NP-MRD: Showing NP-Card for [(1s,2r,3s,4r,7s,8z,10r,12r,13s,14s,16s,18r)-2,10,12,14-tetrakis(acetyloxy)-3-hydroxy-4,13,18-trimethyl-5-oxo-6,17-dioxatetracyclo[11.5.0.0³,⁷.0¹⁶,¹⁸]octadec-8-en-9-yl]methyl acetate (NP0143540)

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Record Information

Version

2.0

Created at

2022-09-01 22:19:56 UTC

Updated at

2022-09-01 22:19:56 UTC

NP-MRD ID

NP0143540

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1s,2r,3s,4r,7s,8z,10r,12r,13s,14s,16s,18r)-2,10,12,14-tetrakis(acetyloxy)-3-hydroxy-4,13,18-trimethyl-5-oxo-6,17-dioxatetracyclo[11.5.0.0³,⁷.0¹⁶,¹⁸]octadec-8-en-9-yl]methyl acetate

Description

[(1S,2R,3S,4R,7S,8Z,10R,12R,13S,14S,16S,18R)-2,10,12,14-tetrakis(acetyloxy)-3-hydroxy-4,13,18-trimethyl-5-oxo-6,17-dioxatetracyclo[11.5.0.0³,⁷.0¹⁶,¹⁸]Octadec-8-en-9-yl]methyl acetate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. [(1s,2r,3s,4r,7s,8z,10r,12r,13s,14s,16s,18r)-2,10,12,14-tetrakis(acetyloxy)-3-hydroxy-4,13,18-trimethyl-5-oxo-6,17-dioxatetracyclo[11.5.0.0³,⁷.0¹⁶,¹⁸]octadec-8-en-9-yl]methyl acetate is found in Briareum stechei. Based on a literature review very few articles have been published on [(1S,2R,3S,4R,7S,8Z,10R,12R,13S,14S,16S,18R)-2,10,12,14-tetrakis(acetyloxy)-3-hydroxy-4,13,18-trimethyl-5-oxo-6,17-dioxatetracyclo[11.5.0.0³,⁷.0¹⁶,¹⁸]Octadec-8-en-9-yl]methyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022200192D          

 44 47  0  0  1  0            999 V2000
    6.2932    6.4343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5620    6.0522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8656    6.4944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5273    5.2279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7961    4.8459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7614    4.0216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4578    3.5794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4231    2.7551    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0124    2.1778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6454    1.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0275    0.7077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7232    1.5111    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2519    0.9703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6919    2.3731    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0046    1.9167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9954    2.8153    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7077    2.0421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2334    1.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0469    1.5437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9457    0.6331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2642    2.4332    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5677    2.8755    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8713    3.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8365    2.4934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1401    2.9356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4089    2.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3741    1.7293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2876    2.9958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8018    1.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4983    1.2269    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1947    0.7847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2295    1.6090    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8759    1.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6025    3.6997    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9060    4.1419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6719    5.3483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3337    4.0818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0302    3.6396    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0649    4.4638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3684    4.9060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6372    4.5240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4032    5.7303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
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 21 32  1  1  0  0  0
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 34 39  1  0  0  0  0
 39 40  1  0  0  0  0
  6 40  1  0  0  0  0
 40 41  1  6  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  2  0  0  0  0
M  END

     RDKit          3D

 84 87  0  0  0  0  0  0  0  0999 V2000
    5.2043    2.7564    0.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6278    1.5864   -0.4667 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7433    0.4457    0.0462 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9732    1.6937   -1.6721 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4161    0.6123   -2.3857 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3705    0.0088   -1.4308 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4957   -1.2271   -1.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6145   -1.9412   -0.1700 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3961   -3.1475    0.1388 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5090   -4.1461    0.3368 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4758   -5.0495    1.1607 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7014    4.9951   -0.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5711    3.8426    0.8865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7362    0.8363   -1.2558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7751   -0.1862   -0.7530 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9816    0.0999    0.5437 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2015   -1.1130    0.2536 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0004   -2.2166    0.8333 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0547    1.7889    2.2871 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3152    2.8970    4.5179 C   0  0  0  0  0  0  0  0  0  0  0  0
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 43 84  1  0
M  END


