NP-MRD: Showing NP-Card for (1's,2r,2's,3'r,4'r,7'r,8's,12's,13's,14'r,15'r,16'r)-2',14',15',16'-tetrakis(acetyloxy)-8'-chloro-3'-hydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-12'-yl acetate (NP0292950)

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Record Information

Version

2.0

Created at

2022-09-10 00:43:27 UTC

Updated at

2022-09-10 00:43:27 UTC

NP-MRD ID

NP0292950

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1's,2r,2's,3'r,4'r,7'r,8's,12's,13's,14'r,15'r,16'r)-2',14',15',16'-tetrakis(acetyloxy)-8'-chloro-3'-hydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-12'-yl acetate

Description

Gemmacolide A belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (1's,2r,2's,3'r,4'r,7'r,8's,12's,13's,14'r,15'r,16'r)-2',14',15',16'-tetrakis(acetyloxy)-8'-chloro-3'-hydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-12'-yl acetate is found in Dichotella gemmacea and Junceella juncea. Based on a literature review very few articles have been published on Gemmacolide A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102202432D          

 45 48  0  0  1  0            999 V2000
    2.2728   -1.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2352   -0.3127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5027    0.0668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8077   -0.3778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0752    0.0017    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6197   -0.4429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5821   -1.2671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1504   -1.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2770   -1.7117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0376    0.8259    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6573    0.3812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7325    1.2705    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4651    0.8910    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2701    1.5428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9500    2.3171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6853    3.0985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7591    2.1556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1600    1.3356    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4711    1.7896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2946    2.1496    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7151    2.7369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1102    2.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4898    3.0057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4798    1.5355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0744    2.8272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0376    2.4741    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.8453    4.5019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8077    3.6778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6949    1.2054    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3899    0.7607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1224    1.1402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8173    0.6956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1600    1.9644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  5 10  1  0  0  0  0
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 38 40  2  0  0  0  0
 36 41  1  0  0  0  0
 10 41  1  0  0  0  0
 41 42  1  1  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  2  0  0  0  0
M  END

     RDKit          3D

 84 87  0  0  0  0  0  0  0  0999 V2000
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   -1.6029   -2.2263    0.4033 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5333   -3.0805    0.3395 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8375   -4.0121   -0.6088 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6168   -5.2048   -0.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2779   -0.1545   -0.4603 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.4214    3.0694    0.2997 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2770    1.5443   -0.3794 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2388    1.4703   -1.7765 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5972    3.2644   -2.0027 O   0  0  0  0  0  0  0  0  0  0  0  0
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 16 61  1  0
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 19 64  1  0
M  END


  Mrv1652309102202432D          

 45 48  0  0  1  0            999 V2000
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    0.7325    1.2705    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4651    0.8910    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2701    1.5428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9500    2.3171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6853    3.0985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7591    2.1556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1600    1.3356    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4711    1.7896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2946    2.1496    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7151    2.7369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1102    2.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4898    3.0057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4798    1.5355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8925    0.9561    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9301    0.1320    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6627   -0.2475    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.6949    2.0946    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0744    2.8272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5191    2.1322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0376    2.4741    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0752    3.2983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0663    3.9137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7386    2.9746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8453    4.5019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7325    2.0295    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4651    2.4090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5027    3.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2352    3.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8077    3.6778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6949    1.2054    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3899    0.7607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1224    1.1402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8173    0.6956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1600    1.9644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 25 24  1  1  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
  2 26  1  0  0  0  0
 26 27  1  1  0  0  0
 12 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 30  1  1  0  0  0
 28 31  1  0  0  0  0
 31 32  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 31 36  1  0  0  0  0
 36 37  1  1  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  2  0  0  0  0
 36 41  1  0  0  0  0
 10 41  1  0  0  0  0
 41 42  1  1  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0292950

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C(=O)O[C@H]2[C@@H](Cl)C(=C)CC[C@H](OC(C)=O)[C@@]3(C)[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@]4(CO4)[C@@H]3[C@H](OC(C)=O)[C@]12O

