NP-MRD: Showing NP-Card for Aspergillazine C (NP0005614)

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Record Information

Version

2.0

Created at

2020-12-09 02:49:14 UTC

Updated at

2021-07-15 16:52:30 UTC

NP-MRD ID

NP0005614

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aspergillazine C

Provided By

NPAtlas

Description

Aspergillazine C belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). Aspergillazine C is found in Aspergillus unilateralis. Aspergillazine C was first documented in 2015 (PMID: 26084356). Based on a literature review very few articles have been published on Aspergillazine C.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118213D          

 53 56  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306242118213D          

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   -3.2126    1.9580   -0.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0545    1.2153    2.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2202    1.7328   -0.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9955    2.6285   -1.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7035   -0.6625   -1.7967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4764    1.1328   -1.7122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3232   -1.8464    0.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6632   -2.2225    1.7900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9265   -0.6722    2.1304 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1436   -1.8135    2.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0586   -1.2257    3.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8136   -0.8305    3.9597 H   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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 10  1  6  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  8 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 29  3  1  0  0  0  0
 28  6  1  0  0  0  0
 24 12  1  0  0  0  0
 23 15  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  4 35  1  0  0  0  0
  5 36  1  0  0  0  0
  7 37  1  0  0  0  0
  9 38  1  0  0  0  0
 13 39  1  0  0  0  0
 13 40  1  0  0  0  0
 14 41  1  0  0  0  0
 14 42  1  0  0  0  0
 16 43  1  0  0  0  0
 17 44  1  1  0  0  0
 18 45  1  0  0  0  0
 19 46  1  6  0  0  0
 20 47  1  0  0  0  0
 21 48  1  0  0  0  0
 22 49  1  0  0  0  0
 23 50  1  1  0  0  0
 31 51  1  0  0  0  0
 31 52  1  0  0  0  0
 31 53  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0005614

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])C([H])=C([H])[C@@]2([H])S[C@](N([H])[H])(C(=O)N([H])C3=C([H])C4=C([H])C([H])=C(OC([H])([H])[H])C(OC([H])([H])[H])=C4OC3=O)C([H])([H])[C@@]2(O[H])[C@@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H22N2O8S/c1-28-12-5-3-9-7-10(17(25)30-14(9)15(12)29-2)22-18(26)20(21)8-19(27)13(31-20)6-4-11(23)16(19)24/h3-7,11,13,16,23-24,27H,8,21H2,1-2H3,(H,22,26)/t11-,13-,16+,19+,20+/m1/s1

> <INCHI_KEY>
LDSUQPVEEKUWMR-SEQHAUAXSA-N

> <FORMULA>
C20H22N2O8S

> <MOLECULAR_WEIGHT>
450.46

> <EXACT_MASS>
450.10968685

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
44.678722114936036

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3aR,4S,5R,7aR)-2-amino-N-(7,8-dimethoxy-2-oxo-2H-chromen-3-yl)-3a,4,5-trihydroxy-2,3,3a,4,5,7a-hexahydro-1-benzothiophene-2-carboxamide

> <ALOGPS_LOGP>
0.78

> <JCHEM_LOGP>
-0.6544970669999997

> <ALOGPS_LOGS>
-2.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.78208451811308

