NP-MRD: Showing NP-Card for (1s,3s,5r,8e,13s,14r,15r)-14-hydroxy-5,9,13-trimethyl-18-methylidene-4,16-dioxatricyclo[13.3.0.0³,⁵]octadec-8-en-17-one (NP0247648)

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Record Information

Version

2.0

Created at

2022-09-07 09:34:25 UTC

Updated at

2022-09-07 09:34:25 UTC

NP-MRD ID

NP0247648

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3s,5r,8e,13s,14r,15r)-14-hydroxy-5,9,13-trimethyl-18-methylidene-4,16-dioxatricyclo[13.3.0.0³,⁵]octadec-8-en-17-one

Description

Eupalmerin belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. (1s,3s,5r,8e,13s,14r,15r)-14-hydroxy-5,9,13-trimethyl-18-methylidene-4,16-dioxatricyclo[13.3.0.0³,⁵]octadec-8-en-17-one is found in Eunicea mammosa. (1s,3s,5r,8e,13s,14r,15r)-14-hydroxy-5,9,13-trimethyl-18-methylidene-4,16-dioxatricyclo[13.3.0.0³,⁵]octadec-8-en-17-one was first documented in 2007 (PMID: 17237278). Based on a literature review a small amount of articles have been published on eupalmerin (PMID: 23695633) (PMID: 19281835) (PMID: 18037909) (PMID: 17868151).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 54 56  0  0  0  0  0  0  0  0999 V2000
   -3.3142    2.3210    1.5650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1758    1.1666    0.9408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2037    0.2045    0.6619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4515    0.2865    0.8561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5945   -0.9114    0.1085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1659   -0.7963    0.2560 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8705    0.6327    0.3898 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4871    1.3878   -0.8600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9943    2.7570   -0.6072 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0081    3.1277   -1.6594 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3006    3.1129   -0.3020 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5167    4.5523    0.2196 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3086    2.1883    0.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6032    0.9614   -0.5378 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9884    0.4380   -0.3502 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2755   -0.6673    0.3220 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6924   -1.1102    0.4490 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2606   -1.5272    0.9752 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4648   -2.3880    0.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1499   -2.7139    0.7241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9960   -2.9049   -0.2071 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4928   -3.7088   -1.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5212   -1.5875   -0.8015 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4851   -2.0156   -1.7491 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2739    2.6453    1.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4864    2.9986    1.7393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9883   -1.2721    1.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1189    0.8846    1.1686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4698    1.4619   -1.4334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8730    0.7976   -1.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8177    3.5338   -0.5506 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5392    4.8836    0.0505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1649    5.2558   -0.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2730    4.5713    1.2850 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3012    2.7196    0.3873 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0480    1.9046    1.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9317    0.1791   -0.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4917    1.1336   -1.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7809    1.0168   -0.8008 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3538   -0.6850   -0.3125 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0409   -0.8911    1.4888 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7839   -2.2267    0.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7699   -2.1536    1.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5442   -0.9005    1.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3650   -2.0216   -0.9712 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0100   -3.3738   -0.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0737   -1.9087    1.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2328   -3.6715    1.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7943   -3.4778    0.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0046   -3.0105   -2.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2642   -4.4528   -1.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3503   -4.1557   -1.9467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6373   -1.1718   -1.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4936   -1.4185   -2.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19 18  1  0
 18 16  1  0
 16 17  1  0
 16 15  2  0
 15 14  1  0
 14 13  1  0
 13 11  1  0
 11 12  1  1
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  6 23  1  0
 23 24  1  0
 23 21  1  0
  9 11  1  0
  2  7  1  0
 22 50  1  0
 22 51  1  0
 22 52  1  0
 21 49  1  1
 20 47  1  0
 20 48  1  0
 19 45  1  0
 19 46  1  0
 18 43  1  0
 18 44  1  0
 17 40  1  0
 17 41  1  0
 17 42  1  0
 15 39  1  0
 14 37  1  0
 14 38  1  0
 13 35  1  0
 13 36  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
  9 31  1  1
  8 29  1  0
  8 30  1  0
  7 28  1  1
  6 27  1  1
  1 25  1  0
  1 26  1  0
 23 53  1  6
 24 54  1  0
M  END


