NP-MRD: Showing NP-Card for (1'r,2r,2's,3's,7's,8'r,9'r,10's,11's,13's,14'r,17'r)-7',9',10'-tris(acetyloxy)-13'-chloro-8',17'-dimethyl-12'-methylidene-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan]-2'-yl acetate (NP0265844)

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Record Information

Version

2.0

Created at

2022-09-08 09:58:40 UTC

Updated at

2022-09-08 09:58:40 UTC

NP-MRD ID

NP0265844

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1'r,2r,2's,3's,7's,8'r,9'r,10's,11's,13's,14'r,17'r)-7',9',10'-tris(acetyloxy)-13'-chloro-8',17'-dimethyl-12'-methylidene-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan]-2'-yl acetate

Description

Praelolide belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups. (1'r,2r,2's,3's,7's,8'r,9'r,10's,11's,13's,14'r,17'r)-7',9',10'-tris(acetyloxy)-13'-chloro-8',17'-dimethyl-12'-methylidene-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan]-2'-yl acetate is found in Dichotella gemmacea and Junceella fragilis. (1'r,2r,2's,3's,7's,8'r,9'r,10's,11's,13's,14'r,17'r)-7',9',10'-tris(acetyloxy)-13'-chloro-8',17'-dimethyl-12'-methylidene-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan]-2'-yl acetate was first documented in 2003 (PMID: 14646324). Based on a literature review a small amount of articles have been published on Praelolide (PMID: 29932137) (PMID: 15568788) (PMID: 22647719) (PMID: 18774864).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082211582D          

 41 45  0  0  1  0            999 V2000
    0.8479    4.4907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1873    3.6827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2559    0.6120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7867   -0.1623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6214   -1.0327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4665    2.4522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  5 39  1  0  0  0  0
 39 40  1  0  0  0  0
  2 40  1  0  0  0  0
 40 41  1  1  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309082211582D          

 41 45  0  0  1  0            999 V2000
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    4.0033    4.0557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3686    4.9150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1537    5.7504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1442    5.3257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8610    3.6390    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5368    4.4667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0220    5.1857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1699    5.1107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1270    6.0402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5640    0.1069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8846    0.5750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4653    1.1327    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8893    0.3178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6489    0.9663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1801    0.6087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2438    1.6840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8201    2.2830    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5714    3.1058    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2675    3.3042    0.0000 Cl  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  1  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 15 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 22 27  1  0  0  0  0
  3 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 12 32  1  0  0  0  0
 32 33  1  0  0  0  0
 12 33  1  1  0  0  0
  5 34  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 39 38  1  1  0  0  0
  5 39  1  0  0  0  0
 39 40  1  0  0  0  0
  2 40  1  0  0  0  0
 40 41  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0265844

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C(=O)O[C@H]2[C@@H](Cl)C(=C)[C@@H]3O[C@@]12[C@@H](OC(C)=O)[C@H]1[C@@]2(CO2)CC[C@H](OC(C)=O)[C@]1(C)[C@@H](OC(C)=O)[C@H]3OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H35ClO12/c1-11-18(29)22-28(12(2)25(34)40-22)24(39-16(6)33)21-26(7,17(36-13(3)30)8-9-27(21)10-35-27)23(38-15(5)32)20(19(11)41-28)37-14(4)31/h12,17-24H,1,8-10H2,2-7H3/t12-,17-,18-,19-,20-,21+,22-,23-,24-,26-,27-,28-/m0/s1

> <INCHI_KEY>
VPXKDKFGKRSWEO-JBTNVLFLSA-N

> <FORMULA>
C28H35ClO12

> <MOLECULAR_WEIGHT>
599.03

> <EXACT_MASS>
598.1817043

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
57.77723208253458

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'R,2R,2'S,3'S,7'S,8'R,9'R,10'S,11'S,13'S,14'R,17'R)-7',9',10'-tris(acetyloxy)-13'-chloro-8',17'-dimethyl-12'-methylidene-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[9.6.1.0^{1,14}.0^{3,8}]octadecane]-2'-yl acetate

> <JCHEM_LOGP>
1.028694334333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.938321846937751

