NP-MRD: Showing NP-Card for (1s,5s,8r,9s,11s,12s,14r)-3-hydroxy-1,5,9-trimethyl-14-(prop-1-en-2-yl)tetracyclo[9.2.1.0⁴,¹².0⁸,¹²]tetradec-3-ene-2,13-dione (NP0289326)

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Record Information

Version

2.0

Created at

2022-09-09 19:27:23 UTC

Updated at

2022-09-09 19:27:23 UTC

NP-MRD ID

NP0289326

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,5s,8r,9s,11s,12s,14r)-3-hydroxy-1,5,9-trimethyl-14-(prop-1-en-2-yl)tetracyclo[9.2.1.0⁴,¹².0⁸,¹²]tetradec-3-ene-2,13-dione

Description

Elisapterosin B belongs to the class of organic compounds known as monoterpenoids. Monoterpenoids are compounds containing a chain of two isoprene units. (1s,5s,8r,9s,11s,12s,14r)-3-hydroxy-1,5,9-trimethyl-14-(prop-1-en-2-yl)tetracyclo[9.2.1.0⁴,¹².0⁸,¹²]tetradec-3-ene-2,13-dione is found in Antillogorgia elisabethae. (1s,5s,8r,9s,11s,12s,14r)-3-hydroxy-1,5,9-trimethyl-14-(prop-1-en-2-yl)tetracyclo[9.2.1.0⁴,¹².0⁸,¹²]tetradec-3-ene-2,13-dione was first documented in 2003 (PMID: 14570464). Based on a literature review a significant number of articles have been published on Elisapterosin B (PMID: 22577963) (PMID: 25089586) (PMID: 16774284) (PMID: 21399707) (PMID: 16478205) (PMID: 16108082).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 49 52  0  0  0  0  0  0  0  0999 V2000
    3.0745   -0.3118   -2.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0731   -0.4793   -0.7219 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3165   -1.0142   -0.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9293   -0.1464    0.1014 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7273    0.3439   -0.6778 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7590    1.7962   -0.9905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6479    2.3150   -0.6550 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5557    3.8070   -0.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9591    1.5484    0.5864 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4153    1.4644    0.9166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2443    0.8097   -0.1425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7312   -0.4995   -0.6156 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7024   -1.5860   -0.1395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3587   -0.7780   -0.2120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8603   -2.0178   -0.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6633   -3.0783   -0.7647 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5573   -2.2124    0.0091 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1317   -3.2118   -0.4692 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3015   -1.2631    0.8923 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1441   -1.9233    1.9030 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1974   -0.4414    1.5297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0197   -0.4200    2.7028 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4029    0.2100    0.3455 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2323    0.0770   -2.5594 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9492   -0.5696   -2.6488 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2233   -0.4866   -0.5238 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3784   -0.8381    0.9866 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4307   -2.1211   -0.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1481    0.6605    0.8409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5344   -0.2823   -1.5663 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4796    2.3780   -0.3666 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9238    2.0244   -2.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3681    2.0663   -1.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5511    4.0205    0.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3917    4.2286   -0.8410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4130    4.2794   -0.9363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4478    2.0232    1.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7960    2.5073    1.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5087    0.9813    1.9094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3241    1.5508   -0.9909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2834    0.7301    0.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7927   -0.5215   -1.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6868   -1.1287    0.1371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3304   -2.0745    0.7840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9035   -2.3237   -0.9239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8912   -3.7922   -0.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8576   -2.6194    1.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4806   -2.5513    2.5485 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6160   -1.1297    2.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  3
  4 19  1  0
 19 20  1  1
 19 21  1  0
 21 22  2  0
 23 21  1  1
 23  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  9  7  1  0
 23  5  1  0
 14 23  1  0
 17 19  1  0
  8 34  1  0
  8 35  1  0
  8 36  1  0
  7 33  1  6
  6 31  1  0
  6 32  1  0
  5 30  1  6
  4 29  1  1
  3 26  1  0
  3 27  1  0
  3 28  1  0
  1 24  1  0
  1 25  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
  9 37  1  1
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  6
 13 43  1  0
 13 44  1  0
 13 45  1  0
 16 46  1  0
M  END


  Mrv1652309092221282D          

 23 26  0  0  1  0            999 V2000
   -0.7743   -0.8598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1061   -0.3760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1909    0.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7002   -0.6089    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1862    0.0578    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1344    0.7789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9195    1.0325    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1757    1.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4033    0.3643    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2236    0.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5580   -0.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0719   -1.1441    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4063   -1.8984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2516   -1.0566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7656   -1.7232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0999   -2.4774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9453   -1.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4592   -2.3023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6109   -0.8814    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2097   -0.9663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0970   -0.2148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7626    0.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9173   -0.3023    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  4 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 23 21  1  6  0  0  0
 14 23  1  0  0  0  0
  5 23  1  0  0  0  0
  9 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0289326

