NP-MRD: Showing NP-Card for methyl 3-{[4-(acetyloxy)-3-ethyl-4-methylpent-2-enoyl]oxy}-15,16-dihydroxy-9,13-dimethyl-4,10-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-11-ene-17-carboxylate (NP0142019)

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Record Information

Version

2.0

Created at

2022-09-01 20:28:06 UTC

Updated at

2022-09-01 20:28:06 UTC

NP-MRD ID

NP0142019

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 3-{[4-(acetyloxy)-3-ethyl-4-methylpent-2-enoyl]oxy}-15,16-dihydroxy-9,13-dimethyl-4,10-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-11-ene-17-carboxylate

Description

Methyl 3-{[4-(acetyloxy)-3-ethyl-4-methylpent-2-enoyl]oxy}-15,16-dihydroxy-9,13-dimethyl-4,10-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]Nonadec-11-ene-17-carboxylate belongs to the class of organic compounds known as naphthopyranone glycosides. Naphthopyranone glycosides are compounds containing a carbohydrate moiety glycosidically linked to a naphthopyranone moiety. methyl 3-{[4-(acetyloxy)-3-ethyl-4-methylpent-2-enoyl]oxy}-15,16-dihydroxy-9,13-dimethyl-4,10-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-11-ene-17-carboxylate is found in Brucea javanica. Methyl 3-{[4-(acetyloxy)-3-ethyl-4-methylpent-2-enoyl]oxy}-15,16-dihydroxy-9,13-dimethyl-4,10-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]Nonadec-11-ene-17-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161503202D          

 55 60  0  0  0  0            999 V2000
   -2.6777    2.6610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2025    1.9866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5489    1.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0737    0.5635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2520    0.6379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9056    1.3866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7768   -0.0365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0448    0.0378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5512   -0.7705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4626   -0.5022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8607    0.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0988   -0.5561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4551   -1.4252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0637   -2.0609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8313   -2.8525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8841   -1.8636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4491   -2.4647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1290   -1.0656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9696   -0.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7456   -1.6357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5384   -1.4393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3403   -1.2454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9091   -1.8430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7110   -1.6492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9441   -0.8578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7460   -0.6640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9791    0.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7810    0.3212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3148   -1.2616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1167   -1.0677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0817   -2.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6505   -2.6505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2798   -2.2468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0467   -3.0381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5734   -0.4541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3753   -0.2602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0046    0.1435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2377    0.9349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027   -0.0503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6008    0.5232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7643    0.3129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1747    0.9272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3471    0.7964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1680    1.4409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2367   -1.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9719   -1.5005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1932   -2.6986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8849   -3.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3705    1.1635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4449    1.9852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2962    0.3419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1922    1.0892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6674    1.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4890    1.6892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3210    2.5123    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
  4  5  1  4  0  0  0
  5  6  2  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
  9 10  1  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
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 24 33  1  0  0  0  0
 33 34  1  0  0  0  0
 22 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 19 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 10 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
  8 43  1  0  0  0  0
 43 44  2  0  0  0  0
 13 45  1  0  0  0  0
 45 46  2  0  0  0  0
 45 47  1  0  0  0  0
 47 48  1  0  0  0  0
  3 49  1  0  0  0  0
 49 50  1  0  0  0  0
 49 51  1  0  0  0  0
 49 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  2  0  0  0  0
 53 55  1  0  0  0  0
M  END

