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Showing NP-Card for 3-epi-notoamide C (NP0331617)

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Record Information
Version2.0
Created at2023-05-05 12:01:03 UTC
Updated at2024-09-03 04:16:17 UTC
NP-MRD IDNP0331617
Natural Product DOIhttps://doi.org/10.57994/0605
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-epi-notoamide C
DescriptionNotoamide C belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. Notoamide C is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. It was first documented in 2011 (PMID: 22140279). Based on a literature review a significant number of articles have been published on notoamide C (PMID: 22140281) (PMID: 22188465) (PMID: 23213353) (PMID: 26061478) (PMID: 26287214) (PMID: 32672903).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0331617 (3-epi-notoamide C)


  Mrv1652305052314012D          

 35 39  0  0  1  0            999 V2000
    5.8534   -2.6301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3383   -3.2976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0028   -4.0512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2491   -3.7157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7565   -4.3868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6672   -4.8049    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4518   -5.0599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1663   -4.6474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8808   -5.0599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4518   -5.8849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6672   -6.1398    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1663   -6.2974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8808   -5.8849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5953   -6.2974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5953   -7.1224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4077   -6.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8774   -7.8976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8808   -7.5349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1663   -7.1224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9528   -4.3924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2383   -4.8049    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2383   -3.9799    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2383   -5.6299    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5238   -6.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8093   -5.6299    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0247   -5.8849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5398   -5.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0247   -4.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5238   -5.2174    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8093   -4.8049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5238   -4.3924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5238   -3.5674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5238   -6.8674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1823   -5.4724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149   -5.9573    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  1  0  0  0  0
  3  5  1  0  0  0  0
  6  3  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  7 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  2  0  0  0  0
 12 19  1  0  0  0  0
  6 20  1  6  0  0  0
 21 20  1  6  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 25 29  1  1  0  0  0
 25 30  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 21 31  1  0  0  0  0
 31 32  2  0  0  0  0
 24 33  2  0  0  0  0
  6 34  1  0  0  0  0
 11 34  1  0  0  0  0
 34 35  2  0  0  0  0
M  END
Download

3D MOL for NP0331617 (3-epi-notoamide C)

Download
3D SDF for NP0331617 (3-epi-notoamide C)

  Mrv1652305052314012D          

 35 39  0  0  1  0            999 V2000
    5.8534   -2.6301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3383   -3.2976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0028   -4.0512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2491   -3.7157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7565   -4.3868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6672   -4.8049    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4518   -5.0599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1663   -4.6474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8808   -5.0599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4518   -5.8849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6672   -6.1398    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1663   -6.2974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8808   -5.8849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5953   -6.2974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5953   -7.1224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4077   -6.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8774   -7.8976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8808   -7.5349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1663   -7.1224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9528   -4.3924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2383   -4.8049    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2383   -3.9799    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2383   -5.6299    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5238   -6.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8093   -5.6299    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0247   -5.8849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5398   -5.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0247   -4.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5238   -5.2174    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8093   -4.8049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5238   -4.3924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5238   -3.5674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5238   -6.8674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1823   -5.4724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149   -5.9573    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  1  0  0  0  0
  3  5  1  0  0  0  0
  6  3  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  7 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  2  0  0  0  0
 12 19  1  0  0  0  0
  6 20  1  6  0  0  0
 21 20  1  6  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 25 29  1  1  0  0  0
 25 30  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 21 31  1  0  0  0  0
 31 32  2  0  0  0  0
 24 33  2  0  0  0  0
  6 34  1  0  0  0  0
 11 34  1  0  0  0  0
 34 35  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0331617

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CCCN1C(=O)[C@]([H])(C[C@]1(C(=O)NC3=C1C=CC1=C3C=CC(C)(C)O1)C(C)(C)C=C)NC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H31N3O4/c1-6-24(2,3)26(14-17-22(31)29-13-7-8-18(29)21(30)27-17)16-9-10-19-15(20(16)28-23(26)32)11-12-25(4,5)33-19/h6,9-12,17-18H,1,7-8,13-14H2,2-5H3,(H,27,30)(H,28,32)/t17-,18-,26-/m0/s1

> <INCHI_KEY>
KNFZHRYXLWKRSU-XWXLMPLOSA-N

> <FORMULA>
C26H31N3O4

> <MOLECULAR_WEIGHT>
449.551

> <EXACT_MASS>
449.23145649

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
47.408817142811145

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,8aS)-3-{[(3S)-7,7-dimethyl-3-(2-methylbut-3-en-2-yl)-2-oxo-1H,2H,3H,7H-chromeno[5,6-b]pyrrol-3-yl]methyl}-octahydropyrrolo[1,2-a]pyrazine-1,4-dione

