NP-MRD: Showing NP-Card for 3,5-dibromo-8'-hydroxy-6',10',15'-triazaspiro[cyclohexane-1,3'-tetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadecane]-1'(15'),2,2'(7'),5,8',10',12'(16')-heptaen-4-one (NP0243539)

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Record Information

Version

2.0

Created at

2022-09-07 04:06:33 UTC

Updated at

2022-09-07 04:06:33 UTC

NP-MRD ID

NP0243539

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,5-dibromo-8'-hydroxy-6',10',15'-triazaspiro[cyclohexane-1,3'-tetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadecane]-1'(15'),2,2'(7'),5,8',10',12'(16')-heptaen-4-one

Description

Discorhabdin C belongs to the class of organic compounds known as phenanthrolines. These are aromatic polycyclic compounds containing the phenanthroline skeleton, which is a derivative of phenanthrene, and consists of two pyridine rings non-linearly joined by a benzene ring. 3,5-dibromo-8'-hydroxy-6',10',15'-triazaspiro[cyclohexane-1,3'-tetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadecane]-1'(15'),2,2'(7'),5,8',10',12'(16')-heptaen-4-one is found in Latrunculia apicalis. 3,5-dibromo-8'-hydroxy-6',10',15'-triazaspiro[cyclohexane-1,3'-tetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadecane]-1'(15'),2,2'(7'),5,8',10',12'(16')-heptaen-4-one was first documented in 2019 (PMID: 30654589). Based on a literature review very few articles have been published on Discorhabdin C (PMID: 32752009).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072206062D          

 25 29  0  0  0  0            999 V2000
    4.5994   -0.9970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1705   -0.2922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3457   -0.3113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9498   -1.0351    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.9168    0.3934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3126    1.1172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1374    1.1363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5663    0.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3911    0.4506    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.7085    1.8411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2796    2.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4548    2.5267    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0590    1.8029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2342    1.7839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8053    2.4886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8383    1.0600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2672    0.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0920    0.3744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4879    1.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3509   -0.5761    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8132   -1.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0025   -1.0489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7295   -0.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0317    0.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0355    0.8699    0.0000 N   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  1  0  0  0  0
  3  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 13 19  2  0  0  0  0
  6 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 17 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 16 25  1  0  0  0  0
M  END

     RDKit          3D

 38 42  0  0  0  0  0  0  0  0999 V2000
    2.7851    3.6646    1.5013 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4180    2.5547    1.0453 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3862    1.3662    1.8880 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9076    1.4582    3.7342 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.0038    0.2110    1.4124 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5830    0.0031    0.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6316    1.2244   -0.7767 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0094    2.3896   -0.3261 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0124    3.9059   -1.5396 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.5716   -0.9833   -0.6043 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4288   -2.3569   -0.0620 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0939   -2.8241    0.1273 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0095   -1.9602   -0.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184   -2.4577   -0.0828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5862   -3.7949   -0.0421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3774   -1.5795   -0.2073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1277   -0.2440   -0.2495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8503    0.2526   -0.1715 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2186   -0.6037   -0.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7131    1.5282   -0.2224 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7704    2.4765   -0.3531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1538    1.9245   -0.4285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2171    0.4502   -0.3672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3055   -0.5354   -0.4075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7942   -1.7305   -0.3121 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0101   -0.6328    2.1170 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3217    1.1622   -1.8681 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6071   -0.6277   -0.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3358   -0.9861   -1.6876 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0601   -2.4369    0.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9166   -3.0587   -0.8005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9029   -3.8248    0.3687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9517   -4.5596    0.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7115    3.1953    0.5114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5735    3.0682   -1.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6649    2.3104   -1.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7372    2.2913    0.4681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3420   -0.2405   -0.5029 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 16  2  0
 16 25  1  0
 25 24  2  0
 24 23  1  0
 23 17  2  0
 17 18  1  0
 18 20  2  0
 20 21  1  0
 21 22  1  0
 18 19  1  0
 19 13  2  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  6  1  0
  6  5  1  0
  5  3  2  0
  3  4  1  0
  3  2  1  0
  2  1  2  0
  2  8  1  0
  8  9  1  0
  8  7  2  0
 13 14  1  0
  7  6  1  0
 17 16  1  0
  6 19  1  0
 22 23  1  0
 15 33  1  0
 24 38  1  0
 21 34  1  0
 21 35  1  0
 22 36  1  0
 22 37  1  0
 12 32  1  0
 11 30  1  0
 11 31  1  0
 10 28  1  0
 10 29  1  0
  5 26  1  0
  7 27  1  0
M  END


