NP-MRD: Showing NP-Card for (1s,3s,6r,7s,8r,9r)-3-[(2r,6r)-6-[(1s,4as,8ar)-4,7-dimethyl-1,2,4a,5,6,8a-hexahydronaphthalen-1-yl]heptan-2-yl]-8,9-dihydroxy-2,4,10-trioxabicyclo[4.3.1]decan-7-yl acetate (NP0197132)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 15:20:16 UTC

Updated at

2022-09-04 15:20:16 UTC

NP-MRD ID

NP0197132

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3s,6r,7s,8r,9r)-3-[(2r,6r)-6-[(1s,4as,8ar)-4,7-dimethyl-1,2,4a,5,6,8a-hexahydronaphthalen-1-yl]heptan-2-yl]-8,9-dihydroxy-2,4,10-trioxabicyclo[4.3.1]decan-7-yl acetate

Description

(1S,3S,6R,7S,8R,9R)-3-[(2R,6R)-6-[(1S,4aS,8aR)-4,7-dimethyl-1,2,4a,5,6,8a-hexahydronaphthalen-1-yl]heptan-2-yl]-8,9-dihydroxy-2,4,10-trioxabicyclo[4.3.1]Decan-7-yl acetate belongs to the class of organic compounds known as biflorane and serrulatane diterpenoids. These are diterpenoids with a structure based either on the biflorane or the serrulatane skeleton. Based on a literature review very few articles have been published on (1S,3S,6R,7S,8R,9R)-3-[(2R,6R)-6-[(1S,4aS,8aR)-4,7-dimethyl-1,2,4a,5,6,8a-hexahydronaphthalen-1-yl]heptan-2-yl]-8,9-dihydroxy-2,4,10-trioxabicyclo[4.3.1]Decan-7-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042217202D          

 35 38  0  0  1  0            999 V2000
   -0.1204   -0.5852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4099    0.0468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1277    0.8221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2223   -0.0964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7526    0.5356    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5279    0.2534    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3031    0.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7156    1.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5737    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.5737    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9404    2.5928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1154    2.5928    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0292    1.3715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4834    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7689    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3401    1.2500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5277    1.1068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  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  1  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 17 15  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 22 20  1  1  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
 25 27  2  0  0  0  0
 28 27  1  1  0  0  0
 22 28  1  0  0  0  0
 17 28  1  0  0  0  0
  9 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  1  0  0  0
  6 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
  5 34  1  0  0  0  0
 34 35  1  6  0  0  0
M  END