  Mrv1652309022200192D          

 44 47  0  0  1  0            999 V2000
    6.2932    6.4343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5620    6.0522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8656    6.4944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5273    5.2279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7961    4.8459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7614    4.0216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4578    3.5794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4231    2.7551    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0124    2.1778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6454    1.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0275    0.7077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7232    1.5111    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2519    0.9703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6919    2.3731    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0046    1.9167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9954    2.8153    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7077    2.0421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2334    1.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0469    1.5437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9457    0.6331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2642    2.4332    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5677    2.8755    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8713    3.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8365    2.4934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1401    2.9356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4089    2.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3741    1.7293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2876    2.9958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8018    1.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4983    1.2269    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1947    0.7847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2295    1.6090    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8759    1.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6025    3.6997    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9060    4.1419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9407    4.9662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2443    5.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6719    5.3483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3337    4.0818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0302    3.6396    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0649    4.4638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3684    4.9060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6372    4.5240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4032    5.7303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  1  0  0  0
 31 32  1  0  0  0  0
 30 32  1  0  0  0  0
 21 32  1  1  0  0  0
 32 33  1  6  0  0  0
 22 34  1  0  0  0  0
 34 35  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 34 39  1  0  0  0  0
 39 40  1  0  0  0  0
  6 40  1  0  0  0  0
 40 41  1  6  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0143540

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C(=O)O[C@H]2\C=C(COC(C)=O)/[C@@H](C[C@@H](OC(C)=O)[C@@]3(C)[C@H](C[C@@H]4O[C@]4(C)[C@@H]3[C@@H](OC(C)=O)[C@]12O)OC(C)=O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H40O14/c1-13-27(36)43-24-9-19(12-38-14(2)31)20(39-15(3)32)10-21(40-16(4)33)28(7)22(41-17(5)34)11-23-29(8,44-23)25(28)26(30(13,24)37)42-18(6)35/h9,13,20-26,37H,10-12H2,1-8H3/b19-9-/t13-,20+,21+,22-,23-,24-,25+,26+,28-,29-,30-/m0/s1

> <INCHI_KEY>
ORUKJJWOQDYSJV-LBSKMGTMSA-N

> <FORMULA>
C30H40O14

> <MOLECULAR_WEIGHT>
624.636

> <EXACT_MASS>
624.241805968

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
62.23940248955493

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1S,2R,3S,4R,7S,8Z,10R,12R,13S,14S,16S,18R)-2,10,12,14-tetrakis(acetyloxy)-3-hydroxy-4,13,18-trimethyl-5-oxo-6,17-dioxatetracyclo[11.5.0.0^{3,7}.0^{16,18}]octadec-8-en-9-yl]methyl acetate