> <JCHEM_LOGP>
2.6131764746666657

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.589835768448967

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.905992734907844

> <JCHEM_PKA_STRONGEST_BASIC>
-3.264973971031447

> <JCHEM_POLAR_SURFACE_AREA>
87.74000000000001

> <JCHEM_REFRACTIVITY>
127.12729999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S,8aS)-3-{[(3S)-7,7-dimethyl-3-(2-methylbut-3-en-2-yl)-2-oxo-1H-chromeno[5,6-b]pyrrol-3-yl]methyl}-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0331617 (3-epi-notoamide C)
Download
PDB for NP0331617 (3-epi-notoamide C)
HEADER    PROTEIN                                 05-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-MAY-23         0                                  
HETATM    1  C   UNK     0      10.926  -4.910   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.832  -6.155   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.205  -7.562   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.798  -6.936   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.612  -8.189   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.579  -8.969   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.043  -9.445   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.377  -8.675   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.711  -9.445   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.043 -10.985   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      10.579 -11.461   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      13.377 -11.755   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.711 -10.985   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      16.044 -11.755   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      16.044 -13.295   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.561 -13.028   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.571 -14.742   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.711 -14.065   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.377 -13.295   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.245  -8.199   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.911  -8.969   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0       7.911  -7.429   0.000  0.00  0.00           H+0
HETATM   23  N   UNK     0       7.911 -10.509   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       6.578 -11.279   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.244 -10.509   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.779 -10.985   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.874  -9.739   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.779  -8.493   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0       6.578  -9.739   0.000  0.00  0.00           H+0
HETATM   30  N   UNK     0       5.244  -8.969   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0       6.578  -8.199   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.578  -6.659   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       6.578 -12.819   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       9.674 -10.215   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       8.428 -11.120   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7   20   34                                             
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8   13                                                       
CONECT   10    7   11   12                                                  
CONECT   11   10   34                                                       
CONECT   12   10   13   19                                                  
CONECT   13   12    9   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15   19                                                       
CONECT   19   18   12                                                       
CONECT   20    6   21                                                       
CONECT   21   20   22   23   31                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   33                                                  
CONECT   25   24   26   29   30                                             
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   30                                                       
CONECT   29   25                                                            
CONECT   30   25   28   31                                                  
CONECT   31   30   21   32                                                  
CONECT   32   31                                                            
CONECT   33   24                                                            
CONECT   34    6   11   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

Download
3D PDB for NP0331617 (3-epi-notoamide C)
Download
SMILES for NP0331617 (3-epi-notoamide C)
[H][C@@]12CCCN1C(=O)[C@]([H])(C[C@]1(C(=O)NC3=C1C=CC1=C3C=CC(C)(C)O1)C(C)(C)C=C)NC2=O
Download
INCHI for NP0331617 (3-epi-notoamide C)
InChI=1S/C26H31N3O4/c1-6-24(2,3)26(14-17-22(31)29-13-7-8-18(29)21(30)27-17)16-9-10-19-15(20(16)28-23(26)32)11-12-25(4,5)33-19/h6,9-12,17-18H,1,7-8,13-14H2,2-5H3,(H,27,30)(H,28,32)/t17-,18-,26-/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC26H31N3O4
Average Mass449.5510 Da
Monoisotopic Mass449.23146 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
[H][C@@]12CCCN1C(=O)[C@]([H])(C[C@]1(C(=O)NC3=C1C=CC1=C3C=CC(C)(C)O1)C(C)(C)C=C)NC2=O
InChI Identifier
InChI=1S/C26H31N3O4/c1-6-24(2,3)26(14-17-22(31)29-13-7-8-18(29)21(30)27-17)16-9-10-19-15(20(16)28-23(26)32)11-12-25(4,5)33-19/h6,9-12,17-18H,1,7-8,13-14H2,2-5H3,(H,27,30)(H,28,32)/t17-,18-,26-/m0/s1
InChI KeyKNFZHRYXLWKRSU-XWXLMPLOSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 400, C3D6O, simulated)zhangcuixian@gzucm.edu.cnguangzhou university of Chinese medicinezhangcuixian2024-05-11View Spectrum
Species
Species of Origin
Species NameSourceReference
versicolor CGF 9-1-2
      Not Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassBenzopyrans  
Sub Class1-benzopyrans  
Direct Parent2,2-dimethyl-1-benzopyrans  
Alternative Parents
Substituents
  • 2,2-dimethyl-1-benzopyran
    • 

  • Alpha-amino acid or derivatives
    • 

  • Indole or derivatives
    • 

  • Dihydroindole
    • 

  • Dioxopiperazine
    • 

  • 2,5-dioxopiperazine
    • 

  • Alkyl aryl ether
    • 

  • N-alkylpiperazine
    • 

  • 1,4-diazinane
    • 

  • Benzenoid
    • 

  • Piperazine
    • 

  • Tertiary carboxylic acid amide
    • 

  • Pyrrolidine
    • 

  • Carboxamide group
    • 

  • Lactam
    • 

  • Secondary carboxylic acid amide
    • 

  • Azacycle
    • 

  • Ether
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic nitrogen compound
    • 

