NP-MRD: Showing NP-Card for methyl 3,5-dihydroxy-6-{[2-hydroxy-9a,11a-dimethyl-1-(6-methyl-5-methylidene-4-oxoheptan-2-yl)-3-oxo-3ah,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylate (NP0157145)

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Record Information

Version

2.0

Created at

2022-09-02 14:28:03 UTC

Updated at

2022-09-02 14:28:03 UTC

NP-MRD ID

NP0157145

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 3,5-dihydroxy-6-{[2-hydroxy-9a,11a-dimethyl-1-(6-methyl-5-methylidene-4-oxoheptan-2-yl)-3-oxo-3ah,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylate

Description

Methyl 3,5-dihydroxy-6-{[13-hydroxy-2,15-dimethyl-14-(6-methyl-5-methylidene-4-oxoheptan-2-yl)-12-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-1(10),13-dien-5-yl]oxy}-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylate belongs to the class of organic compounds known as isoquinoline quinones. These are isoquinoline derivative with a structure containing a 5,8-dihydroisoquinoline-5,8-dione skeleton. methyl 3,5-dihydroxy-6-{[2-hydroxy-9a,11a-dimethyl-1-(6-methyl-5-methylidene-4-oxoheptan-2-yl)-3-oxo-3ah,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylate is found in Pandaros acanthifolium. Methyl 3,5-dihydroxy-6-{[13-hydroxy-2,15-dimethyl-14-(6-methyl-5-methylidene-4-oxoheptan-2-yl)-12-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-1(10),13-dien-5-yl]oxy}-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241511382D          

 54 59  0  0  0  0            999 V2000
    8.0178   -3.5170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2981   -2.7410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7663   -2.1103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9542   -2.2555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0466   -1.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5148   -0.7037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7951    0.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2632    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4511    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1708   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3587   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8269    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5466   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1072    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830    0.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0148    0.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3905   -0.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6708    0.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0463    1.9385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5660   -0.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0596   -0.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3705   -1.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2424   -0.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2640   -1.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0469   -2.0955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0812   -1.2185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3921   -0.4543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5876   -1.8698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4048   -1.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2767   -2.6340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5607    0.9312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6072    0.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8875    0.9934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1390   -0.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9511   -0.2681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4829   -0.8988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2026   -1.6747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7345   -2.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5466   -2.1602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0784   -2.7909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8269   -1.3843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6390   -1.2390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2951   -0.7535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5754    0.0224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8587   -1.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3905   -1.8199    0.0000 O   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
  6  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
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 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
 17 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 21 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 26 38  1  0  0  0  0
 14 39  1  0  0  0  0
  9 39  1  0  0  0  0
  7 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 47 49  1  0  0  0  0
 49 50  1  0  0  0  0
 49 51  1  0  0  0  0
 44 51  1  0  0  0  0
 51 52  1  0  0  0  0
 42 53  1  0  0  0  0
  5 53  1  0  0  0  0
 53 54  1  0  0  0  0
M  END

