NP-MRD: Showing NP-Card for 1,3-bis(acetyloxy)-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-5-yl hexanoate (NP0164787)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 23:44:08 UTC

Updated at

2022-09-02 23:44:09 UTC

NP-MRD ID

NP0164787

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,3-bis(acetyloxy)-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-5-yl hexanoate

Description

1,3-Bis(acetyloxy)-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1H,3H,5H,6H,6aH,7H,8H,9H,10H-naphtho[4,4a-c]furan-5-yl hexanoate belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations. 1,3-bis(acetyloxy)-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-5-yl hexanoate is found in Casearia tremula. 1,3-Bis(acetyloxy)-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1H,3H,5H,6H,6aH,7H,8H,9H,10H-naphtho[4,4a-c]furan-5-yl hexanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201503282D          

 37 39  0  0  0  0            999 V2000
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3895   -3.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3289   -3.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6110   -2.3053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0807   -1.6733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2683   -1.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3629   -0.8980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8326   -0.2660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0846   -5.3021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7578   -5.5020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5648   -5.3305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1168   -5.9436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9238   -5.7721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8619   -6.7282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4222   -6.2557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6018   -6.1695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0497   -6.7826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3047   -7.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1116   -7.7387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7526   -8.1803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  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  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 12 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 11 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  2  0  0  0  0
 27 29  1  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 31 36  1  0  0  0  0
 24 36  1  0  0  0  0
 36 37  2  0  0  0  0
  9 37  1  0  0  0  0
M  END

     RDKit          3D

 81 83  0  0  0  0  0  0  0  0999 V2000
   -3.4077   -4.6060    1.9793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2142   -4.6600    2.5163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1357   -3.8006    2.1530 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0300   -3.9042    2.7292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2872   -2.8207    1.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8708   -1.5734    1.5035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2118   -0.4288    0.6234 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2963   -0.8868   -0.3547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8518    0.6326    1.5084 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2730    0.2852    1.9054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8136    2.0181    1.0324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7347    2.4947    0.1389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3745    1.3755   -0.8912 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1809    1.7581   -1.6804 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0380    1.2868   -1.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3924    0.2797   -0.5219 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4903   -0.5010   -0.9394 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7064   -0.6482   -0.3151 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8804   -0.0227    0.7586 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7813   -1.5254   -0.9043 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9903   -1.4332    0.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1204   -2.2817   -0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3065   -2.1678    0.4022 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0897   -2.6190    1.8059 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1622   -0.5928   -0.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0534    0.2189   -0.0461 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7372    2.7789   -2.6567 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7864    4.0366   -2.1058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0961    5.1376   -2.6061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1742    6.4744   -1.9814 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6116    4.9545   -3.6274 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8696    2.1624   -3.0594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3949    1.3990   -1.9436 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5012    2.2734   -1.6083 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7980    2.0627   -2.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8543    3.0277   -1.5997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0270    1.0559   -2.7138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2097   -5.2925    2.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6479   -3.8984    1.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0559   -5.4275    3.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2648   -4.5603    3.5435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8819   -3.2578    2.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3467   -2.8470    0.5067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9902   -3.3287    0.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7756   -1.8803    2.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1825   -1.2054    2.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8509   -1.7070    0.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9188   -1.4205   -1.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0832   -0.1487   -0.4927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2544    0.5826    2.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9765    0.6767    1.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5628    0.7903    2.8531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4210   -0.8030    1.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8410    2.2874    0.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7297    2.6743    1.9717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1081    3.3239   -0.4563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8583    2.7976    0.7106 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7952    1.6932   -2.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6313    0.7753    0.4248 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3916   -2.5561   -0.9913 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0643   -1.0613   -1.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2493   -0.3844    0.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6545   -1.8422    0.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4208   -1.8475   -1.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7475   -3.3233   -0.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6724   -1.1004    0.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2050   -2.7022   -0.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5112   -3.6554    1.8768 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0332   -2.7179    2.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5886   -1.9442    2.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0724   -1.2508   -1.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4674   -1.1182    0.6803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6476    0.8135    0.9381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0604    2.8398   -3.5497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8158    7.1794   -2.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5804    6.3556   -0.9648 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8277    6.9260   -1.9201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7605    0.5210   -2.4248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7358    2.9725   -2.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5055    4.0636   -1.5747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2157    2.7680   -0.5853 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 23  1  0
 23 22  1  0
 22 21  1  0
 21 20  1  0
 20 18  1  0
 18 19  2  0
 18 17  1  0
 17 16  1  0
 16 25  1  0
 25 26  1  0
 26 13  1  0
 13 12  1  1
 12 11  1  0
 11  9  1  0
  9 10  1  0
  9  7  1  0
  7  8  1  6
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  3
  3  2  1  0
  2  1  2  3
 13 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 35 37  2  0
 33 32  1  0
 32 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 27 14  1  0
 14 15  2  0
 15 16  1  0
  7 26  1  0
 14 13  1  0
 24 68  1  0
 24 69  1  0
 24 70  1  0
 23 66  1  0
 23 67  1  0
 22 64  1  0
 22 65  1  0
 21 62  1  0
 21 63  1  0
 20 60  1  0
 20 61  1  0
 16 59  1  1
 25 71  1  0
 25 72  1  0
 26 73  1  1
 12 56  1  0
 12 57  1  0
 11 54  1  0
 11 55  1  0
  9 50  1  1
 10 51  1  0
 10 52  1  0
 10 53  1  0
  8 47  1  0
  8 48  1  0
  8 49  1  0
  6 45  1  0
  6 46  1  0
  5 43  1  0
  5 44  1  0
  4 41  1  0
  4 42  1  0
  2 40  1  0
  1 38  1  0
  1 39  1  0
 33 78  1  6
 36 79  1  0
 36 80  1  0
 36 81  1  0
 27 74  1  6
 30 75  1  0
 30 76  1  0
 30 77  1  0
 15 58  1  0
M  END


