NP-MRD: Showing NP-Card for 3,4-dibromo-12,14-dihydroxy-2,8,11,13-tetraazatetracyclo[7.6.0.0²,⁶.0¹⁰,¹⁴]pentadeca-3,5,11-trien-7-one (NP0178483)

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Record Information

Version

2.0

Created at

2022-09-03 16:29:07 UTC

Updated at

2022-09-03 16:29:07 UTC

NP-MRD ID

NP0178483

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4-dibromo-12,14-dihydroxy-2,8,11,13-tetraazatetracyclo[7.6.0.0²,⁶.0¹⁰,¹⁴]pentadeca-3,5,11-trien-7-one

Description

3,4-Dibromo-12,14-dihydroxy-2,8,11,13-tetraazatetracyclo[7.6.0.0²,⁶.0¹⁰,¹⁴]Pentadeca-3,5,11-trien-7-one belongs to the class of organic compounds known as 2-heteroaryl carboxamides. 2-Heteroaryl carboxamides are compounds containing a heteroaromatic ring that carries a carboxamide group. 3,4-Dibromo-12,14-dihydroxy-2,8,11,13-tetraazatetracyclo[7.6.0.0²,⁶.0¹⁰,¹⁴]Pentadeca-3,5,11-trien-7-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 33  0  0  0  0  0  0  0  0999 V2000
   -4.8257    0.3567   -0.1374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5723    0.2200    0.0218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6172    1.2031    0.3980 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3122    0.6105    0.5358 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4764    0.8505   -0.7067 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2511    2.0800   -0.6889 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5901    2.0714   -0.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1598    3.1746    0.0835 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3067    0.8172   -0.0916 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6079    0.5128    0.3246 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7170   -0.8581    0.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2647   -1.9190    0.6514 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.5230   -1.3521   -0.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1777   -3.2080   -0.5400 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.6738   -0.3147   -0.4207 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3067   -0.3899   -0.8899 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4242   -1.5025   -0.1641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5966   -0.8755    0.5553 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7541   -1.3690    1.8493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8395   -1.0107   -0.1549 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8348    2.2090    0.5513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7889    0.8861    1.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2146    0.9264   -1.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1860    2.9981   -1.0176 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3414    1.2129    0.6459 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3146   -0.6914   -1.9750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2444   -1.8919    0.6465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7081   -2.3375   -0.8228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1046   -0.5981    2.3868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2236   -1.8107   -0.7189 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 19  1  1
 18 17  1  0
 17 16  1  0
 16  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 13 15  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 20  1  0
  4 18  1  0
 20 18  1  0
 15 16  1  0
 15  9  1  0
 19 29  1  0
 17 27  1  0
 17 28  1  0
 16 26  1  6
  5 23  1  6
  6 24  1  0
 10 25  1  0
  4 22  1  1
  3 21  1  0
 20 30  1  0
M  END


  Mrv1533004251508162D          

 20 23  0  0  0  0            999 V2000
   -0.4833   -2.4336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4262   -1.6106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3389   -1.9193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8689   -1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4314   -0.5876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8183    0.1410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6428    0.1702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0297    0.8989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0803   -0.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8929   -0.6720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0081   -1.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7367   -1.8759    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.2668   -1.8510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1239   -2.6635    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.6934   -1.2578    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3690   -0.7876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1341   -0.4789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6641   -1.1112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4871   -1.0541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2266   -1.8106    0.0000 N   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  4 15  1  0  0  0  0
  9 15  1  0  0  0  0
  5 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  2 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0178483

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC12CC3C(NC(=O)C4=CC(Br)=C(Br)N34)C1NC(=O)N2

> <INCHI_IDENTIFIER>
InChI=1S/C11H10Br2N4O3/c12-3-1-4-9(18)14-6-5(17(4)8(3)13)2-11(20)7(6)15-10(19)16-11/h1,5-7,20H,2H2,(H,14,18)(H2,15,16,19)

> <INCHI_KEY>
XDTDQGZBMQLKIM-UHFFFAOYSA-N

> <FORMULA>
C11H10Br2N4O3

> <MOLECULAR_WEIGHT>
406.034

> <EXACT_MASS>
403.911966

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
29.347769206401168

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,4-dibromo-14-hydroxy-2,8,11,13-tetraazatetracyclo[7.6.0.0²,⁶.0¹⁰,¹⁴]pentadeca-3,5-diene-7,12-dione

> <ALOGPS_LOGP>
0.34

> <JCHEM_LOGP>
0.2260900773333334

> <ALOGPS_LOGS>
-2.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.121605639492078

