NP-MRD: Showing NP-Card for (1r,2s,3s,4r,5s,7s,8r,9r,10s,11e,13s,14s,17r)-2,7,9-tris(acetyloxy)-5,13-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-11-en-10-yl butanoate (NP0222237)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 00:01:35 UTC

Updated at

2022-09-06 00:01:35 UTC

NP-MRD ID

NP0222237

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,3s,4r,5s,7s,8r,9r,10s,11e,13s,14s,17r)-2,7,9-tris(acetyloxy)-5,13-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-11-en-10-yl butanoate

Description

(1R,2S,3S,4R,5S,7S,8R,9R,10S,11E,13S,14S,17R)-2,7,9-tris(acetyloxy)-5,13-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]Octadec-11-en-10-yl butanoate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (1r,2s,3s,4r,5s,7s,8r,9r,10s,11e,13s,14s,17r)-2,7,9-tris(acetyloxy)-5,13-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-11-en-10-yl butanoate is found in Briareum excavatum. Based on a literature review very few articles have been published on (1R,2S,3S,4R,5S,7S,8R,9R,10S,11E,13S,14S,17R)-2,7,9-tris(acetyloxy)-5,13-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]Octadec-11-en-10-yl butanoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062202012D          

 43 46  0  0  1  0            999 V2000
    3.1948   -4.3014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2295   -3.4772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5330   -3.0350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8861   -2.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6173   -1.6830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8713   -1.7685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9060   -0.9442    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2096   -0.5020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4784   -0.8840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4436   -1.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2181   -0.4418    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9493   -0.8239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1834    0.3824    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7727    0.9598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4057    1.6987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7877    2.4299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5165    1.6265    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6158    2.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1836    1.2902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5478    0.7645    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2443    0.3223    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5321    1.0955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0063    1.7313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1928    1.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2941    2.5045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9755    0.7043    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0102    1.5286    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3138    1.9708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7415    1.9107    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7762    2.7349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4379    1.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4032    0.6442    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0997    0.2020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8309    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8656    1.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5273    0.1418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6720    0.2621    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3685   -0.1801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6372   -0.5622    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3337   -1.0044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2990   -1.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9955   -2.2709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5678   -2.2107    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  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 20 19  1  6  0  0  0
 13 20  1  0  0  0  0
 17 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
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 32 37  1  0  0  0  0
 26 37  1  0  0  0  0
 37 38  1  1  0  0  0
 37 39  1  0  0  0  0
  7 39  1  0  0  0  0
 39 40  1  1  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  2  0  0  0  0
M  END


  Mrv1652309062202012D          

 43 46  0  0  1  0            999 V2000
    3.1948   -4.3014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2295   -3.4772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5330   -3.0350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8861   -2.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6173   -1.6830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8713   -1.7685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9060   -0.9442    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2096   -0.5020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4784   -0.8840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4436   -1.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2181   -0.4418    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9493   -0.8239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1834    0.3824    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7727    0.9598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4057    1.6987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7877    2.4299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5165    1.6265    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6158    2.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1836    1.2902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5478    0.7645    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2443    0.3223    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5321    1.0955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0063    1.7313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1928    1.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2941    2.5045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9755    0.7043    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0102    1.5286    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3138    1.9708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7415    1.9107    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7762    2.7349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4379    1.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4032    0.6442    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0997    0.2020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8309    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8656    1.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5273    0.1418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6720    0.2621    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3685   -0.1801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6372   -0.5622    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3337   -1.0044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2990   -1.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9955   -2.2709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5678   -2.2107    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  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 20 19  1  6  0  0  0
 13 20  1  0  0  0  0
 17 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
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 32 37  1  0  0  0  0
 26 37  1  0  0  0  0
 37 38  1  1  0  0  0
 37 39  1  0  0  0  0
  7 39  1  0  0  0  0
 39 40  1  1  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0222237