     RDKit          3D

112117  0  0  0  0  0  0  0  0999 V2000
   10.5806    2.2416   -1.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5601    1.3990   -1.3314 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7721    1.2726   -0.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1293    1.9777    0.8920 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6005    0.3763    0.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1540    0.2583    1.4334 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2838   -0.2661    2.2956 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9396   -0.5932    1.5889 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9132   -1.7315    2.2415 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0131   -2.3835    2.8261 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5210   -2.2512    2.2771 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1190   -3.1127    3.0971 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8399   -1.5677    1.2250 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4136   -1.1816    1.4253 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0412   -0.2135    0.5880 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9335    0.0953   -0.6053 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3834    0.2200   -0.2463 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6026   -0.2607    1.1388 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0789    0.7583    2.1371 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7928    0.5604    0.7649 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1375    2.0036    1.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0146    0.5890   -0.5680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4063    0.9889   -0.3147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1942    0.0248    0.5176 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2348   -0.6017   -0.1343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4474   -0.4782    0.4785 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8850   -1.7780    0.8268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4524   -2.3037   -0.3070 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3906   -3.7891   -0.3422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8689   -4.4215   -1.3132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8089   -4.5064    0.6858 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7850   -5.9159    0.5856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8597   -1.7935   -0.4338 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.4405   -2.1263   -1.6534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8499   -0.3064   -0.1911 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.7481    0.2708   -1.0705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7444    1.0098   -0.4382 C   0  0  2  0  0  0  0  0  0  0  0  0
  -10.0000    0.4764   -0.6206 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6496    1.1224   -1.6603 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0886    2.5127   -1.2475 C   0  0  1  0  0  0  0  0  0  0  0  0
  -12.1043    2.3428   -0.3001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9169    3.2146   -0.6407 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.7587    4.4488   -1.2906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6225    2.4531   -0.8071 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.1910    2.5978   -2.1115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4301    0.1906   -0.4403 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4898    1.5757   -0.1951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1812   -0.9429    1.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1271   -0.0326    1.7648 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4931   -0.8060    2.8686 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5238   -1.8056    2.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2721    0.6426   -2.5733 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5265   -0.8258   -2.3373 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2509    1.0579   -3.6842 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8474    2.8431   -0.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2157    2.4035   -2.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8556    0.7856   -0.6877 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9300   -0.6430   -0.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9612    1.2987    1.8259 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0718    0.4669    2.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9369   -0.4172    3.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7121   -1.1767    1.8502 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9275   -2.7200    3.7902 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9499   -2.0763    0.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8260   -0.7258   -1.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5778    1.0259   -1.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9414   -0.4269   -0.9608 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6319    1.3096   -0.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9488    1.7191    1.6010 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1585    0.4955    2.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8303    0.9968    2.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5218    2.1657    2.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2800    2.6840    0.8986 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9093    2.3133    0.3177 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4689    1.4005   -1.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1230   -0.3451   -1.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4782    2.0332    0.0146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9065    0.9846   -1.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6667    0.5045    1.4275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4274    0.1101    1.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8792   -1.9306   -1.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7450   -6.1933    0.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5091   -6.2865   -0.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0127   -6.4040    1.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5289   -2.2450    0.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4142   -2.0699   -1.5938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0740   -0.0826    0.8750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5207    0.9183    0.6675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9925    1.1783   -2.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5698    0.5175   -1.8688 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4966    3.0083   -2.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6411    3.1469   -0.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1312    3.4611    0.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6526    4.8674   -1.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8735    2.9481   -0.1322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2420    3.5474   -2.4087 H   0  0  0  0  0  0  0  0  0  0  0  0
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 42 93  1  1
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 33 85  1  1
 34 86  1  0
M  END


  Mrv1533004241511382D          

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  1  2  1  0  0  0  0
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  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
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 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
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 35 37  1  0  0  0  0
 26 38  1  0  0  0  0
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  9 39  1  0  0  0  0
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 44 45  1  0  0  0  0
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 46 47  1  0  0  0  0
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 51 52  1  0  0  0  0
 42 53  1  0  0  0  0
  5 53  1  0  0  0  0
 53 54  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0157145

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1OC(OC2CCC3(C)C(CCC4=C3CCC3(C)C4C(=O)C(O)=C3C(C)CC(=O)C(=C)C(C)C)C2)C(O)C(OC2OCC(O)C(O)C2O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C40H58O14/c1-17(2)19(4)24(41)14-18(3)26-29(44)30(45)27-22-9-8-20-15-21(10-12-39(20,5)23(22)11-13-40(26,27)6)52-38-33(48)34(32(47)35(54-38)36(49)50-7)53-37-31(46)28(43)25(42)16-51-37/h17-18,20-21,25,27-28,31-35,37-38,42-44,46-48H,4,8-16H2,1-3,5-7H3

