NP-MRD: Showing NP-Card for (1s,2s,3s,4r,7s,8z,11s,12r,13r,14s,16s,17r)-11,12,14-tris(acetyloxy)-3,4,16-trihydroxy-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-8-en-2-yl acetate (NP0164689)

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Record Information

Version

2.0

Created at

2022-09-02 23:37:17 UTC

Updated at

2022-09-02 23:37:18 UTC

NP-MRD ID

NP0164689

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,3s,4r,7s,8z,11s,12r,13r,14s,16s,17r)-11,12,14-tris(acetyloxy)-3,4,16-trihydroxy-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-8-en-2-yl acetate

Description

(1R,3aS,4Z,7S,8R,8aR,9S,11S,12R,12aS,13S,13aS)-1,5,8a,12-Tetramethyl-1,11,13a-trihydroxy-7,8,9,13-tetraacetoxy-3a,6,7,8,8a,9,10,11,12,12a,13,13a-dodecahydrobenzo[4,5]cyclodeca[1,2-b]furan-2(1H)-one belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (1s,2s,3s,4r,7s,8z,11s,12r,13r,14s,16s,17r)-11,12,14-tris(acetyloxy)-3,4,16-trihydroxy-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-8-en-2-yl acetate is found in Briareum excavatum. Based on a literature review very few articles have been published on (1R,3aS,4Z,7S,8R,8aR,9S,11S,12R,12aS,13S,13aS)-1,5,8a,12-Tetramethyl-1,11,13a-trihydroxy-7,8,9,13-tetraacetoxy-3a,6,7,8,8a,9,10,11,12,12a,13,13a-dodecahydrobenzo[4,5]cyclodeca[1,2-b]furan-2(1H)-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032201372D          

 41 43  0  0  1  0            999 V2000
    2.7067    6.1725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3537    5.2026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6225    4.8206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3684    4.9060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3337    4.0818    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0302    3.6396    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
    4.7961    4.8459    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
    4.1935    1.0339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7946    0.7353    0.0000 O   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  1  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  1  0  0  0  0  0  0  0  0  0
    3.2295    1.6090    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9259    1.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4983    1.2269    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4635    0.4027    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
    1.8365    2.4934    0.0000 C   0  0  2  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
    2.5677    2.8755    0.0000 C   0  0  1  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
    2.6025    3.6997    0.0000 C   0  0  1  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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  6  0  0  0
 14 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
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 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 30 35  1  0  0  0  0
 24 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
  5 37  1  0  0  0  0
 37 38  1  1  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
M  END

     RDKit          3D

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    1.0377    3.9510    2.3033 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2756    3.3816    0.1420 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3846    2.2366    0.1998 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.0481    2.7908    0.0798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2218    4.0680    0.8215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0559    1.9306    0.1502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0110    0.6462   -0.5338 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3706    0.5786   -1.0804 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0297   -0.4828   -0.4397 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0645   -0.7050    3.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8839   -1.2908    0.2419 C   0  0  2  0  0  0  0  0  0  0  0  0
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    3.6116   -1.9705   -1.4001 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8525   -1.6459   -2.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0382   -3.0894   -1.5205 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5115   -0.6114   -1.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5175    1.7239   -2.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9092    1.6597    0.2374 O   0  0  0  0  0  0  0  0  0  0  0  0
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 37 78  1  1
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 40 81  1  0
M  END


  Mrv1652309032201372D          

 41 43  0  0  1  0            999 V2000
    2.7067    6.1725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3537    5.2026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0302    3.6396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    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
    4.1935    1.0339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7946    0.7353    0.0000 O   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  1  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  1  0  0  0  0  0  0  0  0  0
    3.2295    1.6090    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9259    1.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4983    1.2269    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4635    0.4027    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
    1.8365    2.4934    0.0000 C   0  0  2  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
    2.5677    2.8755    0.0000 C   0  0  1  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
    2.6025    3.6997    0.0000 C   0  0  1  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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  6  0  0  0
 14 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 30 35  1  0  0  0  0
 24 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
  5 37  1  0  0  0  0
 37 38  1  1  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0164689

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C28H40O13/c1-12-9-19(37-14(3)29)23(39-16(5)31)26(7)20(38-15(4)30)11-18(33)13(2)22(26)24(40-17(6)32)28(36)21(10-12)41-25(34)27(28,8)35/h10,13,18-24,33,35-36H,9,11H2,1-8H3/b12-10-/t13-,18-,19-,20-,21-,22+,23-,24-,26-,27-,28-/m0/s1

> <INCHI_KEY>
ZHECUSALRKIRAJ-JSUURTJWSA-N

> <FORMULA>
C28H40O13

> <MOLECULAR_WEIGHT>
584.615

> <EXACT_MASS>
584.246891348

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
59.037942718628734

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,3S,4R,7S,8Z,11S,12R,13R,14S,16S,17R)-11,12,14-tris(acetyloxy)-3,4,16-trihydroxy-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0^{3,7}]heptadec-8-en-2-yl acetate