  Mrv1652309072211342D          

 24 26  0  0  1  0            999 V2000
    2.5813    0.6647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9697    1.3925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7868    1.5061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3590    0.9118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9313    2.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2035    2.7068    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6092    2.1346    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8254    1.8769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0075    1.9849    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2710    1.6133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3174    2.4370    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4834    2.2386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1082    3.1437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1850    3.9651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4094    4.5373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6966    5.3107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1244    5.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4803    5.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2982    5.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9883    5.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4139    4.3016    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1976    4.5593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4907    3.4802    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3086    3.3723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  2  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
  6 23  1  0  0  0  0
 23 24  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0247648

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CCC\C(C)=C\CC[C@@]2(C)O[C@H]2C[C@@H]2[C@@H](OC(=O)C2=C)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O4/c1-12-7-5-9-13(2)17(21)18-15(14(3)19(22)23-18)11-16-20(4,24-16)10-6-8-12/h8,13,15-18,21H,3,5-7,9-11H2,1-2,4H3/b12-8+/t13-,15-,16-,17+,18+,20+/m0/s1

> <INCHI_KEY>
SCMBIOHRSHWIJT-JJFWNEBZSA-N

> <FORMULA>
C20H30O4

> <MOLECULAR_WEIGHT>
334.456

> <EXACT_MASS>
334.214409446

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
37.44429417203891

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3S,5R,8E,13S,14R,15R)-14-hydroxy-5,9,13-trimethyl-18-methylidene-4,16-dioxatricyclo[13.3.0.0^{3,5}]octadec-8-en-17-one

> <JCHEM_LOGP>
3.8278215576666663

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.919286524346894

> <JCHEM_PKA_STRONGEST_BASIC>
-3.271504074250668

> <JCHEM_POLAR_SURFACE_AREA>
59.06

> <JCHEM_REFRACTIVITY>
93.098

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,5R,8E,13S,14R,15R)-14-hydroxy-5,9,13-trimethyl-18-methylidene-4,16-dioxatricyclo[13.3.0.0^{3,5}]octadec-8-en-17-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       4.818   1.241   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.543   2.599   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.069   2.811   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.137   1.702   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       7.339   4.328   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.980   5.053   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.870   3.985   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.407   3.504   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.881   3.705   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.506   3.011   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.593   4.549   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.902   4.179   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.202   5.868   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.345   7.402   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.764   8.470   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.300   9.913   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.232  11.023   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.763  10.394   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.290  10.193   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.578   9.349   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.373   8.030   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.836   8.511   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.516   6.496   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.043   6.295   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   23                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9   11                                                       
CONECT   11   10    9   12   13                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21    6   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₀O₄

Average Mass

334.4560 Da

Monoisotopic Mass

334.21441 Da

IUPAC Name

(1S,3S,5R,8E,13S,14R,15R)-14-hydroxy-5,9,13-trimethyl-18-methylidene-4,16-dioxatricyclo[13.3.0.0^{3,5}]octadec-8-en-17-one

Traditional Name

(1S,3S,5R,8E,13S,14R,15R)-14-hydroxy-5,9,13-trimethyl-18-methylidene-4,16-dioxatricyclo[13.3.0.0^{3,5}]octadec-8-en-17-one

CAS Registry Number

Not Available

SMILES

C[C@H]1CCC\C(C)=C\CC[C@@]2(C)O[C@H]2C[C@@H]2[C@@H](OC(=O)C2=C)[C@@H]1O

InChI Identifier

InChI=1S/C20H30O4/c1-12-7-5-9-13(2)17(21)18-15(14(3)19(22)23-18)11-16-20(4,24-16)10-6-8-12/h8,13,15-18,21H,3,5-7,9-11H2,1-2,4H3/b12-8+/t13-,15-,16-,17+,18+,20+/m0/s1

InChI Key

SCMBIOHRSHWIJT-JJFWNEBZSA-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
Eunicea mammosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
Gamma butyrolactone
Oxolane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Alcohol
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Carbonyl group
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	3.83	ChemAxon
pKa (Strongest Acidic)	13.92	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59.06 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	93.1 m³·mol⁻¹	ChemAxon
Polarizability	37.44 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

