NP-MRD: Showing NP-Card for (6s)-6-{[(2s,5s)-3,6-dihydroxy-5-[(4-hydroxyphenyl)methyl]-2,5-dihydropyrazin-2-yl]methyl}-6-hydroxyindolo[2,1-b]quinazolin-12-one (NP0285580)

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Record Information

Version

2.0

Created at

2022-09-09 13:49:08 UTC

Updated at

2022-09-09 13:49:08 UTC

NP-MRD ID

NP0285580

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6s)-6-{[(2s,5s)-3,6-dihydroxy-5-[(4-hydroxyphenyl)methyl]-2,5-dihydropyrazin-2-yl]methyl}-6-hydroxyindolo[2,1-b]quinazolin-12-one

Description

Aspertryptanthrin B belongs to the class of organic compounds known as indoloquinazolines. These are polycyclic aromatic compounds containing an indole fused to a quinazoline. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Quinazoline is a heterocyclic compound consisting of two fused six-membered simple aromatic rings, a benzene ring and a pyrimidine ring. Based on a literature review very few articles have been published on Aspertryptanthrin B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092215492D          

 36 41  0  0  1  0            999 V2000
    2.8119   -0.9235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9745   -0.1146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7562    0.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3754   -0.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1571   -0.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3198    0.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7006    1.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9189    0.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2997    1.5030    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5180    1.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3553    0.4306    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5359    0.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0583   -0.3374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2369   -0.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1069    0.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3706    1.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1920    1.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7990    1.6440    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3137    2.3112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1183    2.4047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6191    3.0616    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9384    3.8223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4392    4.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7585    5.2399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6208    4.3753    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1216    5.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6968    4.9283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0161    4.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8345    4.0637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3337    4.7206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1521    4.6168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0144    5.4813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1960    5.5852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3015    3.6146    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8007    2.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4814    2.1970    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  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
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  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  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  1  0  0  0
 21 20  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 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
 27 33  1  0  0  0  0
 25 34  1  0  0  0  0
 34 35  2  0  0  0  0
 21 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END

     RDKit          3D

 58 63  0  0  0  0  0  0  0  0999 V2000
   -5.9571    0.5754   -0.4472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1068   -0.3053   -0.6972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5012   -1.5684   -1.0817 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.2288   -3.1959   -1.5976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2443   -4.1428   -1.8653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9148   -3.7666   -1.7308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5336   -2.4985   -1.3445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2438   -2.1369   -1.2147 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8820   -0.8807   -0.8320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8027    0.0411   -0.5725 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1310    1.2503   -0.2384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6138    2.5194    0.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7798    3.5902    0.3086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4110    3.4364    0.2575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9198    2.1884   -0.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7683    1.0962   -0.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4976   -0.3257   -0.5971 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7750   -0.3247   -1.7861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8963   -1.1227    0.4971 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4419   -0.7886    1.0189 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4969    0.3407    1.8758 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5702    0.9222    2.1814 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6485    2.0364    3.0244 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8847    0.4322    1.6354 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7872    1.6142    1.3742 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0665    1.1077    0.8236 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2599    0.9499   -0.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4459    0.4801   -1.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4849    0.1516   -0.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6525   -0.3149   -0.7671 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2947    0.3075    1.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1048    0.7793    1.6702 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6688   -0.2499    0.3815 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5541   -0.8178    0.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4520   -1.4593   -1.1823 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5848   -1.1874   -1.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2626   -3.4951   -1.7041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5292   -5.1424   -2.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1422   -4.4978   -1.9373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6955    2.6338    0.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1535    4.5787    0.5455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7538    4.2880    0.4502 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1440    2.0966   -0.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3039    0.5222   -1.9283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8574   -2.1924    0.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5932   -1.1402    1.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6782   -1.6912    1.7278 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8985    2.6680    3.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3744   -0.1980    2.4006 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2962    2.2286    0.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9935    2.1971    2.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4775    1.1929   -1.2404 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5732    0.3648   -2.1181 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4283    0.2671   -1.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1156    0.0485    1.8271 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0249    0.8776    2.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0957   -2.4079   -1.2400 H   0  0  0  0  0  0  0  0  0  0  0  0
 31 30  1  0
 30 29  2  0
 29 28  1  0
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 27 26  1  0
 26 25  1  0
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 35 21  1  0
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 20 18  1  0
 18 19  1  6
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 11 10  1  0
 10  9  2  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 27 33  1  0
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 32 30  1  0
 23 25  1  0
 10 18  1  0
  3  8  1  0
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 31 55  1  0
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 21 48  1  1
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 19 45  1  0
 16 44  1  0
 15 43  1  0
 14 42  1  0
 13 41  1  0
  7 40  1  0
  6 39  1  0
  5 38  1  0
  4 37  1  0
 24 49  1  0
 33 57  1  0
 32 56  1  0
M  END


