NP-MRD: Showing NP-Card for (1s,9r,19r,22r)-5-bromo-22-chloro-17-hydroxy-20,20-dimethyl-2,12,16,18-tetraazahexacyclo[10.10.0.0¹,⁹.0²,¹⁹.0³,⁸.0¹⁵,¹⁹]docosa-3,5,7,13,15,17-hexaen-11-one (NP0325127)

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Record Information

Version

1.0

Created at

2022-09-12 05:38:54 UTC

Updated at

2022-09-12 05:38:54 UTC

NP-MRD ID

NP0325127

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,9r,19r,22r)-5-bromo-22-chloro-17-hydroxy-20,20-dimethyl-2,12,16,18-tetraazahexacyclo[10.10.0.0¹,⁹.0²,¹⁹.0³,⁸.0¹⁵,¹⁹]docosa-3,5,7,13,15,17-hexaen-11-one

Description

(1S,9R,19R,22R)-5-bromo-22-chloro-17-hydroxy-20,20-dimethyl-2,12,16,18-tetraazahexacyclo[10.10.0.0¹,⁹.0²,¹⁹.0³,⁸.0¹⁵,¹⁹]Docosa-3(8),4,6,13,15,17-hexaen-11-one 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. (1s,9r,19r,22r)-5-bromo-22-chloro-17-hydroxy-20,20-dimethyl-2,12,16,18-tetraazahexacyclo[10.10.0.0¹,⁹.0²,¹⁹.0³,⁸.0¹⁵,¹⁹]docosa-3,5,7,13,15,17-hexaen-11-one is found in Securiflustra securifrons. Based on a literature review very few articles have been published on (1S,9R,19R,22R)-5-bromo-22-chloro-17-hydroxy-20,20-dimethyl-2,12,16,18-tetraazahexacyclo[10.10.0.0¹,⁹.0²,¹⁹.0³,⁸.0¹⁵,¹⁹]Docosa-3(8),4,6,13,15,17-hexaen-11-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122207382D          

 28 33  0  0  1  0            999 V2000
    2.5410   -1.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2266   -1.0437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3172   -1.8637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3546   -0.5660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8393    0.2051    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4738    0.9447    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4441   -0.3253    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6716   -0.0356    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7084    0.7886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5037    1.0082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7933    1.7807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9583    0.3198    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7833    0.3200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2979   -0.3248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1145   -1.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6848   -1.7254    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2940   -2.4520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6521   -3.1952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4822   -2.3048    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3713   -1.4873    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6279   -1.1296    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9198   -1.5529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7605   -2.3624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9799   -2.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8207   -3.4387    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.3585   -2.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5177   -1.2771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2983   -1.0103    0.0000 C   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  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
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  1  0  0  0
  7 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 22 28  1  0  0  0  0
  8 28  1  0  0  0  0
M  END

     RDKit          3D

 46 51  0  0  0  0  0  0  0  0999 V2000
   -2.3958    0.4399   -2.1297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3466    1.1336   -1.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9445    2.5117   -0.9599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1151    1.3586   -2.0592 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9628    0.3622   -1.9974 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5200    1.1991   -2.1906 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.9941   -0.5029   -0.7547 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3633   -0.6484   -0.1791 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7753   -2.1052   -0.2506 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7811   -2.6732   -1.1749 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9376   -3.6721   -1.9009 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6075   -1.8796   -1.0931 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7259   -2.3645   -1.3165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9058   -1.9474   -0.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0620   -0.8067    0.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9538   -0.6962    0.9538 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7843    0.5389    1.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5677    1.0154    2.6951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7819    1.1653    1.1124 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1867    0.4107    0.0306 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1889    0.0772    0.2846 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9814    0.2221    1.4416 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6782    0.7031    2.7309 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6067    0.7669    3.7383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1553    1.4286    5.4829 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.8873    0.3461    3.4862 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2064   -0.1313    2.2213 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2593   -0.1893    1.2170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9819   -0.2725   -2.8572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9098    1.2278   -2.7560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2288    0.0225   -1.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0300    2.5274   -1.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6459    2.8203    0.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5280    3.2919   -1.6401 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2983    2.3830   -1.8134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4144    1.4769   -3.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8921   -0.3360   -2.8825 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1618   -0.1069   -0.7375 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8205   -2.2446   -0.6018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6456   -2.5186    0.7885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7584   -3.2328   -1.9664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8077   -2.4392   -1.1673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1777    0.3799    3.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3149    1.0457    2.9714 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6398    0.3852    4.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2044   -0.4725    1.9819 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 20 19  1  1
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 26 27  1  0
 27 28  2  0
 20  2  1  0
 28 22  1  0
  7 12  1  6
 20 15  1  0
 21  7  1  0
 28  8  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  6
  8 38  1  6
  9 39  1  0
  9 40  1  0
 13 41  1  0
 14 42  1  0
 18 43  1  0
 23 44  1  0
 26 45  1  0
 27 46  1  0
M  END


