NP-MRD: Showing NP-Card for 3-hydroxy-2H-pyrrolo[2,3-b]indolo[5,5a,6-b,a]quinazoline-9(8H),7'-dione (NP0036795)

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Record Information

Version

2.0

Created at

2021-06-20 19:52:30 UTC

Updated at

2021-06-30 00:08:38 UTC

NP-MRD ID

NP0036795

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-hydroxy-2H-pyrrolo[2,3-b]indolo[5,5a,6-b,a]quinazoline-9(8H),7'-dione

Provided By

JEOL Database JEOL Logo

Description

(+)-Cruciferane belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. 3-hydroxy-2H-pyrrolo[2,3-b]indolo[5,5a,6-b,a]quinazoline-9(8H),7'-dione is found in Isatis indigotica. 3-hydroxy-2H-pyrrolo[2,3-b]indolo[5,5a,6-b,a]quinazoline-9(8H),7'-dione was first documented in 2012 (Chen, M., et al.). Based on a literature review a small amount of articles have been published on (+)-Cruciferane.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121523D          

 34 38  0  0  0  0            999 V2000
    3.7317    0.8493    0.2971 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6144    0.5871    0.7167 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2031   -0.7933    1.2037 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7707   -0.6461    1.7165 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7138   -0.9129    3.1186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3321   -1.3745    0.9889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5478   -2.7422    0.9119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6462   -3.1959    0.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5043   -2.2892   -0.4683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2806   -0.9121   -0.3917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2007   -0.4746    0.3488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7377    0.8271    0.5263 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1251    1.9938   -0.0929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2063    2.1876   -0.6350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0335    3.0322   -0.1675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3070    4.2825   -0.7283 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7408    5.1713   -0.9717 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0576    4.8025   -0.6830 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3412    3.5505   -0.1293 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2989    2.6712    0.1576 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5122    1.4145    0.7516 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4036    0.8143    1.4004 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8960   -1.1053    1.9916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2726   -1.4858    0.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1649   -1.2816    3.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1157   -3.4476    1.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8397   -4.2639    0.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3497   -2.6636   -1.0420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9389   -0.2172   -0.9036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3238    4.5512   -1.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5349    6.1439   -1.4133 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8713    5.4933   -0.8942 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3737    3.2913    0.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1688    1.3883    2.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 12  1  0  0  0  0
  6 11  2  0  0  0  0
  9 10  2  0  0  0  0
 12 13  1  0  0  0  0
 13 15  1  0  0  0  0
 20 21  1  0  0  0  0
 11 12  1  0  0  0  0
  4  6  1  0  0  0  0
 20 15  2  0  0  0  0
  4 22  1  0  0  0  0
 15 16  1  0  0  0  0
 10 11  1  0  0  0  0
 16 17  2  0  0  0  0
  8  9  1  0  0  0  0
 17 18  1  0  0  0  0
  6  7  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 22 21  1  0  0  0  0
  7  8  2  0  0  0  0
 13 14  2  0  0  0  0
 21  2  1  0  0  0  0
  2  1  2  0  0  0  0
  2  3  1  0  0  0  0
  4  5  1  0  0  0  0
  3  4  1  0  0  0  0
 22 34  1  0  0  0  0
  8 27  1  0  0  0  0
  9 28  1  0  0  0  0
 10 29  1  0  0  0  0
  7 26  1  0  0  0  0
  3 23  1  0  0  0  0
  3 24  1  0  0  0  0
 16 30  1  0  0  0  0
 17 31  1  0  0  0  0
 18 32  1  0  0  0  0
 19 33  1  0  0  0  0
  5 25  1  0  0  0  0
M  END