> <ALOGPS_LOGP>
0.90

> <JCHEM_LOGP>
-0.521762044000001

> <ALOGPS_LOGS>
-3.07

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.499606746914782

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.137253425096057

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8607037219348657

> <JCHEM_POLAR_SURFACE_AREA>
192.18999999999997

> <JCHEM_REFRACTIVITY>
136.8711

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.92e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,3S,4R,7S,8Z,11S,12R,13R,14S,16S,17R)-11,12,14-tris(acetyloxy)-3,4,16-trihydroxy-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0^{3,7}]heptadec-8-en-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       5.052  11.522   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.394   9.712   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.029   8.998   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.288   9.158   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.223   7.619   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.523   6.794   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.888   7.507   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.953   9.046   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.188   6.682   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.123   5.143   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      11.223   4.065   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.538   2.686   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      11.251   1.321   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.817   2.821   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.828   1.930   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.950   1.373   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.758   4.430   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.475   3.578   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.458   5.255   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.921   3.812   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.902   2.625   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.421   2.882   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.365   1.182   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.093   4.542   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.028   3.003   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.328   2.178   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.663   2.290   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.599   0.752   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       3.428   4.654   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.128   5.480   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       0.763   4.767   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.698   3.228   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -0.537   5.592   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       4.793   5.368   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.493   6.193   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.858   6.906   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       3.558   7.732   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       3.623   9.270   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       2.323  10.096   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       4.988   9.983   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   37                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14   10   18   19                                             
CONECT   18   17                                                            
CONECT   19   17   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   19   25   35                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   30   24   36   37                                             
CONECT   36   35                                                            
CONECT   37   35    5   38                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₀O₁₃

Average Mass

584.6150 Da

Monoisotopic Mass

584.24689 Da

IUPAC Name

(1S,2S,3S,4R,7S,8Z,11S,12R,13R,14S,16S,17R)-11,12,14-tris(acetyloxy)-3,4,16-trihydroxy-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0^{3,7}]heptadec-8-en-2-yl acetate

Traditional Name

(1S,2S,3S,4R,7S,8Z,11S,12R,13R,14S,16S,17R)-11,12,14-tris(acetyloxy)-3,4,16-trihydroxy-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0^{3,7}]heptadec-8-en-2-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@@H](O)C[C@H](OC(C)=O)[C@@]2(C)[C@H]1[C@H](OC(C)=O)[C@@]1(O)[C@@H](OC(=O)[C@]1(C)O)\C=C(C)/C[C@H](OC(C)=O)[C@@H]2OC(C)=O

InChI Identifier

InChI=1S/C28H40O13/c1-12-9-19(37-14(3)29)23(39-16(5)31)26(7)20(38-15(4)30)11-18(33)13(2)22(26)24(40-17(6)32)28(36)21(10-12)41-25(34)27(28,8)35/h10,13,18-24,33,35-36H,9,11H2,1-8H3/b12-10-/t13-,18-,19-,20-,21-,22+,23-,24-,26-,27-,28-/m0/s1

InChI Key

ZHECUSALRKIRAJ-JSUURTJWSA-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

Briarane diterpenoid
Diterpenoid
Diterpene lactone
Pentacarboxylic acid or derivatives
Gamma butyrolactone
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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	0.9	ALOGPS
logP	-0.52	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	11.14	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	192.19 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	136.87 m³·mol⁻¹	ChemAxon
Polarizability	59.04 Å³	ChemAxon
Number of Rings	3	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101136794

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2s,3s,4r,7s,8z,11s,12r,13r,14s,16s,17r)-11,12,14-tris(acetyloxy)-3,4,16-trihydroxy-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-8-en-2-yl acetate (NP0164689)

MOL for NP0164689 ((1s,2s,3s,4r,7s,8z,11s,12r,13r,14s,16s,17r)-11,12,14-tris(acetyloxy)-3,4,16-trihydroxy-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-8-en-2-yl acetate)

3D MOL for NP0164689 ((1s,2s,3s,4r,7s,8z,11s,12r,13r,14s,16s,17r)-11,12,14-tris(acetyloxy)-3,4,16-trihydroxy-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-8-en-2-yl acetate)

3D SDF for NP0164689 ((1s,2s,3s,4r,7s,8z,11s,12r,13r,14s,16s,17r)-11,12,14-tris(acetyloxy)-3,4,16-trihydroxy-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-8-en-2-yl acetate)

3D-SDF for NP0164689 ((1s,2s,3s,4r,7s,8z,11s,12r,13r,14s,16s,17r)-11,12,14-tris(acetyloxy)-3,4,16-trihydroxy-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-8-en-2-yl acetate)

PDB for NP0164689 ((1s,2s,3s,4r,7s,8z,11s,12r,13r,14s,16s,17r)-11,12,14-tris(acetyloxy)-3,4,16-trihydroxy-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-8-en-2-yl acetate)

3D PDB for NP0164689 ((1s,2s,3s,4r,7s,8z,11s,12r,13r,14s,16s,17r)-11,12,14-tris(acetyloxy)-3,4,16-trihydroxy-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-8-en-2-yl acetate)

SMILES for NP0164689 ((1s,2s,3s,4r,7s,8z,11s,12r,13r,14s,16s,17r)-11,12,14-tris(acetyloxy)-3,4,16-trihydroxy-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-8-en-2-yl acetate)

INCHI for NP0164689 ((1s,2s,3s,4r,7s,8z,11s,12r,13r,14s,16s,17r)-11,12,14-tris(acetyloxy)-3,4,16-trihydroxy-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-8-en-2-yl acetate)

Structure for NP0164689 ((1s,2s,3s,4r,7s,8z,11s,12r,13r,14s,16s,17r)-11,12,14-tris(acetyloxy)-3,4,16-trihydroxy-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-8-en-2-yl acetate)

3D Structure for NP0164689 ((1s,2s,3s,4r,7s,8z,11s,12r,13r,14s,16s,17r)-11,12,14-tris(acetyloxy)-3,4,16-trihydroxy-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-8-en-2-yl acetate)