NP-MRD: Showing NP-Card for (1r,2r,3s,4r,5s,7s,8s,9r,10s,12z,14s,17r)-2,7,9-tris(acetyloxy)-5-(butanoyloxy)-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-12-en-10-yl butanoate (NP0161962)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 20:16:32 UTC

Updated at

2022-09-02 20:16:33 UTC

NP-MRD ID

NP0161962

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,3s,4r,5s,7s,8s,9r,10s,12z,14s,17r)-2,7,9-tris(acetyloxy)-5-(butanoyloxy)-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-12-en-10-yl butanoate

Description

Excavatolide H belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (1r,2r,3s,4r,5s,7s,8s,9r,10s,12z,14s,17r)-2,7,9-tris(acetyloxy)-5-(butanoyloxy)-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-12-en-10-yl butanoate is found in Briareum excavatum. Based on a literature review a small amount of articles have been published on Excavatolide H.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022222162D          

 47 50  0  0  1  0            999 V2000
    5.1336   -3.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0960   -2.6606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3634   -2.2811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6685   -2.7257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7061   -3.5499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9360   -2.3462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8984   -1.5221    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5933   -1.0774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5557   -0.2533    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2506    0.1913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9832   -0.1882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6781    0.2565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0208   -1.0123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8232    0.1262    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5181    0.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1283   -0.3184    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1659   -1.1426    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4709   -1.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3957    0.0611    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6862   -0.7111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1626   -1.3487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4531   -2.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2700   -1.3003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7008   -0.3836    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3384   -0.9071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5662   -1.1975    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7744   -1.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2495   -1.3211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6290   -2.0536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6190   -0.5835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0317   -0.0041    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0693    0.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6256    1.2647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5880    2.0889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3581    0.8852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0530    1.3298    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0154    2.1540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9463    2.8572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6789    2.4776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6728    3.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3677    3.8674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3301    4.6916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7856    0.9503    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4805    1.3950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4429    2.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7104    2.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1378    2.6638    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  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  6  1  6  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  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  1  0  0  0
 16 14  1  6  0  0  0
 16 17  1  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  6  0  0  0
 16 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 31 30  1  1  0  0  0
 24 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  6  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 36 43  1  0  0  0  0
 14 43  1  0  0  0  0
 43 44  1  6  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 45 47  2  0  0  0  0
M  END

