NP-MRD: Showing NP-Card for (1r,2s,3r,6r,7r,8r,9r,12s,13s)-3,13-dihydroxy-6-isopropyl-12-methoxy-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-9-yl acetate (NP0227798)

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Record Information

Version

2.0

Created at

2022-09-06 07:14:35 UTC

Updated at

2022-09-06 07:14:35 UTC

NP-MRD ID

NP0227798

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,3r,6r,7r,8r,9r,12s,13s)-3,13-dihydroxy-6-isopropyl-12-methoxy-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-9-yl acetate

Description

Palmonine C belongs to the class of organic compounds known as eunicellane and asbestinane diterpenoids. These are diterpenoids with a structure based on either the eunicellane (5,14-cyclocembrane) or the asbestinane skeleton. (1r,2s,3r,6r,7r,8r,9r,12s,13s)-3,13-dihydroxy-6-isopropyl-12-methoxy-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-9-yl acetate is found in Eunicella verrucosa. Based on a literature review very few articles have been published on palmonine C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062209142D          

 29 31  0  0  1  0            999 V2000
    7.0844    0.1043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9128    0.9112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1282    1.1662    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1282    1.9912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6433    2.6586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8587    2.9136    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3436    3.5810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3737    3.5810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7093    4.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2244    5.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5298    4.4209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0740    2.6586    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3440    1.5787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0740    0.4987    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8587    0.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6433    0.4987    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7979   -0.3117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3662    0.1013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5891    1.1662    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5891    1.9912    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8746    2.4037    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8746    3.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1602    3.6412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5891    3.6412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1602    1.9912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1602    1.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8746    0.7537    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4873    0.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2620    0.0252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  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  1  1  0  0  0
  6  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  1  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  3 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  1  0  0  0
 19 14  1  1  0  0  0
 20 19  1  1  0  0  0
 12 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 21 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  6  0  0  0
M  END

     RDKit          3D

 69 71  0  0  0  0  0  0  0  0999 V2000
   -4.5376   -1.0021   -2.7366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3625   -1.0614   -1.4065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0532   -0.7735   -0.9267 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1521    0.4616   -0.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0275    1.0085    0.6128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8760    1.5599   -0.1275 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4204    2.3295   -1.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1401    2.4199    0.7130 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5497    3.5681    1.3050 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3392    4.3870    2.1898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6992    3.9748    1.1212 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1152    0.5700   -0.6565 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3843   -0.6029   -1.0802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1502   -1.6182   -0.2115 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3775   -2.2068    0.4085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6539   -2.0264   -0.2713 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7580   -2.4276    0.7268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7533   -3.0304   -1.2761 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8262   -1.0818    0.8455 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2371    0.2429    0.3315 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5392    0.2054   -0.4189 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0783    1.5449   -0.7810 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3681    2.4518    0.3696 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3846    1.3289   -1.5400 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6021   -0.5887    0.2846 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0817   -2.0344    0.2552 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9024   -2.0514    1.1764 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3934   -3.4500    1.2860 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3937   -1.6996    2.4567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9180   -1.6881   -3.3464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5895   -1.3005   -2.9418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4389    0.0142   -3.1917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5392   -0.5710   -1.8987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4414    1.2804   -0.9021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0478    0.4223    0.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7295    0.3516    1.4793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4679    1.8722    1.1680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5568    2.9642   -1.6767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2831    2.9466   -1.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6619    1.6456   -2.1388 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2994    4.0167    3.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3593    4.4747    1.8042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0508    5.4446    2.2627 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6094    1.0684   -1.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4667   -2.3841   -0.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1790   -3.3300    0.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4185   -2.0074    1.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7106   -2.5897    0.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7944   -1.7309    1.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4253   -3.4103    1.1288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1883   -2.7701   -2.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2567   -0.9236    1.8102 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2454    0.9891    1.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3306   -0.3299   -1.3839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4292    2.1118   -1.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5747    2.5259    1.1101 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3534    2.1646    0.7939 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5192    3.4839   -0.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3943    0.3496   -2.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5145    2.0921   -2.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2322    1.3276   -0.8288 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5604   -0.4943   -0.2150 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6084   -0.2978    1.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8804   -2.6443    0.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8489   -2.3105   -0.7844 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2233   -4.0609    1.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1477   -3.9423    0.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5835   -3.4627    2.0468 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6376   -1.6956    3.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
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  5  6  1  0
  6  7  1  0
  6  8  1  1
  8  9  1  0
  9 10  1  0
  9 11  2  0
  6 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  6
 14 19  1  0
 19 20  1  0
 20 21  1  0
 21 25  1  0
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 26 27  1  0
 27 28  1  0
 27 29  1  1
 21 22  1  0
 22 23  1  0
 22 24  1  0
 16  3  1  0
 27 19  1  0
 20 12  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  6
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  7 38  1  0
  7 39  1  0
  7 40  1  0
 10 41  1  0
 10 42  1  0
 10 43  1  0
 12 44  1  6
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 15 47  1  0
 17 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 19 52  1  1
 20 53  1  1
 21 54  1  6
 25 62  1  0
 25 63  1  0
 26 64  1  0
 26 65  1  0
 28 66  1  0
 28 67  1  0
 28 68  1  0
 29 69  1  0
 22 55  1  0
 23 56  1  0
 23 57  1  0
 23 58  1  0
 24 59  1  0
 24 60  1  0
 24 61  1  0
M  END