  Mrv1652309072206062D          

 25 29  0  0  0  0            999 V2000
    4.5994   -0.9970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1705   -0.2922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3457   -0.3113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9498   -1.0351    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.9168    0.3934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3126    1.1172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1374    1.1363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5663    0.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3911    0.4506    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.7085    1.8411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2796    2.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4548    2.5267    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0590    1.8029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2342    1.7839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8053    2.4886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8383    1.0600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2672    0.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0920    0.3744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4879    1.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3509   -0.5761    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8132   -1.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0025   -1.0489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7295   -0.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0317    0.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0355    0.8699    0.0000 N   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  1  0  0  0  0
  3  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 13 19  2  0  0  0  0
  6 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 17 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 16 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0243539

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=C2N=CC3=C2C(=NCC3)C2=C1NCCC21C=C(Br)C(=O)C(Br)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H13Br2N3O2/c19-9-5-18(6-10(20)16(9)24)2-4-22-15-12(18)13-11-8(1-3-21-13)7-23-14(11)17(15)25/h5-7,22,25H,1-4H2

> <INCHI_KEY>
AQUBTUIPDMTCAG-UHFFFAOYSA-N

> <FORMULA>
C18H13Br2N3O2

> <MOLECULAR_WEIGHT>
463.129

> <EXACT_MASS>
460.937453

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
38.372694769689296

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5-dibromo-8'-hydroxy-6',10',15'-triazaspiro[cyclohexane-1,3'-tetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadecane]-1'(15'),2,2'(7'),5,8',10',12'(16')-heptaen-4-one

> <JCHEM_LOGP>
0.32576483208792045

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.499884767166913

> <JCHEM_PKA_STRONGEST_BASIC>
7.245148281754106

> <JCHEM_POLAR_SURFACE_AREA>
74.05

> <JCHEM_REFRACTIVITY>
107.90379999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3,5-dibromo-8'-hydroxy-6',10',15'-triazaspiro[cyclohexane-1,3'-tetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadecane]-1'(15'),2,2'(7'),5,8',10',12'(16')-heptaen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  O   UNK     0       8.585  -1.861   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       7.785  -0.546   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.245  -0.581   0.000  0.00  0.00           C+0
HETATM    4 Br   UNK     0       5.506  -1.932   0.000  0.00  0.00          Br+0
HETATM    5  C   UNK     0       5.445   0.734   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.184   2.086   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.723   2.121   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.524   0.806   0.000  0.00  0.00           C+0
HETATM    9 Br   UNK     0      10.063   0.841   0.000  0.00  0.00          Br+0
HETATM   10  C   UNK     0       6.923   3.437   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.122   4.752   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       4.582   4.717   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       3.843   3.365   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.304   3.330   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.503   4.645   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.565   1.979   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.365   0.663   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.905   0.699   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.644   2.050   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       4.388  -1.075   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       3.385  -2.243   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.871  -1.958   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.362  -0.505   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.059   0.089   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0       0.066   1.624   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   10   19                                             
CONECT    7    6    8                                                       
CONECT    8    7    2    9                                                  
CONECT    9    8                                                            
CONECT   10    6   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   25                                                  
CONECT   17   16   18   23                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   13    6                                                  
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   17   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   16                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

View in JSmol

Synonyms

Value	Source
2',6'-Dibromo-8-hydroxyspiro(6,10,15-triazatetracyclo(7.6.1.02,7.012,16)hexadeca-1(15),2(7),8,10,12(16)-pentaene-3,4'-cyclohexa-2,5-diene)-1'-one	MeSH

Chemical Formula

C₁₈H₁₃Br₂N₃O₂

Average Mass

463.1290 Da

Monoisotopic Mass

460.93745 Da

IUPAC Name

3,5-dibromo-8'-hydroxy-6',10',15'-triazaspiro[cyclohexane-1,3'-tetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadecane]-1'(15'),2,2'(7'),5,8',10',12'(16')-heptaen-4-one

Traditional Name

3,5-dibromo-8'-hydroxy-6',10',15'-triazaspiro[cyclohexane-1,3'-tetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadecane]-1'(15'),2,2'(7'),5,8',10',12'(16')-heptaen-4-one

CAS Registry Number

Not Available

SMILES

OC1=C2N=CC3=C2C(=NCC3)C2=C1NCCC21C=C(Br)C(=O)C(Br)=C1

InChI Identifier

InChI=1S/C18H13Br2N3O2/c19-9-5-18(6-10(20)16(9)24)2-4-22-15-12(18)13-11-8(1-3-21-13)7-23-14(11)17(15)25/h5-7,22,25H,1-4H2

