NP-MRD: Showing NP-Card for 5-N-Acetyladreemin (NP0331158)

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Record Information

Version

2.0

Created at

2022-11-17 19:06:39 UTC

Updated at

2024-09-03 04:14:46 UTC

NP-MRD ID

NP0331158

Natural Product DOI

https://doi.org/10.57994/0033

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-N-Acetyladreemin

Description

(1S,12R,15R,23S)-16-acetyl-12-methyl-23-(2-methylbut-3-en-2-yl)-3,11,14,16-tetraazahexacyclo[12.10.0.0²,¹¹.0⁴,⁹.0¹⁵,²³.0¹⁷,²²]Tetracosa-2,4,6,8,17,19,21-heptaene-10,13-dione belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Based on a literature review very few articles have been published on (1S,12R,15R,23S)-16-acetyl-12-methyl-23-(2-methylbut-3-en-2-yl)-3,11,14,16-tetraazahexacyclo[12.10.0.0²,¹¹.0⁴,⁹.0¹⁵,²³.0¹⁷,²²]Tetracosa-2,4,6,8,17,19,21-heptaene-10,13-dione.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652311172220062D          

 37 42  0  0  1  0            999 V2000
    3.1117    1.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2881    0.9904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4646    0.9416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2393    1.8140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9282    2.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3369    0.1669    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3857   -0.6567    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1841   -0.8648    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5636   -1.5973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3878   -1.6348    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7673   -2.3673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8324   -0.9399    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4528   -0.2074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8974    0.4876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7215    0.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1011   -0.2825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9252   -0.3200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3698    0.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9903    1.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1661    1.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6565   -0.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0361   -1.7099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1190   -2.2922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6287   -0.1698    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9982    0.5678    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1051    0.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4345   -1.4802    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6176   -0.9576    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4095   -1.7559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6141   -1.9749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9968   -2.3353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0940   -0.3200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2699   -0.2825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1097    0.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3349    1.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1591    1.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5386    0.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  6  2  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  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
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 16 21  1  0  0  0  0
 12 21  1  0  0  0  0
 21 22  2  0  0  0  0
  9 23  2  0  0  0  0
  8 24  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
  6 26  1  0  0  0  0
  7 27  1  1  0  0  0
  7 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 28 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
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 32 37  1  0  0  0  0
  6 37  1  0  0  0  0
M  END


  Mrv1652311172220062D          

 37 42  0  0  1  0            999 V2000
    3.1117    1.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2881    0.9904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4646    0.9416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2393    1.8140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9282    2.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3369    0.1669    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3857   -0.6567    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1841   -0.8648    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5636   -1.5973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3878   -1.6348    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7673   -2.3673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8324   -0.9399    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4528   -0.2074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8974    0.4876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7215    0.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1011   -0.2825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9252   -0.3200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3698    0.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9903    1.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1661    1.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6565   -0.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0361   -1.7099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1190   -2.2922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6287   -0.1698    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9982    0.5678    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1051    0.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4345   -1.4802    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6176   -0.9576    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4095   -1.7559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6141   -1.9749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9968   -2.3353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0940   -0.3200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2699   -0.2825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1097    0.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3349    1.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1591    1.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5386    0.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  6  2  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  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
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 16 21  1  0  0  0  0
 12 21  1  0  0  0  0
 21 22  2  0  0  0  0
  9 23  2  0  0  0  0
  8 24  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
  6 26  1  0  0  0  0
  7 27  1  1  0  0  0
  7 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 28 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
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 32 37  1  0  0  0  0
  6 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331158

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12C[C@@]3(C4=CC=CC=C4N(C(C)=O)[C@@]3([H])N1C(=O)[C@@H](C)N1C(=O)C3=C(C=CC=C3)N=C21)C(C)(C)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C28H28N4O3/c1-6-27(4,5)28-15-22-23-29-20-13-9-7-11-18(20)25(35)30(23)16(2)24(34)32(22)26(28)31(17(3)33)21-14-10-8-12-19(21)28/h6-14,16,22,26H,1,15H2,2-5H3/t16-,22+,26+,28+/m1/s1