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.03910082563633

> <JCHEM_PKA_STRONGEST_BASIC>
6.091099143520171

> <JCHEM_POLAR_SURFACE_AREA>
160.57

> <JCHEM_REFRACTIVITY>
111.42419999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.60e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3aR,4S,5R,7aR)-2-amino-N-(7,8-dimethoxy-2-oxochromen-3-yl)-3a,4,5-trihydroxy-3,4,5,7a-tetrahydro-1-benzothiophene-2-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 53 56  0  0  0  0  0  0  0  0999 V2000
    8.3917   -0.1125   -0.6727 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4914   -0.0120    0.4069 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1389   -0.0205    0.1746 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6610   -0.1267   -1.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3064   -0.1361   -1.3471 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3816   -0.0384   -0.3035 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0123   -0.0482   -0.5515 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1117    0.0484    0.4824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2784    0.0491    0.3521 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0043   -0.0468   -0.8266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4514   -0.1485   -1.9428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5025   -0.0366   -0.8605 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9816   -0.1611   -2.1921 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0502    1.0836   -0.0749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3610    0.7358    0.5287 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5305    1.6017    1.6167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4592    1.0251   -0.4399 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9410    1.6442   -1.5940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2101   -0.1854   -0.9133 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.4806    0.1878   -1.4133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4247   -1.2293    0.0831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5323   -1.4326    1.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3184   -0.6362    1.0840 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0454   -1.4910    0.0793 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.7012    0.1533    1.7589 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9051    0.2447    2.7422 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9776    0.1585    1.9442 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8549    0.0679    0.9778 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2295    0.0762    1.2088 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7083    0.1838    2.5057 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9462   -0.9615    3.2802 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1991    0.7567   -1.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1490   -1.0137   -1.2974 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4426   -0.1324   -0.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3613   -0.2029   -1.9230 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8867   -0.2182   -2.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6912   -0.1329   -1.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8496    0.1311    1.2474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6028   -1.0517   -2.5980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6665    0.5949   -2.8440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2971    1.4383    0.6609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2126    1.9580   -0.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0545    1.2153    2.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2202    1.7328   -0.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9955    2.6285   -1.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7035   -0.6625   -1.7967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4764    1.1328   -1.7122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3232   -1.8464    0.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6632   -2.2225    1.7900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9265   -0.6722    2.1304 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1436   -1.8135    2.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0586   -1.2257    3.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8136   -0.8305    3.9597 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 12 10  1  6
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  1
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
  8 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
 29  3  1  0
 28  6  1  0
 24 12  1  0
 23 15  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  5 36  1  0
  7 37  1  0
  9 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 16 43  1  0
 17 44  1  1
 18 45  1  0
 19 46  1  6
 20 47  1  0
 21 48  1  0
 22 49  1  0
 23 50  1  1
 31 51  1  0
 31 52  1  0
 31 53  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       8.392  -0.113  -0.673  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.491  -0.012   0.407  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.139  -0.021   0.175  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.661  -0.127  -1.105  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.306  -0.136  -1.347  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.382  -0.038  -0.304  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.012  -0.048  -0.552  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.112   0.048   0.482  0.00  0.00           C+0
HETATM    9  N   UNK     0      -0.278   0.049   0.352  0.00  0.00           N+0
HETATM   10  C   UNK     0      -1.004  -0.047  -0.827  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.451  -0.149  -1.943  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.502  -0.037  -0.861  0.00  0.00           C+0
HETATM   13  N   UNK     0      -2.982  -0.161  -2.192  0.00  0.00           N+0
HETATM   14  C   UNK     0      -3.050   1.084  -0.075  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.361   0.736   0.529  0.00  0.00           C+0
HETATM   16  O   UNK     0      -4.531   1.602   1.617  0.00  0.00           O+0
HETATM   17  C   UNK     0      -5.459   1.025  -0.440  0.00  0.00           C+0
HETATM   18  O   UNK     0      -4.941   1.644  -1.594  0.00  0.00           O+0
HETATM   19  C   UNK     0      -6.210  -0.185  -0.913  0.00  0.00           C+0
HETATM   20  O   UNK     0      -7.481   0.188  -1.413  0.00  0.00           O+0
HETATM   21  C   UNK     0      -6.425  -1.229   0.083  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.532  -1.433   1.015  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.318  -0.636   1.084  0.00  0.00           C+0
HETATM   24  S   UNK     0      -3.045  -1.491   0.079  0.00  0.00           S+0
HETATM   25  C   UNK     0       1.701   0.153   1.759  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.905   0.245   2.742  0.00  0.00           O+0
HETATM   27  O   UNK     0       2.978   0.159   1.944  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.855   0.068   0.978  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.229   0.076   1.209  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.708   0.184   2.506  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.946  -0.962   3.280  0.00  0.00           C+0
HETATM   32  H   UNK     0       8.199   0.757  -1.365  0.00  0.00           H+0
HETATM   33  H   UNK     0       8.149  -1.014  -1.297  0.00  0.00           H+0
HETATM   34  H   UNK     0       9.443  -0.132  -0.344  0.00  0.00           H+0
HETATM   35  H   UNK     0       6.361  -0.203  -1.923  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.887  -0.218  -2.342  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.691  -0.133  -1.567  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.850   0.131   1.247  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.603  -1.052  -2.598  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.667   0.595  -2.844  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.297   1.438   0.661  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.213   1.958  -0.772  0.00  0.00           H+0
HETATM   43  H   UNK     0      -5.054   1.215   2.342  0.00  0.00           H+0
HETATM   44  H   UNK     0      -6.220   1.733  -0.045  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.995   2.628  -1.537  0.00  0.00           H+0
HETATM   46  H   UNK     0      -5.704  -0.663  -1.797  0.00  0.00           H+0
HETATM   47  H   UNK     0      -7.476   1.133  -1.712  0.00  0.00           H+0
HETATM   48  H   UNK     0      -7.323  -1.846   0.062  0.00  0.00           H+0
HETATM   49  H   UNK     0      -5.663  -2.223   1.790  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.926  -0.672   2.130  0.00  0.00           H+0
HETATM   51  H   UNK     0       6.144  -1.813   2.598  0.00  0.00           H+0
HETATM   52  H   UNK     0       5.059  -1.226   3.889  0.00  0.00           H+0
HETATM   53  H   UNK     0       6.814  -0.831   3.960  0.00  0.00           H+0
CONECT    1    2   32   33   34                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   29                                                  
CONECT    4    3    5   35                                                  
CONECT    5    4    6   36                                                  
CONECT    6    5    7   28                                                  
CONECT    7    6    8   37                                                  
CONECT    8    7    9   25                                                  
CONECT    9    8   10   38                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14   24                                             
CONECT   13   12   39   40                                                  
CONECT   14   12   15   41   42                                             
CONECT   15   14   16   17   23                                             
CONECT   16   15   43                                                       
CONECT   17   15   18   19   44                                             
CONECT   18   17   45                                                       
CONECT   19   17   20   21   46                                             
CONECT   20   19   47                                                       
CONECT   21   19   22   48                                                  
CONECT   22   21   23   49                                                  
CONECT   23   22   24   15   50                                             
CONECT   24   23   12                                                       
CONECT   25    8   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29    6                                                  
CONECT   29   28   30    3                                                  
CONECT   30   29   31                                                       
CONECT   31   30   51   52   53                                             
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    4                                                            
CONECT   36    5                                                            
CONECT   37    7                                                            
CONECT   38    9                                                            
CONECT   39   13                                                            
CONECT   40   13                                                            
CONECT   41   14                                                            
CONECT   42   14                                                            
CONECT   43   16                                                            
CONECT   44   17                                                            
CONECT   45   18                                                            
CONECT   46   19                                                            
CONECT   47   20                                                            
CONECT   48   21                                                            
CONECT   49   22                                                            
CONECT   50   23                                                            
CONECT   51   31                                                            
CONECT   52   31                                                            
CONECT   53   31                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  112    0
END