     RDKit          3D

 34 38  0  0  0  0  0  0  0  0999 V2000
    3.7317    0.8493    0.2971 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6144    0.5871    0.7167 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2031   -0.7933    1.2037 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7707   -0.6461    1.7165 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7138   -0.9129    3.1186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3321   -1.3745    0.9889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5478   -2.7422    0.9119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6462   -3.1959    0.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5043   -2.2892   -0.4683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2806   -0.9121   -0.3917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2007   -0.4746    0.3488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7377    0.8271    0.5263 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1251    1.9938   -0.0929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2063    2.1876   -0.6350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0335    3.0322   -0.1675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3070    4.2825   -0.7283 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7408    5.1713   -0.9717 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0576    4.8025   -0.6830 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3412    3.5505   -0.1293 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2989    2.6712    0.1576 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5122    1.4145    0.7516 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4036    0.8143    1.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8960   -1.1053    1.9916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2726   -1.4858    0.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1649   -1.2816    3.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1157   -3.4476    1.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8397   -4.2639    0.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3497   -2.6636   -1.0420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9389   -0.2172   -0.9036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3238    4.5512   -1.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5349    6.1439   -1.4133 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8713    5.4933   -0.8942 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3737    3.2913    0.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1688    1.3883    2.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 12  1  0
  6 11  2  0
  9 10  2  0
 12 13  1  0
 13 15  1  0
 20 21  1  0
 11 12  1  0
  4  6  1  0
 20 15  2  0
  4 22  1  0
 15 16  1  0
 10 11  1  0
 16 17  2  0
  8  9  1  0
 17 18  1  0
  6  7  1  0
 18 19  2  0
 19 20  1  0
 22 21  1  0
  7  8  2  0
 13 14  2  0
 21  2  1  0
  2  1  2  0
  2  3  1  0
  4  5  1  0
  3  4  1  0
 22 34  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
  7 26  1  0
  3 23  1  0
  3 24  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
  5 25  1  0
M  END


  Mrv1652306202121523D          

 34 38  0  0  0  0            999 V2000
    3.7317    0.8493    0.2971 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6144    0.5871    0.7167 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2031   -0.7933    1.2037 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7707   -0.6461    1.7165 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7138   -0.9129    3.1186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3321   -1.3745    0.9889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5478   -2.7422    0.9119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6462   -3.1959    0.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5043   -2.2892   -0.4683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2806   -0.9121   -0.3917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2007   -0.4746    0.3488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7377    0.8271    0.5263 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1251    1.9938   -0.0929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2063    2.1876   -0.6350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0335    3.0322   -0.1675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3070    4.2825   -0.7283 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7408    5.1713   -0.9717 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0576    4.8025   -0.6830 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3412    3.5505   -0.1293 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2989    2.6712    0.1576 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5122    1.4145    0.7516 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4036    0.8143    1.4004 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8960   -1.1053    1.9916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2726   -1.4858    0.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1649   -1.2816    3.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1157   -3.4476    1.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8397   -4.2639    0.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3497   -2.6636   -1.0420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9389   -0.2172   -0.9036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3238    4.5512   -1.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5349    6.1439   -1.4133 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8713    5.4933   -0.8942 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3737    3.2913    0.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1688    1.3883    2.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 12  1  0  0  0  0
  6 11  2  0  0  0  0
  9 10  2  0  0  0  0
 12 13  1  0  0  0  0
 13 15  1  0  0  0  0
 20 21  1  0  0  0  0
 11 12  1  0  0  0  0
  4  6  1  0  0  0  0
 20 15  2  0  0  0  0
  4 22  1  0  0  0  0
 15 16  1  0  0  0  0
 10 11  1  0  0  0  0
 16 17  2  0  0  0  0
  8  9  1  0  0  0  0
 17 18  1  0  0  0  0
  6  7  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 22 21  1  0  0  0  0
  7  8  2  0  0  0  0
 13 14  2  0  0  0  0
 21  2  1  0  0  0  0
  2  1  2  0  0  0  0
  2  3  1  0  0  0  0
  4  5  1  0  0  0  0
  3  4  1  0  0  0  0
 22 34  1  0  0  0  0
  8 27  1  0  0  0  0
  9 28  1  0  0  0  0
 10 29  1  0  0  0  0
  7 26  1  0  0  0  0
  3 23  1  0  0  0  0
  3 24  1  0  0  0  0
 16 30  1  0  0  0  0
 17 31  1  0  0  0  0
 18 32  1  0  0  0  0
 19 33  1  0  0  0  0
  5 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0036795