> <INCHI_KEY>
XTLQWSBGQKPGCF-FAZGTRELSA-N

> <FORMULA>
C28H28N4O3

> <MOLECULAR_WEIGHT>
468.557

> <EXACT_MASS>
468.216140778

$$$$

HEADER    PROTEIN                                 17-NOV-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-NOV-22         0                                  
HETATM    1  C   UNK     0       5.809   1.940   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.271   1.849   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.734   1.758   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.180   3.386   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.466   4.234   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.362   0.311   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.453  -1.226   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       5.944  -1.614   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       6.652  -2.982   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.191  -3.052   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.899  -4.419   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       9.020  -1.754   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       8.312  -0.387   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       9.142   0.910   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      10.680   0.840   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.389  -0.527   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.927  -0.597   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.757   0.700   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.049   2.067   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.510   2.137   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.559  -1.825   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      11.267  -3.192   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.822  -4.279   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.774  -0.317   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0       7.463   1.060   0.000  0.00  0.00           H+0
HETATM   26  C   UNK     0       5.796   0.873   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0       4.544  -2.763   0.000  0.00  0.00           H+0
HETATM   28  N   UNK     0       3.019  -1.788   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       2.631  -3.278   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.146  -3.686   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.727  -4.359   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.042  -0.597   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.504  -0.527   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.205   0.840   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.625   2.137   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.164   2.067   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.872   0.700   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    6                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4                                                            
CONECT    6    2    7   26   37                                             
CONECT    7    6    8   27   28                                             
CONECT    8    7    9   24                                                  
CONECT    9    8   10   23                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   21                                                  
CONECT   13   12   14   24                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
CONECT   21   16   12   22                                                  
CONECT   22   21                                                            
CONECT   23    9                                                            
CONECT   24    8   13   25   26                                             
CONECT   25   24                                                            
CONECT   26   24    6                                                       
CONECT   27    7                                                            
CONECT   28    7   29   32                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   28   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   32    6                                                  
MASTER        0    0    0    0    0    0    0    0   37    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₂₈N₄O₃

Average Mass

468.5570 Da

Monoisotopic Mass

468.21614 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

[H][C@@]12C[C@@]3(C4=CC=CC=C4N(C(C)=O)[C@@]3([H])N1C(=O)[C@@H](C)N1C(=O)C3=C(C=CC=C3)N=C21)C(C)(C)C=C

InChI Identifier

InChI=1S/C28H28N4O3/c1-6-27(4,5)28-15-22-23-29-20-13-9-7-11-18(20)25(35)30(23)16(2)24(34)32(22)26(28)31(17(3)33)21-14-10-8-12-19(21)28/h6-14,16,22,26H,1,15H2,2-5H3/t16-,22+,26+,28+/m1/s1

InChI Key

XTLQWSBGQKPGCF-FAZGTRELSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyrroloindoles

Direct Parent

Pyrroloindoles

Alternative Parents

Substituents

Pyrroloindole
Diazanaphthalene
Quinazoline
Indole
Pyrimidone
Benzenoid
Pyrimidine
Heteroaromatic compound
Acetamide
Tertiary carboxylic acid amide
Pyrrolidine
Pyrrole
Lactam
Carboxamide group
Azacycle
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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

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

162966238

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 5-N-Acetyladreemin (NP0331158)

MOL for NP0331158 (5-N-Acetyladreemin)

3D MOL for NP0331158 (5-N-Acetyladreemin)

3D SDF for NP0331158 (5-N-Acetyladreemin)

3D-SDF for NP0331158 (5-N-Acetyladreemin)

PDB for NP0331158 (5-N-Acetyladreemin)

3D PDB for NP0331158 (5-N-Acetyladreemin)

SMILES for NP0331158 (5-N-Acetyladreemin)

INCHI for NP0331158 (5-N-Acetyladreemin)

Structure for NP0331158 (5-N-Acetyladreemin)

3D Structure for NP0331158 (5-N-Acetyladreemin)