  Mrv1652309062209142D          

 29 31  0  0  1  0            999 V2000
    7.0844    0.1043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9128    0.9112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1282    1.1662    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1282    1.9912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6433    2.6586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8587    2.9136    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3436    3.5810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3737    3.5810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7093    4.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2244    5.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5298    4.4209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0740    2.6586    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3440    1.5787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0740    0.4987    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8587    0.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6433    0.4987    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7979   -0.3117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3662    0.1013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5891    1.1662    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5891    1.9912    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8746    2.4037    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8746    3.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1602    3.6412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5891    3.6412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1602    1.9912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1602    1.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8746    0.7537    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4873    0.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2620    0.0252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  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  1  1  0  0  0
  6  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  1  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  3 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  1  0  0  0
 19 14  1  1  0  0  0
 20 19  1  1  0  0  0
 12 20  1  0  0  0  0
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 21 22  1  6  0  0  0
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 22 24  1  0  0  0  0
 21 25  1  0  0  0  0
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 19 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0227798

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C23H40O6/c1-13(2)15-8-10-21(4,25)19-16-12-22(5,26)17(27-7)9-11-23(6,29-14(3)24)20(28-16)18(15)19/h13,15-20,25-26H,8-12H2,1-7H3/t15-,16-,17+,18-,19-,20-,21-,22+,23-/m1/s1

> <INCHI_KEY>
PYEOWRXHJUEZKP-HUDPYBAISA-N

> <FORMULA>
C23H40O6

> <MOLECULAR_WEIGHT>
412.567

> <EXACT_MASS>
412.282489008

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
46.04650578303084

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,3R,6R,7R,8R,9R,12S,13S)-3,13-dihydroxy-12-methoxy-3,9,13-trimethyl-6-(propan-2-yl)-15-oxatricyclo[6.6.1.0^{2,7}]pentadecan-9-yl acetate

> <JCHEM_LOGP>
1.9794174780000005

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.770137649477718

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.897617890590038

> <JCHEM_PKA_STRONGEST_BASIC>
-2.932471160773261

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
109.61699999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3R,6R,7R,8R,9R,12S,13S)-3,13-dihydroxy-6-isopropyl-12-methoxy-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0^{2,7}]pentadecan-9-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      13.224   0.195   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.904   1.701   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.439   2.177   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.439   3.717   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.534   4.963   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.070   5.439   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.975   6.685   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.164   6.685   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.791   8.091   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.885   9.337   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.322   8.252   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.605   4.963   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.109   2.947   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       7.605   0.931   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.070   0.455   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.534   0.931   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.823  -0.582   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      11.884   0.189   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.700   2.177   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.700   3.717   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.366   4.487   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.366   6.027   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.032   6.797   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.700   6.797   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.032   3.717   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.032   2.177   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.366   1.407   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.643   0.047   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.089   0.047   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   16                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   12                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    6   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15    3   17   18                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   14   20   27                                                  
CONECT   20   19   12   21                                                  
CONECT   21   20   22   25                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   21   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   19   28   29                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₄₀O₆

