NP-MRD: Showing NP-Card for Asterriquinone SU-5228 (NP0001644)

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Record Information

Version

1.0

Created at

2020-09-23 01:59:56 UTC

Updated at

2021-08-10 02:55:58 UTC

NP-MRD ID

NP0001644

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Asterriquinone SU-5228

Provided By

NPAtlas

Description

Asterriquinone SU-5228 is found in Aspergillus candidus. It was first documented in 1999 (PMID: 10348035). Based on a literature review very few articles have been published on 2,5-dihydroxy-3-(1H-indol-3-yl)-6-[2-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]cyclohexa-2,5-diene-1,4-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117443D          

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     RDKit          3D

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M  END


  Mrv1652306242117443D          

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   -5.9523   -0.7131    1.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7710   -2.3844    0.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3693   -0.3933    2.0539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0576   -0.0583    1.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8366    1.0793   -0.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9196    2.9187   -2.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5734    4.1858   -4.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0753    3.9056   -3.9800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0633    2.4155   -2.3305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4170   -2.6130   -0.1620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8605    1.2312    2.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3719    0.6339    2.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1920   -0.7438    1.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3582   -1.9538   -0.8589 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3012   -2.1821   -2.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1400   -1.2330   -1.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6673    3.4458    0.5894 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
  2  4  2  3  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  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  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  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
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 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
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 20 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 14  6  2  0  0  0  0
 32 15  1  0  0  0  0
 13  8  1  0  0  0  0
 29 21  1  0  0  0  0
 29 24  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  3 37  1  0  0  0  0
  3 38  1  0  0  0  0
  3 39  1  0  0  0  0
  4 40  1  0  0  0  0
  5 41  1  0  0  0  0
  5 42  1  0  0  0  0
  7 43  1  0  0  0  0
  9 44  1  0  0  0  0
 10 45  1  0  0  0  0
 11 46  1  0  0  0  0
 12 47  1  0  0  0  0
 17 48  1  0  0  0  0
 22 49  1  0  0  0  0
 23 50  1  0  0  0  0
 25 51  1  0  0  0  0
 26 52  1  0  0  0  0
 27 53  1  0  0  0  0
 28 54  1  0  0  0  0
 31 55  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001644

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(C2=C([H])N([H])C3=C([H])C([H])=C([H])C([H])=C23)C(=O)C(O[H])=C(C2=C(N([H])C3=C([H])C([H])=C([H])C([H])=C23)C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H22N2O4/c1-14(2)11-12-20-21(16-8-4-6-10-19(16)29-20)23-26(32)24(30)22(25(31)27(23)33)17-13-28-18-9-5-3-7-15(17)18/h3-11,13,28-30,33H,12H2,1-2H3

> <INCHI_KEY>
PTNWHJCGKAMDRN-UHFFFAOYSA-N

> <FORMULA>
C27H22N2O4

> <MOLECULAR_WEIGHT>
438.483

> <EXACT_MASS>
438.157957196

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
48.49161497592438

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,5-dihydroxy-3-(1H-indol-3-yl)-6-[2-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]cyclohexa-2,5-diene-1,4-dione

> <ALOGPS_LOGP>
3.65

> <JCHEM_LOGP>
5.013158688333333

> <ALOGPS_LOGS>
-5.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.49282790114596

