NP-MRD: Showing NP-Card for methyl 2-[12,14-bis(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-18-yl]-2-hydroxyacetate (NP0263640)

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Record Information

Version

2.0

Created at

2022-09-08 06:53:03 UTC

Updated at

2022-09-08 06:53:03 UTC

NP-MRD ID

NP0263640

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-[12,14-bis(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-18-yl]-2-hydroxyacetate

Description

Methyl 2-[12,14-bis(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]Octadecan-18-yl]-2-hydroxyacetate belongs to the class of organic compounds known as phenanthrols. Phenanthrols are compounds containing a phenanthrene (or its hydrogenated derivative) to which a hydroxyl group is attached. methyl 2-[12,14-bis(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-18-yl]-2-hydroxyacetate is found in Xylocarpus granatum. Methyl 2-[12,14-bis(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]Octadecan-18-yl]-2-hydroxyacetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261500472D          

 43 48  0  0  0  0            999 V2000
   -3.5322    0.8892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7612    1.1828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1214    0.6620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2525   -0.1525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3504    0.9557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2193    1.7702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7106    0.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6234   -0.3973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4104   -0.6449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2127    0.4308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3742   -0.1959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1890   -0.0668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6184   -0.9649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1964   -1.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5251   -1.9260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3448   -2.0196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6736   -2.7763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8357   -1.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4677   -0.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9523   -1.5565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6163   -2.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1009   -2.9777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7958   -2.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7991   -0.1147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3099   -0.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6123    0.0242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1392   -0.6106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9524   -0.4717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4793   -1.1065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2387    0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7118    0.9368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9981    1.7106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5405    2.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0519    3.0444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8256    2.7580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7924    1.9337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8986    0.7979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1849    1.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3717    1.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5585    1.2938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2721    0.5201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3692    0.5431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3385    1.3676    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  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
  8 14  1  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
 13 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 32 36  1  0  0  0  0
 31 37  1  0  0  0  0
 26 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 24 41  1  0  0  0  0
 41 42  1  0  0  0  0
  7 42  1  0  0  0  0
 11 42  1  0  0  0  0
 42 43  1  0  0  0  0
M  END

     RDKit          3D

 83 88  0  0  0  0  0  0  0  0999 V2000
    6.3612    2.4911   -0.8161 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0041    2.0806   -0.9466 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0313    2.4132   -0.0180 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3821    3.1053    0.9711 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6035    2.0119   -0.1078 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5298    1.2662   -1.3069 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1081    1.1491    0.9687 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6590    0.9025    1.1470 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2323    1.7158    2.3950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2589    1.1226    0.0120 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3354    2.1103    0.4888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5538    2.0325   -0.3939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1984    0.6943   -0.0760 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5987    0.6154    1.3979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5163    0.7413   -0.7979 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5703    1.5117   -0.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4968    1.0773    0.8465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2792    2.1422    1.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8638    3.1620    0.5336 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8614    2.8726   -0.2549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0497   -0.5074   -1.1392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2018   -1.3777   -1.7395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5989   -2.2637   -2.5725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7702   -1.3573   -1.4693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2764   -0.3901   -0.4222 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8475   -0.0158   -0.7242 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9403    0.4046   -2.0942 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0723   -1.2130   -0.7770 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3665   -2.3188   -1.4406 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0691   -2.8225   -2.6309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4727   -4.0430   -3.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9873   -2.1464   -3.1331 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8584   -1.4548    0.4752 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3507   -1.2569    0.1858 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0951   -2.4305    0.5485 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8588   -3.1197   -0.3692 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5926   -4.3204    0.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8880   -2.6934   -1.5381 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7711   -0.1957    1.1379 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2179   -0.1740    1.4667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9360   -0.6732    2.3604 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5929   -0.5173    1.6049 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3930   -0.8427    2.4851 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.8612    2.2114   -1.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4337    3.5757   -0.5971 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9546    2.8936   -0.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1484    1.6356   -1.9879 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5169    1.6872    1.9032 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1319    1.7893    3.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5186    1.1995    2.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0427    2.7690    2.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3309    1.7657   -0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9859    3.1607    0.4379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6736    1.9367    1.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3354    2.0961   -1.4596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2253    2.8666   -0.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7840    0.3665    2.0701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2288    1.4510    1.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2679   -0.3000    1.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3963    1.2866   -1.7882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5970    0.0779    1.2334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0959    2.0854    1.9384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3540    3.5614   -0.9082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5522   -2.4402   -1.1971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2695   -1.2049   -2.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1941   -1.0586    0.4929 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8705   -0.8370   -1.5146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6061   -4.8071   -2.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2301   -4.4242   -4.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7551   -2.4706    0.8856 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5471   -4.0443    0.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7737   -5.0181   -0.7346 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0044   -4.8899    0.8675 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8511   -0.1756    0.5613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4444   -1.1762    1.9535 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4821    0.6501    2.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0313   -0.0202    3.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1457   -1.7242    2.5788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1071   -1.5093    3.1358 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  1  0
  5  7  1  0
  7 39  1  0
 39 40  1  1
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 15 16  1  0
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 34 39  1  0
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 17 16  1  0
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  1 44  1  0
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  5 47  1  6
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 40 78  1  0
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 20 64  1  0
 18 63  1  0
 17 62  1  0
  9 50  1  0
  9 51  1  0
  9 52  1  0
M  END