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]12C3=C(C([H])=C([H])C([H])=C3[H])N3C(=O)C4=C(C([H])=C([H])C([H])=C4[H])N(C(=O)C1([H])[H])[C@]23[H]

> <INCHI_IDENTIFIER>
InChI=1S/C17H12N2O3/c20-14-9-17(22)11-6-2-4-8-13(11)19-15(21)10-5-1-3-7-12(10)18(14)16(17)19/h1-8,16,22H,9H2/t16-,17-/m0/s1

> <INCHI_KEY>
DMWBWCODLSCGLM-IRXDYDNUSA-N

> <FORMULA>
C17H12N2O3

> <MOLECULAR_WEIGHT>
292.294

> <EXACT_MASS>
292.084792254

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
29.567177956435533

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(8S,19S)-8-hydroxy-1,11-diazapentacyclo[9.7.1.0^{2,7}.0^{8,19}.0^{12,17}]nonadeca-2(7),3,5,12(17),13,15-hexaene-10,18-dione

> <ALOGPS_LOGP>
0.77

> <JCHEM_LOGP>
1.1683290853333332

> <ALOGPS_LOGS>
-1.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.659542810230498

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.701315544957701

> <JCHEM_PKA_STRONGEST_BASIC>
-3.240996799502321

> <JCHEM_POLAR_SURFACE_AREA>
60.85

> <JCHEM_REFRACTIVITY>
78.0019

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.40e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(8S,19S)-8-hydroxy-1,11-diazapentacyclo[9.7.1.0^{2,7}.0^{8,19}.0^{12,17}]nonadeca-2(7),3,5,12(17),13,15-hexaene-10,18-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 34 38  0  0  0  0  0  0  0  0999 V2000
    3.7317    0.8493    0.2971 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6144    0.5871    0.7167 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2031   -0.7933    1.2037 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7707   -0.6461    1.7165 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7138   -0.9129    3.1186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3321   -1.3745    0.9889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5478   -2.7422    0.9119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6462   -3.1959    0.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5043   -2.2892   -0.4683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2806   -0.9121   -0.3917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2007   -0.4746    0.3488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7377    0.8271    0.5263 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1251    1.9938   -0.0929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2063    2.1876   -0.6350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0335    3.0322   -0.1675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3070    4.2825   -0.7283 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7408    5.1713   -0.9717 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0576    4.8025   -0.6830 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3412    3.5505   -0.1293 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2989    2.6712    0.1576 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5122    1.4145    0.7516 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4036    0.8143    1.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8960   -1.1053    1.9916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2726   -1.4858    0.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1649   -1.2816    3.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1157   -3.4476    1.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8397   -4.2639    0.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3497   -2.6636   -1.0420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9389   -0.2172   -0.9036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3238    4.5512   -1.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5349    6.1439   -1.4133 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8713    5.4933   -0.8942 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3737    3.2913    0.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1688    1.3883    2.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 12  1  0
  6 11  2  0
  9 10  2  0
 12 13  1  0
 13 15  1  0
 20 21  1  0
 11 12  1  0
  4  6  1  0
 20 15  2  0
  4 22  1  0
 15 16  1  0
 10 11  1  0
 16 17  2  0
  8  9  1  0
 17 18  1  0
  6  7  1  0
 18 19  2  0
 19 20  1  0
 22 21  1  0
  7  8  2  0
 13 14  2  0
 21  2  1  0
  2  1  2  0
  2  3  1  0
  4  5  1  0
  3  4  1  0
 22 34  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
  7 26  1  0
  3 23  1  0
  3 24  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
  5 25  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  O   UNK     0       3.732   0.849   0.297  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.614   0.587   0.717  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.203  -0.793   1.204  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.771  -0.646   1.716  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.714  -0.913   3.119  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.332  -1.375   0.989  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.548  -2.742   0.912  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.646  -3.196   0.178  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.504  -2.289  -0.468  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.281  -0.912  -0.392  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.201  -0.475   0.349  0.00  0.00           C+0
HETATM   12  N   UNK     0      -0.738   0.827   0.526  0.00  0.00           N+0
HETATM   13  C   UNK     0      -1.125   1.994  -0.093  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.206   2.188  -0.635  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.034   3.032  -0.168  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.307   4.282  -0.728  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.741   5.171  -0.972  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.058   4.803  -0.683  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.341   3.551  -0.129  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.299   2.671   0.158  0.00  0.00           C+0
HETATM   21  N   UNK     0       1.512   1.415   0.752  0.00  0.00           N+0
HETATM   22  C   UNK     0       0.404   0.814   1.400  0.00  0.00           C+0
HETATM   23  H   UNK     0       2.896  -1.105   1.992  0.00  0.00           H+0
HETATM   24  H   UNK     0       2.273  -1.486   0.358  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.165  -1.282   3.324  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.116  -3.448   1.404  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.840  -4.264   0.098  0.00  0.00           H+0
HETATM   28  H   UNK     0      -3.350  -2.664  -1.042  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.939  -0.217  -0.904  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.324   4.551  -1.006  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.535   6.144  -1.413  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.871   5.493  -0.894  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.374   3.291   0.091  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.169   1.388   2.308  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2   21    1    3                                                  
CONECT    3    2    4   23   24                                             
CONECT    4    6   22    5    3                                             
CONECT    5    4   25                                                       
CONECT    6   11    4    7                                                  
CONECT    7    6    8   26                                                  
CONECT    8    9    7   27                                                  
CONECT    9   10    8   28                                                  
CONECT   10    9   11   29                                                  
CONECT   11    6   12   10                                                  
CONECT   12   22   13   11                                                  
CONECT   13   12   15   14                                                  
CONECT   14   13                                                            
CONECT   15   13   20   16                                                  
CONECT   16   15   17   30                                                  
CONECT   17   16   18   31                                                  
CONECT   18   17   19   32                                                  
CONECT   19   18   20   33                                                  
CONECT   20   21   15   19                                                  
CONECT   21   20   22    2                                                  
CONECT   22   12    4   21   34                                             
CONECT   23    3                                                            
CONECT   24    3                                                            
CONECT   25    5                                                            
CONECT   26    7                                                            
CONECT   27    8                                                            
CONECT   28    9                                                            
CONECT   29   10                                                            
CONECT   30   16                                                            
CONECT   31   17                                                            
CONECT   32   18                                                            
CONECT   33   19                                                            
CONECT   34   22                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