8195378

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23327293

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li J, Cisar JS, Zhou CY, Vera B, Williams H, Rodriguez AD, Cravatt BF, Romo D: Simultaneous structure-activity studies and arming of natural products by C-H amination reveal cellular targets of eupalmerin acetate. Nat Chem. 2013 Jun;5(6):510-7. doi: 10.1038/nchem.1653. Epub 2013 May 19. [PubMed:23695633 ]
Ferchmin PA, Pagan OR, Ulrich H, Szeto AC, Hann RM, Eterovic VA: Actions of octocoral and tobacco cembranoids on nicotinic receptors. Toxicon. 2009 Dec 15;54(8):1174-82. doi: 10.1016/j.toxicon.2009.02.033. Epub 2009 Mar 10. [PubMed:19281835 ]
Li P, Reichert DE, Rodriguez AD, Manion BD, Evers AS, Eterovic VA, Steinbach JH, Akk G: Mechanisms of potentiation of the mammalian GABAA receptor by the marine cembranoid eupalmerin acetate. Br J Pharmacol. 2008 Feb;153(3):598-608. doi: 10.1038/sj.bjp.0707597. Epub 2007 Nov 26. [PubMed:18037909 ]
Ulrich H, Akk G, Nery AA, Trujillo CA, Rodriguez AD, Eterovic VA: Mode of cembranoid action on embryonic muscle acetylcholine receptor. J Neurosci Res. 2008 Jan;86(1):93-107. doi: 10.1002/jnr.21468. [PubMed:17868151 ]
Iwamaru A, Iwado E, Kondo S, Newman RA, Vera B, Rodriguez AD, Kondo Y: Eupalmerin acetate, a novel anticancer agent from Caribbean gorgonian octocorals, induces apoptosis in malignant glioma cells via the c-Jun NH2-terminal kinase pathway. Mol Cancer Ther. 2007 Jan;6(1):184-92. doi: 10.1158/1535-7163.MCT-06-0422. [PubMed:17237278 ]
LOTUS database [Link]

Showing NP-Card for (1s,3s,5r,8e,13s,14r,15r)-14-hydroxy-5,9,13-trimethyl-18-methylidene-4,16-dioxatricyclo[13.3.0.0³,⁵]octadec-8-en-17-one (NP0247648)

MOL for NP0247648 ((1s,3s,5r,8e,13s,14r,15r)-14-hydroxy-5,9,13-trimethyl-18-methylidene-4,16-dioxatricyclo[13.3.0.0³,⁵]octadec-8-en-17-one)

3D MOL for NP0247648 ((1s,3s,5r,8e,13s,14r,15r)-14-hydroxy-5,9,13-trimethyl-18-methylidene-4,16-dioxatricyclo[13.3.0.0³,⁵]octadec-8-en-17-one)

3D SDF for NP0247648 ((1s,3s,5r,8e,13s,14r,15r)-14-hydroxy-5,9,13-trimethyl-18-methylidene-4,16-dioxatricyclo[13.3.0.0³,⁵]octadec-8-en-17-one)

3D-SDF for NP0247648 ((1s,3s,5r,8e,13s,14r,15r)-14-hydroxy-5,9,13-trimethyl-18-methylidene-4,16-dioxatricyclo[13.3.0.0³,⁵]octadec-8-en-17-one)

PDB for NP0247648 ((1s,3s,5r,8e,13s,14r,15r)-14-hydroxy-5,9,13-trimethyl-18-methylidene-4,16-dioxatricyclo[13.3.0.0³,⁵]octadec-8-en-17-one)

3D PDB for NP0247648 ((1s,3s,5r,8e,13s,14r,15r)-14-hydroxy-5,9,13-trimethyl-18-methylidene-4,16-dioxatricyclo[13.3.0.0³,⁵]octadec-8-en-17-one)

SMILES for NP0247648 ((1s,3s,5r,8e,13s,14r,15r)-14-hydroxy-5,9,13-trimethyl-18-methylidene-4,16-dioxatricyclo[13.3.0.0³,⁵]octadec-8-en-17-one)

INCHI for NP0247648 ((1s,3s,5r,8e,13s,14r,15r)-14-hydroxy-5,9,13-trimethyl-18-methylidene-4,16-dioxatricyclo[13.3.0.0³,⁵]octadec-8-en-17-one)

Structure for NP0247648 ((1s,3s,5r,8e,13s,14r,15r)-14-hydroxy-5,9,13-trimethyl-18-methylidene-4,16-dioxatricyclo[13.3.0.0³,⁵]octadec-8-en-17-one)

3D Structure for NP0247648 ((1s,3s,5r,8e,13s,14r,15r)-14-hydroxy-5,9,13-trimethyl-18-methylidene-4,16-dioxatricyclo[13.3.0.0³,⁵]octadec-8-en-17-one)