  Mrv1652309122207382D          

 28 33  0  0  1  0            999 V2000
    2.5410   -1.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2266   -1.0437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3172   -1.8637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3546   -0.5660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8393    0.2051    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4738    0.9447    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4441   -0.3253    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6716   -0.0356    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7084    0.7886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5037    1.0082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7933    1.7807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9583    0.3198    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7833    0.3200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2979   -0.3248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1145   -1.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6848   -1.7254    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2940   -2.4520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6521   -3.1952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4822   -2.3048    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3713   -1.4873    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6279   -1.1296    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9198   -1.5529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7605   -2.3624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9799   -2.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8207   -3.4387    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.3585   -2.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5177   -1.2771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2983   -1.0103    0.0000 C   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  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
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  1  0  0  0
  7 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 22 28  1  0  0  0  0
  8 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0325127

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)C[C@@H](Cl)[C@]23[C@@H]4CC(=O)N2C=CC2=NC(O)=N[C@]12N3C1=CC(Br)=CC=C41

> <INCHI_IDENTIFIER>
InChI=1S/C20H18BrClN4O2/c1-18(2)9-14(22)19-12-8-16(27)25(19)6-5-15-20(18,24-17(28)23-15)26(19)13-7-10(21)3-4-11(12)13/h3-7,12,14H,8-9H2,1-2H3,(H,24,28)/t12-,14-,19-,20-/m1/s1

> <INCHI_KEY>
KYMPMBARXJWTMI-ANFIAMTQSA-N

> <FORMULA>
C20H18BrClN4O2

> <MOLECULAR_WEIGHT>
461.74

> <EXACT_MASS>
460.030167

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
41.564076666987546

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,9R,19R,22R)-5-bromo-22-chloro-17-hydroxy-20,20-dimethyl-2,12,16,18-tetraazahexacyclo[10.10.0.0^{1,9}.0^{2,19}.0^{3,8}.0^{15,19}]docosa-3,5,7,13,15,17-hexaen-11-one

> <JCHEM_LOGP>
5.146984480333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5310869536008234

> <JCHEM_PKA_STRONGEST_BASIC>
0.15160452671814417

> <JCHEM_POLAR_SURFACE_AREA>
68.5

> <JCHEM_REFRACTIVITY>
108.8725

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,9R,19R,22R)-5-bromo-22-chloro-17-hydroxy-20,20-dimethyl-2,12,16,18-tetraazahexacyclo[10.10.0.0^{1,9}.0^{2,19}.0^{3,8}.0^{15,19}]docosa-3,5,7,13,15,17-hexaen-11-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       4.743  -2.805   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.023  -1.948   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.192  -3.479   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.395  -1.057   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.300   0.383   0.000  0.00  0.00           C+0
HETATM    6 Cl   UNK     0       4.618   1.764   0.000  0.00  0.00          Cl+0
HETATM    7  C   UNK     0       6.429  -0.607   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.987  -0.066   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.056   1.472   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.540   1.882   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.081   3.324   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       7.389   0.597   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       8.929   0.597   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.889  -0.606   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.547  -2.108   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      10.612  -3.221   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       9.882  -4.577   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.551  -5.964   0.000  0.00  0.00           O+0
HETATM   19  N   UNK     0       8.367  -4.302   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       8.160  -2.776   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       6.772  -2.109   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       5.450  -2.899   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.153  -4.410   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.696  -4.908   0.000  0.00  0.00           C+0
HETATM   25 Br   UNK     0       3.399  -6.419   0.000  0.00  0.00          Br+0
HETATM   26  C   UNK     0       2.536  -3.895   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.833  -2.384   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.290  -1.886   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   20                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   12   21                                             
CONECT    8    7    9   28                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    7   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   15    2   21                                             
CONECT   21   20    7   22                                                  
CONECT   22   21   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   22    8                                                  
MASTER        0    0    0    0    0    0    0    0   28    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₈BrClN₄O₂

Average Mass

461.7400 Da

Monoisotopic Mass

460.03017 Da

IUPAC Name

(1S,9R,19R,22R)-5-bromo-22-chloro-17-hydroxy-20,20-dimethyl-2,12,16,18-tetraazahexacyclo[10.10.0.0^{1,9}.0^{2,19}.0^{3,8}.0^{15,19}]docosa-3,5,7,13,15,17-hexaen-11-one

Traditional Name

(1S,9R,19R,22R)-5-bromo-22-chloro-17-hydroxy-20,20-dimethyl-2,12,16,18-tetraazahexacyclo[10.10.0.0^{1,9}.0^{2,19}.0^{3,8}.0^{15,19}]docosa-3,5,7,13,15,17-hexaen-11-one

CAS Registry Number

Not Available

SMILES

CC1(C)C[C@@H](Cl)[C@]23[C@@H]4CC(=O)N2C=CC2=NC(O)=N[C@]12N3C1=CC(Br)=CC=C41

InChI Identifier

InChI=1S/C20H18BrClN4O2/c1-18(2)9-14(22)19-12-8-16(27)25(19)6-5-15-20(18,24-17(28)23-15)26(19)13-7-10(21)3-4-11(12)13/h3-7,12,14H,8-9H2,1-2H3,(H,24,28)/t12-,14-,19-,20-/m1/s1