     RDKit          3D

105110  0  0  0  0  0  0  0  0999 V2000
   -6.9852   -2.1406    2.0696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6715   -1.1453    1.2625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0162   -0.3175    0.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8007   -0.2076   -0.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6278   -0.9239    0.2623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4649   -1.7712    1.1221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4108   -0.6320   -0.4324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2115   -1.3117   -0.1213 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0395   -2.3895   -1.1804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8671   -3.3232   -1.1586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0209   -2.3130   -2.1010 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1760   -1.7313   -1.6496 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2223   -1.6734   -2.7538 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4797   -1.4356   -1.9895 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7522   -1.6019   -2.7540 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6455   -2.8710   -3.5762 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8193   -1.7601   -1.6909 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8176   -2.4516   -1.9939 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5799   -1.0986   -0.4303 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5315   -1.2800    0.5881 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5232   -0.3389    0.9223 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2216   -0.8879    2.0090 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9901    0.1635    2.5116 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.4865   -0.0437    3.9024 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2374    1.1109    4.2280 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1672    0.3281    1.5868 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0015   -0.7791    1.5963 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7015    0.6815    0.2001 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.7162    0.3027   -0.6887 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4556   -0.0472   -0.2240 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.4984   -0.1312   -1.2475 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1813    0.8433   -2.2350 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1811    0.3932   -0.7821 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2127    0.8666    0.6585 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1671    1.9272    0.6756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0816    1.5754    0.9553 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0635    2.9212    0.6767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2943    0.9446    0.2788 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4084    1.2728    1.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4405    0.8151    2.3330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4357    2.1009    0.7380 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5110    2.4435    1.5997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4686    1.4341   -1.0063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0102    0.4883   -1.9166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0460   -0.3928   -1.0943 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9999   -0.5234    0.1114 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.0239    0.5561   -0.5378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7541   -0.4359   -1.4380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3098    1.6311   -1.2519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9708    1.0163    0.3751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8044    1.8038    1.4604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9588    2.1898    2.3266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6897    2.2318    1.7725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6213   -3.0563    1.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3283   -1.7720    2.8853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8436   -2.6166    2.7227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5129   -1.7058    0.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2098   -0.4514    1.9970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6126    0.5528   -0.9861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4385   -1.9366    0.7715 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6373   -2.3616   -0.8297 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0433   -0.7993   -3.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2781   -2.6312   -3.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5036   -2.2395   -1.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0107   -0.7850   -3.4268 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1121   -3.6301   -2.9603 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6747   -3.2602   -3.7256 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1259   -2.6185   -4.5197 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0213    0.5836    1.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3837    1.1056    2.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1885   -0.8935    3.9875 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6796   -0.2030    4.6477 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8900    1.8955    3.6976 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7753    1.1766    1.9998 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5195   -1.5276    2.0472 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6030    1.7825    0.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5719    0.7301   -0.5094 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7043   -1.0050   -0.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4813    0.0822    0.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7304    0.7788   -3.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2656    0.8002   -2.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0673    2.3158    1.5829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2089    1.4726    2.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6390    3.3844    1.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1986    3.1317    1.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0687    1.5765    1.9710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0587    3.0370    2.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7613   -0.0728   -2.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.7848    1.4443    2.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3230    3.2092    2.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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 54103  1  0
 54104  1  0
 54105  1  0
M  END


  Mrv1533004161503202D          

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    7.6505   -2.6505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5734   -0.4541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3753   -0.2602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
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 12 13  1  0  0  0  0
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 24 25  1  0  0  0  0
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 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 29  1  0  0  0  0
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 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 24 33  1  0  0  0  0
 33 34  1  0  0  0  0
 22 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 19 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 10 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
  8 43  1  0  0  0  0
 43 44  2  0  0  0  0
 13 45  1  0  0  0  0
 45 46  2  0  0  0  0
 45 47  1  0  0  0  0
 47 48  1  0  0  0  0
  3 49  1  0  0  0  0
 49 50  1  0  0  0  0
 49 51  1  0  0  0  0
 49 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  2  0  0  0  0
 53 55  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0142019

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(=CC(=O)OC1C2C34COC2(C(O)C(O)C3C2(C)C=C(OC3OC(CO)C(O)C(O)C3O)C(=O)C(C)C2CC4OC1=O)C(=O)OC)C(C)(C)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C37H50O18/c1-8-16(34(4,5)55-15(3)39)9-21(40)54-27-29-36-13-50-37(29,33(48)49-7)30(46)26(45)28(36)35(6)11-18(22(41)14(2)17(35)10-20(36)53-31(27)47)51-32-25(44)24(43)23(42)19(12-38)52-32/h9,11,14,17,19-20,23-30,32,38,42-46H,8,10,12-13H2,1-7H3