     RDKit          3D

 79 82  0  0  0  0  0  0  0  0999 V2000
    9.7255    1.6347    1.1780 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4418    1.7802    0.4309 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0281    2.8911    0.0462 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6936    0.6697    0.1572 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4488    0.7080   -0.5538 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3967    0.2208    0.4094 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9942    0.5658   -0.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5346   -0.2163   -1.0502 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1563   -1.4835   -0.7452 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0837   -1.5386    0.3521 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7702   -3.0323    0.5147 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9009   -0.7837   -0.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2985   -0.8752    0.7504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4656   -0.0845    0.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6832   -0.1553    1.0459 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4050    0.4142    2.4022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8434    0.4702    0.3315 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6432    1.9573    0.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6050    2.3101   -0.9630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8516    1.9054   -0.7882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9067    2.2049   -1.8271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1966    1.1719    0.4465 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.5399    0.4848    0.2670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4056   -0.8830   -0.3158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5377   -1.6969    0.5719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8367   -3.1601    0.7627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5268   -1.1110    1.1688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1675    0.3040    1.0376 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1348   -2.3908   -0.4655 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4287   -1.9379   -0.4454 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5941   -1.1049    0.6342 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8747   -1.4348   -1.7546 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7347   -2.3597   -2.3986 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5450   -0.1142   -1.7850 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0324    0.6647   -2.8508 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4209    0.9385    0.6238 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4822    1.2302    2.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1912    2.6389    1.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2832    1.7967   -0.7939 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5678    0.7629    1.3613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0330    1.6198   -0.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3155    0.5983    0.8581 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6103   -1.8822   -1.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4447   -1.1890    1.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7459   -3.5552    0.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1486   -3.3955   -0.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3676   -3.2572    1.5114 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1915    0.2847   -0.2187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5949   -1.0893   -1.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6563   -1.8949    0.9008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0614   -0.4443    1.7411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1153    0.9367   -0.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7706   -0.5174   -0.8235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8936   -1.2560    1.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4931   -0.3442    3.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3951    0.9107    2.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1111    1.2401    2.6979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8863    0.0463   -0.7101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6380    2.2528   -0.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9224    2.4419    1.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3117    2.8622   -1.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4138    2.7842   -2.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2764    1.2696   -2.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7073    2.8486   -1.4136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4299    1.9936    1.1936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0978    0.4364    1.2138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1275    1.1080   -0.4363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4329   -1.3326   -0.3303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9875   -0.9052   -1.3271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2646   -3.5195   -0.1927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8750   -3.6853    0.9464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5305   -3.3439    1.5898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9070   -1.7340    1.8131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9326    0.6345    2.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0532   -2.8532   -0.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9770   -1.4066   -2.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1816   -1.9758   -3.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6420   -0.2114   -2.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3805    0.2277   -3.6819 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 10  1  0
 10 11  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6 31  1  0
 31 30  1  0
 30 29  1  0
 30 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 34  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 27 28  1  0
 29  9  1  0
 28 17  1  0
  5  6  1  0
 28 22  1  0
 16 55  1  0
 16 56  1  0
 16 57  1  0
 15 54  1  1
 14 52  1  0
 14 53  1  0
 13 50  1  0
 13 51  1  0
 12 48  1  0
 12 49  1  0
 10 44  1  1
 11 45  1  0
 11 46  1  0
 11 47  1  0
  9 43  1  6
  7 41  1  0
  7 42  1  0
  6 40  1  1
 30 75  1  1
 32 76  1  6
 33 77  1  0
 34 78  1  6
 35 79  1  0
  5 39  1  6
  1 36  1  0
  1 37  1  0
  1 38  1  0
 17 58  1  6
 18 59  1  0
 18 60  1  0
 19 61  1  0
 21 62  1  0
 21 63  1  0
 21 64  1  0
 22 65  1  1
 23 66  1  0
 23 67  1  0
 24 68  1  0
 24 69  1  0
 26 70  1  0
 26 71  1  0
 26 72  1  0
 27 73  1  0
 28 74  1  1
M  END


  Mrv1652309042217202D          

 35 38  0  0  1  0            999 V2000
   -0.1204   -0.5852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4099    0.0468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1277    0.8221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2223   -0.0964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7526    0.5356    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5279    0.2534    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3031    0.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7156    1.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5737    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.5737    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9404    2.5928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1154    2.5928    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0292    1.3715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4834    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7689    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3401    1.2500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5277    1.1068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  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  1  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 17 15  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 22 20  1  1  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
 25 27  2  0  0  0  0
 28 27  1  1  0  0  0
 22 28  1  0  0  0  0
 17 28  1  0  0  0  0
  9 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  1  0  0  0
  6 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
  5 34  1  0  0  0  0
 34 35  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0197132

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](CCC[C@@H](C)[C@H]1OC[C@H]2O[C@@H](O1)[C@H](O)[C@@H](O)[C@@H]2OC(C)=O)[C@@H]1CC=C(C)[C@H]2CCC(C)=C[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C28H44O7/c1-15-9-11-20-17(3)10-12-21(22(20)13-15)16(2)7-6-8-18(4)27-32-14-23-26(33-19(5)29)24(30)25(31)28(34-23)35-27/h10,13,16,18,20-28,30-31H,6-9,11-12,14H2,1-5H3/t16-,18-,20-,21+,22-,23-,24-,25-,26-,27+,28+/m1/s1

> <INCHI_KEY>
UNPUXBUKESCWCN-NRTPGWCVSA-N

> <FORMULA>
C28H44O7

> <MOLECULAR_WEIGHT>
492.653

> <EXACT_MASS>
492.308703757

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
55.31234144942455

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3S,6R,7S,8R,9R)-3-[(2R,6R)-6-[(1S,4aS,8aR)-4,7-dimethyl-1,2,4a,5,6,8a-hexahydronaphthalen-1-yl]heptan-2-yl]-8,9-dihydroxy-2,4,10-trioxabicyclo[4.3.1]decan-7-yl acetate

