NP-MRD: Showing NP-Card for Dibromophakellin (NP0069813)

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Record Information

Version

2.0

Created at

2022-04-28 15:08:47 UTC

Updated at

2022-04-28 15:08:47 UTC

NP-MRD ID

NP0069813

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dibromophakellin

Description

(1R,5R)-7,8-dibromo-3-imino-2,4,6,12-tetraazatetracyclo[10.3.0.0¹,⁵.0⁶,¹⁰]Pentadeca-7,9-dien-11-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. Dibromophakellin is found in Phakellia mauretiana, Phakellia mauritiana and Stylissa massa. Based on a literature review very few articles have been published on (1R,5R)-7,8-dibromo-3-imino-2,4,6,12-tetraazatetracyclo[10.3.0.0¹,⁵.0⁶,¹⁰]Pentadeca-7,9-dien-11-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 33  0  0  0  0  0  0  0  0999 V2000
   -1.8597    3.2791   -0.0441 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0084    2.1679    0.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1838    2.0026   -0.3990 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6623    0.7851    0.1046 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8294    0.1487   -0.2768 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9925   -1.1481    0.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2668   -1.5407   -0.2908 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9018   -0.4665   -0.8550 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6905   -0.4484   -1.5202 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.9883    0.5844   -0.8408 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3539    2.3110   -1.5092 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.8187   -1.9282    0.5619 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0419   -3.1288    0.8709 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4323   -1.3169    0.6676 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7726   -1.6919    0.9978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5464   -1.0623   -0.2167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4517   -0.2419   -0.9681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5570    0.0055    0.2360 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2893    0.9986    1.0044 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0331    3.9480    0.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3418    3.4799   -0.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8499    1.1048    1.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7247   -2.5108   -0.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0604   -1.1400    1.9148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9625   -2.7645    1.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3159   -0.4068    0.1959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9191   -1.8720   -0.8595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9909   -0.8274   -1.7565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9246    0.6955   -1.2414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8390    0.9841    1.8438 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5 10  1  0
 10 11  1  0
 10  8  2  0
  8  9  1  0
  8  7  1  0
  7  6  2  0
  6 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
 19  2  1  0
 18  4  1  0
  6  5  1  0
 18 14  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  1
  7 23  1  0
 15 24  1  0
 15 25  1  0
 16 26  1  0
 16 27  1  0
 17 28  1  0
 17 29  1  0
 19 30  1  0
M  END


  Mrv1652304282217082D          

 19 22  0  0  1  0            999 V2000
    3.3523    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4663    3.1549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6458    3.2412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3102    2.4875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2333    3.9556    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1369    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6218    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1369    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3918    2.9750    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.4468    1.5229    0.0000 Br  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  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  1  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
  9 11  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  5 14  1  0  0  0  0
  2 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  1 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0069813

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=N[C@@H]2N3C(Br)=C(Br)C=C3C(=O)N3CCC[C@]23N1

> <INCHI_IDENTIFIER>
InChI=1S/C11H11Br2N5O/c12-5-4-6-8(19)17-3-1-2-11(17)9(15-10(14)16-11)18(6)7(5)13/h4,9H,1-3H2,(H3,14,15,16)/t9-,11-/m1/s1

> <INCHI_KEY>
MKCFBJDWCJAOTN-MWLCHTKSSA-N

> <FORMULA>
C11H11Br2N5O

> <MOLECULAR_WEIGHT>
389.051

> <EXACT_MASS>
386.933036

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
30.464318203738543

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,5R)-3-amino-7,8-dibromo-2,4,6,12-tetraazatetracyclo[10.3.0.0^{1,5}.0^{6,10}]pentadeca-3,7,9-trien-11-one

> <ALOGPS_LOGP>
1.14

> <JCHEM_LOGP>
1.5456910183333334

> <ALOGPS_LOGS>
-2.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.664324856770227

> <JCHEM_POLAR_SURFACE_AREA>
75.65

> <JCHEM_REFRACTIVITY>
75.93280000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.37e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5R)-3-amino-7,8-dibromo-2,4,6,12-tetraazatetracyclo[10.3.0.0^{1,5}.0^{6,10}]pentadeca-3,7,9-trien-11-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  N   UNK     0       6.258   3.613   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.924  -0.237   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       3.590   2.073   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       4.604   5.889   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       3.072   6.050   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       2.446   4.643   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       2.302   7.384   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.722   1.597   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.627   2.843   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.722   4.089   0.000  0.00  0.00           C+0
HETATM   18 Br   UNK     0       8.198   5.553   0.000  0.00  0.00          Br+0
HETATM   19 Br   UNK     0      10.167   2.843   0.000  0.00  0.00          Br+0
CONECT    1    2    7   17                                                  
CONECT    2    1    3   15                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   14                                                  
CONECT    6    5    7   10   12                                             
CONECT    7    6    1    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9    6                                                       
CONECT   11    9                                                            
CONECT   12    6   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    5                                                       
CONECT   15    2   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16    1   18                                                  
CONECT   18   17                                                            
CONECT   19   16                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₁Br₂N₅O

Average Mass

389.0510 Da

Monoisotopic Mass

386.93304 Da

IUPAC Name

(1R,5R)-3-amino-7,8-dibromo-2,4,6,12-tetraazatetracyclo[10.3.0.0^{1,5}.0^{6,10}]pentadeca-3,7,9-trien-11-one

Traditional Name

(1R,5R)-3-amino-7,8-dibromo-2,4,6,12-tetraazatetracyclo[10.3.0.0^{1,5}.0^{6,10}]pentadeca-3,7,9-trien-11-one

CAS Registry Number

Not Available

SMILES

NC1=N[C@@H]2N3C(Br)=C(Br)C=C3C(=O)N3CCC[C@]23N1

InChI Identifier

InChI=1S/C11H11Br2N5O/c12-5-4-6-8(19)17-3-1-2-11(17)9(15-10(14)16-11)18(6)7(5)13/h4,9H,1-3H2,(H3,14,15,16)/t9-,11-/m1/s1

InChI Key

MKCFBJDWCJAOTN-MWLCHTKSSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Phakellia mauretiana	Animalia	KNApSAcK
Phakellia mauritiana	Animalia	KNApSAcK
Stylissa massa	LOTUS Database	35616633

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
Substituted pyrrole
Aryl halide
Aryl bromide
Heteroaromatic compound
Tertiary carboxylic acid amide
Pyrrolidine
Pyrrole
2-imidazoline
Lactam
Guanidine
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organobromide
Organohalogen 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	1.14	ALOGPS
logP	1.55	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Basic)	8.66	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.65 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	75.93 m³·mol⁻¹	ChemAxon
Polarizability	30.46 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

162923454

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Dibromophakellin (NP0069813)

MOL for NP0069813 (Dibromophakellin)

3D MOL for NP0069813 (Dibromophakellin)

3D SDF for NP0069813 (Dibromophakellin)

3D-SDF for NP0069813 (Dibromophakellin)

PDB for NP0069813 (Dibromophakellin)

3D PDB for NP0069813 (Dibromophakellin)

SMILES for NP0069813 (Dibromophakellin)

INCHI for NP0069813 (Dibromophakellin)

Structure for NP0069813 (Dibromophakellin)

3D Structure for NP0069813 (Dibromophakellin)