Average Mass

412.5670 Da

Monoisotopic Mass

412.28249 Da

IUPAC Name

(1R,2S,3R,6R,7R,8R,9R,12S,13S)-3,13-dihydroxy-12-methoxy-3,9,13-trimethyl-6-(propan-2-yl)-15-oxatricyclo[6.6.1.0^{2,7}]pentadecan-9-yl acetate

Traditional Name

(1R,2S,3R,6R,7R,8R,9R,12S,13S)-3,13-dihydroxy-6-isopropyl-12-methoxy-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0^{2,7}]pentadecan-9-yl acetate

CAS Registry Number

Not Available

SMILES

CO[C@H]1CC[C@@](C)(OC(C)=O)[C@@H]2O[C@H](C[C@]1(C)O)[C@@H]1[C@H]2[C@H](CC[C@@]1(C)O)C(C)C

InChI Identifier

InChI=1S/C23H40O6/c1-13(2)15-8-10-21(4,25)19-16-12-22(5,26)17(27-7)9-11-23(6,29-14(3)24)20(28-16)18(15)19/h13,15-20,25-26H,8-12H2,1-7H3/t15-,16-,17+,18-,19-,20-,21-,22+,23-/m1/s1

InChI Key

PYEOWRXHJUEZKP-HUDPYBAISA-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
Eunicella verrucosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eunicellane and asbestinane diterpenoids. These are diterpenoids with a structure based on either the eunicellane (5,14-cyclocembrane) or the asbestinane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Eunicellane and asbestinane diterpenoids

Alternative Parents

Substituents

Cladiellane diterpenoid
Eunicellane-type diterpenoid
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Carboxylic acid ester
Carboxylic acid derivative
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxygen compound
Organic oxide
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	1.98	ChemAxon
pKa (Strongest Acidic)	13.9	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	109.62 m³·mol⁻¹	ChemAxon
Polarizability	46.05 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

23327349

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44559763

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,3r,6r,7r,8r,9r,12s,13s)-3,13-dihydroxy-6-isopropyl-12-methoxy-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-9-yl acetate (NP0227798)

MOL for NP0227798 ((1r,2s,3r,6r,7r,8r,9r,12s,13s)-3,13-dihydroxy-6-isopropyl-12-methoxy-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-9-yl acetate)

3D MOL for NP0227798 ((1r,2s,3r,6r,7r,8r,9r,12s,13s)-3,13-dihydroxy-6-isopropyl-12-methoxy-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-9-yl acetate)

3D SDF for NP0227798 ((1r,2s,3r,6r,7r,8r,9r,12s,13s)-3,13-dihydroxy-6-isopropyl-12-methoxy-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-9-yl acetate)

3D-SDF for NP0227798 ((1r,2s,3r,6r,7r,8r,9r,12s,13s)-3,13-dihydroxy-6-isopropyl-12-methoxy-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-9-yl acetate)

PDB for NP0227798 ((1r,2s,3r,6r,7r,8r,9r,12s,13s)-3,13-dihydroxy-6-isopropyl-12-methoxy-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-9-yl acetate)

3D PDB for NP0227798 ((1r,2s,3r,6r,7r,8r,9r,12s,13s)-3,13-dihydroxy-6-isopropyl-12-methoxy-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-9-yl acetate)

SMILES for NP0227798 ((1r,2s,3r,6r,7r,8r,9r,12s,13s)-3,13-dihydroxy-6-isopropyl-12-methoxy-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-9-yl acetate)

INCHI for NP0227798 ((1r,2s,3r,6r,7r,8r,9r,12s,13s)-3,13-dihydroxy-6-isopropyl-12-methoxy-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-9-yl acetate)

Structure for NP0227798 ((1r,2s,3r,6r,7r,8r,9r,12s,13s)-3,13-dihydroxy-6-isopropyl-12-methoxy-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-9-yl acetate)

3D Structure for NP0227798 ((1r,2s,3r,6r,7r,8r,9r,12s,13s)-3,13-dihydroxy-6-isopropyl-12-methoxy-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-9-yl acetate)