NP-MRD: Showing NP-Card for Amaurone E (NP0333213)

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Record Information

Version

2.0

Created at

2024-05-12 16:52:23 UTC

Updated at

2026-02-16 15:25:34 UTC

NP-MRD ID

NP0333213

Natural Product DOI

https://doi.org/10.57994/2544

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Amaurone E

Description

Amaurone E was first documented in 2021 (PMID: 33529015).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652311162200002D          

 37 40  0  0  1  0            999 V2000
    2.4728   -1.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2791   -0.5124    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8980    0.0579    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6922   -0.1655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2827    0.4106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0769    0.1872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6675    0.7632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4616    0.5398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0522    1.1159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8464    0.8925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4369    1.4686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2311    1.2452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8217    1.8213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6158    1.5979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4347    0.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2289    0.2223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0500    0.0930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4594   -0.4830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8442   -0.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0478   -0.9298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8486    1.9154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0791    1.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6660    0.8717    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2536    1.4507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0460    2.2492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2507    2.4686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6337    2.8282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8273    1.1243    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1163    1.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1795    1.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3586    0.4780    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4310   -0.2771    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2473   -1.0813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5688   -0.1215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4961    0.9712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2772    1.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3758    0.4014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  4  5  2  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  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  2  0  0  0  0
 15 16  1  0  0  0  0
 10 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  2  0  0  0  0
  9 21  1  0  0  0  0
  5 22  1  0  0  0  0
  3 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  6  0  0  0
 28 31  1  0  0  0  0
 31 32  1  0  0  0  0
  2 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 29 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 31 37  1  1  0  0  0
M  END


  Mrv1652311162200002D          

 37 40  0  0  1  0            999 V2000
    2.4728   -1.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2791   -0.5124    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8980    0.0579    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6922   -0.1655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2827    0.4106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0769    0.1872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6675    0.7632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4616    0.5398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0522    1.1159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8464    0.8925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4369    1.4686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2311    1.2452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8217    1.8213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6158    1.5979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4347    0.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2289    0.2223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0500    0.0930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4594   -0.4830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8442   -0.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0478   -0.9298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8486    1.9154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0791    1.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6660    0.8717    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2536    1.4507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0460    2.2492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2507    2.4686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6337    2.8282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8273    1.1243    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1163    1.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1795    1.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3586    0.4780    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4310   -0.2771    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2473   -1.0813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5688   -0.1215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4961    0.9712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2772    1.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3758    0.4014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  4  5  2  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  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  2  0  0  0  0
 15 16  1  0  0  0  0
 10 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  2  0  0  0  0
  9 21  1  0  0  0  0
  5 22  1  0  0  0  0
  3 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  6  0  0  0
 28 31  1  0  0  0  0
 31 32  1  0  0  0  0
  2 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 29 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 31 37  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0333213

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C)C(=O)C(C)=C(O1)C(\C)=C\C=C\C(\C)=C\[C@@H]1[C@H](C)[C@@]2(C)OC3(C)O[C@H]2[C@@](C)(O3)[C@H]1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H38O8/c1-15(12-11-13-16(2)23-17(3)22(31)18(4)25(32-10)34-23)14-21-19(5)27(7)26-28(8,24(21)33-20(6)30)37-29(9,35-26)36-27/h11-14,19,21,24,26H,1-10H3/b12-11+,15-14+,16-13+/t19-,21+,24-,26+,27+,28-,29?/m0/s1

> <INCHI_KEY>
AVMCXNUBCHWMLR-XBWUUZCNSA-N

> <FORMULA>
C29H38O8

> <MOLECULAR_WEIGHT>
514.615

> <EXACT_MASS>
514.256668184

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
56.75222929944772

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,4S,5R,6S,7R,8R)-5-[(1E,3E,5E)-6-(6-methoxy-3,5-dimethyl-4-oxo-4H-pyran-2-yl)-2-methylhepta-1,3,5-trien-1-yl]-1,3,6,7-tetramethyl-2,9,10-trioxatricyclo[5.2.1.0^{3,8}]decan-4-yl acetate