RDKit          3D

53 56  0  0  0  0  0  0  0  0999 V2000
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   -4.3184   -0.6362    1.0840 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.7012    0.1533    1.7589 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9051    0.2447    2.7422 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9776    0.1585    1.9442 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8549    0.0679    0.9778 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2295    0.0762    1.2088 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7083    0.1838    2.5057 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9462   -0.9615    3.2802 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.4426   -0.1324   -0.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3613   -0.2029   -1.9230 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8867   -0.2182   -2.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6912   -0.1329   -1.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8496    0.1311    1.2474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6028   -1.0517   -2.5980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6665    0.5949   -2.8440 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2126    1.9580   -0.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0545    1.2153    2.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2202    1.7328   -0.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9955    2.6285   -1.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7035   -0.6625   -1.7967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4764    1.1328   -1.7122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3232   -1.8464    0.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6632   -2.2225    1.7900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9265   -0.6722    2.1304 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1436   -1.8135    2.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0586   -1.2257    3.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8136   -0.8305    3.9597 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
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  8 25  1  0
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 30 31  1  0
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  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
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 31 51  1  0
 31 52  1  0
 31 53  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Aspergillazine b	MeSH
Aspergillazine a	MeSH
Aspergillazine D	MeSH
Aspergillazine e	MeSH
(3AR,4S,5R,7ar)-2-amino-N-(7,8-dimethoxy-2-oxo-2H-chromen-3-yl)-3a,4,5-trihydroxy-2,3,3a,4,5,7a-hexahydro-1-benzothiophene-2-carboximidate	Generator