  Mrv1652309092215492D          

 36 41  0  0  1  0            999 V2000
    2.8119   -0.9235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9745   -0.1146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7562    0.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3754   -0.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1571   -0.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3198    0.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7006    1.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9189    0.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2997    1.5030    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5180    1.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3553    0.4306    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5359    0.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0583   -0.3374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2369   -0.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1069    0.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3706    1.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1920    1.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7990    1.6440    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3137    2.3112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1183    2.4047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6191    3.0616    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9384    3.8223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4392    4.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7585    5.2399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6208    4.3753    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1216    5.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6968    4.9283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0161    4.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8345    4.0637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3337    4.7206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1521    4.6168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0144    5.4813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1960    5.5852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3015    3.6146    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8007    2.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4814    2.1970    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  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
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
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 12 13  2  0  0  0  0
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 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  1  0  0  0
 21 20  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 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
 27 33  1  0  0  0  0
 25 34  1  0  0  0  0
 34 35  2  0  0  0  0
 21 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0285580

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C[C@@H]2N=C(O)[C@H](C[C@]3(O)C4=CC=CC=C4N4C3=NC3=CC=CC=C3C4=O)N=C2O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H22N4O5/c32-16-11-9-15(10-12-16)13-20-23(33)29-21(24(34)28-20)14-27(36)18-6-2-4-8-22(18)31-25(35)17-5-1-3-7-19(17)30-26(27)31/h1-12,20-21,32,36H,13-14H2,(H,28,34)(H,29,33)/t20-,21-,27-/m0/s1

> <INCHI_KEY>
VPFCTRSBEVRCRU-IZVMNLJQSA-N

> <FORMULA>
C27H22N4O5

> <MOLECULAR_WEIGHT>
482.496

> <EXACT_MASS>
482.159019824

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
48.984220708459816

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(12S)-12-{[(2S,5S)-3,6-dihydroxy-5-[(4-hydroxyphenyl)methyl]-2,5-dihydropyrazin-2-yl]methyl}-12-hydroxy-6H,12H-indolo[2,1-b]quinazolin-6-one

> <JCHEM_LOGP>
1.707126814558546

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
4.793854053436093

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8369338936528132

> <JCHEM_PKA_STRONGEST_BASIC>
3.7644378693151253

> <JCHEM_POLAR_SURFACE_AREA>
138.31

> <JCHEM_REFRACTIVITY>
132.4169

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(12S)-12-{[(2S,5S)-3,6-dihydroxy-5-[(4-hydroxyphenyl)methyl]-2,5-dihydropyrazin-2-yl]methyl}-12-hydroxyindolo[2,1-b]quinazolin-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  O   UNK     0       5.249  -1.724   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.552  -0.214   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.012   0.278   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.167  -0.740   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.627  -0.248   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.930   1.262   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.774   2.280   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.315   1.788   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       6.159   2.806   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       4.700   2.314   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       4.397   0.804   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       2.867   0.626   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.976  -0.630   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.442  -0.486   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.200   0.914   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.692   2.170   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.225   2.026   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.358   3.069   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.452   4.314   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.954   4.489   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.022   5.715   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       3.618   7.135   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       2.687   8.361   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.283   9.781   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.159   8.167   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.227   9.393   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.301   9.200   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.897   7.780   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.424   7.586   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.356   8.812   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -5.884   8.618   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -3.760  10.232   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.232  10.426   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0       0.563   6.747   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0       1.495   5.521   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       0.899   4.101   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   18                                                  
CONECT   11   10    2   12                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17   10   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   35                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   34                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   33                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   27                                                       
CONECT   34   25   35                                                       
CONECT   35   34   21   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₂₂N₄O₅

Average Mass

482.4960 Da

Monoisotopic Mass

482.15902 Da

IUPAC Name

(12S)-12-{[(2S,5S)-3,6-dihydroxy-5-[(4-hydroxyphenyl)methyl]-2,5-dihydropyrazin-2-yl]methyl}-12-hydroxy-6H,12H-indolo[2,1-b]quinazolin-6-one

Traditional Name

(12S)-12-{[(2S,5S)-3,6-dihydroxy-5-[(4-hydroxyphenyl)methyl]-2,5-dihydropyrazin-2-yl]methyl}-12-hydroxyindolo[2,1-b]quinazolin-6-one