> <JCHEM_POLAR_SURFACE_AREA>
153.26

> <JCHEM_REFRACTIVITY>
134.57649999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,2R,2'S,3'S,7'S,8'R,9'R,10'S,11'S,13'S,14'R,17'R)-7',9',10'-tris(acetyloxy)-13'-chloro-8',17'-dimethyl-12'-methylidene-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[9.6.1.0^{1,14}.0^{3,8}]octadecane]-2'-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       1.583   8.383   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.216   6.874   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.769   6.476   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.508   5.028   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.075   3.690   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.538   2.880   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.211   1.142   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.335  -0.303   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.698   1.091   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.027  -1.928   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.114   3.125   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.775   1.735   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.311   1.612   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.184   2.880   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.523   4.271   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.204   4.578   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      11.823   4.868   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.655   6.264   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      13.078   3.921   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.988   4.393   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.133   5.513   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.676   5.952   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.473   7.571   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.155   9.175   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.753  10.734   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.603   9.941   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.341   6.793   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.735   8.338   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.774   9.680   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.184   9.540   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.970  11.275   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.653   0.199   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       5.385   1.073   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.735   2.114   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.660   0.593   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.211   1.804   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -0.336   1.136   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       0.455   3.143   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       1.531   4.262   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       1.067   5.798   0.000  0.00  0.00           C+0
HETATM   41 Cl   UNK     0      -0.499   6.168   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3   40                                                  
CONECT    3    2    4   27                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   34   39                                             
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    6   12   20                                                  
CONECT   12   11   13   32   33                                             
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   15   11   21   22                                             
CONECT   21   20                                                            
CONECT   22   20   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   22    3   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   12   33                                                       
CONECT   33   32   12                                                       
CONECT   34    5   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38    5   40                                                  
CONECT   40   39    2   41                                                  
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

View in JSmol

Synonyms

Value	Source
Prelolide	MeSH

Chemical Formula

C₂₈H₃₅ClO₁₂

Average Mass

599.0300 Da

Monoisotopic Mass

598.18170 Da

IUPAC Name

(1'R,2R,2'S,3'S,7'S,8'R,9'R,10'S,11'S,13'S,14'R,17'R)-7',9',10'-tris(acetyloxy)-13'-chloro-8',17'-dimethyl-12'-methylidene-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[9.6.1.0^{1,14}.0^{3,8}]octadecane]-2'-yl acetate

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@H]1C(=O)O[C@H]2[C@@H](Cl)C(=C)[C@@H]3O[C@@]12[C@@H](OC(C)=O)[C@H]1[C@@]2(CO2)CC[C@H](OC(C)=O)[C@]1(C)[C@@H](OC(C)=O)[C@H]3OC(C)=O

InChI Identifier

InChI=1S/C28H35ClO12/c1-11-18(29)22-28(12(2)25(34)40-22)24(39-16(6)33)21-26(7,17(36-13(3)30)8-9-27(21)10-35-27)23(38-15(5)32)20(19(11)41-28)37-14(4)31/h12,17-24H,1,8-10H2,2-7H3/t12-,17-,18-,19-,20-,21+,22-,23-,24-,26-,27-,28-/m0/s1

InChI Key

VPXKDKFGKRSWEO-JBTNVLFLSA-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 fragilis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Pentacarboxylic acids and derivatives

Direct Parent

Pentacarboxylic acids and derivatives

Alternative Parents

Substituents

Pentacarboxylic acid or derivatives
Furopyran
Gamma butyrolactone
Pyran
Oxane
Furan
Tetrahydrofuran
Carboxylic acid ester
Lactone
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Alkyl halide
Alkyl chloride
Carbonyl group
Organic oxygen compound
Organohalogen compound
Organochloride
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.03	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	153.26 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	134.58 m³·mol⁻¹	ChemAxon
Polarizability	57.78 Å³	ChemAxon
Number of Rings	5	ChemAxon
Rule of Five	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00031077