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.459326024759875

> <JCHEM_PKA_STRONGEST_BASIC>
-5.202591514717747

> <JCHEM_POLAR_SURFACE_AREA>
106.18

> <JCHEM_REFRACTIVITY>
130.3151

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.14e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,5-dihydroxy-3-(1H-indol-3-yl)-6-[2-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]cyclohexa-2,5-diene-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 55 59  0  0  0  0  0  0  0  0999 V2000
   -4.9639   -3.7734    0.6808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6188   -2.3941    1.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6005   -1.6129    1.8986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4497   -1.7947    0.8122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1429   -0.4266    1.2432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8121    0.5253    0.1530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8200    1.1809   -0.5206 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3081    1.9567   -1.4822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8538    2.8103   -2.4330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1008    3.5186   -3.3360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7294    3.3715   -3.2935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1319    2.5314   -2.3633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9440    1.8422   -1.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6596    0.9354   -0.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2920    0.6059   -0.1244 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2066   -0.5896   -0.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5113   -1.7141   -0.6141 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6376   -0.7671    0.1544 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0756   -1.9410    0.0616 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4895    0.3160    0.5881 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8826    0.1438    0.9589 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4199    0.6712    2.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7236    0.3724    2.1940 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1005   -0.3331    1.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3033   -0.8545    0.6791 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4048   -1.5299   -0.5108 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2500   -1.6535   -1.2528 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0332   -1.1376   -0.8524 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9387   -0.4639    0.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9403    1.5340    0.6626 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7819    2.5590    1.0839 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5508    1.7554    0.3204 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0656    2.9152    0.4007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0163   -3.8705    0.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2507   -4.1769   -0.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8640   -4.4213    1.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0915   -1.4138    2.8853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4991   -2.2178    2.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9523   -0.7131    1.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7710   -2.3844    0.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3693   -0.3933    2.0539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0576   -0.0583    1.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8366    1.0793   -0.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9196    2.9187   -2.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5734    4.1858   -4.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0753    3.9056   -3.9800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0633    2.4155   -2.3305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4170   -2.6130   -0.1620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8605    1.2312    2.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3719    0.6339    2.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1920   -0.7438    1.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3582   -1.9538   -0.8589 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3012   -2.1821   -2.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1400   -1.2330   -1.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6673    3.4458    0.5894 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 20 30  2  0
 30 31  1  0
 30 32  1  0
 32 33  2  0
 14  6  2  0
 32 15  1  0
 13  8  1  0
 29 21  1  0
 29 24  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  4 40  1  0
  5 41  1  0
  5 42  1  0
  7 43  1  0
  9 44  1  0
 10 45  1  0
 11 46  1  0
 12 47  1  0
 17 48  1  0
 22 49  1  0
 23 50  1  0
 25 51  1  0
 26 52  1  0
 27 53  1  0
 28 54  1  0
 31 55  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      -4.964  -3.773   0.681  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.619  -2.394   1.101  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.601  -1.613   1.899  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.450  -1.795   0.812  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.143  -0.427   1.243  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.812   0.525   0.153  0.00  0.00           C+0
HETATM    7  N   UNK     0      -3.820   1.181  -0.521  0.00  0.00           N+0
HETATM    8  C   UNK     0      -3.308   1.957  -1.482  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.854   2.810  -2.433  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.101   3.519  -3.336  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.729   3.372  -3.293  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.132   2.531  -2.363  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.944   1.842  -1.477  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.660   0.935  -0.438  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.292   0.606  -0.124  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.207  -0.590  -0.207  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.511  -1.714  -0.614  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.638  -0.767   0.154  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.076  -1.941   0.062  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.490   0.316   0.588  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.883   0.144   0.959  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.420   0.671   2.145  0.00  0.00           C+0