     RDKit          2D

 95 98  0  0  0  0  0  0  0  0999 V2000
   11.3464    2.3199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8691    2.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3919    1.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9147    1.5385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4017    0.1289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9505    2.6875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4733    2.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4733    3.9271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1743    4.6771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2101    5.8261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7231    7.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7590    8.3847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2003    7.4961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8752    3.9271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1871    5.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8752    2.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1743    1.6771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1385    0.5280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9936    1.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4202    0.7500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7320   -0.7172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1586   -1.1807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7480   -1.8493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4330    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8660    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4330   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1771   -2.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8596   -1.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3231   -2.6401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7413    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8596    1.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7413    2.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7413    3.9271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1679    4.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8596    5.1406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4330    5.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3147    6.8176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7046    8.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7952    8.1617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5863    9.4015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4679   10.6150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3496   11.8285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9936    5.1406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9936    6.6406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3055    7.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3055    8.8906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7870    7.1560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6068    0.8427    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0859    3.7971    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.8236    2.5803    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6087    3.5366    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1296    0.5822    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6524    0.3217    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1315    3.2761    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3122    1.1835    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9505    3.6666    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9864    5.3366    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2713    5.7000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9080    9.3489    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3406    7.8965    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9420    9.6428    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8390    6.0519    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6686    5.6290    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8447    6.7424    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3636    1.0088    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6861    0.2587    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2569   -0.6856    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3965    1.3449    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1027   -0.6211    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3565   -0.2419    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6951   -2.6073    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1027   -0.0151    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5852   -1.6443    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1932   -2.7304    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6116   -1.6818    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7872   -3.4906    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3596    1.2135    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1679    1.9635    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6314    2.9640    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8817    5.8630    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5944    4.8541    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3973    6.5409    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2190    5.7745    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0449    7.0530    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4893   10.4245    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7998    8.5198    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6815    9.7333    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2544   11.4967    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1361   12.7102    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5631   10.9468    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2313   13.0420    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0354    6.2197    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7609    9.2535    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0189    9.5949    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1226   10.3794    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
  9 14  1  0
 14 15  1  1
 14 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 19 24  1  0
 24 25  1  6
 25 26  1  0
 26 27  1  6
 26 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  2  0
 38 40  1  0
 40 41  1  0
 41 42  1  0
 36 43  1  0
 43 44  1  0
 44 45  1  0
 45 46  1  0
 45 47  2  0
 17  7  1  0
 26 24  1  0
 43 14  1  0
 31 24  1  0
  1 48  1  0
  1 49  1  0
  1 50  1  0
  2 51  1  0
  2 52  1  0
  3 53  1  0
  3 54  1  0
  7 55  1  1
  8 56  1  0
  8 57  1  0
  9 58  1  6
 12 59  1  0
 12 60  1  0
 12 61  1  0
 15 62  1  0
 15 63  1  0
 15 64  1  0
 16 65  1  1
 17 66  1  1
 18 67  1  0
 18 68  1  0
 18 69  1  0
 19 70  1  6
 22 71  1  0
 22 72  1  0
 22 73  1  0
 27 74  1  0
 27 75  1  0
 27 76  1  0
 31 77  1  6
 32 78  1  0
 34 79  1  0
 34 80  1  0
 34 81  1  0
 35 82  1  0
 35 83  1  0
 36 84  1  1
 40 85  1  0
 40 86  1  0
 41 87  1  0
 41 88  1  0
 42 89  1  0
 42 90  1  0
 42 91  1  0
 43 92  1  1
 46 93  1  0
 46 94  1  0
 46 95  1  0
M  END


  Mrv1652309022222162D          

 47 50  0  0  1  0            999 V2000
    5.1336   -3.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0960   -2.6606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3634   -2.2811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6685   -2.7257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7061   -3.5499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9360   -2.3462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8984   -1.5221    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5933   -1.0774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5557   -0.2533    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2506    0.1913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9832   -0.1882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6781    0.2565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0208   -1.0123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8232    0.1262    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5181    0.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1283   -0.3184    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1659   -1.1426    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4709   -1.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3957    0.0611    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6862   -0.7111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1626   -1.3487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4531   -2.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2700   -1.3003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7008   -0.3836    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3384   -0.9071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5662   -1.1975    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7744   -1.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2495   -1.3211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6290   -2.0536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6190   -0.5835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0317   -0.0041    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0693    0.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6256    1.2647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5880    2.0889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3581    0.8852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0530    1.3298    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0154    2.1540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9463    2.8572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6789    2.4776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6728    3.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3677    3.8674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3301    4.6916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7856    0.9503    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4805    1.3950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4429    2.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7104    2.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1378    2.6638    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  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  6  1  6  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  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  1  0  0  0
 16 14  1  6  0  0  0
 16 17  1  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  6  0  0  0
 16 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 31 30  1  1  0  0  0
 24 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  6  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 36 43  1  0  0  0  0
 14 43  1  0  0  0  0
 43 44  1  6  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 45 47  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0161962

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC(=O)O[C@H]1C[C@H](OC(C)=O)[C@]2(C)[C@H]([C@H]1C)[C@@H](OC(C)=O)[C@@]13O[C@@]1(C)C(=O)O[C@H]3\C=C(C)/C[C@H](OC(=O)CCC)[C@@H]2OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C34H48O13/c1-10-12-26(38)44-22-16-24(41-19(5)35)32(8)28(18(22)4)30(43-21(7)37)34-25(46-31(40)33(34,9)47-34)15-17(3)14-23(29(32)42-20(6)36)45-27(39)13-11-2/h15,18,22-25,28-30H,10-14,16H2,1-9H3/b17-15-/t18-,22-,23-,24-,25-,28+,29-,30+,32+,33-,34+/m0/s1