> <JCHEM_LOGP>
4.508335229666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.878065879043362

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.267162132357203

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6934724902767107

> <JCHEM_POLAR_SURFACE_AREA>
94.45000000000002

> <JCHEM_REFRACTIVITY>
132.5425

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,6R,7S,8R,9R)-3-[(2R,6R)-6-[(1S,4aS,8aR)-4,7-dimethyl-1,2,4a,5,6,8a-hexahydronaphthalen-1-yl]heptan-2-yl]-8,9-dihydroxy-2,4,10-trioxabicyclo[4.3.1]decan-7-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.225  -1.092   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.765   0.087   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.238   1.535   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.282  -0.180   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.272   1.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.719   0.473   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.166   1.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.936   2.333   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.337   6.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.670   3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.004   4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.338   3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.338   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      18.672   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.004   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.004   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.670  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.670   2.310   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.489   4.840   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.949   4.840   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.788   2.560   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.769   3.850   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       1.435   4.620   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.502   2.333   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       0.985   2.066   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   34                                                  
CONECT    6    5    7   31                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   29                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   28                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   22   17                                                  
CONECT   29    9   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30    6                                                       
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32    5   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
(1S,3S,6R,7S,8R,9R)-3-[(2R,6R)-6-[(1S,4AS,8ar)-4,7-dimethyl-1,2,4a,5,6,8a-hexahydronaphthalen-1-yl]heptan-2-yl]-8,9-dihydroxy-2,4,10-trioxabicyclo[4.3.1]decan-7-yl acetic acid	Generator

Chemical Formula

C₂₈H₄₄O₇

Average Mass

492.6530 Da

Monoisotopic Mass

492.30870 Da

IUPAC Name

(1S,3S,6R,7S,8R,9R)-3-[(2R,6R)-6-[(1S,4aS,8aR)-4,7-dimethyl-1,2,4a,5,6,8a-hexahydronaphthalen-1-yl]heptan-2-yl]-8,9-dihydroxy-2,4,10-trioxabicyclo[4.3.1]decan-7-yl acetate

Traditional Name

(1S,3S,6R,7S,8R,9R)-3-[(2R,6R)-6-[(1S,4aS,8aR)-4,7-dimethyl-1,2,4a,5,6,8a-hexahydronaphthalen-1-yl]heptan-2-yl]-8,9-dihydroxy-2,4,10-trioxabicyclo[4.3.1]decan-7-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@H](CCC[C@@H](C)[C@H]1OC[C@H]2O[C@@H](O1)[C@H](O)[C@@H](O)[C@@H]2OC(C)=O)[C@@H]1CC=C(C)[C@H]2CCC(C)=C[C@@H]12

InChI Identifier

InChI=1S/C28H44O7/c1-15-9-11-20-17(3)10-12-21(22(20)13-15)16(2)7-6-8-18(4)27-32-14-23-26(33-19(5)29)24(30)25(31)28(34-23)35-27/h10,13,16,18,20-28,30-31H,6-9,11-12,14H2,1-5H3/t16-,18-,20-,21+,22-,23-,24-,25-,26-,27+,28+/m1/s1

InChI Key

UNPUXBUKESCWCN-NRTPGWCVSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biflorane and serrulatane diterpenoids. These are diterpenoids with a structure based either on the biflorane or the serrulatane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Biflorane and serrulatane diterpenoids

Alternative Parents

Substituents

Biflorane diterpenoid
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Fatty acyl
Oxane
Monosaccharide
1,2-diol
Carboxylic acid ester
Secondary alcohol
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organic oxide
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	4.51	ChemAxon
pKa (Strongest Acidic)	12.27	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	94.45 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	132.54 m³·mol⁻¹	ChemAxon
Polarizability	55.31 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