> <INCHI_IDENTIFIER>
InChI=1S/C30H39ClO14/c1-12-9-10-19(40-14(3)32)28(8)22(26(44-18(7)36)30(38)13(2)27(37)45-23(30)20(12)31)29(11-39-29)25(43-17(6)35)21(41-15(4)33)24(28)42-16(5)34/h13,19-26,38H,1,9-11H2,2-8H3/t13-,19-,20-,21+,22+,23-,24-,25+,26-,28+,29-,30-/m0/s1

> <INCHI_KEY>
RVARBBKIGSFITE-BRDFTBFESA-N

> <FORMULA>
C30H39ClO14

> <MOLECULAR_WEIGHT>
659.08

> <EXACT_MASS>
658.2028336

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
63.199927967066856

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'S,2R,2'S,3'R,4'R,7'R,8'S,12'S,13'S,14'R,15'R,16'R)-2',14',15',16'-tetrakis(acetyloxy)-8'-chloro-3'-hydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0^{3,7}]heptadecane]-12'-yl acetate

> <JCHEM_LOGP>
0.4640236323333331

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.368117523588548

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9499853951823676

> <JCHEM_POLAR_SURFACE_AREA>
190.55999999999997

> <JCHEM_REFRACTIVITY>
147.0841

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2R,2'S,3'R,4'R,7'R,8'S,12'S,13'S,14'R,15'R,16'R)-2',14',15',16'-tetrakis(acetyloxy)-8'-chloro-3'-hydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0^{3,7}]heptadecane]-12'-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       4.243  -2.122   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.172  -0.584   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.805   0.125   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.508  -0.705   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.140   0.003   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.157  -0.827   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.087  -2.365   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.281  -3.074   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.384  -3.195   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.070   1.542   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.227   0.712   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.367   2.372   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.735   1.663   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.371   2.880   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.640   4.325   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.146   5.784   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.150   4.024   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.032   2.493   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.746   3.341   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.283   4.013   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.202   5.109   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.806   4.243   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.514   5.611   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.496   2.866   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.399   1.785   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.470   0.246   0.000  0.00  0.00           C+0
HETATM   27 Cl   UNK     0       6.837  -0.462   0.000  0.00  0.00          Cl+0
HETATM   28  C   UNK     0       1.297   3.910   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.006   5.277   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.836   3.980   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -0.070   4.618   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -0.140   6.157   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.990   7.306   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.245   5.553   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -1.578   8.404   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -1.367   3.788   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -2.735   4.497   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -2.805   6.035   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -4.172   6.744   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -1.508   6.865   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -1.297   2.250   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -2.594   1.420   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -3.962   2.128   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -5.259   1.298   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      -4.032   3.667   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   26                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5   11   12   41                                             
CONECT   11   10                                                            
CONECT   12   10   13   28                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13   19   20   25                                             
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   18   26                                                  
CONECT   26   25    2   27                                                  
CONECT   27   26                                                            
CONECT   28   12   29   30   31                                             
CONECT   29   28   30                                                       
CONECT   30   29   28                                                       
CONECT   31   28   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   31   37   41                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
CONECT   41   36   10   42                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43                                                            
MASTER        0    0    0    0    0    0    0    0   45    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₉ClO₁₄

Average Mass

659.0800 Da

Monoisotopic Mass

658.20283 Da

IUPAC Name

(1'S,2R,2'S,3'R,4'R,7'R,8'S,12'S,13'S,14'R,15'R,16'R)-2',14',15',16'-tetrakis(acetyloxy)-8'-chloro-3'-hydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0^{3,7}]heptadecane]-12'-yl acetate

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@H]1C(=O)O[C@H]2[C@@H](Cl)C(=C)CC[C@H](OC(C)=O)[C@@]3(C)[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@]4(CO4)[C@@H]3[C@H](OC(C)=O)[C@]12O