> <ALOGPS_LOGP>
1.81

> <JCHEM_LOGP>
-0.7207698690000012

> <ALOGPS_LOGS>
-3.70

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.355218614490969

> <JCHEM_PKA_STRONGEST_BASIC>
-3.95562737802165

> <JCHEM_POLAR_SURFACE_AREA>
190.55999999999997

> <JCHEM_REFRACTIVITY>
144.34990000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,2R,3S,4R,7S,8Z,10R,12R,13S,14S,16S,18R)-2,10,12,14-tetrakis(acetyloxy)-3-hydroxy-4,13,18-trimethyl-5-oxo-6,17-dioxatetracyclo[11.5.0.0^{3,7}.0^{16,18}]octadec-8-en-9-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      11.747  12.011   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.382  11.297   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       9.082  12.123   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      10.318   9.759   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.953   9.046   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.888   7.507   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.188   6.682   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.123   5.143   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      11.223   4.065   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.538   2.686   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      11.251   1.321   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.817   2.821   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.937   1.811   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.758   4.430   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.475   3.578   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       7.458   5.255   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.921   3.812   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.902   2.625   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.421   2.882   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.365   1.182   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.093   4.542   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.793   5.368   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.493   6.193   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.428   4.654   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.128   5.480   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.763   4.767   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.698   3.228   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.537   5.592   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.363   3.116   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.663   2.290   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.964   1.465   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.028   3.003   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.235   2.047   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.858   6.906   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       3.558   7.732   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       3.623   9.270   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.323  10.096   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       4.988   9.983   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       6.223   7.619   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       7.523   6.794   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       7.588   8.332   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       6.288   9.158   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       4.923   8.445   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       6.353  10.697   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   40                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    8   15   16                                             
CONECT   15   14                                                            
CONECT   16   14   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   16   22   32                                                  
CONECT   22   21   23   24   34                                             
CONECT   23   22                                                            
CONECT   24   22   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   24   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30   32                                                       
CONECT   32   31   30   21   33                                             
CONECT   33   32                                                            
CONECT   34   22   35   39                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   34   40                                                       
CONECT   40   39    6   41                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   94    0
END

View in JSmol

Synonyms

Value	Source
[(1S,2R,3S,4R,7S,8Z,10R,12R,13S,14S,16S,18R)-2,10,12,14-Tetrakis(acetyloxy)-3-hydroxy-4,13,18-trimethyl-5-oxo-6,17-dioxatetracyclo[11.5.0.0,.0,]octadec-8-en-9-yl]methyl acetic acid	Generator

Chemical Formula

C₃₀H₄₀O₁₄

Average Mass

624.6360 Da

Monoisotopic Mass

624.24181 Da

IUPAC Name

[(1S,2R,3S,4R,7S,8Z,10R,12R,13S,14S,16S,18R)-2,10,12,14-tetrakis(acetyloxy)-3-hydroxy-4,13,18-trimethyl-5-oxo-6,17-dioxatetracyclo[11.5.0.0^{3,7}.0^{16,18}]octadec-8-en-9-yl]methyl acetate

Traditional Name

[(1S,2R,3S,4R,7S,8Z,10R,12R,13S,14S,16S,18R)-2,10,12,14-tetrakis(acetyloxy)-3-hydroxy-4,13,18-trimethyl-5-oxo-6,17-dioxatetracyclo[11.5.0.0^{3,7}.0^{16,18}]octadec-8-en-9-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

C[C@H]1C(=O)O[C@H]2\C=C(COC(C)=O)/[C@@H](C[C@@H](OC(C)=O)[C@@]3(C)[C@H](C[C@@H]4O[C@]4(C)[C@@H]3[C@@H](OC(C)=O)[C@]12O)OC(C)=O)OC(C)=O

InChI Identifier

InChI=1S/C30H40O14/c1-13-27(36)43-24-9-19(12-38-14(2)31)20(39-15(3)32)10-21(40-16(4)33)28(7)22(41-17(5)34)11-23-29(8,44-23)25(28)26(30(13,24)37)42-18(6)35/h9,13,20-26,37H,10-12H2,1-8H3/b19-9-/t13-,20+,21+,22-,23-,24-,25+,26+,28-,29-,30-/m0/s1

InChI Key

ORUKJJWOQDYSJV-LBSKMGTMSA-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 stechei	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
Oxepane
Gamma butyrolactone
Tertiary alcohol
Tetrahydrofuran
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	1.81	ALOGPS
logP	-0.72	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	12.36	ChemAxon
pKa (Strongest Basic)	-4	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	11	ChemAxon
Refractivity	144.35 m³·mol⁻¹	ChemAxon
Polarizability	62.24 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10478592

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21776110

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

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References

General References

LOTUS database [Link]

Showing NP-Card for [(1s,2r,3s,4r,7s,8z,10r,12r,13s,14s,16s,18r)-2,10,12,14-tetrakis(acetyloxy)-3-hydroxy-4,13,18-trimethyl-5-oxo-6,17-dioxatetracyclo[11.5.0.0³,⁷.0¹⁶,¹⁸]octadec-8-en-9-yl]methyl acetate (NP0143540)