> <INCHI_KEY>
ISQVFOAGBSWCLK-SMJOTQBDSA-N

> <FORMULA>
C34H48O13

> <MOLECULAR_WEIGHT>
664.745

> <EXACT_MASS>
664.309491606

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
95

> <JCHEM_AVERAGE_POLARIZABILITY>
74.80196868993116

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,3S,4R,5S,7S,8S,9R,10S,12Z,14S,17R)-2,7,9-tris(acetyloxy)-5-(butanoyloxy)-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0^{1,17}.0^{3,8}]octadec-12-en-10-yl butanoate

> <ALOGPS_LOGP>
3.23

> <JCHEM_LOGP>
3.3712759626666644

> <ALOGPS_LOGS>
-4.89

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.359360696395928

> <JCHEM_POLAR_SURFACE_AREA>
170.32999999999998

> <JCHEM_REFRACTIVITY>
160.96830000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.53e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,3S,4R,5S,7S,8S,9R,10S,12Z,14S,17R)-2,7,9-tris(acetyloxy)-5-(butanoyloxy)-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0^{1,17}.0^{3,8}]octadec-12-en-10-yl butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       9.583  -6.505   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.512  -4.966   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.145  -4.258   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.848  -5.088   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.918  -6.626   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       5.481  -4.380   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.410  -2.841   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.708  -2.011   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.637  -0.473   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.935   0.357   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.302  -0.351   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.599   0.479   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.372  -1.890   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.270   0.236   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.567   1.066   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.973  -0.594   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.043  -2.133   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.746  -2.963   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.605   0.114   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.147  -1.327   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.170  -2.518   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.712  -3.959   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.504  -2.427   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.308  -0.716   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.498  -1.693   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.057  -2.235   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.445  -3.726   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.466  -2.466   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.174  -3.833   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -1.156  -1.089   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -0.059  -0.008   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.129   1.531   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.168   2.361   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.098   3.899   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.535   1.652   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.832   2.482   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       3.762   4.021   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       5.500   5.333   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       6.867   4.625   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       4.989   6.389   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       6.286   7.219   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       6.216   8.758   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       5.200   1.774   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       6.497   2.604   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       6.427   4.142   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       5.059   4.851   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       7.724   4.972   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   17                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9   15   16   43                                             
CONECT   15   14                                                            
CONECT   16   14   17   19                                                  
CONECT   17   16    7   18                                                  
CONECT   18   17                                                            
CONECT   19   16   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   19   25   26   31                                             
CONECT   25   24   26                                                       
CONECT   26   25   24   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   24   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   37   43                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41                                                            
CONECT   43   36   14   44                                                  
CONECT   44   43   45                                                       
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45                                                            
MASTER        0    0    0    0    0    0    0    0   47    0  100    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₄H₄₈O₁₃

Average Mass

664.7450 Da

Monoisotopic Mass

664.30949 Da

IUPAC Name

(1R,2R,3S,4R,5S,7S,8S,9R,10S,12Z,14S,17R)-2,7,9-tris(acetyloxy)-5-(butanoyloxy)-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0^{1,17}.0^{3,8}]octadec-12-en-10-yl butanoate

Traditional Name

(1R,2R,3S,4R,5S,7S,8S,9R,10S,12Z,14S,17R)-2,7,9-tris(acetyloxy)-5-(butanoyloxy)-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0^{1,17}.0^{3,8}]octadec-12-en-10-yl butanoate