HETATM   23  N   UNK     0       5.724   0.372   2.194  0.00  0.00           N+0
HETATM   24  C   UNK     0       6.101  -0.333   1.096  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.303  -0.855   0.679  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.405  -1.530  -0.511  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.250  -1.654  -1.253  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.033  -1.138  -0.852  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.939  -0.464   0.340  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.940   1.534   0.663  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.782   2.559   1.084  0.00  0.00           O+0
HETATM   32  C   UNK     0       0.551   1.755   0.320  0.00  0.00           C+0
HETATM   33  O   UNK     0       0.066   2.915   0.401  0.00  0.00           O+0
HETATM   34  H   UNK     0      -6.016  -3.870   0.357  0.00  0.00           H+0
HETATM   35  H   UNK     0      -4.251  -4.177  -0.063  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.864  -4.421   1.582  0.00  0.00           H+0
HETATM   37  H   UNK     0      -5.091  -1.414   2.885  0.00  0.00           H+0
HETATM   38  H   UNK     0      -6.499  -2.218   2.166  0.00  0.00           H+0
HETATM   39  H   UNK     0      -5.952  -0.713   1.391  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.771  -2.384   0.249  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.369  -0.393   2.054  0.00  0.00           H+0
HETATM   42  H   UNK     0      -4.058  -0.058   1.811  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.837   1.079  -0.305  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.920   2.919  -2.459  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.573   4.186  -4.076  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.075   3.906  -3.980  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.063   2.416  -2.330  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.417  -2.613  -0.162  0.00  0.00           H+0
HETATM   49  H   UNK     0       3.861   1.231   2.897  0.00  0.00           H+0
HETATM   50  H   UNK     0       6.372   0.634   2.954  0.00  0.00           H+0
HETATM   51  H   UNK     0       8.192  -0.744   1.279  0.00  0.00           H+0
HETATM   52  H   UNK     0       8.358  -1.954  -0.859  0.00  0.00           H+0
HETATM   53  H   UNK     0       6.301  -2.182  -2.195  0.00  0.00           H+0
HETATM   54  H   UNK     0       4.140  -1.233  -1.453  0.00  0.00           H+0
HETATM   55  H   UNK     0       2.667   3.446   0.589  0.00  0.00           H+0
CONECT    1    2   34   35   36                                             
CONECT    2    1    3    4                                                  
CONECT    3    2   37   38   39                                             
CONECT    4    2    5   40                                                  
CONECT    5    4    6   41   42                                             
CONECT    6    5    7   14                                                  
CONECT    7    6    8   43                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10   44                                                  
CONECT   10    9   11   45                                                  
CONECT   11   10   12   46                                                  
CONECT   12   11   13   47                                                  
CONECT   13   12   14    8                                                  
CONECT   14   13   15    6                                                  
CONECT   15   14   16   32                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   48                                                       
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   30                                                  
CONECT   21   20   22   29                                                  
CONECT   22   21   23   49                                                  
CONECT   23   22   24   50                                                  
CONECT   24   23   25   29                                                  
CONECT   25   24   26   51                                                  
CONECT   26   25   27   52                                                  
CONECT   27   26   28   53                                                  
CONECT   28   27   29   54                                                  
CONECT   29   28   21   24                                                  
CONECT   30   20   31   32                                                  
CONECT   31   30   55                                                       
CONECT   32   30   33   15                                                  
CONECT   33   32                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    3                                                            
CONECT   38    3                                                            
CONECT   39    3                                                            
CONECT   40    4                                                            
CONECT   41    5                                                            
CONECT   42    5                                                            
CONECT   43    7                                                            
CONECT   44    9                                                            
CONECT   45   10                                                            
CONECT   46   11                                                            
CONECT   47   12                                                            
CONECT   48   17                                                            
CONECT   49   22                                                            
CONECT   50   23                                                            
CONECT   51   25                                                            
CONECT   52   26                                                            
CONECT   53   27                                                            
CONECT   54   28                                                            
CONECT   55   31                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  118    0
END