> <JCHEM_LOGP>
5.120560835999999

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.019657773000909

> <JCHEM_POLAR_SURFACE_AREA>
89.52000000000001

> <JCHEM_REFRACTIVITY>
150.9187

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4S,5R,6S,7R,8R)-5-[(1E,3E,5E)-6-(6-methoxy-3,5-dimethyl-4-oxopyran-2-yl)-2-methylhepta-1,3,5-trien-1-yl]-1,3,6,7-tetramethyl-2,9,10-trioxatricyclo[5.2.1.0^{3,8}]decan-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-NOV-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-NOV-22         0                                  
HETATM    1  C   UNK     0       4.616  -2.454   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.254  -0.957   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.410   0.108   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.892  -0.309   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.994   0.766   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.477   0.349   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.579   1.425   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.062   1.008   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.164   2.083   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.647   1.666   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      15.749   2.741   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      17.231   2.324   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      18.334   3.400   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      19.816   2.983   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.611   0.832   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      19.094   0.415   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.027   0.174   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.924  -0.902   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.509  -0.243   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      16.889  -1.736   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      12.784   3.575   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.614   2.259   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.976   1.627   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.073   2.708   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.686   4.198   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.201   4.608   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.783   5.279   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.411   2.099   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.084   2.987   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.068   3.491   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.536   0.892   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.671  -0.517   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.328  -2.018   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.062  -0.227   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       0.926   1.813   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.517   2.350   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       0.701   0.749   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   32                                                  
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   22                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   21                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   19                                                  
CONECT   16   15                                                            
CONECT   17   10   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   15   20                                                  
CONECT   20   19                                                            
CONECT   21    9                                                            
CONECT   22    5                                                            
CONECT   23    3   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   23   29   30   31                                             
CONECT   29   28   35                                                       
CONECT   30   28                                                            
CONECT   31   28   32   37                                                  
CONECT   32   31    2   33   34                                             
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   29   36   37                                             
CONECT   36   35                                                            
CONECT   37   35   31                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₈O₈

Average Mass

514.6150 Da

Monoisotopic Mass

514.25667 Da

IUPAC Name

(3S,4S,5R,6S,7R,8R)-5-[(1E,3E,5E)-6-(6-methoxy-3,5-dimethyl-4-oxo-4H-pyran-2-yl)-2-methylhepta-1,3,5-trien-1-yl]-1,3,6,7-tetramethyl-2,9,10-trioxatricyclo[5.2.1.0^{3,8}]decan-4-yl acetate

Traditional Name

(3S,4S,5R,6S,7R,8R)-5-[(1E,3E,5E)-6-(6-methoxy-3,5-dimethyl-4-oxopyran-2-yl)-2-methylhepta-1,3,5-trien-1-yl]-1,3,6,7-tetramethyl-2,9,10-trioxatricyclo[5.2.1.0^{3,8}]decan-4-yl acetate

CAS Registry Number

Not Available

SMILES

COC1=C(C)C(=O)C(C)=C(O1)C(\C)=C\C=C\C(\C)=C\[C@@H]1[C@H](C)[C@@]2(C)OC3(C)O[C@H]2[C@@](C)(O3)[C@H]1OC(C)=O

InChI Identifier

InChI=1S/C29H38O8/c1-15(12-11-13-16(2)23-17(3)22(31)18(4)25(32-10)34-23)14-21-19(5)27(7)26-28(8,24(21)33-20(6)30)37-29(9,35-26)36-27/h11-14,19,21,24,26H,1-10H3/b12-11+,15-14+,16-13+/t19-,21+,24-,26+,27+,28-,29?/m0/s1

InChI Key

AVMCXNUBCHWMLR-XBWUUZCNSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	[email protected]	Not Available	Not Available	2024-05-12	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	[email protected]	Not Available	Not Available	2024-05-12	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	[email protected]	Not Available	Not Available	2024-05-12	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	[email protected]	Not Available	Not Available	2024-05-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	[email protected]	Not Available	Not Available	2024-05-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C2D6OS, experimental)	[email protected]	Not Available	Not Available	2024-05-12	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Amauroascus sp. CMB-F713		Not Available
Amauroascus sp. CMB-F713		Not Available

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
logP	5.12	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	89.52 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	150.92 m³·mol⁻¹	ChemAxon
Polarizability	56.75 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

Not Available

References

General References

DOI: 10.1021/acs.jnatprod.0c01343

Showing NP-Card for Amaurone E (NP0333213)

MOL for NP0333213 (Amaurone E)

3D MOL for NP0333213 (Amaurone E)

3D SDF for NP0333213 (Amaurone E)

3D-SDF for NP0333213 (Amaurone E)

PDB for NP0333213 (Amaurone E)

3D PDB for NP0333213 (Amaurone E)

SMILES for NP0333213 (Amaurone E)

INCHI for NP0333213 (Amaurone E)

Structure for NP0333213 (Amaurone E)

3D Structure for NP0333213 (Amaurone E)