InChI Key

AQUBTUIPDMTCAG-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, 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
Latrunculia apicalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrolines. These are aromatic polycyclic compounds containing the phenanthroline skeleton, which is a derivative of phenanthrene, and consists of two pyridine rings non-linearly joined by a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Phenanthrolines

Sub Class

Not Available

Direct Parent

Phenanthrolines

Alternative Parents

Substituents

1,7-phenanthroline
Aminoquinoline
Tetrahydroquinoline
Indole or derivatives
Aralkylamine
Secondary aliphatic/aromatic amine
Benzenoid
Alpha-haloketone
Cyclic ketone
Ketone
Azacycle
Bromoalkene
Haloalkene
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Vinyl halide
Vinyl bromide
Secondary amine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organobromide
Organohalogen compound
Imine
Carbonyl group
Amine
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	0.33	ChemAxon
pKa (Strongest Acidic)	8.5	ChemAxon
pKa (Strongest Basic)	7.25	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.05 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	107.9 m³·mol⁻¹	ChemAxon
Polarizability	38.37 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

C00027081

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

184469

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lam CFC, Cadelis MM, Copp BR: Exploration of the Electrophilic Reactivity of the Cytotoxic Marine Alkaloid Discorhabdin C and Subsequent Discovery of a New Dimeric C-1/N-13-Linked Discorhabdin Natural Product. Mar Drugs. 2020 Jul 31;18(8):404. doi: 10.3390/md18080404. [PubMed:32752009 ]
Kalinski JJ, Waterworth SC, Noundou XS, Jiwaji M, Parker-Nance S, Krause RWM, McPhail KL, Dorrington RA: Molecular Networking Reveals Two Distinct Chemotypes in Pyrroloiminoquinone-Producing Tsitsikamma favus Sponges. Mar Drugs. 2019 Jan 16;17(1):60. doi: 10.3390/md17010060. [PubMed:30654589 ]
LOTUS database [Link]

Showing NP-Card for 3,5-dibromo-8'-hydroxy-6',10',15'-triazaspiro[cyclohexane-1,3'-tetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadecane]-1'(15'),2,2'(7'),5,8',10',12'(16')-heptaen-4-one (NP0243539)

MOL for NP0243539 (3,5-dibromo-8'-hydroxy-6',10',15'-triazaspiro[cyclohexane-1,3'-tetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadecane]-1'(15'),2,2'(7'),5,8',10',12'(16')-heptaen-4-one)

3D MOL for NP0243539 (3,5-dibromo-8'-hydroxy-6',10',15'-triazaspiro[cyclohexane-1,3'-tetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadecane]-1'(15'),2,2'(7'),5,8',10',12'(16')-heptaen-4-one)

3D SDF for NP0243539 (3,5-dibromo-8'-hydroxy-6',10',15'-triazaspiro[cyclohexane-1,3'-tetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadecane]-1'(15'),2,2'(7'),5,8',10',12'(16')-heptaen-4-one)

3D-SDF for NP0243539 (3,5-dibromo-8'-hydroxy-6',10',15'-triazaspiro[cyclohexane-1,3'-tetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadecane]-1'(15'),2,2'(7'),5,8',10',12'(16')-heptaen-4-one)

PDB for NP0243539 (3,5-dibromo-8'-hydroxy-6',10',15'-triazaspiro[cyclohexane-1,3'-tetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadecane]-1'(15'),2,2'(7'),5,8',10',12'(16')-heptaen-4-one)

3D PDB for NP0243539 (3,5-dibromo-8'-hydroxy-6',10',15'-triazaspiro[cyclohexane-1,3'-tetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadecane]-1'(15'),2,2'(7'),5,8',10',12'(16')-heptaen-4-one)

SMILES for NP0243539 (3,5-dibromo-8'-hydroxy-6',10',15'-triazaspiro[cyclohexane-1,3'-tetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadecane]-1'(15'),2,2'(7'),5,8',10',12'(16')-heptaen-4-one)

INCHI for NP0243539 (3,5-dibromo-8'-hydroxy-6',10',15'-triazaspiro[cyclohexane-1,3'-tetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadecane]-1'(15'),2,2'(7'),5,8',10',12'(16')-heptaen-4-one)

Structure for NP0243539 (3,5-dibromo-8'-hydroxy-6',10',15'-triazaspiro[cyclohexane-1,3'-tetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadecane]-1'(15'),2,2'(7'),5,8',10',12'(16')-heptaen-4-one)

3D Structure for NP0243539 (3,5-dibromo-8'-hydroxy-6',10',15'-triazaspiro[cyclohexane-1,3'-tetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadecane]-1'(15'),2,2'(7'),5,8',10',12'(16')-heptaen-4-one)