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C[C@H]2[C@H](C(C)=C)[C@@]3(C)C(=O)[C@@]22[C@@H]1CC[C@H](C)C2=C(O)C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O3/c1-9(2)14-13-8-11(4)12-7-6-10(3)15-16(21)17(22)19(14,5)18(23)20(12,13)15/h10-14,21H,1,6-8H2,2-5H3/t10-,11-,12+,13-,14-,19+,20-/m0/s1

> <INCHI_KEY>
ZIHCUEBUFDWZOZ-AEZFRWBSSA-N

> <FORMULA>
C20H26O3

> <MOLECULAR_WEIGHT>
314.425

> <EXACT_MASS>
314.188194697

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
34.849176226627996

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,5S,8R,9S,11S,12S,14R)-3-hydroxy-1,5,9-trimethyl-14-(prop-1-en-2-yl)tetracyclo[9.2.1.0^{4,12}.0^{8,12}]tetradec-3-ene-2,13-dione

> <JCHEM_LOGP>
4.058436198

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.874979619032421

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8463439146353062

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
89.89979999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5S,8R,9S,11S,12S,14R)-3-hydroxy-1,5,9-trimethyl-14-(prop-1-en-2-yl)tetracyclo[9.2.1.0^{4,12}.0^{8,12}]tetradec-3-ene-2,13-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.445  -1.605   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.198  -0.702   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.356   0.830   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.307  -1.137   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.214   0.108   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.118   1.454   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.583   1.927   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.061   3.391   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.486   0.680   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.017   0.517   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.642  -0.891   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.734  -2.136   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.358  -3.544   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.203  -1.972   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.296  -3.217   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.920  -4.625   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.764  -3.053   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.857  -4.298   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.140  -1.645   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.391  -1.804   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.048  -0.401   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.424   1.007   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.579  -0.564   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   19                                                  
CONECT    5    4    6   23                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   23                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   23                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    4   20   21                                             
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   14    5    9                                             
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₆O₃

Average Mass

314.4250 Da

Monoisotopic Mass

314.18819 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H]1C[C@H]2[C@H](C(C)=C)[C@@]3(C)C(=O)[C@@]22[C@@H]1CC[C@H](C)C2=C(O)C3=O

InChI Identifier

InChI=1S/C20H26O3/c1-9(2)14-13-8-11(4)12-7-6-10(3)15-16(21)17(22)19(14,5)18(23)20(12,13)15/h10-14,21H,1,6-8H2,2-5H3/t10-,11-,12+,13-,14-,19+,20-/m0/s1

InChI Key

ZIHCUEBUFDWZOZ-AEZFRWBSSA-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
Antillogorgia elisabethae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monoterpenoids. Monoterpenoids are compounds containing a chain of two isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Monoterpenoids

Alternative Parents

Substituents

Monoterpenoid
Cyclohexenone
Ketone
Enol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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

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

355398

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

401069

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Davies HM, Lian Y: The combined C-H functionalization/Cope rearrangement: discovery and applications in organic synthesis. Acc Chem Res. 2012 Jun 19;45(6):923-35. doi: 10.1021/ar300013t. Epub 2012 May 11. [PubMed:22577963 ]
Preindl J, Leitner C, Baldauf S, Mulzer J: A short access to the skeleton of Elisabethin A and formal syntheses of Elisapterosin B and Colombiasin A. Org Lett. 2014 Aug 15;16(16):4276-9. doi: 10.1021/ol501998y. Epub 2014 Aug 4. [PubMed:25089586 ]
Rychnovsky SD: Predicting NMR spectra by computational methods: structure revision of hexacyclinol. Org Lett. 2006 Jun 22;8(13):2895-8. doi: 10.1021/ol0611346. [PubMed:16774284 ]
Waizumi N, Stankovic AR, Rawal VH: A general strategy to elisabethane diterpenes: stereocontrolled synthesis of elisapterosin B via oxidative cyclization of an elisabethin precursor. J Am Chem Soc. 2003 Oct 29;125(43):13022-3. doi: 10.1021/ja035898h. [PubMed:14570464 ]
Ying W, Barnes CL, Harmata M: Toward the total synthesis of elisapterosin B: A Hg(OTf)(2)-promoted diastereoselective intramolecular Friedel-Crafts alkylation reaction. Tetrahedron Lett. 2011 Jan 12;52(2):177-180. doi: 10.1016/j.tetlet.2010.10.109. [PubMed:21399707 ]
Davies HM, Dai X, Long MS: Combined C-H activation/cope rearrangement as a strategic reaction in organic synthesis: total synthesis of (-)-colombiasin a and (-)-elisapterosin B. J Am Chem Soc. 2006 Feb 22;128(7):2485-90. doi: 10.1021/ja056877l. [PubMed:16478205 ]
Boezio AA, Jarvo ER, Lawrence BM, Jacobsen EN: Efficient total syntheses of (-)-colombiasin A and (-)-elisapterosin B: application of the Cr-catalyzed asymmetric quinone Diels-Alder reaction. Angew Chem Int Ed Engl. 2005 Sep 19;44(37):6046-50. doi: 10.1002/anie.200502178. [PubMed:16108082 ]
Harrowven DC, Pascoe DD, Demurtas D, Bourne HO: Total synthesis of (-)-colombiasin A and (-)-elisapterosin B. Angew Chem Int Ed Engl. 2005 Feb 11;44(8):1221-2. doi: 10.1002/anie.200462268. [PubMed:15696589 ]
Kim AI, Rychnovsky SD: Unified strategy for the synthesis of (-)-elisapterosin B and (-)-colombiasin A. Angew Chem Int Ed Engl. 2003 Mar 17;42(11):1267-70. doi: 10.1002/anie.200390325. [PubMed:12645060 ]
LOTUS database [Link]