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C[C@@H]2N=C(O)[C@H](C[C@]3(O)C4=CC=CC=C4N4C3=NC3=CC=CC=C3C4=O)N=C2O)C=C1

InChI Identifier

InChI=1S/C27H22N4O5/c32-16-11-9-15(10-12-16)13-20-23(33)29-21(24(34)28-20)14-27(36)18-6-2-4-8-22(18)31-25(35)17-5-1-3-7-19(17)30-26(27)31/h1-12,20-21,32,36H,13-14H2,(H,28,34)(H,29,33)/t20-,21-,27-/m0/s1

InChI Key

VPFCTRSBEVRCRU-IZVMNLJQSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoloquinazolines. These are polycyclic aromatic compounds containing an indole fused to a quinazoline. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Quinazoline is a heterocyclic compound consisting of two fused six-membered simple aromatic rings, a benzene ring and a pyrimidine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Benzodiazines

Direct Parent

Indoloquinazolines

Alternative Parents

Substituents

Indoloquinazoline
Indole or derivatives
Indole
1-hydroxy-2-unsubstituted benzenoid
Pyrimidone
Phenol
Benzenoid
Pyrimidine
Monocyclic benzene moiety
Heteroaromatic compound
Cyclic carboximidic acid
Tertiary alcohol
Lactam
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen 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	1.71	ChemAxon
pKa (Strongest Acidic)	1.84	ChemAxon
pKa (Strongest Basic)	3.76	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	138.31 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	132.42 m³·mol⁻¹	ChemAxon
Polarizability	48.98 Å³	ChemAxon
Number of Rings	6	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78441569

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

122386142

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (6s)-6-{[(2s,5s)-3,6-dihydroxy-5-[(4-hydroxyphenyl)methyl]-2,5-dihydropyrazin-2-yl]methyl}-6-hydroxyindolo[2,1-b]quinazolin-12-one (NP0285580)

MOL for NP0285580 ((6s)-6-{[(2s,5s)-3,6-dihydroxy-5-[(4-hydroxyphenyl)methyl]-2,5-dihydropyrazin-2-yl]methyl}-6-hydroxyindolo[2,1-b]quinazolin-12-one)

3D MOL for NP0285580 ((6s)-6-{[(2s,5s)-3,6-dihydroxy-5-[(4-hydroxyphenyl)methyl]-2,5-dihydropyrazin-2-yl]methyl}-6-hydroxyindolo[2,1-b]quinazolin-12-one)

3D SDF for NP0285580 ((6s)-6-{[(2s,5s)-3,6-dihydroxy-5-[(4-hydroxyphenyl)methyl]-2,5-dihydropyrazin-2-yl]methyl}-6-hydroxyindolo[2,1-b]quinazolin-12-one)

3D-SDF for NP0285580 ((6s)-6-{[(2s,5s)-3,6-dihydroxy-5-[(4-hydroxyphenyl)methyl]-2,5-dihydropyrazin-2-yl]methyl}-6-hydroxyindolo[2,1-b]quinazolin-12-one)

PDB for NP0285580 ((6s)-6-{[(2s,5s)-3,6-dihydroxy-5-[(4-hydroxyphenyl)methyl]-2,5-dihydropyrazin-2-yl]methyl}-6-hydroxyindolo[2,1-b]quinazolin-12-one)

3D PDB for NP0285580 ((6s)-6-{[(2s,5s)-3,6-dihydroxy-5-[(4-hydroxyphenyl)methyl]-2,5-dihydropyrazin-2-yl]methyl}-6-hydroxyindolo[2,1-b]quinazolin-12-one)

SMILES for NP0285580 ((6s)-6-{[(2s,5s)-3,6-dihydroxy-5-[(4-hydroxyphenyl)methyl]-2,5-dihydropyrazin-2-yl]methyl}-6-hydroxyindolo[2,1-b]quinazolin-12-one)

INCHI for NP0285580 ((6s)-6-{[(2s,5s)-3,6-dihydroxy-5-[(4-hydroxyphenyl)methyl]-2,5-dihydropyrazin-2-yl]methyl}-6-hydroxyindolo[2,1-b]quinazolin-12-one)

Structure for NP0285580 ((6s)-6-{[(2s,5s)-3,6-dihydroxy-5-[(4-hydroxyphenyl)methyl]-2,5-dihydropyrazin-2-yl]methyl}-6-hydroxyindolo[2,1-b]quinazolin-12-one)

3D Structure for NP0285580 ((6s)-6-{[(2s,5s)-3,6-dihydroxy-5-[(4-hydroxyphenyl)methyl]-2,5-dihydropyrazin-2-yl]methyl}-6-hydroxyindolo[2,1-b]quinazolin-12-one)