RDKit          3D

55 59  0  0  0  0  0  0  0  0999 V2000
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   -4.6188   -2.3941    1.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6005   -1.6129    1.8986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4497   -1.7947    0.8122 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8200    1.1809   -0.5206 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3081    1.9567   -1.4822 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8826    0.1438    0.9589 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4199    0.6712    2.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7236    0.3724    2.1940 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1005   -0.3331    1.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3033   -0.8545    0.6791 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4048   -1.5299   -0.5108 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2500   -1.6535   -1.2528 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0332   -1.1376   -0.8524 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9387   -0.4639    0.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9403    1.5340    0.6626 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7819    2.5590    1.0839 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5508    1.7554    0.3204 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0656    2.9152    0.4007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0163   -3.8705    0.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2507   -4.1769   -0.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8640   -4.4213    1.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0915   -1.4138    2.8853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4991   -2.2178    2.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9523   -0.7131    1.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7710   -2.3844    0.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3693   -0.3933    2.0539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0576   -0.0583    1.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8366    1.0793   -0.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9196    2.9187   -2.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5734    4.1858   -4.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0753    3.9056   -3.9800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0633    2.4155   -2.3305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4170   -2.6130   -0.1620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8605    1.2312    2.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3719    0.6339    2.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1920   -0.7438    1.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3582   -1.9538   -0.8589 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3012   -2.1821   -2.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1400   -1.2330   -1.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6673    3.4458    0.5894 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
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 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 20 30  2  0
 30 31  1  0
 30 32  1  0
 32 33  2  0
 14  6  2  0
 32 15  1  0
 13  8  1  0
 29 21  1  0
 29 24  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  4 40  1  0
  5 41  1  0
  5 42  1  0
  7 43  1  0
  9 44  1  0
 10 45  1  0
 11 46  1  0
 12 47  1  0
 17 48  1  0
 22 49  1  0
 23 50  1  0
 25 51  1  0
 26 52  1  0
 27 53  1  0
 28 54  1  0
 31 55  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₇H₂₂N₂O₄

Average Mass

438.4830 Da

Monoisotopic Mass

438.15796 Da

IUPAC Name

2,5-dihydroxy-3-(1H-indol-3-yl)-6-[2-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]cyclohexa-2,5-diene-1,4-dione

Traditional Name

2,5-dihydroxy-3-(1H-indol-3-yl)-6-[2-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]cyclohexa-2,5-diene-1,4-dione

CAS Registry Number

Not Available

SMILES

[H]OC1=C(C2=C([H])N([H])C3=C([H])C([H])=C([H])C([H])=C23)C(=O)C(O[H])=C(C2=C(N([H])C3=C([H])C([H])=C([H])C([H])=C23)C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C1=O

InChI Identifier

InChI=1S/C27H22N2O4/c1-14(2)11-12-20-21(16-8-4-6-10-19(16)29-20)23-26(32)24(30)22(25(31)27(23)33)17-13-28-18-9-5-3-7-15(17)18/h3-11,13,28-30,33H,12H2,1-2H3

InChI Key

PTNWHJCGKAMDRN-UHFFFAOYSA-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 candidus	NPAtlas	10348035

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	3.65	ALOGPS
logP	5.01	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	5.46	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	106.18 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	130.32 m³·mol⁻¹	ChemAxon
Polarizability	48.49 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA009622

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00016136

Chemspider ID

8289546

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10114023

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Alvi KA, Pu H, Luche M, Rice A, App H, McMahon G, Dare H, Margolis B: Asterriquinones produced by Aspergillus candidus inhibit binding of the Grb-2 adapter to phosphorylated EGF receptor tyrosine kinase. J Antibiot (Tokyo). 1999 Mar;52(3):215-23. doi: 10.7164/antibiotics.52.215. [PubMed:10348035 ]

Showing NP-Card for Asterriquinone SU-5228 (NP0001644)

MOL for NP0001644 (Asterriquinone SU-5228)

3D MOL for NP0001644 (Asterriquinone SU-5228)

3D SDF for NP0001644 (Asterriquinone SU-5228)

3D-SDF for NP0001644 (Asterriquinone SU-5228)

PDB for NP0001644 (Asterriquinone SU-5228)

3D PDB for NP0001644 (Asterriquinone SU-5228)

SMILES for NP0001644 (Asterriquinone SU-5228)

INCHI for NP0001644 (Asterriquinone SU-5228)

Structure for NP0001644 (Asterriquinone SU-5228)

3D Structure for NP0001644 (Asterriquinone SU-5228)