Chemspider ID

23326441

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14264086

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zheng LG, Chang YC, Hu CC, Wen ZH, Wu YC, Sung PJ: Fragilides K and L, New Briaranes from the Gorgonian Coral Junceella fragilis. Molecules. 2018 Jun 22;23(7). pii: molecules23071510. doi: 10.3390/molecules23071510. [PubMed:29932137 ]
Qi SH, Zhang S, Huang H, Xiao ZH, Huang JS, Li QX: New briaranes from the South China Sea gorgonian Junceella juncea. J Nat Prod. 2004 Nov;67(11):1907-10. doi: 10.1021/np049848h. [PubMed:15568788 ]
Li C, La MP, Tang H, Pan WH, Sun P, Krohn K, Yi YH, Li L, Zhang W: Bioactive briarane diterpenoids from the South China Sea gorgonian Dichotella gemmacea. Bioorg Med Chem Lett. 2012 Jul 1;22(13):4368-72. doi: 10.1016/j.bmcl.2012.05.001. Epub 2012 May 9. [PubMed:22647719 ]
Liaw CC, Shen YC, Lin YS, Hwang TL, Kuo YH, Khalil AT: Frajunolides E-K, briarane diterpenes from Junceella fragilis. J Nat Prod. 2008 Sep;71(9):1551-6. doi: 10.1021/np800126f. Epub 2008 Sep 6. [PubMed:18774864 ]
Sung PJ, Fan TY, Fang LS, Wu SL, Li JJ, Chen MC, Cheng YM, Wang GH: Briarane derivatives from the gorgonian coral Junceella fragilis. Chem Pharm Bull (Tokyo). 2003 Dec;51(12):1429-31. doi: 10.1248/cpb.51.1429. [PubMed:14646324 ]
LOTUS database [Link]

Showing NP-Card for (1'r,2r,2's,3's,7's,8'r,9'r,10's,11's,13's,14'r,17'r)-7',9',10'-tris(acetyloxy)-13'-chloro-8',17'-dimethyl-12'-methylidene-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan]-2'-yl acetate (NP0265844)

MOL for NP0265844 ((1'r,2r,2's,3's,7's,8'r,9'r,10's,11's,13's,14'r,17'r)-7',9',10'-tris(acetyloxy)-13'-chloro-8',17'-dimethyl-12'-methylidene-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan]-2'-yl acetate)

3D MOL for NP0265844 ((1'r,2r,2's,3's,7's,8'r,9'r,10's,11's,13's,14'r,17'r)-7',9',10'-tris(acetyloxy)-13'-chloro-8',17'-dimethyl-12'-methylidene-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan]-2'-yl acetate)

3D SDF for NP0265844 ((1'r,2r,2's,3's,7's,8'r,9'r,10's,11's,13's,14'r,17'r)-7',9',10'-tris(acetyloxy)-13'-chloro-8',17'-dimethyl-12'-methylidene-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan]-2'-yl acetate)

3D-SDF for NP0265844 ((1'r,2r,2's,3's,7's,8'r,9'r,10's,11's,13's,14'r,17'r)-7',9',10'-tris(acetyloxy)-13'-chloro-8',17'-dimethyl-12'-methylidene-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan]-2'-yl acetate)

PDB for NP0265844 ((1'r,2r,2's,3's,7's,8'r,9'r,10's,11's,13's,14'r,17'r)-7',9',10'-tris(acetyloxy)-13'-chloro-8',17'-dimethyl-12'-methylidene-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan]-2'-yl acetate)

3D PDB for NP0265844 ((1'r,2r,2's,3's,7's,8'r,9'r,10's,11's,13's,14'r,17'r)-7',9',10'-tris(acetyloxy)-13'-chloro-8',17'-dimethyl-12'-methylidene-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan]-2'-yl acetate)

SMILES for NP0265844 ((1'r,2r,2's,3's,7's,8'r,9'r,10's,11's,13's,14'r,17'r)-7',9',10'-tris(acetyloxy)-13'-chloro-8',17'-dimethyl-12'-methylidene-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan]-2'-yl acetate)

INCHI for NP0265844 ((1'r,2r,2's,3's,7's,8'r,9'r,10's,11's,13's,14'r,17'r)-7',9',10'-tris(acetyloxy)-13'-chloro-8',17'-dimethyl-12'-methylidene-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan]-2'-yl acetate)

Structure for NP0265844 ((1'r,2r,2's,3's,7's,8'r,9'r,10's,11's,13's,14'r,17'r)-7',9',10'-tris(acetyloxy)-13'-chloro-8',17'-dimethyl-12'-methylidene-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan]-2'-yl acetate)

3D Structure for NP0265844 ((1'r,2r,2's,3's,7's,8'r,9'r,10's,11's,13's,14'r,17'r)-7',9',10'-tris(acetyloxy)-13'-chloro-8',17'-dimethyl-12'-methylidene-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan]-2'-yl acetate)