RDKit          3D

34 38  0  0  0  0  0  0  0  0999 V2000
    3.7317    0.8493    0.2971 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6144    0.5871    0.7167 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2031   -0.7933    1.2037 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7707   -0.6461    1.7165 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7138   -0.9129    3.1186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3321   -1.3745    0.9889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5478   -2.7422    0.9119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6462   -3.1959    0.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5043   -2.2892   -0.4683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2806   -0.9121   -0.3917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2007   -0.4746    0.3488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7377    0.8271    0.5263 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1251    1.9938   -0.0929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2063    2.1876   -0.6350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0335    3.0322   -0.1675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3070    4.2825   -0.7283 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7408    5.1713   -0.9717 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0576    4.8025   -0.6830 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3412    3.5505   -0.1293 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2989    2.6712    0.1576 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5122    1.4145    0.7516 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4036    0.8143    1.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8960   -1.1053    1.9916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2726   -1.4858    0.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1649   -1.2816    3.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1157   -3.4476    1.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8397   -4.2639    0.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3497   -2.6636   -1.0420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9389   -0.2172   -0.9036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3238    4.5512   -1.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5349    6.1439   -1.4133 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8713    5.4933   -0.8942 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3737    3.2913    0.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1688    1.3883    2.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 12  1  0
  6 11  2  0
  9 10  2  0
 12 13  1  0
 13 15  1  0
 20 21  1  0
 11 12  1  0
  4  6  1  0
 20 15  2  0
  4 22  1  0
 15 16  1  0
 10 11  1  0
 16 17  2  0
  8  9  1  0
 17 18  1  0
  6  7  1  0
 18 19  2  0
 19 20  1  0
 22 21  1  0
  7  8  2  0
 13 14  2  0
 21  2  1  0
  2  1  2  0
  2  3  1  0
  4  5  1  0
  3  4  1  0
 22 34  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
  7 26  1  0
  3 23  1  0
  3 24  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
  5 25  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₂N₂O₃