Chemical Formula

C₂₀H₂₂N₂O₈S

Average Mass

450.4600 Da

Monoisotopic Mass

450.10969 Da

IUPAC Name

(2S,3aR,4S,5R,7aR)-2-amino-N-(7,8-dimethoxy-2-oxo-2H-chromen-3-yl)-3a,4,5-trihydroxy-2,3,3a,4,5,7a-hexahydro-1-benzothiophene-2-carboxamide

Traditional Name

(2S,3aR,4S,5R,7aR)-2-amino-N-(7,8-dimethoxy-2-oxochromen-3-yl)-3a,4,5-trihydroxy-3,4,5,7a-tetrahydro-1-benzothiophene-2-carboxamide

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C2=C(C=C1)C=C(NC(=O)C1(N)C[C@]3(O)[C@H](S1)C=C[C@@H](O)[C@@H]3O)C(=O)O2

InChI Identifier

InChI=1S/C20H22N2O8S/c1-28-12-5-3-9-7-10(17(25)30-14(9)15(12)29-2)22-18(26)20(21)8-19(27)13(31-20)6-4-11(23)16(19)24/h3-7,11,13,16,23-24,27H,8,21H2,1-2H3,(H,22,26)/t11-,13-,16+,19+,20?/m1/s1

InChI Key

LDSUQPVEEKUWMR-SEQHAUAXSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Aspergillus unilateralis	NPAtlas	15602607

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Not Available

Direct Parent

Coumarins and derivatives

Alternative Parents

Substituents

Coumarin
Alpha-amino acid or derivatives
Benzopyran
1-benzopyran
Anisole
Phenol ether
N-arylamide
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Tertiary alcohol
Thiolane
Amino acid or derivatives
Secondary carboxylic acid amide
Secondary alcohol
Lactone
Carboxamide group
1,2-diol
Polyol
Thioether
Hemithioaminal
Dialkylthioether
Organoheterocyclic compound
Ether
Oxacycle
Carboxylic acid derivative
Organic nitrogen compound
Organonitrogen compound
Carbonyl group
Organooxygen compound
Primary amine
Hydrocarbon derivative
Amine
Organic oxide
Organic oxygen compound
Alcohol
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
logP	0.78	ALOGPS
logP	-0.65	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	12.04	ChemAxon
pKa (Strongest Basic)	6.09	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	160.57 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	111.42 m³·mol⁻¹	ChemAxon
Polarizability	44.68 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA006419

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10363397

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23250924

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Mfuh AM, Zhang Y, Stephens DE, Vo AX, Arman HD, Larionov OV: Concise Total Synthesis of Trichodermamides A, B, and C Enabled by an Efficient Construction of the 1,2-Oxazadecaline Core. J Am Chem Soc. 2015 Jul 1;137(25):8050-3. doi: 10.1021/jacs.5b05205. Epub 2015 Jun 22. [PubMed:26084356 ]

Showing NP-Card for Aspergillazine C (NP0005614)

MOL for NP0005614 (Aspergillazine C)

3D MOL for NP0005614 (Aspergillazine C)

3D SDF for NP0005614 (Aspergillazine C)

3D-SDF for NP0005614 (Aspergillazine C)

PDB for NP0005614 (Aspergillazine C)

3D PDB for NP0005614 (Aspergillazine C)

SMILES for NP0005614 (Aspergillazine C)

INCHI for NP0005614 (Aspergillazine C)

Structure for NP0005614 (Aspergillazine C)

3D Structure for NP0005614 (Aspergillazine C)