> <INCHI_KEY>
OSSZCSYISLNNSL-UHFFFAOYSA-N

> <FORMULA>
C40H58O14

> <MOLECULAR_WEIGHT>
762.89

> <EXACT_MASS>
762.382656548

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
112

> <JCHEM_AVERAGE_POLARIZABILITY>
82.3030354330184

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 3,5-dihydroxy-6-{[13-hydroxy-2,15-dimethyl-14-(6-methyl-5-methylidene-4-oxoheptan-2-yl)-12-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),13-dien-5-yl]oxy}-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylate

> <ALOGPS_LOGP>
2.08

> <JCHEM_LOGP>
2.4084108150000016

> <ALOGPS_LOGS>
-3.89

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.940170330295977

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.115901665839118

> <JCHEM_PKA_STRONGEST_BASIC>
-3.52658066213482

> <JCHEM_POLAR_SURFACE_AREA>
218.73999999999995

> <JCHEM_REFRACTIVITY>
192.33120000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.93e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 3,5-dihydroxy-6-{[13-hydroxy-2,15-dimethyl-14-(6-methyl-5-methylidene-4-oxoheptan-2-yl)-12-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),13-dien-5-yl]oxy}-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      14.967  -6.565   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      15.490  -5.117   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      14.497  -3.939   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      12.981  -4.210   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      15.020  -2.491   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      14.028  -1.314   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      14.551   0.135   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      13.558   1.312   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.010   0.499   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.494   0.228   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.791  -1.700   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.770   2.079   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.820   3.618   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.978  -1.480   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.558  -2.907   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.452  -1.269   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.493  -2.485   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.088  -3.912   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -2.018  -2.275   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.599  -0.848   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.963  -3.490   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.489  -3.280   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.383  -4.917   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       1.047   1.738   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      11.049   2.218   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      16.067   0.406   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      16.590   1.854   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      17.059  -0.771   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      18.575  -0.500   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      19.568  -1.678   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      19.045  -3.126   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      20.038  -4.303   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      21.554  -4.032   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      22.546  -5.210   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      22.077  -2.584   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      23.593  -2.313   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      21.084  -1.407   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      21.607   0.042   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      16.536  -2.220   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      17.529  -3.397   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   53                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   40                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   39                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   18                                             
CONECT   13   12                                                            
CONECT   14   12   15   39                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   12   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   27                                             
CONECT   22   21                                                            
CONECT   23   21   17   24                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   38                                                  
CONECT   27   26   21   28                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   26                                                            
CONECT   39   14    9                                                       
CONECT   40    7   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43   53                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45   51                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   44   52                                                  
CONECT   52   51                                                            
CONECT   53   42    5   54                                                  
CONECT   54   53                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  118    0
END

View in JSmol

Synonyms

Value	Source
Methyl 3,5-dihydroxy-6-{[13-hydroxy-2,15-dimethyl-14-(6-methyl-5-methylidene-4-oxoheptan-2-yl)-12-oxotetracyclo[8.7.0.0,.0,]heptadeca-1(10),13-dien-5-yl]oxy}-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylic acid	Generator
Methyl 3,5-dihydroxy-6-{[13-hydroxy-2,15-dimethyl-14-(6-methyl-5-methylidene-4-oxoheptan-2-yl)-12-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),13-dien-5-yl]oxy}-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylic acid	Generator

Chemical Formula

C₄₀H₅₈O₁₄

Average Mass

762.8900 Da

Monoisotopic Mass

762.38266 Da

IUPAC Name

methyl 3,5-dihydroxy-6-{[13-hydroxy-2,15-dimethyl-14-(6-methyl-5-methylidene-4-oxoheptan-2-yl)-12-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),13-dien-5-yl]oxy}-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)C1OC(OC2CCC3(C)C(CCC4=C3CCC3(C)C4C(=O)C(O)=C3C(C)CC(=O)C(=C)C(C)C)C2)C(O)C(OC2OCC(O)C(O)C2O)C1O