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC(=O)O[C@H]1\C=C(C)\[C@H](O)[C@@H]2OC(=O)[C@]3(C)O[C@]23[C@@H](OC(C)=O)[C@H]2[C@@H](C)[C@@H](O)C[C@H](OC(C)=O)[C@]2(C)[C@H]1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H42O13/c1-9-10-21(35)41-19-11-13(2)23(36)26-30(29(8,43-30)27(37)42-26)25(40-17(6)33)22-14(3)18(34)12-20(38-15(4)31)28(22,7)24(19)39-16(5)32/h11,14,18-20,22-26,34,36H,9-10,12H2,1-8H3/b13-11+/t14-,18-,19-,20-,22+,23-,24-,25-,26-,28-,29-,30+/m0/s1

> <INCHI_KEY>
VACOXDJECSFREG-DBJWEONTSA-N

> <FORMULA>
C30H42O13

> <MOLECULAR_WEIGHT>
610.653

> <EXACT_MASS>
610.262541412

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
61.22119032975238

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,3S,4R,5S,7S,8R,9R,10S,11E,13S,14S,17R)-2,7,9-tris(acetyloxy)-5,13-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0^{1,17}.0^{3,8}]octadec-11-en-10-yl butanoate

> <JCHEM_LOGP>
0.8660498933333327

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.87640512370578

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.465385536730633

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8607039270924464

> <JCHEM_POLAR_SURFACE_AREA>
184.48999999999998

> <JCHEM_REFRACTIVITY>
143.79640000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3S,4R,5S,7S,8R,9R,10S,11E,13S,14S,17R)-2,7,9-tris(acetyloxy)-5,13-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0^{1,17}.0^{3,8}]octadec-11-en-10-yl butanoate

> <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       5.964  -8.029   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.028  -6.491   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.728  -5.665   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.387  -3.855   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.752  -3.142   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       3.493  -3.301   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.558  -1.763   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.258  -0.937   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.893  -1.650   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.828  -3.189   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.407  -0.825   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.772  -1.538   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.342   0.714   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.442   1.792   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.757   3.171   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.470   4.536   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.964   3.036   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.149   4.437   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.209   2.408   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.023   1.427   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.323   0.602   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.860   2.045   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.878   3.232   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.360   2.975   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.416   4.675   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.688   1.315   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.752   2.853   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.452   3.679   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.117   3.567   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.182   5.105   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.417   2.741   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.353   1.202   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.653   0.377   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       9.018   1.090   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.082   2.629   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      10.318   0.265   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       4.988   0.489   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.288  -0.336   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.923  -1.049   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       6.223  -1.875   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       6.158  -3.413   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       7.458  -4.239   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       4.793  -4.127   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   39                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   13   17   21                                             
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   21   27   37                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   32   26   38   39                                             
CONECT   38   37                                                            
CONECT   39   37    7   40                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   92    0
END

View in JSmol

Synonyms

Value	Source
(1R,2S,3S,4R,5S,7S,8R,9R,10S,11E,13S,14S,17R)-2,7,9-Tris(acetyloxy)-5,13-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0,.0,]octadec-11-en-10-yl butanoic acid	Generator

Chemical Formula

C₃₀H₄₂O₁₃

Average Mass

610.6530 Da

Monoisotopic Mass

610.26254 Da

IUPAC Name

(1R,2S,3S,4R,5S,7S,8R,9R,10S,11E,13S,14S,17R)-2,7,9-tris(acetyloxy)-5,13-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0^{1,17}.0^{3,8}]octadec-11-en-10-yl butanoate

Traditional Name

(1R,2S,3S,4R,5S,7S,8R,9R,10S,11E,13S,14S,17R)-2,7,9-tris(acetyloxy)-5,13-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0^{1,17}.0^{3,8}]octadec-11-en-10-yl butanoate