162971975

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3s,6r,7s,8r,9r)-3-[(2r,6r)-6-[(1s,4as,8ar)-4,7-dimethyl-1,2,4a,5,6,8a-hexahydronaphthalen-1-yl]heptan-2-yl]-8,9-dihydroxy-2,4,10-trioxabicyclo[4.3.1]decan-7-yl acetate (NP0197132)

MOL for NP0197132 ((1s,3s,6r,7s,8r,9r)-3-[(2r,6r)-6-[(1s,4as,8ar)-4,7-dimethyl-1,2,4a,5,6,8a-hexahydronaphthalen-1-yl]heptan-2-yl]-8,9-dihydroxy-2,4,10-trioxabicyclo[4.3.1]decan-7-yl acetate)

3D MOL for NP0197132 ((1s,3s,6r,7s,8r,9r)-3-[(2r,6r)-6-[(1s,4as,8ar)-4,7-dimethyl-1,2,4a,5,6,8a-hexahydronaphthalen-1-yl]heptan-2-yl]-8,9-dihydroxy-2,4,10-trioxabicyclo[4.3.1]decan-7-yl acetate)

3D SDF for NP0197132 ((1s,3s,6r,7s,8r,9r)-3-[(2r,6r)-6-[(1s,4as,8ar)-4,7-dimethyl-1,2,4a,5,6,8a-hexahydronaphthalen-1-yl]heptan-2-yl]-8,9-dihydroxy-2,4,10-trioxabicyclo[4.3.1]decan-7-yl acetate)

3D-SDF for NP0197132 ((1s,3s,6r,7s,8r,9r)-3-[(2r,6r)-6-[(1s,4as,8ar)-4,7-dimethyl-1,2,4a,5,6,8a-hexahydronaphthalen-1-yl]heptan-2-yl]-8,9-dihydroxy-2,4,10-trioxabicyclo[4.3.1]decan-7-yl acetate)

PDB for NP0197132 ((1s,3s,6r,7s,8r,9r)-3-[(2r,6r)-6-[(1s,4as,8ar)-4,7-dimethyl-1,2,4a,5,6,8a-hexahydronaphthalen-1-yl]heptan-2-yl]-8,9-dihydroxy-2,4,10-trioxabicyclo[4.3.1]decan-7-yl acetate)

3D PDB for NP0197132 ((1s,3s,6r,7s,8r,9r)-3-[(2r,6r)-6-[(1s,4as,8ar)-4,7-dimethyl-1,2,4a,5,6,8a-hexahydronaphthalen-1-yl]heptan-2-yl]-8,9-dihydroxy-2,4,10-trioxabicyclo[4.3.1]decan-7-yl acetate)

SMILES for NP0197132 ((1s,3s,6r,7s,8r,9r)-3-[(2r,6r)-6-[(1s,4as,8ar)-4,7-dimethyl-1,2,4a,5,6,8a-hexahydronaphthalen-1-yl]heptan-2-yl]-8,9-dihydroxy-2,4,10-trioxabicyclo[4.3.1]decan-7-yl acetate)

INCHI for NP0197132 ((1s,3s,6r,7s,8r,9r)-3-[(2r,6r)-6-[(1s,4as,8ar)-4,7-dimethyl-1,2,4a,5,6,8a-hexahydronaphthalen-1-yl]heptan-2-yl]-8,9-dihydroxy-2,4,10-trioxabicyclo[4.3.1]decan-7-yl acetate)

Structure for NP0197132 ((1s,3s,6r,7s,8r,9r)-3-[(2r,6r)-6-[(1s,4as,8ar)-4,7-dimethyl-1,2,4a,5,6,8a-hexahydronaphthalen-1-yl]heptan-2-yl]-8,9-dihydroxy-2,4,10-trioxabicyclo[4.3.1]decan-7-yl acetate)

3D Structure for NP0197132 ((1s,3s,6r,7s,8r,9r)-3-[(2r,6r)-6-[(1s,4as,8ar)-4,7-dimethyl-1,2,4a,5,6,8a-hexahydronaphthalen-1-yl]heptan-2-yl]-8,9-dihydroxy-2,4,10-trioxabicyclo[4.3.1]decan-7-yl acetate)