InChI Identifier

InChI=1S/C40H58O14/c1-17(2)19(4)24(41)14-18(3)26-29(44)30(45)27-22-9-8-20-15-21(10-12-39(20,5)23(22)11-13-40(26,27)6)52-38-33(48)34(32(47)35(54-38)36(49)50-7)53-37-31(46)28(43)25(42)16-51-37/h17-18,20-21,25,27-28,31-35,37-38,42-44,46-48H,4,8-16H2,1-3,5-7H3

InChI Key

OSSZCSYISLNNSL-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
Pandaros acanthifolium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoquinoline quinones. These are isoquinoline derivative with a structure containing a 5,8-dihydroisoquinoline-5,8-dione skeleton.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoquinolines and derivatives

Sub Class

Isoquinoline quinones

Direct Parent

Isoquinoline quinones

Alternative Parents

Substituents

Isoquinoline quinone
Isoquinolone
N-alkylpiperazine
N-methylpiperazine
1,4-diazinane
Piperazine
Vinylogous ester
Amino acid or derivatives
Carboxylic acid ester
Alpha-aminonitrile
Ketone
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid derivative
Azacycle
Monocarboxylic acid or derivatives
Carbonitrile
Nitrile
Amine
Hydrocarbon derivative
Organic oxide
Cyanide
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
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	2.08	ALOGPS
logP	2.41	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	9.12	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	218.74 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	192.33 m³·mol⁻¹	ChemAxon
Polarizability	82.3 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 3,5-dihydroxy-6-{[2-hydroxy-9a,11a-dimethyl-1-(6-methyl-5-methylidene-4-oxoheptan-2-yl)-3-oxo-3ah,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylate (NP0157145)

MOL for NP0157145 (methyl 3,5-dihydroxy-6-{[2-hydroxy-9a,11a-dimethyl-1-(6-methyl-5-methylidene-4-oxoheptan-2-yl)-3-oxo-3ah,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylate)

3D MOL for NP0157145 (methyl 3,5-dihydroxy-6-{[2-hydroxy-9a,11a-dimethyl-1-(6-methyl-5-methylidene-4-oxoheptan-2-yl)-3-oxo-3ah,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylate)

3D SDF for NP0157145 (methyl 3,5-dihydroxy-6-{[2-hydroxy-9a,11a-dimethyl-1-(6-methyl-5-methylidene-4-oxoheptan-2-yl)-3-oxo-3ah,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylate)

3D-SDF for NP0157145 (methyl 3,5-dihydroxy-6-{[2-hydroxy-9a,11a-dimethyl-1-(6-methyl-5-methylidene-4-oxoheptan-2-yl)-3-oxo-3ah,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylate)

PDB for NP0157145 (methyl 3,5-dihydroxy-6-{[2-hydroxy-9a,11a-dimethyl-1-(6-methyl-5-methylidene-4-oxoheptan-2-yl)-3-oxo-3ah,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylate)

3D PDB for NP0157145 (methyl 3,5-dihydroxy-6-{[2-hydroxy-9a,11a-dimethyl-1-(6-methyl-5-methylidene-4-oxoheptan-2-yl)-3-oxo-3ah,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylate)

SMILES for NP0157145 (methyl 3,5-dihydroxy-6-{[2-hydroxy-9a,11a-dimethyl-1-(6-methyl-5-methylidene-4-oxoheptan-2-yl)-3-oxo-3ah,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylate)

INCHI for NP0157145 (methyl 3,5-dihydroxy-6-{[2-hydroxy-9a,11a-dimethyl-1-(6-methyl-5-methylidene-4-oxoheptan-2-yl)-3-oxo-3ah,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylate)

Structure for NP0157145 (methyl 3,5-dihydroxy-6-{[2-hydroxy-9a,11a-dimethyl-1-(6-methyl-5-methylidene-4-oxoheptan-2-yl)-3-oxo-3ah,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylate)

3D Structure for NP0157145 (methyl 3,5-dihydroxy-6-{[2-hydroxy-9a,11a-dimethyl-1-(6-methyl-5-methylidene-4-oxoheptan-2-yl)-3-oxo-3ah,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxane-2-carboxylate)