InChI Identifier

InChI=1S/C30H39ClO14/c1-12-9-10-19(40-14(3)32)28(8)22(26(44-18(7)36)30(38)13(2)27(37)45-23(30)20(12)31)29(11-39-29)25(43-17(6)35)21(41-15(4)33)24(28)42-16(5)34/h13,19-26,38H,1,9-11H2,2-8H3/t13-,19-,20-,21+,22+,23-,24-,25+,26-,28+,29-,30-/m0/s1

InChI Key

RVARBBKIGSFITE-BRDFTBFESA-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
Dichotella gemmacea	LOTUS Database	35616633
Junceella juncea	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

Diterpene lactone
Diterpenoid
Hexacarboxylic acid or derivatives
Briarane diterpenoid
Gamma butyrolactone
Tertiary alcohol
Tetrahydrofuran
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Carboxylic acid derivative
Dialkyl ether
Oxacycle
Oxirane
Ether
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organohalogen compound
Organochloride
Organooxygen compound
Carbonyl group
Alkyl halide
Alkyl chloride
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	0.46	ChemAxon
pKa (Strongest Acidic)	12.37	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	190.56 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	147.08 m³·mol⁻¹	ChemAxon
Polarizability	63.2 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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

C00031807

Chemspider ID

10473000

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15060793

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1's,2r,2's,3'r,4'r,7'r,8's,12's,13's,14'r,15'r,16'r)-2',14',15',16'-tetrakis(acetyloxy)-8'-chloro-3'-hydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-12'-yl acetate (NP0292950)

MOL for NP0292950 ((1's,2r,2's,3'r,4'r,7'r,8's,12's,13's,14'r,15'r,16'r)-2',14',15',16'-tetrakis(acetyloxy)-8'-chloro-3'-hydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-12'-yl acetate)

3D MOL for NP0292950 ((1's,2r,2's,3'r,4'r,7'r,8's,12's,13's,14'r,15'r,16'r)-2',14',15',16'-tetrakis(acetyloxy)-8'-chloro-3'-hydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-12'-yl acetate)

3D SDF for NP0292950 ((1's,2r,2's,3'r,4'r,7'r,8's,12's,13's,14'r,15'r,16'r)-2',14',15',16'-tetrakis(acetyloxy)-8'-chloro-3'-hydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-12'-yl acetate)

3D-SDF for NP0292950 ((1's,2r,2's,3'r,4'r,7'r,8's,12's,13's,14'r,15'r,16'r)-2',14',15',16'-tetrakis(acetyloxy)-8'-chloro-3'-hydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-12'-yl acetate)

PDB for NP0292950 ((1's,2r,2's,3'r,4'r,7'r,8's,12's,13's,14'r,15'r,16'r)-2',14',15',16'-tetrakis(acetyloxy)-8'-chloro-3'-hydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-12'-yl acetate)

3D PDB for NP0292950 ((1's,2r,2's,3'r,4'r,7'r,8's,12's,13's,14'r,15'r,16'r)-2',14',15',16'-tetrakis(acetyloxy)-8'-chloro-3'-hydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-12'-yl acetate)

SMILES for NP0292950 ((1's,2r,2's,3'r,4'r,7'r,8's,12's,13's,14'r,15'r,16'r)-2',14',15',16'-tetrakis(acetyloxy)-8'-chloro-3'-hydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-12'-yl acetate)

INCHI for NP0292950 ((1's,2r,2's,3'r,4'r,7'r,8's,12's,13's,14'r,15'r,16'r)-2',14',15',16'-tetrakis(acetyloxy)-8'-chloro-3'-hydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-12'-yl acetate)

Structure for NP0292950 ((1's,2r,2's,3'r,4'r,7'r,8's,12's,13's,14'r,15'r,16'r)-2',14',15',16'-tetrakis(acetyloxy)-8'-chloro-3'-hydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-12'-yl acetate)

3D Structure for NP0292950 ((1's,2r,2's,3'r,4'r,7'r,8's,12's,13's,14'r,15'r,16'r)-2',14',15',16'-tetrakis(acetyloxy)-8'-chloro-3'-hydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-12'-yl acetate)