  Mrv1533004201503282D          

 37 39  0  0  0  0            999 V2000
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3895   -3.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3289   -3.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6110   -2.3053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0807   -1.6733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2683   -1.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3629   -0.8980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8326   -0.2660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0846   -5.3021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7578   -5.5020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5648   -5.3305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1168   -5.9436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9238   -5.7721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8619   -6.7282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4222   -6.2557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6018   -6.1695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0497   -6.7826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3047   -7.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1116   -7.7387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7526   -8.1803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  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  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 12 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 11 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  2  0  0  0  0
 27 29  1  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 31 36  1  0  0  0  0
 24 36  1  0  0  0  0
 36 37  2  0  0  0  0
  9 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0164787

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC(=O)OC1CC2C3(CCC(C)C2(C)CCC(=C)C=C)C(OC(C)=O)OC(OC(C)=O)C3=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H44O7/c1-8-10-11-12-26(33)36-23-17-24-27(34-21(5)31)37-28(35-22(6)32)30(24)16-14-20(4)29(7,25(30)18-23)15-13-19(3)9-2/h9,17,20,23,25,27-28H,2-3,8,10-16,18H2,1,4-7H3

> <INCHI_KEY>
CLKYEEBDHIOOKW-UHFFFAOYSA-N

> <FORMULA>
C30H44O7

> <MOLECULAR_WEIGHT>
516.675

> <EXACT_MASS>
516.308703757

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
58.488048277685266

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,3-bis(acetyloxy)-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1H,3H,5H,6H,6aH,7H,8H,9H,10H-naphtho[4,4a-c]furan-5-yl hexanoate