Showing NP-Card for (1s,5s,8r,9s,11s,12s,14r)-3-hydroxy-1,5,9-trimethyl-14-(prop-1-en-2-yl)tetracyclo[9.2.1.0⁴,¹².0⁸,¹²]tetradec-3-ene-2,13-dione (NP0289326)

MOL for NP0289326 ((1s,5s,8r,9s,11s,12s,14r)-3-hydroxy-1,5,9-trimethyl-14-(prop-1-en-2-yl)tetracyclo[9.2.1.0⁴,¹².0⁸,¹²]tetradec-3-ene-2,13-dione)

3D MOL for NP0289326 ((1s,5s,8r,9s,11s,12s,14r)-3-hydroxy-1,5,9-trimethyl-14-(prop-1-en-2-yl)tetracyclo[9.2.1.0⁴,¹².0⁸,¹²]tetradec-3-ene-2,13-dione)

3D SDF for NP0289326 ((1s,5s,8r,9s,11s,12s,14r)-3-hydroxy-1,5,9-trimethyl-14-(prop-1-en-2-yl)tetracyclo[9.2.1.0⁴,¹².0⁸,¹²]tetradec-3-ene-2,13-dione)

3D-SDF for NP0289326 ((1s,5s,8r,9s,11s,12s,14r)-3-hydroxy-1,5,9-trimethyl-14-(prop-1-en-2-yl)tetracyclo[9.2.1.0⁴,¹².0⁸,¹²]tetradec-3-ene-2,13-dione)

PDB for NP0289326 ((1s,5s,8r,9s,11s,12s,14r)-3-hydroxy-1,5,9-trimethyl-14-(prop-1-en-2-yl)tetracyclo[9.2.1.0⁴,¹².0⁸,¹²]tetradec-3-ene-2,13-dione)

3D PDB for NP0289326 ((1s,5s,8r,9s,11s,12s,14r)-3-hydroxy-1,5,9-trimethyl-14-(prop-1-en-2-yl)tetracyclo[9.2.1.0⁴,¹².0⁸,¹²]tetradec-3-ene-2,13-dione)

SMILES for NP0289326 ((1s,5s,8r,9s,11s,12s,14r)-3-hydroxy-1,5,9-trimethyl-14-(prop-1-en-2-yl)tetracyclo[9.2.1.0⁴,¹².0⁸,¹²]tetradec-3-ene-2,13-dione)

INCHI for NP0289326 ((1s,5s,8r,9s,11s,12s,14r)-3-hydroxy-1,5,9-trimethyl-14-(prop-1-en-2-yl)tetracyclo[9.2.1.0⁴,¹².0⁸,¹²]tetradec-3-ene-2,13-dione)

Structure for NP0289326 ((1s,5s,8r,9s,11s,12s,14r)-3-hydroxy-1,5,9-trimethyl-14-(prop-1-en-2-yl)tetracyclo[9.2.1.0⁴,¹².0⁸,¹²]tetradec-3-ene-2,13-dione)

3D Structure for NP0289326 ((1s,5s,8r,9s,11s,12s,14r)-3-hydroxy-1,5,9-trimethyl-14-(prop-1-en-2-yl)tetracyclo[9.2.1.0⁴,¹².0⁸,¹²]tetradec-3-ene-2,13-dione)