CAS Registry Number

Not Available

SMILES

CCCC(=O)O[C@H]1\C=C(C)\[C@H](O)[C@@H]2OC(=O)[C@]3(C)O[C@]23[C@@H](OC(C)=O)[C@H]2[C@@H](C)[C@@H](O)C[C@H](OC(C)=O)[C@]2(C)[C@H]1OC(C)=O

InChI Identifier

InChI=1S/C30H42O13/c1-9-10-21(35)41-19-11-13(2)23(36)26-30(29(8,43-30)27(37)42-26)25(40-17(6)33)22-14(3)18(34)12-20(38-15(4)31)28(22,7)24(19)39-16(5)32/h11,14,18-20,22-26,34,36H,9-10,12H2,1-8H3/b13-11+/t14-,18-,19-,20-,22+,23-,24-,25-,26-,28-,29-,30+/m0/s1

InChI Key

VACOXDJECSFREG-DBJWEONTSA-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

Diterpene lactone
Diterpenoid
Briarane diterpenoid
Pentacarboxylic acid or derivatives
Fatty acid ester
Para-dioxane
Gamma butyrolactone
Fatty acyl
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Ether
Oxirane
Dialkyl ether
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Alcohol
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	0.87	ChemAxon
pKa (Strongest Acidic)	13.47	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	184.49 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	143.8 m³·mol⁻¹	ChemAxon
Polarizability	61.22 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

Not Available

Chemspider ID

27024787

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46211756

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,3s,4r,5s,7s,8r,9r,10s,11e,13s,14s,17r)-2,7,9-tris(acetyloxy)-5,13-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-11-en-10-yl butanoate (NP0222237)

MOL for NP0222237 ((1r,2s,3s,4r,5s,7s,8r,9r,10s,11e,13s,14s,17r)-2,7,9-tris(acetyloxy)-5,13-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-11-en-10-yl butanoate)

3D MOL for NP0222237 ((1r,2s,3s,4r,5s,7s,8r,9r,10s,11e,13s,14s,17r)-2,7,9-tris(acetyloxy)-5,13-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-11-en-10-yl butanoate)

3D SDF for NP0222237 ((1r,2s,3s,4r,5s,7s,8r,9r,10s,11e,13s,14s,17r)-2,7,9-tris(acetyloxy)-5,13-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-11-en-10-yl butanoate)

3D-SDF for NP0222237 ((1r,2s,3s,4r,5s,7s,8r,9r,10s,11e,13s,14s,17r)-2,7,9-tris(acetyloxy)-5,13-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-11-en-10-yl butanoate)

PDB for NP0222237 ((1r,2s,3s,4r,5s,7s,8r,9r,10s,11e,13s,14s,17r)-2,7,9-tris(acetyloxy)-5,13-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-11-en-10-yl butanoate)

3D PDB for NP0222237 ((1r,2s,3s,4r,5s,7s,8r,9r,10s,11e,13s,14s,17r)-2,7,9-tris(acetyloxy)-5,13-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-11-en-10-yl butanoate)

SMILES for NP0222237 ((1r,2s,3s,4r,5s,7s,8r,9r,10s,11e,13s,14s,17r)-2,7,9-tris(acetyloxy)-5,13-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-11-en-10-yl butanoate)

INCHI for NP0222237 ((1r,2s,3s,4r,5s,7s,8r,9r,10s,11e,13s,14s,17r)-2,7,9-tris(acetyloxy)-5,13-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-11-en-10-yl butanoate)

Structure for NP0222237 ((1r,2s,3s,4r,5s,7s,8r,9r,10s,11e,13s,14s,17r)-2,7,9-tris(acetyloxy)-5,13-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-11-en-10-yl butanoate)

3D Structure for NP0222237 ((1r,2s,3s,4r,5s,7s,8r,9r,10s,11e,13s,14s,17r)-2,7,9-tris(acetyloxy)-5,13-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]octadec-11-en-10-yl butanoate)