  • Carbonyl group
    • 

  • Organonitrogen compound
    • 

  • Organooxygen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00039873  
Chemspider ID21447233  
KEGG Compound IDNot Available
BioCyc IDCPD-17362  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound25163938  
PDB IDNot Available
ChEBI ID145685  
Good Scents IDNot Available
References
General References
  1. Finefield JM, Greshock TJ, Sherman DH, Tsukamoto S, Williams RM: Notoamide E: Biosynthetic incorporation into notoamides C and D in cultures of Aspergillus versicolor NRRL 35600. Tetrahedron Lett. 2011 Apr 20;52(16):1987-1989. doi: 10.1016/j.tetlet.2011.02.078. [PubMed:22140279  ] 
  2. Kato H, Nakamura Y, Finefield JM, Umaoka H, Nakahara T, Williams RM, Tsukamoto S: Study on the biosynthesis of the notoamides: Pinacol-type rearrangement of the isoprenyl unit in deoxybrevianamide E and 6-hydroxydeoxybrevianamide E. Tetrahedron Lett. 2011 Dec 21;52(51):6923-6926. doi: 10.1016/j.tetlet.2011.10.065. [PubMed:22140281  ] 
  3. Li S, Finefield JM, Sunderhaus JD, McAfoos TJ, Williams RM, Sherman DH: Biochemical characterization of NotB as an FAD-dependent oxidase in the biosynthesis of notoamide indole alkaloids. J Am Chem Soc. 2012 Jan 18;134(2):788-91. doi: 10.1021/ja2093212. Epub 2011 Dec 28. [PubMed:22188465  ] 
  4. Li S, Anand K, Tran H, Yu F, Finefield JM, Sunderhaus JD, McAfoos TJ, Tsukamoto S, Williams RM, Sherman DH: Comparative analysis of the biosynthetic systems for fungal bicyclo[2.2.2]diazaoctane indole alkaloids: the (+)/(-)-notoamide, paraherquamide and malbrancheamide pathways. Medchemcomm. 2012 Aug;3(8):987-996. doi: 10.1039/C2MD20029E. [PubMed:23213353  ] 
  5. Wang B, Park EM, King JB, Mattes AO, Nimmo SL, Clendinen C, Edison AS, Anklin C, Cichewicz RH: Transferring Fungi to a Deuterium-Enriched Medium Results in Assorted, Conditional Changes in Secondary Metabolite Production. J Nat Prod. 2015 Jun 26;78(6):1415-21. doi: 10.1021/acs.jnatprod.5b00337. Epub 2015 Jun 10. [PubMed:26061478  ] 
  6. Netz N, Opatz T: Marine Indole Alkaloids. Mar Drugs. 2015 Aug 6;13(8):4814-914. doi: 10.3390/md13084814. [PubMed:26287214  ] 
  7. Gao S, Tian WJ, Liao ZJ, Wang GH, Zeng DQ, Liu XZ, Wang XY, Zhou H, Chen HF, Lin T: Chemical Constituents from Endophytic Fungus Annulohypoxylon cf. stygium in Leaves of Anoectochilus roxburghii. Chem Biodivers. 2020 Sep;17(9):e2000424. doi: 10.1002/cbdv.202000424. Epub 2020 Aug 31. [PubMed:32672903  ] 
  8. Dai JM, Mi QL, Li XM, Gang D, Yang GY, Zhang JD, Wang J, Li YK, Yang HY, Miao D, Li ZJ, Hu QF: The anti-TMV potency of the tobacco-derived fungus Aspergillus versicolor and its active alkaloids, as anti-TMV activity inhibitors. Phytochemistry. 2023 Jan;205:113485. doi: 10.1016/j.phytochem.2022.113485. Epub  2022 Nov 5. [PubMed:36334789  ] 
  9. Gao Y, Meng Q, Zhou X, Luo X, Su Z, Chen Z, Huang R, Liu Y, Zhang X: How do environmentally friendly antifouling alkaloids affect marine fouling microbial communities? Sci Total Environ. 2022 May 10;820:152910. doi: 10.1016/j.scitotenv.2021.152910.  Epub 2022 Jan 6. [PubMed:34999079  ] 
  10. Zhang XY, Xu XY, Peng J, Ma CF, Nong XH, Bao J, Zhang GZ, Qi SH: Antifouling potentials of eight deep-sea-derived fungi from the South China Sea. J Ind Microbiol Biotechnol. 2014 Apr;41(4):741-8. doi: 10.1007/s10295-014-1412-9.  Epub 2014 Feb 15. [PubMed:24532297  ] 
  1. Hu JS, He YP, Zhou FG, Wu PP, Chen LY, Ni C, Zhang ZK, Xiao XJ, An LK, He XX, Zhang CX: New Indole Diketopiperazine Alkaloids from Soft Coral-Associated Epiphytic Fungus Aspergillus versicolor CGF 9-1-2. Chem Biodivers. 2023 Jun;20(6):e202300301. doi: 10.1002/cbdv.202300301. Epub 2023  May 17. [PubMed:37097072  ]