> <INCHI_KEY>
INEPMPYUXFBNMS-UHFFFAOYSA-N

> <FORMULA>
C37H50O18

> <MOLECULAR_WEIGHT>
782.789

> <EXACT_MASS>
782.29971477

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
105

> <JCHEM_AVERAGE_POLARIZABILITY>
78.20703150632617

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 3-{[4-(acetyloxy)-3-ethyl-4-methylpent-2-enoyl]oxy}-15,16-dihydroxy-9,13-dimethyl-4,10-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-11-ene-17-carboxylate

> <ALOGPS_LOGP>
0.92

> <JCHEM_LOGP>
-1.4611367916666658

> <ALOGPS_LOGS>
-2.87

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.720749545898283

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.090855913023363

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923570979257

> <JCHEM_POLAR_SURFACE_AREA>
271.34

> <JCHEM_REFRACTIVITY>
182.20730000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.05e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 3-{[4-(acetyloxy)-3-ethyl-4-methylpent-2-enoyl]oxy}-15,16-dihydroxy-9,13-dimethyl-4,10-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-11-ene-17-carboxylate

> <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      -4.998   4.967   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.111   3.708   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.758   2.311   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.871   1.052   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.337   1.191   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.690   2.588   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -1.450  -0.068   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.084   0.071   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.029  -1.438   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.730  -0.938   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.607   0.027   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.184  -1.038   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.849  -2.660   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.986  -3.847   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.552  -5.325   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.517  -3.479   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.572  -4.601   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.974  -1.989   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.543  -1.571   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.125  -3.053   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.605  -2.687   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.102  -2.325   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.164  -3.440   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      10.661  -3.078   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      11.096  -1.601   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      12.593  -1.239   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.028   0.238   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      14.525   0.600   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      13.654  -2.355   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      15.151  -1.993   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      13.219  -3.832   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      14.281  -4.948   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      11.722  -4.194   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      11.287  -5.671   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       8.537  -0.848   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      10.034  -0.486   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       7.475   0.268   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       7.910   1.745   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.978  -0.094   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.855   0.977   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       3.293   0.584   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       2.193   1.731   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       0.648   1.487   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -0.314   2.690   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -0.442  -3.500   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      -1.814  -2.801   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      -0.361  -5.037   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      -1.652  -5.877   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -6.292   2.172   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -6.430   3.706   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      -6.153   0.638   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      -7.825   2.033   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      -8.712   3.292   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0     -10.246   3.153   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      -8.066   4.690   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   49                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   43                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9   11   18   41                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    9   14   45                                             
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   10   19                                                  
CONECT   19   18   20   21   39                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   35                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   33                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   24   34                                                  
CONECT   34   33                                                            
CONECT   35   22   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   19   40                                                  
CONECT   40   39   41                                                       
CONECT   41   40   10   42                                                  
CONECT   42   41   43                                                       
CONECT   43   42    8   44                                                  
CONECT   44   43                                                            
CONECT   45   13   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   48                                                       
CONECT   48   47                                                            
CONECT   49    3   50   51   52                                             
CONECT   50   49                                                            
CONECT   51   49                                                            
CONECT   52   49   53                                                       
CONECT   53   52   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  120    0
END

View in JSmol

Synonyms

Value	Source
Methyl 3-{[4-(acetyloxy)-3-ethyl-4-methylpent-2-enoyl]oxy}-15,16-dihydroxy-9,13-dimethyl-4,10-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0,.0,.0,]nonadec-11-ene-17-carboxylic acid	Generator
Methyl 3-{[4-(acetyloxy)-3-ethyl-4-methylpent-2-enoyl]oxy}-15,16-dihydroxy-9,13-dimethyl-4,10-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-11-ene-17-carboxylic acid	Generator

Chemical Formula

C₃₇H₅₀O₁₈

Average Mass

782.7890 Da

Monoisotopic Mass

782.29971 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CCC(=CC(=O)OC1C2C34COC2(C(O)C(O)C3C2(C)C=C(OC3OC(CO)C(O)C(O)C3O)C(=O)C(C)C2CC4OC1=O)C(=O)OC)C(C)(C)OC(C)=O

InChI Identifier

InChI=1S/C37H50O18/c1-8-16(34(4,5)55-15(3)39)9-21(40)54-27-29-36-13-50-37(29,33(48)49-7)30(46)26(45)28(36)35(6)11-18(22(41)14(2)17(35)10-20(36)53-31(27)47)51-32-25(44)24(43)23(42)19(12-38)52-32/h9,11,14,17,19-20,23-30,32,38,42-46H,8,10,12-13H2,1-7H3