> <ALOGPS_LOGP>
5.37

> <JCHEM_LOGP>
6.134613998333332

> <ALOGPS_LOGS>
-6.20

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.548874158710374

> <JCHEM_POLAR_SURFACE_AREA>
88.13

> <JCHEM_REFRACTIVITY>
139.82219999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.25e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,3-bis(acetyloxy)-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1H,3H,5H,6H,6aH,8H,9H,10H-naphtho[4,4a-c]furan-5-yl hexanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.660  -5.750   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.681  -5.750   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.207  -4.303   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.217  -3.123   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.701  -3.391   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.744  -1.676   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.754  -0.497   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.004  -7.700   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.338  -6.930   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.004  -9.240   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.091  -9.897   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.481 -10.270   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      15.988  -9.950   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      17.018 -11.095   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      18.524 -10.775   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      16.542 -12.559   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      13.855 -11.677   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      12.323 -11.516   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      11.293 -12.661   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      11.769 -14.125   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      13.275 -14.446   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      10.738 -15.270   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   37                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   24                                                  
CONECT   12   11   13   14   20                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20   12   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   11   25   36                                             
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   25   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   31   24   37                                                  
CONECT   37   36    9                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

View in JSmol

Synonyms

Value	Source
1,3-Bis(acetyloxy)-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1H,3H,5H,6H,6ah,7H,8H,9H,10H-naphtho[4,4a-c]furan-5-yl hexanoic acid	Generator

Chemical Formula

C₃₀H₄₄O₇

Average Mass

516.6750 Da

Monoisotopic Mass

516.30870 Da

IUPAC Name

1,3-bis(acetyloxy)-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1H,3H,5H,6H,6aH,7H,8H,9H,10H-naphtho[4,4a-c]furan-5-yl hexanoate

Traditional Name

1,3-bis(acetyloxy)-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1H,3H,5H,6H,6aH,8H,9H,10H-naphtho[4,4a-c]furan-5-yl hexanoate

CAS Registry Number

Not Available

SMILES

CCCCCC(=O)OC1CC2C3(CCC(C)C2(C)CCC(=C)C=C)C(OC(C)=O)OC(OC(C)=O)C3=C1

InChI Identifier

InChI=1S/C30H44O7/c1-8-10-11-12-26(33)36-23-17-24-27(34-21(5)31)37-28(35-22(6)32)30(24)16-14-20(4)29(7,25(30)18-23)15-13-19(3)9-2/h9,17,20,23,25,27-28H,2-3,8,10-16,18H2,1,4-7H3

InChI Key

CLKYEEBDHIOOKW-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
Casearia tremula	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Colensane and clerodane diterpenoids

Alternative Parents

Substituents

Clerodane diterpenoid
Naphthofuran
Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Tetrahydrofuran
Carboxylic acid ester
Oxacycle
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
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	5.37	ALOGPS
logP	6.13	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	88.13 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	139.82 m³·mol⁻¹	ChemAxon
Polarizability	58.49 Å³	ChemAxon
Number of Rings	3	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

73803071

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1,3-bis(acetyloxy)-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-5-yl hexanoate (NP0164787)

MOL for NP0164787 (1,3-bis(acetyloxy)-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-5-yl hexanoate)

3D MOL for NP0164787 (1,3-bis(acetyloxy)-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-5-yl hexanoate)

3D SDF for NP0164787 (1,3-bis(acetyloxy)-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-5-yl hexanoate)

3D-SDF for NP0164787 (1,3-bis(acetyloxy)-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-5-yl hexanoate)

PDB for NP0164787 (1,3-bis(acetyloxy)-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-5-yl hexanoate)

3D PDB for NP0164787 (1,3-bis(acetyloxy)-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-5-yl hexanoate)

SMILES for NP0164787 (1,3-bis(acetyloxy)-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-5-yl hexanoate)

INCHI for NP0164787 (1,3-bis(acetyloxy)-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-5-yl hexanoate)

Structure for NP0164787 (1,3-bis(acetyloxy)-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-5-yl hexanoate)

3D Structure for NP0164787 (1,3-bis(acetyloxy)-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-5-yl hexanoate)