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.172058233560868

> <JCHEM_PKA_STRONGEST_BASIC>
-1.353316426988425

> <JCHEM_POLAR_SURFACE_AREA>
95.38999999999999

> <JCHEM_REFRACTIVITY>
74.25359999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4-dibromo-14-hydroxy-2,8,11,13-tetraazatetracyclo[7.6.0.0²,⁶.0¹⁰,¹⁴]pentadeca-3,5-diene-7,12-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  O   UNK     0      -0.902  -4.543   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.795  -3.007   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.633  -3.583   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.622  -2.402   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.805  -1.097   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       1.528   0.263   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       3.067   0.318   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.789   1.678   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.883  -0.988   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.400  -1.254   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.615  -2.779   0.000  0.00  0.00           C+0
HETATM   12 Br   UNK     0       6.975  -3.502   0.000  0.00  0.00          Br+0
HETATM   13  C   UNK     0       4.231  -3.455   0.000  0.00  0.00           C+0
HETATM   14 Br   UNK     0       3.965  -4.972   0.000  0.00  0.00          Br+0
HETATM   15  N   UNK     0       3.161  -2.348   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      -0.689  -1.470   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -2.117  -0.894   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      -3.106  -2.074   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.643  -1.968   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0      -2.290  -3.380   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   16   20                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   15                                                  
CONECT    5    4    6   16                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    4    9                                                  
CONECT   16    5    2   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    2                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₀Br₂N₄O₃

Average Mass

406.0340 Da

Monoisotopic Mass

403.91197 Da

IUPAC Name

3,4-dibromo-14-hydroxy-2,8,11,13-tetraazatetracyclo[7.6.0.0²,⁶.0¹⁰,¹⁴]pentadeca-3,5-diene-7,12-dione

Traditional Name

3,4-dibromo-14-hydroxy-2,8,11,13-tetraazatetracyclo[7.6.0.0²,⁶.0¹⁰,¹⁴]pentadeca-3,5-diene-7,12-dione

CAS Registry Number

Not Available

SMILES

OC12CC3C(NC(=O)C4=CC(Br)=C(Br)N34)C1NC(=O)N2

InChI Identifier

InChI=1S/C11H10Br2N4O3/c12-3-1-4-9(18)14-6-5(17(4)8(3)13)2-11(20)7(6)15-10(19)16-11/h1,5-7,20H,2H2,(H,14,18)(H2,15,16,19)

InChI Key

XDTDQGZBMQLKIM-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-heteroaryl carboxamides. 2-Heteroaryl carboxamides are compounds containing a heteroaromatic ring that carries a carboxamide group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

2-heteroaryl carboxamides

Alternative Parents

Substituents

2-heteroaryl carboxamide
Aryl bromide
Aryl halide
Substituted pyrrole
Cyclic alcohol
2-imidazoline
Pyrrole
Heteroaromatic compound
Isourea
Lactam
Secondary carboxylic acid amide
Carboximidamide
Azacycle
Alkanolamine
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organobromide
Organohalogen compound
Organic oxide
Organopnictogen compound
Organic oxygen 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	0.34	ALOGPS
logP	0.23	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	10.17	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	95.39 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	74.25 m³·mol⁻¹	ChemAxon
Polarizability	29.35 Å³	ChemAxon
Number of Rings	4	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

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

75148998

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,4-dibromo-12,14-dihydroxy-2,8,11,13-tetraazatetracyclo[7.6.0.0²,⁶.0¹⁰,¹⁴]pentadeca-3,5,11-trien-7-one (NP0178483)

MOL for NP0178483 (3,4-dibromo-12,14-dihydroxy-2,8,11,13-tetraazatetracyclo[7.6.0.0²,⁶.0¹⁰,¹⁴]pentadeca-3,5,11-trien-7-one)

3D MOL for NP0178483 (3,4-dibromo-12,14-dihydroxy-2,8,11,13-tetraazatetracyclo[7.6.0.0²,⁶.0¹⁰,¹⁴]pentadeca-3,5,11-trien-7-one)

3D SDF for NP0178483 (3,4-dibromo-12,14-dihydroxy-2,8,11,13-tetraazatetracyclo[7.6.0.0²,⁶.0¹⁰,¹⁴]pentadeca-3,5,11-trien-7-one)

3D-SDF for NP0178483 (3,4-dibromo-12,14-dihydroxy-2,8,11,13-tetraazatetracyclo[7.6.0.0²,⁶.0¹⁰,¹⁴]pentadeca-3,5,11-trien-7-one)

PDB for NP0178483 (3,4-dibromo-12,14-dihydroxy-2,8,11,13-tetraazatetracyclo[7.6.0.0²,⁶.0¹⁰,¹⁴]pentadeca-3,5,11-trien-7-one)

3D PDB for NP0178483 (3,4-dibromo-12,14-dihydroxy-2,8,11,13-tetraazatetracyclo[7.6.0.0²,⁶.0¹⁰,¹⁴]pentadeca-3,5,11-trien-7-one)

SMILES for NP0178483 (3,4-dibromo-12,14-dihydroxy-2,8,11,13-tetraazatetracyclo[7.6.0.0²,⁶.0¹⁰,¹⁴]pentadeca-3,5,11-trien-7-one)

INCHI for NP0178483 (3,4-dibromo-12,14-dihydroxy-2,8,11,13-tetraazatetracyclo[7.6.0.0²,⁶.0¹⁰,¹⁴]pentadeca-3,5,11-trien-7-one)

Structure for NP0178483 (3,4-dibromo-12,14-dihydroxy-2,8,11,13-tetraazatetracyclo[7.6.0.0²,⁶.0¹⁰,¹⁴]pentadeca-3,5,11-trien-7-one)

3D Structure for NP0178483 (3,4-dibromo-12,14-dihydroxy-2,8,11,13-tetraazatetracyclo[7.6.0.0²,⁶.0¹⁰,¹⁴]pentadeca-3,5,11-trien-7-one)