  Mrv1533004261500472D          

 43 48  0  0  0  0            999 V2000
   -3.5322    0.8892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7612    1.1828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1214    0.6620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2525   -0.1525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3504    0.9557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2193    1.7702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7106    0.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6234   -0.3973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4104   -0.6449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2127    0.4308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3742   -0.1959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1890   -0.0668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6184   -0.9649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1964   -1.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5251   -1.9260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3448   -2.0196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6736   -2.7763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8357   -1.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4677   -0.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9523   -1.5565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6163   -2.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1009   -2.9777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7958   -2.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7991   -0.1147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3099   -0.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6123    0.0242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1392   -0.6106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9524   -0.4717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4793   -1.1065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2387    0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7118    0.9368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9981    1.7106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5405    2.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0519    3.0444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8256    2.7580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7924    1.9337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8986    0.7979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1849    1.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3717    1.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5585    1.2938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2721    0.5201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3692    0.5431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3385    1.3676    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  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
  8 14  1  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
 13 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 32 36  1  0  0  0  0
 31 37  1  0  0  0  0
 26 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 24 41  1  0  0  0  0
 41 42  1  0  0  0  0
  7 42  1  0  0  0  0
 11 42  1  0  0  0  0
 42 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0263640

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C(O)C1C2(C)CC3(O)C(C2OC(C)=O)C(OC(C)=O)C2(O)C(CCC4(C)C(OC(=O)CC24)C2=COC=C2)C13C

> <INCHI_IDENTIFIER>
InChI=1S/C31H40O12/c1-14(32)41-24-20-25(42-15(2)33)31(38)17(29(5)22(21(35)26(36)39-6)28(24,4)13-30(20,29)37)7-9-27(3)18(31)11-19(34)43-23(27)16-8-10-40-12-16/h8,10,12,17-18,20-25,35,37-38H,7,9,11,13H2,1-6H3

> <INCHI_KEY>
CBZCSQUNKXXZJV-UHFFFAOYSA-N

> <FORMULA>
C31H40O12

> <MOLECULAR_WEIGHT>
604.649

> <EXACT_MASS>
604.251976728

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
60.838274995196635

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-[12,14-bis(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-18-yl]-2-hydroxyacetate