CAS Registry Number

Not Available

SMILES

CCCC(=O)O[C@H]1C[C@H](OC(C)=O)[C@]2(C)[C@H]([C@H]1C)[C@@H](OC(C)=O)[C@@]13O[C@@]1(C)C(=O)O[C@H]3\C=C(C)/C[C@H](OC(=O)CCC)[C@@H]2OC(C)=O

InChI Identifier

InChI=1S/C34H48O13/c1-10-12-26(38)44-22-16-24(41-19(5)35)32(8)28(18(22)4)30(43-21(7)37)34-25(46-31(40)33(34,9)47-34)15-17(3)14-23(29(32)42-20(6)36)45-27(39)13-11-2/h15,18,22-25,28-30H,10-14,16H2,1-9H3/b17-15-/t18-,22-,23-,24-,25-,28+,29-,30+,32+,33-,34+/m0/s1

InChI Key

ISQVFOAGBSWCLK-SMJOTQBDSA-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
Briareum excavatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Briarane diterpenoid
Hexacarboxylic acid or derivatives
Diterpenoid
Diterpene lactone
Fatty acid ester
Fatty acyl
Gamma butyrolactone
Para-dioxane
Tetrahydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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	3.23	ALOGPS
logP	3.37	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	170.33 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	160.97 m³·mol⁻¹	ChemAxon
Polarizability	74.8 Å³	ChemAxon
Number of Rings	4	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

C00049374

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

100967686

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r,3s,4r,5s,7s,8s,9r,10s,12z,14s,17r)-2,7,9-tris(acetyloxy)-5-(butanoyloxy)-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-12-en-10-yl butanoate (NP0161962)

MOL for NP0161962 ((1r,2r,3s,4r,5s,7s,8s,9r,10s,12z,14s,17r)-2,7,9-tris(acetyloxy)-5-(butanoyloxy)-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-12-en-10-yl butanoate)

3D MOL for NP0161962 ((1r,2r,3s,4r,5s,7s,8s,9r,10s,12z,14s,17r)-2,7,9-tris(acetyloxy)-5-(butanoyloxy)-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-12-en-10-yl butanoate)

3D SDF for NP0161962 ((1r,2r,3s,4r,5s,7s,8s,9r,10s,12z,14s,17r)-2,7,9-tris(acetyloxy)-5-(butanoyloxy)-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-12-en-10-yl butanoate)

3D-SDF for NP0161962 ((1r,2r,3s,4r,5s,7s,8s,9r,10s,12z,14s,17r)-2,7,9-tris(acetyloxy)-5-(butanoyloxy)-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-12-en-10-yl butanoate)

PDB for NP0161962 ((1r,2r,3s,4r,5s,7s,8s,9r,10s,12z,14s,17r)-2,7,9-tris(acetyloxy)-5-(butanoyloxy)-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-12-en-10-yl butanoate)

3D PDB for NP0161962 ((1r,2r,3s,4r,5s,7s,8s,9r,10s,12z,14s,17r)-2,7,9-tris(acetyloxy)-5-(butanoyloxy)-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-12-en-10-yl butanoate)

SMILES for NP0161962 ((1r,2r,3s,4r,5s,7s,8s,9r,10s,12z,14s,17r)-2,7,9-tris(acetyloxy)-5-(butanoyloxy)-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-12-en-10-yl butanoate)

INCHI for NP0161962 ((1r,2r,3s,4r,5s,7s,8s,9r,10s,12z,14s,17r)-2,7,9-tris(acetyloxy)-5-(butanoyloxy)-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-12-en-10-yl butanoate)

Structure for NP0161962 ((1r,2r,3s,4r,5s,7s,8s,9r,10s,12z,14s,17r)-2,7,9-tris(acetyloxy)-5-(butanoyloxy)-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-12-en-10-yl butanoate)

3D Structure for NP0161962 ((1r,2r,3s,4r,5s,7s,8s,9r,10s,12z,14s,17r)-2,7,9-tris(acetyloxy)-5-(butanoyloxy)-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-12-en-10-yl butanoate)