)C(CC(=O)C3(O)CC(O)C4OC4(CC=C(C)C)C3O)=C1O2

InChI Identifier

InChI=1S/C33H36O12/c1-14(2)7-8-33-29(45-33)21(35)13-32(41,31(33)40)23(36)12-19-16(4)18(9-15(3)34)26(37)25-27(38)24-20(30(39)43-6)10-17(42-5)11-22(24)44-28(19)25/h7,10-11,21,29,31,35,37,40-41H,8-9,12-13H2,1-6H3

InChI Key

FYULFHVQQBWSCF-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
Pestalotiopsis fici	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 4-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

4-prenylated xanthones

Alternative Parents

Substituents

4-prenylated xanthone
Chromone
M-methoxybenzoic acid or derivatives
Anisole
Alkyl aryl ether
Pyranone
Oxepane
Cyclitol or derivatives
Benzenoid
Pyran
Alpha-hydroxy ketone
Heteroaromatic compound
Vinylogous acid
Methyl ester
Tertiary alcohol
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Ketone
Ether
Oxirane
Dialkyl ether
Polyol
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
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	1.93	ALOGPS
logP	3.17	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	8.25	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	189.42 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	160.46 m³·mol⁻¹	ChemAxon
Polarizability	63.81 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	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

74819716

PDB ID

Not Available

ChEBI ID

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Good Scents ID

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References

General References

LOTUS database [Link]

Showing NP-Card for methyl 8-hydroxy-3-methoxy-6-methyl-9-oxo-5-{2-oxo-2-[2,3,5-trihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-yl]ethyl}-7-(2-oxopropyl)xanthene-1-carboxylate (NP0245138)

MOL for NP0245138 (methyl 8-hydroxy-3-methoxy-6-methyl-9-oxo-5-{2-oxo-2-[2,3,5-trihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-yl]ethyl}-7-(2-oxopropyl)xanthene-1-carboxylate)

3D MOL for NP0245138 (methyl 8-hydroxy-3-methoxy-6-methyl-9-oxo-5-{2-oxo-2-[2,3,5-trihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-yl]ethyl}-7-(2-oxopropyl)xanthene-1-carboxylate)

3D SDF for NP0245138 (methyl 8-hydroxy-3-methoxy-6-methyl-9-oxo-5-{2-oxo-2-[2,3,5-trihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-yl]ethyl}-7-(2-oxopropyl)xanthene-1-carboxylate)

3D-SDF for NP0245138 (methyl 8-hydroxy-3-methoxy-6-methyl-9-oxo-5-{2-oxo-2-[2,3,5-trihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-yl]ethyl}-7-(2-oxopropyl)xanthene-1-carboxylate)

PDB for NP0245138 (methyl 8-hydroxy-3-methoxy-6-methyl-9-oxo-5-{2-oxo-2-[2,3,5-trihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-yl]ethyl}-7-(2-oxopropyl)xanthene-1-carboxylate)

3D PDB for NP0245138 (methyl 8-hydroxy-3-methoxy-6-methyl-9-oxo-5-{2-oxo-2-[2,3,5-trihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-yl]ethyl}-7-(2-oxopropyl)xanthene-1-carboxylate)

SMILES for NP0245138 (methyl 8-hydroxy-3-methoxy-6-methyl-9-oxo-5-{2-oxo-2-[2,3,5-trihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-yl]ethyl}-7-(2-oxopropyl)xanthene-1-carboxylate)

INCHI for NP0245138 (methyl 8-hydroxy-3-methoxy-6-methyl-9-oxo-5-{2-oxo-2-[2,3,5-trihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-yl]ethyl}-7-(2-oxopropyl)xanthene-1-carboxylate)

Structure for NP0245138 (methyl 8-hydroxy-3-methoxy-6-methyl-9-oxo-5-{2-oxo-2-[2,3,5-trihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-yl]ethyl}-7-(2-oxopropyl)xanthene-1-carboxylate)

3D Structure for NP0245138 (methyl 8-hydroxy-3-methoxy-6-methyl-9-oxo-5-{2-oxo-2-[2,3,5-trihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-yl]ethyl}-7-(2-oxopropyl)xanthene-1-carboxylate)