> <ALOGPS_LOGP>
1.86

> <JCHEM_LOGP>
0.19683240466666496

> <ALOGPS_LOGS>
-3.37

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.311493040902157

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.369927032802867

> <JCHEM_PKA_STRONGEST_BASIC>
-2.888716676858349

> <JCHEM_POLAR_SURFACE_AREA>
179.02999999999997

> <JCHEM_REFRACTIVITY>
143.2595

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.60e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-[12,14-bis(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-18-yl]-2-hydroxyacetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0      -6.593   1.660   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.154   2.208   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.960   1.236   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -4.205  -0.285   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.521   1.784   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.276   3.304   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.326   0.812   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.164  -0.742   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.633  -1.204   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.397   0.804   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.698  -0.366   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.220  -0.125   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.154  -1.801   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.367  -2.183   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.980  -3.595   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.510  -3.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.124  -5.182   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -3.427  -2.532   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.740  -1.659   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.644  -2.905   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.017  -4.312   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.922  -5.558   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.485  -4.472   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.358  -0.214   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.312  -1.423   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.876   0.045   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.860  -1.140   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.378  -0.881   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.361  -2.066   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       7.912   0.564   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.929   1.749   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.463   3.193   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.609   4.474   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       7.563   5.683   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       9.008   5.148   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.946   3.610   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.411   1.489   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.945   2.934   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.427   2.674   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       2.909   2.415   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       2.375   0.971   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       0.689   1.014   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       0.632   2.553   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    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   42                                                  
CONECT    8    7    9   10   14                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13   42                                             
CONECT   12   11                                                            
CONECT   13   11   14   19                                                  
CONECT   14   13    8   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   13   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   19   25   26   41                                             
CONECT   25   24                                                            
CONECT   26   24   27   37                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32   37                                                  
CONECT   32   31   33   36                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   32                                                       
CONECT   37   31   26   38   39                                             
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   24   42                                                  
CONECT   42   41    7   11   43                                             
CONECT   43   42                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   96    0
END

View in JSmol

Synonyms

Value	Source
Methyl 2-[12,14-bis(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0,.0,.0,]octadecan-18-yl]-2-hydroxyacetic acid	Generator
Methyl 2-[12,14-bis(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-18-yl]-2-hydroxyacetic acid	Generator

Chemical Formula

C₃₁H₄₀O₁₂

Average Mass

604.6490 Da

Monoisotopic Mass

604.25198 Da

IUPAC Name

methyl 2-[12,14-bis(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-18-yl]-2-hydroxyacetate

Traditional Name

methyl 2-[12,14-bis(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-18-yl]-2-hydroxyacetate

CAS Registry Number

Not Available

SMILES

COC(=O)C(O)C1C2(C)CC3(O)C(C2OC(C)=O)C(OC(C)=O)C2(O)C(CCC4(C)C(OC(=O)CC24)C2=COC=C2)C13C

InChI Identifier

InChI=1S/C31H40O12/c1-14(32)41-24-20-25(42-15(2)33)31(38)17(29(5)22(21(35)26(36)39-6)28(24,4)13-30(20,29)37)7-9-27(3)18(31)11-19(34)43-23(27)16-8-10-40-12-16/h8,10,12,17-18,20-25,35,37-38H,7,9,11,13H2,1-6H3

InChI Key

CBZCSQUNKXXZJV-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
Xylocarpus granatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrols. Phenanthrols are compounds containing a phenanthrene (or its hydrogenated derivative) to which a hydroxyl group is attached.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Phenanthrols

Direct Parent

Phenanthrols

Alternative Parents

Substituents

Phenanthrol
1-naphthol
2-naphthol
Naphthalene
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	1.86	ALOGPS
logP	0.2	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	12.37	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	179.03 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	143.26 m³·mol⁻¹	ChemAxon
Polarizability	60.84 Å³	ChemAxon
Number of Rings	6	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 2-[12,14-bis(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-18-yl]-2-hydroxyacetate (NP0263640)

MOL for NP0263640 (methyl 2-[12,14-bis(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-18-yl]-2-hydroxyacetate)

3D MOL for NP0263640 (methyl 2-[12,14-bis(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-18-yl]-2-hydroxyacetate)

3D SDF for NP0263640 (methyl 2-[12,14-bis(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-18-yl]-2-hydroxyacetate)

3D-SDF for NP0263640 (methyl 2-[12,14-bis(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-18-yl]-2-hydroxyacetate)

PDB for NP0263640 (methyl 2-[12,14-bis(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-18-yl]-2-hydroxyacetate)

3D PDB for NP0263640 (methyl 2-[12,14-bis(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-18-yl]-2-hydroxyacetate)

SMILES for NP0263640 (methyl 2-[12,14-bis(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-18-yl]-2-hydroxyacetate)

INCHI for NP0263640 (methyl 2-[12,14-bis(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-18-yl]-2-hydroxyacetate)

Structure for NP0263640 (methyl 2-[12,14-bis(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-18-yl]-2-hydroxyacetate)

3D Structure for NP0263640 (methyl 2-[12,14-bis(acetyloxy)-6-(furan-3-yl)-11,17-dihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-18-yl]-2-hydroxyacetate)