InChI Key

KYMPMBARXJWTMI-ANFIAMTQSA-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

Species Name	Source	Reference
Securiflustra securifrons	LOTUS Database	35616633

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
Azaspirodecane
Indole
Dialkylarylamine
Aryl bromide
Aryl halide
Piperidine
Benzenoid
2-pyrrolidone
Pyrrolidone
Imidazole
Tertiary carboxylic acid amide
Pyrrolidine
Pyrrole
Carboxamide group
Lactam
Carboxylic acid derivative
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organobromide
Organohalogen compound
Alkyl halide
Hydrocarbon derivative
Alkyl chloride
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
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	5.15	ChemAxon
pKa (Strongest Acidic)	3.53	ChemAxon
pKa (Strongest Basic)	0.15	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	68.5 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	108.87 m³·mol⁻¹	ChemAxon
Polarizability	41.56 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163066057

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,9r,19r,22r)-5-bromo-22-chloro-17-hydroxy-20,20-dimethyl-2,12,16,18-tetraazahexacyclo[10.10.0.0¹,⁹.0²,¹⁹.0³,⁸.0¹⁵,¹⁹]docosa-3,5,7,13,15,17-hexaen-11-one (NP0325127)

MOL for NP0325127 ((1s,9r,19r,22r)-5-bromo-22-chloro-17-hydroxy-20,20-dimethyl-2,12,16,18-tetraazahexacyclo[10.10.0.0¹,⁹.0²,¹⁹.0³,⁸.0¹⁵,¹⁹]docosa-3,5,7,13,15,17-hexaen-11-one)

3D MOL for NP0325127 ((1s,9r,19r,22r)-5-bromo-22-chloro-17-hydroxy-20,20-dimethyl-2,12,16,18-tetraazahexacyclo[10.10.0.0¹,⁹.0²,¹⁹.0³,⁸.0¹⁵,¹⁹]docosa-3,5,7,13,15,17-hexaen-11-one)

3D SDF for NP0325127 ((1s,9r,19r,22r)-5-bromo-22-chloro-17-hydroxy-20,20-dimethyl-2,12,16,18-tetraazahexacyclo[10.10.0.0¹,⁹.0²,¹⁹.0³,⁸.0¹⁵,¹⁹]docosa-3,5,7,13,15,17-hexaen-11-one)

3D-SDF for NP0325127 ((1s,9r,19r,22r)-5-bromo-22-chloro-17-hydroxy-20,20-dimethyl-2,12,16,18-tetraazahexacyclo[10.10.0.0¹,⁹.0²,¹⁹.0³,⁸.0¹⁵,¹⁹]docosa-3,5,7,13,15,17-hexaen-11-one)

PDB for NP0325127 ((1s,9r,19r,22r)-5-bromo-22-chloro-17-hydroxy-20,20-dimethyl-2,12,16,18-tetraazahexacyclo[10.10.0.0¹,⁹.0²,¹⁹.0³,⁸.0¹⁵,¹⁹]docosa-3,5,7,13,15,17-hexaen-11-one)

3D PDB for NP0325127 ((1s,9r,19r,22r)-5-bromo-22-chloro-17-hydroxy-20,20-dimethyl-2,12,16,18-tetraazahexacyclo[10.10.0.0¹,⁹.0²,¹⁹.0³,⁸.0¹⁵,¹⁹]docosa-3,5,7,13,15,17-hexaen-11-one)

SMILES for NP0325127 ((1s,9r,19r,22r)-5-bromo-22-chloro-17-hydroxy-20,20-dimethyl-2,12,16,18-tetraazahexacyclo[10.10.0.0¹,⁹.0²,¹⁹.0³,⁸.0¹⁵,¹⁹]docosa-3,5,7,13,15,17-hexaen-11-one)

INCHI for NP0325127 ((1s,9r,19r,22r)-5-bromo-22-chloro-17-hydroxy-20,20-dimethyl-2,12,16,18-tetraazahexacyclo[10.10.0.0¹,⁹.0²,¹⁹.0³,⁸.0¹⁵,¹⁹]docosa-3,5,7,13,15,17-hexaen-11-one)

Structure for NP0325127 ((1s,9r,19r,22r)-5-bromo-22-chloro-17-hydroxy-20,20-dimethyl-2,12,16,18-tetraazahexacyclo[10.10.0.0¹,⁹.0²,¹⁹.0³,⁸.0¹⁵,¹⁹]docosa-3,5,7,13,15,17-hexaen-11-one)

3D Structure for NP0325127 ((1s,9r,19r,22r)-5-bromo-22-chloro-17-hydroxy-20,20-dimethyl-2,12,16,18-tetraazahexacyclo[10.10.0.0¹,⁹.0²,¹⁹.0³,⁸.0¹⁵,¹⁹]docosa-3,5,7,13,15,17-hexaen-11-one)