NP-MRD: Showing NP-Card for (1s,2r,3ar,5s,11r,13as)-3a,11-bis(acetyloxy)-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate (NP0260744)

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Record Information

Version

2.0

Created at

2022-09-08 02:59:39 UTC

Updated at

2022-09-08 02:59:40 UTC

NP-MRD ID

NP0260744

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,3ar,5s,11r,13as)-3a,11-bis(acetyloxy)-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate

Description

(1s,2r,3ar,5s,11r,13as)-3a,11-bis(acetyloxy)-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate is found in Euphorbia helioscopia.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082204592D          

 39 41  0  0  1  0            999 V2000
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M  END

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M  END


  Mrv1652309082204592D          

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    1.3208    3.3363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1278    3.1648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3827    2.3802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9321   -0.2286    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6466    0.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0591    0.8984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6466    1.6128    0.0000 C   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  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 30 35  1  0  0  0  0
 26 36  1  0  0  0  0
 18 36  1  0  0  0  0
 36 37  1  6  0  0  0
 37 38  2  0  0  0  0
  5 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0260744

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@@]2(OC(C)=O)[C@@H](\C=C(C)\[C@@H](CC(=O)C(C)(C)\C=C\[C@H](C)C2=O)OC(C)=O)[C@H]1OC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C31H38O8/c1-18-13-14-30(6,7)26(34)16-25(37-21(4)32)19(2)15-24-27(38-29(36)23-11-9-8-10-12-23)20(3)17-31(24,28(18)35)39-22(5)33/h8-15,18,20,24-25,27H,16-17H2,1-7H3/b14-13+,19-15+/t18-,20+,24-,25+,27-,31+/m0/s1

> <INCHI_KEY>
VWSCEDLUJPCZIA-IYQIZHLBSA-N

> <FORMULA>
C31H38O8

> <MOLECULAR_WEIGHT>
538.637

> <EXACT_MASS>
538.256668184

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
56.216805878758535

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,3aR,5S,11R,13aS)-3a,11-bis(acetyloxy)-2,5,8,8,12-pentamethyl-4,9-dioxo-1H,2H,3H,3aH,4H,5H,8H,9H,10H,11H,13aH-cyclopenta[12]annulen-1-yl benzoate

> <JCHEM_LOGP>
5.445820719

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.28361778025202

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.080205541344274

> <JCHEM_PKA_STRONGEST_BASIC>
-6.459128064338817

> <JCHEM_POLAR_SURFACE_AREA>
113.04000000000002

> <JCHEM_REFRACTIVITY>
145.5877

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3aR,5S,11R,13aS)-3a,11-bis(acetyloxy)-2,5,8,8,12-pentamethyl-4,9-dioxo-1H,2H,3H,5H,10H,11H,13aH-cyclopenta[12]annulen-1-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      10.692   5.741   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.293   4.253   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       8.806   3.855   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      11.382   3.164   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.984   1.677   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.317   0.907   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.087  -0.427   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      14.575  -0.028   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      13.087  -1.967   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.604  -1.699   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.614  -3.414   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.754  -2.737   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.984  -4.070   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.444  -4.070   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.045  -5.558   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.110  -3.300   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.021  -4.389   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.340  -1.967   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.788  -3.404   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.267  -3.645   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.715  -5.083   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.298  -2.449   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.875  -2.443   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.970  -1.197   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.430  -1.197   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.875   0.049   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.399   1.514   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.893   1.834   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.863   0.690   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.417   3.299   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.911   3.619   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.435   5.083   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.465   6.228   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.972   5.908   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.448   4.443   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.340  -0.427   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.674   0.343   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.444   1.677   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       8.674   3.011   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   38                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   23   36                                             
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   18   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   36                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   30                                                       
CONECT   36   26   18   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37    5   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₃₈O₈

Average Mass

538.6370 Da

Monoisotopic Mass

538.25667 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@@]2(OC(C)=O)[C@@H](\C=C(C)\[C@@H](CC(=O)C(C)(C)\C=C\[C@H](C)C2=O)OC(C)=O)[C@H]1OC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C31H38O8/c1-18-13-14-30(6,7)26(34)16-25(37-21(4)32)19(2)15-24-27(38-29(36)23-11-9-8-10-12-23)20(3)17-31(24,28(18)35)39-22(5)33/h8-15,18,20,24-25,27H,16-17H2,1-7H3/b14-13+,19-15+/t18-,20+,24-,25+,27-,31+/m0/s1

InChI Key

VWSCEDLUJPCZIA-IYQIZHLBSA-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
Euphorbia helioscopia	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,3ar,5s,11r,13as)-3a,11-bis(acetyloxy)-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate (NP0260744)

MOL for NP0260744 ((1s,2r,3ar,5s,11r,13as)-3a,11-bis(acetyloxy)-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D MOL for NP0260744 ((1s,2r,3ar,5s,11r,13as)-3a,11-bis(acetyloxy)-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D SDF for NP0260744 ((1s,2r,3ar,5s,11r,13as)-3a,11-bis(acetyloxy)-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D-SDF for NP0260744 ((1s,2r,3ar,5s,11r,13as)-3a,11-bis(acetyloxy)-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

PDB for NP0260744 ((1s,2r,3ar,5s,11r,13as)-3a,11-bis(acetyloxy)-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D PDB for NP0260744 ((1s,2r,3ar,5s,11r,13as)-3a,11-bis(acetyloxy)-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

SMILES for NP0260744 ((1s,2r,3ar,5s,11r,13as)-3a,11-bis(acetyloxy)-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

INCHI for NP0260744 ((1s,2r,3ar,5s,11r,13as)-3a,11-bis(acetyloxy)-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

Structure for NP0260744 ((1s,2r,3ar,5s,11r,13as)-3a,11-bis(acetyloxy)-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D Structure for NP0260744 ((1s,2r,3ar,5s,11r,13as)-3a,11-bis(acetyloxy)-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)