Average Mass

292.2940 Da

Monoisotopic Mass

292.08479 Da

IUPAC Name

(8S,19S)-8-hydroxy-1,11-diazapentacyclo[9.7.1.0^{2,7}.0^{8,19}.0^{12,17}]nonadeca-2(7),3,5,12(17),13,15-hexaene-10,18-dione

Traditional Name

(8S,19S)-8-hydroxy-1,11-diazapentacyclo[9.7.1.0^{2,7}.0^{8,19}.0^{12,17}]nonadeca-2(7),3,5,12(17),13,15-hexaene-10,18-dione

CAS Registry Number

Not Available

SMILES

[H]O[C@]12C3=C(C([H])=C([H])C([H])=C3[H])N3C(=O)C4=C(C([H])=C([H])C([H])=C4[H])N(C(=O)C1([H])[H])[C@]23[H]

InChI Identifier

InChI=1S/C17H12N2O3/c20-14-9-17(22)11-6-2-4-8-13(11)19-15(21)10-5-1-3-7-12(10)18(14)16(17)19/h1-8,16,22H,9H2/t16-,17-/m0/s1

InChI Key

DMWBWCODLSCGLM-IRXDYDNUSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Isatis tinctoria	JEOL database	Chen, M., et al, J. Nat. Prod. 75, 1167 (2012)

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyrroloindoles

Direct Parent

Pyrroloindoles

Alternative Parents

Substituents

Pyrroloindole
Quinazoline
Indole
Pyrrolidone
2-pyrrolidone
Benzenoid
Pyrrole
Pyrrolidine
Tertiary alcohol
Tertiary carboxylic acid amide
Vinylogous amide
Lactam
Carboxamide group
Azacycle
Carboxylic acid derivative
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.77	ALOGPS
logP	1.17	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	12.7	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	60.85 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	78 m³·mol⁻¹	ChemAxon
Polarizability	29.57 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

28507859

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

60156157

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chen, M., et al. (2012). Chen, M., et al, J. Nat. Prod. 75, 1167 (2012). J. Nat. Prod..

Showing NP-Card for 3-hydroxy-2H-pyrrolo[2,3-b]indolo[5,5a,6-b,a]quinazoline-9(8H),7'-dione (NP0036795)

MOL for NP0036795 (3-hydroxy-2H-pyrrolo[2,3-b]indolo[5,5a,6-b,a]quinazoline-9(8H),7'-dione)

3D MOL for NP0036795 (3-hydroxy-2H-pyrrolo[2,3-b]indolo[5,5a,6-b,a]quinazoline-9(8H),7'-dione)

3D SDF for NP0036795 (3-hydroxy-2H-pyrrolo[2,3-b]indolo[5,5a,6-b,a]quinazoline-9(8H),7'-dione)

3D-SDF for NP0036795 (3-hydroxy-2H-pyrrolo[2,3-b]indolo[5,5a,6-b,a]quinazoline-9(8H),7'-dione)

PDB for NP0036795 (3-hydroxy-2H-pyrrolo[2,3-b]indolo[5,5a,6-b,a]quinazoline-9(8H),7'-dione)

3D PDB for NP0036795 (3-hydroxy-2H-pyrrolo[2,3-b]indolo[5,5a,6-b,a]quinazoline-9(8H),7'-dione)

SMILES for NP0036795 (3-hydroxy-2H-pyrrolo[2,3-b]indolo[5,5a,6-b,a]quinazoline-9(8H),7'-dione)

INCHI for NP0036795 (3-hydroxy-2H-pyrrolo[2,3-b]indolo[5,5a,6-b,a]quinazoline-9(8H),7'-dione)

Structure for NP0036795 (3-hydroxy-2H-pyrrolo[2,3-b]indolo[5,5a,6-b,a]quinazoline-9(8H),7'-dione)

3D Structure for NP0036795 (3-hydroxy-2H-pyrrolo[2,3-b]indolo[5,5a,6-b,a]quinazoline-9(8H),7'-dione)