MOL for NP0143540 ([(1s,2r,3s,4r,7s,8z,10r,12r,13s,14s,16s,18r)-2,10,12,14-tetrakis(acetyloxy)-3-hydroxy-4,13,18-trimethyl-5-oxo-6,17-dioxatetracyclo[11.5.0.0³,⁷.0¹⁶,¹⁸]octadec-8-en-9-yl]methyl acetate)

3D MOL for NP0143540 ([(1s,2r,3s,4r,7s,8z,10r,12r,13s,14s,16s,18r)-2,10,12,14-tetrakis(acetyloxy)-3-hydroxy-4,13,18-trimethyl-5-oxo-6,17-dioxatetracyclo[11.5.0.0³,⁷.0¹⁶,¹⁸]octadec-8-en-9-yl]methyl acetate)

3D SDF for NP0143540 ([(1s,2r,3s,4r,7s,8z,10r,12r,13s,14s,16s,18r)-2,10,12,14-tetrakis(acetyloxy)-3-hydroxy-4,13,18-trimethyl-5-oxo-6,17-dioxatetracyclo[11.5.0.0³,⁷.0¹⁶,¹⁸]octadec-8-en-9-yl]methyl acetate)

3D-SDF for NP0143540 ([(1s,2r,3s,4r,7s,8z,10r,12r,13s,14s,16s,18r)-2,10,12,14-tetrakis(acetyloxy)-3-hydroxy-4,13,18-trimethyl-5-oxo-6,17-dioxatetracyclo[11.5.0.0³,⁷.0¹⁶,¹⁸]octadec-8-en-9-yl]methyl acetate)

PDB for NP0143540 ([(1s,2r,3s,4r,7s,8z,10r,12r,13s,14s,16s,18r)-2,10,12,14-tetrakis(acetyloxy)-3-hydroxy-4,13,18-trimethyl-5-oxo-6,17-dioxatetracyclo[11.5.0.0³,⁷.0¹⁶,¹⁸]octadec-8-en-9-yl]methyl acetate)

3D PDB for NP0143540 ([(1s,2r,3s,4r,7s,8z,10r,12r,13s,14s,16s,18r)-2,10,12,14-tetrakis(acetyloxy)-3-hydroxy-4,13,18-trimethyl-5-oxo-6,17-dioxatetracyclo[11.5.0.0³,⁷.0¹⁶,¹⁸]octadec-8-en-9-yl]methyl acetate)

SMILES for NP0143540 ([(1s,2r,3s,4r,7s,8z,10r,12r,13s,14s,16s,18r)-2,10,12,14-tetrakis(acetyloxy)-3-hydroxy-4,13,18-trimethyl-5-oxo-6,17-dioxatetracyclo[11.5.0.0³,⁷.0¹⁶,¹⁸]octadec-8-en-9-yl]methyl acetate)

INCHI for NP0143540 ([(1s,2r,3s,4r,7s,8z,10r,12r,13s,14s,16s,18r)-2,10,12,14-tetrakis(acetyloxy)-3-hydroxy-4,13,18-trimethyl-5-oxo-6,17-dioxatetracyclo[11.5.0.0³,⁷.0¹⁶,¹⁸]octadec-8-en-9-yl]methyl acetate)

Structure for NP0143540 ([(1s,2r,3s,4r,7s,8z,10r,12r,13s,14s,16s,18r)-2,10,12,14-tetrakis(acetyloxy)-3-hydroxy-4,13,18-trimethyl-5-oxo-6,17-dioxatetracyclo[11.5.0.0³,⁷.0¹⁶,¹⁸]octadec-8-en-9-yl]methyl acetate)

3D Structure for NP0143540 ([(1s,2r,3s,4r,7s,8z,10r,12r,13s,14s,16s,18r)-2,10,12,14-tetrakis(acetyloxy)-3-hydroxy-4,13,18-trimethyl-5-oxo-6,17-dioxatetracyclo[11.5.0.0³,⁷.0¹⁶,¹⁸]octadec-8-en-9-yl]methyl acetate)