InChI Key

INEPMPYUXFBNMS-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
Brucea javanica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyranone glycosides. Naphthopyranone glycosides are compounds containing a carbohydrate moiety glycosidically linked to a naphthopyranone moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Naphthopyranones

Direct Parent

Naphthopyranone glycosides

Alternative Parents

Substituents

Naphthopyranone glycoside
C-20 quassinoid skeleton
Quassinoid
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Tetracarboxylic acid or derivatives
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Naphthalene
Furopyran
Delta_valerolactone
Beta-hydroxy acid
Oxepane
Fatty acid ester
Pyranone
Delta valerolactone
Cyclohexenone
Fatty acyl
Oxane
Monosaccharide
Pyran
Hydroxy acid
Furan
Methyl ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Cyclic alcohol
Tetrahydrofuran
Cyclic ketone
Carboxylic acid ester
Secondary alcohol
Lactone
Ketone
Acetal
Ether
Dialkyl ether
Oxacycle
Carboxylic acid derivative
Polyol
Alcohol
Primary alcohol
Organic oxide
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	0.92	ALOGPS
logP	-1.5	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	12.09	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	271.34 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	182.21 m³·mol⁻¹	ChemAxon
Polarizability	78.21 Å³	ChemAxon
Number of Rings	6	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

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 3-{[4-(acetyloxy)-3-ethyl-4-methylpent-2-enoyl]oxy}-15,16-dihydroxy-9,13-dimethyl-4,10-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-11-ene-17-carboxylate (NP0142019)

MOL for NP0142019 (methyl 3-{[4-(acetyloxy)-3-ethyl-4-methylpent-2-enoyl]oxy}-15,16-dihydroxy-9,13-dimethyl-4,10-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-11-ene-17-carboxylate)

3D MOL for NP0142019 (methyl 3-{[4-(acetyloxy)-3-ethyl-4-methylpent-2-enoyl]oxy}-15,16-dihydroxy-9,13-dimethyl-4,10-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-11-ene-17-carboxylate)

3D SDF for NP0142019 (methyl 3-{[4-(acetyloxy)-3-ethyl-4-methylpent-2-enoyl]oxy}-15,16-dihydroxy-9,13-dimethyl-4,10-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-11-ene-17-carboxylate)

3D-SDF for NP0142019 (methyl 3-{[4-(acetyloxy)-3-ethyl-4-methylpent-2-enoyl]oxy}-15,16-dihydroxy-9,13-dimethyl-4,10-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-11-ene-17-carboxylate)

PDB for NP0142019 (methyl 3-{[4-(acetyloxy)-3-ethyl-4-methylpent-2-enoyl]oxy}-15,16-dihydroxy-9,13-dimethyl-4,10-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-11-ene-17-carboxylate)

3D PDB for NP0142019 (methyl 3-{[4-(acetyloxy)-3-ethyl-4-methylpent-2-enoyl]oxy}-15,16-dihydroxy-9,13-dimethyl-4,10-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-11-ene-17-carboxylate)

SMILES for NP0142019 (methyl 3-{[4-(acetyloxy)-3-ethyl-4-methylpent-2-enoyl]oxy}-15,16-dihydroxy-9,13-dimethyl-4,10-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-11-ene-17-carboxylate)

INCHI for NP0142019 (methyl 3-{[4-(acetyloxy)-3-ethyl-4-methylpent-2-enoyl]oxy}-15,16-dihydroxy-9,13-dimethyl-4,10-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-11-ene-17-carboxylate)

Structure for NP0142019 (methyl 3-{[4-(acetyloxy)-3-ethyl-4-methylpent-2-enoyl]oxy}-15,16-dihydroxy-9,13-dimethyl-4,10-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-11-ene-17-carboxylate)

3D Structure for NP0142019 (methyl 3-{[4-(acetyloxy)-3-ethyl-4-methylpent-2-enoyl]oxy}-15,16-dihydroxy-9,13-dimethyl-4,10-dioxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-11-ene-17-carboxylate)